Document:

Exhibit 10.1

 

Note
Purchase Agreement

 

This
Note Purchase Agreement (this “Agreement”),
dated as of March 18, 2020, is entered into by and between Inpixon, a Nevada corporation
(“Company”), and Iliad Research and Trading, L.P., a Utah limited
partnership, its successors and/or assigns (“Investor”).

 

A. Company
and Investor are executing and delivering this Agreement in reliance upon the exemption from securities registration afforded
by the Securities Act of 1933, as amended (the “1933 Act”), and the rules and regulations promulgated thereunder
by the United States Securities and Exchange Commission (the “SEC”).

 

B. Investor
desires to purchase and Company desires to issue and sell, upon the terms and conditions set forth in this Agreement, a Promissory
Note, in the form attached hereto as Exhibit A (the “Note”), in the original principal amount of $6,465,000.00
(the “Initial Principal Amount”).

 

C. This
Agreement, the Note, and all other certificates, documents, agreements, resolutions and instruments delivered to any party under
or in connection with this Agreement, as the same may be amended from time to time, are collectively referred to herein as the
“Transaction Documents”.

 

NOW,
THEREFORE, in consideration of the above recitals and other good and valuable consideration, the receipt and sufficiency of
which are hereby acknowledged, Company and Investor hereby agree as follows:

 

1. Purchase
and Sale of Note.

 

1.1. Purchase
of Note. Company shall issue and sell to Investor and Investor shall purchase from Company the Note. In consideration thereof,
Investor shall pay the Purchase Price (as defined below) to Company.

 

1.2. Form
of Payment. On the Closing Date (as defined below), Investor shall pay the Purchase Price to Company via wire transfer of
immediately available funds against delivery of the Note.

 

1.3. Closing
Date. Subject to the satisfaction (or written waiver) of the conditions set forth in Section 5 and Section 6 below, the date
of the issuance and sale of the Note pursuant to this Agreement (the “Closing Date”) shall be March 18, 2020,
or such other mutually agreed upon date. The closing of the transactions contemplated by this Agreement (the “Closing”)
shall occur on the Closing Date by means of the exchange by email of signed .pdf documents, but shall be deemed for all purposes
to have occurred at the offices of Hansen Black Anderson Ashcraft PLLC in Lehi, Utah.

 

1.4. Collateral
for the Note. The Note shall not be secured.

 

1.5. Original
Issue Discount; Transaction Expense Amount. The Note carries an original issue discount of $1,450,000.00 (the “OID”).
In addition, Company agrees to pay $15,000.00 to Investor to cover Investor’s legal fees, accounting costs, due diligence,
monitoring and other transaction costs incurred in connection with the purchase and sale of the Note (the “Transaction
Expense Amount”), all of which amount is included in the initial original principal amount of the Note. The “Purchase
Price”, therefore, shall be $5,000,000.00, computed as follows: the Initial Principal Amount, less the OID, less the
Transaction Expense Amount.

 

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2. Investor’s
Representations and Warranties. Investor represents and warrants to Company that as of the date hereof:

 

2.1. Organization;
Authority. Investor 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 to which it is a party and otherwise to carry out its obligations hereunder and thereunder.

 

2.2. No
Public Sale or Distribution. Investor is acquiring the Note for its own account and not with a view towards, or for resale
in connection with, the public sale or distribution thereof in violation of applicable securities laws, except pursuant to sales
registered or exempted under the 1933 Act; provided, however, by making the representations herein, Investor does not agree, or
make any representation or warranty, to hold the Note for any minimum or other specific term and reserves the right to dispose
of the Note at any time in accordance with or pursuant to a registration statement or an exemption from registration under the
1933 Act. Investor does not presently have any agreement or understanding, directly or indirectly, with any Person to distribute
the Note in violation of applicable securities laws. For purposes of this Agreement, “Person” means an individual,
a limited liability company, a partnership, a joint venture, a corporation, a trust, an unincorporated organization, any other
entity and any governmental entity or any department or agency thereof.

 

2.3. Accredited
Investor Status. Investor is an “accredited investor” as that term is defined in Rule 501(a) of Regulation D promulgated
under the 1933 Act.

 

2.4. Reliance
on Exemptions. Investor understands that the Note is 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 Company is relying in part upon the
truth and accuracy of, and Investor’s compliance with, the representations, warranties, agreements, acknowledgments and
understandings of Investor set forth herein in order to determine the availability of such exemptions and the eligibility of Investor
to acquire the Note.

 

2.5. Information.
Investor and its advisors, if any, have been furnished with all materials relating to the business, finances and operations of
Company and materials relating to the offer and sale of the Note that have been requested by Investor. Investor and its advisors,
if any, have been afforded the opportunity to ask questions of Company. Neither such inquiries nor any other due diligence investigations
conducted by Investor or its advisors, if any, or its representatives shall modify, amend or affect Investor’s right to rely on
Company’s representations and warranties contained herein. Investor understands that its investment in the Note involves a high
degree of risk. Investor has sought such accounting, legal and tax advice as it has considered necessary to make an informed investment
decision with respect to its acquisition of the Note.

 

2.6. No
Governmental Review. Investor 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 Note or the fairness or suitability of the investment in
the Note nor have such authorities passed upon or endorsed the merits of the offering of the Note.

 

2.7. Registration.
Investor understands that the Note has not been and is not being registered under the 1933 Act or any state securities laws. Investor
further understands and acknowledges that Company will not be obligated in the future to register the Note under the 1933 Act
or the Securities Exchange Act of 1934, as amended (the “1934 Act”), or under any state securities laws and
that Company has not made or is making any representation, warranty or covenant, express or implied, as to the availability of
any exemption from registration under the 1933 Act or any applicable state securities laws for the resale, pledge or other transfer
of the Note.

 

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2.8. Validity;
Enforcement. This Agreement has been duly and validly authorized, executed and delivered on behalf of Investor and shall constitute
the legal, valid and binding obligations of Investor enforceable against Investor in accordance with its terms, except as such
enforceability may be limited by general principles of equity or to applicable bankruptcy, insolvency, reorganization, moratorium,
liquidation and other similar laws relating to, or affecting generally, the enforcement of applicable creditors’ rights
and remedies.

 

2.9. No
Conflicts. The execution, delivery and performance by Investor of this Agreement and the consummation by Investor of the transactions
contemplated hereby will not (i) result in a violation of the organizational documents of Investor, (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 Investor is a party
or (iii) result in a violation of any law, rule, regulation, order, judgment or decree (including federal and state securities
laws) applicable to Investor, except, in the case of clauses (ii) and (iii) above, for such conflicts, defaults, rights or violations
which could not, individually or in the aggregate, reasonably be expected to have a material adverse effect on the ability of
Investor to perform its obligations hereunder.

 

3. Company’s
Representations and Warranties. Company represents and warrants to Investor that as of the date hereof: (i) Company is a corporation
duly organized, validly existing and in good standing under the laws of its state of incorporation and has the requisite corporate
power to own its properties and to carry on its business as now being conducted; (ii) Company is duly qualified as a foreign corporation
to do business and is in good standing in each jurisdiction where the nature of the business conducted or property owned by it
makes such qualification necessary; (iii) Company has registered its shares of common stock, $0.001 par value per share (the “Common
Stock”), under Section 12(b) of the 1934 Act, and is obligated to file reports pursuant to Section 13 or Section 15(d)
of the 1934 Act; (iv) each of the Transaction Documents and the transactions contemplated hereby and thereby, have been duly and
validly authorized by Company and all necessary actions have been taken; (v) this Agreement, the Note, and the other Transaction
Documents have been duly executed and delivered by Company and constitute the valid and binding obligations of Company enforceable
in accordance with their terms; (vi) the execution and delivery of the Transaction Documents by Company, the issuance of the Note
in accordance with the terms hereof, and the consummation by Company of the other transactions contemplated by the Transaction
Documents do not and will not conflict with or result in a breach by Company of any of the terms or provisions of, or constitute
a default under (a) Company’s formation documents or bylaws, each as currently in effect, (b) any indenture, mortgage, deed
of trust, or other material agreement or instrument to which Company is a party or by which it or any of its properties or assets
are bound, including, without limitation, any listing agreement for the Common Stock, or (c) any existing applicable law, rule,
or regulation or any applicable decree, judgment, or order of any court, United States federal, state or foreign regulatory body,
administrative agency, or other governmental body having jurisdiction over Company or any of Company’s properties or assets;
(vii) no further authorization, approval or consent of any court, governmental body, regulatory agency, self-regulatory organization,
or stock exchange or market or the stockholders or any lender of Company is required to be obtained by Company for the issuance
of the Note to Investor or the entering into any of the Transaction Documents that has not been obtained; (viii) none of Company’s
filings with the SEC contained, at the time they were filed, any untrue statement of a material fact or omitted to state any material
fact required to be stated therein or necessary to make the statements made therein, in light of the circumstances under which
they were made, not misleading; (ix) Company has filed all reports, schedules, forms, statements and other documents required
to be filed by Company with the SEC under the 1934 Act on a timely basis or has received a valid extension of such time of filing
and has filed any such report, schedule, form, statement or other document prior to the expiration of any such extension; (x)
other than as disclosed in Company’s filings with the SEC, there is no action, suit, proceeding, inquiry or investigation
before or by any court, public board or body pending or, to the knowledge of Company, threatened against or affecting Company
before or by any governmental authority or non-governmental department, commission, board, bureau, agency or instrumentality or
any other person, wherein an unfavorable decision, ruling or finding would have a material adverse effect on Company or which
would adversely affect the validity or enforceability of, or the authority or ability of Company to perform its obligations under,
any of the Transaction Documents; (xi) Company has not consummated any material financing transaction that has not been disclosed
in a periodic filing or current report with the SEC under the 1934 Act; (xii) Company is not, nor has it been at any time in the
previous twelve (12) months, a “Shell Company,” as such type of “issuer” is described in Rule 144(i)(1)
under the 1933 Act; (xiii) with respect to any commissions, placement agent or finder’s fees or similar payments that will
or would become due and owing by Company to any person or entity as a result of this Agreement or the transactions contemplated
hereby (“Broker Fees”), any such Broker Fees will be made in full compliance with all applicable laws and regulations
and only to a person or entity that is a registered investment adviser or registered broker-dealer; (xiv) Investor shall have
no obligation with respect to any Broker Fees or with respect to any claims made by or on behalf of other persons for fees of
a type contemplated in this subsection that may be due in connection with the transactions contemplated hereby and Company shall
indemnify and hold harmless each of Investor, Investor’s employees, officers, directors, stockholders, members, managers,
agents, and partners, and their respective affiliates, from and against all claims, losses, damages, costs (including the costs
of preparation and attorneys’ fees) and expenses suffered in respect of any such claimed Broker Fees; (xv) neither Investor
nor any of its officers, directors, stockholders, members, managers, employees, agents or representatives has made any representations
or warranties to Company or any of its officers, directors, employees, agents or representatives except as expressly set forth
in the Transaction Documents and, in making its decision to enter into the transactions contemplated by the Transaction Documents,
Company is not relying on any representation, warranty, covenant or promise of Investor or its officers, directors, members, managers,
employees, agents or representatives other than as set forth in the Transaction Documents; (xvi) Company acknowledges that the
State of Utah has a reasonable relationship and sufficient contacts to the transactions contemplated by the Transaction Documents
and any dispute that may arise related thereto such that the laws and venue of the State of Utah, as set forth more specifically
in Section 9.3 below, shall be applicable to the Transaction Documents and the transactions contemplated therein; and (xvii) Company
has performed due diligence and background research on Investor and its affiliates including, without limitation, John M. Fife,
and, to its satisfaction, has made inquiries with respect to all matters Company may consider relevant to the undertakings and
relationships contemplated by the Transaction Documents including, among other things, the following: http://investing.businessweek.com/research/stocks/people/person.asp?personId=7505107&ticker=UAHC;
SEC Civil Case No. 07-C-0347 (N.D. Ill.); SEC Civil Action No. 07-CV-347 (N.D. Ill.); and FINRA Case #2011029203701. Company,
being aware of the matters described in subsection (xvii) above, acknowledges and agrees that such matters, or any similar matters,
have no bearing on the transactions contemplated by the Transaction Documents and covenants and agrees it will not use any such
information as a defense to performance of its obligations under the Transaction Documents or in any attempt to avoid, modify
or reduce such obligations.

 

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4. Company
Covenants. Until all of Company’s obligations under all of the Transaction Documents are paid and performed in full,
or within the timeframes otherwise specifically set forth below, Company will at all times comply with the following covenants:
(i) so long as Investor beneficially owns the Note, Company will timely file on the applicable deadline all reports required to
be filed with the SEC pursuant to Sections 13 or 15(d) of the 1934 Act, and will take all reasonable action under its control
to ensure that adequate current public information with respect to Company, as required in accordance with Rule 144 of the 1933
Act, is publicly available, and will not terminate its status as an issuer required to file reports under the 1934 Act even if
the 1934 Act or the rules and regulations thereunder would permit such termination; (ii) the Common Stock shall be listed or quoted
for trading on any of (a) NYSE, (b) NASDAQ, (c) OTCQX, or (d) OTCQB; (iii) trading in Company’s Common Stock will not be
suspended, halted, chilled, frozen, reach zero bid or otherwise cease trading on Company’s principal trading market for
a period of five (5) consecutive Trading Days (as defined in the Note); (iv) Company will not, to the best of its knowledge after
due inquiry, enter into any kind of financing transaction with John Kirkland or any entity affiliated with or controlled by John
Kirkland without Investor’s prior written consent, which consent may be granted or withheld in Investor’s sole and
absolute discretion; and (v) Company will not issue any debt instrument or incur any debt other than trade payables in the ordinary
course of business without Investor’s prior written consent, which consent may be granted or withheld in Investor’s
sole discretion; provided, however, that no consent is required in connection with the issuance of any debt instrument to any
party that is affiliated with the Investor.

 

5. Conditions
to Company’s Obligation to Sell. The obligation of Company hereunder to issue and sell the Note to Investor at the Closing
is subject to the satisfaction, on or before the Closing Date, of each of the following conditions:

 

5.1. Investor
shall have executed this Agreement and delivered the same to Company.

 

5.2. Investor
shall have delivered the Purchase Price to Company in accordance with Section 1.2 above.

 

6. Conditions
to Investor’s Obligation to Purchase. The obligation of Investor hereunder to purchase the Note at the Closing is subject
to the satisfaction, on or before the Closing Date, of each of the following conditions, provided that these conditions are for
Investor’s sole benefit and may be waived by Investor at any time in its sole discretion:

 

6.1. Company
shall have executed this Agreement and the Note and delivered the same to Investor.

 

6.2. Company
shall have delivered to Investor a fully executed Secretary’s Certificate substantially in the form attached hereto as Exhibit
B evidencing Company’s approval of the Transaction Documents.

 

6.3. Company
shall have delivered to Investor fully executed copies of all other Transaction Documents required to be executed by Company herein
or therein.

 

7. Right
of First Refusal. If at any time while the Note is outstanding, Company intends to enter into a financing with a Person pursuant
to which it will issue Company securities that (A) have or may have conversion rights of any kind, contingent, conditional or
otherwise, in which the number of shares that may be issued pursuant to such conversion right varies with the market price of
the Common Stock, or (B) are or may become convertible into Common Stock (including without limitation convertible debt, warrants
or convertible preferred stock), with a conversion price that varies with the market price of the Common Stock, even if such security
only becomes convertible following an event of default, the passage of time, or another trigger event or condition (such a financing,
a “Future Offering”), then Company must first offer such opportunity to Investor to provide such financing
to Company on the same terms as each respective Person’s term no later than five (5) Trading Days immediately prior to the
Trading Day of the expected announcement of the Future Offering. Should Investor be unwilling or unable to provide such financing
to Company within five (5) Trading Days from Investor’s receipt of notice of the Future Offering from Company, then Company
may obtain such financing from that respective Person upon the exact same terms and conditions offered by Company to Investor,
which transaction must be completed within 30 days after the date of the notice. If Company does not receive the financing from
the respective Person within 30 days after the date of the respective notice, then Company must again offer the financing opportunity
to Investor as described above, and the process detailed above shall be repeated. For avoidance of doubt, the issuance of shares
of Common Stock under, pursuant to, in exchange for or in connection with any contract or instrument, whether convertible or not,
is deemed a Future Offering for purposes hereof if the number of shares of Common Stock to be issued is based upon or related
in any way to the market price of the Common Stock, including, but not limited to, Common Stock issued in connection with a Section
3(a)(9) exchange, a Section 3(a)(10) settlement, or any other similar settlement or exchange. This Section 7 shall not apply to
an Exempt Issuance (as defined below) or to a registered offering made pursuant to a registration statement on Form S-1 or Form
S-3.

 

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8. Participation
in Future Offering.

 

8.1. So
long as the Note is outstanding, upon any offer of securities by Company with any term or condition more favorable to the holder
of such security or with a term in favor of the holder of such security that was not similarly provided to Investor in the Transaction
Documents (“Favorable Transaction”), then Company shall notify Investor of such additional or more Favorable
Transaction and, Investor may, at its option, have the right to participate in such Favorable Transaction on the same terms and
conditions in an amount up to the aggregate amount then outstanding under the Note. The types of terms contained in another security
that may be more favorable to the holder of such security include, but are not limited to, terms addressing conversion rights,
conversion discounts, conversion lookback periods, interest rates, original issue discounts, stock sale price, conversion price
per share, warrant coverage, warrant exercise price, and anti-dilution/conversion and exercise price resets.

 

8.2. Notwithstanding
the foregoing, this Section 8 shall not apply in respect of an Exempt Issuance, a transaction under Section 3(a)(10) of 1933 Act,
a registered offering made pursuant to a registration statement on Form S-1 or Form S-3, or in connection with the satisfaction
of outstanding trade payables. “Exempt Issuance” means the issuance of (a) shares of Common Stock or any securities
of Company which would entitle the holder thereof to acquire at any time Common Stock, including, without limitation, any debt,
preferred stock, right, option, warrant or other instrument that is at any time convertible into or exercisable or exchangeable
for, or otherwise entitles the holder thereof to receive, Common Stock (“Common Stock Equivalents”), to consultants,
employees, officers or directors of the Company pursuant to any stock or option plan duly adopted for such purpose or as approved
by the Board of Directors or a majority of the members of a committee of directors established for such purpose for services rendered
to the Company; (b) securities upon the exercise or exchange of or conversion of the Note issued hereunder and/or other securities
exercisable or exchangeable for or convertible into shares of Common Stock issued and outstanding on the date of this Agreement,
provided that such securities have not been amended since the date of this Agreement to increase the number of such securities
or to decrease the exercise price, floor price, exchange price or conversion price of such securities (other than in connection
with stock splits or combinations) or to extend the term of such securities; and (c) securities issued pursuant to acquisitions,
dispositions or strategic transactions approved by a majority of the disinterested directors of the Company.

 

9. Miscellaneous.
The provisions set forth in this Section 9 shall apply to this Agreement, as well as all other Transaction Documents as if these
terms were fully set forth therein; provided, however, that in the event there is a conflict between any provision set forth in
this Section 9 and any provision in any other Transaction Document, the provision in such other Transaction Document shall govern.

 

9.1. Certain
Capitalized Terms. To the extent any capitalized term used in any Transaction Document is defined in any other Transaction
Document (as noted therein), such capitalized term shall remain applicable in the Transaction Document in which it is so used
even if the other Transaction Document (wherein such term is defined) has been released, satisfied, or is otherwise cancelled
or terminated.

 

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9.2. Arbitration
of Claims. The parties shall submit all Claims (as defined in Exhibit C) arising under this Agreement or any other
Transaction Document or any other agreement between the parties and their affiliates or any Claim relating to the relationship
of the parties to binding arbitration pursuant to the arbitration provisions set forth in Exhibit C attached hereto (the
“Arbitration Provisions”). For the avoidance of doubt, the parties agree that the injunction described in Section
9.4 below may be pursued in an arbitration that is separate and apart from any other arbitration regarding other Claims arising
under the Transaction Documents. The parties hereby acknowledge and agree that the Arbitration Provisions are unconditionally
binding on the parties hereto and are severable from all other provisions of this Agreement. By executing this Agreement, Company
represents, warrants and covenants that Company has reviewed the Arbitration Provisions carefully, consulted with legal counsel
about such provisions (or waived its right to do so), understands that the Arbitration Provisions are intended to allow for the
expeditious and efficient resolution of any dispute hereunder, agrees to the terms and limitations set forth in the Arbitration
Provisions, and that Company will not take a position contrary to the foregoing representations. Company acknowledges and agrees
that Investor may rely upon the foregoing representations and covenants of Company regarding the Arbitration Provisions.

 

9.3. Governing
Law; Venue. This Agreement shall be construed and enforced in accordance with, and all questions concerning the construction,
validity, interpretation and performance of this Agreement shall be governed by, the internal laws of the State of Utah, without
giving effect to any choice of law or conflict of law provision or rule (whether of the State of Utah or any other jurisdiction)
that would cause the application of the laws of any jurisdiction other than the State of Utah. Each party consents to and expressly
agrees that the exclusive venue for arbitration of any dispute arising out of or relating to any Transaction Document or the relationship
of the parties or their affiliates shall be in Salt Lake County, Utah. Without modifying the parties’ obligations to resolve
disputes hereunder pursuant to the Arbitration Provisions, for any litigation arising in connection with any of the Transaction
Documents (and notwithstanding the terms (specifically including any governing law and venue terms) of any transfer agent services
agreement or other agreement between the Company’s transfer agent (the “Transfer Agent”) and Company,
such litigation specifically includes, without limitation any action between or involving Company and the Transfer Agent or otherwise
related to Investor in any way (specifically including, without limitation, any action where Company seeks to obtain an injunction,
temporary restraining order, or otherwise prohibit the Transfer Agent from issuing shares of Common Stock to Investor for any
reason)), each party hereto hereby (i) consents to and expressly submits to the exclusive personal jurisdiction of any state or
federal court sitting in Salt Lake County, Utah, (ii) expressly submits to the exclusive venue of any such court for the purposes
hereof, (iii) agrees to not bring any such action (specifically including, without limitation, any action where Company seeks
to obtain an injunction, temporary restraining order, or otherwise prohibit the Transfer Agent from issuing shares of Common Stock
to Investor for any reason) outside of any state or federal court sitting in Salt Lake County, Utah, and (iv) waives any claim
of improper venue and any claim or objection that such courts are an inconvenient forum or any other claim, defense or objection
to the bringing of any such proceeding in such jurisdiction or to any claim that such venue of the suit, action or proceeding
is improper. Finally, Company covenants and agrees to name Investor as a party in interest in, and provide written notice to Investor
in accordance with Section 9.12 below prior to bringing or filing, any action (including without limitation any filing or action
against any person or entity that is not a party to this Agreement, including without limitation the Transfer Agent) that is related
in any way to the Transaction Documents or any transaction contemplated herein or therein, including without limitation any action
brought by Company to enjoin or prevent the issuance of any shares of Common Stock to Investor by the Transfer Agent, and further
agrees to timely name Investor as a party to any such action. Company acknowledges that the governing law and venue provisions
set forth in this Section 9.3 are material terms to induce Investor to enter into the Transaction Documents and that but for Company’s
agreements set forth in this Section 9.3 Investor would not have entered into the Transaction Documents.

 

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9.4. Specific
Performance. Company acknowledges and agrees Investor may suffer irreparable harm in the event that Company fails to perform
any material provision of this Agreement or any of the other Transaction Documents in accordance with its specific terms. It is
accordingly agreed that Investor shall be entitled to one or more injunctions to prevent or cure breaches of the provisions of
this Agreement or such other Transaction Document and to enforce specifically the terms and provisions hereof or thereof, this
being in addition to any other remedy to which the Investor may be entitled under the Transaction Documents, at law or in equity.
Company specifically agrees that following an Event of Default (as defined in the Note) under the Note, Investor shall have the
right to seek and receive injunctive relief from a court or an arbitrator prohibiting Company from issuing any of its Common Stock
or preferred stock to any party unless the Note is being paid in full simultaneously with such issuance. For the avoidance of
doubt, in the event Investor seeks to obtain an injunction from a court or an arbitrator against Company or specific performance
of any provision of any Transaction Document, such action shall not be a waiver of any right of Investor under any Transaction
Document, at law, or in equity, including without limitation its rights to arbitrate any Claim pursuant to the terms of the Transaction
Documents, nor shall Investor’s pursuit of an injunction prevent Investor, under the doctrines of claim preclusion, issues
preclusion, res judicata or other similar legal doctrines, from pursuing other Claims in the future in a separate arbitration.

 

9.5. Counterparts.
Each Transaction Document may be executed in any number of counterparts, each of which shall be deemed an original, but all of
which together shall constitute one instrument. The parties hereto confirm that any electronic copy of another party’s executed
counterpart of a Transaction Document (or such party’s signature page thereof) will be deemed to be an executed original
thereof.

 

9.6. Document
Imaging. Investor shall be entitled, in its sole discretion, to image or make copies of all or any selection of the agreements,
instruments, documents, and items and records governing, arising from or relating to any of Company’s loans, including,
without limitation, this Agreement and the other Transaction Documents, and Investor may destroy or archive the paper originals. The
parties hereto (i) waive any right to insist or require that Investor produce paper originals, (ii) agree that such images shall
be accorded the same force and effect as the paper originals, (iii) agree that Investor is entitled to use such images in lieu
of destroyed or archived originals for any purpose, including as admissible evidence in any demand, presentment or other proceedings,
and (iv) further agree that any executed facsimile (faxed), scanned, emailed, or other imaged copy of this Agreement or any other
Transaction Document shall be deemed to be of the same force and effect as the original manually executed document.

 

9.7. Headings.
The headings of this Agreement are for convenience of reference only and shall not form part of, or affect the interpretation
of, this Agreement.

 

9.8. Severability.
In the event that any provision of this Agreement is invalid or unenforceable under any applicable statute or rule of law, then
such provision shall be deemed inoperative to the extent that it may conflict therewith and shall be deemed modified to conform
to such statute or rule of law. Any provision hereof which may prove invalid or unenforceable under any law shall not affect the
validity or enforceability of any other provision hereof.

 

9.9. Entire
Agreement. This Agreement, together with the other Transaction Documents, contains 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 Company
nor Investor makes any representation, warranty, covenant or undertaking with respect to such matters. For the avoidance of doubt,
all prior term sheets or other documents between Company and Investor, or any affiliate thereof, related to the transactions contemplated
by the Transaction Documents (collectively, “Prior Agreements”), that may have been entered into between Company
and Investor, or any affiliate thereof, are hereby null and void and deemed to be replaced in their entirety by the Transaction
Documents. To the extent there is a conflict between any term set forth in any Prior Agreement and the term(s) of the Transaction
Documents, the Transaction Documents shall govern.

 

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9.10. No
Reliance. Company acknowledges and agrees that neither Investor nor any of its officers, directors, members, managers, representatives
or agents has made any representations or warranties to Company or any of its officers, directors, representatives, agents or
employees except as expressly set forth in the Transaction Documents and, in making its decision to enter into the transactions
contemplated by the Transaction Documents, Company is not relying on any representation, warranty, covenant or promise of Investor
or its officers, directors, members, managers, agents or representatives other than as set forth in the Transaction Documents.

 

9.11. Amendments.
No provision of this Agreement may be waived or amended other than by an instrument in writing signed by both parties hereto.

 

9.12. Notices.
Any notice required or permitted hereunder shall be given in writing (unless otherwise specified herein) and shall be deemed effectively
given on the earliest of: (i) the date delivered, if delivered by personal delivery as against written receipt therefor or by
email to an executive officer, or by facsimile (with successful transmission confirmation), (ii) the earlier of the date delivered
or the third Trading Day after deposit, postage prepaid, in the United States Postal Service by certified mail, or (iii) the earlier
of the date delivered or the third Trading Day after mailing by express courier, with delivery costs and fees prepaid, in each
case, addressed to each of the other parties thereunto entitled at the following addresses (or at such other addresses as such
party may designate by five (5) calendar days’ advance written notice similarly given to each of the other parties hereto):

 

If
to Company:

 

Inpixon

Attn:
Nadir Ali

2479
East Bayshore Road, Suite 195

Palo
Alto, California 94303

Nadir.Ali@inpixon.com

 

If
to Investor:

 

Iliad
Research and Trading, L.P.

Attn:
John Fife

303
East Wacker Drive, Suite 1040

Chicago,
Illinois 60601

jfife@chicagoventure.com

 

    8

     

    

 

With
a copy to (which copy shall not constitute notice):

 

Hansen
Black Anderson Ashcraft PLLC

Attn:
Jonathan Hansen

3051
West Maple Loop Drive, Suite 325

Lehi,
Utah 84043

jhansen@hbaa.law

 

9.13. Successors
and Assigns. This Agreement or any of the severable rights and obligations inuring to the benefit of or to be performed by
Investor hereunder may be assigned by Investor to a third party, including its affiliates, in whole or in part, without the need
to obtain Company’s consent thereto. Company may not assign its rights or obligations under this Agreement or delegate its
duties hereunder without the prior written consent of Investor.

 

9.14. Survival.
The representations and warranties of Company and the agreements and covenants set forth in this Agreement shall survive the Closing
hereunder notwithstanding any due diligence investigation conducted by or on behalf of Investor. Company agrees to indemnify and
hold harmless Investor and all its officers, directors, employees, attorneys, and agents for loss or damage arising as a result
of or related to any breach or alleged breach by Company of any of its representations, warranties and covenants set forth in
this Agreement or any of its covenants and obligations under this Agreement, including advancement of expenses as they are incurred.

 

9.15. Further
Assurances. Each party 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 the 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.

 

9.16. Investor’s
Rights and Remedies Cumulative; Liquidated Damages. All rights, remedies, and powers conferred in this Agreement and the Transaction
Documents are cumulative and not exclusive of any other rights or remedies, and shall be in addition to every other right, power,
and remedy that Investor may have, whether specifically granted in this Agreement or any other Transaction Document, or existing
at law, in equity, or by statute, and any and all such rights and remedies may be exercised from time to time and as often and
in such order as Investor may deem expedient. The parties acknowledge and agree that upon Company’s failure to comply with
the provisions of the Transaction Documents, Investor’s damages would be uncertain and difficult (if not impossible) to
accurately estimate because of the parties’ inability to predict future interest rates and future share prices, Investor’s
increased risk, and the uncertainty of the availability of a suitable substitute investment opportunity for Investor, among other
reasons. Accordingly, any fees, charges, and default interest due under the Note and the other Transaction Documents are intended
by the parties to be, and shall be deemed, liquidated damages. The parties agree that such liquidated damages are a reasonable
estimate of Investor’s actual damages and not a penalty, and shall not be deemed in any way to limit any other right or
remedy Investor may have hereunder, at law or in equity. The parties acknowledge and agree that under the circumstances existing
at the time this Agreement is entered into, such liquidated damages are fair and reasonable and are not penalties. All fees, charges,
and default interest provided for in the Transaction Documents are agreed to by the parties to be based upon the obligations and
the risks assumed by the parties as of the Closing Date and are consistent with investments of this type. The liquidated damages
provisions of the Transaction Documents shall not limit or preclude a party from pursuing any other remedy available at law or
in equity; provided, however, that the liquidated damages provided for in the Transaction Documents are intended to be
in lieu of actual damages.

 

    9

     

    

 

9.17. Attorneys’
Fees and Cost of Collection. In the event of any arbitration or action at law or in equity to enforce or interpret the terms
of this Agreement or any of the other Transaction Documents, the parties agree that the party who is awarded the most money (which,
for the avoidance of doubt, shall be determined without regard to any statutory fines, penalties, fees, or other charges awarded
to any party) shall be deemed the prevailing party for all purposes and shall therefore be entitled to an additional award of
the full amount of the reasonable attorneys’ fees, deposition costs, and expenses paid by such prevailing party in connection
with arbitration or litigation without reduction or apportionment based upon the individual claims or defenses giving rise to
the fees and expenses. Nothing herein shall restrict or impair an arbitrator’s or a court’s power to award fees and
expenses for frivolous or bad faith pleading. If (i) the Note is placed in the hands of an attorney for collection or enforcement
prior to commencing arbitration or legal proceedings, or is collected or enforced through any arbitration or legal proceeding,
or Investor otherwise takes action to collect amounts due under the Note or to enforce the provisions of the Note, or (ii) there
occurs any bankruptcy, reorganization, receivership of Company or other proceedings affecting Company’s creditors’
rights and involving a claim under the Note; then Company shall pay the costs incurred by Investor for such collection, enforcement
or action or in connection with such bankruptcy, reorganization, receivership or other proceeding, including, without limitation,
attorneys’ fees, expenses, deposition costs, and disbursements.

 

9.18. Waiver.
No waiver of any provision of this Agreement shall be effective unless it is in the form of a writing signed by the party granting
the waiver. No waiver of any provision or consent to any prohibited action shall constitute a waiver of any other provision or
consent to any other prohibited action, whether or not similar. No waiver or consent shall constitute a continuing waiver or consent
or commit a party to provide a waiver or consent in the future except to the extent specifically set forth in writing.

 

9.19. Waiver
of Jury Trial. EACH PARTY TO THIS AGREEMENT IRREVOCABLY WAIVES ANY AND ALL RIGHTS SUCH PARTY MAY HAVE TO DEMAND THAT ANY ACTION,
PROCEEDING OR COUNTERCLAIM ARISING OUT OF OR IN ANY WAY RELATED TO THIS AGREEMENT, ANY OTHER TRANSACTION DOCUMENT, OR THE RELATIONSHIPS
OF THE PARTIES HERETO BE TRIED BY JURY. THIS WAIVER EXTENDS TO ANY AND ALL RIGHTS TO DEMAND A TRIAL BY JURY ARISING UNDER COMMON
LAW OR ANY APPLICABLE STATUTE, LAW, RULE OR REGULATION. FURTHER, EACH PARTY HERETO ACKNOWLEDGES THAT SUCH PARTY IS KNOWINGLY AND
VOLUNTARILY WAIVING SUCH PARTY’S RIGHT TO DEMAND TRIAL BY JURY.

 

9.20. Time
is of the Essence. Time is expressly made of the essence with respect to each and every provision of this Agreement and the
other Transaction Documents.

 

9.21. No
Changes; Signature Pages. Company, as well as the person signing each Transaction Document on behalf of Company, represents
and warrants to Investor that it has not made any changes to this Agreement or any other Transaction Document except those that
have been conspicuously disclosed to Investor in a “redline” or similar draft of the applicable Transaction Document,
which clearly marks all changes Company has made to the applicable Transaction Document. Moreover, the versions of the Transaction
Documents signed by Company are the same versions Investor delivered to Company as being the “final” versions of the
Transaction Documents and Company represents and warrants that it has not made any changes to such “final” versions
of the Transaction Documents and that the versions Company signed are the same versions Investor delivered to it. In the event
Company has made any changes to any Transaction Document that are not conspicuously disclosed to Investor in a “redline”
or similar draft of the applicable Transaction Document and that have not been explicitly accepted and agreed upon by Investor,
Company acknowledges and agrees that any such changes shall not be considered part of the final document set. Finally, and in
furtherance of the foregoing, Company agrees and authorizes Investor to compile the “final” versions of the Transaction
Documents, which shall consist of Company’s executed signature pages for all Transaction Documents being applied to the
last set of the Transaction Documents that Investor delivered to Company, and Company agrees that such versions of the Transaction
Documents that have been collated by Investor shall be deemed to be the final versions of the Transaction Documents for all purposes.

 

9.22. Voluntary
Agreement. Company has carefully read this Agreement and each of the other Transaction Documents and has asked any questions
needed for Company to understand the terms, consequences and binding effect of this Agreement and each of the other Transaction
Documents and fully understand them. Company has had the opportunity to seek the advice of an attorney of Company’s choosing,
or has waived the right to do so, and is executing this Agreement and each of the other Transaction Documents voluntarily and
without any duress or undue influence by Investor or anyone else.

 

[Remainder
of page intentionally left blank; signature page follows]

    10

     

    

 

IN
WITNESS WHEREOF, the undersigned Investor and Company have caused this Agreement to be duly executed as of the date first above
written.

 

SUBSCRIPTION
AMOUNT:

 

	Principal Amount of Note:	 	$	6,465,000.00	 
	 	 	 	 	 
	Purchase Price:	 	$	5,000,000.00	 

 

	 	INVESTOR:
	 	 
	 	Iliad
    Research and Trading, L.P.
	 	 
	 	By:
    Iliad Management, LLC, its General Partner
	 	 
	 	 	By: Fife Trading, Inc., its Manager

 

	 	By:	/s/
    John M. Fife
	 	 	John
    M. Fife, President

 

	 	COMPANY:
	 	 
	 	Inpixon
	 	 
	 	By:	/s/ Nadir Ali

	 	Printed Name:	Nadir Ali

	 	Title:	Chief Executive Officer

 

[Signature
Page to Note Purchase Agreement]

 

     

     

    

 

ATTACHED
EXHIBITS:

 

	Exhibit
    A	Note
	Exhibit
    B	Secretary’s
    Certificate
	Exhibit
    C	Arbitration
    Provisions

 

     

     

    

 

EXHIBIT
A

 

NOTE

 

See
Exhibit 4.1 to the Current Report on Form 8-K filed with the SEC on March 20, 2020

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

     

     

    

 

EXHIBIT
B*

 

SECRETARY’S
CERTIFICATE

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

     

     

    

 

Exhibit
C

 

ARBITRATION
PROVISIONS

 

1. Dispute
Resolution. For purposes of this Exhibit C, the term “Claims” means any disputes, claims, demands,
causes of action, requests for injunctive relief, requests for specific performance, liabilities, damages, losses, or controversies
whatsoever arising from, related to, or connected with the transactions contemplated in the Transaction Documents and any communications
between the parties related thereto, including without limitation any claims of mutual mistake, mistake, fraud, misrepresentation,
failure of formation, failure of consideration, promissory estoppel, unconscionability, failure of condition precedent, rescission,
and any statutory claims, tort claims, contract claims, or claims to void, invalidate or terminate the Agreement (or these Arbitration
Provisions (defined below)) or any of the other Transaction Documents. For the avoidance of doubt, Investor’s pursuit of
an injunction or other Claim pursuant to these Arbitration Provisions or with a court will not later prevent Investor under the
doctrines of claim preclusion, issue preclusion, res judicata or other similar legal doctrines from pursuing other Claims in a
separate arbitration in the future. The parties to this Agreement (the “parties”) hereby agree that the Claims
may be arbitrated in one or more Arbitrations pursuant to these Arbitration Provisions. The parties hereby agree that the arbitration
provisions set forth in this Exhibit C (“Arbitration Provisions”) are binding on each of them. As a
result, any attempt to rescind the Agreement (or these Arbitration Provisions) or declare the Agreement (or these Arbitration
Provisions) or any other Transaction Document invalid or unenforceable for any reason is subject to these Arbitration Provisions.
These Arbitration Provisions shall also survive any termination or expiration of the Agreement. Any capitalized term not defined
in these Arbitration Provisions shall have the meaning set forth in the Agreement.

 

2. Arbitration.
Except as otherwise provided herein, all Claims must be submitted to arbitration (“Arbitration”) to be conducted
exclusively in Salt Lake County, Utah and pursuant to the terms set forth in these Arbitration Provisions. Subject to the arbitration
appeal right provided for in Paragraph 5 below (the “Appeal Right”), the parties agree that the award of the
arbitrator rendered pursuant to Paragraph 4 below (the “Arbitration Award”) shall be (a) final and binding
upon the parties, (b) the sole and exclusive remedy between them regarding any Claims, counterclaims, issues, or accountings presented
or pleaded to the arbitrator, and (c) promptly payable in United States dollars free of any tax, deduction or offset (with respect
to monetary awards). Subject to the Appeal Right, any costs or fees, including without limitation attorneys’ fees, incurred
in connection with or incident to enforcing the Arbitration Award shall, to the maximum extent permitted by law, be charged against
the party resisting such enforcement. The Arbitration Award shall include default interest (as defined or otherwise provided for
in the Note, “Default Interest”) (with respect to monetary awards) at the rate specified in the Note for Default
Interest both before and after the Arbitration Award. Judgment upon the Arbitration Award will be entered and enforced by any
state or federal court sitting in Salt Lake County, Utah.

 

3. The
Arbitration Act. The parties hereby incorporate herein the provisions and procedures set forth in the Utah Uniform Arbitration
Act, U.C.A. § 78B-11-101 et seq. (as amended or superseded from time to time, the “Arbitration Act”).
Notwithstanding the foregoing, pursuant to, and to the maximum extent permitted by, Section 105 of the Arbitration Act, in the
event of conflict or variation between the terms of these Arbitration Provisions and the provisions of the Arbitration Act, the
terms of these Arbitration Provisions shall control and the parties hereby waive or otherwise agree to vary the effect of all
requirements of the Arbitration Act that may conflict with or vary from these Arbitration Provisions.

 

4. Arbitration
Proceedings. Arbitration between the parties will be subject to the following:

 

4.1 Initiation
of Arbitration. Pursuant to Section 110 of the Arbitration Act, the parties agree that a party may initiate Arbitration by
giving written notice to the other party (“Arbitration Notice”) in the same manner that notice is permitted
under Section 9.12 of the Agreement; provided, however, that the Arbitration Notice may not be given by email or fax. Arbitration
will be deemed initiated as of the date that the Arbitration Notice is deemed delivered to such other party under Section 9.12
of the Agreement (the “Service Date”). After the Service Date, information may be delivered, and notices may
be given, by email or fax pursuant to Section 9.12 of the Agreement or any other method permitted thereunder. The Arbitration
Notice must describe the nature of the controversy, the remedies sought, and the election to commence Arbitration proceedings.
All Claims in the Arbitration Notice must be pleaded consistent with the Utah Rules of Civil Procedure.

 

     

     

    

 

4.2 Selection
and Payment of Arbitrator.

 

(a)
Within ten (10) calendar days after the Service Date, Investor shall select and submit to Company the names of three (3) arbitrators
that are designated as “neutrals” or qualified arbitrators by Utah ADR Services (http://www.utahadrservices.com) (such
three (3) designated persons hereunder are referred to herein as the “Proposed Arbitrators”). For the avoidance
of doubt, each Proposed Arbitrator must be qualified as a “neutral” with Utah ADR Services. Within five (5) calendar
days after Investor has submitted to Company the names of the Proposed Arbitrators, Company must select, by written notice to
Investor, one (1) of the Proposed Arbitrators to act as the arbitrator for the parties under these Arbitration Provisions. If
Company fails to select one of the Proposed Arbitrators in writing within such 5-day period, then Investor may select the arbitrator
from the Proposed Arbitrators by providing written notice of such selection to Company.

 

(b)
If Investor fails to submit to Company the Proposed Arbitrators within ten (10) calendar days after the Service Date pursuant
to subparagraph (a) above, then Company may at any time prior to Investor so designating the Proposed Arbitrators, identify the
names of three (3) arbitrators that are designated as “neutrals” or qualified arbitrators by Utah ADR Service by written
notice to Investor. Investor may then, within five (5) calendar days after Company has submitted notice of its Proposed Arbitrators
to Investor, select, by written notice to Company, one (1) of the Proposed Arbitrators to act as the arbitrator for the parties
under these Arbitration Provisions. If Investor fails to select in writing and within such 5-day period one (1) of the three (3)
Proposed Arbitrators selected by Company, then Company may select the arbitrator from its three (3) previously selected Proposed
Arbitrators by providing written notice of such selection to Investor.

 

(c)
If a Proposed Arbitrator chosen to serve as arbitrator declines or is otherwise unable to serve as arbitrator, then the party
that selected such Proposed Arbitrator may select one (1) of the other three (3) Proposed Arbitrators within three (3) calendar
days of the date the chosen Proposed Arbitrator declines or notifies the parties he or she is unable to serve as arbitrator. If
all three (3) Proposed Arbitrators decline or are otherwise unable to serve as arbitrator, then the arbitrator selection process
shall begin again in accordance with this Paragraph 4.2.

 

(d)
The date that the Proposed Arbitrator selected pursuant to this Paragraph 4.2 agrees in writing (including via email) delivered
to both parties to serve as the arbitrator hereunder is referred to herein as the “Arbitration Commencement Date”.
If an arbitrator resigns or is unable to act during the Arbitration, a replacement arbitrator shall be chosen in accordance with
this Paragraph 4.2 to continue the Arbitration. If Utah ADR Services ceases to exist or to provide a list of neutrals and there
is no successor thereto, then the arbitrator shall be selected under the then prevailing rules of the American Arbitration Association.

 

(e)
Subject to Paragraph 4.10 below, the cost of the arbitrator must be paid equally by both parties. Subject to Paragraph 4.10 below,
if one party refuses or fails to pay its portion of the arbitrator fee, then the other party can advance such unpaid amount (subject
to the accrual of Default Interest thereupon), with such amount being added to or subtracted from, as applicable, the Arbitration
Award.

 

4.3 Applicability
of Certain Utah Rules. The parties agree that the Arbitration shall be conducted generally in accordance with the Utah Rules
of Civil Procedure and the Utah Rules of Evidence. More specifically, the Utah Rules of Civil Procedure shall apply, without limitation,
to the filing of any pleadings, motions or memoranda, the conducting of discovery, and the taking of any depositions. The Utah
Rules of Evidence shall apply to any hearings, whether telephonic or in person, held by the arbitrator. Notwithstanding the foregoing,
it is the parties’ intent that the incorporation of such rules will in no event supersede these Arbitration Provisions.
In the event of any conflict between the Utah Rules of Civil Procedure or the Utah Rules of Evidence and these Arbitration Provisions,
these Arbitration Provisions shall control.

 

4.4 Answer
and Default. An answer and any counterclaims to the Arbitration Notice shall be required to be delivered to the party initiating
the Arbitration within twenty (20) calendar days after the Arbitration Commencement Date. If an answer is not delivered by the
required deadline, the arbitrator must provide written notice to the defaulting party stating that the arbitrator will enter a
default award against such party if such party does not file an answer within five (5) calendar days of receipt of such notice.
If an answer is not filed within the five (5) day extension period, the arbitrator must render a default award, consistent with
the relief requested in the Arbitration Notice, against a party that fails to submit an answer within such time period.

 

     

     

    

 

4.5 Related
Litigation. The party that delivers the Arbitration Notice to the other party shall have the option to also commence concurrent
legal proceedings with any state or federal court sitting in Salt Lake County, Utah (“Litigation Proceedings”),
subject to the following: (a) the complaint in the Litigation Proceedings is to be substantially similar to the claims set forth
in the Arbitration Notice, provided that an additional cause of action to compel arbitration will also be included therein, (b)
so long as the other party files an answer to the complaint in the Litigation Proceedings and an answer to the Arbitration Notice,
the Litigation Proceedings will be stayed pending an Arbitration Award (or Appeal Panel Award (defined below), as applicable)
hereunder, (c) if the other party fails to file an answer in the Litigation Proceedings or an answer in the Arbitration proceedings,
then the party initiating Arbitration shall be entitled to a default judgment consistent with the relief requested, to be entered
in the Litigation Proceedings, and (d) any legal or procedural issue arising under the Arbitration Act that requires a decision
of a court of competent jurisdiction may be determined in the Litigation Proceedings. Any award of the arbitrator (or of the Appeal
Panel (defined below)) may be entered in such Litigation Proceedings pursuant to the Arbitration Act.

 

4.6 Discovery.
Pursuant to Section 118(8) of the Arbitration Act, the parties agree that discovery shall be conducted as follows:

 

(a)
Written discovery will only be allowed if the likely benefits of the proposed written discovery outweigh the burden or expense
thereof, and the written discovery sought is likely to reveal information that will satisfy a specific element of a claim or defense
already pleaded in the Arbitration. The party seeking written discovery shall always have the burden of showing that all of the
standards and limitations set forth in these Arbitration Provisions are satisfied. The scope of discovery in the Arbitration proceedings
shall also be limited as follows:

 

(i) To
facts directly connected with the transactions contemplated by the Agreement.

 

(ii) To
facts and information that cannot be obtained from another source or in another manner that is more convenient, less burdensome
or less expensive than in the manner requested.

 

(b)
No party shall be allowed (i) more than fifteen (15) interrogatories (including discrete subparts), (ii) more than fifteen (15)
requests for admission (including discrete subparts), (iii) more than ten (10) document requests (including discrete subparts),
or (iv) more than three (3) depositions (excluding expert depositions) for a maximum of seven (7) hours per deposition. The costs
associated with depositions will be borne by the party taking the deposition. The party defending the deposition will submit a
notice to the party taking the deposition of the estimated attorneys’ fees that such party expects to incur in connection
with defending the deposition. If the party defending the deposition fails to submit an estimate of attorneys’ fees within
five (5) calendar days of its receipt of a deposition notice, then such party shall be deemed to have waived its right to the
estimated attorneys’ fees. The party taking the deposition must pay the party defending the deposition the estimated attorneys’
fees prior to taking the deposition, unless such obligation is deemed to be waived as set forth in the immediately preceding sentence.
If the party taking the deposition believes that the estimated attorneys’ fees are unreasonable, such party may submit the
issue to the arbitrator for a decision. All depositions will be taken in Utah.

 

(c)
All discovery requests (including document production requests included in deposition notices) must be submitted in writing to
the arbitrator and the other party. The party submitting the written discovery requests must include with such discovery requests
a detailed explanation of how the proposed discovery requests satisfy the requirements of these Arbitration Provisions and the
Utah Rules of Civil Procedure. The receiving party will then be allowed, within five (5) calendar days of receiving the proposed
discovery requests, to submit to the arbitrator an estimate of the attorneys’ fees and costs associated with responding
to such written discovery requests and a written challenge to each applicable discovery request. After receipt of an estimate
of attorneys’ fees and costs and/or challenge(s) to one or more discovery requests, consistent with subparagraph (c) above,
the arbitrator will within three (3) calendar days make a finding as to the likely attorneys’ fees and costs associated
with responding to the discovery requests and issue an order that (i) requires the requesting party to prepay the attorneys’
fees and costs associated with responding to the discovery requests, and (ii) requires the responding party to respond to the
discovery requests as limited by the arbitrator within twenty-five (25) calendar days of the arbitrator’s finding with respect
to such discovery requests. If a party entitled to submit an estimate of attorneys’ fees and costs and/or a challenge to
discovery requests fails to do so within such 5-day period, the arbitrator will make a finding that (A) there are no attorneys’
fees or costs associated with responding to such discovery requests, and (B) the responding party must respond to such discovery
requests (as may be limited by the arbitrator) within twenty-five (25) calendar days of the arbitrator’s finding with respect
to such discovery requests. Any party submitting any written discovery requests, including without limitation interrogatories,
requests for production subpoenas to a party or a third party, or requests for admissions, must prepay the estimated attorneys’
fees and costs, before the responding party has any obligation to produce or respond to the same, unless such obligation is deemed
waived as set forth above.

 

     

     

    

 

(d)
In order to allow a written discovery request, the arbitrator must find that the discovery request satisfies the standards set
forth in these Arbitration Provisions and the Utah Rules of Civil Procedure. The arbitrator must strictly enforce these standards.
If a discovery request does not satisfy any of the standards set forth in these Arbitration Provisions or the Utah Rules of Civil
Procedure, the arbitrator may modify such discovery request to satisfy the applicable standards, or strike such discovery request
in whole or in part.

 

(e)
Each party may submit expert reports (and rebuttals thereto), provided that such reports must be submitted within sixty (60) days
of the Arbitration Commencement Date. Each party will be allowed a maximum of two (2) experts. Expert reports must contain the
following: (i) a complete statement of all opinions the expert will offer at trial and the basis and reasons for them; (ii) the
expert’s name and qualifications, including a list of all the expert’s publications within the preceding ten (10)
years, and a list of any other cases in which the expert has testified at trial or in a deposition or prepared a report within
the preceding ten (10) years; and (iii) the compensation to be paid for the expert’s report and testimony. The parties are
entitled to depose any other party’s expert witness one (1) time for no more than four (4) hours. An expert may not testify
in a party’s case-in-chief concerning any matter not fairly disclosed in the expert report.

 

4.6 Dispositive
Motions. Each party shall have the right to submit dispositive motions pursuant Rule 12 or Rule 56 of the Utah Rules of Civil
Procedure (a “Dispositive Motion”). The party submitting the Dispositive Motion may, but is not required to,
deliver to the arbitrator and to the other party a memorandum in support (the “Memorandum in Support”) of the
Dispositive Motion. Within seven (7) calendar days of delivery of the Memorandum in Support, the other party shall deliver to
the arbitrator and to the other party a memorandum in opposition to the Memorandum in Support (the “Memorandum in Opposition”).
Within seven (7) calendar days of delivery of the Memorandum in Opposition, as applicable, the party that submitted the Memorandum
in Support shall deliver to the arbitrator and to the other party a reply memorandum to the Memorandum in Opposition (“Reply
Memorandum”). If the applicable party shall fail to deliver the Memorandum in Opposition as required above, or if the
other party fails to deliver the Reply Memorandum as required above, then the applicable party shall lose its right to so deliver
the same, and the Dispositive Motion shall proceed regardless.

 

4.7 Confidentiality.
All information disclosed by either party (or such party’s agents) during the Arbitration process (including without limitation
information disclosed during the discovery process or any Appeal (defined below)) shall be considered confidential in nature.
Each party agrees not to disclose any confidential information received from the other party (or its agents) during the Arbitration
process (including without limitation during the discovery process or any Appeal) unless (a) prior to or after the time of disclosure
such information becomes public knowledge or part of the public domain, not as a result of any inaction or action of the receiving
party or its agents, (b) such information is required by a court order, subpoena or similar legal duress to be disclosed if such
receiving party has notified the other party thereof in writing and given it a reasonable opportunity to obtain a protective order
from a court of competent jurisdiction prior to disclosure, or (c) such information is disclosed to the receiving party’s
agents, representatives and legal counsel on a need to know basis who each agree in writing not to disclose such information to
any third party. Pursuant to Section 118(5) of the Arbitration Act, the arbitrator is hereby authorized and directed to issue
a protective order to prevent the disclosure of privileged information and confidential information upon the written request of
either party.

 

4.8 Authorization;
Timing; Scheduling Order. Subject to all other portions of these Arbitration Provisions, the parties hereby authorize and
direct the arbitrator to take such actions and make such rulings as may be necessary to carry out the parties’ intent for
the Arbitration proceedings to be efficient and expeditious. Pursuant to Section 120 of the Arbitration Act, the parties hereby
agree that an Arbitration Award must be made within one hundred twenty (120) calendar days after the Arbitration Commencement
Date. The arbitrator is hereby authorized and directed to hold a scheduling conference within ten (10) calendar days after the
Arbitration Commencement Date in order to establish a scheduling order with various binding deadlines for discovery, expert testimony,
and the submission of documents by the parties to enable the arbitrator to render a decision prior to the end of such 120-day
period.

 

     

     

    

 

4.9 Relief.
The arbitrator shall have the right to award or include in the Arbitration Award (or in a preliminary ruling) any relief which
the arbitrator deems proper under the circumstances, including, without limitation, specific performance and injunctive relief,
provided that the arbitrator may not award exemplary or punitive damages.

 

4.10 Fees
and Costs. As part of the Arbitration Award, the arbitrator is hereby directed to require the losing party (the party being
awarded the least amount of money by the arbitrator, which, for the avoidance of doubt, shall be determined without regard to
any statutory fines, penalties, fees, or other charges awarded to any party) to (a) pay the full amount of any unpaid costs and
fees of the Arbitration, and (b) reimburse the prevailing party for all reasonable attorneys’ fees, arbitrator costs and
fees, deposition costs, other discovery costs, and other expenses, costs or fees paid or otherwise incurred by the prevailing
party in connection with the Arbitration.

 

5. Arbitration
Appeal.

 

5.1 Initiation
of Appeal. Following the entry of the Arbitration Award, either party (the “Appellant”) shall have a period
of thirty (30) calendar days in which to notify the other party (the “Appellee”), in writing, that the Appellant
elects to appeal (the “Appeal”) the Arbitration Award (such notice, an “Appeal Notice”)
to a panel of arbitrators as provided in Paragraph 5.2 below. The date the Appellant delivers an Appeal Notice to the Appellee
is referred to herein as the “Appeal Date”. The Appeal Notice must be delivered to the Appellee in accordance
with the provisions of Paragraph 4.1 above with respect to delivery of an Arbitration Notice. In addition, together with delivery
of the Appeal Notice to the Appellee, the Appellant must also pay for (and provide proof of such payment to the Appellee together
with delivery of the Appeal Notice) a bond in the amount of 110% of the sum the Appellant owes to the Appellee as a result of
the Arbitration Award the Appellant is appealing. In the event an Appellant delivers an Appeal Notice to the Appellee (together
with proof of payment of the applicable bond) in compliance with the provisions of this Paragraph 5.1, the Appeal will occur as
a matter of right and, except as specifically set forth herein, will not be further conditioned. In the event a party does not
deliver an Appeal Notice (along with proof of payment of the applicable bond) to the other party within the deadline prescribed
in this Paragraph 5.1, such party shall lose its right to appeal the Arbitration Award. If no party delivers an Appeal Notice
(along with proof of payment of the applicable bond) to the other party within the deadline described in this Paragraph 5.1, the
Arbitration Award shall be final. The parties acknowledge and agree that any Appeal shall be deemed part of the parties’
agreement to arbitrate for purposes of these Arbitration Provisions and the Arbitration Act.

 

5.2 Selection
and Payment of Appeal Panel. In the event an Appellant delivers an Appeal Notice to the Appellee (together with proof of payment
of the applicable bond) in compliance with the provisions of Paragraph 5.1 above, the Appeal will be heard by a three (3) person
arbitration panel (the “Appeal Panel”).

 

(a)
Within ten (10) calendar days after the Appeal Date, the Appellee shall select and submit to the Appellant the names of five
(5) arbitrators that are designated as “neutrals” or qualified arbitrators by Utah ADR Services (http://www.utahadrservices.com)
(such five (5) designated persons hereunder are referred to herein as the “Proposed Appeal Arbitrators”). For
the avoidance of doubt, each Proposed Appeal Arbitrator must be qualified as a “neutral” with Utah ADR Services, and
shall not be the arbitrator who rendered the Arbitration Award being appealed (the “Original Arbitrator”).
Within five (5) calendar days after the Appellee has submitted to the Appellant the names of the Proposed Appeal Arbitrators,
the Appellant must select, by written notice to the Appellee, three (3) of the Proposed Appeal Arbitrators to act as the members
of the Appeal Panel. If the Appellant fails to select three (3) of the Proposed Appeal Arbitrators in writing within such 5-day
period, then the Appellee may select such three (3) arbitrators from the Proposed Appeal Arbitrators by providing written notice
of such selection to the Appellant.

 

(b)
If the Appellee fails to submit to the Appellant the names of the Proposed Appeal Arbitrators within ten (10) calendar days
after the Appeal Date pursuant to subparagraph (a) above, then the Appellant may at any time prior to the Appellee so designating
the Proposed Appeal Arbitrators, identify the names of five (5) arbitrators that are designated as “neutrals” or qualified
arbitrators by Utah ADR Service (none of whom may be the Original Arbitrator) by written notice to the Appellee. The Appellee
may then, within five (5) calendar days after the Appellant has submitted notice of its selected arbitrators to the Appellee,
select, by written notice to the Appellant, three (3) of such selected arbitrators to serve on the Appeal Panel. If the Appellee
fails to select in writing within such 5-day period three (3) of the arbitrators selected by the Appellant to serve as the members
of the Appeal Panel, then the Appellant may select the three (3) members of the Appeal Panel from the Appellant’s list of
five (5) arbitrators by providing written notice of such selection to the Appellee.

 

     

     

    

 

(c)
If a selected Proposed Appeal Arbitrator declines or is otherwise unable to serve, then the party that selected such Proposed
Appeal Arbitrator may select one (1) of the other five (5) designated Proposed Appeal Arbitrators within three (3) calendar days
of the date a chosen Proposed Appeal Arbitrator declines or notifies the parties he or she is unable to serve as an arbitrator.
If at least three (3) of the five (5) designated Proposed Appeal Arbitrators decline or are otherwise unable to serve, then the
Proposed Appeal Arbitrator selection process shall begin again in accordance with this Paragraph 5.2; provided, however,
that any Proposed Appeal Arbitrators who have already agreed to serve shall remain on the Appeal Panel.

 

(d)
The date that all three (3) Proposed Appeal Arbitrators selected pursuant to this Paragraph 5.2 agree in writing (including
via email) delivered to both the Appellant and the Appellee to serve as members of the Appeal Panel hereunder is referred to
herein as the “Appeal Commencement Date”. No later than five (5) calendar days after the Appeal
Commencement Date, the Appellee shall designate in writing (including via email) to the Appellant and the Appeal Panel the
name of one (1) of the three (3) members of the Appeal Panel to serve as the lead arbitrator in the Appeal proceedings. Each
member of the Appeal Panel shall be deemed an arbitrator for purposes of these Arbitration Provisions and the Arbitration
Act, provided that, in conducting the Appeal, the Appeal Panel may only act or make determinations upon the approval or vote
of no less than the majority vote of its members, as announced or communicated by the lead arbitrator on the Appeal Panel. If
an arbitrator on the Appeal Panel ceases or is unable to act during the Appeal proceedings, a replacement arbitrator shall be
chosen in accordance with Paragraph 5.2 above to continue the Appeal as a member of the Appeal Panel. If Utah ADR
Services ceases to exist or to provide a list of neutrals, then the arbitrators for the Appeal Panel shall be selected under
the then prevailing rules of the American Arbitration Association.

 

(d)
Subject to Paragraph 5.7 below, the cost of the Appeal Panel must be paid entirely by the Appellant.

 

5.3 Appeal
Procedure. The Appeal will be deemed an appeal of the entire Arbitration Award. In conducting the Appeal, the Appeal Panel
shall conduct a de novo review of all Claims described or otherwise set forth in the Arbitration Notice. Subject to the foregoing
and all other provisions of this Paragraph 5, the Appeal Panel shall conduct the Appeal in a manner the Appeal Panel considers
appropriate for a fair and expeditious disposition of the Appeal, may hold one or more hearings and permit oral argument, and
may review all previous evidence and discovery, together with all briefs, pleadings and other documents filed with the Original
Arbitrator (as well as any documents filed with the Appeal Panel pursuant to Paragraph 5.4(a) below). Notwithstanding the foregoing,
in connection with the Appeal, the Appeal Panel shall not permit the parties to conduct any additional discovery or raise any
new Claims to be arbitrated, shall not permit new witnesses or affidavits, and shall not base any of its findings or determinations
on the Original Arbitrator’s findings or the Arbitration Award.

 

5.4 Timing.

 

(a) Within
seven (7) calendar days of the Appeal Commencement Date, the Appellant (i) shall deliver or cause to be delivered to the Appeal
Panel copies of the Appeal Notice, all discovery conducted in connection with the Arbitration, and all briefs, pleadings and other
documents filed with the Original Arbitrator (which material Appellee shall have the right to review and supplement if necessary),
and (ii) may, but is not required to, deliver to the Appeal Panel and to the Appellee a Memorandum in Support of the Appellant’s
arguments concerning or position with respect to all Claims, counterclaims, issues, or accountings presented or pleaded in the
Arbitration. Within seven (7) calendar days of the Appellant’s delivery of the Memorandum in Support, as applicable, the
Appellee shall deliver to the Appeal Panel and to the Appellant a Memorandum in Opposition to the Memorandum in Support. Within
seven (7) calendar days of the Appellee’s delivery of the Memorandum in Opposition, as applicable, the Appellant shall deliver
to the Appeal Panel and to the Appellee a Reply Memorandum to the Memorandum in Opposition. If the Appellant shall fail to substantially
comply with the requirements of clause (i) of this subparagraph (a), the Appellant shall lose its right to appeal the Arbitration
Award, and the Arbitration Award shall be final. If the Appellee shall fail to deliver the Memorandum in Opposition as required
above, or if the Appellant shall fail to deliver the Reply Memorandum as required above, then the Appellee or the Appellant, as
the case may be, shall lose its right to so deliver the same, and the Appeal shall proceed regardless.

 

     

     

    

 

(b)
 Subject to subparagraph (a) above, the parties hereby agree that the Appeal must be
heard by the Appeal Panel within thirty (30) calendar days of the Appeal Commencement Date, and that the Appeal Panel must render
its decision within thirty (30) calendar days after the Appeal is heard (and in no event later than sixty (60) calendar days after
the Appeal Commencement Date).

 

5.5 Appeal
Panel Award. The Appeal Panel shall issue its decision (the “Appeal Panel Award”) through the lead arbitrator
on the Appeal Panel. Notwithstanding any other provision contained herein, the Appeal Panel Award shall (a) supersede in its entirety
and make of no further force or effect the Arbitration Award (provided that any protective orders issued by the Original Arbitrator
shall remain in full force and effect), (b) be final and binding upon the parties, with no further rights of appeal, (c) be the
sole and exclusive remedy between the parties regarding any Claims, counterclaims, issues, or accountings presented or pleaded
in the Arbitration, and (d) be promptly payable in United States dollars free of any tax, deduction or offset (with respect to
monetary awards). Any costs or fees, including without limitation attorneys’ fees, incurred in connection with or incident
to enforcing the Appeal Panel Award shall, to the maximum extent permitted by law, be charged against the party resisting such
enforcement. The Appeal Panel Award shall include Default Interest (with respect to monetary awards) at the rate specified in
the Note for Default Interest both before and after the Arbitration Award. Judgment upon the Appeal Panel Award will be entered
and enforced by a state or federal court sitting in Salt Lake County, Utah.

 

5.6 Relief.
The Appeal Panel shall have the right to award or include in the Appeal Panel Award any relief which the Appeal Panel deems
proper under the circumstances, including, without limitation, specific performance and injunctive relief, provided that the Appeal
Panel may not award exemplary or punitive damages.

 

5.7 Fees
and Costs. As part of the Appeal Panel Award, the Appeal Panel is hereby directed to require the losing party (the party being
awarded the least amount of money by the arbitrator, which, for the avoidance of doubt, shall be determined without regard to
any statutory fines, penalties, fees, or other charges awarded to any party) to (a) pay the full amount of any unpaid costs and
fees of the Arbitration and the Appeal Panel, and (b) reimburse the prevailing party (the party being awarded the most amount
of money by the Appeal Panel, which, for the avoidance of doubt, shall be determined without regard to any statutory fines, penalties,
fees, or other charges awarded to any part) the reasonable attorneys’ fees, arbitrator and Appeal Panel costs and fees,
deposition costs, other discovery costs, and other expenses, costs or fees paid or otherwise incurred by the prevailing party
in connection with the Arbitration (including without limitation in connection with the Appeal).

 

6.
 Miscellaneous.

 

6.1 Severability.
If any part of these Arbitration Provisions is found to violate or be illegal under applicable law, then such provision shall
be modified to the minimum extent necessary to make such provision enforceable under applicable law, and the remainder of the
Arbitration Provisions shall remain unaffected and in full force and effect.

 

6.2 Governing
Law. These Arbitration Provisions shall be governed by the laws of the State of Utah without regard to the conflict of laws
principles therein.

 

6.3 Interpretation.
The headings of these Arbitration Provisions are for convenience of reference only and shall not form part of, or affect the interpretation
of, these Arbitration Provisions.

 

6.4 Waiver.
No waiver of any provision of these Arbitration Provisions shall be effective unless it is in the form of a writing signed by
the party granting the waiver.

 

6.5 Time
is of the Essence. Time is expressly made of the essence with respect to each and every provision of these Arbitration Provisions.

 

[Remainder
of page intentionally left blank]EX-10.1

 Exhibit 10.1 

EMPLOYMENT AGREEMENT 

This Employment Agreement (this “Agreement”), is made by and between Cumulus Media Inc., a Delaware corporation (the
“Company”), and Francisco J. Lopez-Balboa (the “Executive”). 
 W I T N E S S E T H: 

WHEREAS, the Company desires to employ the Executive in the capacity of Executive Vice President and Chief Financial Officer and the Employee
desires to be so employed pursuant to the terms of this Agreement; 
 NOW, THEREFORE, in consideration of the foregoing and the mutual
representations, warranties, covenants, and agreements contained herein and other good and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, and subject to the terms and conditions set forth below, the Company and
the Executive hereby agree as follows: 
 1. Effectiveness. This Agreement is effective as of March 23, 2020 (the “Start
Date”). 
 2. Term of Employment. The Executive’s employment under the terms and conditions of this Agreement shall commence
on the Start Date and shall continue until March 23, 2023 (the “Initial Term”). The term of the Executive’s employment under this Agreement shall be automatically extended for an additional one (1) year period upon the
expiration of the Initial Term and on each subsequent anniversary thereof (each, a “Renewal Term”). The Initial Term and any Renewal Term are collectively referred to as the “Term,” and the Term shall continue as
described in this paragraph unless either the Company or the Executive provides written notice to the other no less than one hundred and eighty (180) days prior to the scheduled expiration of the Term that the Term shall not be so extended
(“Non-Renewal Notice”). Notwithstanding anything in this Agreement to the contrary and subject to the terms of Section 6 hereof, the Executive shall be an at-will employee of the Company. 
 3. Position and Duties. 

(a) During the Term, the Executive shall, pursuant to the terms of this Agreement, serve as Executive Vice President and Chief Financial
Officer of the Company, and shall report solely and directly to the Chief Executive Officer of the Company (the “Chief Financial Officer”). The Executive shall be based in New York, New York; provided, that the Executive understands
and agrees that he shall be required to travel for business reasons, including to the Company’s headquarters in Atlanta, Georgia and to other Company locations. 

(b) During the Employment Period, Executive shall devote Executive’s full business time, energy, ability, attention and skill to
Employee’s employment hereunder. Executive agrees that, during the Employment Period, Executive will not provide services as an employee, consultant, independent contractor or otherwise to any individual or entity without the written consent of
the Company. The Executive shall (i) have all authorities, duties and responsibilities customarily exercised by an individual serving as Executive Vice President and Chief Financial Officer of a company the size and nature of the Company;
(ii) be assigned no duties or responsibilities that are materially inconsistent with, or that materially impair his ability to discharge, the foregoing duties and responsibilities; and (iii) have such additional duties and
responsibilities, consistent with the foregoing, as the Chief Executive Officer of the Company may from time to time assign to him. 

 (c) Notwithstanding the foregoing, nothing herein shall prohibit the Executive from
(i) participating in trade associations or industry organizations that are related to the business of the Company, (ii) engaging in charitable, civic or political activities including Executive’s current private school and fraternity
organization involvement, (iii) engaging in personal investment activities for the Executive and his family that do not give rise to any conflicts of interest with the Company or its affiliates, or (iv) with the prior approval of the Chief
Executive Officer, accepting directorships unrelated to the Company that do not give rise to any conflicts of interest with the Company or its affiliates, in each case so long as such interests do not materially interfere, individually or in the
aggregate, with the performance of the Executive’s duties hereunder. Moreover, express approval is granted herein for Executive to hold one (1) director seat in another for profit organization, provided that such directorship does not give
rise to any conflicts of interest with the Company or its affiliates or businesses or materially interfere with the performance of the Executive’s duties hereunder. 

4. Compensation. 
 (a)
Base Salary. The Company shall pay the Executive a base salary at an annual rate of $800,000, less applicable deductions, payable in substantially equal installments in accordance with the Company’s regular payroll practices as in effect
from time to time (the base salary as in effect from time to time, the “Base Salary”) during the Term. The Base Salary may be increased from time to time at the recommendation of the CEO and with Compensation Committee (defined
below) approval. 
 (b) Annual Bonus. For and in respect of each calendar year during the Term, commencing on January 1, 2021,
the Executive shall be eligible to receive a targeted annual cash incentive award equal to 100% of the then-current Base Salary (the “Target Bonus”), but in no event receive an annual cash incentive award in excess of 150% of the
then-current Base Salary (“Maximum Bonus”). Moreover, it is agreed by the parties that, with respect to calendar year 2020, Executive shall be eligible for the full Target Bonus for such year rather than a prorated bonus. The actual
amount of the bonus (each, an “Annual Bonus”), which may be more or less than the Target Bonus although not exceed the Maximum Bonus, shall be determined based on the achievement of performance criteria relating to the Executive
and/or the Company, as determined each year in good faith by the Compensation Committee of the Board (the “Compensation Committee”), following consultation with the Executive. In addition, for any year beginning with 2020,
coincident with the determination by the Compensation Committee of the performance criteria for such year, the Compensation Committee may adjust upward, only in respect of that year, the Target Bonus and/or the Maximum Bonus applicable thereto. The
Annual Bonus, if any, shall be paid to the Executive by no later than March 15 of the year following the year to which it relates; provided, that, except as otherwise provided in Section 6, the Executive remains
actively employed by the Company and has not provided a notice of resignation to the Company or received a notice of termination from the Company, in each case as of the last day of the calendar year to which the bonus relates. 

  
 2 

 (c) Equity Awards. 

(i) Subject to and upon the terms, conditions, and restrictions set forth in the Nonstatutory Stock Option Agreement attached hereto as
Exhibit A, and applicable equity incentive plan (as may be amended from time to time by the Company), on the Start Date Company shall grant to Executive an option (the “Initial Option”) to purchase 60,000 shares of Cumulus Media
Inc.’s Class A Common Stock (the “Initial Option Shares”). The Initial Option Shares may be purchased at a price equal to the closing price of the Cumulus Media, Inc.’s Class A Common Stock on the Start Date. The
Initial Option Shares are intended to be a nonqualified stock option and shall not be treated as an “incentive stock option” within the meaning of that term under Section 422 of the Internal Revenue Code, or any successor provision
thereto. In addition, subject to and upon the terms, conditions, and restrictions set forth in the Restricted Stock Unit Agreement attached hereto as Exhibit B, and applicable equity incentive plan (as may be amended from time to time by the
Company), on the Start Date Company shall grant to Executive 60,000 restricted share units (“Initial RSUs”). 
 (ii) The Executive
also shall be eligible to receive periodic grants of equity-based awards relating to the Company’s common stock during the Term as determined from time to time in the sole discretion of the Board or the Compensation Committee. Any equity-based
awards relating to the Company’s common stock granted to the Executive on or after the date of this Agreement (including, for purposes of clarity and the avoidance of doubt, the Initial Option Shares and Initial RSUs) are referred to herein as
“Equity Awards.” Such Equity Awards shall be subject to the terms and conditions of the applicable equity plans and programs, including, without limitation, the Company’s right to amend or terminate the plans at any time and without
advance notice to the participants. 
 (d) Vacation and Benefits. The Executive shall be entitled to four (4) weeks of paid
vacation for each calendar year during the term (prorated for any partial calendar year), which shall be accrued and used in accordance with the applicable policies of the Company as in effect from time to time. The Executive shall be eligible to
participate in such medical, dental, vision and life insurance, retirement and other employee benefit plans and perquisites as the Company may have or establish from time to time (the “Employee Plans”) on terms and conditions
applicable to other senior executives of the Company generally. The foregoing, however, shall not be construed to require the Company to establish any such plans or to prevent the modification or termination of such plans once established. 

(e) Expenses. The Company shall pay or reimburse the Executive for reasonable and necessary business expenses incurred by the Executive
in connection with his duties on behalf of the Company in accordance with the applicable expense reimbursement policies of the Company as in effect from time to time (“Expense Reimbursement Policies”), following submission by the
Executive of applicable documentation as required by the Expense Reimbursement Policies. 

  
 3 

 5. Termination of Employment. The Term and the Executive’s employment hereunder
shall be terminated upon the first to occur of the following: 
 (a) The Executive’s death or Disability. For purposes of this
Agreement, “Disability” means that the Executive shall have been substantially unable to perform his material duties hereunder by reason of physical or mental illness or incapacity for a period of four and one-half (4.5) consecutive months, or for a period of 135 calendar days, whether or not consecutive, during any 365-day period, as a result of a condition that is treated as a
total or permanent disability under the long-term disability insurance policy of the Company that covers the Executive, as in effect from time to time. The determination of “Disability” shall be made by a physician selected by the Company
in good faith and subject to the approval of the Executive (or his family if Executive is not capable of approval) which approval shall not be unreasonably withheld, and the Executive hereby consents to examination by such physician and to the
disclosure to the Company by any physician of any and all diagnoses, test results, opinions and other information obtained by such physician during or as a result of the examinations to which the Executive hereby consents. 

(b) The termination of the Executive’s employment by the Company with or without Cause. For purposes of this Agreement,
“Cause” means (i) the conviction of the Executive of a felony under the laws of the United States or any state thereof, whether or not appeal is taken; (ii) the conviction of the Executive for a violation of criminal law
involving the Company and its business; (iii) the willful misconduct of the Executive, or the willful or continued failure by the Executive (except as a result of disability or illness) to substantially perform his duties hereunder, in either
case which has a material adverse effect on the Company; or (iv) the willful fraud or material dishonesty of the Executive in connection with his performance of duties to the Company. 

(c) The termination of the Executive’s employment by the Executive with or without Good Reason. For purposes of this Agreement,
“Good Reason” means, in each case without the Executive’s express written consent, (i) a material diminution in the Executive’s authority, duties or responsibilities or an adverse change in the Executive’s
reporting responsibilities; (ii) a material diminution in the Executive’s title or position; (iii) a reduction in the Base Salary; (iv) with respect to the annual cash incentive award, a reduction in the Target Bonus or Maximum
Bonus, (v) the relocation of the Executive’s principal place of employment to a location more than thirty (30) miles from the city of New York, New York; (vi) a failure by any successor to the Company to expressly assume this
Agreement; or (vii) a material breach of this Agreement by the Company. Notwithstanding the foregoing, no termination of employment by the Executive shall be a termination for Good Reason unless (A) within thirty (30) days after the
date of the condition or event giving rise to Good Reason, the Executive gives notice to the Company that the Executive does not wish to remain in the employ of the Company as a result of such condition or event, (B) the Company does not cure
such condition or event within thirty (30) days after receiving the notice described in the preceding clause (A), and (C) the Executive terminates employment within ninety (90) days after the initial existence of such condition or
event. 
 (d) The termination of the Executive’s employment following the timely provision of a
Non-Renewal Notice by the Company or the Executive to the other party. 

  
 4 

 6. Payments and Benefits Upon Termination of Employment. 

(a) Termination upon the Executive’s Death or Disability. If, during the Term, the Executive dies or incurs a Disability, the Term
and the Executive’s employment hereunder shall automatically terminate, and the Company shall have no further obligation to the Executive hereunder, except to pay to or provide the Executive (or his estate) with (i) any unpaid Base Salary
through the date of termination; (ii) any accrued and unpaid bonus payable with respect to a completed calendar year pursuant to Section 4(b); (iii) any accrued and unpaid vacation and/or sick days accrued through the
date of termination; (iv) any amounts or benefits owing to the Executive or his beneficiaries under the Employee Plans and Equity Awards (pursuant to the terms and conditions thereof); and (v) any amounts owing to the Executive for
reimbursement of expenses properly incurred by the Executive prior to the date of termination pursuant to the Expense Reimbursement Policies, in each case payable in accordance with the Company’s payroll procedures, the terms of the applicable
plans, or the Expense Reimbursement Policies, as applicable (the “Accrued Compensation and Benefits”). In addition, the Executive (or his estate) shall be entitled to receive an Annual Bonus equal to the product of (A) the
Annual Bonus the Executive would have received had he remained employed through the last day of the calendar year to which the bonus relates, based on actual performance through the applicable performance period, and (B) a fraction, the
numerator of which is the number of days the Executive was employed by the Company in the year in which the date of date of termination occurred and the denominator of which is 365, payable at the time bonus payments are made to other executives of
the Company but in no event later than March 15 of the calendar year following the year that includes the Executive’s date of termination. 

(b) Termination by the Company for Cause or Resignation by the Executive without Good Reason. If, during the Term, the Executive’s
employment is terminated by the Company for Cause or the Executive resigns without Good Reason, the Company shall have no further obligation to the Executive hereunder, except to pay or provide the Accrued Compensation and Benefits. 

(c) Termination by the Company without Cause or Resignation by the Executive for Good Reason. If, during the Term, the Executive’s
employment is terminated by the Company without Cause (other than a termination pursuant to Section 6(a)) or the Executive terminates his employment for Good Reason (in either case, a “Qualifying
Termination”), then the Company shall pay or provide the Accrued Compensation and Benefits, and subject to Section 6(f): 

(i) The Company shall make cash payments to the Executive equal in the aggregate to the product of (A) one and one-half (1.5) (the “Severance Multiple”) and (B) the sum of the Base Salary and Target Bonus as in effect immediately prior to the date of termination (without regard to any reduction to the
Base Salary or Target Bonus that gave rise to Good Reason), payable in four (4) substantially equal installments, commencing on the 90th day following the date of termination (the
“Initial Payment Date”) and continuing on the next three (3) following three (3) month anniversaries of the Initial Payment Date (the “Severance Payments”); 

  
 5 

 (ii) The Company shall make a lump sum cash payment to the Executive equal to the product
of (A) the Annual Bonus the Executive would have received had he remained employed through the last day of the calendar year to which the bonus relates, based on actual performance through the applicable performance period, and (B) a
fraction, the numerator of which is the number of days the Executive was employed by the Company in the year in which the date of termination occurred and the denominator of which is 365, payable at the time bonus payments are made to other
executives of the Company but in no event later than March 15 of the calendar year following the year that includes the Executive’s date of termination (the “Pro-Rata Bonus”); and

 (iii) The Executive and his covered dependents shall be entitled to continued participation for twelve (12) months following the
date of termination (the “Benefit Continuation Period”) in such medical, dental, vision and hospitalization insurance coverage in which the Executive and his eligible dependents were participating immediately prior to the date of
termination, subject to the terms and conditions of the applicable benefit plans as in effect from time to time (the “Continued Benefits”), provided that the Executive shall not be required to pay any premiums or other amounts to
obtain such coverage. The full amount of the premiums that the Executive would be required to pay to obtain the Continued Benefits actually provided to the Executive during the Benefit Continuation Period under the Consolidated Omnibus Budget
Reconciliation Act of 1986, as amended (the “Premium Cost”), shall be imputed as taxable income to the Executive, and the Executive shall be responsible for the payment of all income taxes incurred as a result of such imputed
income, provided that the Company will reimburse the Executive (within thirty (30) days following the Company’s receipt of evidence of the cost to Executive) for the amount of such income taxes plus the amount of all additional income
taxes incurred by the Executive upon such payment by the Company. If the Executive is not permitted to receive a Continued Benefit during the Benefit Continuation Period as a result of applicable law or the terms of the applicable Employee Plan, the
Company shall reimburse the Executive (within thirty (30) days following the Company’s receipt of evidence of the cost to Executive) for (i) the amount actually incurred by the Executive to obtain coverage no more favorable than the
applicable Continued Benefit, up to the portion of the Premium Cost necessary to provide the corresponding Continued Benefit for the applicable portion of the Continued Benefit Period, plus (ii) the amount of all additional income taxes
incurred by the Executive upon such payment by the Company (the “Benefit Reimbursement”). Notwithstanding the foregoing, the Executive shall not be entitled to receive a Continued Benefit or the Benefit Reimbursement to the
extent that he becomes eligible to receive a comparable benefit from another employer of hers during the Benefit Continuation Period. The Executive shall promptly, and in no event later than five (5) business days after the commencement of
eligibility thereof during the Benefit Continuation Period, report the eligibility to receive any such comparable benefit to the Company. 

(d) Qualifying Termination in Connection with a Change in Control. If, during the Term, the Executive’s employment is terminated by
reason of a Qualifying Termination within twelve (12) months following a Change in Control or within three (3) months prior to a Change in Control (except as otherwise provided in Section 6(c)(iii) above in the case of the benefits
provided by Section 6(d)(iii) below), then the Company shall pay or provide the Accrued Compensation and Benefits, and subject to Section 6(f) and in lieu of the payments and benefits set forth in
Section 6(c): 
 (i) The Company shall make the Severance Payments to the Executive; provided that for
purposes of this Section 6(d)(i), the Severance Multiple shall be two (2) if such termination occurs during the Term; 

  
 6 

 (ii) The Company shall pay the Pro-Rata Bonus to
the Executive; 
 (iii) 100% of the Equity Awards shall become immediately and fully vested and exercisable, with any performance conditions
or restrictions on exercise deemed satisfied; and 
 (iv) The Company shall provide the Continued Benefits (or payment in lieu thereof) as
set forth in Section 6(c)(iv) for a Benefit Consideration Period of eighteen (18) months. 
 For purposes of this Agreement,
“Change in Control” means the date that: (i) any one person, or more than one person acting as a group, acquires ownership of stock of the Company that, together with stock of the Company held by such person or group,
constitutes more than fifty percent (50%) of the total fair market value or total voting power of the stock of the Company; provided, if any one person, or more than one person acting as a group, is considered to own more than fifty percent
(50%) of the total fair market value or total voting power of the stock of the Company, the acquisition of additional stock by the same person or persons is not considered to cause a “change in control”; (ii) any one person, or more than
one person acting as a group, acquires (or has acquired during the twelve (12) month period ending on the date of the most recent acquisition by such person or persons) ownership of the Company’s stock possessing thirty percent (30%) or
more of the total voting power of the stock of the Company; (iii) a majority of members of the Board is replaced during any twelve (12) month period by directors whose appointment or election is not endorsed by a majority of the members of
the Board before the date of the appointment or election; provided, however, that for purposes of the above any member becoming a director subsequent to the date hereof whose initial assumption of office occurs as a result of an actual or threatened
election contest with respect to the election or removal of directors or other actual or threatened solicitation of persons or consents by or on behalf of any person other than the Board shall not be considered a member whose appointment or election
has been endorsed by a majority of members of the Board; (iv) a consummation of a merger or consolidation involving the Company or in which Company securities are issued, unless (x) the persons who held Company voting securities
immediately prior to consummation of such transaction continue to hold at least 50% of the voting power of the stock of the surviving entity in such transaction immediately following consummation of such transaction (or its ultimate parent company
if the surviving entity is a subsidiary), (y) no person owns over thirty percent (30%) of the surviving entity (or its ultimate parent entity if the surviving entity is a subsidiary), and (z) the Company’s directors immediately prior to
consummation of the merger or consolidation constitute a majority of the board of directors of the surviving entity (or its ultimate parent entity if the surviving entity is a subsidiary) following such merger or consolidation; or (v) any one
person, or more than one person acting as a group, acquires (or has acquired during the 12-month period ending on the date of the most recent acquisition by such person or persons) assets from the Company that
have a total gross fair market value equal to or more than forty percent (40%) of the total gross fair market value of all of the assets of the Company immediately before such acquisition or acquisitions (for this purpose, gross fair market

  
 7 

 
value means the value of the assets of the Company, or the value of the assets being disposed of, determined without regard to any liabilities associated with such assets); provided,
however, a transfer of assets by the Company is not treated as a “change in control” if the assets are transferred to (a) a shareholder of the Company (immediately before the asset transfer) in exchange for or with respect to
his/her/its stock, (b) an entity, fifty percent (50%) or more of the total value or voting power of which is owned, directly or indirectly, by the Company, (c) a person, or more than one person acting as a group, that owns, directly or
indirectly, fifty percent (50%) or more of the total value or voting power of all the outstanding stock of the Company, or (d) an entity, at least fifty percent (50%) of the total value or voting power of which is owed, directly or indirectly,
by a person described in clause (c) hereof. 
 (e) Termination by the Company or the Executive following Delivery of Non-Renewal Notice. If, during the Term, the Company or the Executive timely delivers to the other a Non-Renewal Notice as set forth in
Section 2, the Executive’s employment shall terminate, effective as of the last scheduled day of the Initial Term or then-current Renewal Term, as applicable. Such termination if effected by the issuance of a Non-Renewal Notice by the Company shall be treated as a termination by the Company without Cause and the Executive shall be entitled to the payments and benefits set forth in Section 6(c)
or Section 6(d), as applicable. If such termination is effected by a Non-Renewal Notice issued by the Executive, the Company shall have no further obligation to the Executive
hereunder, except to pay or provide the Accrued Compensation and Benefits. 
 (f) Release. Notwithstanding anything herein to the
contrary, the Company shall not be obligated to make or continue any payment or provide any benefit under Section 6(a), 6(c) or 6(d) (other than the Accrued Compensation and Benefits) unless (i) by the
22nd calendar day after the date of termination of employment (or by such later date specified by the Company in writing as required to comply with applicable law), the Executive executes a release in the form attached hereto as Exhibit C
(the “Release”) and (ii) the Executive does not revoke the Release during any applicable revocation period. 
 (g)
No Offset. In the event of termination of the Executive’s employment, the Executive shall be under no obligation to seek other employment and, except as otherwise set forth in Section 6(c)(iv) or
6(d)(iv), there shall be no offset against amounts due to him on account of any remuneration or benefits provided by any subsequent employment he may obtain. 

(h) Forfeiture. Notwithstanding the foregoing, any right of the Executive to receive termination payments and benefits hereunder (other
than the Accrued Compensation and Benefits) shall be forfeited if the Executive materially breaches Section 7 or 8; provided that, before invoking this Section 6(h), the Company shall
provide the Executive with ten (10) days to cure such breach, to the extent curable. 
 (i) Resignation from Certain Positions.
Upon the termination of the Executive’s employment for any reason, if and to the extent requested by the Board, the Executive shall resign from the Board (if applicable), all fiduciary positions (including, without limitation, as trustee) and
from all other offices and positions, including without limitation, board membership of any subsidiaries or affiliates, he holds with the Company and any of its subsidiaries or affiliates; provided, however, that if the Executive fails
or refuses to tender such resignations after the Board has made such request, then the Board shall be empowered to tender the Executive’s resignation or remove the Executive from such offices and positions. 

  
 8 

 7. Restrictive Covenants. 

(a) Acknowledgements. The Executive acknowledges that, as an executive and key employee of the Company: 

(i) the Executive has participated or will participate in the development of the Company’s business strategies; 

(ii) by virtue of his position of trust with the Company, the Executive has had or will have access to extensive Confidential Information (as
defined in Section 7(b)) related to the Company’s business, to which the Company has devoted and will continue to devote substantial time, money and effort to develop and maintain the proprietary and confidential
nature thereof; 
 (iii) the Executive shall be responsible for managing, directing, and supervising other personnel of the Company
performing a variety of services related to the Company’s business and coordinating their activities, shall develop close working relationships with such personnel and the Company shall expend substantial time, effort, and financial resources
to train and develop its personnel; and 
 (iv) in the performance of his duties to the Company, the Executive has been or will be brought
into contact, either in person, by telephone, by e-mail, and otherwise, with existing and potential clients or information related to those existing and potential clients, or has had or will have
responsibility for personnel who have such contact and knowledge of such personnel’s activities. 
 For purposes of this
Section 7, the term “the Company” shall mean and include Cumulus Media Inc. and all entities of which such company owns, directly or indirectly through another company, 50% or more of the issued and outstanding
capital stock or other equity interests of any class or classes having, by the terms thereof or by contract with one or more other equity holders, ordinary voting power to elect the directors (or other management personnel) of such entity. 

(b) Confidential Information. For purposes of this Agreement, the term “Confidential Information” shall mean and
include any and all knowledge, information, or data, whether written or oral and, if written, howsoever produced or reproduced and whether or not denoted or marked confidential, that is the proprietary information of the Company, any of its
subsidiaries, or any of its other affiliates (whether or not a trade secret), including the following: 
 (i) all research, designs,
developments, know-how, computer programs, algorithms, models, software or programming, summaries, reports, drawings, charts, specifications, descriptions, routines, processes, inventions, discoveries,
methods, improvements, adaptations, and similar proprietary concepts and ideas and related documentation; 

  
 9 

 (ii) the terms of any agreement or contract between the Company and any client, customer,
supplier, or personnel; 
 (iii) any information concerning or belonging to the Company’s clients, customers, and vendors (including
client, customer, and vendor lists and databases), or the existing and contemplated projects or programs of the Company and its clients and vendors; 

(iv) any methods of operation, programming plans, marketing plans, techniques, manuals, technical plans, strategic plans, distribution plans,
production plans, financial information, budgets, salary information, sources of supply and materials and costs, discount and pricing practices, contractual arrangements and negotiations of the Company; and 

(v) any other information of similar or dissimilar nature that the Company designates as Confidential Information and/or that is proprietary
to or within the unique knowledge of the Company; and that has been or will be used or developed by the Company prior to or at any time during the period of the Executive’s employment by the Company that has been or is disclosed to or learned
by the Executive during the Executive’s employment. Notwithstanding the foregoing, Confidential Information shall not include information: 

(1) that was in the public domain at the time it was disclosed or subsequently becomes in the public domain other than as a result of a
disclosure by the Executive in violation of this Agreement; 
 (2) that the Executive can demonstrate by written proof was received by the
Executive after the time of disclosure by the Company or after the time of discovery by the Executive during the Executive’s employment from a third party who, to the knowledge of the Executive, did not acquire it in violation of a
confidentiality agreement with the Company or its employees or agents, or from a third party who was not otherwise prohibited from transmitting the information to the Executive by a contractual, legal, or fiduciary obligation of confidence to the
Company; or 
 (3) that is disclosed by the Executive with the prior written consent of an executive officer of the Company or the Board.

 (c) Duty Not to Disclose. The Executive agrees that the Company has a legitimate interest in protecting the Confidential
Information and that the preservation and protection of the Confidential Information are essential duties of the Executive’s employment. The Executive therefore agrees that, during the term of his employment with the Company and for so long
thereafter as the Confidential Information remains confidential, the Executive shall: 
 (i) not use any Confidential Information on his own
behalf or on behalf or any unauthorized person, or disclose or reveal any Confidential Information, or any portion thereof, to any unauthorized person, except to carry out the Executive’s authorized duties as an employee of the Company; 

  
 10 

 (ii) not make, or permit or cause to be made, copies of the Confidential Information except
to carry out the Executive’s authorized duties as an employee of the Company; 
 (iii) not place on, download to, or store in any non-Company-owned electronic device (including any electronic communications device) any Confidential Information; and 

(iv) take all reasonable precautions to prevent the inadvertent disclosure by the Executive of the Confidential Information in his possession
to any unauthorized person. 
 Nothing in this Agreement shall prohibit the Executive from reporting possible violations of federal law or regulation to any
governmental agency or entity, including but not limited to the Department of Justice, the Securities and Exchange Commission, the Congress, and any agency Inspector General, or making other disclosures that are protected under the whistleblower
provisions of federal law or regulation. The Executive does not need the prior authorization of the Company or the Board to make any such reports or disclosures and the Executive is not required to notify the Company that he has made such reports or
disclosures. The Executive may also disclose Confidential Information if reasonably necessary pursuant to any litigation or arbitration between the Executive and the Company or any of its affiliates. 

(d) Legal Orders to Disclose. Upon receipt of a subpoena or other compulsory process that could possibly require disclosure of any
Confidential Information by the Executive, to the extent legally permitted, the Executive shall provide a copy of the compulsory process and complete information regarding the date and circumstances under which he received it to the Company within
twenty-four (24) hours of such receipt. The Executive shall not make any disclosure until the latest possible date for making such disclosure in accordance with such process. If the Company seeks to prevent disclosure in accordance with the
applicable legal procedures and provides the Executive with notice before the latest possible date that it has initiated such procedures, the Executive shall not make disclosure of any Confidential Information that is the subject of such procedures
until such objections are withdrawn or ruled upon or, if earlier, he would be in contempt of court. 
 (e) Duration. The covenants
made in Sections 7(c) and (d) shall remain in effect while the Executive is employed by the Company and for so long thereafter as the information in question remains confidential. Nothing in such subsections is intended to exclude
the application of any laws protecting Confidential Information consisting of trade secrets, including the Georgia Trade Secrets Act of 1990, as amended. 

(f) Return. In the event the Executive’s employment with the Company terminates for any reason, the Executive shall promptly return
to the Company all property of the Company in the Executive’s possession or under the Executive’s direct or indirect control, including all Confidential Information and all equipment, notebooks, and materials, reports, notes, contracts,
memoranda, documents, and data of the Company constituting or relating to the Confidential Information (and any and all copies thereof), whether typed, printed, written, or on any source of computer media, unless the parties agree otherwise.
Notwithstanding the foregoing, the Executive may retain his address book to the extent it only contains contact information and his calendar and personal correspondence. 

  
 11 

 (g) Ownership. The Executive agrees and acknowledges that the Confidential
Information, as between the Company and the Executive, shall be deemed and at all times remain and constitute the exclusive property of the Company, whether or not patentable or copyrightable, and that the Company has reserved—and does hereby
reserve—all rights in and to the same for all purposes. 
 (h) Proprietary Information of Others; Third-Party Agreements. The
Executive represents that his performance of all the terms hereof and as an employee of the Company does not and will not breach any agreement to keep in confidence proprietary information acquired by the Executive in confidence or in trust prior to
the Executive’s engagement by the Company. 
 (i) Covenant Not to Compete. The Executive covenants that, while the Executive is
employed by the Company and for a period of six (6) months from the date of termination of the Executive’s employment for any reason, the Executive shall not directly or by assisting others do any of the following: 

(i) engage as a consultant, advisor, or manager—capacities in which the Executive will have acted for the Company—whether as an
employee, independent contractor, proprietor, or otherwise, in any business that serves as a commercial media outlet selling advertising (regardless of medium), which is the business of the Company (the “Business”), and serves any
of the listening areas (as defined by the Arbitron Metro Survey Area) served by the Company on the date of the termination of the Executive’s employment or such additional listening areas as the Executive knows as of such date the Company has
definite and immediate plans to conduct the Business (a “Competing Business”); Competing Business shall include radio stations; television stations; cable operators; podcast businesses; newspapers; magazines; Internet
advertising; publications and broadcast businesses; music-on-demand services (such as Spotify and Pandora); outdoor advertising and billboards and advertising agencies;

 (ii) for the purpose of furthering or assisting a Competing Business, solicit or attempt to solicit any client, customer, or account of
the Company (A) that, during the twelve (12) month period prior to the date of such termination of employment, has obtained or contracted to obtain services from the Company and with which the Executive or Company personnel or
representatives for whom or which the Executive had responsibility had contact during the term of the Executive’s employment by the Company; (B) that the Executive knows were prospective clients, customers, or accounts that the Company was
actively seeking on the date of termination of the Executive’s employment (whether or not such individual or entity has yet become an actual client or customer); (C) about which the Executive obtained Confidential Information in the ordinary
course of business as a result of the Executive’s association with the Company; or (D) that received products or services authorized by the Company, the sale or provision of which resulted in commissions, earnings, or other compensation
for the Executive; or 

  
 12 

 (iii) for himself or for or on behalf of any business, entity or individual, divert,
solicit or hire away, or attempt to divert, solicit or hire away, any individual who, on the date of such termination or at any time during the twelve (12) month period immediately preceding such date, was employed, retained, or engaged by the
Company as an employee of, or provider of services to, the Company and with whom the Executive had contact during performance of the Executive’s job duties to the Company to leave such employ or service with the Company for any employment or
similar services opportunity with any other business; regardless of whether such individual is or was a full-time employee, part-time employee, temporary worker, or independent contractor of the Company; employed, retained, or engaged pursuant to a
written agreement; or employed, retained, or engaged for a determined period or at-will. 
 (j)
Independent Covenants. It is understood and intended by the parties hereto that each restrictive covenant set forth in Section 7(c) and in clauses (i) through (iii) of Section 7(i) be
construed as an agreement independent of any other provision in this Agreement. The existence of any claim or cause of action of the Executive against the Company, whether predicated on this Agreement or otherwise, shall not constitute a defense to
the enforcement by the Company of such covenants. The Executive agrees that such covenants are appropriate and reasonable when considered in light of the nature and extent of the Business and the scope of responsibilities of the Executive. 

(k) Injunctive Relief. The Executive acknowledges and agrees that any breach or threatened breach by his of any of the provisions of
this Agreement will cause irreparable harm and continuing damages to the Company and that the remedies at law for any such breach or threatened breach will be inadequate. Accordingly, in addition to any other remedies that may be available to the
Company at law or in equity in such event, the Company shall be entitled to seek and obtain, from any court of competent jurisdiction, a decree of specific performance and/or a temporary and permanent injunction, without posting of any bond or other
security and without proving special damages or irreparable injury, enjoining and restricting the breach or threatened breach. 
 8.
Continued Availability and Cooperation. 
 (a) Following termination of the Executive’s employment for any reason, the Executive
shall reasonably cooperate with the Company and with the Company’s counsel in connection with any present and future actual or threatened litigation, administrative proceeding or investigation involving the Company or its subsidiaries or
affiliates that relates to events, occurrences or conduct occurring (or claimed to have occurred) during the period of the Executive’s employment by the Company, and with respect to which the Executive has pertinent information. The
Executive’s cooperation shall include, without limitation: 
 (i) Making himself reasonably available for interviews and discussions
with the Company’s counsel, as well as for depositions and trial testimony; 
 (ii) If depositions or trial testimony are to occur,
making himself reasonably available and cooperating in the preparation therefor, as and to the extent that the Company or the Company’s counsel reasonably requests; 

  
 13 

 (iii) Refraining from impeding in any way the Company’s prosecution or defense of such
litigation or administrative proceeding; and 
 (iv) Reasonably cooperating fully in the development and presentation of the Company’s
prosecution or defense of such litigation or administrative proceeding. 
 (b) Any such cooperation shall be on reasonable notice and take
into account the Executive’s professional and personal commitments. The Company shall reimburse the Executive for reasonable travel, lodging, telephone and similar expenses, as well as reasonable attorneys’ fees (if the Executive and the
Company determine in good faith that separate counsel is needed) incurred in connection with any such cooperation. 
 9. Code
Section 280G. 
 (a) If it shall be determined that any benefit provided to the Executive or payment or distribution
by or for the account of the Company or its affiliates to or for the benefit of the Executive, whether provided, paid or payable or distributed or distributable pursuant to the terms of this Agreement or otherwise (a “Payment”)
would be subject to the excise tax imposed by Section 4999 of the Internal Revenue Code of 1986, as amended (the “Code”), or any interest or penalties are incurred by the Executive with respect to such excise tax resulting from
any action or inaction by the Company or its affiliates (such excise tax, together with any such interest and penalties, collectively, the “Excise Tax”), then the amounts payable under this Agreement shall be reduced so that the
Parachute Value of all Payments, in the aggregate, equals the Safe Harbor Amount; provided that such reduction shall only be made if such reduction results in a more favorable after-tax position for the
Executive. The payment reduction contemplated by the preceding sentence, if any, shall be implemented by determining the Parachute Payment Ratio for each “parachute payment” and then reducing the parachute payments in order beginning with
the parachute payment with the highest Parachute Payment Ratio. For parachute payments with the same Parachute Payment Ratio, such parachute payments shall be reduced based on the time of payment of such parachute payments, with amounts having later
payment dates being reduced first. For parachute payments with the same Parachute Payment Ratio and the same time of payment, such parachute payments shall be reduced on a pro rata basis (but not below zero) prior to reducing parachute payments with
a lower Parachute Payment Ratio. 
 (b) All determinations required to be made under this Section 9, shall be made
by the Company’s independent, certified public accounting firm or such other certified public accounting firm as may be designated by the Company prior to the change in ownership or effective control (as defined for purposes of
Section 280G of the Code) of the Company (a “280G Change in Control”) (the “Accounting Firm”) which shall provide detailed supporting calculations both to the Company and the Executive within fifteen
(15) business days of the receipt of notice from the Executive that there has been a Payment, or such earlier time as is requested by the Company. If the Accounting Firm is serving as accountant or auditor for the individual, entity or group
effecting a 280G Change in Control, the Executive shall appoint another nationally recognized accounting firm which is reasonably acceptable to the Company to make the determinations required hereunder (which accounting firm shall then be referred
to as the Accounting Firm hereunder). All fees and expenses of the Accounting Firm shall be borne solely by the Company. Any determination by the Accounting Firm shall be binding upon the Company and the Executive. 

  
 14 

 (c) The following terms shall have the following meanings for purposes of this
Section 9: 
 (i) “Base Amount” means “base amount,” within the meaning of
Section 280G(b)(3) of the Code. 
 (ii) “Parachute Payment Ratio” shall mean a fraction, the numerator of which is the
value of the applicable parachute payment for purposes of Section 280G of the Code and the denominator of which is the intrinsic value of such parachute payment. 

(iii) “Parachute Value” of a Payment shall mean the portion of such Payment that constitutes a “parachute payment”
under Section 280G(b)(2), as determined by the Accounting Firm for purposes of determining whether and to what extent the Excise Tax will apply to such Payment. 

(iv) “Safe Harbor Amount” means three (3) times the Base Amount, less one dollar ($1). 

10. Entire Agreement. This Agreement, and any schedules or exhibits hereto, embody the entire agreement between the parties relating to
the subject matter hereof and supersede any and all other discussions, understandings, and agreements, either oral or in writing, between the parties relating to the subject matter of this Agreement (including, but not limited to, the Existing
Agreement). 
 11. Withholding of Taxes. The Company shall withhold from any amounts payable under this Agreement all federal, state,
local or other taxes as the Company is required to withhold pursuant to any law or government regulation or ruling. 
 12. Successors and
Binding Agreement. 
 (a) The Company shall require any successor (whether direct or indirect, by purchase, merger, consolidation,
reorganization or otherwise) to all or substantially all of the business or assets of the Company expressly to assume and agree to perform this Agreement in the same manner and to the same extent the Company would be required to perform if no such
succession had taken place. This Agreement shall be binding upon and inure to the benefit of the Company and any successor to the Company, including, without limitation, any individual or entity acquiring, directly or indirectly, all or
substantially all of the business or assets of the Company, whether by purchase, merger, consolidation, reorganization or otherwise (and such successor shall thereafter be deemed “the Company” for purposes of this Agreement), but this
Agreement shall not otherwise be assignable or delegable by the Company, except that the Company may assign its rights and delegate its duties hereunder to any individual or entity who acquires all of the voting stock of the Company (or to any
parent entity thereof) so long as so doing does not materially and adversely affect the Executive’s rights hereunder. 

  
 15 

 (b) This Agreement shall inure to the benefit of and be enforceable by the Executive’s
personal or legal representatives, executors, administrators, successors, heirs, distributees and legatees. 
 (c) This Agreement is personal
in nature and the Company and the Executive may not, without the written consent of the other party, assign or delegate this Agreement or any rights or obligations hereunder except as expressly provided in Sections 12(a) and (b).
Without limiting the generality or effect of the foregoing, the Executive’s right to receive payments hereunder shall not be assignable, transferable or delegable, whether by pledge, creation of a security interest, or otherwise, other than by
a transfer by the Executive’s will or by the laws of descent and distribution and, in the event of any attempted assignment or transfer contrary to this Section 12(c), the Company shall have no liability to pay any
amount so attempted to be assigned, transferred or delegated. 
 13. Governing Law. This Agreement shall be governed by and construed
and interpreted in accordance with the internal, substantive laws of the State of New York, without regard to that State’s principles governing conflicts of laws. 

14. Validity/Severability. The Company and the Executive agree that (i) the provisions of this Agreement shall be severable in the
event that, for any reason whatsoever, any of the provisions hereof are invalid, void or otherwise unenforceable, (ii) any such invalid, void or otherwise unenforceable provisions shall be replaced by other provisions which are as similar as
possible in terms to such invalid, void or otherwise unenforceable provisions but are valid and enforceable, and (iii) the remaining provisions shall remain valid and enforceable to the fullest extent permitted by applicable law. 

15. Survival. In addition to all provisions of this Agreement that by their terms are to survive, all accrued obligations and the
provisions of Section 7 shall survive the expiration or termination of this Agreement for any reason. 
 16.
Section 409A of the Code. For purposes of this Agreement, “Section 409A” means Section 409A of the Code and the Treasury Regulations promulgated thereunder (and such other Treasury
or Internal Revenue Service guidance) as in effect from time to time. The parties intend that any amounts payable hereunder will be either exempt from Section 409A, or if such payments could constitute “deferred compensation” within
the meaning of Section 409A, compliant with Section 409A. Notwithstanding the foregoing, the Executive acknowledges and agrees that he shall be solely responsible for, any taxes or penalties that may be imposed on the Executive under
Section 409A with respect to the Executive’s receipt of payments hereunder; provided, that nothing in this Section 16 shall be construed as a waiver by the Executive of any claims he may have against the Company related to any
operational failures by the Company which are finally determined to be the cause of any such taxes or penalties under Section 409A. This Agreement shall be administered and interpreted in a manner consistent with this intent. Consistent with
that intent, and to the extent required under Section 409A, for benefits that are to be paid in connection with a termination of employment, “termination of employment” shall be limited to such a termination that constitutes a
“separation from service” under Section 409A. Notwithstanding any provision of this Agreement to the contrary, if the Executive is a “specified employee,” determined pursuant to procedures adopted by the Company in
compliance with 

  
 16 

 
Section 409A, on the date of his separation from service (within the meaning of Treasury Regulation section 1.409A-1(h)) and if any portion of the
payments or benefits to be received by the Executive upon his termination of employment would constitute a “deferral of compensation” subject to Section 409A, then to the extent necessary to comply with Section 409A, amounts that
would otherwise be payable pursuant to this Agreement during the six-month period immediately following the Executive’s termination of employment shall instead be paid or made available on the earlier of
(i) the first business day of the seventh month after the date of the Executive’s termination of employment, or (ii) the Executive’s death. For purposes of application of Section 409A, to the extent applicable, each payment
made under this Agreement shall be treated as a separate payment. Notwithstanding any provision of this Agreement to the contrary, to the extent any reimbursement or in-kind benefit provided under this
Agreement is nonqualified deferred compensation within the meaning of Section 409A: (i) the amount of expenses eligible for reimbursement, or in-kind benefits provided, during a calendar year may not
affect the expenses eligible for reimbursement, or in-kind benefits to be provided, in any other taxable year; (ii) the reimbursement of an eligible expense must be made on or before the last day of the
calendar year following the calendar year in which the expense was incurred; and (iii) the right to reimbursement or in-kind benefits is not subject to liquidation or exchange for another benefit. 

17. Amendment; Waiver. 

(a) This Agreement may only be amended and supplemented in a writing signed by the Executive and an executive officer of the Company expressly
providing for such modification. 
 (b) The waiver by either party of a breach of any provision of this Agreement by the other shall not
operate or be construed as a waiver of any subsequent breach by the other, and any such waiver must be in a writing signed by an officer of the waiving party. 

18. Notice. Any notice, request, consent and other communication required or permitted hereunder shall be in writing and shall be deemed
to have been duly given (i) when received if personally delivered, (ii) within one (1) day after being sent by recognized overnight delivery service, or (iii) within five (5) days after being sent by registered or certified
mail, return receipt requested, postage prepaid, to the parties (and to the persons to whom copies shall be sent) at their respective addresses set forth below. 

If to the Company: 
 Cumulus Media
Inc. 
 3280 Peachtree Road, N.W., Suite 2200 

Atlanta, Georgia 30305 
 c/o:
General Counsel 
 If to the Executive: 

At the address contained in the Executive’s payroll records 

  
 17 

 Either party may change the address or the persons to whom notice shall be directed by notifying the other
parties as provided in this Section 18. 
 19. Counterparts. This Agreement may be executed in two
(2) counterparts and by the parties in separate counterparts, each of which when so executed and delivered shall be deemed to be an original and both of which counterparts, taken together, shall constitute one and the same instrument. Delivery
by one or both parties of an executed counterpart of this Agreement via facsimile, telecopy, or other electronic method of transmission pursuant to which the signature of such party can be seen (including Adobe Corporation’s Portable Document
Format) shall have the same force and effect as the delivery of an original executed counterpart of this Agreement. Notwithstanding the foregoing, a party who delivers an executed counterpart via such electronic means shall nonetheless be obligated
to subsequently provide an original signed copy of such document, on paper, to the other party at any time upon request. 
 20.
Headings. The descriptive headings herein are inserted for convenience of reference only and are not intended to be a substantive part of or to affect the meaning or interpretation of this Agreement. Reference to any agreement, document or
instrument means such agreement, document or instrument as amended or otherwise modified from time to time in accordance with the terms thereof, and if applicable, hereof. In the event an ambiguity or question of intent or interpretation arises,
this Agreement shall be construed as if drafted jointly by the parties, and no presumption or burden of proof will arise favoring or disfavoring either party by virtue of the authorship of any of the provisions of this Agreement. 

21. Construction. The section headings and titles contained herein are each for reference only and shall not be deemed to affect the
meaning or interpretation of this Agreement. The words “hereby,” “herein,” “hereinabove,” “hereinafter,” “hereof” and “hereunder,” when used anywhere in this Agreement, refer to this
Agreement as a whole and not merely to a subdivision in which such words appear, unless the context otherwise requires. The singular shall include the plural, the conjunctive shall include the disjunctive, and the masculine gender shall include the
feminine and neuter, and vice versa, unless the context otherwise requires. Each use of the word “include,” “includes,” or “including” shall be deemed in each case to be followed by the words “but not limited
to.” This Agreement shall not be construed strictly for or against either party because that party, or its attorney, prepared this Agreement or any provision hereof. 

22. Compliance with Dodd-Frank. All payments under this Agreement, if and to the extent subject to the Dodd-Frank Wall Street Reform and
Consumer Protection Act (as amended from time to time, the “Dodd-Frank Act”), shall be subject to any incentive compensation policy established from time to time by the Company to comply with the Dodd-Frank Act, but only to the
extent that the provisions of any policy so established are required by the Dodd-Frank Act. 
 23. Arbitration. The sole and exclusive
method for resolving all disputes under, arising out of, related to, or in connection with this Agreement shall be binding arbitration in New York, New York, in a proceeding administered by the New York, New York Office of the American Arbitration
Association (“AAA”) in accordance with the Commercial Dispute Resolution and Procedures of the Arbitration Rules of the AAA (the “Rules”). The arbitration shall be conducted by a single arbitrator jointly appointed
by the parties; provided, however, that 

  
 18 

 
if the parties fail after good faith negotiation to agree on the arbitrator within thirty (30) days after one party’s call for arbitration, the arbitrator shall be appointed by the AAA
in accordance with the Rules. Disputes about arbitration procedure shall be resolved by the arbitrator. The arbitrator may proceed to an award notwithstanding the failure of either party to participate in the proceedings. Discovery shall be limited
to mutual exchange of documents relevant to the dispute, controversy or claim; more than two depositions per party shall not be permitted unless the parties otherwise agree or unless compelling need is demonstrated to the arbitrator. The arbitrator
shall be authorized to grant interim relief, including to prevent the destruction of goods or documents involved in the dispute and to provide for security for a prospective monetary award. The arbitrator shall render his decision within thirty
(30) days following the date of the initial evidentiary hearing and shall set forth a statement of facts, his conclusions of law, and his reasoning in writing. Each party shall bear all of its own costs and expenses related to any arbitration
pursuant to this Section 23, including reasonable fees and costs of attorneys and experts and the fees and costs of the arbitrator, and the prevailing party shall not be entitled to recover any such costs and expenses from
the non-prevailing party. The decision of the arbitrator shall be final and binding. The prevailing party shall be entitled to apply to, and obtain from, a court or tribunal having jurisdiction, an order
enforcing the arbitrator’s decision. Notwithstanding anything contained in this Section 23 to the contrary, each party shall have the right to institute judicial proceedings against the other party or anyone acting by,
through or under such other party, in order to enforce the instituting party’s rights through reformation of contract, specific performance, injunction or similar equitable relief, and this Section 23 shall not limit
the remedies granted the Company in Section 7(k). 
 24. Indemnification. With regard to actions or
inactions during the Term, the Company shall provide the Executive with indemnification and directors’ and officers’ liability insurance on terms no less favorable than those applicable to current and former directors or officers of the
Company who served during the Term generally, and any such coverage shall continue after the Term while liability continues to exist. 

[Remainder of page intentionally left blank] 

  
 19 

 IN WITNESS WHEREOF, the Company and the Executive have caused this Agreement to be duly
executed as of the day, month and year first written above. 
  

			
	COMPANY:
	
	CUMULUS MEDIA INC.

 
			
		
	By:	 	  

 
			
	Name:	 	
	Title:	 	

 [Signature Page to Lopez-Balboa Employment Agreement] 

 
	
	EXECUTIVE:
	
	  

	FRANCISCO J. LOPEZ-BALBOA

 [Signature Page to Lopez-Balboa Employment Agreement]

Source: [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00306-of-00352.parquet"}, [{"source": "alea-institute/alea-institute/kl3m-data-edgar-agreements/train-00306-of-00352.parquet"}]]