Type 10-Q Lemonade, Inc. For: Jun 30

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[***]Severance Agreement

[***]THIS SEVERANCE AGREEMENT (the “[***]Severance Agreement[***]”) is entered into as of the Effective Date (as defined below) between Lemonade, Inc. (together with any Affiliate that may employ you from time to time, the “[***]Company[***]”) and Adina Eckstein (“[***]Executive[***]” or “[***]you[***]”).

[***]1.[***]Definitions. The following capitalized terms used herein shall have the following meanings:

[***](a)[***]“[***]Affiliate[***]” means (a) any Subsidiary; and (b) any domestic eligible entity that is disregarded, under Treasury Regulation Section 301.7701-3, as an entity separate from either (i) the Company or (ii) any Subsidiary.

[***](b)[***]“[***]Annual Bonus[***]” means the annual variable cash compensation you are eligible to receive as determined from time to time by the Company, whether acting through the Company’s Board of Directors (the “[***]Board[***]”), a committee thereof or otherwise, based on the achievement of certain Company and/or individual performance objectives.

[***](c)[***]“Base Pay[***]” means your annual base compensation, as determined from time to time by the Company, whether acting through the Board, a committee thereof or otherwise, regardless of whether all or any portion thereof may be deferred under any deferred compensation plan or program of the Company.

[***](d)[***]“[***]Cause[***]” means “Cause” (or any term of similar effect) as defined in your employment agreement with the Company or any Affiliate if such an agreement exists and contains a definition of Cause (or term of similar effect), or, if no such agreement exists or such agreement does not contain a definition of Cause (or term of similar effect), then Cause shall include, but not be limited to: (i) your unauthorized use or disclosure of confidential information or trade secrets of the Company or any Affiliate or any material breach of a written agreement between the Holder and the Company or any Affiliate, including without limitation a material breach of any employment, confidentiality, non-compete, non-solicit or similar agreement; (ii) any refusal to carry out a reasonable directive of the chief executive officer, the Board or your direct supervisor, which involves the business of the Company and/or its Affiliates and was capable of being lawfully performed; (iii) dismissal under the circumstances defined in Section 16 and/or Section 17 of the Israeli Severance Pay Law, 1963; (iv) embezzlement of funds of the Company and/or its Affiliates; your commission of, indictment for or your entry of a plea of guilty or [***]nolo contendere[***] to, a felony under the laws of the United States or any state thereof or any crime involving dishonesty or moral turpitude (or any similar crime in any jurisdiction outside the United States); (v) your gross negligence or willful misconduct or your willful or repeated failure or refusal to substantially perform assigned duties;; or (vi) any acts, omissions or statements by you which the Company reasonably determines to be materially detrimental or damaging to the reputation, operations, prospects or business relations of the Company or any Affiliate.

[***](e)[***]“[***]Change in Control[***]” shall have the meaning set forth in the Incentive Award Plan. Notwithstanding the foregoing, if a Change in Control constitutes a payment or benefit event with respect to any payment or benefit hereunder that provides for the deferral of compensation that is subject to Section 409A, to the extent required to avoid the imposition of additional taxes under Section 409A, such transaction or event will not be deemed a Change in Control unless the transaction qualifies as a “change in control event” within the meaning of Section 409A.

[***](f)[***]“[***]Change in Control Protection Period[***]” means the period beginning on the date three months prior to the consummation of the Change in Control and ending on the first anniversary of such Change in Control.

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

[***](h)[***]“[***]Date of Termination[***]” means the date of termination of your employment for any reason.

[***](i)[***]“Disability”[***] means “Disability” (or any term of similar effect) as defined in your employment agreement with the Company or any Affiliate if such an agreement exists and contains a definition of Disability (or term of similar effect), or, if no such agreement exists or such agreement does not contain a definition of Disability (or term of similar effect), then Disability[***] [***]means an illness (mental or physical) or incapacity, which results in you being unable to perform your duties as an employee of the Company for a period of one hundred eighty (180) days, whether or not consecutive, in any twelve (12) month period.

[***](j)[***]“[***]Equity Awards[***]” means all stock options, restricted stock units, performance stock units and such other equity-based awards granted pursuant to the Incentive Award Plan. For the avoidance of doubt, “Equity Awards” shall not include any cash or cash-based awards granted pursuant to the Incentive Award Plan.

[***](k)[***]“[***]Incentive Award Plan[***]” means Lemonade, Inc. 2020 Incentive Award Plan (or any successor equity incentive plan of the Company).

[***](l)[***]“[***]Lemonade Entities[***]” means Lemonade, Inc. and its direct and indirect Subsidiaries.

[***](m)[***]“[***]Subsidiary[***]” shall mean any entity (other than the Company), whether domestic or foreign, in an unbroken chain of entities beginning with the Company if each of the entities other than the last entity in the unbroken chain beneficially owns, at the time of the determination, securities or interests representing at least fifty percent (50%) of the total combined voting power of all classes of securities or interests in one of the other entities in such chain

[***]2.[***]Term of Agreement[***]. The term of this Agreement will commence as of the closing of the Company’s initial public offering of stock pursuant to an effective registration statement filed under the Securities Act of 1933, as amended (the “[***]Effective Date[***]”) and shall continue in effect until your Date of Termination.

[***]3.[***]Termination and Eligibility for Severance[***].

[***](a)[***]Accrued Benefits[***]. Upon any termination of your employment, you will be paid (i) any and all earned and unpaid portion of your Base Pay through the Date of Termination; (ii) any accrued but unused vacation pay owed to you in accordance with Company practices up to and including the Date of Termination; and (iii) any allowable and unreimbursed business expenses incurred through the Date of Termination that are supported by appropriate documentation in accordance with the Company’s applicable expense reimbursement policies. Hereafter, items (i) through (iii) in this Section 3 are referred to as “[***]Accrued Benefits[***].” If termination of your employment is for any reason other than by the Company without Cause (other than due to death or Disability), you will be entitled to receive [***]only[***] the Accrued Benefits.

[***](b)[***]Severance Payments and Benefits[***]. Subject to Sections 3(c), 5 and 6 of the Agreement:

[***](i)[***]Non-CIC Severance Payments and Benefits[***]. If the Company terminates your employment without Cause (other than as a result of your death or Disability), in each case, outside of the Change in Control Protection Period, then, in addition to the Accrued Benefits, the Company will provide you the following severance and related post-termination benefits (the “[***]Non-CIC Severance Payments and Benefits[***]”):

[***](1)[***]The Company shall, during the period beginning on the Date of Termination and ending on the six (6)-month anniversary of the Date of Termination, pay to you an amount equal to the sum of six (6) months of your Base Pay as in effect immediately prior to the Date of Termination and fifty percent (50%) of your target Annual Bonus for the calendar year in which the Date of Termination occurs (collectively, the “[***]Non-CIC Severance Payment[***]”);

[***](2)[***]The Company shall pay you an amount equal to the aggregate sum of the Company’s share of medical, dental and vision insurance premiums for you and your dependents for the period commencing on the Date of Termination and ending on the sixth month anniversary thereof (as if you had remained employed and based on coverage as of immediately prior to termination). For the avoidance of doubt, if immediately prior to the termination of your employment you were required to contribute towards the cost of premiums as a condition of receiving such insurance, the payment hereunder will not cover any such contributions. The cash payment provided for in this Section 3(b)(i)(2) or Section 3(b)(ii)(2), as applicable, is referred to herein as the “[***]Continued Benefit Payment[***]”);

[***](3)[***]Unless otherwise explicitly set forth in the award agreement for the applicable Equity Award, each outstanding unvested Equity Award held by you immediately prior to the Date of Termination that is subject to vesting based solely upon your continuous service with the Company that would have vested during the six (6)-month period following the Date of Termination had you remained employed shall remain outstanding and shall automatically vest and become exercisable (as applicable) on the Severance Commencement Date; provided that the Release Agreement has become effective and irrevocable as of such date (the “[***]Non-CIC Equity Benefit[***]”); provided, further, that if the Release Agreement has not become effective and irrevocable as of such date, such Equity Awards shall automatically be forfeited for no consideration on such date, and

[***](4)[***]Subject to the provisions of Sections 3(c) and 6, the Non-CIC Severance Payment and Continued Benefit Payment shall be paid in equal installments during the six (6)-month period following the Date of Termination in accordance with the Company’s normal payroll practices beginning on the first payroll date following the 60th day following the Date of Termination (such payroll date, the “[***]Severance Commencement Date[***]”), and with the first installment including any amounts that would have been paid had the Release Agreement been effective and irrevocable on the Date of Termination.

[***](ii)[***]CIC Severance Payments and Benefits[***]. If the Company terminates your employment without Cause (other than as a result of your death or Disability), in each

[***]case, during the Change in Control Protection Period, then, in addition to the Accrued Benefits (and, for the avoidance of doubt, in lieu of the Non-CIC Severance Payments and Benefits), the Company will provide you the following severance and related post-termination benefits (the “[***]CIC Severance Payments and Benefits[***]”):

[***](1)[***]The Company shall pay you an amount equal to the sum of twelve (12) months of your Base Pay as in effect immediately prior to the Date of Termination and your target Annual Bonus for the calendar year in which the Date of Termination occurs, (collectively, the “[***]CIC Severance Payment[***]”);

[***](2)[***]The Company shall pay you an amount equal to the aggregate sum of the Company’s share of medical, dental and vision insurance premiums for you and your dependents for the period commencing on the Date of Termination and ending on the first anniversary thereof (as if you had remained employed and based on coverage as of immediately prior to termination). For the avoidance of doubt, if immediately prior to the termination of your employment you were required to contribute towards the cost of premiums as a condition of receiving such insurance, the payment hereunder will not cover any such contributions; and

[***](3)[***]Unless otherwise explicitly set forth in the award agreement for the applicable Equity Award, any unvested Equity Awards outstanding immediately prior to the Date of Termination shall automatically become fully vested and exercisable (as applicable) on the Severance Commencement Date; provided that the Release Agreement has become effective and irrevocable as of such date (the “[***]CIC Equity Benefit[***]”); provided, further, that if the Release Agreement has not become effective and irrevocable as of such date, such Equity Awards shall automatically be forfeited for no consideration on such date.

[***](4)[***]Subject to the provisions of Sections 3(c) and 6, the CIC Severance Payment and the Continued Benefit Payments shall be paid in equal installments during the twelve (12)-month period following the Date of Termination in accordance with the Company’s normal payroll practices beginning on Severance Commencement Date, and with the first installment including any amounts that would have been paid had the Release Agreement been effective and irrevocable on the Date of Termination shall be made in a lump sum on the Severance Commencement Date.

[***](c)[***]Release[***]. Any amounts payable pursuant to Section 3(b)(i) or Section 3(b)(ii), as applicable (collectively, the “[***]Severance Benefits[***]”), shall be in lieu of notice or any other severance benefits to which you might otherwise be entitled from any Lemonade Entity. Notwithstanding anything to the contrary herein, the Company’s provision of the Severance Benefits will be contingent upon your timely execution and non-revocation of a general waiver and release of claims agreement in a form to be provided by the Company (a “[***]Release Agreement[***]”), subject to the terms set forth herein. You will have twenty-one (21) days (or, in the event that your termination of employment is “in connection with an exit incentive or other employment termination program” (as such phrase is defined in the Age Discrimination in Employment Act of 1967, as amended), forty-five (45) days) following your receipt of the Release Agreement to consider whether or not to accept it. If the Release Agreement is signed and delivered by you to the Company, you will have seven (7) days from the date of delivery to revoke your acceptance of such agreement (the “[***]Revocation Period[***]”). If you do not timely

[***]execute or if you subsequently revoke the Release Agreement, you shall be required to pay to the Company, immediately upon demand therefor, the amount of any payments or benefits you received in connection with any portion of Equity Awards that was eligible to vest pursuant to Section 3(b) (including, without limitation, proceeds received or realized by you from the sale or surrender of any shares underlying such Equity Awards in connection with applicable tax withholding).

[***](d)[***]The provisions of this Section 3 shall supersede in their entirety any severance payment provisions in any employment agreement, severance plan, severance policy, severance program or other severance arrangement maintained by the Company. The Company shall have no further obligation to you in the event of termination of your employment for any reason at any time, other than those obligations specifically set forth in this Section 3.

[***]4.[***]Mitigation[***]. You shall not be required to mitigate the amount of any payment or benefit provided for in Section 3 by seeking other employment or otherwise, nor shall the amount of any payment or benefit provided for in Section 3 be reduced by any compensation earned by you as the result of employment by another employer or by retirement benefits after the Date of Termination or otherwise, subject to Section 5; [***]provided[***], [***]however[***], that any loans, advances or other amounts owed by you to the Company may be offset by the Company and its affiliates against amounts payable to you under Section 3 to the greatest extent permitted by applicable law.

[***]5.[***]Restrictive Covenants and Other Conditions[***]. You acknowledge and agree that you are a party to that certain Proprietary Information, Assignment of Inventions Non Disclosure and Non Compete Agreement, dated as of September 25, 2019, and such agreement remains in full force and effect (the “[***]Restrictive Covenant Agreement[***]”). In the event of (a) your material breach of the Restrictive Covenant Areement, (b) your engagement in any act or omission after the Date of Termination that would have constituted “Cause” under subsection (i) of the definition thereof (without regard for any cure periods therein) for termination of your employment had you remained employed after the Date of Termination, or (c) the Company’s determination in good faith that facts or circumstances existed on the Date of Termination that, if known by the Company on the Date of Termination, would have constituted Cause, the Company shall be entitled to cease all payments and benefits pursuant to Section 3(b), all Equity Awards that vested pursuant to Section 3(b) and any shares of Company stock you received with respect thereto shall immediately be forfeited, without payment therefor, and you shall be required to pay to the Company, immediately upon demand therefor, the amount of any proceeds realized by you from the sale of any such shares.

[***]6.[***]Section 409A Tax Implications[***]. Any payments or benefits required to be provided under this Agreement that is subject to Section 409A of the Code shall be provided only after the date of your “separation from service” with the Company as defined under Section 409A of the Code and the regulations and guidance issued thereunder (collectively, “[***]Section 409A[***]”). The following rules shall apply with respect to distribution of the payments and benefits, if any, to be provided to you under this Agreement:

[***](a)    To the extent applicable, this Agreement shall be interpreted in accordance with Section 409A. Each installment of the payments and benefits provided hereunder shall be treated as a separate “payment” for purposes of Section 409A. If and to the extent (i) any portion of any payment, compensation or other benefit provided to you pursuant to this Agreement in connection with your termination of employment constitutes “nonqualified deferred compensation” within the meaning of Section 409A and (ii) you are a specified employee as defined in Section

[***]409A(a)(2)(B)(i) of the Code, in each case as determined by the Company in accordance with its procedures, by which determinations you agree that you are bound, such portion of the payment, compensation or other benefit shall not be paid until the first business day that is six (6) months plus one (1) day or more after the date of “separation from service” (as determined under Section 409A) (the “[***]New Payment Date[***]”), except such earlier date as Section 409A may then permit. The aggregate of any payments that otherwise would have been paid to you during the period between the date of separation from service and the New Payment Date shall be paid to you in a lump sum on such New Payment Date, and any remaining payments will be paid on their original schedule.

[***](b)[***]The Company and its employees, agents and representatives make no representations or warranty and shall have no liability to you or any other person if any provisions of or payments, compensation or other benefits under this Agreement are determined to constitute nonqualified deferred compensation subject to Section 409A but do not satisfy the conditions of that section. Notwithstanding any provision of this Agreement to the contrary, in the event that following the Effective Date the Board determines that this Agreement may be subject to Section 409A, the Board may (but is not obligated to), without your consent, adopt such amendments to this Agreement or adopt other policies and procedures (including amendments, policies and procedures with retroactive effect), or take any other actions, that the Board determines are necessary or appropriate to (i) exempt this Agreement from Section 409A and/or preserve the intended tax treatment of the benefits provided with respect to this Agreement or (ii) comply with the requirements of Section 409A and thereby avoid the application of any penalty taxes under Section 409A.

[***]7.[***]Section 280G[***]. If any payment or benefit you would receive or retain under this Severance Agreement, when combined with any other payment or benefit you receive or retain in connection with a “change in control event” within the meaning of Section 280G of the Code and the regulations and guidance thereunder (“[***]Section 280G[***]”), would (a) constitute a “parachute payment” within the meaning of Section 280G of the Code, and (b) but for this Section 7, be subject to the excise tax imposed by Section 4999 of the Code (the “[***]Excise Tax[***]”), then such Payment shall be either payable in full or in such lesser amount as would result in no portion of the Payment being subject to the Excise Tax, whichever of the foregoing amounts, taking into account the applicable federal, state and local employment taxes, income taxes, and the Excise Tax, results in your receipt, on an after-tax basis, of the greater amount of the Payment notwithstanding that all or some portion of the Payment may be subject to the Excise Tax. All determinations required to be made under this Section 7, including whether and to what extent the Payment shall be reduced and the assumptions to be utilized in arriving at such determination, shall be made by a nationally recognized certified public accounting firm or consulting firm experience in matters regarding Section 280G of the Code as may be designated by the Company (the “[***]280G Advisor[***]”). The 280G Advisor shall provide detailed supporting calculations both to you and the Company at such time as is requested by the Company. All fees and expenses of the Accounting Firm shall be borne solely by the Company. Any final determination by the 280G Advisor shall be binding upon you and the Company. For purposes of making the calculations required by this Section 7, the 280G Advisor may make reasonable assumptions and approximations concerning applicable taxes and may rely on reasonable, good-faith interpretations concerning the application of Sections 280G and 4999 of the Code.

[***]8.[***]Withholding[***]. The Company shall be entitled to withhold from any amounts payable under this Agreement any federal, state, local or foreign withholding or other taxes or charges that the Company is

[***]required to withhold. The Company shall be entitled to rely on an opinion or advice of counsel if any questions as to the amount or requirement of withholding arise.

[***]9.[***]Miscellaneous[***].

[***](a)[***]This Agreement, together with any written employment agreement or offer letter to which you may be a party and any agreements referenced herein, will constitute our entire agreement as to your employment by the Company and will supersede any prior agreements or understandings, whether in writing or oral, with respect to the subject matter hereof, other than with respect to any agreements between you and the Company with respect to confidential information, intellectual property, non-competition, non-solicitation, non-disparagement, nondisclosure of proprietary information, inventions and injunctive relief, including, without limitation, the Restrictive Covenant Agreement); [***]provided[***] that Section 9(f) supersedes and replaces any prior dispute resolution provisions in any other prior agreement between you and the Company (including, without limitation, the Restrictive Covenant Agreement).

[***](b)[***]This Agreement may be executed in more than one counterpart, each of which shall be deemed to be an original, and all such counterparts together shall constitute one and the same instrument.

[***](c)[***]The provisions of this Agreement are severable and if any one or more provisions may be determined to be illegal or otherwise unenforceable, in whole or in part, the remaining provisions of this Agreement shall nevertheless be binding and enforceable and except to the extent necessary to reform or delete such illegal or unenforceable provision, this Agreement shall remain unmodified and in full force and effect.

[***](d)[***]This Agreement is personal in nature and neither of the parties hereto shall, without the written consent of the other, assign or otherwise transfer this Agreement or its obligations, duties and rights under this Agreement; provided, however, that in the event of the merger, consolidation, transfer or sale of all or substantially all of the assets of the Company, this Agreement shall, subject to the provisions hereof, be binding upon and inure to the benefit of such successor and such successor shall discharge and perform all of the promises, covenants, duties and obligations of the Company hereunder.

[***](e)[***]All notices shall be in writing and shall be delivered personally (including by courier), sent by facsimile transmission (with appropriate documented receipt thereof), by overnight receipted courier service (such as UPS or Federal Express) or sent by certified, registered or express mail, postage prepaid, to the Company at the following address: Lemonade, Inc., 5 Crosby Street, 3[***]rd[***] Floor, Attn: Head of Legal, and to you at the most current address we have in your employment file. Any such notice shall be deemed given when so delivered personally, or if sent by facsimile transmission, when transmitted, or, if by certified, registered or express mail, postage prepaid mailed, forty-eight (48) hours after the date of deposit in the mail. Any party may, by notice given in accordance with this paragraph to the other party, designate another address or person for receipt of notices hereunder.

[***](f)[***]Disputes. [***]The parties will keep confidential, and will not disclose to any person, except as may be required by law or the rules and regulations of the Securities and Exchange

[***]Commission or other government agencies, the existence of any controversy hereunder or the status or court resolution thereof.

[***](g)[***]This Agreement shall be governed by and interpreted in accordance with the laws of the State of Israel, without regard to the conflict of laws provisions thereof or of any other jurisdiction.[***] [***]Any dispute arising under or relating to this Agreement shall be resolved by the competent courts in Tel Aviv, and each of the parties hereby submits irrevocably to the exclusive jurisdiction of such venue

[***]10.[***]Acceptance[***]. You may accept the terms and conditions described herein by confirming your acceptance in writing. Please send your countersignature to this Agreement to the Company, or via e-mail to me, which execution will evidence your agreement with the terms and conditions set forth herein.

[***]IN WITNESS WHEREOF, each of the parties has executed this Severance Agreement, in the case of the Company by its duly authorized officer, as of the day and year first above written.

[***]EXECUTIVE:

[***]/s/ Adina Eckstein
[***]Name: Adina Eckstein
[***]Title: Chief Operating Officer

[***]COMPANY:

[***]By: [***]/s/ Daniel Schreiber
[***]Name: Daniel Schreiber
[***]Title: Chief Executive Officer

[***]Signature Page to Severance Agreement

[***]|

[***]LEMONADE, INC.
2020 INCENTIVE AWARD PLAN

[***]
RESTRICTED STOCK UNIT AWARD GRANT NOTICE AND

[***]RESTRICTED STOCK UNIT AGREEMENT

[***]Lemonade, Inc., a Delaware corporation (the “[***]Company[***]”), pursuant to its 2020 Incentive Award Plan, as amended from time to time (the “[***]Plan[***]”), hereby grants to the holder listed below (“[***]Participant[***]”) the number of Restricted Stock Units set forth below (the “[***]RSUs[***]”). The RSUs are subject to the terms and conditions set forth in this Restricted Stock Unit Grant Notice (the “[***]Grant Notice[***]”), the Restricted Stock Unit Agreement attached hereto as [***]Exhibit A[***] including any Appendix thereto (the “[***]Agreement[***]”), the Plan, and the Appendix for Israeli Taxpayers, as adopted by the Company and amended from time to time (the “[***]IL Appendix[***]”), each of which is incorporated herein by reference. Unless otherwise defined herein, the terms defined in the Plan shall have the same defined meanings in the Grant Notice and the Agreement. All references to the Plan under this Grant Notice, shall refer to the IL Appendix as well, and the term “Plan” shall include the IL Appendix.

[***]Participant:

[***]Grant Date:
[***]Number of RSUs:
[***]Type of Shares Issuable: [***]Common Stock
[***]Vesting Schedule:

[***]* [***]The Award granted under this Grant Notice and the Agreement attached hereto shall be deemed as a 102 Capital Gains Track Grant, as set forth in the IL Appendix, and shall be subject to [***]Section 102 of the ITO and any regulations, rules or orders promulgated thereunder all as amended from time to time[***].[***]

[***]By accepting this Award electronically through the Plan service provider’s online grant acceptance policy, Participant agrees to be bound by the terms and conditions of the Plan, the IL Appendix, the Agreement and the Grant Notice. Participant has reviewed the Agreement, the Plan and the Grant Notice in their entirety, has had an opportunity to obtain the advice of counsel prior to executing the Grant Notice and fully understands all provisions of the Grant Notice, the Agreement, and the Plan. Participant hereby agrees to accept as binding, conclusive and final all decisions or interpretations of the Administrator upon any questions arising under the Plan, the Grant Notice or the Agreement.

[***]LEMONADE, INC.

[***]PARTICIPANT

[***]By: [***]By:
[***]Print Name: [***]Print Name:
[***]Title:

[***]EXHIBIT A

[***]TO RESTRICTED STOCK UNIT AWARD GRANT NOTICE

[***]RESTRICTED STOCK UNIT AWARD AGREEMENT

[***]Pursuant to the Grant Notice to which this Agreement is attached, the Company has granted to Participant the number of RSUs set forth in the Grant Notice.

[***]ARTICLE I.

[***]
GENERAL

[***]Section I.1[***]Defined Terms[***]. Capitalized terms not specifically defined herein shall have the meanings specified in the Plan, the IL Appendix or the Grant Notice. For purposes of this Agreement,

[***](a)[***]“[***]Cessation Date[***]” shall mean the date of Participant’s Termination of Service (regardless of the reason for such termination).

[***](b)[***]“[***]Company Group[***]” shall mean the Company and its Affiliates.

[***](c)[***]“[***]Company Group Member[***]” shall mean each member of the Company Group.

[***](d)[***]“[***]Disability[***]” shall have the meaning ascribed to such term in any relevant employment agreement between Participant and a Company Group Member; provided that, in the absence of such agreement containing such definition, “Disability” shall mean permanent disability or incapacity as determined in accordance with the Company’s disability insurance policy, if such a policy is then in effect, or if no such policy is then in effect, such permanent disability or incapacity shall be determined by the Board in its good faith judgment based upon inability to perform the essential functions of his or her position, with reasonable accommodation by the Company, for a period in excess of 180 days during any period of 365 calendar days.

[***](e)[***]“[***]Participating Company[***]” shall mean the Company or any of its parents or Subsidiaries.

[***]Section I.2[***]Incorporation of Terms of Plan[***]. Except where this Agreement explicitly states that this Agreement prevails over the Plan, the RSUs and the shares of Common Stock issued to Participant hereunder (“[***]Shares[***]”) are subject to the terms and conditions set forth in this Agreement, the Plan and the IL Appendix, which is incorporated herein by reference. In the event of any inconsistency between the Plan, the IL Appendix and this Agreement, the terms of the Plan and the IL Appendix shall control. All references to the Plan under this Agreement, shall refer to the IL Appendix as well, and the term “Plan” shall include the IL Appendix.

[***]
[***]ARTICLE II.

[***]AWARD OF RESTRICTED STOCK UNITS

[***]Section II.1[***]Award of RSUs[***]

[***](a)[***]In consideration of Participant’s past and/or continued employment with or service to a Participating Company and for other good and valuable consideration, effective as of the grant date set forth in the Grant Notice (the “[***]Grant Date[***]”), the Company hereby grants to Participant the number of RSUs set forth in the Grant Notice, upon the terms and conditions set forth in the Grant Notice, the Plan and this Agreement, subject to adjustment as provided in Section 12.2 of the Plan. [***]The Trustee will hold the RSUs or the Shares to be issued upon vesting of the RSUs for the benefit of the Participant as set forth below.

[***](b)[***]Each RSU represents the right to receive one Share at the times and subject to the conditions set forth herein. However, unless and until the RSUs have vested, Participant will have no right to the payment of any Shares subject thereto. Prior to the actual delivery of any Shares, the RSUs will represent an unsecured obligation of the Company, payable only from the general assets of the Company.

[***]Section II.2[***]Vesting of RSUs[***].

[***](a)[***]Subject to Participant’s continued employment with or service to a Participating Company on each applicable vesting date and subject to the terms of this Agreement, the RSUs shall vest in such amounts and at such times as are set forth in the Grant Notice.

[***](b)[***]In the event Participant incurs a Termination of Service, except as may be otherwise provided herein or by the Administrator or as set forth in a written agreement between Participant and the Company, Participant shall immediately forfeit any and all RSUs granted under this Agreement that have not vested or do not vest on or prior to the date on which such Termination of Service occurs, and Participant’s rights in any such RSUs that are not so vested shall lapse and expire.

[***](c)[***]Notwithstanding the Grant Notice or the provisions of [***]Section 2.2(a)[***] and [***]Section 2.2(b)[***], in the event Participant incurs a Termination of Service for Cause or, except as may be otherwise provided by the Administrator or as set forth in a written agreement between Participant and the Company, Participant shall immediately forfeit any and all RSUs granted under this Agreement (whether or not vested), and Participant’s rights in any such RSUs shall lapse and expire.

[***]Section II.3

[***]    (a)    [***]Distribution or Payment of RSUs[***]. Participant’s RSUs shall be distributed in Shares (either in book-entry form or otherwise) which will be registered in the name of the Trustee, and will be deposited in the Trustee’s account (for the benefit of the Participant) as soon as administratively possible following each applicable vesting date and, in any event, no later than March 15[***]th[***] of the calendar year following the year in which the applicable vesting date occurs. Notwithstanding the foregoing, the Company may delay a distribution or payment in settlement of RSUs if it reasonably determines that such payment or distribution will violate federal securities laws or any other Applicable Law, provided that such distribution or payment shall be made at the earliest date at which the Company reasonably determines that the making of such distribution or payment will not cause such violation.

[***]    (b)    All distributions shall be made by the Company in the form of whole Shares, and any fractional share shall be distributed in cash in an amount equal to the value of such fractional share determined based on the Fair Market Value as of the date immediately preceding the date of such distribution.

[***]    (c)    [***]Additional Requirements[***]. In order for the Company to distribute Shares upon the vesting of Participant’s RSUs, Participant hereby agrees to sign any and all documents required by any applicable law (including Section 102) and/or reasonably required by the Administrator and/or the Trustee. Participant further agrees that in the event that the Company and its counsel deem it necessary or advisable, in their sole discretion, the issuance of Shares may be conditioned upon certain representations, warranties, and acknowledgements by Participant.

[***]Section II.4[***]Conditions to Issuance of Certificates[***]. The Company shall not be required to issue or deliver any certificate or certificates for any Shares or to cause any Shares to be held in book-entry form prior to the fulfillment of all of the following conditions: (a) the admission of the Shares to listing on all stock exchanges on which such Shares are then listed, (b) the completion of any registration or other qualification of the Shares under any state or federal law or under rulings or regulations of the Securities and Exchange Commission or other governmental regulatory body, which the Administrator shall, in its absolute discretion, deem necessary or advisable, and (c) the obtaining of any approval or other clearance from any state or federal governmental agency that the Administrator shall, in its absolute discretion, determine to be necessary or advisable.

[***]Section II.5[***]Tax[***]. Notwithstanding any other provision of this Agreement:

[***](a)[***]As set forth in Section 10.2 of the Plan, the Company and or the Trustee shall have the authority and the right to deduct or withhold, or to require the Participant to remit to the Company, an amount sufficient to satisfy all applicable federal, state and local taxes required by law to be withheld with respect to any taxable event arising in connection with the Restricted Stock Units. In the event that the Company and/or the Trustee determine that it is required to withhold any tax with respect to the disposition of the Participant’s Shares pursuant to the vesting of RSUs, the Participant undertakes to make all arrangements satisfactory to the Company, any Participating Company and/or the Trustee to enable it to satisfy all withholding requirements, including [***], but not limited, to (i) deducting the amount so required to be withheld from any other amount then or thereafter payable to Participant, including by deducting any such amount from Participant’s salary or other amounts payable to the Participant, to the maximum extent permitted under law and/or (ii) requiring Participant to pay to the Company or any Participating Company the amount so required to be withheld as a condition of the issuance, delivery, distribution or release of any Shares and/or (iii) by causing the sale of any Shares held by or on behalf of Participant to cover such liability up to the amount required to satisfy minimum statutory withholding requirements. [***].

[***](b)[***]In general, taxable income that should be attributed to the Participant as a result of the grant of the RSUs will be tax-free on the date of grant, but will be taxed on the sale of Shares issued upon the vesting of the RSUs or transfer of Shares from the Trustee to the Participant. Upon a sale of Shares, the Trustee will calculate the taxable amount for such transaction and will withhold the applicable tax from the proceeds it receives. The remaining net proceeds after the tax deduction will be wired to the Participant’s personal account.

[***](c)[***]The Participant will not be entitled to receive the Shares from the Company and the Shares shall not be sold or released from the control of the Trustee prior to the full payments of the Participant’s tax liabilities relating to the RSUs and the Shares.

[***](d)[***]Any tax consequences arising from the grant or distribution of the RSUs, from the payment for Shares covered thereby or from any other event or act (of the Company and/or its Affiliates, or the Trustee or the Participant), hereunder, shall be borne solely be Participant. Participant is

[***]ultimately liable and responsible for all taxes owed in connection with the RSUs, regardless of any action the Trustee, the Company or any other Participating Company takes with respect to any tax withholding obligations that arise in connection with the RSUs. No Participating Company makes any representation or undertaking regarding the treatment of any tax withholding in connection with the awarding, vesting or payment of the RSUs or the subsequent sale of Shares. The Participating Companies do not commit and are under no obligation to structure the RSUs to reduce or eliminate Participant’s tax liability.

[***](e)[***]As above mentioned, the receipt of the RSUs and the acquisition of the Shares to be issued upon the vesting of the RSUs may result in tax consequences. PARTICIPANT IS ADVISED TO CONSULT A TAX ADVISOR WITH RESPECT TO THE TAX CONSEQUENCES OF RECEIVING THE RSUS OR DISPOSING OF THE SHARES.

[***]Section II.6[***]Rights as Stockholder[***]. Neither Participant nor any person claiming under or through Participant will have any of the rights or privileges of a stockholder of the Company in respect of any Shares deliverable hereunder unless and until certificates representing such Shares (which may be in book-entry form) will have been issued and recorded on the records of the Company or its transfer agents or registrars and delivered to Participant (including through electronic delivery to a brokerage account). Only after the Trustee shall release the Shares, in accordance with the terms of the Plan and this Agreement, and such Shares will be registered under the name of the Participant, Participant will have all the rights of a stockholder of the Company with respect to such Shares, including, without limitation, the right to receipt of dividends and distributions on such Shares.

[***]Section II.7[***]Limitations and Conditions Relating to 102 Capital Gains Track Grant.

[***](a)[***]The Participant understands and agrees that this RSU Award is granted to him or her in his or her capacity as an Eligible 102 Participant and therefore, is intended to qualify as a 102 Capital Gains Track Award (as such terms are defined in the IL Appendix).

[***](b)[***]By accepting this RSU Award electronically through the Plan service provider’s online grant acceptance policy, Participant hereby: (i) acknowledges and confirms that he or she is familiar with the provisions of Section 102 and the regulations and rules promulgated thereunder, including without limitations, with respect to the RSUs granted hereunder, their holding by the Trustee in trust for the benefit of the Participant and the tax implications applicable to such grant; and (ii) accepts the RSU Award subject to all of the terms and conditions of the Agreement, the Plan and the IL Appendix.

[***](c)[***]The RSUs granted to the Participant herein shall be paid in Shares only. In no event shall any of such RSUs be paid in cash, notwithstanding any discretion contained in the Plan, or any provision in the Agreement to the contrary.

[***](d)[***]The Participant hereby agrees to the provisions of the Trustee engagement form signed between the Company and the Trustee, in the form attached to this Agreement as [***]Schedule A[***].

[***](e)[***]The RSU Award shall be deposited with the Trustee for the Participant’s benefit in accordance with the terms of the Plan and the IL Appendix. The Shares resulting from the vesting of such RSU Award shall also be held by the Trustee in its trust account for at least the Required Holding Period.

[***](f)[***]In order for the grant of this RSU Award to be considered as a 102 Capital Gains Track Grant the Participant must not sell or release from trust any Share received upon the vesting of an RSU and/or any Share received subsequently following any realization of rights until the lapse of the

[***]Required Holding Period. Notwithstanding the above, if any such sale or release occurs during the Required Holding Period, the sanctions and any other adverse tax consequences under Section 102 and under any rules or regulation or orders or procedures promulgated thereunder, shall apply to and shall be borne by the Participant.

[***](g)[***]In the event that bonus Shares or dividends in the form of additional RSUs or Shares are issued with respect to the Shares held with the Trustee, or as a result of an adjustment made pursuant to the Plan, such RSUs or Shares shall be deposited or controlled by the Trustee, as the case may be, for the benefit of the Participant and the provisions of Section 102 of the ITO shall apply to such RSUs or Shares for all purposes.

[***]ARTICLE III.

[***]OTHER PROVISIONS

[***]Section III.1[***]Administration[***]. The Administrator shall have the power to interpret the Plan, the Grant Notice and this Agreement and to adopt such rules for the administration, interpretation and application of the Plan, the Grant Notice and this Agreement as are consistent therewith and to interpret, amend or revoke any such rules. All actions taken and all interpretations and determinations made by the Administrator will be final and binding upon Participant, the Company and all other interested persons. To the extent allowable pursuant to Applicable Law, no member of the Committee or the Board will be personally liable for any action, determination or interpretation made with respect to the Plan, the Grant Notice or this Agreement.

[***]Section III.2[***]Obligations to the Company[***]. Participant agrees to comply with the terms and conditions of that certain Proprietary Information, Assignment of Inventions Non-Disclosure and Non-Compete Agreement by and between Participant and the Company, which is incorporated by reference herein, and Participant acknowledges and agrees that the grant of the RSUs shall be in material part in consideration of Participant’s reaffirmation of Participant’s agreement to comply with the covenants set forth therein.

[***]Section III.3[***]RSUs Not Transferable[***]. The RSUs may not be sold, pledged, assigned or transferred in any manner other than by will or the laws of descent and distribution, unless and until the Shares underlying the RSUs have been issued, and all restrictions applicable to such Shares have lapsed. No RSUs or any interest or right therein or part thereof shall be liable for the debts, contracts or engagements of Participant or his or her successors in interest or shall be subject to disposition by transfer, alienation, anticipation, pledge, encumbrance, assignment or any other means whether such disposition be voluntary or involuntary or by operation of law by judgment, levy, attachment, garnishment or any other legal or equitable proceedings (including bankruptcy), and any attempted disposition thereof shall be null and void and of no effect, except to the extent that such disposition is permitted by the preceding sentence. Notwithstanding the foregoing, with the consent of the Administrator, the RSUs may be transferred to Permitted Transferees, pursuant to any such conditions and procedures the Administrator may require.

[***]Section III.4[***]Adjustments[***]. The Administrator may accelerate the vesting of all or a portion of the RSUs in such circumstances as it, in its sole discretion, may determine. Participant acknowledges that the RSUs and the Shares subject to the RSUs are subject to adjustment, modification and termination in certain events as provided in this Agreement and the Plan, including Section 12.2 of the Plan.

[***]Section III.5[***]Notices[***]. Any notice to be given under the terms of this Agreement to the Company shall be addressed to the Company in care of the Secretary of the Company at the Company’s principal office, and any notice to be given to Participant shall be addressed to Participant at Participant’s last address or email address reflected on the Company’s records. By a notice given pursuant to this [***]Section 4.4[***], either party may hereafter designate a different address for notices to be given to that party. Any notice shall be deemed duly given when sent via email or when sent by certified mail (return receipt requested) and deposited (with postage prepaid) in a post office or branch post office regularly maintained by the United States Postal Service or similar foreign entity.

[***]Section III.6[***]Titles[***]. Titles are provided herein for convenience only and are not to serve as a basis for interpretation or construction of this Agreement.

[***]Section III.7[***]Governing Law[***]. The laws of the State of Delaware shall govern the interpretation, validity, administration, enforcement and performance of the terms of this Agreement regardless of the law that might be applied under principles of conflicts of laws.

[***]Section III.8[***]Conformity to Securities Laws[***]. Participant acknowledges that the Plan, the Grant Notice and this Agreement, are intended to conform to the extent necessary with all Applicable Laws, including, without limitation, the provisions of the Securities Act and the Exchange Act, the ITO, and any and all regulations and rules promulgated thereunder by the Securities and Exchange Commission, and state securities laws and regulations. Notwithstanding anything herein to the contrary, the Plan shall be administered, and the RSUs are granted, only in such a manner as to conform to Applicable Law. To the extent permitted by Applicable Law, the Plan, the Grant Notice and this Agreement, shall be deemed amended to the extent necessary to conform to Applicable Law.

[***]Section III.9[***]Amendment, Suspension and Termination[***]. To the extent permitted by the Plan, this Agreement may be wholly or partially amended or otherwise modified, suspended or terminated at any time or from time to time by the Administrator or the Board[***], provided[***] that, except as may otherwise be provided by the Plan, no amendment, modification, suspension or termination of this Agreement shall adversely affect the RSUs in any material way without the prior written consent of Participant.

[***]Section III.10[***]Successors and Assigns[***]. The Company may assign any of its rights under this Agreement to single or multiple assignees, and this Agreement shall inure to the benefit of the successors and assigns of the Company. Subject to the restrictions on transfer set forth in [***]Section 4.2[***] and the Plan, this Agreement shall be binding upon and inure to the benefit of the heirs, legatees, legal representatives, successors and assigns of the parties hereto.

[***]Section III.11[***]Additional Residencies and Citizenships. [***]If the Participant is a citizen or resident of a country other than the one in which the Participant is currently residing and/or working, transfers residency and/or employment after the RSUs are granted, or is considered a resident of another country for local law purposes, the Company shall, in its discretion, determine to what extent the terms and conditions contained herein shall be applicable to the Participant.

[***]Section III.12[***]No Other Rights[***]. Participant hereby acknowledges that participation in the Plan is voluntary. The value of the RSUs is an extraordinary item of compensation outside the scope of Participant’s normal compensation rights, if any. As such, the RSUs is not part of normal or expected compensation for purposes of calculating any payments due to severance, resignation, redundancy, end of service, bonuses, long-service awards, pensions or retirement benefits or similar payments. The Plan is discretionary in nature and may be amended, cancelled, or terminated by the Company, in its sole

[***]discretion, at any time. The grant of the RSUs under the Plan is a one-time benefit and does not create any contractual or other right to receive any other grant of the RSUs or other Awards under the Plan in the future. Future grants, if any, will be at the sole discretion of the Company, including, but not limited to, the timing of the grant, the form of the Award, number of Shares subject to an Award, vesting, and exercise or settlement provisions, as relevant.

[***]Section III.13[***]Not a Contract of Employment[***]. Nothing in this Agreement or in the Plan shall confer upon Participant any right to continue to serve as an employee or other service provider of any Participating Company or shall interfere with or restrict in any way the rights of any Participating Company, which rights are hereby expressly reserved, to discharge or terminate the services of Participant at any time for any reason whatsoever, with or without cause, except to the extent (i) expressly provided otherwise in a written agreement between a Participating Company and Participant or (ii) where such provisions are not consistent with applicable foreign or local laws, in which case such applicable foreign or local laws shall control.

[***]Section III.14[***]Entire Agreement[***]. The Plan (including the IL Appendix), the Grant Notice and this Agreement (including any exhibit hereto) constitute the entire agreement of the parties and supersede in their entirety all prior undertakings and agreements of the Company and Participant with respect to the subject matter hereof.

[***]Section III.15[***]Data Privacy and Consent.[***] By accepting the RSUs, the Participant is agreeing to the collection, use and transfer, in electronic or other form, of his/her applicable personal data, by and among the Company, any Participating Company, and the Trustee for the exclusive purpose of implementing, administering and managing his/her participation in the Plan.[***] [***]

[***]Section III.16[***]Agreement Severable[***]. In the event that any provision of the Grant Notice or this Agreement is held invalid or unenforceable, such provision will be severable from, and such invalidity or unenforceability will not be construed to have any effect on, the remaining provisions of the Grant Notice or this Agreement.

[***]Section III.17[***]Limitation on Participant’s Rights[***]. Participation in the Plan confers no rights or interests other than as herein provided. This Agreement creates only a contractual obligation on the part of the Company as to amounts payable and shall not be construed as creating a trust. Neither the Plan nor any underlying program, in and of itself, has any assets. Participant shall have only the rights of a general unsecured creditor of the Company with respect to amounts credited and benefits payable, if any, with respect to the RSUs.

[***]Section III.18[***]Counterparts[***]. The Grant Notice may be executed in one or more counterparts, including by way of any electronic signature, subject to Applicable Law, each of which shall be deemed an original and all of which together shall constitute one instrument.

[***]* * *

[***][***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential.

[***]ADDENDUM NO. 2

[***]to the

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***]Effective: July 1, 2020

[***](the “Contract”)

[***]issued to

[***]LEMONADE INSURANCE COMPANY

[***]New York, New York

[***]and

[***]LEMONADE INSURANCE N.V.

[***]Amsterdam, Netherlands

[***]including any and/or all companies that are or may hereafter become affiliated therewith

[***](collectively[***] [***]the “Company”)

[***]by

[***]THE SUBSCRIBING REINSURER(S) IDENTIFIED

[***]IN THE INTERESTS AND LIABILITIES AGREEMENT(S)

[***]ATTACHED TO AND FORMING PART OF THE CONTRACT

[***](the “Reinsurer”)

[***]Effective 12:01 a.m., Standard Time, July 1, 2021, with respect to losses occurring on policies attaching on or after that time and date, the following shall apply:

[***]1.    Article 1 – Business Covered – is amended to read:

[***]This Contract is to indemnify the Company in respect of the liability that may accrue to the Company as a result of loss or losses under all Policies written or renewed by the Company during the term of this Contract and classified by the Company as personal property insurance, personal liability insurance, including but not limited to auto insurance, and pet insurance, subject to the terms and conditions herein contained.

[***]2.    Paragraph A. of Article 12 – Ceding Commission – is amended to read:

[***][***]

[***]3.    The final paragraph under paragraph C.3. of Article 12 – Ceding Commission – is amended to read:

[***][***]

[***]4.    The following Paragraph D. is added to Article 12 – Ceding Commission – and all remaining paragraphs are re-alphabetized accordingly:

[***][***]

[***]5.    Paragraph G. of Article 16 – Definitions – is added:

[***][***]

[***]6.    Article 19 – Inuring Reinsurance – is amended to read:

[***]A.    Recoveries under all reinsurance contracts of the Company, whether collected or not, shall inure to the full benefit of this cover. All reinsurance contracts of the Company shall be deemed to be in place until all liability herein is finalized. Material change in inuring reinsurance is subject to mutual agreement by the Reinsurer and the Company.

[***]B.    It is hereby noted that the Company’s inuring Property Catastrophe Excess of Loss Reinsurance Agreement (U84F000B), effective 12:01 a.m., Standard Time, July 1, 2021 through 12:01 a.m., Standard Time, July 1, 2022, shall inure to the benefit of this Contract on a losses occurring basis.

[***]All other terms and conditions of the Contract shall remain unchanged.

[***]IN WITNESS WHEREOF, the Company has caused this Addendum to be executed by its duly authorized representative(s)

[***]Signed in ___[***]Israel[***]________ this __[***]29[***]__day of ______[***]July[***]_______, in the year of 20[***]21[***]__.

[***]LEMONADE INSURANCE COMPANY

[***]By: /s/ Daniel Schreiber    Title: President/CEO

[***]and signed in ____[***]Israel[***]_______ this __[***]29[***]___day of ____[***]July[***]________, in the year of 20[***]21_[***]_.

[***]LEMONADE INSURANCE N.V.

[***]By: [***] /s/ Daniel Schreiber    Title: CEO    

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***][***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential.

[***]ADDENDUM NO. 2

[***]to the

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***]Effective: July 1, 2020

[***](the “Contract”)

[***]issued to

[***]LEMONADE INSURANCE COMPANY

[***]New York, New York

[***]and

[***]LEMONADE INSURANCE N.V.

[***]Amsterdam, Netherlands

[***]including any and/or all companies that are or may hereafter become affiliated therewith

[***](collectively[***] [***]the “Company”)

[***]by

[***]THE SUBSCRIBING REINSURER(S) IDENTIFIED

[***]IN THE INTERESTS AND LIABILITIES AGREEMENT(S)

[***]ATTACHED TO AND FORMING PART OF THE CONTRACT

[***](the “Reinsurer”)

[***]Effective 12:01 a.m., Standard Time, July 1, 2021, the Subscribing Reinsurer’s participation shall be extended for an additional 12 months, and shall expire at 12:01 a.m., Standard Time, July 1, 2022. In consideration thereof, the Contract is amended as follows:

[***]1.    Article 1 – Business Covered – is amended to read:

[***]This Contract is to indemnify the Company in respect of the liability that may accrue to the Company as a result of loss or losses under all Policies written or renewed by the Company during the term of this Contract and classified by the Company as personal property insurance, personal liability insurance, including but not limited to auto insurance, and pet insurance, subject to the terms and conditions herein contained.

[***]2.    Paragraph A. of Article 4 – Term – is amended to read:

[***]A.    This Contract shall take effect at 12:01 a.m., Standard Time, July 1, 2020, and shall remain in effect until 12:01 a.m., Standard Time, July 1, 2022, in respect of losses occurring on Policies written or renewed during the term of this Contract. “Standard Time” shall be as defined in the Company’s Policies.

[***]3.    Article 11 – Ceding Commission is amended to read:

[***]A.    [***]

[***]B.    1.    Within 45 days following the end of each Contract Year hereunder, and annually thereafter until all losses allocated to each Contract Year are settled, a cumulative profit commission shall be prepared by the Company in accordance with the following, and a profit commission, if any, paid to the Company by the Reinsurer.

[***]a.    “Income” means the Reinsurer’s cumulative earned premium for the term of this Contract.

[***]b.    “Outgo” means the sum of:

[***]i.    Losses and Loss Expense paid by the Reinsurer on losses allocated to the term of this Contract, plus

[***]ii.    The outstanding case reserves of the Reinsurer on losses allocated to the term of this Contract, plus

[***]iii.    Ceding commission on Income, plus

[***]iv.    The Reinsurer’s expense allowance of [***] of Income.

[***]2.    The profit commission shall be [***] of the amount by which Income exceeds Outgo.

[***]C.    Within 45 days after the end of each Contract Year, a profit commission calculation shall be prepared by the Company, based on cumulative transactions hereunder from the inception of this Contract through the date of calculation. Any profit commission shown to be due the Company shall be paid by the Reinsurer as promptly as possible after receipt and verification of the Company’s report. The profit commission shall be adjusted annually thereafter until all losses allocated to the term of this Contract are settled. For the avoidance of doubt, each Contract Year profit commission calculation shall offset for profit commission paid to the Company by the Reinsurer in prior Contract Year periods, where applicable.

[***]4.    Paragraph E. of Article 13 – Definitions – is added to read:

[***]E.    “Contract Year” means each 12-month period from 12:01 a.m., Standard Time, July 1, to 12:01 a.m., Standard Time, July 1, during the term of this Contract. “Contract Year” is further defined as follows:

[***]1.    First Contract Year: the period from 12:01 a.m., Standard Time, July 1, 2020, to 12:01 a.m., Standard Time, July 1, 2021.

[***]2.    Second Contract Year: the period from 12:01 a.m., Standard Time, July 1, 2021, to 12:01 a.m., Standard Time, July 1, 2022.

[***]If this Contract is terminated, however, the Final Contract Year shall be from the beginning of the then current Contract Year through the date of termination.

[***]5.    Paragraph C. of Article 15 – Net Retained Liability – is added:

[***]C.    It is hereby noted that the Company’s inuring Property Catastrophe Excess of Loss Reinsurance Agreement (U84F000B), effective 12:01 a.m., Standard Time, July 1, 2021 through 12:01 a.m., Standard Time, July 1, 2022, shall inure only to the benefit of the Company.

[***]All other terms and conditions of the Contract shall remain unchanged.

[***]IN WITNESS WHEREOF, the Company has caused this Addendum to be executed by its duly authorized representative(s)

[***]Signed in [***]______Israel__[***]_____ this __[***]29_[***]_day of _____[***]July[***]________, in the year of 20[***]21[***]_.

[***]LEMONADE INSURANCE COMPANY

[***]By: /s/ Daniel Schreiber    Title: President/CEO

[***]and signed in ___[***]_Israel[***]________ this __[***]29[***]__day of _____[***]July[***]_______, in the year of 20[***]21[***]___.

[***]LEMONADE INSURANCE N.V.

[***]By: [***]/s/ Daniel Schreiber    Title: CEO    

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***][***] Certain information in this document has been excluded pursuant to Regulation S-K, Item (601)(b)(10). Such excluded information is both not material and is the type that the registrant treats as private or confidential.

[***]ADDENDUM NO. 2

[***]to the

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***]Effective: July 1, 2020

[***](the “Contract”)

[***]issued to

[***]LEMONADE INSURANCE COMPANY

[***]New York, New York

[***]and

[***]LEMONADE INSURANCE N.V.

[***]Amsterdam, Netherlands

[***]including any and/or all companies that are or may hereafter become affiliated therewith

[***](collectively[***] [***]the “Company”)

[***]by

[***]THE SUBSCRIBING REINSURER(S) IDENTIFIED

[***]IN THE INTERESTS AND LIABILITIES AGREEMENT(S)

[***]ATTACHED TO AND FORMING PART OF THE CONTRACT

[***](the “Reinsurer”)

[***]Effective 12:01 a.m., Standard Time, July 1, 2021, with respect to losses occurring after that time and date, the following shall apply:

[***]1.    Article 1 – Business Covered – is amended to read:

[***]This Contract is to indemnify the Company in respect of the liability that may accrue to the Company as a result of loss or losses under all Policies written or renewed by the Company during the term of this Contract and classified by the Company as personal property insurance, personal liability insurance, including but not limited to auto insurance, and pet insurance, subject to the terms and conditions herein contained.

[***]2.    Paragraph P. of Article 8 – Exclusions – is added:

[***]P.    As respect business classified by the Company as auto insurance:

[***]Liability, including all loss, cost or expense associated with the following classes and/or activities and known to the Company at time of binding:

[***]1.    Motorcycles, motorized scooters, motorized bicycles, racing vehicles, all-terrain vehicles, and other off-the-road motorized vehicles.

[***]2.    Operation or use of police, fire, and emergency vehicles, including ambulances.

[***]3.    Vehicles which may be classified as “public vehicles.” For purposes of this exclusion “public vehicles” shall be defined as vehicles which are defined as Public Auto’s in the ISO Commercial Auto Manual, except for purposes of this exclusion such term shall be deemed not to include vehicles used as school or church buses.

[***]4.    Fleets of fifty or more vehicles at the inception of or last anniversary of the Company’s Policy, whichever is later. This exclusion shall not apply to business derived from automobiles assigned risk plans (including JUAs), which meets the definition of the Cover and/or Exclusions Articles.

[***]5.    Any transportation, including hauling and/or handling of any “Hazardous Waste” and/or “Hazardous Materials,” as these terms are defined or determined by the United States Environmental protection Agency (“EPA”) and/or the applicable equivalent of a State EPA of the state in which the insured is insured or domiciled and/or the location of the loss. This exclusion shall not be interpreted to apply to a personal auto insured who may incidentally transport motor oil, petroleum, and/or gasoline products for personal use.

[***]6.    Vehicles used in or while practice or preparation for, a prearranged racing, speed exhibition or demolition contest.

[***]7.    Airport service vehicles.

[***]8.    Vehicles used on parts of airport premises to which the public does not have free vehicular access.

[***]In the event the Company is inadvertently bound on any exclusion enumerated under this paragraph P, the reinsurance provided under this Contract shall apply until discovery by the Company of the existence of the inadvertent binding and for 30 days thereafter, and shall then cease unless, within the 30 day period, the Company has received from the Reinsurer written notice of its approval of such binding.

[***]3.    Paragraph A. of Article 11 – Ceding Commission – is amended to read:

[***]A.    [***]

[***]4.    The following Paragraph B. is added to Article 11 – Ceding Commission – and all remaining paragraphs are re-alphabetized accordingly:

[***]B.    [***]

[***]5.    Paragraph F. of Article 13 – Definitions – is added:

[***]F.    [***]

[***]6.    Paragraph C. of Article 15 – Net Retained Liability – is added:

[***]C.    It is hereby noted that the Company’s inuring Property Catastrophe Excess of Loss Reinsurance Agreement (U84F000B), effective 12:01 a.m., Standard Time, July 1, 2021 through 12:01 a.m., Standard Time, July 1, 2022, shall inure to the benefit of this Contract on a losses occurring basis.

[***]All other terms and conditions of the Contract shall remain unchanged.

[***]IN WITNESS WHEREOF, the Company has caused this Addendum to be executed by its duly authorized representative(s)

[***]Signed in ____[***]Israel[***]________ this __[***]29[***]__day of ____[***]July[***]_________, in the year of 20[***]21[***]____.

[***]LEMONADE INSURANCE COMPANY

[***]By: /s/ Daniel Schreiber    Title: President/CEO

[***]and signed in ___[***]Israel[***]_________ this _[***]29[***]___day of ____[***]July[***]________, in the year of 20[***]21[***]__.

[***]LEMONADE INSURANCE N.V.

[***]By: /s/ Daniel Schreiber    Title: CEO

[***]WHOLE ACCOUNT QUOTA SHARE REINSURANCE CONTRACT

[***]Exhibit 31.1

[***]CERTIFICATION

[***]I, Daniel Schreiber, certify that:

[***]1.[***]I have reviewed this Quarterly Report on Form 10-Q of Lemonade, Inc.;

[***]2.[***]Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

[***]3.[***]Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

[***]4.[***]The registrant’s other certifying officers and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the registrant and have:

[***](a)[***]Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

[***](b)[***][omitted];

[***](c)[***]Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

[***](d)[***]Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

[***]5.[***]The registrant’s other certifying officers and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

[***](a)[***]All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

[***](b)[***]Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

[***]Date: August 11, 2021 [***]By: [***]/s/ Daniel Schreiber
[***]Daniel Schreiber

[***]Co-Chief Executive Officer

[***](principal executive officer)

[***]Exhibit 31.2

[***]CERTIFICATION

[***]I, Shai Wininger, certify that:

[***]1.[***]I have reviewed this Quarterly Report on Form 10-Q of Lemonade, Inc.;

[***]2.[***]Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

[***]3.[***]Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

[***]4.[***]The registrant’s other certifying officers and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the registrant and have:

[***](a)[***]Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

[***](b)[***][omitted];

[***](c)[***]Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

[***](d)[***]Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

[***]5.[***]The registrant’s other certifying officers and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

[***](a)[***]All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

[***](b)[***]Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

[***]Date: August 11, 2021 [***]By: [***]/s/ Shai Wininger
[***]Shai Wininger

[***]Co-Chief Executive Officer

[***](principal executive officer)

[***]Exhibit 31.3

[***]CERTIFICATION

[***]I, Tim Bixby, certify that:

[***]1.[***]I have reviewed this Quarterly Report on Form 10-Q of Lemonade, Inc.;

[***]2.[***]Based on my knowledge, this report does not contain any untrue statement of a material fact or omit to state a material fact necessary to make the statements made, in light of the circumstances under which such statements were made, not misleading with respect to the period covered by this report;

[***]3.[***]Based on my knowledge, the financial statements, and other financial information included in this report, fairly present in all material respects the financial condition, results of operations and cash flows of the registrant as of, and for, the periods presented in this report;

[***]4.[***]The registrant’s other certifying officers and I are responsible for establishing and maintaining disclosure controls and procedures (as defined in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the registrant and have:

[***](a)[***]Designed such disclosure controls and procedures, or caused such disclosure controls and procedures to be designed under our supervision, to ensure that material information relating to the registrant, including its consolidated subsidiaries, is made known to us by others within those entities, particularly during the period in which this report is being prepared;

[***](b)[***][omitted];

[***](c)[***]Evaluated the effectiveness of the registrant’s disclosure controls and procedures and presented in this report our conclusions about the effectiveness of the disclosure controls and procedures, as of the end of the period covered by this report based on such evaluation; and

[***](d)[***]Disclosed in this report any change in the registrant’s internal control over financial reporting that occurred during the registrant’s most recent fiscal quarter (the registrant’s fourth fiscal quarter in the case of an annual report) that has materially affected, or is reasonably likely to materially affect, the registrant’s internal control over financial reporting; and

[***]5.[***]The registrant’s other certifying officers and I have disclosed, based on our most recent evaluation of internal control over financial reporting, to the registrant’s auditors and the audit committee of the registrant’s board of directors (or persons performing the equivalent functions):

[***](a)[***]All significant deficiencies and material weaknesses in the design or operation of internal control over financial reporting which are reasonably likely to adversely affect the registrant’s ability to record, process, summarize and report financial information; and

[***](b)[***]Any fraud, whether or not material, that involves management or other employees who have a significant role in the registrant’s internal control over financial reporting.

[***]Date: August 11, 2021 [***]By: [***]/s/ Tim Bixby
[***]Tim Bixby

[***]Chief Financial Officer

[***]([***]principal financial officer[***])

[***]Exhibit 32.1

[***]CERTIFICATION PURSUANT TO

[***]18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO

[***]SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

[***]In connection with the Quarterly Report on Form 10-Q of Lemonade, Inc. (the “Company”) for the period ended June 30, 2021, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Daniel Schreiber, Co-Chief Executive Officer of the Company, certify, pursuant to 18 U.S.C. § 1350, as adopted pursuant to § 906 of the Sarbanes-Oxley Act of 2002, that, to my knowledge:

[***]1.    The Report fully complies with the requirements of section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

[***]2.    The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

[***]Date: August 11, 2021 [***]By: [***]/s/ Daniel Schreiber
[***]Daniel Schreiber

[***]Co-Chief Executive Officer

[***]([***]principal executive officer[***])

[***]Exhibit 32.2

[***]CERTIFICATION PURSUANT TO

[***]18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO

[***]SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

[***]In connection with the Quarterly Report on Form 10-Q of Lemonade, Inc. (the “Company”) for the period ended June 30, 2021, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Shai Wininger, Co-Chief Executive Officer of the Company, certify, pursuant to 18 U.S.C. § 1350, as adopted pursuant to § 906 of the Sarbanes-Oxley Act of 2002, that, to my knowledge:

[***]1.    The Report fully complies with the requirements of section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

[***]2.    The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

[***]Date: August 11, 2021 [***]By: [***]/s/ Shai Wininger
[***]Shai Wininger

[***]Co-Chief Executive Officer

[***]([***]principal executive officer[***])

[***]Exhibit 32.3

[***]CERTIFICATION PURSUANT TO

[***]18 U.S.C. SECTION 1350, AS ADOPTED PURSUANT TO

[***]SECTION 906 OF THE SARBANES-OXLEY ACT OF 2002

[***]In connection with the Quarterly Report on Form 10-Q of Lemonade, Inc. (the “Company”) for the period ended June 30, 2021, as filed with the Securities and Exchange Commission on the date hereof (the “Report”), I, Tim Bixby, Chief Financial Officer of the Company, certify, pursuant to 18 U.S.C. § 1350, as adopted pursuant to § 906 of the Sarbanes-Oxley Act of 2002, that, to my knowledge:

[***]1.[***]The Report fully complies with the requirements of section 13(a) or 15(d) of the Securities Exchange Act of 1934; and

[***]2.[***]The information contained in the Report fairly presents, in all material respects, the financial condition and results of operations of the Company.

[***]Date: August 11, 2021

[***]By: [***]/s/ Tim Bixby
[***]Tim Bixby

[***]Chief Financial Officer

[***]([***]principal financial officer)