Document:

Exhibit 10.1

 

SPONSOR SHARE CANCELLATION AND VESTING
AGREEMENT

 

This SPONSOR SHARE
CANCELLATION AND VESTING AGREEMENT (this “Agreement”) is dated as of November 24, 2020, by and among INSU Acquisition
Corp. II, a Delaware corporation (“Parent”), Insurance Acquisition Sponsor II, LLC, a Delaware limited
liability company (“Sponsor II”), and Dioptra Advisors II, LLC, a Delaware limited liability company (“Dioptra”
and together with Sponsor II, the “Sponsors”). Capitalized terms used but not defined herein shall have the
respective meanings ascribed to such terms in the Merger Agreement (as defined below).

 

RECITALS

 

WHEREAS, as of the
date hereof, the Sponsors collectively are the holders of record and the “beneficial owners” (within the meaning of
Rule 13d-3 under the Exchange Act) of (i) 452,500 shares of Parent Common Stock (the “Sponsor Existing Co-Invest Shares”),
(ii) private placement warrants to purchase 150,833 shares of Parent Common Stock and (iii) 7,846,667 shares of Parent Class B
Common Stock (the “Sponsor Promote Shares” and together with the Sponsor Existing Co-Invest Shares, the “Sponsor
Shares”) in the aggregate;

 

WHEREAS, contemporaneously
with the execution and delivery of this Agreement, Parent, INSU II Merger Sub Corp., a Delaware corporation and a wholly owned
subsidiary of Parent (“Merger Sub”), and MetroMile, Inc., a Delaware corporation (the “Company”),
have entered into an Agreement and Plan of Merger and Reorganization (as amended or modified from time to time, the “Merger
Agreement”), dated as of the date hereof, whereby the parties intend to effect a business combination between Parent
and the Company through the merger of Merger Sub with and into the Company, with the Company continuing as the surviving entity,
on the terms and subject to the conditions set forth therein (collectively, the “Transactions”);

 

WHEREAS, pursuant to
the Parent Certificate of Incorporation, each Sponsor Promote Share that is issued and outstanding immediately prior to the Effective
Time shall be converted into, and the holder of such Sponsor Promote Share shall be entitled to receive, one share of Parent Common
Stock for such Sponsor Promote Share on the terms and conditions set forth therein;

 

WHEREAS, in connection
with the Transactions, immediately prior to and contingent upon the Closing, a portion of the Sponsor Promote Shares will be cancelled
as further specified in this Agreement; and

 

WHEREAS, as an inducement
to the Company to enter into the Merger Agreement and to consummate the Transactions, the parties hereto desire to agree to certain
matters as set forth herein.

 

    

     

    

 

AGREEMENT

 

NOW, THEREFORE, in
consideration of the foregoing and the mutual agreements contained herein, and intending to be legally bound hereby, the parties
hereto hereby agree as follows:

 

Article
I

FORFEITURE; SHARE ADJUSTMENTS 

 

1.1 Forfeited
Shares.

  

(a) Immediately
prior to and contingent upon the Closing, each Sponsor shall irrevocably forfeit and surrender for cancellation to Parent, a number
of Sponsor Promote Shares set forth opposite such Sponsor’s name on Schedule I hereto (the “Forfeited Shares“),
which Forfeited Shares shall be deemed automatically cancelled and retired in full, in each case for no consideration (the “Forfeiture”).

 

(b) Parent
shall immediately retire and cancel all of the Forfeited Shares (and shall direct Parent’s transfer agent (or such other
intermediaries as appropriate) to take any and all such actions incident thereto); and

 

(c) The
Sponsors and Parent each shall (i) take such actions as are necessary to cause the Forfeited Shares to be retired and cancelled,
after which the Forfeited Shares shall no longer be issued or outstanding and (ii) provide Parent with evidence that such retirement
and cancellation has occurred.

 

1.2 Earnout
Shares.

 

(a) Immediately
prior to and contingent upon the Closing, a number of Sponsor Promote Shares set forth opposite each Sponsor’s name on Schedule
I hereto (assuming no stock dividend, subdivision, reclassification, recapitalization, split, combination or exchange of shares,
or any similar event occurs between the date hereof and the Closing) shall immediately become subject to the vesting provisions
set forth in Section 1.2(b) (such shares, the “Earnout Shares”) (it being understood that such Earnout
Shares shall no longer be subject to the vesting provisions of the Letter Agreement (as defined below)). Earnout Shares shall continue
to be Earnout Shares if held by any permitted transferee of Earnout Shares. For the avoidance of doubt, it is acknowledged and
agreed that any shares of Parent Common Stock held by the Sponsors that are not Earnout Shares shall not be subject to the provisions
of this Section 1.2.

 

(b) Vesting
Provisions of the Earnout Shares.

 

(i) Fifty
percent (50.00%) of the Earnout Shares held by each Sponsor shall vest in full at such time as the Parent Common Share Price is
greater than $15.00 per share for any period of 20 trading days out of 30 consecutive trading days. “Parent Common Share
Price” means, on any date after the Closing, the closing sale price per share of Parent Common Stock reported as of 4:00
p.m., New York, New York time on such date by Bloomberg, or if not available on Bloomberg, as reported by Morningstar.

 

(ii) 
Fifty percent (50.00%) of the Earnout Shares held by each Sponsor shall vest in full at such time as the Parent Common Share Price
is greater than $17.00 per share for any period of 20 trading days out of 30 consecutive trading days.

 

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(iii) Each
Sponsor shall be entitled to vote its Earnout Shares and receive dividends and other distributions with respect to such Earnout
Shares while they remain unvested; provided that any dividends or other distributions payable with respect to such unvested
Earnout Shares shall be set aside by Parent and shall be paid to each Sponsor upon the vesting of such Earnout Shares (if at all).

 

(c) Acceleration
of Vesting upon a Liquidation Event. In the event of a Liquidation Event following the Closing, Earnout Shares (other than
any Earnout Shares that vested prior to such time pursuant to Section 1.2) shall vest in full upon the occurrence of such
Liquidation Event. “Liquidation Event” means a liquidation, merger, capital stock exchange, reorganization or
other similar transaction involving Parent upon the consummation of which holders of Parent Common Stock would be entitled to exchange
their shares of Parent Common Stock for cash, securities or other property.

 

(d) Equitable
Adjustment. If, between the Closing and a Liquidation Event, the outstanding shares of Parent Common Stock shall have been
changed into a different number of shares or a different class, by reason of any stock dividend, subdivision, reclassification,
recapitalization, split, combination or exchange of shares, or any similar transaction affecting the outstanding shares of Parent
Common Stock, then any number, value (including dollar value) or amount contained herein which is based upon the number of shares
of Parent Common Stock will be equitably adjusted for such dividend, subdivision, reclassification, recapitalization, split, combination
or exchange of shares, or any similar transaction. Any adjustment under this Section 1.2(d) shall become effective at the
close of business on the date any such dividend, subdivision, reclassification, recapitalization, split, combination or exchange
of shares, or any similar transaction becomes effective.

 

(e) Transfers.
No holder of Earnout Shares shall transfer any Earnout Shares to the extent such Earnout Shares are still subject to restrictions
at the time of the contemplated transfer and all certificates representing such Earnout Shares shall contain a legend to such effect;
provided, that Earnout Shares may be transferred to a Permitted Transferee (as defined in that certain letter agreement,
dated as of September 2, 2020, as may be amended or restated from time to time, by and among Parent, Insurance Acquisition Sponsor
II, LLC, Dioptra Advisors, LLC, and the insiders listed on the signature pages thereto (the “Letter Agreement”))
of a Sponsor so long as such Permitted Transferee agrees in writing to be subject to the provisions of Article II hereof.

 

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Article
II

 

REPRESENTATIONS AND WARRANTIES

 

2.1 Representations
and Warranties of the Sponsors. Each Sponsor represents and warrants as of the date hereof to Parent (solely with respect
to itself and not with respect to any other Sponsor) as follows:

 

(a) Organization;
Due Authorization. Such Sponsor is duly organized, validly existing and in good standing under the laws of the jurisdiction
in which it is incorporated, formed, organized or constituted, and the execution, delivery and performance of this Agreement and
the consummation of the transactions contemplated hereby are within such Sponsor's corporate, limited liability company or organizational
powers and have been duly authorized by all necessary corporate, limited liability company or organizational actions on the part
of such Sponsor. This Agreement has been duly executed and delivered by such Sponsor and, assuming due authorization, execution
and delivery by the other parties to this Agreement, this Agreement constitutes a legally valid and binding obligation of such
Sponsor, enforceable against such Sponsor in accordance with the terms hereof (except as enforceability may be limited by bankruptcy
Laws, other similar Laws affecting creditors' rights and general principles of equity affecting the availability of specific performance
and other equitable remedies).

 

(b) Ownership.
Such Sponsor is the record and beneficial owner (as defined in the Securities Act) of, and has good title to, all of (x) the Sponsor
Promote Shares and (y) the Sponsor Existing Co-Invest Shares set forth opposite such Sponsor's name on Schedule I and there
exist no Encumbrances or any other limitation or restriction (including any restriction on the right to vote, sell or otherwise
dispose of such Sponsor Shares (other than transfer restrictions under the Securities Act)) affecting any such Sponsor Shares,
other than any Permitted Encumbrances or pursuant to (i) this Agreement, (ii) the Parent Certificate of Incorporation, (iii) the
Merger Agreement, (iv) the Letter Agreement, (v) the Sponsor Support Agreement or (vi) any applicable securities laws. Other than
the Parent Warrants and pursuant to the Parent Certificate of Incorporation, such Sponsor does not hold or own any rights to acquire
(directly or indirectly) any equity securities of Parent or any equity securities convertible into, or which can be exchanged for,
equity securities of Parent.

 

(c) No
Conflicts. The execution and delivery of this Agreement by such Sponsor does not, and the performance by such Sponsor of its
obligations hereunder will not, (i) conflict with or result in a violation of the organizational documents of such Sponsor or (ii)
require any consent or approval that has not been given or other action that has not been taken by any Person (including under
any contract binding upon such Sponsor or such Sponsor's Sponsor Shares), in each case to the extent such consent, approval or
other action would prevent, enjoin or materially delay the performance by such Sponsor of its obligations under this Agreement.
Each Sponsor has full right and power to enter into this Agreement.

 

(d) Litigation.
There are no Legal Proceedings pending against such Sponsor, or to the knowledge of such Sponsor threatened against such Sponsor,
before (or, in the case of threatened Legal Proceedings, that would be before) any Governmental Authority, which in any manner
challenges or seeks to prevent, enjoin or materially delay the performance by such Sponsor of its obligations under this Agreement.

 

(e) Acknowledgment.
Such Sponsor understands and acknowledges that each of Parent and the Company is entering into the Merger Agreement in reliance
upon such Sponsor's execution and delivery of this Agreement. Such Sponsor had the opportunity to read the Merger Agreement and
this Agreement and has had the opportunity to consult with its tax and legal advisors.

 

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Article
III

 

MISCELLANEOUS

 

3.1 Termination.
This Agreement and all of its provisions shall terminate and be of no further force or effect only (i) automatically upon the termination
of the Merger Agreement in accordance with its terms or (ii) upon the mutual written agreement of Parent and the Sponsors. If the
Closing takes place, this Agreement and all of its surviving provisions shall terminate and be of no further force or effect once
all of the Earnout Shares are no longer subject to the terms and conditions of Section 1.2 hereof. Upon such termination of this
Agreement, all obligations of the parties under this Agreement will terminate, without any liability or other obligation on the
part of any party hereto to any Person in respect hereof or the transactions contemplated hereby. This ARTICLE III shall
survive the termination of this Agreement.

 

3.2 Governing
Law. This Agreement, the rights and duties of the parties hereto, and any disputes (whether in contract, tort or statute) arising
out of, under or in connection with this Agreement will be governed by and construed and enforced in accordance with the Laws of
the State of Delaware, without giving effect to its principles or rules of conflict of laws to the extent such principles or rules
would require or permit the application of the Laws of another jurisdiction. The parties irrevocably and unconditionally submit
to the exclusive jurisdiction of the United States District Court for the District of Delaware or, if such court does not have
jurisdiction, the Delaware state courts located in Wilmington, Delaware, in any action arising out of or relating to this Agreement.
The parties irrevocably agree that all such claims shall be heard and determined in such a Delaware federal or state court, and
that such jurisdiction of such courts with respect thereto will be exclusive. Each party hereby waives, and agrees not to assert,
as a defense in any action, suit or proceeding arising out of or relating to this Agreement that it is not subject to such jurisdiction,
or that such action, suit or proceeding may not be brought or is not maintainable in such courts or that the venue thereof may
not be appropriate or that this Agreement may not be enforced in or by such courts. The parties hereby consent to and grant any
such court jurisdiction over the person of such parties and over the subject matter of any such dispute and agree that mailing
of process or other papers in connection with any such action, suit or proceeding in the manner provided in Section 3.8
or in such other manner as may be permitted by Law, will be valid and sufficient service thereof.

 

3.3 Waiver
of Jury Trial. To the extent not prohibited by applicable law that cannot be waived, each of the parties hereto irrevocably
waives any right it may have to trial by jury in respect of any litigation based on, arising out of, under or in connection with
this Agreement or any course of conduct, course of dealing, verbal or written statement or action of any party hereto or thereto,
in each case, whether now existing or hereafter arising, and whether in contract, tort, statute, equity or otherwise. Each party
hereby further agrees and consents that any such litigation shall be decided by court trial without a jury and that the parties
to this Agreement may file a copy of this Agreement with any court as written evidence of the consent of the parties to the waiver
of their right to trial by jury.

 

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3.4 Assignment.
This Agreement and all of the provisions hereof will be binding upon and inure to the benefit of the parties hereto and their respective
heirs, successors and permitted assigns. Neither this Agreement nor any of the rights, interests or obligations hereunder will
be assigned (including by operation of law) without the prior written consent of the parties hereto.

 

3.5 Specific
Performance. The parties agree that irreparable damage may occur in the event that any of the provisions of this Agreement
were not performed in accordance with their specific terms or were otherwise breached. It is accordingly agreed that monetary damages
may not be an adequate remedy for such breach and the non-breaching party shall be entitled to seek injunctive relief, in addition
to any other remedy that such party may have in law or in equity, and to enforce specifically the terms and provisions of this
Agreement in the chancery court or any other state or federal court within the State of Delaware.

 

3.6 Amendment.
This Agreement may not be amended, changed, supplemented, waived or otherwise modified or terminated, except upon the execution
and delivery of a written agreement executed by the parties hereto.

 

3.7 Severability.
If any provision of this Agreement is held invalid or unenforceable by any court of competent jurisdiction, the other provisions
of this Agreement will remain in full force and effect. Any provision of this Agreement held invalid or unenforceable only in part
or degree will remain in full force and effect to the extent not held invalid or unenforceable.

 

3.8 Notices.
All notices, consents, waivers and other communications under this Agreement must be in writing and will be deemed to have been
duly given (a) if personally delivered, on the date of delivery; (b) if delivered by express courier service of national standing
for next day delivery (with charges prepaid), on the Business Day following the date of delivery to such courier service; (c) if
delivered by telecopy (with confirmation of delivery), on the date of transmission if on a Business Day before 5:00 p.m. local
time of the recipient party (otherwise on the next succeeding Business Day); (d) if delivered by electronic mail, on the date of
transmission if on a Business Day before 5:00 p.m. local time of the business address of the recipient party (otherwise on the
next succeeding Business Day); and (e) if deposited in the United States mail, first-class postage prepaid, on the date of delivery,
in each case to the appropriate addresses or facsimile numbers set forth below (or to such other addresses or facsimile numbers
as a party may designate by notice to the other parties in accordance with this Section 3.8):

 

If to Parent:

 

INSU Acquisition Corp. II

2929 Arch Street, Suite 1703

Philadelphia, PA 19104-2870

Attention: Amanda Abrams

Phone: (215) 701-9555

Email: aabrams@cohenandcompany.com

 

in each case, with a copy (which
shall not constitute notice) to:

Ledgewood PC

Two Commerce Square, Suite 3400

2001 Market Street

Philadelphia, PA 19103

Attention: Derick S. Kauffman

Phone: (215) 731-9450

Email: dkauffman@ledgewood.com

 

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If to a Sponsor:

 

To such Sponsor’s address set forth in Schedule
I

 

with a copy to (which will not constitute notice):

Ledgewood PC

Two Commerce Square, Suite 3400

2001 Market Street

Philadelphia, PA 19103

Attention: Derick S. Kauffman

Phone: (215) 731-9450

Email: dkauffman@ledgewood.com

 

3.9 Counterparts.
This Agreement may be executed in two or more counterparts (any of which may be delivered by facsimile or electronic transmission),
each of which shall constitute an original, and all of which taken together shall constitute one and the same instrument.

 

3.10 Entire
Agreement. This Agreement and the agreements referenced herein constitute the entire agreement and understanding of the
parties hereto in respect of the subject matter hereof and supersedes all prior understandings, agreements or representations
by or among the parties hereto to the extent they relate in any way to the subject matter hereof.

 

[Signature Page Follows]

 

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IN WITNESS WHEREOF, the
parties hereto have each caused this Sponsor Share Cancellation and Vesting Agreement to be duly executed as of the date first
written above.

 

	 	SPONSORS:
	 	 	 
	 	INSURANCE ACQUISITION SPONSOR II, LLC
	 	 	 
	 	By:	/s/ Daniel G. Cohen
	 	 	Name: Daniel G. Cohen
	 	 	Title:  Chief Executive Officer
	 	 	 
	 	DIOPTRA ADVISORS II, LLC
	 	 	 
	 	By:	/s/ Daniel G. Cohen
	 	 	Name: Daniel G. Cohen
	 	 	Title:   Chief Executive Officer
	 	 	 
	 	PARENT:
	 	 	 
	 	INSU ACQUISITION CORP. II
	 	 	 
	 	By:	/s/ John M. Butler
	 	 	Name: John M. Butler
	 	 	Title:   President and Chief Executive Officer

  

 

[Signature Page
to Sponsor Share Cancellation Agreement]

 

    

     

    

 

Schedule I

Sponsors & Sponsor Percentages1

 

	Sponsor	 	Sponsor Promote Shares Vested at Closing	 	 	Sponsor Promote Shares to be Forfeited	 	 	Sponsor Existing Co-Invest Shares	 	 	Earnout Shares	 
	Insurance Acquisition Sponsor II, LLC	 	 	462,000	 	 	 	346,500	 	 	 	452,500	 	 	 	1,501,500	 
	Dioptra Advisors II, LLC	 	 	1,107,333	 	 	 	830,500	 	 	 	--	 	 	 	3,598,834	 
	Total	 	 	1,569,333	 	 	 	1,177,000	 	 	 	452,500	 	 	 	5,100,334	 

 

 

		1	NTD: The Sponsors may deliver an updated version of Schedule
I to Parent prior to the Closing that reallocates among the Sponsors the Sponsor Promote Shares that get forfeited, the Sponsor
Promote Shares that are vested and the Sponsor Promote Shares that become Earnout Shares so long as the total forfeited shares,
total vested shares and total Earnout Shares does not change.Exhibit 10.2

 

STOCKHOLDER SUPPORT AGREEMENT

 

This STOCKHOLDER SUPPORT
AGREEMENT (this “Agreement”) is dated as of November [●], 2020, by and among INSU Acquisition Corp. II,
a Delaware corporation (“Parent”), the Persons set forth on Schedule I hereto (each, a “Stockholder”
and, collectively, the “Stockholders”), and MetroMile, Inc., a Delaware corporation (the “Company”).
Capitalized terms used but not defined herein shall have the respective meanings ascribed to such terms in the Merger Agreement
(as defined below).

 

RECITALS

 

WHEREAS, on November
24, 2020, Parent, INSU II Merger Sub Corp., a Delaware corporation and wholly owned subsidiary of Parent (“Merger
Sub”), and the Company entered into an Agreement and Plan of Merger and Reorganization (as amended or modified from time
to time, the “Merger Agreement”), pursuant to which, among other transactions, upon the terms and subject to
the conditions thereof, Merger Sub will be merged with and into the Company (the “Merger”), with the Company
surviving the Merger as a wholly owned subsidiary of Parent, and each Company Share issued and outstanding as of immediately prior
to the Effective Time will, in each case, be cancelled and automatically converted into the right to receive a certain number of
shares of Parent Common Stock and, subject to certain conditions, cash;

 

WHEREAS, as of the
date hereof, the Stockholders are the holders of record and “beneficial owners” (within the meaning of Rule 13d-3 of
the Exchange Act) of such number of Company Shares as are indicated opposite each of their names on Schedule I attached
hereto (all such Company Shares, together with any Company Shares of which ownership of record or the power to vote (including,
without limitation, by proxy or power of attorney) is hereafter acquired by any such Stockholder during the period from the date
hereof through the Expiration Time (as defined below) are referred to herein as the “Subject Shares”); and

 

WHEREAS, as an inducement
to Parent and the Company to enter into the Merger Agreement and to consummate the Transactions, the parties hereto desire to agree
to certain matters as set forth herein.

 

AGREEMENT

 

NOW, THEREFORE, in
consideration of the foregoing and of the mutual covenants and agreements contained herein, and intending to be legally bound hereby,
the parties hereto hereby agree as follows:

 

     

     

    

 

ARTICLE 1

STOCKHOLDER SUPPORT AGREEMENT; COVENANTS

 

1.1 Transfer
of Shares. During the period commencing on the date hereof and ending on the earlier to occur of (a) the Effective Time, and
(b) such date and time as the Merger Agreement shall be terminated in accordance with Section 7.1 of the Merger Agreement (the
“Expiration Time”), each Stockholder, severally and not jointly, agrees that it shall not (i) sell, assign,
offer, exchange, transfer (including by operation of law), pledge, dispose of, permit to exist any material lien with respect to,
or otherwise encumber any of the Subject Shares or otherwise agree or commit to do any of the foregoing, except for a sale, assignment
or transfer pursuant to the Merger Agreement or to another stockholder of the Company that is a party to this Agreement and bound
by the terms and obligations hereof, (ii) deposit any Subject Shares into a voting trust or enter into a voting agreement
or arrangement or grant any proxy or power of attorney with respect thereto that is inconsistent with this Agreement or (iii) enter
into any contract, option or other arrangement or undertaking with respect to the direct or indirect acquisition or sale, assignment,
transfer (including by operation of law) or other disposition of any Subject Shares; provided, that the foregoing shall
not prohibit the transfer of the Subject Shares (A) if Stockholder is an individual (1) to any member of such Stockholder’s
immediate family, or to a trust for the benefit of Stockholder or any member of Stockholder’s immediate family, the sole
trustees of which are such Stockholder or any member of such Stockholder’s immediate family or (2) by will, other testamentary
document, under the laws of intestacy or by virtue of laws of descent and distribution upon the death of Stockholder; or (B) if
Stockholder is an entity, a partner, member, or affiliate of Stockholder, but only if, in the case of clause (A) and (B), such
transferee shall concurrently execute this Agreement or a joinder agreeing to become a party to this Agreement. Any attempted transfer
of Subject Shares or any interest therein in violation of this Section 1.1 shall be null and void.

 

1.2 New
Shares. In the event that, during the period commencing on the date hereof and ending at the Expiration Time, (a) any Subject
Shares are issued to a Stockholder after the date of this Agreement pursuant to any stock dividend, stock split, recapitalization,
reclassification, combination or exchange of Subject Shares or otherwise, (b) a Stockholder purchases or otherwise acquires beneficial
ownership of any Subject Shares or (c) a Stockholder acquires the right to vote or share in the voting of any Subject Shares (collectively
the “New Securities”), then such New Securities acquired or purchased by such Stockholder shall be subject to
the terms of this Agreement to the same extent as if they constituted the Subject Shares owned by such Stockholder as of the date
hereof.

 

1.3 Agreement
to Vote. Hereinafter until the Expiration Time, each Stockholder, with respect to its, his or her Subject Shares,
severally and not jointly, unconditionally and irrevocably agrees that, at any meeting of the stockholders of the Company (or
any adjournment or postponement thereof), and in any action by written consent of the stockholders of the Company requested
by the Company Board (which written consent shall be delivered promptly, and in any event within twenty-four (24) hours,
after (x) the Registration Statement has been declared effective, and (y) the Company requests such delivery), such
Stockholder shall, if a meeting is held, appear at the meeting, in person or by proxy, or otherwise cause its, his or her
Subject Shares to be counted as present thereat for purposes of establishing a quorum, and such Stockholder shall vote or
provide consent (or cause to be voted or consented), in person or by proxy, all of its, his or her Subject Shares:

 

(a) to
approve and adopt the Merger Agreement and the Transactions (including, but not limited to, the conversion of Company Preferred
Shares into Company Common Shares immediately prior to, and conditioned upon, the Merger);

 

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(b) in
any other circumstances upon which a consent or other approval is required under the Company Organizational Documents or the Management
Agreements or otherwise sought with respect to, or in connection with, the Merger Agreement or the Transactions, to vote, consent
or approve (or cause to be voted, consented or approved) all of such Stockholder’s Subject Shares held at such time in favor
thereof;

 

(c) against
and withhold consent with respect to any issuance or acquisition of shares of capital stock or other equity securities of any Company
Entity, merger, purchase of all or substantially all of the Company’s assets or other business combination transaction
involving any of the Company Entities (other than the Merger Agreement and the Transactions); and

 

(d) against
any proposal, action or agreement that would (i) impede, frustrate, prevent or nullify any provision of this Agreement, the Merger
Agreement or the Merger, (ii) result in a breach in any respect of any covenant, representation, warranty or any other obligation
or agreement of the Company under the Merger Agreement or (iii) result in any of the conditions set forth in Article VI of the
Merger Agreement not being satisfied.

 

Each Stockholder hereby
agrees that it shall not commit or agree to take any action inconsistent with the foregoing. Notwithstanding the foregoing, such
Stockholder shall not vote or provide consent with respect to any of its, his or her Subject Shares to the extent Stockholder is
not a director, officer or affiliate of the Company or holder of Subject Shares representing greater than 5% of the outstanding
shares of capital stock of the Company, or take any other action, in each case to the extent any such vote, consent or other action
would preclude Parent from filing with the SEC the Registration Statement on Form S-4 as contemplated by the Merger Agreement.

 

1.4 No
Challenges. Each Stockholder agrees not to commence, join in, facilitate, assist or encourage, and agrees to take all actions
necessary to opt out of any class in any class action with respect to, any claim, derivative or otherwise, against Parent, Merger
Sub, the Company or any of their respective successors or directors (a) challenging the validity of, or seeking to enjoin the operation
of, any provision of this Agreement or (b) alleging a breach of any fiduciary duty of any person in connection with the evaluation,
negotiation or entry into the Merger Agreement.

 

1.5 Management
Agreements. Each Stockholder hereby agrees and consents to the termination of all Management Agreements to which such Stockholder
is party, effective as of the Effective Time, without any further liability or obligation to the Company, the Company’s Subsidiaries
or Parent. Each Stockholder agrees, confirms, and acknowledges that, after the Effective Time, it, he or she shall not have any
of the rights or privileges provided to each such Stockholder in such applicable Management Agreements.

 

1.6 Registration
Rights Agreement. Each of the Stockholders set forth on Schedule II will deliver, substantially simultaneously with
the Effective Time, a duly executed copy of the Amended and Restated Registration Rights Agreement substantially in the form attached
as Exhibit C to the Merger Agreement.

 

1.7 Lock-Up
Agreements. Each Stockholder will deliver, substantially simultaneously herewith, a duly executed copy of the Lock-Up Agreement
effective as of the Effective Time, substantially in the form attached as Exhibit D to the Merger Agreement.

 

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1.8 Appraisal
and Dissenters’ Rights. Each Stockholder hereby waives, and agrees not to assert or perfect, any rights of appraisal
or rights to dissent from the Merger that Stockholder may have by virtue of ownership of Subject Shares.

 

1.9 Exclusivity.
Unless this Agreement shall have been terminated in accordance with Section 3.1, each Stockholder, severally and not jointly,
agrees not to, and shall not authorize or permit any of its, his or her Affiliates or any of its or their Representatives to,
directly or indirectly, (i) encourage, solicit, initiate, facilitate or continue inquiries regarding a Company Acquisition Proposal;
(ii) enter into discussions or negotiations with, or provide any information to, any person concerning a possible Company Acquisition
Proposal; or (iii) enter into any agreements or other instruments (whether or not binding) regarding a Company Acquisition Proposal.
Each Stockholder shall, and shall cause its, his or her Affiliates and all of its and their Representatives to, immediately cease
and cause to be terminated all existing discussions or negotiations with any Persons (other than the other party to the Merger
Agreement and its Representatives) conducted heretofore with respect to, or that could lead to, any Company Acquisition Proposal.
If any Stockholder receives any inquiry or proposal with respect to a Company Acquisition Proposal at any time prior to the termination
of this Agreement in accordance with Section 3.1, then such Stockholder shall promptly (and in no event later than twenty-four
(24) hours after such Stockholder become aware of such inquiry or proposal) advise Parent and the Company of such inquiry or proposal.

 

REPRESENTATIONS
AND WARRANTIES 

 

2.1 Representations
and Warranties of the Stockholders. Each Stockholder represents and warrants as of the date hereof to Parent and the Company
(solely with respect to itself, himself or herself and not with respect to any other Stockholder) as follows:

 

(a) Organization;
Due Authorization. If such Stockholder is not an individual, it is duly organized, validly existing and in good standing under
the Laws of the jurisdiction in which it is incorporated, formed, organized or constituted, and the execution, delivery and performance
of this Agreement and the consummation of the transactions contemplated hereby are within such Stockholder’s corporate, limited
liability company or organizational powers and have been duly authorized by all necessary corporate, limited liability company
or organizational actions on the part of such Stockholder. If such Stockholder is an individual, such Stockholder has full legal
capacity, right and authority to execute and deliver this Agreement and to perform his or her obligations hereunder. This Agreement
has been duly executed and delivered by such Stockholder and, assuming due authorization, execution and delivery by the other parties
to this Agreement, this Agreement constitutes a legally valid and binding obligation of such Stockholder, enforceable against such
Stockholder in accordance with the terms hereof (except as enforceability may be limited by bankruptcy Laws, other similar Laws
affecting creditors’ rights and general principles of equity affecting the availability of specific performance and other
equitable remedies). If this Agreement is being executed in a representative or fiduciary capacity, the Person signing this Agreement
has full power and authority to enter into this Agreement on behalf of the applicable Stockholder.

 

    4

     

    

 

(b) Ownership.
Such Stockholder is the record and beneficial owner (as defined in the Securities Act) of, and has good title to, all of such Stockholder’s
Subject Shares, and there exist no Liens or any other limitation or restriction (including any restriction on the right to vote,
sell or otherwise dispose of such Subject Shares (other than transfer restrictions under the Securities Act)) affecting any such
Subject Shares, other than Liens pursuant to (i) this Agreement, (ii) the Organizational Documents of the Company, (iii) the Merger
Agreement, (iv) the Amended and Restated Voting Agreement, dated July 18, 2018, and among the Company and the Stockholders party
thereto, as amended (the “Voting Agreement”), or (v) any applicable securities Laws. Such Stockholder’s
Subject Shares are the only equity securities in the Company owned of record or beneficially by such Stockholder on the date of
this Agreement, and none of such Stockholder’s Subject Shares are subject to any proxy, voting trust or other agreement or
arrangement with respect to the voting of such Subject Shares, except as provided hereunder and under the Voting Agreement. Other
than the Company Warrants set forth opposite such Stockholder’s name on Schedule I, such Stockholder does not hold
or own any rights to acquire (directly or indirectly) any equity securities of the Company or any equity securities convertible
into, or which can be exchanged for, equity securities of the Company.

 

(c) No
Conflicts. The execution and delivery of this Agreement by such Stockholder does not, and the performance by such Stockholder
of his, her or its obligations hereunder will not, (i) if such Stockholder is not an individual, conflict with or result in a violation
of the organizational documents of such Stockholder or (ii) require any consent or approval that has not been given or other action
that has not been taken by any Person (including under any Contract binding upon such Stockholder or such Stockholder’s Subject
Shares) to the extent such consent, approval or other action would prevent, enjoin or materially delay the performance by such
Stockholder of its, his or her obligations under this Agreement.

 

(d) Litigation.
There are no actions pending against such Stockholder, or to the knowledge of such Stockholder threatened against such Stockholder,
before (or, in the case of threatened Legal Proceedings, that would be before) any arbitrator or any Governmental Authority, which
in any manner challenges or seeks to prevent, enjoin or materially delay the performance by such Stockholder of its, his or her
obligations under this Agreement.

 

(e) Adequate
Information. Such Stockholder is a sophisticated stockholder and has adequate information concerning the business and financial
condition of Parent and the Company to make an informed decision regarding this Agreement and the transactions contemplated hereby
and has independently and without reliance upon Parent or the Company and based on such information as such Stockholder has deemed
appropriate, made its, his or her own analysis and decision to enter into this Agreement. Such Stockholder acknowledges that Parent
and the Company have not made and do not make any representation or warranty, whether express or implied, of any kind or character
except as expressly set forth in this Agreement. Such Stockholder acknowledges that the agreements contained herein with respect
to the Subject Shares held by such Stockholder are irrevocable.

 

(f) Acknowledgment.
Such Stockholder understands and acknowledges that each of Parent and the Company is entering into the Merger Agreement in reliance
upon such Stockholder’s execution and delivery of this Agreement.

 

    5

     

    

 

ARTICLE 3

 

MISCELLANEOUS

 

Termination.
This Agreement and all of its provisions shall automatically terminate upon the earliest of (a) the Expiration Time and (b)
as to each Stockholder, the written agreement of Parent, the Company and such Stockholder. Upon such termination of this Agreement,
all obligations of the parties under this Agreement will terminate, without any liability or other obligation on the part of any
party hereto to any Person in respect hereof or the transactions contemplated hereby, and no party hereto shall have any claim
against another (and no person shall have any rights against such party), whether under contract, tort or otherwise, with respect
to the subject matter hereof; provided, however, that the termination of this Agreement shall not relieve any party
hereto from liability arising in respect of any breach of this Agreement prior to such termination. This Article III shall
survive the termination of this Agreement.

 

3.2 Governing
Law. This Agreement, and all claims or causes of action (whether in contract or tort) that may be based upon, arise out of
or relate to this Agreement or the negotiation, execution or performance of this Agreement (including any claim or cause of action
based upon, arising out of or related to any representation or warranty made in or in connection with this Agreement) will be governed
by and construed in accordance with the internal Laws of the State of Delaware applicable to agreements executed and performed
entirely within such State.

 

3.3 CONSENT
TO JURISDICTION AND SERVICE OF PROCESS; WAIVER OF JURY TRIAL.

 

(a) THE
PARTIES TO THIS AGREEMENT SUBMIT TO THE EXCLUSIVE JURISDICTION OF THE STATE COURTS LOCATED IN WILMINGTON, DELAWARE OR THE COURTS
OF THE UNITED STATES LOCATED IN WILMINGTON, DELAWARE IN RESPECT OF THE INTERPRETATION AND ENFORCEMENT OF THE PROVISIONS OF THIS
AGREEMENT AND ANY RELATED AGREEMENT, CERTIFICATE OR OTHER DOCUMENT DELIVERED IN CONNECTION HEREWITH AND BY THIS AGREEMENT WAIVE,
AND AGREE NOT TO ASSERT, ANY DEFENSE IN ANY ACTION FOR THE INTERPRETATION OR ENFORCEMENT OF THIS AGREEMENT AND ANY RELATED AGREEMENT,
CERTIFICATE OR OTHER DOCUMENT DELIVERED IN CONNECTION HEREWITH, THAT THEY ARE NOT SUBJECT THERETO OR THAT SUCH ACTION MAY NOT BE
BROUGHT OR IS NOT MAINTAINABLE IN SUCH COURTS OR THAT THIS AGREEMENT MAY NOT BE ENFORCED IN OR BY SUCH COURTS OR THAT THEIR PROPERTY
IS EXEMPT OR IMMUNE FROM EXECUTION, THAT THE ACTION IS BROUGHT IN AN INCONVENIENT FORUM, OR THAT THE VENUE OF THE ACTION IS IMPROPER.
SERVICE OF PROCESS WITH RESPECT THERETO MAY BE MADE UPON ANY PARTY TO THIS AGREEMENT BY MAILING A COPY THEREOF BY REGISTERED OR
CERTIFIED MAIL, POSTAGE PREPAID, TO SUCH PARTY AT ITS ADDRESS AS PROVIDED IN SECTION 3.8.

 

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(b) WAIVER
OF TRIAL BY JURY. EACH PARTY HERETO HEREBY ACKNOWLEDGES AND AGREES THAT ANY CONTROVERSY WHICH MAY ARISE UNDER THIS AGREEMENT IS
LIKELY TO INVOLVE COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE EACH SUCH PARTY HEREBY IRREVOCABLY AND UNCONDITIONALLY WAIVES
ANY RIGHT SUCH PARTY MAY HAVE TO A TRIAL BY JURY IN RESPECT OF ANY LITIGATION DIRECTLY OR INDIRECTLY ARISING OUT OF OR RELATING
TO THIS AGREEMENT OR THE TRANSACTIONS CONTEMPLATED BY THIS AGREEMENT. EACH PARTY CERTIFIES AND ACKNOWLEDGES THAT (I) NO REPRESENTATIVE,
AGENT OR ATTORNEY OF ANY OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF
LITIGATION, SEEK TO ENFORCE THE FOREGOING WAIVER, (II) EACH SUCH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS
WAIVER, (III) EACH SUCH PARTY MAKES THIS WAIVER VOLUNTARILY, AND (IV) EACH SUCH PARTY HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT
BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS SECTION 3.3.

 

3.4 Assignment.
This Agreement and all of the provisions hereof will be binding upon and inure to the benefit of the parties hereto and their respective
heirs, successors and permitted assigns. Neither this Agreement nor any of the rights, interests or obligations hereunder will
be assigned (including by operation of law) without the prior written consent of the parties hereto.

 

3.5 Specific
Performance. The parties hereto agree that irreparable damage may occur in the event that any of the provisions of this Agreement
were not performed in accordance with their specific terms or were otherwise breached. It is accordingly agreed that the parties
hereto shall be entitled to seek an injunction or injunctions to prevent breaches of this Agreement and to enforce specifically
the terms and provisions of this Agreement in the chancery court or any other state or federal court within the State of Delaware,
this being in addition to any other remedy to which such party is entitled at law or in equity.

 

3.6 Amendment;
Waiver. This Agreement may not be amended, changed, supplemented, waived or otherwise modified or terminated, except upon the
execution and delivery of a written agreement executed by Parent, the Company and the Stockholders.

 

3.7 Severability.
If any provision of this Agreement is held invalid or unenforceable by any court of competent jurisdiction, the other provisions
of this Agreement will remain in full force and effect. Any provision of this Agreement held invalid or unenforceable only in part
or degree will remain in full force and effect to the extent not held invalid or unenforceable.

 

    7

     

    

 

3.8 Notices.
All notices and other communications among the parties hereto shall be in writing and shall be deemed to have been duly given (a)
when delivered in person, (b) when delivered after posting in the United States mail having been sent registered or certified mail
return receipt requested, postage prepaid, (c) when delivered by FedEx or other nationally recognized overnight delivery service
or (d) when e-mailed during normal business hours (and otherwise as of the immediately following Business Day), addressed as follows:

 

If to Parent:

 

c/o Insurance Acquisition Corp. II

2929 Arch Street, Suite 1703

Philadelphia, PA 19104-2870

Attention: Amanda Abrams

Phone: (484) 459-3476

Email: aabrams@cohenandcompany.com

 

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

Ledgewood P.C.

Two Commerce Square, Suite 3400

2001 Market Street

Philadelphia, PA 19103

Attention: Derick S. Kauffman

Phone: (215) 731-9450

Facsimile: (215) 735-2513

Email: dkauffman@ledgewood.com

 

If to the Company:

 

MetroMile, Inc.

425 Market Street #700

San Francisco, CA 94105

Attention: Dan Preston

 

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

 

Cooley LLP

101 California Street, 5th Floor

San Francisco, CA 94111

Attention: Rachel Proffitt

Phone: (415) 693-2000

Email: rproffitt@cooley.com; gosterman@cooley.com

 

If to a Stockholder:

 

To such Stockholder’s
address set forth in Schedule I.

 

3.9 Further
Assurances. Each party hereto shall execute and deliver such additional documents as may be necessary or desirable to effect
the transactions contemplated by this Agreement.

 

    8

     

    

 

3.10 Counterparts.
This Agreement may be executed in two or more counterparts (any of which may be delivered by electronic transmission), each of
which shall constitute an original, and all of which taken together shall constitute one and the same instrument.

 

3.11 Entire
Agreement. This Agreement and the agreements referenced herein constitute the entire agreement and understanding of the parties
hereto in respect of the subject matter hereof and supersede all prior understandings, agreements or representations by or among
the parties hereto to the extent they relate in any way to the subject matter hereof.

 

    9

     

    

 

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

 

	 	INSU ACQUISITION CORP. II
	 	 	 
	 	By:	        
	 	Name:	 
	 	Title:	 

 

     

     

    

 

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

 

	 	METROMILE, INC.
	 	 	 
	 	By:	        
	 	Name: 	 
	 	Title:	 

 

     

     

    

 

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

 

 

	 	 
	 	[Stockholder]	 
	 	 	 
	 	Address: 	 
	 	 	 
	 	 	 
	 	Email:	 

 

     

     

    

 

SCHEDULE I

 

Stockholder Subject Shares

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

 

     

     

    

 

SCHEDULE II

 

Amended and Restated Registration Rights
Agreement Signatories

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