Document:

EX-10.2

 Exhibit 10.2 

Execution Version 

SUBSCRIPTION AGREEMENT 

This Subscription Agreement is entered into and dated as of October 28, 2022 (this “Agreement”), by and
among TherapeuticsMD, Inc., a Nevada corporation with offices located at 951 Yamato Road, Suite 220, Boca Raton, FL 33431 (the “Company”), and the Subscribers identified on the Schedule of Subscribers attached hereto (each, a
“Subscriber” and, together, the “Subscribers”). Capitalized terms not defined below shall have the meaning as set forth in Section 1.1. 

RECITALS 

A. The Company and each Subscriber is executing and delivering this Agreement in reliance upon the exemption from securities
registration afforded by Section 4(a)(2) of the Securities Act of 1933, as amended (the “1933 Act”), and Rule 506 of Regulation D (“Regulation D”) as promulgated by the United States Securities and Exchange
Commission (the “Commission”) under the 1933 Act. 
 B. The Company is a borrower under that certain
Financing Agreement, dated as of April 24, 2019, by and among the Company, as borrower, certain subsidiaries of the Company, as guarantors, the lenders from time to time party thereto, and Sixth Street Specialty Lending, Inc. (f/k/a TPG
Specialty Lending, Inc.), as administrative agent for the lenders thereunder (as amended, amended and restated, supplemented or otherwise modified from time to time, the “Financing Agreement”). 

C. To induce the Subscribers (or Affiliates thereof) to further amend the Financing Agreement, the Company wishes to issue,
upon the terms and conditions stated in this Agreement, a warrant to acquire up to that aggregate number of shares of Common Stock set forth opposite such Subscriber’s name in column (3) on the Schedule of Subscribers, in the form
attached hereto as Exhibit A (the “Warrants”) (as exercised, collectively, the “Warrant Shares”), subject to adjustment for any stock split, stock dividend, stock combination, reclassification or similar
transaction. 
 D. The Warrants and the Warrant Shares are collectively referred to herein as the
“Securities.” 
 NOW, THEREFORE, IN CONSIDERATION of the mutual covenants contained in this Agreement, and
for other good and valuable consideration, the receipt and adequacy of which are hereby acknowledged, the Company and each Subscriber, severally and not jointly, agree as follows: 

ARTICLE I. 
 DEFINITIONS 

1.1 Definitions. In addition to the terms defined elsewhere in this Agreement, the following terms shall have the
meanings set forth in this Section 1.1: 

 “1934 Act” means the Securities Exchange Act of 1934, as
amended, and the rules and regulations promulgated thereunder. 
 “Affiliate” shall have the meaning
ascribed to such term in Rule 405 of the 1933 Act. 
 “Business Day” means any day other than Saturday,
Sunday or other day on which commercial banks in the City of New York, New York are authorized or required by law to remain closed; provided, however, for clarification, commercial banks shall not be deemed to be authorized or required
by law to remain closed due to “stay at home”, “shelter-in-place”, “non-essential employee” or any
other similar orders or restrictions or the closure of any physical branch locations at the direction of any governmental authority so long as the electronic funds transfer systems (including for wire transfers) of commercial banks in the City of
New York, New York generally are open for use by customers on such day. 
 “Common Stock” means
(a) the Company’s shares of common stock, par value $0.001 per share, and (b) any share capital into which such common stock shall have been changed or any share capital resulting from a reclassification, reorganization or
recapitalization of such common stock. 
 “Designee” means Sixth Street Specialty Lending, Inc. 

“Eligible Market” means the Principal Market, the NYSE American, The Nasdaq Global Select Market, The Nasdaq
Global Market, The Nasdaq Capital Market or The New York Stock Exchange, Inc. 
 “Governmental Authority”
shall mean any: (a) nation, state, commonwealth, province, territory, county, municipality, district or other jurisdiction of any nature; (b) federal, state, provincial, local, municipal, foreign or other government; (c) governmental
or quasi-governmental authority of any nature (including any governmental division, department, agency, commission, commissioner, bureau, tribunal, instrumentality, official, ministry, fund, foundation, center, organization, board, unit, body or
Person and any court or other tribunal); or (d) regulatory or self-regulatory organization (including the Principal Market or other applicable Eligible Market). 

“Lien” means any mortgage, deed of trust, lien, charge, claim, encumbrance, security interest, right of first
refusal, preemptive right or other restrictions of any kind. 
 “Person” means an individual or
corporation, partnership, trust, incorporated or unincorporated association, joint venture, limited liability company, joint stock company, government (or an agency or subdivision thereof) or other entity of any kind. 

“Principal Market” means The Nasdaq Stock Market LLC. 

  
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 “Proceeding” means an action, claim, suit, inquiry,
investigation or proceeding (including, without limitation, an investigation or partial proceeding, such as a deposition), whether commenced or, to the Company’s knowledge, threatened in writing. 

“Required Holders” means the holders of Warrants representing at least a majority of the number of shares of
Common Stock issuable upon exercise of the Warrants then outstanding and shall include the Designee so long as the Designee or any of its Affiliates holds any Warrants. 

“SEC Reports” shall mean all reports, schedules, forms, applications and other documents, together with any
amendments required to be made with respect thereto, required to be filed by the Company under the 1933 Act and the 1934 Act, including pursuant to Section 13(a) or 15(d) thereof, for the two (2) years preceding the date hereof (or such
shorter period as the Company was required by law or regulation to file such materials). 
 “Subsidiary”
has the meaning as set forth in the Financing Agreement. 
 “Trading Day” means any day on which the Common
Stock is traded on the Principal Market, or, if the Principal Market is not the principal trading market for the Common Stock, then on the principal securities exchange or securities market on which the Common Stock is then traded. 

“Transaction Documents” means this Agreement, the Warrants and any other documents, certificates, letters of
instruction, or agreements executed or delivered in connection with the transactions contemplated hereby, but shall not include the Loan Documents (as defined in the Financing Agreement). 

ARTICLE II. 
 PURCHASE AND SALE

 2.1 Purchase and Sale of the Securities. Subject to the terms and conditions of this Agreement, each Subscriber
agrees, severally and not jointly, to purchase from the Company, and the Company agrees to sell and issue to each Subscriber, at the Closing, such Warrants to acquire up to that aggregate number of Warrant Shares as is set forth opposite such
Subscriber’s name in column (3) on the Schedule of Subscribers. 
 2.2 Closing. The issuance of the
Warrants pursuant to the terms of this Agreement (the “Closing”) shall take place remotely by electronic transfer of Closing documentation at 10:00 a.m. (New York City time) on the date hereof (the “Closing Date”).

 2.3 Form of Payment. On the Closing Date, the Company shall deliver to each Subscriber a Warrant pursuant to which
such Subscriber shall have the right to acquire up to such aggregate number of Warrant Shares as is set forth opposite such Subscriber’s name in column (3) of the Schedule of Subscribers, duly executed on behalf of the Company and
registered in the name of such Subscriber or its designee. 

  
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 ARTICLE III. 

REPRESENTATIONS AND WARRANTIES 

3.1 Representations and Warranties of the Company. The Company hereby represents and warrants as of the date hereof and
as of the Closing Date (except for representations and warranties that speak as of a specific date, which shall be made as of such date) to each of the Subscribers, except as set forth in the Schedules delivered herewith: 

(a) Authorization; Enforcement. The Company has the requisite corporate power and authority to enter into and to
consummate the transactions contemplated by each of the Transaction Documents and otherwise to carry out its respective obligations hereunder and thereunder. Other than the Required Approvals (as defined in Section 3.1(c)),
the execution and delivery by the Company of each of the Transaction Documents to which it is a party and the consummation by it of the transactions contemplated hereunder and thereunder have been duly authorized by all necessary action on the part
of the Company and no further consent or action is required by the Company, or its board of directors or stockholders. Each Transaction Document has been (or upon delivery will have been) duly executed by the Company, and, when delivered in
accordance with the terms hereof, will constitute the valid and binding obligation of the Company, enforceable against the Company, in accordance with its terms, except as such enforceability may be limited by general principles of equity or
applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights and remedies and except as rights to indemnification and to
contribution may be limited by federal or state securities law. 
 (b) No Conflicts. The execution, delivery and
performance of the Transaction Documents by the Company and the consummation by the Company of the transactions contemplated hereby and thereby (including, without limitation, the issuance of the Warrants and the Warrant Shares and the reservation
for issuance of the Warrant Shares) do not and will not (i) conflict with or violate any provision of the Company’s or any of its Subsidiaries’ certificate or articles of incorporation, bylaws or other organizational or charter
documents, (ii) conflict with, or constitute a default (or an event that with notice or lapse of time or both would become a default) under, result in the creation of any Lien upon any of the properties or assets of the Company or any of its
Subsidiaries, or give to others any rights of termination, amendment, acceleration or cancellation (with or without notice, lapse of time or both) of, any agreement, credit facility, debt or other instrument (evidencing a Company or a Company
Subsidiary’s debt or otherwise) or other understanding to which the Company any of its Subsidiaries is a party or by which any property or asset of the Company or any of its Subsidiaries is bound or affected, or (iii) result in a violation
of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any Governmental Authority to which the Company or a Company Subsidiary is subject (including, without limitation, foreign, federal and state securities laws
and regulations and the rules and regulations of the Principal Market), or by which any property or asset of the Company or a Company Subsidiary is bound or affected; except in the case of clause (ii) or (iii) above, as would not, reasonably be
expected to, (i) have or result in a material adverse effect on the legality, validity, binding effect or enforceability of any Transaction Document, (ii) have or result in a material adverse effect on the business operations, properties,
assets, condition (financial or otherwise) or liabilities of the Company and its Subsidiaries, taken as a whole, or (iii) have or 

  
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result in a material adverse effect on the Company’s authority or ability to perform fully on a timely basis its obligations under any Transaction Document (any of (i), (ii) or (iii), a
“Material Adverse Effect”). 
 (c) Filings, Consents and Approvals. Neither the Company nor any
Company Subsidiary is required to obtain any consent, waiver, authorization, permit or order of, give any notice to, or make any filing or registration with, any Governmental Authority or other Person in connection with the execution, delivery and
performance by the Company of the Transaction Documents, other than (i) the filing by the Company of a Notice of Sale of Securities on Form D with the Commission under Regulation D and state and applicable Blue Sky filings, (ii) the filing
of any requisite notices and/or applications(s) to the Principal Market for the issuance and sale of the Warrants and the issuance of the Warrant Shares upon exercise of the Warrants and the listing of the Warrant Shares for trading thereon, and
(iii) the filing of a Current Report on Form 8-K, or the disclosure required thereby in another filing, with the Commission (collectively, but excluding the foregoing clauses (i) through (iii), the
“Required Approvals”). All Required Approvals have been obtained or effected on or prior to the Closing Date, and neither the Company nor any Company Subsidiary are aware of any facts or circumstances which might prevent the Company
or any Company Subsidiary from obtaining or effecting any of the registration, application or filings contemplated by the Transaction Documents. The Company is not in violation of any material requirements of the Principal Market and has no
knowledge of any facts or circumstances which would reasonably be expected to result in the delisting or suspension of the Common Stock in the foreseeable future. 

(d) Issuance of the Securities. The issuance of the Warrants is duly authorized and, upon issuance in accordance with
the terms of the Transaction Documents, the Warrants will be validly issued free from all preemptive or similar rights, taxes, Liens (other than Liens under the 1933 Act and applicable Blue Sky laws) and charges with respect to the issue thereof. As
of the Closing, the Company shall have reserved from its duly authorized capital stock not less than 100% of the maximum number of Warrant Shares issuable upon exercise of the Warrants (without taking into account any limitations on the exercise of
the Warrants set forth therein). Upon exercise in accordance with the Warrants, the Warrant Shares when issued, will be validly issued, fully paid and nonassessable and free from all preemptive or similar rights, taxes, Liens and charges with
respect to the issue thereof, with the holders being entitled to all rights accorded to a holder of Common Stock (as set forth in the applicable charter documents). Subject to the accuracy of the representations and warranties of the Subscribers in
this Agreement, the offer and issuance by the Company of the Securities is exempt from registration under the 1933 Act. 

(e) Capitalization. The number of shares and type of all authorized, issued and outstanding capital stock of the
Company has been set forth in the SEC Reports and has changed since the date set forth in the most recent applicable SEC Report only to reflect exercises of stock options and other convertible securities that have not been required to be reported by
the Company under the 1934 Act. Without limiting the foregoing, as of the date hereof, immediately prior to the issuance of the Warrants, the authorized capital stock of the Company consists of (i) 12,000,000 shares of Common Stock, of which
9,467,104 shares are issued and outstanding, 197,275 shares are reserved for issuance pursuant to issued and outstanding options, 411,044 shares are reserved 

  
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for issuance pursuant to issued and outstanding warrants, 466,456 shares are reserved for issuance pursuant to securities (other than the aforementioned options and warrants) exercisable or
exchangeable for, or convertible into, shares of Common Stock, 242,015 shares are reserved for issuance under the Company’s 2019 Stock Incentive Plan, and 96,010 shares are reserved for issuance under the Company’s 2020 Employee Stock
Purchase Plan; and (ii) 10,000,000 shares of preferred stock, par value $0.001 per share, of which 22,000 shares of Series A Preferred Stock are issued and outstanding (excluding shares to be issued on the date hereof). Other than as stated in the
immediately preceding sentence, the Company does not have any outstanding securities that are exercisable or exchangeable for, or convertible into, shares of Common Stock. All of such outstanding shares are duly authorized and have been, or upon
issuance will be, validly issued and are fully paid and nonassessable. No securities of the Company are entitled to preemptive or similar rights, and no Person has any right of first refusal, preemptive right, right of participation, or any similar
right to participate in the transactions contemplated by the Transaction Documents. There are no securities or instruments containing anti-dilution or similar provisions that will be triggered by the issuance of the Securities. The Company does not
have any stock appreciation rights or “phantom stock” or similar plans or agreements currently outstanding except as disclosed above. 

(f) Certain Fees. No brokerage or finder’s fees or commissions are or will be payable by the Subscribers to any
broker, financial advisor or consultant, finder, placement agent, investment banker, bank or other Person with respect to the transactions contemplated by this Agreement as a result of an agreement entered into by the Company. 

(g) Private Placement; No Integrated Offering; No General Solicitation; No Disqualification Events. Assuming in part
the accuracy of each Subscriber’s representations and warranties set forth in Section 3.2(c)-(g), (i) no registration under the 1933 Act is required for the offer and sale of the Securities by the Company to the
Subscribers under the Transaction Documents, and (ii) the issuance and sale of the Securities hereunder does not contravene the rules and regulations of the Principal Market. Assuming in part the accuracy of the Subscribers’
representations and warranties set forth in Section 3.2, neither the Company, the Company Subsidiaries, any of their respective Affiliates, nor any Person acting on their behalf has, directly or indirectly, made any offers
or sales of any Company security or solicited any offers to buy any security, under circumstances that would require registration of the issuance of any of the Securities under the 1933 Act, whether through integration with prior offerings or
otherwise or cause this offering of the Securities to require approval of stockholders of the Company for purposes of the 1933 Act or any applicable stockholder approval provisions, including, without limitation, under the rules and regulations of
any exchange or automated quotation system on which any of the securities of the Company are listed or designated. Neither the Company, the Company Subsidiaries nor their Affiliates, nor any Person acting on its or their behalf, has engaged in any
form of general solicitation or general advertising (within the meaning of Regulation D) in connection with the offer or sale of the Securities. With respect to Securities to be offered and sold hereunder in reliance on Rule 506(b) under the 1933
Act (“Regulation D Securities”), none of the Company, any of its predecessors, any affiliated issuer, any director, executive officer, other officer of the Company participating in the offering hereunder, any beneficial owner of 20%
or more of the Company’s outstanding voting equity securities, calculated on the basis of voting power, nor any promoter (as that term is defined in Rule 405 under the 1933 Act) connected with the Company in any capacity at the time of sale,
nor any other Person covered by Rule 506(d) 

  
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(each, an “Issuer Covered Person” and, together, “Issuer Covered Persons”) is or has been subject to any of the “Bad Actor” disqualifications described
in Rule 506(d)(1)(i) to (viii) under the 1933 Act (a “Disqualification Event”), except for a Disqualification Event covered by Rule 506(d)(2) or (d)(3). The Company has determined that no Issuer Covered Person is subject to a
Disqualification Event. The Company has complied, to the extent applicable, with its disclosure obligations under Rule 506(e), and has furnished to the Subscribers a copy of any disclosures provided thereunder. No Person has been or will be paid
(directly or indirectly) remuneration for solicitation of Subscribers or potential purchasers in connection with the sale of any Regulation D Securities. 

(h) Application of Takeover Protections. The Company and its Board of Directors have taken all necessary action, if
any, in order to render inapplicable any control share acquisition, interested stockholder, business combination, poison pill (including any distribution under a rights agreement, or similar arrangement or plan) or other similar anti-takeover
provision under the Company’s articles of incorporation and bylaws, each as amended, that is or could become applicable to the Subscribers as a result of the Subscribers and the Company fulfilling their obligations or exercising their rights
under the Transaction Documents, including without limitation as a result of the Company’s issuance of the Securities and the Subscribers’ ownership of the Securities. The Company and its Board of Directors have taken all necessary action,
if any, in order to render inapplicable any stockholder rights plan or similar arrangement now in effect relating to accumulations of beneficial ownership of shares of Common Stock or a change in control of the Company or any Company Subsidiary.

 (i) Transfer Taxes. On the Closing Date, all stock transfer or other taxes (other than income or similar taxes)
which are required to be paid in connection with the sale and transfer of the Securities to be sold to each Subscriber hereunder will be, or will have been, fully paid or provided for by the Company, and all laws imposing such taxes will be or will
have been complied with. 
 (j) Investment Company Status. Neither the Company nor any Company Subsidiary is, and
upon consummation of the sale of the Securities, will not be, an “investment company,” a company controlled by an “investment company” or an “affiliated person” of, or “promoter” or “principal
underwriter” for, an “investment company” as such terms are defined in the Investment Company Act of 1940, as amended. 

(k) U.S. Real Property Holding Corporation. The Company is not and has never been a U.S. real property holding
corporation within the meaning of Section 897 of the Internal Revenue Code of 1986, as amended, and the Company shall so certify upon any Subscriber’s request. 

(l) Loan Documents. The Company hereby acknowledges and agrees that each of the Transaction Documents constitutes a
“Loan Document” under the Financing Agreement, including for purposes of determining an Event of Default under the Financing Agreement. 

  
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 3.2 Representations and Warranties of the Subscribers. Each
Subscriber hereby, as to itself only and for no other Subscriber, represents and warrants as of the date hereof and as of the Closing Date (except for representations and warranties that speak as of a specific date, which shall be made as of such
date) to the Company as follows: 
 (a) Organization; Authority. Such Subscriber is an entity duly organized, validly
existing and in good standing under the laws of the jurisdiction of its organization with the requisite power and authority to enter into and to consummate the transactions contemplated by the Transaction Documents and otherwise to carry out its
obligations hereunder and thereunder. The execution, delivery and performance by such Subscriber of the Transaction Documents to which it is a party have been duly authorized by all necessary action on the part of such Subscriber. Each of the
Transaction Documents to which such Subscriber is a party has been duly executed by such Subscriber and, when delivered by such Subscriber in accordance with terms hereof, will constitute the valid and legally binding obligation of such Subscriber,
enforceable against it in accordance with its terms, except as such enforceability may be limited by general principles of equity or applicable bankruptcy, insolvency, reorganization, moratorium, liquidation or similar laws relating to, or affecting
generally, the enforcement of applicable creditors’ rights and remedies. 
 (b) No Conflicts. The execution,
delivery and performance of the Transaction Documents by such Subscriber and the consummation by such Subscriber of the transactions contemplated hereby and thereby do not and will not (i) conflict with or violate any provision of such
Subscriber’s certificate or articles of incorporation, bylaws or other organizational or charter documents, (ii) conflict with, or constitute a default (or an event which with notice or lapse of time or both would become a default) under,
or give to others any rights of termination, amendment, acceleration or cancellation of, any agreement, indenture or instrument to which such Subscriber is a party or by which any property or asset of such Subscriber is bound or affected, or
(iii) result in a violation of any law, rule, regulation, order, judgment, injunction, decree or other restriction of any Governmental Authority to which such Subscriber is subject (including, without limitation, foreign, federal and state
securities laws and regulations); except in the case of clause (ii) or (iii) above, as would not, reasonably be expected to have, individually or in the aggregate, a material adverse effect on the ability of the Subscriber to perform its
obligations thereunder. 
 (c) Investment Intent. Such Subscriber is acquiring the Securities as principal for its
own account for investment purposes and not with a view to distributing or reselling such Securities or any part thereof in violation of applicable securities laws, without prejudice, however, to such Subscriber’s right at all times to sell or
otherwise dispose of all or any part of such Securities in compliance with applicable federal and state securities laws. Nothing contained herein shall be deemed a representation or warranty by such Subscriber to hold the Securities for any period
of time. Notwithstanding the foregoing, such Subscriber understands that the Securities have not been registered under the 1933 Act, and therefore the Securities may not be sold, assigned or transferred unless pursuant to (i) an effective
registration statement under the 1933 Act with respect thereto or (ii) an available exemption from the registration requirements of the 1933 Act. Such Subscriber has been advised or is aware of the provisions of Rule 144 promulgated under the
1933 Act (or a successor rule thereto) (collectively, “Rule 144”) as in effect from time to time, which permit limited resale of shares purchased in a private placement subject to the satisfaction of certain conditions. 

  
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 (d) Subscriber Status. At the time such Subscriber was offered the
Securities, it was, and at the date hereof it is, and on each date on which it exercises the Warrants it will be, an “accredited investor” as defined in Rule 501(a) under the 1933 Act. 

(e) Experience of such Subscriber. Such Subscriber, either alone or together with its representatives, has such
knowledge, sophistication and experience in business and financial matters so as to be capable of evaluating the merits and risks of the prospective investment in the Securities, and has so evaluated the merits and risks of such investment. Such
Subscriber is able to bear the economic risk of an investment in the Securities and, at the present time, is able to afford a complete loss of such investment. 

(f) General Solicitation. Such Subscriber is not purchasing the Securities as a result of any advertisement, article,
notice or other communication regarding the Securities published in any newspaper, magazine or similar media or broadcast over television or radio or presented at any seminar or, to such Subscriber’s knowledge, any other general solicitation or
general advertisement. 
 (g) Access to Data. Such Subscriber has received and reviewed information about the Company
and has had an opportunity to discuss the Company’s business, management and financial affairs with its management and to review the Company’s facilities. Such Subscriber acknowledges that it has been afforded (i) the opportunity to
ask such questions as it has deemed necessary of, and to receive answers from, representatives of the Company concerning the terms and conditions of the offering of the Securities and the merits and risks of investing in the Securities;
(ii) access to information about the Company and its respective financial condition, results of operations, business, properties, management and prospects sufficient to enable it to evaluate its investment; and (iii) the opportunity to
obtain such additional information that the Company possesses or can acquire without unreasonable effort or expense that is necessary to make an informed investment decision with respect to the investment. In deciding to enter into this Agreement
and the transactions contemplated hereby, such Subscriber has not relied upon any representations and warranties other than the express representations and warranties contained in the Loan Documents. The foregoing, however, does not limit or modify
the representations and warranties made by the Company in this Agreement or any other provision in this Agreement or the right of the Subscribers to rely thereon. Such Subscriber has sought such accounting, legal and tax advice as it has considered
necessary to make an informed decision with respect to its acquisition of the Securities. 
 (h) Transfer or Resale.
Such Subscriber understands that: (i) the Securities have not been and are not being registered under the 1933 Act or any state securities laws, and may not be offered for sale, sold, assigned or transferred unless (A) subsequently
registered thereunder, (B) such Subscriber shall have delivered to the Company (if requested by the Company) an opinion of counsel to such Subscriber, reasonably satisfactory to the Company as to such counsel and to the form of opinion, to the
effect that such Securities may be sold, assigned or transferred without registration under the applicable requirements of the 1933 Act; provided, however, that Proskauer Rose LLP shall be deemed reasonably satisfactory to the Company;
provided, further, that no such opinion shall be required to sell, assign or otherwise transfer all or any portion of such Securities 

  
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to an Affiliate of the holder of the Securities, or (C) such Subscriber provides the Company with assurance reasonably satisfactory to the Company that such Securities can be sold, assigned
or transferred pursuant to Rule 144 or to an accredited investor in a private transaction exempt from the registration requirements of the 1933 Act; (ii) any sale of the Securities made in reliance on Rule 144 may be made only in accordance
with the terms of Rule 144; and (iii) neither the Company nor any other Person is under any obligation to register the Securities under the 1933 Act or any state securities laws or to comply with the terms and conditions of any exemption
thereunder. 
 (i) Reliance on Exemptions. Such Subscriber understands that the Securities are being offered and sold
to it in reliance on specific exemptions from the registration requirements of United States federal and state securities laws and that the Company is relying in part upon the truth and accuracy of, and such Subscriber’s compliance with, the
representations, warranties, agreements, acknowledgements and understandings of such Subscriber set forth herein in order to determine the availability of such exemptions and the eligibility of such Subscriber to acquire the Securities. 

(j) No Governmental Review. Such Subscriber understands that no United States federal or state agency or any other
government or governmental agency has passed on or made any recommendation or endorsement of the Securities or the fairness or suitability of the investment in the Securities nor have such authorities passed upon or endorsed the merits of the
offering of the Securities. 
 (k) Legends. Such Subscriber understands that the certificates or other instruments
representing the Warrants and the stock certificates representing the Warrant Shares, except as set forth below, shall bear a restrictive legend in substantially the following form (and a stop-transfer order may be placed against transfer of such
stock certificates): 
 [NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS WARRANT
NOR THE SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE HAVE BEEN][THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN] REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE
SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED IN THE ABSENCE OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR (B) AN OPINION OF COUNSEL SELECTED BY THE
HOLDER, IN A FORM REASONABLY SATISFACTORY TO THE COMPANY, THAT REGISTRATION IS NOT REQUIRED UNDER SAID ACT. NOTWITHSTANDING THE FOREGOING, THE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN OR FINANCING
ARRANGEMENT SECURED BY THE SECURITIES. 

  
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 The legend set forth above shall be removed and the Company shall issue a certificate
without such legend to the holder of the Securities upon which it is stamped or issue to such holder by electronic delivery at the applicable balance account at The Depository Trust Company (“DTC”), if (i) such Securities are
registered for resale under the 1933 Act and the holder has delivered to the Company a representation that such Securities have been sold pursuant to such registration statement, or (ii) in connection with a sale, assignment or other transfer,
such holder provides the Company with an opinion of counsel, reasonably satisfactory to the Company as to such counsel and to the form of opinion, to the effect that such sale, assignment or transfer of the Securities may be made (or was made, as
applicable under Rule 144) without registration under the applicable requirements of the 1933 Act; provided, however, that Proskauer Rose LLP shall be deemed reasonably satisfactory to the Company; provided, further, that
no such opinion shall be required to sell, assign or otherwise transfer all or any portion of such Securities to an Affiliate of the holder of the Securities. The Company shall be responsible for the fees of its transfer agent and all DTC fees
associated with such issuance. 
 The Company acknowledges and agrees that no Subscriber makes or has made any representations or warranties
with respect to the transactions contemplated hereby or by any other Transaction Document other than those specifically set forth in Section 3.2. 

ARTICLE IV. 
 OTHER AGREEMENTS OF
THE PARTIES 
 4.1 Register; Pledge. 

(a) The Company shall maintain at its principal executive offices (or such other office or agency of the Company as it may
designate by notice to each holder of Securities), a register for each series of the Warrants in which the Company shall record the name and address of the Person in whose name the Warrants have been issued (including the name and address of each
permitted transferee) the number of Warrant Shares issuable upon exercise of the Warrants held by such Person. The Company shall keep the register open and available at all times during business hours upon reasonable notice for inspection of any
Subscriber or its legal representatives. 
 (b) The Company acknowledges and agrees that a Subscriber may from time to time
pledge or grant a security interest in some or all of the Securities in connection with a bona fide margin agreement secured by the Securities and, if required under the terms of such agreement, such Subscriber may transfer pledged or secured
Securities to the pledgees or secured parties. Such a pledge or transfer would not be subject to approval of the Company and no legal opinion of the pledgee, secured party or pledgor shall be required in connection therewith. Further, no notice
shall be required of such pledge. At the appropriate Subscriber’s expense, the Company will execute and deliver such reasonable documentation as a pledgee or secured party of Securities may reasonably request in connection with a pledge or
transfer of the Securities. 

  
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 4.2 Integration. The Company shall not, and shall use its reasonable
best efforts to ensure that no Affiliate of the Company shall, sell, offer for sale or solicit offers to buy or otherwise negotiate in respect of any security (as defined in Section 2 of the 1933 Act) that would be integrated with the offer or
sale of the Securities in a manner that would require the registration under the 1933 Act of the sale of the Securities to the Subscribers or that would be integrated with the offer or sale of the Securities for purposes of the rules and regulations
of the Principal Market. 
 4.3 Reservation and Listing of Securities. So long as any Subscriber owns any Warrants,
the Company shall take all action necessary to at all times after the date hereof have authorized, and reserved for the purpose of issuance, no less than 100% of the number of shares of Common Stock issuable upon exercise of the Warrants then
outstanding (without taking into account any limitations on the exercise of the Warrants set forth in the Warrants). 
 4.4
Form D and Blue Sky. The Company shall file a Form D with respect to the Securities as required under Regulation D. The Company shall, on or before the Closing Date, take such action as the Company shall reasonably determine is necessary in
order to obtain an exemption for, or to, qualify the Securities for sale to the Subscribers at the Closing pursuant to this Agreement under applicable securities or “Blue Sky” laws of the states of the United States (or to obtain an
exemption from such qualification), and shall provide evidence of any such action so taken to the Subscribers on or prior to the Closing Date. Without limiting any other obligation of the Company under this Agreement, the Company shall timely make
all filings and reports relating to the offer and sale of the Securities required under all applicable securities laws (including, without limitation, all applicable federal securities laws and all applicable “Blue Sky” laws), and the
Company shall comply with all applicable federal, state and local laws, statutes, rules, regulations and the like relating to the offering and sale of the Securities to the Subscribers. 

4.5 Indemnification. In consideration of each Subscriber’s execution and delivery of the Transaction Documents and
acquiring the Securities thereunder and in addition to all of the Company’s other obligations under the Transaction Documents, the Company shall defend, protect, indemnify and hold harmless each Subscriber and each other holder of the Warrants
and all of their shareholders, partners, members, officers, directors, employees and investors and any of the foregoing Persons’ agents or other representatives (including, without limitation, those retained in connection with the transactions
contemplated by this Agreement) (collectively, the “Indemnitees”) from and against any and all actions, causes of action, suits, claims, losses, costs, penalties, fees, liabilities and damages, and expenses in connection therewith
(irrespective of whether any such Indemnitee is a party to the action for which indemnification hereunder is sought), and including reasonable attorneys’ fees and disbursements (the “Indemnified Liabilities”), incurred by any
Indemnitee as a result of, or arising out of, or relating to (a) any misrepresentation or breach of any representation or warranty made by the Company in the Transaction Documents, (b) any breach of any covenant, agreement or obligation of
the Company contained in the Transaction Documents, or (c) any cause of action, suit or claim brought or made against such Indemnitee by a third party (including for these purposes a derivative action brought on behalf of the Company) and
arising out of or resulting from (i) the execution, delivery, performance or enforcement of the Transaction Documents, or (ii) the status of such Subscriber as an investor in the Company pursuant to the transactions contemplated by the
Transaction Documents. For the avoidance of doubt, clauses (a) and (b) of the preceding sentence are intended 

  
 12 

 
to apply, and shall apply, to direct claims asserted by any Subscriber against the Company as well as any third party claims asserted by an Indemnitee (other than a Subscriber) against the
Company. To the extent that the foregoing undertaking by the Company may be unenforceable for any reason, the Company shall make the maximum contribution to the payment and satisfaction of each of the Indemnified Liabilities which is permissible
under applicable law. NOTWITHSTANDING ANYTHING TO THE CONTRARY IN ANY TRANSACTION DOCUMENT, THE COMPANY SHALL HAVE NO OBLIGATION TO ANY INDEMNITEE HEREUNDER WITH RESPECT TO (I) ANY INDEMNIFIED LIABILITIES TO THE EXTENT SUCH INDEMNIFIED
LIABILITIES ARISE FROM THE GROSS NEGLIGENCE OR WILLFUL MISCONDUCT, AS DETERMINED BY A COURT OF COMPETENT JURISDICTION IN A FINAL ORDER SUBJECT TO NO FURTHER APPEAL, OF THAT INDEMNITEE OR ANY OF ITS AFFILIATES OR (II) ANY SPECIAL, PUNITIVE OR
CONSEQUENTIAL DAMAGES RELATING TO ANY TRANSACTION DOCUMENT OR ARISING OUT OF ITS ACTIVITIES IN CONNECTION HEREWITH OR THEREWITH (WHETHER BEFORE OR AFTER THE CLOSING DATE). 

4.6 Waiver of Adjustment to Existing Warrants. The Subscribers hereby waive, solely in respect of the issuance of
Warrants contemplated by this Agreement, their respective rights to adjustment of the “Exercise Price” or “Warrant Shares” under Section 3 of each Warrant to Purchase Common Stock issued on August 5, 2020 (as amended on
November 8, 2020, and as further amended on January 13, 2021). 
 ARTICLE V. 

CLOSING DELIVERABLES 

5.1 Closing Deliverables of the Company. At the Closing, the Company shall deliver to the Subscribers the following:

 (a) Representations and Warranties; Certificates. The representations and warranties of the Company shall be true
and correct in all material respects as of the date when made and as of the Closing Date as though made at that time (except for representations and warranties that speak as of a specific date which shall be true and correct as of such specified
date) and the Company shall have performed, satisfied and complied in all material respects with the covenants, agreements and conditions required by the Transaction Documents to be performed, satisfied or complied with by the Company at or prior to
the Closing Date. Such Subscriber shall have received a certificate, executed by an Interim Co-Chief Executive Officer of the Company, dated as of the Closing Date, to the foregoing effect and as to such other
matters as may be reasonably requested by such Subscriber, in the form attached hereto as Exhibit B. In addition, such Subscriber shall have received a certificate, executed by the Secretary or other applicable officer of the Company, dated
as of the Closing Date, as to the resolutions consistent with Section 3.1(a) as adopted by the Company’s Board of Directors in a form reasonably acceptable to such Subscriber and the incumbency and specimen signature of each officer of the
Company who may sign this Agreement and the other Transaction Documents, in the form attached hereto as Exhibit C. 

  
 13 

 (b) Transaction Documents. The Company shall have duly executed and
delivered to such Subscriber (i) each of the Transaction Documents to which it is a party and (ii) Warrants for such aggregate number of shares of Common Stock as is set forth across from such Subscriber’s name in column (3) of
the Schedule of Subscribers. 
 ARTICLE VI. 

MISCELLANEOUS 

6.1 Fees and Expenses. The Company shall reimburse the Designee or its designee(s) (in addition to any other expense
amounts paid to any Subscriber prior to the date of this Agreement) for all reasonable and documented actual costs and expenses incurred in connection with the transactions contemplated by the Transaction Documents (including all reasonable and
documented legal fees and disbursements in connection therewith and documentation and implementation of the transactions contemplated by the Transaction Documents) on or prior to the Closing, which amount shall be paid by the Company at the Closing.
The Company shall pay, and hold each Subscriber harmless against, any liability, loss or expense (including, without limitation, reasonable attorney’s fees and
out-of-pocket expenses) arising in connection with any claim relating to any placement agent’s fees, financial advisory fees, or broker’s commissions (other
than for any Persons engaged by any Subscriber) relating to or arising out of the transactions contemplated hereby as a result of an agreement entered into by the Company. Except as otherwise set forth in the Transaction Documents, each party to
this Agreement shall bear its own expenses in connection with the sale of the Securities to the Subscribers. 
 6.2
Entire Agreement; Amendments. This Agreement and the other Transaction Documents supersede all other prior oral or written agreements between the Subscribers, the Company, their affiliates and Persons acting on their behalf with respect to
the matters discussed herein, and this Agreement, the other Transaction Documents and the instruments referenced herein and therein contain the entire understanding of the parties with respect to the matters covered herein and therein and, except as
specifically set forth herein or therein, neither the Company nor any Subscriber makes any representation, warranty, covenant or undertaking with respect to such matters. No provision of this Agreement may be amended other than by an instrument in
writing signed by the Company and the Required Holders, and any amendment to this Agreement made in conformity with the provisions of this Section 6.2 shall be binding on all Subscribers and holders of Warrants. No
provision hereof may be waived other than by an instrument in writing signed by the party against whom enforcement is sought. No such amendment shall be effective to the extent that it applies to less than all of the holders of Warrants then
outstanding. The Company has not, directly or indirectly, made any agreements with any Subscribers relating to the terms or conditions of the transactions contemplated by the Transaction Documents except as set forth in the Transaction Documents.
Without limiting the foregoing, the Company confirms that, except as set forth in this Agreement and the Financing Agreement, no Subscriber has made any commitment or promise or has any other obligation to provide any financing to the Company or
otherwise. No consideration shall be offered or paid to any Person to amend or consent to a waiver or modification of any provision of any of the Transaction Documents unless the same consideration (other than the reimbursement of legal fees) also
is offered to all of the parties to the Transaction Documents or holders of the Warrants, as the case may be. 

  
 14 

 6.3 Notices. Any notices, consents, waivers or other communications
required or permitted to be given under the terms of this Agreement must be in writing and will be deemed to have been delivered: (a) upon delivery, when delivered personally; (b) upon confirmation of delivery, when sent by electronic
mail; or (c) upon delivery or refusal of delivery when sent via a nationally recognized overnight delivery service, in each case properly addressed to the party to receive the same. The addresses, facsimile numbers and email addresses for such
communications shall be: 
  

			
	 If to the Company:
	  	 TherapeuticsMD, Inc.

951 Yamato Road, Suite 220
 Boca
Raton, FL 33431
 Attention: General Counsel

		
	 With a copy (for information purposes only) to:
	  	 DLA Piper LLP (US)

200 South Biscayne Boulevard

Suite 2500
 Miami, FL 33131

Attention: Joshua M. Samek, Esq.

		
	 If to a Subscriber:
	  	 To its address set forth on the Schedule of Subscribers, with copies to such Subscriber’s representatives as
set forth on the Schedule of Subscribers.

		
	 With a copy (for information purposes only) to:
	  	 Proskauer Rose LLP

Eleven Times Square
 New York, NY
10036
 Attention: Frederic L. Ragucci, Esq. and Michael E. Ellis, Esq.

 or such other address as may be designated in writing hereafter, in the same manner, by such Person by two
(2) Business Days’ prior notice to the other party in accordance with this Section 6.3. Written confirmation of receipt (i) given by the recipient of such notice, consent, waiver or other communication, or
(ii) provided by a courier or overnight courier service shall be rebuttable evidence of personal service or receipt from a nationally recognized overnight delivery service in accordance with clause (a) or (c) above, respectively. 

6.4 Construction. The headings herein are for convenience only, do not constitute a part of this Agreement and shall
not be deemed to limit or affect any of the provisions hereof. No specific representation or warranty shall limit the generality or applicability of a more general representation or warranty. The parties agree that each of them and/or their
respective counsel has reviewed and had an opportunity to revise the Transaction Documents and, therefore, the normal rule of construction to the effect that any ambiguities are to be resolved against the drafting party shall not be employed in the
interpretation of the Transaction Documents or any amendments hereto. 
 6.5 Successors and Assigns. This Agreement
shall be binding upon and inure to the benefit of the parties and their successors and permitted assigns. The Company may not assign this Agreement or any rights or obligations hereunder without the prior written consent of the Subscribers, except
in connection with a Fundamental Transaction (as defined in the Warrant). Any Subscriber may assign its rights under this Agreement to any Person to whom such Subscriber 

  
 15 

 
assigns or transfers any Warrants, provided such transferee (i) agrees in writing in favor of the Company to be bound, with respect to the transferred Warrants, by the provisions hereof and
of the applicable Transaction Documents that apply to the “Subscribers” and (ii) is not a Disqualified Institution (as defined in the Financing Agreement). Notwithstanding anything to the contrary herein, Securities may be pledged to
any Person in connection with a bona fide margin account or other loan or financing arrangement secured by such Securities. 

6.6 No Third-Party Beneficiaries. This Agreement is intended for the benefit of the parties hereto and their respective
successors and permitted assigns and is not for the benefit of, nor may any provision hereof be enforced by, any other Person, except that each Indemnitee is an intended third party beneficiary of Section 4.5 and may
enforce the provisions of such Sections directly against the parties with obligations thereunder. 
 6.7 Governing Law;
Venue; Waiver of Jury Trial. This Agreement and the Warrants shall be governed by and construed and enforced in accordance with, and all questions concerning the construction, validity, interpretation and performance of this Agreement and the
Warrants shall be governed by the internal laws of the State of New York, without giving effect to any choice of law or conflict of law provision or rule (whether of the State of New York or any other jurisdictions) that would cause the application
of the laws of any jurisdictions other than the State of New York (except for matters governed by corporate law in the State of Nevada). The Company, each Subscriber and each holder of a Warrant, by acceptance thereof, agrees that all legal
proceedings concerning the interpretations, enforcement and defense of the transactions contemplated by this Agreement and the Warrant (whether brought against any such party or its respective affiliates, directors, officers, stockholders, employees
or agents) shall be commenced exclusively in the state and federal courts sitting in the City of New York, Borough of Manhattan. The Company, each Subscriber and each holder of a Warrant, by acceptance thereof, hereby irrevocably submits to the
exclusive jurisdiction of the state and federal courts sitting in the City of New York, Borough of Manhattan for the adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated hereby or discussed herein
(including with respect to the enforcement of this Agreement or a Warrant) and hereby irrevocably waives and agrees not to assert in any suit, action or proceeding, any claim that it is not personally subject to the jurisdiction of any such court,
that such suit, action or proceeding is brought in an inconvenient forum or that the venue of such suit, action or proceeding is improper. THE COMPANY, EACH SUBSCRIBER AND EACH HOLDER OF A WARRANT, BY ACCEPTANCE THEREOF, HEREBY IRREVOCABLY WAIVES
ANY RIGHT IT MAY HAVE TO, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER OR IN CONNECTION WITH OR ARISING OUT OF THIS AGREEMENT, A WARRANT OR ANY TRANSACTION CONTEMPLATED HEREBY OR THEREBY. 

6.8 Survival. The representations, warranties, agreements and covenants contained herein shall survive the Closing and
the delivery and/or exercise of the Warrants, as applicable. 
 6.9 Execution. This Agreement may be executed in two
or more counterparts, all of which when taken together shall be considered one and the same agreement and shall become effective when counterparts have been signed by each party and delivered to the other party, it being understood that both parties
need not sign the same counterpart. In the event that any signature is 

  
 16 

 
delivered by facsimile transmission or by an e-mail which contains a portable document format (.pdf) filed of an executed signature page, such signature
page shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) the same with the same force and effect as if such signature page were an original thereof. 

6.10 Severability. If any provision of a Transaction Document is prohibited by law or otherwise determined to be
invalid or unenforceable by a court of competent jurisdiction, the provision that would otherwise be prohibited, invalid, or unenforceable shall be deemed amended to apply to the broadest extent that it would be valid and enforceable, and the
invalidity or unenforceability of such provision shall not affect the validity of the remaining provisions of the Transaction Document so long as the Transaction Document as so modified continues to express, without material change, the original
intentions of the parties as to the subject matter hereof or thereof and the prohibited nature, invalidity or unenforceability of the provision(s) in question does not substantially impair the respective expectations or reciprocal obligations of the
parties or the practical realization of the benefits that would otherwise be conferred upon the parties. The parties will endeavor in good faith negotiations to replace the prohibited, invalid, or unenforceable provision(s) with a valid
provision(s), the effect of which comes as close as possible to that of the prohibited, invalid or unenforceable provision(s). 

6.11 Rescission and Withdrawal Right. Notwithstanding anything to the contrary contained in (and without limiting any
similar provisions of) the Transaction Documents, whenever any Subscriber exercises a right, election, demand or option under a Transaction Document and the Company does not timely perform its related obligations within the periods therein provided,
then such Subscriber may rescind or withdraw, in its sole discretion from time to time upon written notice to the Company, any relevant notice, demand or election in whole or in part without prejudice to its future actions and rights. 

6.12 Remedies. In addition to being entitled to exercise all rights provided herein or granted by law, including
recovery of damages, the Company, each Subscriber and each holder of a Warrant, by acceptance thereof, will be entitled to specific performance under the Transaction Documents. Any Person having any rights under any provision of any Transaction
Document shall be entitled to enforce such rights specifically (without posting a bond or other security), to recover damages by reason of any breach of any provision of the Transaction Document and to exercise all other rights granted by law.
Furthermore, the Company, each Subscriber and each holder of a Warrant, by acceptance thereof, recognize that in the event that it fails to perform, observe, or discharge any or all of its obligations under the Transaction Documents, any remedy at
law may prove to be inadequate relief to the other parties. Each of such parties therefore agrees that the other parties shall be entitled to seek specific performance and/or temporary, preliminary and permanent injunctive or other equitable relief
from any court of competent jurisdiction in any such case without the necessity of showing economic loss and without any bond or other security being required. 

6.13 Payment Set Aside. To the extent that the Company makes a payment or payments to any Subscriber hereunder or
pursuant to any of the other Transaction Documents or any Subscriber enforces or exercises its rights hereunder or thereunder, and such payment or payments or the proceeds of such enforcement or exercise or any part thereof are subsequently
invalidated, declared 

  
 17 

 
to be fraudulent or preferential, set aside, recovered from, disgorged by or are required to be refunded, repaid or otherwise restored to the Company or any Company Subsidiary by a trustee,
receiver or any other person under any law (including, without limitation, any bankruptcy law, state or federal law, common law or equitable cause of action), then to the extent of any such restoration the obligation or part thereof originally
intended to be satisfied shall be revived and continued in full force and effect as if such payment had not been made or such enforcement or setoff had not occurred. 

6.14 Further Assurances. The Company, each Subscriber and each holder of a Warrant, by acceptance thereof, shall do and
perform, or cause to be done and performed, all such further acts and things, and shall execute and deliver all such other agreements, certificates, instruments and documents, as any other party may reasonably request in order to carry out the
intent and accomplish the purposes of this Agreement and the consummation of the transactions contemplated hereby. 
 6.15
Replacement of Securities. If any certificate or instrument evidencing any Securities is mutilated, lost, stolen or destroyed, the Company shall issue or cause to be issued in exchange and substitution for and upon cancellation thereof, or in
lieu of and substitution therefor, a new certificate or instrument, but only upon receipt of evidence reasonably satisfactory to the Company of such loss, theft or destruction and customary and reasonable indemnity, if requested. The applicants for
a new certificate or instrument under such circumstances shall also pay any reasonable third-party costs associated with the issuance of such replacement Securities. 

[REMAINDER OF PAGE INTENTIONALLY LEFT BLANK 

SIGNATURE PAGES FOLLOW] 

  
 18 

 IN WITNESS WHEREOF, the Subscriber and the Company have caused their
respective signature page to this Agreement to be duly executed as of the date first written above. 
  

			
	 THERAPEUTICSMD, INC.

		
	 By:
	 	 /s/ Marlan Walker

		 	 Name: Marlan Walker

		 	 Title: General Counsel and Secretary

 [Signature Page to Subscription Agreement] 

  
 19 

 IN WITNESS WHEREOF, the Subscriber and the Company have caused their
respective signature page to this Agreement to be duly executed as of the date first written above. 
  

			
	 SIXTH STREET SPECIALTY LENDING, INC.

		
	 By:
	 	 /s/ Joshua Easterly

		 	 Name: Joshua Easterly

		 	 Title: Chief Executive Officer

	
	TOP IV TALENTS, LLC
		
	 By:
	 	 /s/ Joshua Peck

		 	 Name: Joshua Peck

		 	 Title: Vice President

	
	TAO TALENTS, LLC
		
	 By:
	 	 /s/ Joshua Peck

		 	 Name: Joshua Peck

		 	 Title: Vice President

 [Signature Page to Subscription Agreement] 

  
 20 

 SCHEDULE OF SUBSCRIBERS 

 

							
	(1)	  	(2)	  	(3)	  	(4)
	Subscriber	  	 Address and Facsimile

Number
	  	 Number of

Warrant
 Shares
	  	 Legal Representative’s

Address and Facsimile Number

	 Sixth Street Specialty

Lending, Inc.
	  	 2100 McKinney Ave,

Suite 1500
 Dallas Texas 75201

Attn: Joshua Peck;
 Sixth Street
Legal
  
	  	18,750	  	 Proskauer Rose LLP

Eleven Times Square
 New York, New
York 10036
 Attention: Frederic L. Ragucci and Michael E. Ellis

	 TOP IV Talents, LLC
	  	 2100 McKinney Ave,

Suite 1500
 Dallas Texas 75201

Attn: Joshua Peck;
 Sixth Street
Legal
  
	  	31,250	  	 Proskauer Rose LLP

Eleven Times Square
 New York, New
York 10036
 Attention: Frederic L. Ragucci and Michael E. Ellis

	 TAO Talents, LLC
	  	 2100 McKinney Ave,

Suite 1500
 Dallas Texas 75201

Attn: Joshua Peck;
 Sixth Street
Legal
	  	75,000	  	 Proskauer Rose LLP

Eleven Times Square
 New York, New
York 10036
 Attention: Frederic L. Ragucci and Michael E. Ellis

  
 21 

 EXHIBIT A 

Warrants 
 (See attached)

  
 22 

 NEITHER THE ISSUANCE AND SALE OF THE SECURITIES REPRESENTED BY THIS WARRANT NOR THE
SECURITIES INTO WHICH THESE SECURITIES ARE EXERCISABLE HAVE BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR APPLICABLE STATE SECURITIES LAWS. THE SECURITIES MAY NOT BE OFFERED FOR SALE, SOLD, TRANSFERRED OR ASSIGNED IN THE ABSENCE
OF (A) AN EFFECTIVE REGISTRATION STATEMENT FOR THE SECURITIES UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR (B) AN OPINION OF COUNSEL SELECTED BY THE HOLDER, IN A FORM REASONABLY SATISFACTORY TO THE COMPANY, THAT REGISTRATION IS NOT
REQUIRED UNDER SAID ACT. NOTWITHSTANDING THE FOREGOING, THE SECURITIES MAY BE PLEDGED IN CONNECTION WITH A BONA FIDE MARGIN ACCOUNT OR OTHER LOAN OR FINANCING ARRANGEMENT SECURED BY THE SECURITIES. 

THIS WARRANT IS ONE OF THE WARRANTS TO PURCHASE COMMON STOCK ISSUED PURSUANT TO THAT CERTAIN SUBSCRIPTION AGREEMENT, DATED AS OF OCTOBER 28, 2022, BY
AND AMONG THE COMPANY AND THE INVESTORS REFERRED TO THEREIN. ANY HOLDER OF THIS WARRANT TAKES SUCH WARRANT SUBJECT TO THE TERMS AND CONDITIONS OF SUCH SUBSCRIPTION AGREEMENT AND, BY ITS ACCEPTANCE HEREOF, AGREES TO ABIDE BY THE TERMS AND CONDITIONS
THEREOF NOTWITHSTANDING ANYTHING TO THE CONTRARY SET FORTH HEREIN. 
 THERAPEUTICSMD, INC. 

WARRANT TO PURCHASE COMMON STOCK 

Warrant No.: 
 Number of Shares of Common Stock: 

Date of Issuance: October 28, 2022 (“Issuance Date”) 

TherapeuticsMD, Inc., a Nevada corporation (the “Company”), hereby certifies that, for good and valuable consideration, the
receipt and sufficiency of which are hereby acknowledged,                 , the registered holder hereof or its permitted assigns (the “Holder”), is
entitled, subject to the terms set forth below, to purchase from the Company, at the Exercise Price (as defined below) then in effect, at any time or times on or after the Issuance Date, but not after 11:59 p.m., New York time, on the Expiration
Date, (as defined below),                 fully paid nonassessable shares of Common Stock, subject to adjustment as provided herein (the “Warrant
Shares”). Except as otherwise defined herein, capitalized terms in this Warrant to Purchase Common Stock (including any Warrants to Purchase Common Stock issued in exchange, transfer or replacement hereof, this “Warrant”),
shall have the meanings set forth in Section 16. This Warrant is one of the Warrants to purchase Common Stock (the “Lender Warrants”) issued pursuant to Section 2.1 of that certain Subscription Agreement, dated as of
October 28, 2022 (the “Subscription Date”), by and among the Company and the investors (the “Subscribers”) referred to therein (the “Subscription Agreement”). Capitalized terms used herein and
not otherwise defined shall have the definitions ascribed to such terms in the Subscription Agreement. 
 1. EXERCISE OF
WARRANT. 
 (a) Mechanics of Exercise. Subject to the terms and conditions hereof (including, without
limitation, the limitations set forth in Section 1(e)), this Warrant may be exercised by the Holder at any time or times on or after the Issuance Date, in whole or in part, by (i) delivery of a written notice, in the form attached hereto
as Exhibit A (the “Exercise Notice”), of the Holder’s election to exercise this Warrant and (ii) (A) payment to the Company of an amount equal to the applicable Exercise Price multiplied by the number of Warrant
Shares as to which this Warrant is being exercised (the “Aggregate Exercise Price”) in cash by wire transfer of immediately available funds to an account designated in writing by the Company or (B) by notifying the Company in
writing that this Warrant is being exercised pursuant to a Cashless Exercise (as defined in Section 1(c)). No ink-original Exercise Notice shall be required, nor shall any medallion guarantee (or other
type of guarantee or notarization) of any Exercise Notice be required, provided that the Company shall have no liability to the Holder for honoring a non-medallion guaranteed Exercise Notice that the Company
reasonably believes to be genuine. The registered Holder shall not be required to 

  
 23 

 
deliver the original Warrant in order to effect an exercise hereunder. Execution and delivery of the Exercise Notice with respect to less than all of the Warrant Shares shall have the same effect
as cancellation of the original Warrant and issuance of a new Warrant evidencing the right to purchase the remaining number of Warrant Shares. On or before the first (1st) Trading Day following
the Trading Day on which the Holder has delivered an Exercise Notice and the Aggregate Exercise Price (or notice of a Cashless Exercise) to the Company (for purposes of this Warrant, if an Exercise Notice is delivered to the Company on a day that is
not a Trading Day, such Exercise Notice shall be deemed to have been delivered on the first Trading Day following the day of actual delivery), the Company shall transmit by electronic mail an acknowledgment of confirmation of receipt of the Exercise
Notice to the Holder. On or before the earlier of (i) the second (2nd) Trading Day and (ii) the number of Trading Days comprising the Standard Settlement Period, in each case, following
the date on which the Holder has delivered the Exercise Notice and the Aggregate Exercise Price (or notice of a Cashless Exercise) to the Company (a “Share Delivery Date”), the Company shall (X) provided that the Company’s
transfer agent (the “Transfer Agent”) is participating in The Depository Trust Company (“DTC”) Fast Automated Securities Transfer Program and (A) the Warrant Shares are subject to an effective resale
registration statement in favor of the Holder and the Holder has delivered to the Company a representation that such Warrant Shares have been sold pursuant to such registration statement or (B) if exercised via Cashless Exercise, at a time when
Rule 144 would be available for immediate resale of the Warrant Shares by the Holder, and the Holder has delivered to the Company a representation that such Warrant Shares have been sold pursuant to Rule 144, credit such aggregate number of Warrant
Shares to which the Holder is entitled pursuant to such exercise to the Holder’s or its designee’s balance account with DTC through its Deposit / Withdrawal At Custodian system, or (Y) if (A) the Transfer Agent is not participating in
the DTC Fast Automated Securities Transfer Program or (B) the Warrant Shares are not subject to an effective resale registration statement in favor of the Holder or the Holder has not delivered to the Company a representation that such Warrant
Shares have been sold pursuant to such registration statement and, if exercised via Cashless Exercise, at a time when Rule 144 would not be available for immediate resale of the Warrant Shares by the Holder or the Holder has not delivered to the
Company a representation that such Warrant Shares have been sold pursuant to such registration statement, (i) issue and dispatch by overnight courier to the address as specified in the Exercise Notice, a certificate, registered in the
Company’s share register in the name of the Holder or its designee and bearing such restrictive legends as the Company deems necessary, for the number of Warrant Shares to which the Holder is entitled pursuant to such exercise, or
(ii) issue and dispatch by electronic mail to the address as specified in the Exercise Notice, evidence of book entry, registered in the Company’s share register in the name of the Holder or its designee and bearing such restrictive
legends as the Company deems necessary, for the number of Warrant Shares to which the Holder is entitled pursuant to such exercise. The Company shall be responsible for all fees and expenses of the Transfer Agent and all fees and expenses with
respect to the issuance of Warrant Shares via DTC, if any, including without limitation for same day processing. Upon delivery of the Exercise Notice and the Aggregate Exercise Price (or notice of a Cashless Exercise), the Holder shall be deemed for
all corporate purposes to have become the holder of record of the Warrant Shares with respect to which this Warrant has been exercised, irrespective of the date such Warrant Shares are credited to the Holder’s DTC account or the date of
delivery of the certificates or book entry evidence evidencing such Warrant Shares, as the case may be. If this Warrant is submitted in connection with any exercise pursuant to this Section 1(a) and the number of Warrant Shares represented by
this Warrant submitted for exercise is greater than the number of Warrant Shares being acquired upon an exercise, then the Company shall as soon as practicable and in no event later than five (5) Trading Days after any exercise and at its own
expense, issue a new Warrant (in accordance with Section 6(d)) representing the right to purchase the number of Warrant Shares issuable immediately prior to such exercise under this Warrant, less the number of Warrant Shares with respect to
which this Warrant is exercised. No fractional Warrant Shares are to be issued upon the exercise of this Warrant, but rather the number of Warrant Shares to be issued shall be rounded to the nearest whole number. The Company shall pay any and all
taxes which may be payable with respect to the issuance and delivery of Warrant Shares upon exercise of this Warrant. 

(b) Exercise Price. For purposes of this Warrant, “Exercise Price” means $0.01, subject to adjustment
as provided herein. 
 (c) Cashless Exercise. Notwithstanding anything contained herein to the contrary, the Holder
may, in its sole discretion, exercise this Warrant in whole or in part and, in lieu of making the cash payment otherwise contemplated to be made to the Company upon such exercise in payment of the Aggregate Exercise Price, elect instead to receive
upon such exercise the “Net Number” of shares of Common Stock determined according to the following formula (a “Cashless Exercise”): 

Net Number = (A x B) - (A x C) 

              B 

  
 24 

 For purposes of the foregoing formula: 

 

			
	 A=
	  	 the total number of shares with respect to which this Warrant is then being exercised.

		
	 B=
	  	 as applicable: (i) the Weighted Average Price of the Common Stock on the Trading Day immediately preceding the date of
the applicable Exercise Notice if such Exercise Notice is (1) both executed and delivered pursuant to Section 1(a) hereof on a day that is not a Trading Day or (2) both executed and delivered pursuant to Section 1(a) hereof on a
Trading Day prior to the opening of “regular trading hours” (as defined in Rule 600(b)(68) of Regulation NMS promulgated under the federal securities laws) on such Trading Day, (ii) at the option of the Holder indicated in the
Exercise Notice, either (x) the Weighted Average Price of the Common Stock on the Trading Day immediately preceding the date of the applicable Exercise Notice, or (y) the Weighted Average Price of the Common Stock on the Trading Day of the
applicable Exercise Notice if such Exercise Notice is executed and delivered during “regular trading hours” on a Trading Day pursuant to Section 1(a) hereof, or (iii) the Weighted Average Price of the Common Stock on the date of
the applicable Exercise Notice if the date of such Exercise Notice is a Trading Day and such Exercise Notice is both executed and delivered pursuant to Section 1(a) hereof after the close of “regular trading hours” on such Trading
Day.

		
	 C=
	  	 the Exercise Price then in effect for the applicable Warrant Shares at the time of such exercise.

 For purposes of Rule 144(d) promulgated under the 1933 Act, as in effect on the date
hereof, the Company hereby acknowledges and agrees that the Warrant Shares issued in a Cashless Exercise shall be deemed to have been acquired by the Holder, and the holding period for the Warrant Shares shall be deemed to have commenced, on the
date this Warrant was last acquired by such Holder prior to such Cashless Exercise. The Company agrees not to take any position contrary to this Section 1(c). 

(d) Disputes. In the case of a dispute as to the determination of the Exercise Price or the arithmetic calculation of
the Warrant Shares, the Company shall promptly issue to the Holder the number of Warrant Shares that are not disputed and resolve such dispute in accordance with Section 11. 

(e) Beneficial Ownership Limitations on Exercises. Notwithstanding anything to the contrary contained herein, the
Company shall not effect the exercise of any portion of this Warrant, and the Holder shall not have the right to exercise any portion of this Warrant, and any such exercise shall be null and void and treated as if never made, to the extent that
after giving effect to such exercise, the Holder together with the other Attribution Parties collectively would beneficially own in excess of 4.99% (the “Maximum Percentage”) of the number of shares of Common Stock outstanding
immediately after giving effect to such exercise. For purposes of the foregoing sentence, the aggregate number of shares of Common Stock beneficially owned by the Holder and the other Attribution Parties shall include the number of shares of Common
Stock held by the Holder and all other Attribution Parties plus the number of shares of Common Stock issuable upon exercise of this Warrant with respect to which the determination of such sentence is being made, but shall exclude the number of
shares of Common Stock which would be issuable upon (A) exercise of the remaining, unexercised portion of this Warrant beneficially owned by the Holder or any of the other Attribution Parties and (B) exercise or conversion of the
unexercised or unconverted portion of any other securities of the Company (including, without limitation, any convertible notes or convertible preferred stock or warrants, including the other Lender Warrants) beneficially owned by the Holder or any
other Attribution Party subject to a limitation on conversion or exercise analogous to the limitation contained in this Section 1(e). For purposes of this Section 1(e), beneficial ownership shall be calculated in accordance with
Section 13(d) of the Securities Exchange Act of 1934, as amended (the “1934 Act”). For purposes of determining the number of outstanding shares of Common Stock the Holder may acquire upon the exercise of this Warrant without
exceeding the Maximum Percentage, the Holder may rely on the number of outstanding shares of Common Stock as reflected in (x) the Company’s most recent Annual Report on Form 10-K, Quarterly Report on
Form 10-Q, Current Report on Form 8-K or other public filing with the Securities and Exchange Commission (the “SEC”), as the case may be, (y) a
more recent public 

  
 25 

 
announcement by the Company or (z) any other written notice by the Company or the Transfer Agent setting forth the number of shares of Common Stock outstanding (the “Reported
Outstanding Share Number”). If the Company receives an Exercise Notice from the Holder at a time when the actual number of outstanding shares of Common Stock is less than the Reported Outstanding Share Number, the Company shall
(i) notify the Holder in writing of the number of shares of Common Stock then outstanding and, to the extent that such Exercise Notice would otherwise cause the Holder’s beneficial ownership, as determined pursuant to this
Section 1(e), to exceed the Maximum Percentage, the Holder must notify the Company of a reduced number of Warrant Shares to be purchased pursuant to such Exercise Notice (the number of shares by which such purchase is reduced, the
“Reduction Shares”) and (ii) as soon as reasonably practicable, the Company shall return to the Holder any Exercise Price paid by the Holder for the Reduction Shares. For any reason at any time, upon the written or oral request
of the Holder, the Company shall within one (1) Trading Day confirm orally and in writing or by electronic mail to the Holder the number of shares of Common Stock then outstanding. The number of outstanding shares of Common Stock shall be
determined after giving effect to the conversion or exercise of securities of the Company, including this Warrant, by the Holder and any other Attribution Party since the date as of which the Reported Outstanding Share Number was reported. In the
event that the issuance of shares of Common Stock to the Holder upon exercise of this Warrant results in the Holder and the other Attribution Parties being deemed to beneficially own, in the aggregate, more than the Maximum Percentage of the number
of outstanding shares of Common Stock (as determined under Section 13(d) of the 1934 Act), the number of shares so issued by which the Holder’s and the other Attribution Parties’ aggregate beneficial ownership exceeds the Maximum
Percentage (the “Excess Shares”) shall be deemed null and void and shall be cancelled ab initio, and the Holder shall not have the power to vote or to transfer the Excess Shares. As soon as reasonably practicable after the issuance
of the Excess Shares has been deemed null and void, the Company shall return to the Holder the Exercise Price paid by the Holder for the Excess Shares. Upon delivery of a written notice to the Company, the Holder may from time to time increase or
decrease the Maximum Percentage to any other percentage not in excess of 9.99% as specified in such notice; provided that (i) any such increase in the Maximum Percentage will not be effective until the sixty-first (61st) day after such notice is delivered to the Company and (ii) any such increase or decrease will apply only to the Holder and the other Attribution Parties and not to any other holder of Lender
Warrants that is not an Attribution Party of the Holder. For purposes of clarity, the shares of Common Stock issuable pursuant to the terms of this Warrant in excess of the Maximum Percentage shall not be deemed to be beneficially owned by the
Holder for any purpose including for purposes of Section 13(d) or Rule 16a-1(a)(1) of the 1934 Act. No prior inability to exercise this Warrant pursuant to this paragraph shall have any effect on the
applicability of the provisions of this paragraph with respect to any subsequent determination of exercisability. The provisions of this paragraph shall be construed and implemented in a manner otherwise than in strict conformity with the terms of
this Section 1(e) to the extent necessary to correct this paragraph or any portion of this paragraph which may be defective or inconsistent with the intended beneficial ownership limitation contained in this Section 1(e) or to make changes
or supplements necessary or desirable to properly give effect to such limitation. The limitation contained in this paragraph may not be waived and shall apply to a successor holder of this Warrant. 

2. ADJUSTMENT OF EXERCISE PRICE AND NUMBER OF WARRANT SHARES. 

(a) Adjustment Upon Subdivision or Combination of Shares of Common Stock. If the Company at any time on
or after the Subscription Date subdivides (by any stock split, stock dividend, recapitalization or otherwise) its outstanding shares of Common Stock into a greater number of shares, the Exercise Price in effect immediately prior to such subdivision
will be proportionately reduced and the number of Warrant Shares will be proportionately increased. If the Company at any time on or after the Subscription Date combines (by combination, reverse stock split or otherwise) its outstanding shares of
Common Stock into a smaller number of shares, the Exercise Price in effect immediately prior to such combination will be proportionately increased and the number of Warrant Shares will be proportionately decreased. Any adjustment under this
Section 2(a) shall become effective at the close of business on the date the subdivision or combination becomes effective. 

(b) Adjustment to Exercise Price and Number of Warrant Shares for Subsequent Issuances. In order to
prevent dilution of the purchase rights granted under this Warrant, the Exercise Price and the number of Warrant Shares issuable upon exercise of this Warrant shall be subject to adjustment from time to time as provided in this Section 2(b) (in
each case, after taking into consideration any prior adjustments pursuant to this Section 2(b) or otherwise), with any such adjustment automatically becoming effective without further action of any person required; provided, that
there shall be no adjustment to the number of Warrant Shares acquirable upon exercise of the Warrant, as provided in this Section 2(b) (an “Adjustment”), 

  
 26 

 
unless and until such Adjustment, together with any previous Adjustments to the number of Warrant Shares so acquirable which would otherwise have resulted in an Adjustment were it not for this
proviso, would require an increase or decrease of at least 5% of the total number of Warrant Shares so acquirable at the time of such Adjustment, in which event such Adjustment and all such previous Adjustments shall immediately occur. 

(i) Definitions. For purposes of this Section 2(b), the following terms shall have the following
meanings: 
 “Excluded Issuances” means any issuance or sale (or deemed issuance or sale in accordance with
Section 2(b)(iv)) by the Company after the Adjustment Date of: (a) shares of Common Stock issued upon the exercise of the Warrants; (b) shares of Common Stock issued upon the conversion or exercise of options or convertible securities
issued prior to the Adjustment Date, provided that such securities are not amended after the Adjustment Date to increase the number of shares of Common Stock issuable thereunder or to lower the exercise or conversion price thereof;
or (c) shares of Common Stock under the Company’s 2019 Stock Incentive Plan or the Company’s 2020 Employee Stock Purchase Plan. 

“Independent Financial Expert” shall mean a nationally recognized accounting, investment banking or consultant
firm, which firm does not have a material financial interest or other material economic relationship with either the Company or any of its Affiliates or the Holder or any of its Affiliates that is, in the good faith judgment of the Company’s
board of directors (the “Board”), qualified to perform the task for which it has been engaged. 

“Trading Day” shall mean a day on which trading in the shares of Common Stock (or other applicable security)
generally occurs on the principal exchange or market on which the shares of Common Stock (or other applicable security) are then listed or traded; provided that if the shares of Common Stock (or other applicable security) are not so listed or
traded, “Trading Day” means a Business Day. 
 “VWAP” shall mean, as of any date of determination,
the average per share volume-weighted average price as displayed under the heading “Bloomberg VWAP” on Bloomberg page “TXMD<equity> AQR” (or its equivalent successor if such Bloomberg page is not available) in respect of
the period from the open of trading on the relevant Trading Day until the close of trading on such Trading Day (or if such volume-weighted average price is unavailable, the market value of one share of Common Stock on such Trading Day reasonably
determined, using a volume-weighted average method, by an Independent Financial Expert appointed (and compensated by the Company) for such purpose). The VWAP will be determined without regard to after-hours trading or any other trading outside of
the regular trading session trading hours. 
 (ii) Adjustment for Common Stock Issuances. If the
Company shall, at any time or from time to time after October 28, 2022 (the “Adjustment Date”), issue or sell, or is deemed to have issued or sold, any shares of Common Stock for consideration per share less than the Exercise
Price in effect immediately prior to such issuance or sale (or deemed issuance or sale) (“Adjustment Trigger Shares”), then immediately upon such issuance or sale (or deemed issuance or sale), the Exercise Price shall be reduced to
the weighted average per share consideration received by the Company for all Adjustment Trigger Shares so issued or sold (or deemed issued or sold) from and after the Adjustment Date, as determined in good faith by the Board, and the number of
Warrant Shares will be proportionately increased. 
 (iii) Exceptions to Adjustment Upon Issuance of
Common Stock. Anything herein to the contrary notwithstanding, there shall be no adjustment to the Exercise Price or the number of Warrant Shares issuable upon exercise of this Warrant with respect to any Excluded Issuance. 

(iv) Adjustment for Certain Events. For purposes of determining the adjusted Exercise Price and number
of Warrant Shares under Section 1(a) hereof, the following shall be applicable: 
 (A) Issuance of
Options. If the Company shall, at any time or from time to time after the Adjustment Date, grant or sell any options, whether or not such options or the right to convert or exchange any convertible securities issuable upon the exercise of such
options are immediately exercisable, and the price per share (determined as provided in this 

  
 27 

 
paragraph and in Section 2(b)(iv)(C)) for which Common Stock is issuable upon the exercise of such options or upon the conversion or exchange of convertible securities issuable upon the
exercise of such options is less than the Exercise Price in effect immediately prior to the time of the granting or sale of such options, then the total maximum number of shares of Common Stock issuable upon the exercise of such options or upon
conversion or exchange of the total maximum amount of convertible securities issuable upon the exercise of such options shall be deemed to have been issued as of the date of granting or sale of such options at a price per share equal to the quotient
obtained by dividing of (a) the total amount, if any, received or receivable by the Company as consideration for the granting, sale, or exercise of all such options (which sum shall constitute the applicable consideration received for purposes
of Section 1(a)), by (b) the total maximum number of shares of Common Stock issuable upon the exercise of all such options or upon the conversion or exchange of all convertible securities issuable upon the exercise of all such options, and
the number of Warrant Shares will be proportionately increased. No further adjustment of the Exercise Price or the number of Warrant Shares shall be made upon the actual issuance of Common Stock or of convertible securities upon exercise of such
options or upon the actual issuance of Common Stock upon conversion or exchange of convertible securities issuable upon exercise of such options. 

(B) Issuance of Convertible Securities. If the Company shall, at any time or from time to time after
the Adjustment Date, grant or sell any convertible securities, whether or not the right to convert or exchange any such convertible securities is immediately exercisable, and the price per share (determined as provided in this paragraph and in
Section 2(b)(iv)(C)) for which Common Stock is issuable upon the conversion or exchange of such convertible securities is less than the Exercise Price in effect immediately prior to the time of the granting or sale of such convertible
securities, then the total maximum number of shares of Common Stock issuable upon conversion or exchange of the total maximum amount of such convertible securities shall be deemed to have been issued as of the date of granting or sale of such
convertible securities at a price per share equal to the quotient obtained by dividing (a) the total amount, if any, received or receivable by the Company as consideration for the granting, sale, or exercise of such convertible securities
(which sum shall constitute the applicable consideration received for purposes of Section 1(a)), by (b) the total maximum number of shares of Common Stock issuable upon the conversion or exchange of all such convertible securities, and the
number of Warrant Shares will be proportionately increased. No further adjustment of the Exercise Price or the number of Warrant Shares shall be made upon the actual issuance of Common Stock upon conversion or exchange of such convertible securities
or by reason of the issue or sale of convertible securities upon exercise of any options to purchase any such convertible securities for which adjustments of the Exercise Price have been made pursuant to the other provisions of this
Section 2(b)(iv). 
 (C) Calculation of Consideration Received. If the Company shall, at any
time or from time to time after the Adjustment Date, issue or sell, or is deemed to have issued or sold, any shares of Common Stock, options or convertible securities: (A) for cash, the consideration received therefor shall be deemed to be the
net amount received or receivable by the Company therefor; (B) for consideration other than cash, the amount of the consideration other than cash received or receivable by the Company shall be the fair market value of such consideration, except
where such consideration consists of marketable securities, in which case the amount of consideration received or receivable by the Company shall be the market price (as reflected on any securities exchange, quotation system or association or
similar pricing system covering such security) for such securities as of the end of business on the date of receipt of such securities; or (C) for no specifically allocated consideration in connection with an issuance or sale of other
securities of the Company, together comprising one integrated transaction, the amount of the consideration therefor shall be deemed to be the fair market value of such portion of the aggregate consideration received or receivable by the Company in
such transaction as is attributable to such shares of Common Stock, options or convertible securities, as the case may be, issued in such transaction. The net amount of any cash consideration and 

  
 28 

 
the fair market value of any consideration other than cash or marketable securities shall be determined in good faith by the Board. 

(v) Certificate as to Adjustment. 

(A) As promptly as reasonably practicable following any adjustment of the Exercise Price and/or the number of
Warrant Shares, but in any event not later than 15 Business Days thereafter, the Company shall furnish to the Holder a certificate of an executive officer setting forth in reasonable detail such adjustment and the facts upon which it is based and
certifying the calculation thereof. All calculations of Exercise Price under this Section 2(b) shall be made to the nearest cent or to the nearest one-hundredth of a share, as the case may be. 

(B) As promptly as reasonably practicable following the receipt by the Company of a written request by the
Holder, but in any event not later than 15 Business Days thereafter, the Company shall furnish to the Holder a certificate of an executive officer certifying the Exercise Price then in effect and the number of Warrant Shares or the amount, if any,
of other shares of stock, securities or assets then issuable upon exercise of the Warrant. 
 3. FUNDAMENTAL
TRANSACTIONS. In the event of a Fundamental Transaction, the Company shall make appropriate provision to ensure that (a) the purchaser (or its parent) shall assume this Warrant (with appropriate changes to the Exercise Price to take into
account the value of the securities substituted for the Common Stock so as to preserve the intrinsic spread between the fair market value of any substituted securities and the Exercise Price), or (b) Holder will thereafter have the right to
receive upon an exercise of this Warrant, in lieu of the shares of the Common Stock (or other securities, cash, assets or other property) issuable upon the exercise of this Warrant prior to such Fundamental Transaction, such securities, cash or
other assets (including warrants or other purchase or subscription rights) which the Holder would have been entitled to receive on a per share basis upon the happening of such Fundamental Transaction had this Warrant been exercised immediately prior
to such Fundamental Transaction (without regard to any limitations on the exercise of this Warrant); provided, however, that following any Fundamental Transaction, this Warrant shall only be exercisable via Cashless Exercise. The
provisions of this Section 3 shall apply similarly and equally to successive Fundamental Transactions. 
 4.
NONCIRCUMVENTION. The Company hereby covenants and agrees that the Company will not, by amendment of its Articles of Incorporation or Bylaws, or through any reorganization, transfer of assets, consolidation, merger, scheme of arrangement,
dissolution, issue or sale of securities, or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms of this Warrant, and will at all times in good faith carry out all of the provisions of this Warrant
and take all action as may be required to protect the rights of the Holder. Without limiting the generality of the foregoing, the Company (a) shall not increase the par value of any shares of Common Stock receivable upon the exercise of this
Warrant above the Exercise Price then in effect, (b) shall take all such actions as may be necessary or appropriate in order that the Company may validly and legally issue fully paid and nonassessable shares of Common Stock upon the exercise of
this Warrant, and (c) shall, so long as any of the Lender Warrants are outstanding, take all action necessary to reserve and keep available out of its authorized and unissued shares of Common Stock, solely for the purpose of effecting the
exercise of the Lender Warrants, 100% of the number of shares of Common Stock as shall from time to time be necessary to effect the exercise of the Lender Warrants then outstanding (without regard to any limitations on exercise). 

5. WARRANT HOLDER NOT DEEMED A STOCKHOLDER. Except as otherwise specifically provided herein, the Holder, solely in
such Person’s capacity as a holder of this Warrant, shall not be entitled to vote or receive dividends or be deemed the holder of capital stock of the Company for any purpose, nor shall anything contained in this Warrant be construed to confer
upon the Holder, solely in such Person’s capacity as the Holder of this Warrant, any of the rights of a stockholder of the Company or any right to vote, give or withhold consent to any corporate action (whether any reorganization, issue of
stock, reclassification of stock, consolidation, merger, conveyance or otherwise), receive notice of meetings, receive dividends or subscription rights, or otherwise, prior to the issuance to the Holder of the Warrant Shares which such Person is
then entitled to receive upon the due exercise of this Warrant. In addition, nothing contained in this Warrant shall be construed as imposing any liabilities on the 

  
 29 

 
Holder to purchase any securities (upon exercise of this Warrant or otherwise) or as a stockholder of the Company, whether such liabilities are asserted by the Company or by creditors of the
Company. 
 6. REISSUANCE OF WARRANTS. 

(a) Transfer of Warrant. If this Warrant is to be transferred, the Holder shall surrender this Warrant to the Company,
whereupon the Company will forthwith issue and deliver upon the order of the Holder a new Warrant (in accordance with Section 6(d)), registered as the Holder may request, representing the right to purchase the number of Warrant Shares being
transferred by the Holder and, if less than the total number of Warrant Shares then underlying this Warrant is being transferred, a new Warrant (in accordance with Section 6(d)) to the Holder representing the right to purchase the number of
Warrant Shares not being transferred. 
 (b) Lost, Stolen or Mutilated Warrant. Upon receipt by the Company of
evidence reasonably satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant, and, in the case of loss, theft or destruction, of any indemnification undertaking by the Holder to the Company in customary form and, in
the case of mutilation, upon surrender and cancellation of this Warrant, the Company shall execute and deliver to the Holder a new Warrant (in accordance with Section 6(d)) representing the right to purchase the Warrant Shares then underlying
this Warrant. 
 (c) Exchangeable for Multiple Warrants. This Warrant is exchangeable, upon the surrender hereof by
the Holder at the principal office of the Company, for a new Warrant or Warrants (in accordance with Section 6(d)) representing in the aggregate the right to purchase the number of Warrant Shares then underlying this Warrant, and each such new
Warrant will represent the right to purchase such portion of such Warrant Shares as is designated by the Holder at the time of such surrender; provided, however, that no Lender Warrants for fractional Warrant Shares shall be given.

 (d) Issuance of New Warrants. Whenever the Company is required to issue a new Warrant pursuant to the terms of
this Warrant, such new Warrant (i) shall be of like tenor with this Warrant, (ii) shall represent, as indicated on the face of such new Warrant, the right to purchase the Warrant Shares then underlying this Warrant (or in the case of a new
Warrant being issued pursuant to Section 6(a) or Section 6(c), the Warrant Shares designated by the Holder which, when added to the number of shares of Common Stock underlying the other new Warrants issued in connection with such issuance,
does not exceed the number of Warrant Shares then underlying this Warrant), (iii) shall have an issuance date, as indicated on the face of such new Warrant which is the same as the Issuance Date, and (iv) shall have the same rights and
conditions as this Warrant. 
 7. NOTICES. Whenever notice is required to be given under this Warrant, unless
otherwise provided herein, such notice shall be given in accordance with Section 6.3 of the Subscription Agreement. The Company will give written notice to the Holder (a) promptly following any adjustment of the Exercise Price, setting
forth in reasonable detail, and certifying, the calculation of such adjustment and (b) at least ten (10) days prior to the date on which the Company closes its books or takes a record (i) with respect to any dividend or distribution
upon the shares of Common Stock, (ii) with respect to any grants, issuances or sales of any options, convertible securities or rights to purchase stock, warrants, securities or other property, in each case pro rata to all record holders of
Common Stock, or (iii) for determining rights to vote with respect to any Fundamental Transaction, dissolution or liquidation; provided in each case that such information shall be made known to the public prior to or in conjunction with
such notice being provided to the Holder. 
 8. AMENDMENT AND WAIVER. Except as otherwise provided herein, the
provisions of this Warrant may be amended or waived and the Company may take any action herein prohibited, or omit to perform any act herein required to be performed by it, only if the Company has obtained the written consent of the Required
Holders. Any amendment or waiver by the Company and the Required Holders shall be binding on the Holder of this Warrant and all holders of the Lender Warrants. 

9. GOVERNING LAW; JURISDICTION; JURY TRIAL. This Warrant shall be governed by and construed and enforced in accordance
with, and all questions concerning the construction, validity, interpretation and performance of this Warrant shall be governed by, the internal laws of the State of New York, without giving effect to any choice of law or conflict of law provision
or rule (whether of the State of New York or any other jurisdictions) 

  
 30 

 
that would cause the application of the laws of any jurisdictions other than the State of New York. The Company hereby irrevocably submits to the exclusive jurisdiction of the state and federal
courts sitting in The City of New York, Borough of Manhattan, for the adjudication of any dispute hereunder or in connection herewith or with any transaction contemplated hereby or discussed herein, and hereby irrevocably waives, and agrees not to
assert in any suit, action or proceeding, any claim that it is not personally subject to the jurisdiction of any such court, that such suit, action or proceeding is brought in an inconvenient forum or that the venue of such suit, action or
proceeding is improper. Nothing contained herein shall be deemed to limit in any way any right to serve process in any manner permitted by law. Nothing contained herein shall be deemed or operate to preclude the Holder from bringing suit or taking
other legal action against the Company in any other jurisdiction to collect on the Company’s obligations to the Holder, to realize on any collateral or any other security for such obligations, or to enforce a judgment or other court ruling in
favor of the Holder. THE COMPANY HEREBY IRREVOCABLY WAIVES ANY RIGHT IT MAY HAVE, AND AGREES NOT TO REQUEST, A JURY TRIAL FOR THE ADJUDICATION OF ANY DISPUTE HEREUNDER OR IN CONNECTION WITH OR ARISING OUT OF THIS WARRANT OR ANY TRANSACTION
CONTEMPLATED HEREBY. 
 10. CONSTRUCTION; HEADINGS. This Warrant shall be deemed to be jointly drafted by the
Company and all of the Subscribers and shall not be construed against any Person as the drafter hereof. The headings of this Warrant are for convenience of reference and shall not form part of, or affect the interpretation of, this Warrant. 

11. DISPUTE RESOLUTION. In the case of a dispute as to the determination of the Exercise Price or the arithmetic
calculation of the Warrant Shares, the Company shall submit the disputed determinations or arithmetic calculations via electronic mail within three (3) Business Days of receipt of the Exercise Notice giving rise to such dispute, as the case may
be, to the Holder. If the Holder and the Company are unable to agree upon such determination or calculation of the Exercise Price or the Warrant Shares within three (3) Business Days of such disputed determination or arithmetic calculation
being submitted to the Holder, then the Company shall, within three (3) Business Days submit via electronic mail (a) the disputed determination of the Exercise Price, together with the Company’s and Holder’s respective
calculations, to an independent, reputable investment bank or financial services firm selected by the Holder and approved by the Company, such approval not to be unreasonably withheld, conditioned, or delayed, or (b) the disputed arithmetic
calculation of the Warrant Shares, together with the Company’s and Holder’s respective calculations, to an independent, outside accountant, selected by the Holder and approved by the Company, such approval not to be unreasonably withheld,
conditioned, or delayed. The Company shall cause the investment bank, financial services firm or accountant, as the case may be, to perform the determinations or calculations and notify the Company and the Holder of the results no later than five
(5) Business Days from the time it receives the disputed determinations or calculations. Such investment bank’s, financial services firm’s or accountant’s determination or calculation, as the case may be, shall be binding upon
all parties absent demonstrable error. The costs of such investment bank, financial services firm or accountant shall be allocated by such firm between the Company and the Holder proportionally based on such firm’s determination or calculation
and the Company’s and Holder’s respective calculations submitted to such firm. 
 12. REMEDIES, OTHER
OBLIGATIONS, BREACHES AND INJUNCTIVE RELIEF. The remedies provided in this Warrant shall be cumulative and in addition to all other remedies available under this Warrant and the other Transaction Documents, at law or in equity (including a
decree of specific performance and/or other injunctive relief), and nothing herein shall limit the right of the Holder to pursue actual damages for any failure by the Company to comply with the terms of this Warrant. The Company acknowledges that a
breach by it of its obligations hereunder will cause irreparable harm to the Holder and that the remedy at law for any such breach may be inadequate. The Company therefore agrees that, in the event of any such breach or threatened breach, the holder
of this Warrant shall be entitled, in addition to all other available remedies, to seek an injunction restraining any breach, without the necessity of showing economic loss and without any bond or other security being required. 

13. TRANSFER. This Warrant and the Warrant Shares may be offered for sale, sold, transferred, pledged or assigned
without the consent of the Company, except as may otherwise be required by Section 6.5 of the Subscription Agreement. 

14. SEVERABILITY. If any provision of this Warrant is prohibited by law or otherwise determined to be invalid or
unenforceable by a court of competent jurisdiction, the provision that would otherwise be prohibited, 

  
 31 

 
invalid or unenforceable shall be deemed amended to apply to the broadest extent that it would be valid and enforceable, and the invalidity or unenforceability of such provision shall not affect
the validity of the remaining provisions of this Warrant so long as this Warrant as so modified continues to express, without material change, the original intentions of the parties as to the subject matter hereof and the prohibited nature,
invalidity or unenforceability of the provision(s) in question does not substantially impair the respective expectations or reciprocal obligations of the parties or the practical realization of the benefits that would otherwise be conferred upon the
parties. The parties will endeavor in good faith negotiations to replace the prohibited, invalid or unenforceable provision(s) with a valid provision(s), the effect of which comes as close as possible to that of the prohibited, invalid or
unenforceable provision(s). 
 15. DISCLOSURE. Upon delivery by the Company to the Holder of any notice required to
be given in accordance with the terms of this Warrant, unless the Company has in good faith determined that the matters relating to such notice do not constitute material, nonpublic information relating to the Company or its Subsidiaries, the
Company shall contemporaneously with any such delivery publicly disclose such material, nonpublic information on a Current Report on Form 8-K or otherwise. In the event that the Company believes that any
notice required to be delivered by the Company in accordance with the terms of this Warrant contains material, nonpublic information relating to the Company or its Subsidiaries, the Company so shall indicate to the Holder contemporaneously with
delivery of such notice, and in the absence of any such indication, the Holder shall be allowed to presume that all matters relating to such notice do not constitute material, nonpublic information relating to the Company or its Subsidiaries. 

16. CERTAIN DEFINITIONS. For purposes of this Warrant, the following terms shall have the following meanings: 

(a) “1933 Act” means the Securities Act of 1933, as amended. 

(b) “Affiliate” shall have the meaning ascribed to such term in Rule 405 of the 1933 Act. 

(c) “Attribution Parties” means, collectively, the following Persons and entities: (i) any investment
vehicle, including, any funds, feeder funds or managed accounts, currently, or from time to time after the Issuance Date, directly or indirectly managed or advised by the Holder’s investment manager or any of its Affiliates or principals,
(ii) any direct or indirect Affiliates of the Holder or any of the foregoing, (iii) any Person acting or who could be deemed to be acting as a Group together with the Holder or any of the foregoing and (iv) any other Persons whose
beneficial ownership of the Common Stock would or could be aggregated with the Holder’s and the other Attribution Parties for purposes of Section 13(d) of the 1934 Act. For clarity, the purpose of the foregoing is to subject collectively
the Holder and all other Attribution Parties to the Maximum Percentage. 
 (d) “Bloomberg” means Bloomberg
Financial Markets. 
 (e) “Business Day” means any day other than Saturday, Sunday or other day on which
commercial banks in The City of New York, New York are authorized or required by law to remain closed; provided, however, for clarification, commercial banks shall not be deemed to be authorized or required by law to remain closed due
to “stay at home”, “shelter-in-place”, “non-essential employee” or any other similar orders or
restrictions or the closure of any physical branch locations at the direction of any governmental authority so long as the electronic funds transfer systems (including for wire transfers) of commercial banks in The City of New York, New York
generally are open for use by customers on such day. 
 (f) “Common Stock” means (i) the
Company’s shares of common stock, par value $0.001 per share, and (ii) any capital stock into which such Common Stock shall have been changed or any capital stock resulting from a reclassification, reorganization or recapitalization of
such Common Stock. 
 (g) “Designee” means Sixth Street Specialty Lending, Inc. 

(h) “Eligible Market” means the Principal Market, the NYSE American, The Nasdaq Global Select Market, The
Nasdaq Global Market, The Nasdaq Capital Market or The New York Stock Exchange, Inc. 
 (i) “Expiration
Date” means the date that is one hundred twenty (120) months after the Issuance Date or, if such date falls on a day other than a Business Day or on which trading does not take place on the Principal Market (a
“Holiday”), the next day that is not a Holiday. 

  
 32 

 (j) “Fundamental Transaction” means (A) that the
Company shall, directly or indirectly, including through Subsidiaries, Affiliates or otherwise, in one or more related transactions, (i) consolidate or merge with or into (whether or not the Company is the surviving corporation) another Subject
Entity, or (ii) sell, assign, transfer, convey or otherwise dispose of all or substantially all of the properties or assets of the Company, or (iii) make, or allow one or more Subject Entities to make, or allow the Company to be subject to
or have its Common Stock be subject to or party to one or more Subject Entities making, a purchase, tender or exchange offer that is accepted by the holders of at least either (x) 50% of the outstanding shares of Common Stock, (y) 50% of the
outstanding shares of Common Stock calculated as if any shares of Common Stock held by all Subject Entities making or party to, or Affiliated with any Subject Entities making or party to, such purchase, tender or exchange offer were not outstanding;
or (z) such number of shares of Common Stock such that all Subject Entities making or party to, or Affiliated with any Subject Entity making or party to, such purchase, tender or exchange offer, become collectively the beneficial owners (as
defined in Rule 13d-3 under the 1934 Act) of at least 50% of the outstanding shares of Common Stock, or (iv) consummate a stock purchase agreement or other business combination (including, without
limitation, a reorganization, recapitalization, spin-off or scheme of arrangement) with one or more Subject Entities whereby such Subject Entities, individually or in the aggregate, acquire, either (x) at
least 50% of the outstanding shares of Common Stock, (y) at least 50% of the outstanding shares of Common Stock calculated as if any shares of Common Stock held by all the Subject Entities making or party to, or Affiliated with any Subject
Entity making or party to, such stock purchase agreement or other business combination were not outstanding; or (z) such number of shares of Common Stock such that the Subject Entities become collectively the beneficial owners (as defined in
Rule 13d-3 under the 1934 Act) of at least 50% of the outstanding shares of Common Stock, or (v) reorganize, recapitalize or reclassify its Common Stock, (B) that the Company shall, directly or
indirectly, including through Subsidiaries, Affiliates or otherwise, in one or more related transactions, allow any Subject Entity individually or the Subject Entities in the aggregate to be or become the “beneficial owner” (as defined in
Rule 13d-3 under the 1934 Act), directly or indirectly, whether through acquisition, purchase, assignment, conveyance, tender, tender offer, exchange, reduction in outstanding shares of Common Stock, merger,
consolidation, business combination, reorganization, recapitalization, spin-off, scheme of arrangement, reorganization, recapitalization or reclassification or otherwise in any manner whatsoever, of either
(x) at least 50% of the aggregate ordinary voting power represented by issued and outstanding Common Stock, (y) at least 50% of the aggregate ordinary voting power represented by issued and outstanding Common Stock not held by all such
Subject Entities as of the Subscription Date calculated as if any shares of Common Stock held by all such Subject Entities were not outstanding, or (z) a percentage of the aggregate ordinary voting power represented by issued and outstanding
shares of Common Stock or other equity securities of the Company sufficient to allow such Subject Entities to effect a statutory short form merger or other transaction requiring other stockholders of the Company to surrender their shares of Common
Stock without approval of the stockholders of the Company or (C) directly or indirectly, including through Subsidiaries, Affiliates or otherwise, in one or more related transactions, the issuance of or the entering into any other instrument or
transaction structured in a manner to circumvent, or that circumvents, the intent of this definition in which case this definition shall be construed and implemented in a manner otherwise than in strict conformity with the terms of this definition
to the extent necessary to correct this definition or any portion of this definition which may be defective or inconsistent with the intended treatment of such instrument or transaction. 

(k) “Group” means a “group” as that term is used in Section 13(d) of the 1934 Act and as
defined in Rule 13d-5 thereunder. 
 (l) “Person” means an
individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization, any other entity and a government or any department or agency thereof. 

(m) “Principal Market” means The Nasdaq Stock Market LLC. 

(n) “Required Holders” means the holders of the Lender Warrants representing at least a majority of the
shares of Common Stock underlying the Lender Warrants then outstanding and shall include the Designee as long as the Designee or any of its Affiliates holds any Lender Warrants. 

(o) “Standard Settlement Period” means the standard settlement period, expressed in a number of Trading
Days, on the principal securities exchange or securities market on which the Common Stock is then traded as in effect on the date of delivery of the applicable Exercise Notice. 

(p) “Subject Entity” means any Person, Persons or Group or any Affiliate or associate of any such Person,
Persons or Group. 

  
 33 

 (q) “Subsidiary” has the meaning as set forth in the
Subscription Agreement. 
 (r) “Trading Day” means any day on which the Common Stock is traded on the
Principal Market, or, if the Principal Market is not the principal trading market for the Common Stock on such day, then on the principal securities exchange or securities market on which the Common Stock is then traded. 

(s) “Weighted Average Price” means, for any security as of any date, the dollar volume-weighted average
price for such security on the Principal Market during the period beginning at 9:30:01 a.m., New York time (or such other time as the Principal Market publicly announces is the official open of trading), and ending at 4:00:00 p.m., New York time (or
such other time as the Principal Market publicly announces is the official close of trading), as reported by Bloomberg through its “Volume at Price” function or, if the foregoing does not apply, the dollar volume-weighted average price of
such security in the over-the-counter market on the electronic bulletin board for such security during the period beginning at 9:30:01 a.m., New York time (or such other
time as such market publicly announces is the official open of trading), and ending at 4:00:00 p.m., New York time (or such other time as such market publicly announces is the official close of trading), as reported by Bloomberg, or, if no dollar
volume-weighted average price is reported for such security by Bloomberg for such hours, the average of the highest closing bid price and the lowest closing ask price of any of the market makers for such security as reported in the OTC Link or
“pink sheets” by OTC Markets Group Inc. (formerly Pink OTC Markets Inc.). If the Weighted Average Price cannot be calculated for a security on a particular date on any of the foregoing bases, the Weighted Average Price of such security on
such date shall be the fair market value as mutually determined by the Company and the Holder. If the Company and the Holder are unable to agree upon the fair market value of such security, then such dispute shall be resolved pursuant to
Section 11 with the term “Weighted Average Price” being substituted for the term “Exercise Price.” All such determinations shall be appropriately adjusted for any stock dividend, stock split, stock combination,
reclassification or other similar transaction during the applicable calculation period. 
 [Signature Page Follows] 

  
 34 

 IN WITNESS WHEREOF, the Company has caused this Warrant to Purchase
Common Stock to be duly executed as of the Issuance Date set out above in accordance with the terms of the Warrant. 
  

			
	THERAPEUTICSMD, INC.
		
	 By:
	 	  

	 Name:
	 	
	 Title:
	 	

  
 35 

 EXHIBIT A 

EXERCISE NOTICE 
 TO BE
EXECUTED BY THE REGISTERED HOLDER TO EXERCISE THIS 
 WARRANT TO PURCHASE COMMON STOCK 

THERAPEUTICSMD, INC. 

The undersigned holder hereby exercises the right to purchase _________________ of the shares of Common Stock
(“Warrant Shares”) of TherapeuticsMD, Inc., a Nevada corporation (the “Company”), evidenced by the attached Warrant to Purchase Common Stock (the “Warrant”). Capitalized terms used herein and not
otherwise defined shall have the respective meanings set forth in the Warrant. 
 1. Form of Exercise Price. The Holder
intends that payment of the Exercise Price shall be made as: 
 ____________ a “Cash Exercise” with respect to
_________________ Warrant Shares; and/or 
 ____________ a “Cashless Exercise” with respect to _______________ Warrant
Shares, resulting in a delivery obligation of the Company to the Holder of __________ shares of Common Stock representing the applicable Net Number. 

2. Payment of Exercise Price. In the event that the holder has elected a Cash Exercise with respect to some or all of the
Warrant Shares to be issued pursuant hereto, the holder shall pay the Aggregate Exercise Price in the sum of $___________________ to the Company in accordance with the terms of the Warrant. 

3. Delivery of Warrant Shares. The Company shall deliver to the holder __________ Warrant Shares in accordance with the terms
of the Warrant as follows, subject to Section 1(a) of the Warrant. 
  

			
	
                       
 
	  	 Warrant Shares have been sold pursuant to an effective resale registration statement and should be credited to the
Holder’s or its designee’s balance account with DTC through its Deposit / Withdrawal At Custodian system pursuant to the information that accompanies this notice; and/or

	
                       
 
	  	  
 Warrant Shares acquired via Cashless Exercise have
been sold pursuant to Rule 144 and the Holder has delivered to the Company representations from the Holder and the Holder’s broker indicating such and such Warrant Shares should be credited to the Holder’s or its designee’s balance
account with DTC through its Deposit / Withdrawal At Custodian system pursuant to the information that accompanies this notice; and/or

	
                       
 
	  	  
 Warrant Shares represented by a certificate or
evidence of book entry should be sent to the Holder or its designee at the address below.

 Date: _______ __, ________ 

 

			
	 Name of Registered Holder

		
	 By:
	 	  

		 	 Name:

		 	 Title:

 Address for certificate or evidence of book entry delivery (if applicable): 

DTC Information (if applicable): 

 ACKNOWLEDGMENT 

The Company hereby acknowledges this Exercise Notice and hereby directs Computershare Trust Company, N.A. to issue the above
indicated number of shares of Common Stock. 
  

			
	THERAPEUTICSMD, INC.
		
	 By:
	 	  

	 Name:
	 	
	 Title:
	 	

 EXHIBIT B 

Officer’s Certificate 

(See attached) 

 EXHIBIT C 

Secretary’s Certificate 

(See attached)Exhibit 10.1

 

Evolv
Technologies Holdings, Inc.

Severance
And Change In Control Plan

 

Section 1.
Introduction and Purpose.

 

The purpose of this
Executive Severance and Change in Control Plan (the “Plan”) is to enable Evolv Technologies
Holdings, Inc. (the “Company”) to offer certain protections to certain senior-level employees if
their employment with the Company, is terminated without Cause or for Good Reason, both generally and in connection with a Change in
Control (as defined below). Accordingly, to accomplish this purpose, the Compensation Committee of the Board of Directors of the
Company (the “Board”) has adopted the Plan, effective as of January 1, 2023.

 

The Plan is intended to be (i) an employee
welfare benefit plan within the meaning of Section 3(1) of the Employee Retirement Income Security Act of 1974, as amended (“ERISA”),
and (ii) a “top hat” plan within the meaning of Sections 201(2), 301(a)(3) and 401(a)(1) of ERISA.

 

For purposes of the Plan,
the following terms are defined as follows:

 

(a)            “Base
Salary” means an Eligible Employee’s annual base salary (excluding incentive pay, premium pay, commissions, overtime,
bonuses and other forms of variable compensation) as in effect immediately prior to any reduction that would give rise to an employee’s
right to a resignation for Good Reason (if applicable).

 

(b)            “Cause”
means, with respect to an Eligible Employee (i) conduct constituting fraud, embezzlement, or illegal misconduct in connection with
the performance of Eligible Employee’s duties; (ii) the commission of, or voluntary and freely given confession to, or plea
of guilty or nolo contendere to, a crime which constitutes a felony (other than a traffic violation), an indictment that results
in material injury to the Company’s property, operation, or reputation, or a misdemeanor involving moral turpitude; (iii) the
willful failure to perform Eligible Employee’s employment duties or obligations (except resulting from incapacity or illness) as
reasonably and lawfully directed by Company that continues after (A) Company or its duly authorized designee delivers a written notice
to Eligible Employee describing such willful failure, and (B) Eligible Employee has failed to cure or take substantial steps to cure
such willful failure after a reasonable time period as determined by Company in its reasonable discretion (not to be less than 30 days);
(iv) willful misconduct or gross negligence that is materially injurious to the business, reputation or property of Company; (v) alcohol
or substance abuse that materially interferes with the performance of Eligible Employee’s duties or obligations; (vi) repeated
absence from work (either in-person or remote) during normal business hours for reasons other than permitted absence; (vii) violation
of Eligible Employee’s Non-Competition, Non-Solicitation, Non-Disclosure, and Intellectual Property Agreement or other similar agreement
containing restrictive covenants in favor of the Company; and (viii) repeated violation of any of the material policies or practices
of Company (including, but not limited to, discrimination or harassment), or a single serious violation of such policies or practices
which Company, in its discretion, determines is materially injurious to the business or reputation of Company.

 

(c)            “Change
in Control” has the meaning set forth in the Equity Plan, provided that the event qualifies as a change in the ownership
or effective control of the Company or a change in the ownership of a substantial portion of the assets of the Company, each within the
meaning of Section 409A.

 

(d)            “Change
in Control Date” means the closing date of a Change in Control.

 

     

     

    

 

(e)            “Change
in Control Period” means the period commencing 60 days prior to the Change in Control Date and ending 12 months following
such date.

 

(f)            “COBRA”
shall mean the Consolidated Omnibus Budget Reconciliation Act, as amended.

 

(g)           “Code”
means the Internal Revenue Code of 1986, as amended.

 

(h)           “Committee”
means the Board of Directors of the Company or the Compensation Committee of such Board of Directors.

 

(i)            “Common
Stock” means the Class A common stock, par value $0.0001 per share, of the Company.

 

(j)            “Company”
means Evolv Technologies Holdings, Inc. or, following a Change in Control, the surviving entity resulting from such event (such entity,
the “Successor Entity”). Except where the context otherwise requires, the term “Company” includes
any of the Company’s present or future parent or subsidiary corporations as defined in Sections 424(e) or (f) of
the Code and any other business venture (including, without limitation, joint venture or limited liability company) in which the Company
has a significant interest, as determined by the Plan Administrator.

 

(k)           “Covered
Termination” means, with respect to an Eligible Employee, a termination of employment that results in such employee’s
Separation from Service that is due to (i) a termination by the Company without Cause (and other than as a result of death or Disability)
or (ii) a resignation by the Eligible Employee for Good Reason.

 

(l)            “Disability”
means any physical or mental condition that renders an employee incapable of performing the work for which he or she was employed by the
Company or similar work offered by the Company. The Disability of an employee shall be established if (i) the employee satisfies
the requirements for benefits under the Company’s long-term disability plan of the Company or (ii) if no long-term disability
plan, the employee satisfies the requirements for Social Security disability benefits.

 

(m)          “Eligible
Employee” means an employee of the Company that meets the requirements to be eligible to receive Plan benefits as set forth
in Section 2.

 

(n)           “Equity
Plan” means the Company’s 2021 Incentive Award Plan, as amended from time to time, or any successor plan thereto.

 

(o)            “Good
Reason” for an employee’s resignation means the occurrence of any of the following that is undertaken by the Company
without the employee’s prior written consent:

 

		(i)	a material reduction in such employee’s Base Salary or Target Incentive Compensation by 10% or more,
as applicable;

 

		(ii)	a material reduction in such employee’s position, duties or responsibilities or any assignment to
such employee of duties or responsibilities that are materially inconsistent in an adverse respect with such employee’s position;
or

 

		(iii)	a material relocation of such employee’s principal place of employment with the Company (or Successor
Entity, if applicable) to a place that is more than 50 miles from the employee’s prior work location and which materially increases
such employee’s commute from the employee’s principal residence.

 

    2 

     

    

 

Notwithstanding the foregoing, in order for the
employee’s resignation to be deemed to have been for Good Reason, the employee must provide written notice to the Company, as applicable,
of such employee’s intent to resign for Good Reason within 30 days after the first occurrence of the event giving rise to
Good Reason, which notice shall describe the event(s) the employee believes give rise to Good Reason; allow the Company 30 days
from receipt of the written notice to cure the event (such period, the “Cure Period”); and if the event is
not reasonably cured within the Cure Period, the employee’s resignation from all positions held with the Company is effective not
later than 30 days after the expiration of the Cure Period. For purposes of clarification, the above-listed conditions shall apply separately
to each occurrence of Good Reason and failure to adhere to such conditions in the event of Good Reason shall not disqualify an Eligible
Employee from asserting Good Reasons for any subsequent occurrence of Good Reason.

 

(p)            “Plan
Administrator” means the Committee prior to the Change in Control Date and the Representative upon and following such date,
as applicable.

 

(q)            “Plan
Tier” means the tier to which an Eligible Employee is assigned for purposes of participation in the Plan, as determined
by the individual or entity that sets the Eligible Employee’s compensation, as set forth in the Eligible Employee’s Participation
Notice (as described in Section 2(a)).

 

(r)            “Representative”
means one or more members of the Committee or other persons or entities designated by the Committee prior to or in connection with a Change
in Control that will have authority to administer and interpret the Plan upon and following the Change in Control Date as provided in
Section 10.

 

(s)            “Section 409A”
means Section 409A of the Code and the treasury regulations and other guidance thereunder and any state law of similar effect.

 

(t)            “Separation
from Service” means a “separation from service” within the meaning of Treasury Regulation Section 1.409A-1(h).

 

(u)            “Target
Incentive Compensation” means an Eligible Employee’s target annual cash bonus or target annual variable cash compensation
(as determined by the Company) as in effect immediately prior to any reduction that would give rise to an employee’s right to a
resignation for Good Reason (if applicable).

 

Section 2.
Eligibility for Benefits.

 

(a)            Eligible
Employee. An employee of the Company is eligible to participate in the Plan if (i) the employee has the title of Vice
President or higher or has otherwise been designated by the Plan Administrator as eligible to participate; (ii) such employee is
designated as an Eligible Employee by the Plan Administrator through delivery of a Participation Notice in substantially the form attached
hereto as Exhibit 1 (which will specify, among other relevant terms, the employee’s Plan Tier); (iii) the
employee has signed and returned the Participation Notice provided by the Plan Administrator within the time provided by the Plan Administrator;
and (iv) the employee meets the other Plan eligibility requirements set forth in this Section 2. The determination of whether
an employee is an Eligible Employee shall be made by the Plan Administrator, in its sole discretion, and such determination shall be binding
and conclusive on all persons.

 

(b)            Release
Requirement. In order to be eligible to receive benefits under the Plan, the employee also must execute, and not revoke, a
valid separation and general release agreement in a form provided by the Company (the “Release”), within the
applicable time period set forth therein, and such Release must become effective in accordance with its terms, which must occur in no
event more than 60 days following the date of the applicable Covered Termination. If an employee does not provide a Release that becomes
effective as set forth above, no payments shall be made to such employee under the Plan, and the employee will have no further right
to any benefits under the Plan.

 

    3 

     

    

 

(c)            Plan
Benefits Provided In Lieu of Any Previous Benefits. This Plan shall supersede any change in control or severance benefit plan,
policy or practice previously maintained by the Company with respect to an Eligible Employee and any change in control or severance benefits
in any individually negotiated employment contract or other agreement between the Company and an Eligible Employee, including but not
limited to any management retention agreement between the Eligible Employee and the Company. Notwithstanding the foregoing, except as
expressly provided herein, the Eligible Employee’s equity awards will remain subject to the terms and conditions of the applicable
equity plan under which such awards were granted, and no provision of this Plan shall be construed as to limit the actions that may be
taken under, or to violate the terms of, such equity plan.

 

(d)            Exceptions
to Severance Benefit Entitlement. An employee who otherwise is an Eligible Employee shall not receive benefits under the Plan
in the following circumstances, as determined by the Plan Administrator in its sole discretion:

 

(1)            The
Eligible Employee is terminated by the Company for any reason (including due to the Eligible Employee’s death or Disability) or
voluntarily terminates employment with the Company in any manner, and in either case, such termination does not constitute a Covered Termination.
Voluntary terminations include, but are not limited to, resignation, retirement or job abandonment.

 

(2)            The
Eligible Employee is offered immediate reemployment by a Successor Entity following a Change in Control and the terms of such reemployment
would not give rise to the employee’s right to a resignation for Good Reason. For purposes of the foregoing, “immediate reemployment”
means that the employee’s employment with Successor Entity results in uninterrupted employment such that the employee does not incur
a lapse in pay or benefits as a result of the Change in Control. For the avoidance of doubt, an employee who becomes immediately reemployed
by a Successor Entity following a Change in Control will continue to be an Eligible Employee following the date of such reemployment.

 

(3)            The
Eligible Employee is rehired by the Company and the terms of such rehire would not give rise to the Eligible Employee’s right to
resignation for Good Reason, and the Eligible Employee commences employment prior to the date severance benefits under the Plan are scheduled
to commence.

 

(e)            Termination
of Severance Benefits. An Eligible Employee’s right to receive severance benefits under this Plan shall terminate immediately
if a court of competent jurisdiction enters a final order finding that the Eligible Employee breached his or her contractual obligations
to the Company, including those obligations set forth in any confidentiality, non-solicitation, non-competition agreement.

 

(f)            Company’s
Right to Reimbursement. If any person receives any payment or benefit that is not authorized by this Plan, the Company shall
be entitled to reimbursement of such payment or benefit from any person to whom, or for whom, such payment or benefit was paid. In addition,
if following the payment of severance benefits to an Eligible Employee, the Plan Administrator discovers that the Company could have terminated
such Eligible Employee’s employment in a manner that such termination would not have been a Covered Termination (including without
limitation a termination of employment for Cause), the Company shall be entitled to reimbursement of such payment from any person to whom,
or for whom, such payment was made.

 

    4 

     

    

 

Section 3.
Termination Benefits Generally.

 

Upon the termination of an
Eligible Employee’s employment for any reason, the Eligible Employee will be entitled to receive (i) any earned but unpaid
Base Salary and (ii) any vested employee benefits in accordance with the terms of the applicable employee benefit plan or program
(the “Accrued Benefits”). The Accrued Benefits shall be paid on or before the time required by law or applicable
policy, except to the extent any such payments would accelerate compensation in a manner inconsistent with Section 409A. In addition,
in the event of a Covered Termination, the Eligible Employee may be eligible to receive additional payments and benefits, as set forth
in Section 4 or Section 5 below, as applicable.

 

Section 4.
Benefits for Covered Termination Outside of a Change in Control Period

 

(a)            Covered
Termination. If an Eligible Employee experiences a Covered Termination at any time other than during the Change in Control
Period, the Eligible Employee will be entitled to receive the following severance benefits:

 

(1)            Base
Salary. The Eligible Employee will receive a cash severance payment equal to the Eligible Employee’s Base Salary for
the following number of months (such number of months, the “Severance Period” for that Eligible Employee), depending
on the Eligible Employee’s Plan Tier:

 

		(i)	Plan Tier 1:	12 months

 

		(ii)	Plan Tier 2:	9 months

 

		(iii)	Plan Tier 3:	6 months

 

The cash severance payment shall be paid in the
form of salary continuation over the course of the Severance Period, on the regular payroll dates of the Company or Affiliate as applicable,
subject to deductions and withholdings; provided however that no payment will be paid prior to the effective date of the Release, and
the first installment shall include a catch-up payment for any installments that would have otherwise been made from the date of the Covered
Termination through the effective date of the Release.

 

(2)            Payment
of Continued Group Health Plan Benefits. Subject to the Release becoming effective, if the Eligible Employee is eligible for
and timely elect to continue health insurance coverage under COBRA following a Covered Termination, the Company will pay the COBRA group
health insurance premiums for the Eligible Employee and his or her eligible dependents until the earliest of (A) the close of the
applicable Severance Period, (B) the expiration of the Eligible Employee’s eligibility for the continuation coverage under
COBRA, or (C) the date when the Eligible Employee become eligible for substantially equivalent health insurance coverage in connection
with new employment or self-employment. Notwithstanding the foregoing, if at any time the Company determines, in its sole discretion,
that it cannot pay the COBRA premiums without potentially incurring financial costs or penalties under applicable law (including, without
limitation, Section 2716 of the Public Health Service Act), then regardless of whether the Eligible Employee elects continued health
coverage under COBRA, and in lieu of providing the COBRA premiums, the Company will instead pay the Eligible Employee on the last day
of each remaining month of the applicable Severance Period, a fully taxable cash payment equal to the COBRA premiums for that month, subject
to applicable tax withholdings (such amount, the “Health Care Benefit Payment”).

 

(3)            Pro-Rata
Bonus Payment. Except as otherwise provided in an Eligible Employee’s Participation Notice, if the Eligible Employees
is eligible to receive an annual bonus pursuant to the Company’s corporate bonus or incentive compensation plan(s) then in
effect (i.e., and not under a commission plan or program or other bonus or incentive compensation plan or program that is calculated
and paid more frequently than annually), then the Eligible Employee will receive a lump sum cash payment equal to (x) a portion
of the Eligible Employee’s Target Incentive Compensation for the calendar year in which the Covered Termination occurs prorated
for the period from the beginning of such calendar year up to the date of such Covered Termination, regardless of their Plan Tier, less
(y) any amounts previously paid to the Eligible Employee for the year of termination under the applicable incentive compensation
plan(s). The payments referenced in this Sections 4(a)(3) shall be paid to the Eligible Employee in a single lump payment no later
than the second payroll cycle following the effective date of the Release. Additionally, the Eligible Employee will be paid any unpaid
annual bonus for the year prior to the year in which the Eligible Employee incurs a Covered Termination to which the Eligible Employee
would otherwise have been entitled had his or her employment not terminated.

 

    5 

     

    

 

(b)            No
Other Payments. The benefits set forth at subsections (a)(1), (a)(2), and (a)(3) above are the only benefits payable to
an Eligible Employee pursuant to the Plan with respect to a Covered Termination that occurs outside of a Change in Control Period.

 

Section 5.
Covered Termination Benefits (during a Change in Control Period).

 

(a)            Covered
Termination. If an Eligible Employee experiences a Covered Termination during a Change in Control Period, such Eligible Employee
will be entitled to receive the following severance benefits:

 

(1)            Base
Salary. The Eligible Employee will receive a cash severance payment equal to the Eligible Employee’s Base Salary for
the following number of months (such number of months, the “Change in Control Severance Period” for that Eligible
Employee), depending on the Eligible Employee’s Plan Tier:

 

		(i)	Plan Tier 1:	18 months

 

		(ii)	Plan Tier 2:	12 months

 

		(iii)	Plan Tier 3:	9 months

 

Such cash severance benefit shall be paid in a
single lump payment no later than the second payroll cycle following the later of (i) the effective date of the Release or (ii) the
Change in Control Date, but in any event not later than March 15 of the year following the year in which the Covered Termination
occurs.

 

Notwithstanding the foregoing, in the event of
a Covered Termination that occurs within the 60 day period prior to the Change in Control Date, the amount payable pursuant to this Section 5(a)(1) shall
be reduced by any amounts previously paid pursuant to Section 4 above, and the net cash severance benefit shall be paid as set forth
in this Section 5(a)(1).

 

(2)            Payment
of Continued Group Health Plan Benefits. During the Change in Control Severance Period, the Eligible Employee will be eligible
to receive the payments described in, and pursuant to the terms of, Section 4(a)(2) above; provided however that in the event
of a Covered Termination that occurs within the 60 day period prior to the Change in Control Date, the Change in Control Severance Period
will be reduced by the number of months, if any, for which COBRA payments were made pursuant to Section 4(a)(2) above.

 

    6 

     

    

 

(3)            Incentive
Payments. The Eligible Employee will receive a lump sum cash payment equal to a percentage of either the Eligible Employee’s
Target Incentive Compensation for the calendar year in which the Covered Termination occurs (which for the avoidance of doubt will not
be pro-rated), depending on their Plan Tier, less any amounts previously paid to the Eligible Employee for the year of termination under
the applicable incentive compensation plan(s):

 

		(i)	Plan Tier 1:	150% of Target Incentive Compensation

 

		(ii)	Plan Tier 2:	100% of Target Incentive Compensation

 

		(iii)	Plan Tier 3:	75% of Target Incentive Compensation

 

This payment shall be paid to the Eligible Employee
in a lump-sum cash payment on the same date as the Base Salary payment provided in subsection 5(a)(1) above. Additionally, the Eligible
Employee will be paid any unpaid annual bonus for the year prior to the year in which the Eligible Employee incurs a Covered Termination
to which the Eligible Employee would otherwise have been entitled had his or her employment not terminated. Notwithstanding the foregoing,
in the event of a Covered Termination that occurs within the 60 day period prior to the Change in Control Date, the amount payable pursuant
to this Section 5(a)(3) shall be reduced by any amounts previously paid pursuant to Section 4 above, and the net cash severance
benefit shall be paid as set forth in this Section.

 

(4)            Equity
Acceleration. The vesting and exercisability of each outstanding unvested stock option, unvested restricted stock unit, and
other stock awards, as applicable, held by the Eligible Employee covering Common Stock as of the date of the Covered Termination (each,
an “Equity Award”) that vest solely based on continued service with the Company over time will be accelerated
in full, effective as of the later of (x) the effective date of the Release or (y) the Change in Control Date. Any termination
or forfeiture of any unvested portion of such time-based Equity Awards that would otherwise occur on or after the Covered Termination
in the absence of this Section shall be delayed (but, with respect to stock options, not later than the original expiration date
for such option) and shall only occur if the vesting pursuant to this Section does not occur due, and for purposes of clarity, no
additional vesting shall occur during this period. Notwithstanding the foregoing, Equity Awards subject to vesting based on the attainment
of performance goals will not be subject to acceleration, except as determined by the Committee in its sole discretion either pursuant
to the Plan or pursuant to the Equity Plan. To the extent an Equity Award is assumed, continued or substituted for in a Change in Control
pursuant to such applicable equity incentive plan, the vesting acceleration described in this Section 5(a)(4) will apply to
such assumed, continued or substituted award, as applicable.

 

(b)            No
Duplication of Benefits. The benefits set forth at subsections (a)(1) through (a)(4) above are the only benefits
payable to an Eligible Employee pursuant to the Plan with respect to a Covered Termination that occurs during a Change in Control Period,
and shall be paid in lieu of any benefits that may be payable pursuant to Section 4 above with respect to a Covered Termination that
occurs outside of a Change in Control Period. For the avoidance of doubt, in no event will benefits be provided under both Section 4
and Section 5 to the same Eligible Employee (except to the extent that benefits were provided pursuant to Section 4 with respect
to a Covered Termination that occurred during the 60 day period prior to a Change in Control Date, in which case the benefits provided
pursuant to Sections 5(a)(1) through 5(a)(3) will be adjusted as set forth above).

 

Section 6.
Section 280G Limitation.

 

Notwithstanding anything
in the Plan to the contrary, if any payment or benefit an Eligible Employee will or may receive from the Company or an Affiliate or otherwise
(each payment or benefit, a “Payment,” and in the aggregate, the “Payments”) would
(i) constitute a “parachute payment” within the meaning of Section 280G of the Code, and (ii) but for this
sentence, be subject to the excise tax imposed by Section 4999 of the Code (the “Excise Tax”), then the
Payments shall be reduced (but not below zero) so that the sum of the Payments will be $1.00 less than the amount at which the Eligible
Employee becomes subject to the Excise Tax; provided that such reduction will only occur if it would result in the Eligible Employee
receiving a higher After Tax Amount (as defined below) than the Eligible Employee would receive absent such reduction. In the event of
such reduction, the Payments will be reduced in the following order, in each case, in reverse chronological order beginning with the
Payments that are to be paid the furthest in time from consummation of the transaction that is subject to Section 280G of the Code:
(1) cash payments not subject to Section 409A; (2) cash payments subject to Section 409A; (3) equity-based payments
and acceleration; and (4) non-cash forms of benefits; provided that in the case of all the foregoing Payments all amounts
or payments that are not subject to calculation under Treas. Reg. §1.280G-1, Q&A-24(b) or (c) will be reduced
before any amounts that are subject to calculation under Treas. Reg. §1.280G-1, Q&A-24(b) or (c).

 

    7 

     

    

 

For purposes of this Section 6,
the term “After Tax Amount” means the amount of the Payments less all federal, state, and local income, excise
and employment taxes imposed on the Eligible Employee as a result of the Eligible Employee’s receipt of the Payments. For purposes
of determining the After Tax Amount, the Eligible Employee will be deemed to pay federal income taxes at the highest marginal rate of
federal income taxation applicable to individuals for the calendar year in which the determination is to be made, and state and local
income taxes at the highest marginal rates of individual taxation in each applicable state and locality, net of the maximum reduction
in federal income taxes (if any) which could be obtained from deduction of such state and local taxes.

 

The determination as to whether
a reduction in the Payments will be made pursuant to this Section 6 shall be made by the Company in consultation with its external
advisers, and the Company shall provide reasonably detailed supporting calculations to the Eligible Employee within 15 business days
of the Eligible Employee’s Covered Termination.

 

Section 7.
Withholding.

 

All payments under the Plan
will be subject to applicable withholding for federal, state, foreign, and local taxes.

 

Section 8.
Section 409A.

 

All benefits provided under
the Plan are intended to be exempt from the requirements of Section 409A to the maximum extent possible and any ambiguities herein
shall be interpreted accordingly; provided, however, that to the extent that any benefits are not so exempt, such benefits are intended
to comply with the requirements of Section 409A and any ambiguities herein shall be interpreted accordingly. It is intended that
each installment of benefits payable to an Eligible Employee be regarded as a separate “payment” for purposes of Treasury
Regulations Section 1.409A-2(b)(2)(i).

 

If the Company determines
that any benefits payable under the Plan constitute “deferred compensation” under Section 409A and the Eligible Employee
is a “specified employee” of the Company, as such term is defined in Section 409A, then, to the extent necessary to avoid
the imposition of the adverse tax consequences under Section 409A, the timing of such benefit payments shall be delayed until the
earlier of (1) the date that is six months and one day after the Eligible Employee’s Separation from Service and (2) the
date of the Eligible Employee’s death. In the event of such delayed payment, the Company shall then pay the Eligible Employee a
lump sum amount equal to the sum of the severance benefit payments that would otherwise have been paid prior to the delay and pay any
remaining amounts of severance benefits in accordance with the applicable payment schedule.

 

    8 

     

    

 

In no event will payment
of any benefits under the Plan be made prior to an Eligible Employee’s Separation from Service or prior to the effective date of
the Release. If the Company determines that any benefits provided under the Plan constitute “deferred compensation” under
Section 409A, and the period for providing a Release set forth at Section 2(b) above spans two calendar years, then regardless
of when the Release is returned to the Company and becomes effective, the Release will not be deemed effective, solely for purposes of
the timing of payment of benefits under this Plan, until the later of the day that it would become effective under its terms or the first
day of the latter calendar year.

 

Notwithstanding the foregoing,
the Company makes no representation or warranty and will have no liability to the Eligible Employee or any other person if any provisions
of this Plan are determined to constitute deferred compensation subject to Section 409A but do not satisfy an exemption from, or
the conditions of, Section 409A.

 

Section 9.
Transfer and Assignment.

 

The rights and obligations
of an Eligible Employee under this Plan may not be transferred or assigned. The Plan shall be binding upon any entity or person who is
a successor by merger, acquisition, consolidation or otherwise to the business formerly carried on by the Company without regard to whether
or not such entity or person actively assumes the obligations hereunder and without regard to whether or not a Change in Control occurs.

 

Section 10.
Right to Interpret and Administer Plan; Amendment and Termination.

 

(a)            Interpretation
and Administration. Prior to a Change in Control, the Committee shall be the Plan Administrator and will have the exclusive
discretion and authority to establish rules, forms, and procedures for the administration of the Plan and to construe and interpret the
Plan and to decide any and all questions of fact, interpretation, definition, computation or administration arising in connection with
the operation of the Plan, including, but not limited to, the eligibility to participate in the Plan and amount of benefits paid under
the Plan. The rules, interpretations, computations and other actions of the Committee shall be binding and conclusive on all persons.
Upon and after the Change in Control Date, the Plan will be interpreted and administered in good faith by the Representative who shall
be the Plan Administrator during such period. All actions taken by the Representative in interpreting the terms of the Plan and administering
the Plan upon and after the Change in Control Date will be final and binding on all Eligible Employees. Any references in this Plan to
the “Committee” or “Plan Administrator” with respect to periods following such date shall mean the Representative.

 

(b)            Amendment.
The Plan Administrator reserves the right to amend or terminate this Plan at any time; provided however that no such amendment or termination
shall materially and adversely affect the rights of any Eligible Employee who has satisfied the requirements of Section 2(a) without
the consent of such Eligible Employee.

 

(c)            Termination.
Unless otherwise extended by the Committee, the Plan will automatically terminate following satisfaction of all the Company’s
obligations under the Plan.

 

(d)            Clawback;
Recovery. All payments and severance benefits provided under the Plan will be subject to recoupment in accordance with
any clawback policy that the Company is required to adopt pursuant to the listing standards of any national securities exchange or association
on which the Company’s securities are listed or as is otherwise required by the Dodd-Frank Wall Street Reform and Consumer Protection
Act or other applicable law. In addition, the Plan Administrator may impose such other clawback, recovery or recoupment provisions as
the Plan Administrator determines necessary or appropriate, including but not limited to a reacquisition right in respect of previously
acquired shares of common stock of the Company or other cash or property, including upon the occurrence of a termination of employment
for Cause. No recovery of compensation under such a clawback policy will be an event giving rise to an event permitting a resignation
for Good Reason, constructive termination, or any similar term under any plan of or agreement with the Company.

 

    9 

     

    

 

Section 11.
No Implied Employment Contract.

 

The Plan shall not be deemed
(i) to give any employee or other person any right to be retained in the employ of the Company or a Successor Entity, as applicable,
or (ii) to interfere with the right of the Company or a Successor Entity, as applicable, to discharge any employee or other person
at any time, with or without cause, which right is hereby reserved. This Plan does not modify the at-will employment status of any Eligible
Employee.

 

Section 12.
Plan is Unfunded.

 

The Plan shall be unfunded,
and all cash payments under the Plan paid only from the general assets of the Company.

 

Section 13.
Severability.

 

In case any one or more of
the provisions of this Plan (or part thereof) shall be held to be invalid, illegal or unenforceable in any respect, such invalidity, illegality
or unenforceability shall not affect the other provisions hereof, and this Plan shall be construed as if such invalid, illegal or unenforceable
provisions (or part thereof) never had been contained herein.

 

Section 14.
Governing Law.

 

This Plan is intended to be
governed by and shall be construed in accordance with ERISA and, to the extent not preempted by ERISA, the laws of the State of Delaware.

 

Section 15.
Claims, Inquiries and Appeals.

 

(a)            Applications
for Benefits and Inquiries. Any application for benefits, inquiries about the Plan or inquiries about present or future rights
under the Plan must be submitted to the Plan Administrator in writing by an applicant (or his or her authorized representative).

 

(b)            Denial
of Claims. In the event that any application for benefits is denied in whole or in part, the Plan Administrator must provide
the applicant with written or electronic notice of the denial of the application, and of the applicant’s right to review the denial.
Any electronic notice will comply with the regulations of the U.S. Department of Labor. The notice of denial will be set forth in a manner
designed to be understood by the applicant and will include the following: (i) the specific reason or reasons for the denial; (ii) references
to the specific Plan provisions upon which the denial is based; (iii) a description of any additional information or material that
the Plan Administrator needs to complete the review and an explanation of why such information or material is necessary; and (iv) an
explanation of the Plan’s review procedures and the time limits applicable to such procedures, including a statement of the applicant’s
right to bring a civil action under Section 502(a) of ERISA following a denial on review of the claim. This notice of denial
will be given to the applicant within 90 days after the Plan Administrator receives the application, unless special circumstances require
an extension of time, in which case, the Plan Administrator has up to an additional 90 days for processing the application. If an extension
of time for processing is required, written notice of the extension will be furnished to the applicant before the end of the initial
90-day period, describing the special circumstances necessitating the additional time and the date by which the Plan Administrator is
to render its decision on the application.

 

    10 

     

    

 

(c)            Request
for a Review. Any person (or that person’s authorized representative) for whom an application for benefits is denied,
in whole or in part, may appeal the denial by submitting a request for a review to the Plan Administrator within 60 days after the application
is denied. A request for review must set forth all of the grounds on which it is based, all facts in support of the request and any other
matters that the applicant feels are pertinent. The applicant (or his or her representative) will have the opportunity to submit (or the
Plan Administrator may require the applicant to submit) written comments, documents, records, and other information relating to his or
her claim. The applicant (or his or her representative) shall be provided, upon request and free of charge, reasonable access to, and
copies of, all documents, records and other information relevant to his or her claim. The review will take into account all comments,
documents, records and other information submitted by the applicant (or his or her representative) relating to the claim, without regard
to whether such information was submitted or considered in the initial benefit determination.

 

(d)            Decision
on Review. The Plan Administrator will act on each request for review within 60 days after receipt of the request, unless special
circumstances require an extension of time (not to exceed an additional 60 days), for processing the request for a review. If an extension
for review is required, written notice of the extension will be furnished to the applicant within the initial 60-day period. This notice
of extension will describe the special circumstances necessitating the additional time and the date by which the Plan Administrator is
to render its decision on the review. The Plan Administrator will give prompt, written or electronic notice of its decision to the applicant.
Any electronic notice will comply with the regulations of the U.S. Department of Labor. In the event that the Plan Administrator confirms
the denial of the application for benefits in whole or in part, the notice will set forth, in a manner calculated to be understood by
the applicant, the following: (ii) the specific reason or reasons for the denial; (ii) references to the specific Plan provisions
upon which the denial is based; (iii) a statement that the applicant is entitled to receive, upon request and free of charge, reasonable
access to, and copies of, all documents, records and other information relevant to his or her claim; and (iv) a statement of the
applicant’s right to bring a civil action under Section 502(a) of ERISA.

 

(e)            Rules and
Procedures. The Plan Administrator will establish rules and procedures, consistent with the Plan and with ERISA, as necessary
and appropriate in carrying out its responsibilities in reviewing benefit claims. The Plan Administrator may require an applicant who
wishes to submit additional information in connection with an appeal from the denial of benefits to do so at the applicant’s own
expense.

 

(f)            Exhaustion
of Remedies. No legal action for benefits under the Plan may be brought until the applicant (i) has submitted a written
application for benefits in accordance with the procedures described by Section 14(a) above, (ii) has been notified by
the Plan Administrator that the application is denied, (iii) has filed a written request for a review of the application in accordance
with the appeal procedure described in Section 14(c) above, and (iv) has been notified that the Plan Administrator has
denied the appeal. Notwithstanding the foregoing, if the Plan Administrator does not respond to an Eligible Employee’s claim or
appeal within the relevant time limits specified in this Section 14, the Eligible Employee may bring legal action for benefits under
the Plan pursuant to Section 502(a) of ERISA. Any such legal action for benefits under the Plan must be brought within 12 months
from the date the Plan Administrator denies the claim on appeal.

 

    11 

     

    

 

Other Plan Information.

 

Employer
and Plan Identification Numbers: The Employer Identification Number assigned to the Company (which is the “Plan Sponsor”
as that term is used in ERISA) by the Internal Revenue Service is 46-3181906. The Plan Number assigned to the Plan by the Plan Sponsor
pursuant to the instructions of the Internal Revenue Service is 510.

 

Plan
Year: The Plan is maintained on a calendar year (January 1 – December 31).

 

Plan
Administrator: The Committee prior to the Change in Control Date, and the Representative upon and following such date.

 

Agent
for Service of Legal Process: Eric Pyenson, General Counsel, Evolv Technologies Holdings Inc., Inc., 500 Totten Pond Rd.
Waltham, MA 02451

 

Statement
of ERISA Rights. Participants in this Plan (which is a welfare benefit plan sponsored by Evolv Technologies Holdings, Inc.)
are entitled to certain rights and protections under ERISA. If you are an Eligible Employee, you are considered a participant in the Plan
and, under ERISA, you are entitled to:

 

Receive
Information About Your Plan and Benefits. This includes the right to (i) examine, without charge, at the Plan Administrator’s
office and at other specified locations, such as worksites, all documents governing the Plan and a copy of the latest annual report (Form 5500
Series), if applicable, filed by the Plan with the U.S. Department of Labor and available at the Public Disclosure Room of the Employee
Benefits Security Administration; (ii) obtain, upon written request to the Plan Administrator, copies of documents governing the
operation of the Plan and copies of the latest annual report (Form 5500 Series), if applicable, and an updated (as necessary) Summary
Plan Description (provided that a reasonable charge may be made for such copies; and (iii) receive a summary of the Plan’s
annual financial report, if applicable. The Plan Administrator is required by law to furnish each Eligible Employee with a copy of this
summary annual report.

 

Prudent
Actions by Plan Fiduciaries. In addition to creating rights for employees eligible to participate in the Plan, ERISA imposes
duties upon the people who are responsible for the operation of the employee benefit plan. The people who operate the Plan, called “fiduciaries”
of the Plan, have a duty to do so prudently and in the interest of you and other Eligible Employees and beneficiaries. No one, including
your employer, your union or any other person, may fire you or otherwise discriminate against you in any way to prevent you from obtaining
a Plan benefit or exercising your rights under ERISA.

 

Enforce
Your Rights. If your claim for a Plan benefit is denied or ignored, in whole or in part, you have a right to know why this
was done, to obtain copies of documents relating to the decision without charge, and to appeal any denial, all within certain time schedules.
Under ERISA, there are steps you can take to enforce the above rights. For instance, if you request a copy of Plan documents or the latest
annual report from the Plan, if applicable, and do not receive them within 30 days, you may file suit in a Federal court. In such a case,
the court may require the Plan Administrator to provide the materials and pay you up to $110 a day until you receive the materials, unless
the materials were not sent because of reasons beyond the control of the Plan Administrator. If you have a claim for benefits which is
denied or ignored, in whole or in part, you may file suit in a state or Federal court. If you are discriminated against for asserting
your rights, you may seek assistance from the U.S. Department of Labor, or you may file suit in a Federal court. The court will decide
who should pay court costs and legal fees. If you are successful, the court may order the person you have sued to pay these costs and
fees. If you lose, the court may order you to pay these costs and fees, for example, if it finds your claim is frivolous.

 

Assistance
with Your Questions. If you have any questions about the Plan, you should contact the Plan Administrator. If you have any
questions about this statement or about your rights under ERISA, or if you need assistance in obtaining documents from the Plan Administrator,
you should contact the nearest office of the Employee Benefits Security Administration, U.S. Department of Labor, listed in your telephone
directory or the Division of Technical Assistance and Inquiries, Employee Benefits Security Administration, U.S. Department of Labor,
200 Constitution Avenue N.W., Washington, D.C. 20210. You may also obtain certain publications about your rights and responsibilities
under ERISA by calling the publications hotline of the Employee Benefits Security Administration.

 

    12 

     

    

 

EXHIBIT 1

Participation
Notice

 

[Date]

 

Dear [●]:

 

Evolv Technologies Holdings, Inc.
(the “Company”) is pleased to inform you that you have been designated as an Eligible Employee, Plan Tier [●]
in, and are eligible to receive Severance Benefits under, the Company’s Severance and Change in Control Plan (the “Plan”).
A copy of the Plan is being provided to you along with this notice (this “Participation Notice”). Capitalized
terms used but not defined in this Participation Notice will have the definitions provided in the Plan.

 

As
an Eligible Employee, at Plan Tier [●] under the Plan, you will be eligible to receive certain Severance Benefits upon a
Covered Termination, subject to the terms, conditions and requirements set forth in the Plan (including your timely execution and, if
applicable, non-revocation of a Release in accordance with the terms of the Plan). [Notwithstanding Section 4(a)(3) of the
Plan, in lieu of the Pro-Rata Bonus Payment described in such section, in connection with a Covered Termination under Section 4(a) of
the Plan, you will be eligible to receive an amount equal to the greater of (x) [●]% of your Target Incentive Compensation
for the calendar year in which the Covered Termination occurs and (y) the Pro-Rata Bonus Payment calculated under Section 4(a)(3) of
the Plan, in each case, payable pursuant to and subject to the terms and conditions of, the Plan.]

 

This Participation Notice
is subject in all respects to the terms, conditions and provisions of the Plan, as amended from time to time, all of which are made a
part of and incorporated by reference into this Participation Notice. In the event of any conflict between the terms of this Participation
Notice and the terms of the Plan, the terms of the Plan shall govern. By signing below, you acknowledge and agree that (i) you have
received and reviewed a copy of the Plan and (ii) your participation in the Plan requires that you irrevocably and voluntarily agree
to the terms of the Plan and the terms set forth in this Participation Notice.

 

In consideration of becoming
eligible to receive the payments and benefits provided under the terms and conditions of the Plan, you agree that you hereby waive any
and all rights, benefits, and privileges to severance payments and benefits that you might otherwise be entitled to receive under any
other plan or arrangement between you and the Company or any Subsidiary (including, without limitation [●], and any
offer letter, any employment or similar agreement or arrangement), and that the Plan and this Participation Notice supersede any such
rights, benefits, and privileges.

 

This Participation Notice
shall terminate, and your status as a Participant in the Plan shall end, upon your termination of employment with the Company for any
reason other than due to a Covered Termination.

 

     

     

    

 

If you have any questions
regarding the foregoing, please contact [●]. Please confirm your agreement to the
foregoing by executing this Participation Notice where indicated below and returning a signed copy to me.

 

	 	Sincerely,
	 	 
	 	EVOLV TECHNOLOGIES HOLDINGS, INC.

 

 

		By:	 

		Name:	
	 	Title:	

 

ACKNOWLEDGED AND AGREED:

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