Exhibit 10.1


 


FORM OF VOTING
AND SUPPORT AGREEMENT


 


This Voting and Support Agreement
(this “Agreement”) is made as of February 24, 2022, by and among (i) Delwinds Insurance Acquisition Corp.,
a Delaware corporation (together with its successors, the “Purchaser”), (ii) FOXO Technologies Inc.,
a Delaware corporation (the “Company”), and (iii) the undersigned holder (“Holder”)
of capital stock and/or securities convertible into capital stock of the Company. Any capitalized term used but not defined in this Agreement
will have the meaning ascribed to such term in the Merger Agreement.


 


WHEREAS, on the date
hereof, the Purchaser, the Company, DWIN Merger Sub Inc., a Delaware corporation and a wholly-owned subsidiary of the Purchaser (“Merger
Sub”), and the other parties named therein, have entered into that certain Agreement and Plan of Merger (as amended from
time to time in accordance with the terms thereof, the “Merger Agreement”), pursuant to which Merger Sub will
merge with and into the Company, with the Company continuing as the surviving entity (the “Merger”), and as
a result of which, among other matters, all of the issued and outstanding capital stock of the Company as of immediately prior to the
Effective Time shall no longer be outstanding and shall automatically be cancelled and shall cease to exist, in exchange for the right
to receive Stockholder Merger Consideration as set forth in the Merger Agreement, with holders of Company Class B Common Stock receiving
Purchaser Class V Common Stock for such shares of Company Class B Common Stock and all other holders of Company Stock receiving Purchaser
Class A Common Stock for such shares of other Company Stock, all upon the terms and subject to the conditions set forth in the Merger
Agreement and in accordance with the applicable provisions of the DGCL;


 


WHEREAS, it is a condition
to the consummation of the Merger that, on or prior to the Closing Date, the holders of Company Preferred Stock and Company Convertible
Debt shall either exchange or convert all of their issued and outstanding shares of Company Preferred Stock and Company Convertible Debt
for shares of Company Common Stock at the applicable conversion ratio (including any accrued or declared but unpaid dividends or interest)
in accordance with the terms of the Merger Agreement (the “Company Preferred Stock and Convertible Debt Exchange”);


 


WHEREAS, on or prior
to the date hereof, certain holders of Company securities have been presented with and executed certain amended convertible promissory
notes (the “Amended Bridge Notes”) and certain amended warrants to purchase shares of Company Class A Common
Stock (the “Amended Warrants”) in connection the transactions contemplated by the Merger Agreement;


 


WHEREAS, the Board
of Directors of the Company has (a) approved and declared advisable the Merger Agreement, the Ancillary Documents, the Merger and the
other transactions contemplated by any such documents (collectively, the “Transactions”), (b) determined that
the Transactions are fair to and in the best interests of the Company and its stockholders (the “Company Stockholders”)
and (c) recommended the approval and the adoption by each of the Company Stockholders of the Merger Agreement, the Ancillary Documents,
the Merger, the Company Preferred Stock and Convertible Debt Exchange and the other Transactions; and


 


WHEREAS, as a condition
to the willingness of the Purchaser to enter into the Merger Agreement, and as an inducement and in consideration therefor, and in view
of the valuable consideration to be received by Holder thereunder, and the expenses and efforts to be undertaken by the Purchaser and
the Company to consummate the Transactions, the Purchaser, the Company and Holder desire to enter into this Agreement in order for Holder
to provide certain assurances to the Purchaser regarding the manner in which Holder is bound hereunder to vote any shares of capital
stock of the Company which Holder beneficially owns, acquires, holds or otherwise has voting power (the “Shares”)
during the period from and including the date hereof through and including the date on which this Agreement is terminated in accordance
with its terms (the “Voting Period”) with respect to the Merger Agreement, the
Company Preferred Stock and Convertible Debt Exchange, the Merger, the Ancillary Documents and the Transactions.


 






    



    


    

 


NOW, THEREFORE, in
consideration of the premises set forth above, which are incorporated in this Agreement as if fully set forth below, and intending to
be legally bound hereby, the parties hereby agree as follows:


 


1.
Covenant to Vote in Favor of Transactions. Holder agrees, with respect to all of the Shares (and, in the case of
Section 1(b) and Section 1(f), all of the Securities (as defined below)):


 


(a)
during the Voting Period, at each meeting of the Company Stockholders or any class or series thereof, and in each written consent
or resolutions of any of the Company Stockholders in which Holder is entitled to vote or consent, Holder hereby unconditionally and irrevocably
agrees to be present for such meeting and vote (in person or by proxy), or consent to any action by written consent or resolution with
respect to, as applicable, the Shares (i) in favor of, and adopt, the Merger, the Company Preferred Stock and Convertible Debt Exchange,
the Merger Agreement, the Ancillary Documents, any amendments to the Company’s Organizational Documents, and all of the other Transactions
(and any actions required in furtherance thereof), (ii) in favor of the other matters set forth in the Merger Agreement, and (iii) to
vote the Shares in opposition to: (A) any Acquisition Proposal and any and all other proposals (x) for the acquisition of the Company,
(y) that could reasonably be expected to delay or impair the ability of the Company to consummate the Merger, the Company Preferred Stock
and Convertible Debt Exchange, the Merger Agreement or any of the Transactions, or (z) which are in competition with or materially inconsistent
with the Merger Agreement or the Ancillary Documents; (B) other than as contemplated by the Merger Agreement, any material change in (x)
the present capitalization of the Company or any amendment of the Company’s Organizational Documents or (y) the Company’s
corporate structure or business; or (C) any other action or proposal involving any Target Company that is intended, or would reasonably
be expected, to prevent, impede, interfere with, delay, postpone or adversely affect in any material respect the Transactions or would
reasonably be expected to result in any of the conditions to the Closing under the Merger Agreement not being fulfilled;


 


(b)
to execute and deliver all related documentation and take such other action in support of the Merger, the Company Preferred Stock
and Convertible Debt Exchange, the Merger Agreement, any Ancillary Documents, any of the Transactions, as shall reasonably be requested
by the Company or the Purchaser in order to carry out the terms and provision of this Section 1, including, without limitation,
(i) execution and delivery to the Company of a Letter of Transmittal and the Transmittal Documents, (ii) if applicable, delivery of Holder’s
Company Certificate, duly endorsed for transfer, to the Company or the Exchange Agent, as applicable, and any similar or related documents
and such other documents as may be reasonably requested by the Company, the Purchaser or the Exchange Agent, as applicable, (iii) if applicable,
delivery of instrument(s) contemplating the conversion or exchange of each of Holder’s Amended Bridge Notes, Company Convertible
Debt Agreements and any other Company Convertible Securities of Holder, as applicable, for shares of Company Class A Common Stock (or
other similar documentation reasonably requested by the Purchaser, the Company or the Exchange Agent), (iv) if applicable, delivery of
the Amended Warrants or instrument(s) of exercise thereunder, duly endorsed for transfer or notice of exercise, to the Company or the
Exchange Agent, as applicable, and any similar or related documents and such other documents as may be reasonably requested by the Purchaser,
the Company or the Exchange Agent, (v) any actions by written consent of the Company Stockholders presented to Holder, and (vi) any applicable
Ancillary Documents (including, without limitation, a Lock-Up Agreement and a Non-Competition Agreement), customary instruments of conveyance
and transfer, and any consent, waiver, governmental filing, and any similar or related documents;


 






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(c)
 except for transfers expressly permitted by, and effected in accordance with, Section 3(b), not to deposit, and to cause
their Affiliates not to deposit, except as provided in this Agreement, any Shares owned by Holder or his/her/its Affiliates in a voting
trust or subject any Shares to any arrangement or agreement with respect to the voting of such Shares, unless specifically requested to
do so by the Company and the Purchaser in connection with the Merger Agreement, the Ancillary Documents and any of the Transactions;


 


(d)
except as contemplated by the Merger Agreement or the Ancillary Documents, make, or in any manner participate in, directly or indirectly,
a “solicitation” of “proxies” or consents (as such terms are used in the rules of the SEC) or powers of attorney
or similar rights to vote, or seek to advise or influence any Person with respect to the voting of, any shares of the Company capital
stock in connection with any vote or other action with respect to the Transactions, other than to recommend that stockholders of the Company
vote in favor of adoption of the Merger Agreement and the Transactions and any other proposal the approval of which is a condition to
the obligations of the parties under the Merger Agreement (and any actions required in furtherance thereof and otherwise as expressly
provided by Section 1 of this Agreement);


 


(e)
to refrain from exercising any dissenters’ rights or rights of appraisal under applicable Law at any time with respect to
the Merger, the Merger Agreement, the Ancillary Documents and any of the Transactions, including pursuant to the DGCL;


 


(f) without limiting Sections 1(a) and 1(b) above, to: (i) approve and consent to and with respect to any Company Preferred
Stock or Company Convertible Debt held by Holder, participate in the Company Preferred Stock and Convertible Debt Exchange and convert
all shares of Company Preferred Stock and Convertible Debt held by Holder for shares of Company Common Stock at the applicable conversion
ratio (including any accrued or declared but unpaid dividends or interest) as set forth in the Company Charter in accordance with the
terms of the Merger Agreement; and


 


(g)
without limiting Sections 1(a) and 1(b) above, to approve and consent to the termination
of, and terminate, each of the contracts set forth on Schedule 1 to this Agreement to which Holder is a party.


 


2.
 Grant of Proxy. During the Voting Period, Holder, with respect to all of the Shares, hereby irrevocably grants to,
and appoints, the Purchaser and any designee of the Purchaser (determined in the Purchaser’s sole discretion) as Holder’s
attorney-in-fact and proxy, with full power of substitution and resubstitution, for and in Holder’s name, to vote, or cause to be
voted (including by proxy or written consent, if applicable) any Shares owned (whether beneficially or of record) by Holder, solely on
the matters and in the manner specified in Section 1 above. The proxy granted by Holder pursuant to this Section 2 is irrevocable
and is granted in consideration of the Purchaser entering into this Agreement and the Merger Agreement and incurring certain related fees
and expenses. Holder hereby affirms that such irrevocable proxy is coupled with an interest by reason of the Merger Agreement and, except
upon the termination of this Agreement in accordance with Section 5(a), is intended to be irrevocable. Holder agrees, until this
Agreement is terminated in accordance with Section 5(a), to vote its Shares in accordance with Section 1 above.


 


3.
Other Covenants. 


 


(a) No Transfers.
Holder agrees that during the Voting Period it shall not, and shall cause its Affiliates not to, without the Purchaser’s prior
written consent, (A) offer for sale, sell (including short sales), transfer, tender, pledge, encumber, assign or otherwise dispose
of (including by gift) (collectively, a “Transfer”), or enter into any contract, option, derivative,
hedging or other agreement or arrangement or understanding (including any profit-sharing arrangement) with respect to, or consent
to, a Transfer of, any or all of the Securities (as defined below); (B) grant any proxies or powers of attorney with respect to any
or all of the Securities; (C) permit to exist any lien of any nature whatsoever (other than those imposed by this Agreement,
applicable securities Laws or the Company’s Organizational Documents, as in effect on the date hereof) with respect to any or
all of the Securities; or (D) take any action that would have the effect of preventing, impeding, interfering with or adversely
affecting Holder’s ability to perform its obligations under this Agreement. The Company hereby agrees that it shall not permit
any Transfer of the Securities in violation of this Agreement. Holder agrees with, and covenants to, the Purchaser that Holder shall
not request that the Company register the Transfer (book-entry or otherwise) of any certificate or uncertificated interest
representing any Security during the term of this Agreement without the prior written consent of the Purchaser, and the Company
hereby agrees that it shall not effect any such Transfer.


 






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(b)
Permitted Transfers. Section 3(a) shall not prohibit a Transfer of Shares by Holder (i) to any family member or trust
for the benefit of any family member, (ii) to any stockholder, member or partner of Holder, if an entity, (iii) to any Affiliate of Holder,
or (iv) to any person or entity if and to the extent required by any non-consensual Order, by divorce decree or by will, intestacy or
other similar applicable Law, so long as, in the case of the foregoing clauses (i), (ii), (iii) and (iv), the assignee or transferee agrees
to be bound by the terms of this Agreement and executes and delivers to the parties hereto a written consent and joinder memorializing
such agreement. During the term of this Agreement, the Company will not register or otherwise recognize the transfer (book-entry or otherwise)
of any Shares or any certificate or uncertificated interest representing any of Holder’s Shares, except as permitted by, and in
accordance with, this Section 3(b).


 


(c)
Changes to of Securities. In the event of a stock dividend or distribution, or any change in the shares of capital stock
of the Company by reason of any stock dividend or distribution, stock split, recapitalization, combination, conversion, exchange of shares
or the like, the term “Securities” shall be deemed to refer to and include the Securities as well as all such stock dividends
and distributions and any securities into which or for which any or all of the Securities may be changed or exchanged or which are received
in such transaction. Holder agrees during the Voting Period to notify the Purchaser and the Company promptly in writing of the number
and type of any changes to Holder’s ownership of or voting control with respect to Securities, upon Holder’s acquisition or
commitment to acquire any additional Securities or upon any other changes involving Holder relating to capital stock or securities convertible
or exercisable for capital stock of the Company.


 


(d)
Compliance with Merger Agreement. Holder agrees to not during the Voting Period take or agree or commit to take any action
that would make any representation and warranty of Holder contained in this Agreement inaccurate in any material respect. Holder further
agrees that it shall use its commercially reasonable efforts to cooperate with the Purchaser to effect the Merger, the Company Preferred
Stock and Convertible Debt Exchange, all other Transactions, the Merger Agreement, the Ancillary Documents and the provisions of this
Agreement. During the Voting Period, Holder shall not authorize or permit any of its Representatives to, directly or indirectly, take
any action that the Company is prohibited from taking pursuant to Section 5.2 of the Merger Agreement (unless the Purchaser shall
have consented thereto).


 


(e)
Registration Statement. During the Voting Period, Holder agrees to provide to the Purchaser, the Company and their respective
Representatives any information regarding Holder or the Securities that is reasonably requested by the Purchaser, the Company or their
respective Representatives for inclusion in the Registration Statement.


 




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(f)
 Publicity. Holder shall not issue any press release or otherwise make any public statements with respect to the Transactions
or the transactions contemplated herein without the prior written approval of the Company and the Purchaser. Holder hereby authorizes
the Company and the Purchaser to publish and disclose in any announcement or disclosure required by the SEC, The New York Stock Exchange
or the Registration Statement (including all documents and schedules filed with the SEC in connection with the foregoing), Holder’s
identity and ownership of the Securities and the nature of Holder’s commitments and agreements under this Agreement, the Merger
Agreement and any other Ancillary Documents.


 


4.
Representations and Warranties of Holder. Holder hereby represents and warrants to the Purchaser and the Company
as follows:


 


(a)
Binding Agreement. Holder (i) if a natural person, is of legal age to execute this Agreement and is legally competent to
do so and (ii) if not a natural person, is (A) a corporation, limited liability company, company or partnership duly organized and validly
existing under the laws of the jurisdiction of its organization and (B) has all necessary power and authority to execute and deliver this
Agreement, to perform its obligations hereunder and to consummate the transactions contemplated hereby. If Holder is not a natural person,
the execution and delivery of this Agreement, the performance of its obligations hereunder and the consummation of the transactions contemplated
hereby by Holder has been duly authorized by all necessary corporate, limited liability or partnership action on the part of Holder, as
applicable. This Agreement, assuming due authorization, execution and delivery hereof by the other parties hereto, constitutes a legal,
valid and binding obligation of Holder, enforceable against Holder in accordance with its terms (except as such enforceability may be
limited by bankruptcy, insolvency, fraudulent transfer, reorganization, moratorium and other similar laws of general applicability relating
to or affecting creditor’s rights, and to general equitable principles). Holder understands and acknowledges that the Purchaser
is entering into the Merger Agreement in reliance upon the execution and delivery of this Agreement by Holder.


 


(b)
Ownership of Securities. As of the date hereof, Holder has beneficial ownership over the type and number of the Shares and,
to the extent applicable, the other securities issued by the Company set forth under Holder’s name on the signature page hereto
(collectively, the “Securities”), is the lawful owner of such Securities, has the sole power to vote or cause
to be voted such Securities (to the extent such Securities have associated voting rights), and has good and valid title to such Securities,
free and clear of any and all pledges, mortgages, encumbrances, charges, proxies, voting agreements, liens, adverse claims, options, security
interests and demands of any nature or kind whatsoever, other than those imposed by this Agreement, applicable securities Laws or the
Company’s Organizational Documents, as in effect on the date hereof. There are no claims for finder’s fees or brokerage commission
or other like payments in connection with this Agreement or the transactions contemplated hereby payable by Holder pursuant to arrangements
made by Holder. Except for the Shares and other securities of the Company set forth under Holder’s name on the signature page hereto,
as of the date of this Agreement, Holder is not a beneficial owner or record holder of any: (i) equity securities of the Company, (ii)
securities of the Company having the right to vote on any matters on which the holders of equity securities of the Company may vote or
which are convertible into or exchangeable for, at any time, equity securities of the Company or (iii) options, warrants or other rights
to acquire from the Company any equity securities or securities convertible into or exchangeable for equity securities of the Company.


 


(c) No Conflicts.
No filing with, or notification to, any Governmental Authority, and no consent, approval, authorization or permit of any other
person is necessary for the execution of this Agreement by Holder, the performance of its obligations hereunder or the consummation
by it of the transactions contemplated hereby. None of the execution and delivery of this Agreement by Holder, the performance of
its obligations hereunder or the consummation by it of the transactions contemplated hereby shall (i)
conflict with or result in any breach of the certificate of incorporation, bylaws or other comparable organizational documents of
Holder, if applicable, (ii) result in, or give rise to, a violation or breach of or a default under any of the terms of any Contract
or obligation to which Holder is a party or by which Holder or any of the Securities or its other assets may be bound, except
for the Stockholders’ Agreement, dated as of November 13, 2020, by and among the FOXO Management, LLC and GWG Holdings, Inc.
(the “Stockholders’ Agreement”), which will be terminated at the Closing,
or (iii) violate any applicable Law or Order, except for any of the foregoing in clauses (i) through (iii) as would not reasonably
be expected to impair Holder’s ability to perform its obligations under this Agreement in any material respect.


 






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(d)
No Inconsistent Agreements. Holder hereby covenants and agrees that, except for this Agreement and the Stockholders’
Agreement, which will be terminated at the Closing, Holder (i) has not entered into, nor will enter into
at any time while this Agreement remains in effect, any voting agreement or voting trust with respect to the Securities inconsistent with
Holder’s obligations pursuant to this Agreement, (ii) has not granted, nor will grant at any time while this Agreement remains in
effect, a proxy, a consent or power of attorney with respect to the Securities and (iii) has not entered into any agreement or knowingly
taken any action (nor will enter into any agreement or knowingly take any action) that would make any representation or warranty of Holder
contained herein untrue or incorrect in any material respect or have the effect of preventing Holder from performing any of its material
obligations under this Agreement.


 


5.
Miscellaneous.


 


(a)
Termination. Notwithstanding anything to the contrary contained herein, this Agreement shall automatically terminate, and
none of the Purchaser, the Company or Holder shall have any rights or obligations hereunder, upon the earliest to occur of (i) the mutual
written consent of the Purchaser, the Company and Holder, (ii) the Effective Time (following the performance of the obligations of the
parties hereunder required to be performed at or prior to the Effective Time), and (iii) the date of termination of the Merger Agreement
in accordance with its terms. The termination of this Agreement shall not prevent any party hereunder from seeking any remedies (at law
or in equity) against another party hereto or relieve such party from liability for such party’s breach of any terms of this Agreement.
Notwithstanding anything to the contrary herein, the provisions of this Section 5(a) shall survive the termination of this Agreement. 


 


(b)
Binding Effect; Assignment. This Agreement and all of the provisions hereof shall be binding upon and inure to the benefit
of the parties hereto and their respective permitted successors and assigns. This Agreement and all obligations of Holder are personal
to Holder and may not be assigned, transferred or delegated by Holder at any time without the prior written consent of the Purchaser and
the Company, and any purported assignment, transfer or delegation without such consent shall be null and void ab initio. Each of the Company
and the Purchaser may freely assign any or all of its rights under this Agreement, in whole or in part, to any successor entity (whether
by merger, consolidation, equity sale, asset sale or otherwise) without obtaining the consent or approval of Holder.


 


(c)
Third Parties. Nothing contained in this Agreement or in any instrument or document executed by any party in connection
with the transactions contemplated hereby shall create any rights in, or be deemed to have been executed for the benefit of, any person
that is not a party hereto or thereto or a successor or permitted assign of such a party.


 


(d) Governing Law;
Jurisdiction. This Agreement and any dispute or controversy arising out of or relating to this Agreement shall be governed by
and construed in accordance with the laws of the State of New York, without regard to the conflict of law principles thereof. All
Actions arising out of or relating to this Agreement shall be heard and determined exclusively in any state or federal court located
in New York, New York (or in any appellate courts thereof) (the “Specified Courts”). Each party hereto
hereby (i) submits to the exclusive jurisdiction of any Specified Court for the purpose of any Action arising out of or
relating to this Agreement brought by any party hereto and (ii) irrevocably waives, and agrees not to assert by way of motion,
defense or otherwise, in any such Action, any claim that it is not subject personally to the jurisdiction of the above-named courts,
that its property is exempt or immune from attachment or execution, that the Action is brought in an inconvenient forum, that the
venue of the Action is improper, or that this Agreement or the transactions contemplated hereby may not be enforced in or by any
Specified Court. Each party agrees that a final judgment in any Action shall be conclusive and may be enforced in other
jurisdictions by suit on the judgment or in any other manner provided by Law. Each party irrevocably consents to the service of the
summons and complaint and any other process in any other action or proceeding relating to the transactions contemplated by this
Agreement, on behalf of itself, or its property, by personal delivery of copies of such process to such party at the applicable
address set forth or referred to in Section 5(g).
Nothing in this Section 5(d) shall affect the right of any party to serve legal process in any other manner
permitted by applicable law.


 






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(e)
WAIVER OF JURY TRIAL. EACH OF THE PARTIES HERETO HEREBY WAIVES TO THE FULLEST EXTENT PERMITTED BY APPLICABLE LAW ANY RIGHT
IT MAY HAVE TO A TRIAL BY JURY WITH RESPECT TO ANY ACTION DIRECTLY OR INDIRECTLY ARISING OUT OF, UNDER OR IN CONNECTION WITH THIS AGREEMENT
OR THE TRANSACTIONS CONTEMPLATED HEREBY. EACH PARTY HERETO (i) CERTIFIES THAT NO REPRESENTATIVE OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY
OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF ANY ACTION, SEEK TO ENFORCE THAT FOREGOING WAIVER AND (ii) ACKNOWLEDGES
THAT IT AND THE OTHER PARTIES HERETO HAVE BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS
IN THIS SECTION 5(e).


 


(f)
Interpretation. The titles and subtitles used in this Agreement are for convenience only and are not to be considered in
construing or interpreting this Agreement. In this Agreement, unless the context otherwise requires: (i) any pronoun used in this Agreement
shall include the corresponding masculine, feminine or neuter forms, and the singular form of nouns, pronouns and verbs shall include
the plural and vice versa; (ii) “including” (and with correlative meaning “include”) means including without limiting
the generality of any description preceding or succeeding such term and shall be deemed in each case to be followed by the words “without
limitation”; (iii) the words “herein,” “hereto,” and “hereby” and other words of similar import
in this Agreement shall be deemed in each case to refer to this Agreement as a whole and not to any particular section or other subdivision
of this Agreement; (iv) the term “or” means “and/or” and (v) the term “Affiliate” shall mean, with
respect to any specified person, any other person or group of persons acting together that, directly or indirectly, through one or more
intermediaries controls, is controlled by or is under common control with such specified person (where the term “control”
(and any correlative terms) means the possession, direct or indirect, of the power to direct or cause the direction of the management
and policies of such person, whether through the ownership of voting securities, by contract or otherwise). The parties have participated
jointly in the negotiation and drafting of this Agreement. Consequently, in the event an ambiguity or question of intent or interpretation
arises, this Agreement shall be construed as if drafted jointly by the parties hereto, and no presumption or burden of proof shall arise
favoring or disfavoring any party by virtue of the authorship of any provision of this Agreement.


 






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(g) Notices.
All notices, consents, waivers and other communications hereunder shall be in writing and shall be deemed to have been duly given
when delivered (i) in person, (ii) by facsimile or other electronic means (including email), with affirmative confirmation of
receipt, (iii) one Business Day after being sent, if sent by reputable, nationally recognized overnight courier service or (iv)
three (3) Business Days after being mailed, if sent by registered or certified mail, pre-paid and return receipt requested, in each
case to the applicable party at the following addresses (or at such other address for a party as shall be specified by like
notice):


 


	If to the
    Purchaser, to:	with
    a copy (which will not constitute notice) to:
	 	 
	Delwinds Insurance Acquisition Corp.	Ellenoff Grossman & Schole LLP
	One City Centre 	1345 Avenue of the Americas, 11th Floor
	1021 Main Street, Suite 1960	New York, New York 10105
	Houston, TX 77002 	Attn:  Matthew A. Gray, Esq.
	Attn:  Andrew J. Poole	Facsimile No.:  (212) 370-7889
	Telephone:  (713) 337-4077	Telephone
                    No.: (212) 370-1300

	Email: andrew@delwinds.com	Email: mgray@egsllp.com
	 	 
	If to the
    Company, to:	with
    a copy (which will not constitute notice) to:
	 	 
	FOXO Technologies Inc.	Mitchell Silberberg & Knupp LLP
	220 S. 6th St., Suite 1200 	2049 Century Park East, 18th Floor
	Minneapolis, MN 55402	Los Angeles, CA 90067 
	Attn:  Michael Will, General Counsel	Attn: Nimish Patel, Esq.
	Telephone No.:  (612) 562-9447	          Blake
    J. Baron, Esq.
	Email:  mwill@foxotechnologies.com	Facsimile No.:  (310) 312-3100
    
	 	Telephone No.:  (310) 312-2000
    
	 	Email:	nxp@msk.com 
	 	 	bjb@msk.com
	 	 
	 	and
	 	 
	 	Stinson LLP
	 	50 South Sixth Street, 26th Floor
	 	Minneapolis, MN 55402 
	 	Attn: Jill Radloff, Esq.
	 	Facsimile No.:  (612) 335-1657
    
	 	Telephone No.:  (612) 335-1500
    
	 	Email:  jill.radloff@stinson.com
	 	 






	If
    to Holder, to: the address set forth under Holder’s name on the signature page hereto, with a copy (which will not
    constitute notice) to, if not the party sending the notice, each of the Company and the Purchaser (and each of their copies for
    notices hereunder).



 


(h)
Amendments and Waivers. Any term of this Agreement may be amended and the observance of any term of this Agreement may be
waived (either generally or in a particular instance, and either retroactively or prospectively) only with the written consent of the
Purchaser, the Company and the Holder. No failure or delay by a party in exercising any right hereunder shall operate as a waiver thereof.
No waivers of or exceptions to any term, condition, or provision of this Agreement, in any one or more instances, shall be deemed to be
or construed as a further or continuing waiver of any such term, condition, or provision.


 




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(i)  Severability. In case any provision in this Agreement shall be held invalid, illegal or unenforceable in a jurisdiction,
such provision shall be modified or deleted, as to the jurisdiction involved, only to the extent necessary to render the same valid, legal
and enforceable, and the validity, legality and enforceability of the remaining provisions hereof shall not in any way be affected or
impaired thereby nor shall the validity, legality or enforceability of such provision be affected thereby in any other jurisdiction. Upon
such determination that any term or other provision is invalid, illegal or incapable of being enforced, the parties will substitute for
any invalid, illegal or unenforceable provision a suitable and equitable provision that carries out, so far as may be valid, legal and
enforceable, the intent and purpose of such invalid, illegal or unenforceable provision.


 


(j)  Specific
Performance. Holder acknowledges that its obligations under this Agreement are unique, recognizes and affirms that in the event
of a breach of this Agreement by Holder, money damages will be inadequate and the Company and the Purchaser will not have adequate
remedy at law, and agree that irreparable damage would occur in the event that any of the provisions of this Agreement were not
performed by Holder in accordance with their specific terms or were otherwise breached. Accordingly, the Company and the Purchaser
shall be entitled to an injunction or restraining order to prevent breaches of this Agreement by Holder and to enforce specifically
the terms and provisions hereof, without the requirement to post any bond or other security or to prove that money damages would be
inadequate, this being in addition to any other right or remedy to which such party may be entitled under this Agreement, at law or
in equity.


 


(k)
Expenses. Each party shall be responsible for its own fees and expenses (including the fees and expenses of investment bankers,
accountants and counsel) in connection with the entering into of this Agreement, the performance of its obligations hereunder and the
consummation of the transactions contemplated hereby; provided, that in the event of any Action arising out of or relating to this Agreement,
the non-prevailing party in any such Action will pay its own expenses and the reasonable documented out-of-pocket expenses, including
reasonable attorneys’ fees and costs, reasonably incurred by the prevailing party.


 


(l) No Partnership, Agency or Joint Venture. This Agreement is intended to create a contractual relationship among Holder, the
Company and the Purchaser, and is not intended to create, and does not create, any agency, partnership, joint venture or any like relationship
among the parties hereto or among any other Company shareholders entering into voting agreements with the Company or the Purchaser. Holder
is not affiliated with any other holder of securities of the Company entering into a voting agreement with the Company or the Purchaser
in connection with the Merger Agreement and has acted independently regarding its decision to enter into this Agreement. Nothing contained
in this Agreement shall be deemed to vest in the Company or the Purchaser any direct or indirect ownership or incidence of ownership of
or with respect to any Securities.


 


(m)
Further Assurances. From time to time, at another party’s request and without further consideration, each party shall
execute and deliver such additional documents and take all such further action as may be reasonably necessary or desirable to consummate
the transactions contemplated by this Agreement.


 


(n)
Entire Agreement. This Agreement (together with the Merger Agreement to the extent referred to herein) constitutes the full
and entire understanding and agreement among the parties with respect to the subject matter hereof, and any other written or oral agreement
relating to the subject matter hereof existing between the parties is expressly canceled; provided, that, for the avoidance
of doubt, the foregoing shall not affect the rights and obligations of the parties under the Merger Agreement or any Ancillary Document.
Notwithstanding the foregoing, nothing in this Agreement shall limit any of the rights or remedies of the Purchaser or any of the obligations
of Holder under any other agreement between Holder and the Purchaser or any certificate or instrument
executed by Holder in favor of the Purchaser, and nothing in any other agreement, certificate or instrument shall limit any of the rights
or remedies of the Purchaser or any of the obligations of Holder under this Agreement.


 


(o)
Counterparts; Facsimile. This Agreement may be executed in multiple counterparts (including by facsimile or pdf or other
electronic document transmission), each of which shall be deemed an original, and all of which taken together shall constitute one and
the same instrument.


 


[Remainder of Page Intentionally Left Blank;
Signature Page Follows]


 




    9


    


    

 


IN WITNESS WHEREOF, the parties have executed
this Voting Agreement as of the date first written above.


 


	 	The Purchaser:
	 	 
	 	Delwinds Insurance Acquisition Corp.
	 	 	 
	 	By:	               
	 	Name: 	 
	 	Title:	 


 


[Signature Page to
Voting Agreement]



 




     


    


    

 


IN WITNESS WHEREOF, the parties have executed
this Voting Agreement as of the date first written above.


 


	 	The Company:
	 	 
	 	FOXO Technologies Inc.
	 	 	 
	 	By:	               
	 	Name: 	 
	 	Title:	 


 


[Signature Page to Voting Agreement]
 




     


    


    

 


 


IN WITNESS WHEREOF, the parties have executed
this Voting Agreement as of the date first written above.


 


	 	Holder:
	 	 	 
	 	By:	          
	 	Name: 	 



 


	Number and Type of Securities:
	 
	Company Stock
	 
	                                 	 	shares of Company Class A Common Stock
	                                  	 	shares of Company Class B Common Stock
	                                 	 	shares of Series A Preferred Stock



 


Other Company Securities


 


_______________________________________ number/amount
and shares (including the specify type) into which securities are convertible or exercisable, as applicable,


 


Address for Notice:


 


Address:________________________________________________


 


_______________________________________________________


 


_______________________________________________________


 


Facsimile No.:____________________________________________


 


Telephone No.:___________________________________________


 


Email:__________________________________________________


 


[Signature Page to
Voting Agreement]



 




     


    


    

 


Schedule 1


 


FOXO Technologies, Inc. Stockholders’ Agreement, dated as of
November 13, 2020