Page 2 US-DOCS\119832991.1 working hours to consult with the VP Agency, Chief Growth Officer, and/or the Chief Executive Officer of the Company but will not have other day to day responsibilities. d. During the Transition Period and the Consultative...

Xxxxx Xxxxx [***] [***] Re: Separation Agreement Dear Yuval: This letter confirms the agreement (“Agreement”) between you and Hippo Employee Services Inc. (the “Company”) and/or any of its affiliates concerning the terms of your separation from the Company and its affiliates, and offers you the separation compensation we discussed in exchange for a general release of claims and covenant not to sue. This letter confirms the agreement (“Agreement”) between you and Hippo Employee Services Inc., a subsidiary of Hippo Holdings Inc. (“Hippo,” together with all of its affiliates, including Hippo Employee Services, the “Company”) concerning your separation from employment and the Company’s offer to you of separation benefits. 1. Separation Date; Transition Period; Consultative Period: a. Your last date of employment with the Company will be the earlier of (i) March 1, 2025; (ii) the date the Company releases you from employment for “cause”; or (iii) the date you resign employment (the “Separation Date”). “Cause” for purposes of this Agreement means a determination by the Company in its sole discretion that you have failed to materially comply with your obligations set out in Section 2 below, otherwise have violated any Company policy, otherwise have violated your obligations under the Proprietary Information and Invention Assignment Agreement (the “PIIAA”) or the Employee Invention Assignment and Confidentiality Agreement (the “EIACA”), which is attached as Exhibit A, or otherwise have engaged in misconduct. b. The period from the date you first received this Agreement through October 11, 2024, is the “Transition Period”. During the Transition Period through October 11, 2024 you will provide the orderly transition of your duties and ongoing projects to others and such other support as requested by the Chief Executive Officer of the Company. The Company expects that on or before October 8,2024, all your direct reports will be transferred to new managers, and you will not be responsible for the oversight of any other employee’s work or supervision of such work after such date. As a result, I hereby resign all officer titles with the Company or any of its affiliates effective as of October 11, 2025. c. For the period from the end of the Transition Period through the Separation Date (such period the “Consultative Period”), you agree to be reasonably available during normal Exhibit 10.1

Page 3 US-DOCS\119832991.1 d. If you choose to resign prior to the Separation Date, in lieu of 2(a), the Company will pay your eligible salary through the Separation Date at your current annualized salary rate of $475,000.50, 2024 bonus (if any), and commissions less applicable withholding and deductions including, but not limited to, state and federal payroll deductions. Additionally, the Company will increase the six (6) weeks and three (3) days of pay set out in 2(b), to pay for the number days from your Separation Date through March 1, 2024 plus monthly COBRA premiums, each calculated consistently with the current Separation Pay. 3. Return of Company Property: You agree that you will return to the Company no later than the Separation Date, or, if earlier, as requested by the Company, all property or data of the Company of any type whatsoever that has been in your possession or control. If you are unable to return your equipment in person or at the physical office location, the Company will provide you with a box to your home address on file and include a prepaid return envelope for you to return your company equipment via mail. On or before your Separation Date, the Company will provide you with a laptop to retain for your personal use and support the transfer of all personal files to the provided laptop. The depreciated value of the laptop provided will be reported as taxable income. You are not required to return computer peripherals such as monitors, speakers, keyboards, mouse, or power cords. Please coordinate with Xxxxx Xxxx or Xxx Xxxxxxxxx before the Separation Date to transfer any personal information you may have on the Company-issued laptop or electronic systems to the laptop that will be provided for your personal use. 4. Proprietary Information: You hereby acknowledge that you are bound by the attached Proprietary Information and Invention Assignment Agreement (Exhibit B hereto) and that as a result of your employment with the Company you have had access to the Company’s Proprietary Information (as defined in the agreement), that you will hold all Proprietary Information in strictest confidence and that you will not make use of such Proprietary Information on behalf of anyone. You further confirm that you have delivered to the Company all documents and data of any nature containing or pertaining to such Proprietary Information and that you have not taken with you any such documents or data or any reproduction thereof. 5. Effect of Separation on Equity: Any currently unvested Restricted Stock Units or Stock Options awarded to you under the Hippo Holdings Inc. 2019 Equity Incentive Plan or the 2021 Incentive Plan (the “Plan”) that have not vested as of the Separation Date will be automatically forfeited without consideration. You will have ninety (90) days after the Separation Date to exercise any vested but unexercised stock options, after which time such stock options will expire and be unexercisable. You can access information about your equity grants in Hippo’s equity platform, Shareworks. Shareworks tutorials are available here or you may contact xxxxx@xxxxx.xxx for support. You will be permitted to move vested shares to your personal brokerage account after your Separation Date. 6. General Release and Waiver of Claims: The payments and promises set forth in this Agreement are in full satisfaction of all accrued salary, vacation pay, bonus and commission pay, profit sharing, stock, stock options or other ownership interest in the Company, termination benefits or other compensation to which you may be entitled by virtue of your employment with the Company or your separation from the Company. To the fullest extent permitted by law, and in consideration of the opportunity to continue employment with full pay and benefit coverage

Page 4 US-DOCS\119832991.1 during the Transition Period and Consultative Period you hereby release and waive any other claims you may have against the Company and its owners, agents, officers, shareholders, employees, directors, attorneys, subscribers, subsidiaries, affiliates, successors and assigns (collectively “Releasees”), whether known or not known, including, without limitation, claims under any employment laws including, but not limited to, claims of unlawful discharge, breach of contract, breach of the covenant of good faith and fair dealing, fraud, violation of public policy, defamation, physical injury, emotional distress, claims for additional compensation or benefits arising out of your employment or your separation of employment, claims under Title VII of the Civil Rights Act of 1964 (Title VII), the Americans with Disabilities Act (ADA), the Family and Medical Leave Act (FMLA), the Fair Labor Standards Act (FLSA), the Equal Pay Act, the Employee Retirement Income Security Act (ERISA) (regarding unvested benefits), the Civil Rights Act of 1991, Section 1981 of U.S.C. Title 42, the Fair Credit Reporting Act (FCRA), the Worker Adjustment and Retraining Notification (WARN) Act, the California Worker Adjustment and Retraining Notification (Cal-WARN) Act, the National Labor Relations Act (NLRA), the Uniform Services Employment and Reemployment Rights Act (USERRA), the Genetic Information Nondiscrimination Act (XXXX), the Immigration Reform and Control Act (IRCA), the California Fair Employment and Housing Act (FEHA), the California Labor Code, the California Constitution, and the California Family Rights Act (CFRA), all including any amendments and their respective implementing regulations, and any other federal, state, local, or foreign law (statutory, regulatory, or otherwise) that may be legally waived and released. a. By signing below, you expressly waive any benefits of Section 1542 of the Civil Code of the State of California, which provides as follows: “A GENERAL RELEASE DOES NOT EXTEND TO CLAIMS THAT THE CREDITOR OR RELEASING PARTY DOES NOT KNOW OR SUSPECT TO EXIST IN HIS OR HER FAVOR AT THE TIME OF EXECUTING THE RELEASE AND THAT, IF KNOWN BY HIM OR HER, WOULD HAVE MATERIALLY AFFECTED HIS OR HER SETTLEMENT WITH THE DEBTOR OR RELEASED PARTY.” b. As a material inducement to Company to enter into this Agreement, you represent that you are not aware of any work-related injury, illness, or condition of any nature arising out of or related to your employment with Company. c. You agree to sign and return to XX@Xxxxx.xxx one copy of Exhibit A no earlier than the Separation Date and no later than 21 days after the Separation Date. d. This general release and waiver of claims excludes, and you do not waive, release, or discharge any right to file a civil action or complaint with, or otherwise notify, a state agency, other public prosecutor, law enforcement agency, or any court or other governmental entity alleging claims or a violation of rights under the California Fair Employment and Housing Act (FEHA), as well as (1) any right to file an administrative charge or complaint with, or testify, assist, or participate in an investigation, hearing, or proceeding conducted by, the Equal Employment Opportunity Commission, the California Department of Fair Employment and Housing, or other similar federal, state, or local administrative agencies; (2) claims that cannot be waived by law, such as claims for unemployment benefit rights and workers' compensation; (3) any indemnification rights you have against the Company; and (4) any claims that may arise after

Page 6 US-DOCS\119832991.1 a. To the fullest extent permitted by law, at no time subsequent to the execution of this Agreement will you pursue, or cause or knowingly permit the prosecution, in any state, federal or foreign court, or before any local, state, federal or foreign administrative agency, or any other tribunal, of any charge, claim or action of any kind, nature and character whatsoever, known or unknown, which you may now have, have ever had, or may in the future have against Releasees, which is based in whole or in part on any matter released by this Agreement. b. Nothing in this section shall prohibit or impair you or the Company from complying with all applicable laws, nor shall this Agreement be construed to obligate either party to commit (or aid or abet in the commission of) any unlawful act. 10. Protected Rights: You understand that nothing in this Agreement or any policy of the Company (including the Proprietary Information and Invention Assignment Agreement, the General Release and Waiver of Claims, the Covenant Not to Sue, and the Non-disparagement Obligation) is intended to or does prevent you from (i) discussing or disclosing information about unlawful acts in the workplace, such as harassment or discrimination or any other conduct that you have reason to believe is unlawful; (ii) contacting, filing a charge or complaint with, providing information to, or cooperating with any investigation or proceeding being conducted by, any federal or state law enforcement, governmental, or regulatory agency or body (such as the U.S. Department of Justice, the Securities and Exchange Commission, the Occupational Safety & Health Administration, the Equal Employment Opportunity Commission, the U.S. Department of Labor, the National Labor Relations Board, the California Department of Fair Employment and Housing, the California Labor Commissioner, or another federal or state fair employment practices agency) regarding alleged violations of law or unlawful acts in the workplace, and doing so in each case without prior authorization of or notice to the Company; (iii) challenging the enforceability of this Agreement if permitted by law; (iv) responding truthfully to inquiries by governmental or regulatory agencies or bodies; (v) giving truthful testimony or making statements under oath in response to valid legal process (such as a subpoena) in any legal or regulatory proceeding; or (vi) pursuant to 18 U.S.C. § 1833(b), disclosing a trade secret in confidence to a governmental official, directly or indirectly, or to an attorney, if the disclosure is made solely for the purpose of reporting or investigating a suspected violation of law, or if the disclosure is made in a document filed under seal in a lawsuit or other proceeding, and a party cannot be held criminally or civilly liable under any federal or state trade secret law for such a disclosure. 11. Non-disparagement: You agree you agree not to make, or authorize another to make, any statement (oral, written, or electronic) to the media, on social media, or to a “third party,” whether or not for attribution, which directly or indirectly (i) impugns the integrity, skills, competence, business, operations, products, services, management, prospects, customers, or personnel affairs of the Company or any of the other Released Parties or (ii) is otherwise disparaging of or derogatory about the Company or any of the other Released Parties. “Third party” for purposes of the preceding sentence does not include statements made to or between you and your spouse, personal attorney, or tax or financial advisors, if any, in a confidential manner or setting, if such persons have agreed to keep such information confidential. The Company agrees that it will not authorize the making of, and will instruct its senior executives not to make, any statement (oral, written, or electronic) to the media, on social media, or to a “third party,” whether or not for attribution, which directly or indirectly, impugns your integrity, skills, character, or competence.

Page 8 US-DOCS\119832991.1 16. No Admission of Liability: This Agreement is not and shall not be construed or contended by you to be an admission or evidence of any wrongdoing or liability on the part of Releasees, their representatives, heirs, executors, attorneys, agents, partners, officers, shareholders, directors, employees, subsidiaries, affiliates, divisions, successors or assigns. This Agreement shall be afforded the maximum protection allowable . 17. Complete and Voluntary Agreement: This Agreement, together with Exhibit A and Exhibit B hereto, and the Stock Option Agreements, constitute the entire agreement between you and Releasees with respect to the subject matter hereof and supersedes all prior negotiations and agreements, whether written or oral, relating to such subject matter. You acknowledge that neither Releasees nor their agents or attorneys have made any promise, representation or warranty whatsoever, either express or implied, written or oral, which is not contained in this Agreement for the purpose of inducing you to execute the Agreement, and you acknowledge that you have executed this Agreement in reliance only upon such promises, representations and warranties as are contained herein, and that you are executing this Agreement voluntarily, free of any duress or coercion. 18. Severability: The provisions of this Agreement are severable, and if any part of it is found to be invalid or unenforceable, the other parts shall remain fully valid and enforceable. Specifically, should a court, arbitrator, or government agency conclude that a particular claim may not be released as a matter of law, it is the intention of the parties that the general release, the waiver of unknown claims and the covenant not to sue above shall otherwise remain effective to release any and all other claims. 19. Modification; Counterparts; Facsimile/PDF Signatures: It is expressly agreed that this Agreement may not be altered, amended, modified, or otherwise changed in any respect except by another written agreement that specifically refers to this Agreement, executed by authorized representatives of each of the parties to this Agreement. This Agreement may be executed in any number of counterparts, each of which shall constitute an original and all of which together shall constitute one and the same instrument. Execution of a facsimile or PDF copy shall have the same force and effect as execution of an original, and a copy of a signature will be admissible in any legal proceeding as if an original. 20. Review of Separation Agreement; Expiration of Offer: You understand that you may take up to twenty-one (21) days to consider this Agreement (the “Consideration Period”). The offer set forth in this Agreement, if not accepted by you before the end of the Consideration Period, will automatically expire. By signing below, you affirm that you were advised to consult with an attorney prior to signing this Agreement. 21. Effective Date: This Agreement will not become effective until the eighth (8th) day after you sign, without revoking, this Agreement (the “Effective Date”). 22. Governing Law: This Agreement shall be governed by and construed in accordance with the laws of the State of California. If you agree to abide by the terms outlined in this Agreement, please sign and return it to me. I wish you the best in your future endeavors.

Page 9 US-DOCS\119832991.1 Sincerely, Hippo Employee Services Inc. By: ___________________________ Xxxxxxx XxXxxxxxx President and Chief Executive Officer READ, UNDERSTOOD, AND AGREED ________________________________ Name: Xxxxx Xxxxx Date Signed: __________________ /s/ Xxxxxxx XxXxxxxxx /s/ Xxxxx Xxxxx

US-DOCS\119832991.1 EXHIBIT A RENEWAL AND RATIFICATION OF GENERAL RELEASE AND WAIVER OF CLAIMS Do not sign before the Separation Date and no later than 21 days after the Separation Date. Upon signature, return a copy immediately to XX@Xxxxx.xxx. 1. I previously executed a Terms of Separation (“Agreement”) with Hippo Employee Services Inc. (“Company”), which is incorporated herein by reference and a Proprietary Information and Invention Assignment Agreement (“Proprietary Information Agreement”). Section 7 of the Agreement contains a General Release. 2. In exchange of my continued employment through the Separation Date, the Severance Payment, and the other promises and undertakings of the Company set out in the Agreement, I hereby renew and ratify my General Release and waiver of Claims under Section 7 of the Agreement as well as all other terms of the Agreement. I acknowledge that I am advised by this section to consult with an attorney before signing this Renewal and Ratification of General Release and Waiver of Claims. 3. This Renewal and Ratification of General Release will become effective and enforceable on the day I sign and return it to the Company. AGREED: _________________________________ Name ________________________ Date Signed

US-DOCS\119832991.1 EXHIBIT B PROPRIETARY INFORMATION AND INVENTION ASSIGNMENT AGREEMENT

4. PROPRIETARY INFORMATION AND INVENTIONS ASSIGNMENT AGREEMENT In consideration of my employment or continued employment by HIPPO ANALYTICS, INC., its subsidiaries, parent, affiliates, successors and assigns (together, the “Company”), and the compensation now and later paid to me, I agree to the terms of this Agreement as follows: 1. PROPRIETARY INFORMATION PROTECTIONS. 1.1 Nondisclosure; Recognition of Company’s Rights. I understand and acknowledge that my employment by the Company creates a relationship of confidence and trust with respect to the Company’s Proprietary Information (as defined below) and that the Company has a protectable interest in such Proprietary Information. At all times during and after my employment, I will hold in confidence and will not disclose, use, lecture upon, or publish any of Company’s Proprietary Information, except as may be required in connection with my work for Company, or as expressly authorized by a duly authorized officer of Company. I will obtain the Company’s written approval before publishing or submitting for publication any material (written, oral, or otherwise) that relates to my work at Company and/or incorporates any Proprietary Information. I hereby assign to Company any rights I may have or acquire in any and all Proprietary Information and recognize that all Proprietary Information shall be the sole and exclusive property of Company and its assigns. 1.2 Proprietary Information. The term “Proprietary Information” shall mean any and all confidential knowledge, data or information related to Company’s business or its actual or demonstrably anticipated research or development, including without limitation (a) trade secrets, inventions, ideas, processes, computer source and object code, data, formulae, programs, other works of authorship, know-how, improvements, discoveries, developments, designs, and techniques; (b) information regarding products, services, plans for research and development, marketing and business plans, budgets, financial statements, contracts, prices, suppliers, and customers; (c) information regarding the skills and compensation of Company’s employees, contractors, and any other service providers of Company; and (d) the existence of any business discussions, negotiations, or agreements between Company and any third party. 1.3 Third Party Information. I understand that Company has received and in the future will receive from third parties confidential or proprietary information (“Third Party Information”) subject to a duty on Company’s part to maintain the confidentiality of such information and to use it only for certain limited purposes. During and after the term of my employment, I will hold Third Party Information in strict confidence and will not disclose to anyone (other than Company personnel who need to know such information in connection with their work for Company) or use, Third Party Information, except in connection with my work for Company or unless expressly authorized by an officer of Company in writing. 1.4 No Improper Use of Information of Prior Employers and Others. I represent that my employment by Company does not and will not breach any agreement with any former employer, including any noncompete agreement or any agreement to keep in confidence or refrain from using information acquired by me prior to my employment by Company. I further represent that I have not entered into, and will not enter into, any agreement, either written or oral, in conflict with my obligations under this Agreement. During my employment by Company, I will not improperly make use of, or disclose, any information or trade secrets of any former employer or other third party, nor will I bring onto the premises of Company or use any unpublished documents or any property belonging to any former employer or other third party, in violation of any lawful agreements with that former employer or third party. I will use in the performance of my duties only information that is generally known and used by persons with training and experience comparable to my own, is common knowledge in the industry or otherwise legally in the public domain, or is otherwise provided or developed by Company. 2. INVENTIONS. 2.1 Definitions. As used in this Agreement, the term “Invention” means any ideas, concepts, information, materials, processes, data, programs, know-how, improvements, discoveries, developments, designs, artwork, formulae, other copyrightable works, and techniques and all Intellectual Property Rights in any of the items listed above. The term “Intellectual Property Rights” means all trade secrets, copyrights, trademarks, mask work rights, patents and other intellectual property rights recognized by the laws of any jurisdiction or country. The term “Moral Rights” means all paternity, integrity, disclosure, withdrawal, special and any other similar rights recognized by the laws of any jurisdiction or country. 2.2 Prior Inventions. I have disclosed on Exhibit A a complete list of all Inventions that (a) I have, or I have caused to be, alone or jointly with others, conceived, developed, or reduced to practice prior to the commencement of my employment by Company; (b) in which I have an ownership interest or which I have a license to use; (c) and that I wish to have excluded from the scope of this Agreement (collectively referred to as “Prior Inventions”). If no Prior Inventions are listed in Exhibit A, I warrant that there are no Prior Inventions. I agree that I will not incorporate, or permit to be incorporated, Prior Inventions in any Company Inventions (defined below) without Company’s prior written consent. If, in the course of my employment with Company, I incorporate a Prior Invention into a Company process, machine or other work, I hereby grant Company a non-exclusive, perpetual, fully-paid and royalty-

7 This Agreement shall be effective as of the first day of my employment with Company. EMPLOYEE: I HAVE READ, UNDERSTAND, AND ACCEPT THIS AGREEMENT AND HAVE BEEN GIVEN THE OPPORTUNITY TO REVIEW IT WITH INDEPENDENT LEGAL COUNSEL. (Signature) By: ______________________ Date: _____________________________________________ COMPANY: ACCEPTED AND AGREED: (Signature) By: Assaf Wand Title: CEO Date: _________________ Address: 000 Xxxxxx Xxxxxx, Xxxxxxxx Xxxx XX 00000 12 / 17 / 2017 Yuval Xxxxx 12 / 19 / 2017 Address: [***] /s/ Xxxxx Xxxxx /s/ Xxxxx Xxxx