#1Proprietary and Confidential | 1#2Disclaimer (1/2) About this Presentation This presentation ("Presentation") is for informational purposes only. This Presentation shall not constitute an offer to sell, or the solicitation of an offer to buy, any securities, nor shall there be any sale of securities in any states or jurisdictions in which such offer, solicitation or sale would be unlawful. This Presentation has been prepared to assist interested parties in making their own evaluation with respect to a potential business combination between Hippo Enterprises, Inc. ("Hippo") and Reinvent Technology Partners Z ("Reinvent") and the related transactions (the "Proposed Business Combination") and for no other purpose. Neither the Securities and Exchange Commission nor any securities commission of any other U.S. or non-U.S. jurisdiction has approved or disapproved of the Proposed Business Combination presented herein, or determined that this Presentation is truthful or complete. No representations or warranties, express or implied are given in, or in respect of, this Presentation. To the fullest extent permitted by law in no circumstances will Hippo, Reinvent or any of their respective subsidiaries, stockholders, affiliates, representatives, directors, officers, employees, advisers, or agents by responsible or liable for a direct, indirect, or consequential loss or loss of profit arising from the use of this Presentation its contents, its omissions, reliance on the information contained within it, or on opinions communicated in relation thereto or otherwise arising in connection therewith. Industry and market data used in this Presentation have been obtained from third-party industry publications and sources as well as from research reports prepared for other purposes. Neither Hippo nor Reinvent has independently verified the data obtained from these sources and cannot assure you of the data's accuracy or completeness. This data is subject to change. In addition, this Presentation does not purport to be all-inclusive or to contain all of the information that may be required to make a full analysis of Hippo or the Proposed Business Combination. Viewers of this Presentation should each make their own evaluation of Hippo and of the relevance and adequacy of the information and should make such other investigations as they deem necessary. Forward Looking Statements Certain statements included in this Presentation that are not historical facts are forward-looking statements for purposes of the safe harbor provisions under the United States Private Securities Litigation Reform Act of 1995. Forward-looking statements generally are accompanied by words such as "believe," "may," "will," "estimate," "continue," "anticipate,” “intend," "expect," "should," "would," "plan," "predict," "potential," "seem," "seek," "future," "outlook," and similar expressions that predict or indicate future events or trends or that are not statements of historical matters. These forward-looking statements include, but are not limited to, statements regarding estimates and forecasts of other financial and performance metrics and projections of market opportunity. These statements are based on various assumptions, whether or not identified in this Presentation, and on the current expectations of the respective management of Hippo and Reinvent and are not predictions of actual performance. These forward-looking statements are provided for illustrative purposes only and are not intended to serve as, and must not be relied on by an investor as, a guarantee, an assurance, a prediction, or a definitive statement of fact or probability. Actual events and circumstances are difficult or impossible to predict and will differ from assumptions. Many actual events and circumstances are beyond the control of Hippo and Reinvent. These forward-looking statements are subject to a number of risks and uncertainties, including changes in domestic and foreign business, market, financial, political, and legal conditions; natural or man-made catastrophes such as hurricanes, typhoons, earthquakes, floods, climate change (including effects on weather patterns; greenhouse gases; sea, land and air temperatures; sea levels; and rain and snow), nuclear accidents, pandemics (including COVID-19), or terrorism; continued impact of COVID-19 and related risks; ability to collect reinsurance recoverable, credit developments of reinsurers, and any delays with respect thereto and changes in the cost, quality, or availability of reinsurance; effects of data privacy or cyber laws or regulation; actual amount of new and renewal business, market acceptance of products, and risks associated with the introduction of new products and services and entering new markets; ability to increase use of data analytics and technology as part of business strategy; ability to attract, retain, and expand customer base; ability to compete effectively in the industry; effects of seasonal trends on results of operations; the inability of the parties to successfully or timely consummate the Proposed Business Combination, including the risk that any regulatory approvals are not obtained, are delayed or are subject to unanticipated conditions that could adversely affect the combined company or the expected benefits of the Proposed Business Combination or that the approval of the stockholders of Hippo or Reinvent is not obtained; failure to realize the anticipated benefits of the Proposed Business Combination; risks relating to the uncertainty of the projected financial information with respect to Hippo; risks related to the performance of Hippo's business and the timing of expected business or revenue milestones; the effects of competition on Hippo's business; the amount of redemption requests made by Reinvent's stockholders; the ability of Hippo or Reinvent to issue equity or equity-linked securities or obtain debt financing in connection with the Proposed Business Combination or in the future, and those factors discussed in Reinvent's prospectus on Form S-1 filed with the SEC on November 18, 2020 under the heading "Risk Factors," and other documents Reinvent has filed, or will file, with the SEC. If any of these risks materialize or our assumptions prove incorrect, actual results could differ materially from the results implied by these forward-looking statements. There may be additional risks that neither Hippo nor Reinvent presently know, or that Hippo nor Reinvent currently believe are immaterial, that could also cause actual results to differ from those contained in the forward-looking statements. In addition, forward-looking statements reflect Hippo's and Reinvent's expectations, plans, or forecasts of future events and views as of the date of this Presentation. Reinvent and Hippo anticipate that subsequent events and developments will cause Hippo's and Reinvent's assessments to change. However, while Hippo and Reinvent may elect to update these forward-looking statements at some point in the future, Hippo and Reinvent specifically disclaim any obligation to do so. These forward-looking statements should not be relied upon as representing Hippo's and Reinvent's assessments of any date subsequent to the date of his Presentation. Accordingly, undue reliance should not be placed upon the forward- looking statements. Use of Projections This Presentation contains projected financial information. Such projected financial information constitutes forward-looking information, and is for illustrative purposes only and should not be relied upon as necessarily being indicative of future results. The assumptions and estimates underling such financial forecast information are inherently uncertain and are subject to a wide variety of significant business, economic, competitive, and other risks and uncertainties. See "Forward-Looking Statements" above. Actual results may differ materially from the results contemplated by the financial forecast information contained in this Presentation, and the inclusion of such information in this Presentation should not be regarded as a representation by any person that the results reflected in such forecasts will be achieved. Proprietary and Confidential | 2#3Disclaimer (2/2) Use of Data The data contained herein is derived from various internal and external sources. No representation is made as to the reasonableness of the assumptions made within or the accuracy or completeness of any projections or modeling or any other information contained herein. Any data on past performance or modeling contained herein is not an indication as to future performance. Hippo and Reinvent assume no obligation to update the information in this presentation. Use of Non-GAAP Financial Metrics and Other Key Financial Metrics This presentation includes certain non-GAAP financial measures (including on a forward-looking basis) such as Adjusted Gross Profit ("AGP"), Adjusted EBITDA and Total Written Premium ("TWP"). Hippo defines Adjusted Gross Profit, a Non-GAAP metric, as Gross Profit excluding investment income, plus channel distribution cost and overhead associated with Hippo's underwriting operations including employee-related expense and professional fees, plus depreciation, amortization, stock-based compensation and other non-cash expenses associated with Hippo's cost of revenue, plus pro-forma synergy adjustments for the acquisition of Spinnaker. Hippo believes the resulting calculation is inclusive of the variable costs of revenue incurred to successfully service a policy, irrespective of the distribution channel or the underwriting insurance carrier, and is therefore a key measure of the profitability of its underlying book of business. Hippo defines Adjusted EBITDA, a Non-GAAP metric, as net loss excluding income tax expense, interest expense, depreciation, amortization, stock-based compensation, net investment income, and other non-cash adjustments such as fair value, contingent consideration and pro- forma synergy adjustments for the acquisition of Spinnaker, and other transactions that Hippo would consider to be unique in nature. Hippo excludes these items from Adjusted EBITDA because it does not consider them to be directly attributable to its underlying operating performance. Hippo defines Total Written Premium as the Gross Written Premium of policies underwritten by Hippo and its affiliates plus the premium of policies placed with third-party insurance carriers where Hippo earns a recurring commission payment. These non-GAAP measures are an addition, and not a substitute for or superior to measures of financial performance prepared in accordance with GAAP and should not be considered as an alternative to net income, operating income or any other performance measures derived in accordance with GAAP. Reconciliations of non-GAAP measures to their most directly comparable GAAP counterparts are included in the Appendix to this presentation. Hippo believes that these non-GAAP measures of financial results (including on a forward-looking basis) provide useful supplemental information to investors about Hippo. Hippo's management uses forward looking non-GAAP measures to evaluate Hippo's projected financial and operating performance. However, there are a number of limitations related to the use of these non- GAAP measures and their nearest GAAP equivalents. For example other companies may calculate non-GAAP measures differently, or may use other measures to calculate their financial performance, and therefore Hippo's non-GAAP measures may not be directly comparable to similarly titled measures of other companies. This Presentation also includes certain projections of non-GAAP financial measures. Due to the high variability and difficulty in making accurate forecasts and projections of some of the information excluded from these projected measures, together with some of the excluded information not being ascertainable or accessible, Hippo is unable to quantify certain amounts that would be required to be included in the most directly comparable GAAP financial measures without unreasonable effort. Consequently, no disclosure of estimated comparable GAAP measures is included and no reconciliation of the forward looking non-GAAP financial measures is included. Participants in Solicitation Hippo and Reinvent and their respective directors and executive officers, under SEC rules, may be deemed to be participants in the solicitation of proxies of Reinvent's shareholders in connection with the proposed business combination. Investors and security holders may obtain more detailed information regarding the names and interests in the proposed business combination of Reinvent's directors and officers in Reinvent's filings with the SEC, including Reinvent's registration statement on Form S-1, which was originally filed with the SEC on November 20, 2020. To the extent that holdings of Reinvent's securities have changed from the amounts reported in Reinvent's registration statement on Form S-1, such changes have been or will be reflected on Statements of Change in Ownership on Form 4 filed with the SEC. Information regarding the persons who may, under SEC rules, be deemed participants in the solicitation of proxies to Reinvent's shareholders in connection with the proposed business combination is set forth in the proxy statement/prospectus on Form S-4 for the proposed business combination, which is expected to be filed by Reinvent with the SEC. Investors and security holders of Reinvent and Hippo are urged to read the proxy statement/prospectus and other relevant documents that will be filed with the SEC carefully and in their entirety when they become available because they will contain important information about the proposed business combination. Investors and security holders will be able to obtain free copies of the proxy statement and other documents containing important information about Hippo and Reinvent through the website maintained by the SEC at www.sec.gov. Copies of the documents filed with the SEC by Reinvent can be obtained free of charge by visiting the SEC's website at https://www.sec.gov/cgi-bin/browse-edgar?CIK=1828105, the investor relations page of Reinvent's website at https://z.reinventtechnologypartners.com/investor- relations/sec-filings, or by directing a written request via email to [email protected] with the subject line "RTPZ SEC Filings Request." Proprietary and Confidential | 3#4Today's Presenters Reid Hoffman Co-Lead Director of RTPZ Michael Thompson President and CEO of RTPZ Assaf Wand Chief Executive Officer Richard McCathron President Reinvent Reinvent Stewart Ellis Chief Financial Officer Proprietary and Confidential | 4#5Transaction Summary Transaction Structure Hippo and Reinvent are partnering to transform the home insurance industry Founder shares are structured to create long-term alignment Valuation Transaction implies a fully diluted pro forma enterprise value of $5.0B 4.4x 2023E Total Written Premium 25.1x 2023E Adjusted Gross Profit Existing Hippo shareholders to retain ~87% of the pro forma equity Capital Structure The transaction will be funded by a combination of Reinvent cash held in a trust account and proceeds from Reinvent PIPE for an aggregate of up to $780MM Pro forma for the transaction, Hippo expects to have up to $1.2B in cash to fund growth and operations Proprietary and Confidential | 5#6Proud to Partner with Hippo Reinvent + What Attracted Us to Hippo? Adaptive Management Team Strong Unit Economics Asymmetric Risk Reward Housing Fundamentals Tech + Insurance Expertise Relative and Fundamental Valuation Disciplined Underwriters Homeowners Insurance Mkt Structure Customer Value Proposition Proprietary and Confidential | 6#7De-SPAC Structure Aligns Interests for the Long-Term Reinvent + One Board Seat Designated by Reinvent Lock-up Arrangements Up to two-years on founder shares Senior Hippo management and material existing investors subject to lock-up arrangements substantially similar to the founder shares Price-based Vesting Triggers of $12.50, $15, and $20 per share on founder shares $550M PIPE Investment Upsized from $500M with participation from Reinvent Capital Strong Alignment for Hippo & Reinvent to Drive Significant Long-Term Value for Shareholders Proprietary and Confidential | 7#8VISION Hippo exists to protect the joy of homeownership MISSION Delivering intuitive and proactive protection for homeowners, combining the power of technology with a human touch Proprietary and Confidential | 8#9THOUGH HOME INSURANCE IS A $100 B+ MARKET Legacy insurers spent 100 years building a flawed experience Top 4 Home Insurers Difficult purchase process Mkt. Share1 Founded State Farm 17.9% 1922 Outdated coverage Allstate Corp 8.4% 1931 Poor claims experience USAA 6.6% 1922 Liberty Mutual 6.5% 1912 Zero meaningful touchpoints Top-10 average age: 108 1. JMP Securities Internet & Digital Media, 2020; 2. Statistica; 3. Morgan Stanley/BCG Global Consumer Survey 2014, BCG e-intensity index 35/100 Typical Carrier NPS2 -49 for Claims3 Proprietary and Confidential | 9#10The entire system creates a transactional, adversarial relationship between insurers and customers When one wins, the other loses We believe there is a better way Proprietary and Confidential | 10#11Hippo makes insurance simple, modern, and proactive Easy to buy 1 minute to quote, 5 minutes to purchase Coverage designed for modern lives Expanded home office, electronics coverage, etc. Proactive, human approach to claims Event monitoring, claims concierge Tech-enabled, proactive partnership with customers IoT Devices, continuous underwriting, maintenance resources 1. Most recent 90-day NPS; source: Delighted LLC 75/100 Overall NPS 60 for Claims1 Proprietary and Confidential | 11#12Hippo takes a proactive approach to drive better outcomes for homeowners 1 Ongoing Underwriting 2 3 Smart Home Devices Maintenance Support Proprietary and Confidential | 12#13Ongoing underwriting Property/permit data Risk score modeling Customer history Behavioral analytics Fraud identification Risk modeling (Cat, non-Cat) Permit analysis Physical property inspections Onboarding Run risk models with initial data Day 0 Proprietary and Confidential | 13 1#14Ongoing underwriting Property/permit data Risk score modeling Customer history Fraud identification Risk modeling (Cat, non-Cat) Permit analysis Behavioral analytics Physical property inspections New pool identified! Year 1 Outreach with recommendation to increase liability coverage Proprietary and Confidential | 14 1#15Ongoing underwriting Property/permit data Risk score modeling Customer history Fraud identification Risk modeling (Cat, non-Cat) Permit analysis Behavioral analytics Physical property inspections New roof identified! Year 4 Update premium with new roof discount Proprietary and Confidential | 15 1#16Our Smart Home program is the most widely adopted in the US Home Insurance space1 hippo Smart Home Monitoring System provided by Hippo Insurance hippo This is a Smart Home Monitoring Kit Provided by Hippo & Kangaroo Keep tabs with your phone on motion, entry water leaks, temperature & humidity in your home. 15 SimulSate kangaroo 000 kangaroo Kits include devices intended to mitigate damage from water, fire and theft Included in standard policies, with premium discounts Complimentary self or professionally-monitored kits Enhancing discounts based on kit placement and behavior Drives acquisition, retention, and reduces risk over time 75% Opt-in rate² 74% Activation rate² 500K Devices shipped² Largest program of its kind¹ 1. Source: Connected Insurance Observatory, a global insurance think-tank 2. Source: Company data Proprietary and Confidential | 16 2#17We help customers maintain their homes Thousands Of home checkups delivered 4:411 < Back Caulking Condition Good Under Sink Photos 11K+ Preventive actions performed¹ 4.5 out of 5 Average customer satisfaction score¹ 1. Source: Company data Sink and Drains Leaks Under Sink? Active 1:187 ◄ Professional G Fair Ne Atte X • Recommended Services Evidence N of Prior Garbage Disposal Present? Yes Cleaned Drains? Yes Purchase Fire Extinguisher $125.00 Install Braided Washing Machine Hoses $120.00 Water Heater Service $200.00 Replace Bathroom Drain Stoppers Optional Services Earthquake Emergency Kit $100.00 No Replace Living Room Lights $109.00 No Monitoring Recommended Water Filtration System Present? Monitor Condensation in Master Bedroom Window Yes No You Requested Request(2) Services ✓ Proprietary and Confidential | 17 3#18Hippo's proactive approach turns an adversarial customer relationship into a partnership And average risk into better risk Proprietary and Confidential 18#19Insurance is a hard industry to enter Data Availability Access and integrity challenges Fragmented Regulation at the state level High Initial Capital Requirements Especially for a startup Distribution Access Requires significant tech and ops investments Proprietary and Confidential | 19#20The opportunity in homeowners insurance is potentially massive Massive $105B In Annual Premiums1 growing 5% annually Fragmented 10% Only one player with more than 10% share Attractive Dynamics +8 YRS Customer Lifetime2 annual avg. premium ~$1,200 1. Source: Morgan Stanley research 2. Source: William Blair research Proprietary and Confidential 20#21Hippo has a technological advantage over existing players Legacy tech stacks prevent meeting customer expectations VS Owning a proprietary, modern tech stack enables better adaptation to customer expectations and to partner platforms Customer- supplied data impacts underwriting accuracy Outdated pricing models due to regulatory limitations VS VS Third-party, verifiable data sources enables more accurate underwriting Next generation, granular pricing at the peril level, based on current risks and modern homes Proprietary and Confidential | 21#22Macro trends favor tech-forward challengers Aging Agent Population average age of 611 (and increasing) Agent-channel conflict Incumbents hindered by legacy agent network VS VS Birth of the digital consumer New generation of customers expect differentiated buying experiences Omni-channel distribution API integration into multiple channel partners (such as builders, originators, realtors, loan servicers) 1. Source: McKinsey & Company; Company analysis Proprietary and Confidential | 22#23Our distribution allows customers to purchase however they want and provides Hippo differentiated access to the best risk Direct to Customer Agents Partners Fast and accurate online purchase Agents can focus on the customers' insurance needs and not on form filling Tech embedded into partner sales flows enables access to positively selected customer base Proprietary and Confidential | 23#24Vertical, integrated approach to building an all-inclusive home protection platform Home Warranty Flood Insurance HOA Insurance Renters Auto Condo Homeowners Smart Home Tech Home Maintenance Professional Monitoring Travel Pet Life Umbrella Proprietary and Confidential | 24#25Financial Overview Proprietary and Confidential | 25#26Hippo's economic models 1 3 MGA Commission, Policy, and Service Fees Carrier Insurance as a Service 2 Agency Agency Commission 4 Risk Retention Earned Premium Note: "MGA" = Managing General Agent, full underwriting authority and claims administration Proprietary and Confidential | 26#27Asset-light capital strategy ~90% 1. Quota Share reinsurance and CAT Excess of Loss ~10% ~75% Reinsurance1 ~25% Net Risk Retained 2021E Long Term Proprietary and Confidential | 27#28Total Written Premium1 Highly recurring and predictable Unaffected by short-term fluctuations in loss ratio Key metrics & performance indicators Premium Renewal Rate Loss Ratio Important driver of future Total Written Premium and customer lifetime value Driver of long-term profitability Improves with cohort tenure and becomes less volatile as we scale and diversify geographically Adjusted Gross Profit Source of capital for business operations Neutralizes for carrier/channel mix and reinsurance structure 1. Total Written Premium represents the Gross Written Premium of policies underwritten by Hippo and its affiliates plus the premium of policies placed with third-party insurance carriers where Hippo earns a recurring commission payment. Proprietary and Confidential | 28#29Proven track record of growth and execution Historical Total Written Premium, $m¹ $304 $142 2018 2019 69% '18 '20 Growth 2020 Milestones Rapid Geographic Diversification 12 new state launches Vertical Integration Acquisition of Spinnaker to become full-stack carrier $405 Mitsui Sumitomo Partnership Incremental capital and a multi-year reinsurance commitment 2020 1. Spinnaker and Agency presented on a proforma basis as of 1/1/18 Validated Partnership Distribution Channels Home builders, mortgage servicers Proprietary and Confidential | 29#30Solid foundation for continued topline growth Historical & Projected Total Written Premium, $m¹ 69% '18 '20 Growth 43% '21'25 CAGR $1,145 $796 $544 $405 $304 $142 2018 2019 $1,628 2020 2021F 2022F 2023F 2024F 1. Spinnaker and Agency presented on a proforma basis as of 1/1/18 $2,279 2025F Proprietary and Confidential | 30#31Our business strengthens as we scale Improved Unit Economics, More Profits Reinvested in Growth Higher Customer Satisfaction & Retention Increased Scale Increasingly Predictable & Profitable More Data, Deeper Insights More Accurate Pricing, Better Underwriting Results Proprietary and Confidential | 31#32Our growth strategy provides a cash-efficient path to scale 1. $0 Upfront Marketing Dollars in our agent and partner channels₁ of customers pay 60% annually in advance2 1.5 Payback period of the acquisition costs³ YEARS Commission in these channels is paid on cash collected premium 2. as of January 2021 3. Expected for Q1'21 Cohorts Source: Company data Proprietary and Confidential | 32#33We have attractive customer dynamics... ...and compelling unit economics -$1,200 Avg. Premium 8+ Years Avg. Customer Life1 1. Source: William Blair research 2. Expected for Q1'21 Cohorts; calculated as the cumulative contribution margin of a policy over its expected lifetime ~$350 5.4x -$1,900 Customer Acquisition Cost (CAC) Lifetime Value² (LTV) Proprietary and Confidential | 33#34Unit economics improving over time Improving Retention Annual Premium Retention by Cohort Declining Loss Frequency 12-month average Non-CAT Frequency by Cohort¹ Yr 1 Yr 2 Yr 3 78% 87% 2017 98% New Renewal 5.2 86% 87% 82% 2018 2019 4.0 3.9 3.5 3.2 3.3 2.8 2017 2018 2019 2020 Proprietary and Confidential | 34 1. Frequency defined as number of claims divided by the total number of units of exposure, where a unit of exposure is defined as one policy year earned. For example, one policy in force written 24 months ago, represents 2x units of exposure; The cohorts are 12-month cohorts starting on 8/1 of each calendar year Source: Company data#35Path to steady state Loss Ratio Bridge from 2020 to Steady State Indicated Loss Ratio of Hippo Programs¹ 1. 2. 121% -24% -5% -9% 83% -9% -6% -4% 60% -4% 2020 Normalization Maturity 2020E Loss Ratio Excess CAT COVID Unearned Rate Changes 2020 Normalized Loss Ratio Operational Improvements Growth Penalty² Loss and Allocated Loss Adjustment Expense; refers to all policies underwritten by Hippo's MGA, whether written on our own carrier or a 3rd party carrier; preliminary estimates, subject to change Higher Earned Premium /Written Premium ratio and higher tenure maturity (higher renewal business as % of book) Differentiation Proactive / Preventative Strategy Underwriting and Claims Innovation/ Product Mix Steady State Loss Ratio Proprietary and Confidential | 35#36Enabling rapid margin expansion as we scale Projected Total Written Premium, $m 43% '21'25 CAGR $544 $796 $1,145 2021F 2022F 2023F $1,628 2024F $2,279 2025F Projected Adjusted Gross Profit, $m 92% '21'25 CAGR % of TEP1 $546 $340 28% $202 25% $106 21% $40² 16% 9% 2021F 2022F 2023F 2024F 2025F 1. Total Earned Premium; represents the earned portion of our Total Written Premium. Our insurance policies generally have a term of one year and premium is earned pro rata over the term of the policy 2. On a proforma basis; includes $4.1 million of Spinnaker deferred ceding commission income which was part of opening balance sheet adjustments as required under US GAAP Source: Company projections Proprietary and Confidential | 36#37Our target operating model All shown as a % of Total Earned Premium¹ Normalized² 2020 Projected 2025 Long-Term Gross Loss Ratio³ 83% 62% 60% Adjusted Gross Profit 10% 28% 38% Operating Income4 1. Proforma for Spinnaker and NAAIS acquisition as of 1/1/18 2. Assuming a normalized 2020 Loss Ratio as described on page 35 (22%) 3% 15% 3. Includes Losses and Allocated Loss Adjustment Expenses and assumes steady-state CAT load in 2025; refers to all policies underwritten by Hippo's MGA, whether written on our own carrier or a 3rd party carrier; preliminary estimates, subject to change 4. On a Non-GAAP basis; represents Adjusted EBITDA plus investment income Proprietary and Confidential | 37#38Proven track record of cash-efficient growth >$400M PIF1 in <4 Years 69% 2-Year TWP2 CAGR Financial Highlights In a large and attractive market Superior consumer experience driven by differentiated technology and approach $105B US Home Insurance 75 NPS vs. 35 Industry 8+ Years Customer Lifetime 60 NPS For Claims Compelling unit economics that are improving as we scale Capital-efficient path to long term profitability 1. Premium in Force 2. Total Written Premium 3. 2021-2025F; including CAT XOL 4. Adjusted Gross Profit; on a pro-forma basis Source: Morgan Stanley research, William Blair research, Delighted LLC, Company data 5.4x LTV:CAC 1.5 Yrs Payback 75-90% QS Reinsurance³ 92% '21-'25 AGP4 CAGR Proprietary and Confidential | 38#39Hippo exists to protect the joy of homeownership 1 Radically improved customer experience 2 3 Policies built for modern lives, powered by data and technology Proactive services that reinforce our core product and strengthen our relationship with customers Proprietary and Confidential | 39#40Appendix Proprietary and Confidential | 40#41Transaction Summary Key Highlights Approximately $5B enterprise value 4.4x 2023E Total Written Premium or 25.1x 2023E Adjusted Gross Profit Hippo stockholders retain ~87% in pro forma ownership Hippo receives $638M in primary proceeds to fund growth Sources Uses Cash proceeds to Hippo $638 Seller rollover equity $5,422 Equity consideration to $5,422 existing Hippo Shareholders PIPE investment $550 Cash consideration to existing Hippo shareholders $100 Reinvent cash held in trust $230 Estimated transaction costs $42 Hippo management will continue to operate the business post-closing Total sources $6,202 Total uses $6,202 Transaction expected to close in Q2 2021 1. 2. Pro forma valuation $MM, unless otherwise noted Pro forma ownership at closing Share price $10.00 4% 87% Pro forma shares outstanding¹ Pro forma equity value 621.6 SPAC public holders $6,216 Existing company shareholders Less: Pro forma net cash² Pro forma aggregate value ($1,160) $5,057 9% PIPE holders Pro forma shares outstanding based on $10.00 per share price and includes 25% of 5.75MM Reinvent shares vested at closing. Additionally, pro forma shares excludes potential dilution from out-of-the-money warrants and further assumes no redemptions by Reinvent's existing public shareholders Proprietary and Confidential | 41 Includes $522MM of existing Hippo cash and cash equivalents as of December 31, 2020 and $638MM of net proceeds to be added to Hippo's balance sheet#42Hippo: Best in class Insurtech Hippo Lemonade metromile Root Insurance Co 2023 Scale Gross Written Premium ($MM) 1,1451 778 5242 2,150 Growth ('21E - '23E CAGR) Adj. Gross Profit³ Growth Rate (%) 124% 65% 113% 179% Retention One-Year Retention (%) 87%4 62%5 63%6 33%7 Customer Profile Avg. Premium Per Policy ($) ~$1,200 $2138 $1,076⁹ $9299 Unit Economics LTV/CAC (x) 5.4x 1. 2. Represents Total Written Premium; defined as the Gross Written Premium of policies underwritten by Hippo and its affiliates plus the premium of policies placed with third-party insurance carriers where Hippo earns a recurring commission payment. Represents Direct Earned Premium 3. 4. A Non-GAAP Metric and may be defined differently for each company Represents 2019, one-year premium retention 5. As disclosed in S-1 and adjusted for company-initiated cancellations; as of March 31,2020 Source: Company estimates, subject to change; street estimates; based on latest disclosed financials and available estimates >2x8 3.1x6 N/A 6. As of June 30, 2020 7. Represents one-year retention across two terms after adjustments for company initiated cancellations, as disclosed in S-1; as of June 30, 2020 8. As disclosed in the Q4'20 earnings transcript 9. As of September 30, 2020 Proprietary and Confidential | 42#43Valuation Benchmarking AV/Gross Written Premium (2023E) 7.8x Lemonade' AV/Adj. Gross Profit (2023E) 41.8x Lemonade 1. AV pro forma for follow on offering 2. Reflects Total Written Premium multiple 4.4x 2.5x 1.0x Hippo metromile Root Insurance Co 25.1x Hippo 3. Reflects Gross Earned Premium multiple 9.1x 8.0x metromile Root Insurance Co Proprietary and Confidential | 43 Source: Company estimates, subject to change; street estimates; based on latest disclosed financials and available estimates; market data as of 3/3/2021#44Summary Consolidated Non-GAAP P&L Pro forma for Spinnaker and Agency as of 1/1/19 ($ in Millions) 2019A 2020A 2021F 2022F 2023F 2024F 2025F Total Written Premium Total Earned Premium $304 $405 $544 $796 $1,145 $1,628 $2,279 228 363 473 666 967 1,382 1,947 Revenue $49 $63 $87 $151 $282 $488 $789 Adjusted Gross Profit $40 $30 $40 $106 $202 $340 $546 % of Total Earned Premium 18% 8% 9% 16% 21% 25% 28% Operating Expenses $93 $119 $187 $241 $310 $380 $488 Operating Income ($53) ($89) ($146) ($135) ($108) ($40) $58 % of Total Earned Premium -23% -25% -31% -20% -11% -3% 3% 1. Unaudited, preliminary results, subject to change Proprietary and Confidential | 44#45Reconciliation of FY2020 Actuals to Pro forma ($ in Millions) Actuals PF Adjustment Pro forma 2020A1 Jan-Aug 2020 2020A Total Written Premium $333 $72 $405 Total Earned Premium 299 65 363 Revenue $52 $12 $63 Adjusted Gross Profit $16 $14 $30 % of Total Earned Premium 5% 22% 8% Operating Expenses Operating Income $114 $6 $119 ($98) $9 ($89) % of Total Earned Premium -33% 13% -25% 1. Unaudited, preliminary results, subject to change 2. Spinnaker acquisition closed on 8/31; Proforma view represents Spinnaker's financials 1/1-8/31 of 2020 Proprietary and Confidential | 45#46Adjusted Gross Profit - Non-GAAP Reconciliation $ in Millions Revenue Loss and Loss Adjustment Expense Insurance Related Expense GAAP Gross Profit Adjustments: Less: Net Investment Income Add: Channel Distribution Costs Add: Employee Related costs Add: Depreciation, Amortization and Other Non-Cash Expenses Adjusted Gross Profit 1. Preliminary actual results, subject to change 2. This does not include $4.9 million of Spinnaker deferred ceding commission income as it was part of opening balance sheet adjustments as required under US GAAP FY2020A1 (Unaudited) 51.5 (25.3) (19.3) 7.0 (1.1) 4.6 0.9 4.1 15.52 Proprietary and Confidential | 46#47Adjusted EBITDA - Non-GAAP Reconciliation $ in Millions FY2020A1 (Unaudited) (141.5) Net Income (Loss) Adjustments: Less: Benefit from Income Taxes Less: Capitalization of Software Development costs Add: Depreciation and Amortization Add: Stock Based Compensation Add: Fair Value Adjustments² Add: Non-Cash Interest Expense³ Add: Contingent Consideration Charge4 Add: Other One-off Transactions Non-GAAP Operating Income Less: Net Investment Income Adjusted EBITDA (1.8) (9.4) 6.7 17.7 22.4 3.5 3.4 0.8 (98.1) (1.1) (99.2)5 1. Preliminary actual results, subject to change 12345 Change in FV of preferred stock warrant liabilities and derivative on convertible note Amortization of the discount of the convertible note Change in FV of the estimated future payments for earnout This does not include $3.5 million of Spinnaker deferred ceding commission income (net of DAC) as it was part of opening balance sheet adjustments as required under US GAAP Proprietary and Confidential | 47#48Summary of Risks (1/3) Investing in our common stock involves a high degree of risk. You should carefully consider the following risks, together with all of the other information contained in this prospectus, before deciding to invest in our common stock. Our business, financial condition, results of operations or prospects could be materially and adversely affected by any of these risks or uncertainties, as well as by risks or uncertainties not currently known to us, or that we do not currently believe are material. In that case, the trading price of our common stock could decline, and you may lose all or part of your investment. Proprietary and Confidential | 48#49Summary of Risks (2/3) Risks Relating to Our Business 1. We have a history of net losses and we may not achieve or maintain profitability in the future. 2. 3. 4. 5. 6. 19 7. 8. 9. Our success and ability to grow our business depend on retaining and expanding our customer base. If we fail to add new customers or retain current customers, our business, revenue, operating results and financial condition could be harmed. The "Hippo" brand may not become as widely known as incumbents' brands or the brand may become tarnished. Denial of claims or our failure to accurately and timely pay claims could materially and adversely affect our business, financial condition, results of operations and prospects. Our limited operating history makes it difficult to evaluate our current business performance, implementation of our business model and our future prospects. We may not be able to manage our growth effectively. Intense competition in the segments of the insurance industry in which we operate could negatively affect our ability to attain or increase profitability. Reinsurance may be unavailable at current coverage, limits or pricing, which may limit our ability to write new or renew existing business. Furthermore, reinsurance subjects our insurance company subsidiaries to counterparty credit and performance risk and may not be adequate to protect us against losses, which could have a material effect on our results of operations and financial condition. Failure to maintain our risk-based capital at the required levels could adversely affect the ability of our insurance subsidiaries to maintain regulatory authority to conduct our business. 10. Failure to maintain our financial ratings could adversely affect the ability of our insurance company subsidiaries to conduct our business as currently conducted. 11. If we are unable to expand our product offerings, our prospects for future growth may be adversely affected. 12. Our proprietary technology, which relies on third party data, may not operate properly or as we expect it to. 13. Our technology platform may not operate properly or as we expect it to operate. 14. Our future success depends on our ability to continue to develop and implement our technology, and to maintain the confidentiality of this technology. 15. New legislation or legal requirements may affect how we communicate with our customers, which could have a material adverse effect on our business model, financial condition, and results of operations. 16. We rely on external data and our digital platform to collect and evaluate information that we utilize in producing, pricing and underwriting our insurance policies (in accordance with the rates, rules, and forms filed with our regulators, where required), managing claims and customer support, and improving business processes. Any legal or regulatory requirements that might restrict our ability to collect or utilize this data or our digital platform, or an outage by a data vendor could thus materially and adversely affect our business, financial condition, results of operations and prospects. 17. We depend on search engines, content based online advertising, other online sources to attract consumers to our website, which may be affected by third party interference beyond our control. In addition, our producer and partner distribution channels are significant sources of new customers and could be impacted by third party interference or other factors. As we grow our customer acquisition costs may increase. 18. We may require additional capital to grow our business, which may not be available on terms acceptable to us or at all. 19. Interruptions or delays in the services provided by our providers of third-party technology platforms or our internet service providers could impair the operability of our website and may cause our business to suffer. 20. Security incidents or real or perceived errors, failures or bugs in our systems or website could impair our operations, result in loss of personal customer information, damage our reputation and brand, and harm our business and operating results. 21. Misconduct or fraudulent acts by employees, agents or third parties may expose us to financial loss, disruption of business, regulatory assessments and reputational harm. 22. Our success depends, in part, on our ability to establish and maintain relationships with quality and trustworthy service professionals. 23. We may be unable to prevent, monitor or detect fraudulent activity, including policy acquisitions or payments of claims that are fraudulent in nature. 24. We are periodically subject to examinations by our primary state insurance regulators, which could result in adverse examination findings and necessitate remedial actions. 25. We collect, process, store, share, disclose and use customer information and other data, and our actual or perceived failure to protect such information and data, respect customers' privacy or comply with data privacy and security laws and regulations could damage our reputation and brand and harm our business and operating results. 26. We employ third-party licensed software for use in our business, and the inability to maintain these licenses, errors in the software we license or the terms of open source licenses could result in increased costs or reduced service levels, which would adversely affect our business. 27. We may be unable to prevent or address the misappropriation of our data. 28. We rely on the experience and expertise of our founder, senior management team, highly-specialized insurance experts, key technical employees and other highly skilled personnel. 29. If our customers were to claim that the policies they purchased failed to provide adequate or appropriate coverage, we could face claims that could harm our business, results of operations and financial condition. 30. We may become subject to claims under Israeli law for remuneration or royalties for assigned service invention rights by our Israel-based contractors or employees, which could result in litigation and adversely affect our business. Our company culture has contributed to our success and if we cannot maintain this culture as we grow, our business could be harmed. 31. 32. If we are unable to underwrite risks accurately and charge competitive yet profitable rates to our customers, our business, results of operations and financial condition will be adversely affected. 33. Our exposure to loss activity and regulation may be greater in states where we currently have most of our customers or where we are domiciled. 34. Our product development cycles are complex and subject to regulatory approval, and we may incur significant expenses before we generate revenues, if any, from new products. 35. New lines of business or new products and services may subject us to additional risks. 36. Litigation and legal proceedings filed by or against us and our subsidiaries could have a material adverse effect on our business, results of operations and financial condition. 37. Failure to protect or enforce our intellectual property rights could harm our business, results of operations and financial condition. Proprietary and Confidential | 49#50Summary of Risks (3/3) 38. Claims by others that we infringed their proprietary technology or other intellectual property rights could harm our business. 39. If we are unable to make acquisitions and investments, or successfully integrate them into our business, our business, results of operations and financial condition could be adversely affected. 40. Recent U.S. tax legislation may materially adversely affect our financial condition, results of operations and cash flows. 59. Our insurance company subsidiaries are subject to assessments and other surcharges from state guaranty funds, and mandatory state insurance facilities, which may reduce our profitability. 60. Performance of our investment portfolio is subject to a variety of investment risks that may adversely affect our financial results. 41. We may not be able to utilize a portion of our net operating loss carryforwards ("NOLS") to offset future taxable income for U.S. 61. Unexpected changes in the interpretation of our coverage or provisions, including loss limitations and exclusions, in our policies federal income tax purposes, which could adversely affect our net income and cash flows. 42. Our expansion strategy will subject us to additional costs and risks and our plans may not be successful. 43. Fluctuations in foreign currency exchange rates may adversely affect our financial results. Risks Relating to Our Industry 44. The insurance business, including the market for homeowners insurance, is historically cyclical in nature, and we may experience periods with excess underwriting capacity and unfavorable premium rates, which could adversely affect our business. 45. We are subject to extensive insurance industry regulations. 46. A regulatory environment that requires rate increases to be approved and that can dictate underwriting practices and mandate participation in loss sharing arrangements may adversely affect our results of operations and financial condition. 47. State insurance regulators impose additional reporting requirements regarding enterprise risk on insurance holding company systems, with which we must comply as an insurance holding company. 48. The increasing adoption by states of cybersecurity regulations could impose additional compliance burdens on us and expose us to additional liability. 49. The COVID-19 pandemic has caused disruption to our operations and may negatively impact our business, key metrics, or results of operations in numerous ways that remain unpredictable. could have a material adverse effect on our financial condition and results of operations. Risks Relating to Ownership of Our Common Stock 62. There may not be an active trading market for our common stock, which may make it difficult to sell shares of our common stock. 63. The market price of our common stock may be highly volatile, which could cause the value of your investment to decline. 64. There can be no assurance that the Company's securities will be approved for listing on NYSE or Nasdaq, as the case may be, or that the Company will be able to comply with the continued listing standards of such exchange. 65. If securities or industry analysts do not publish or cease publishing research or reports about us, our business or our markets, or if they adversely change their recommendations or publish negative reports regarding our business or our stock, our stock price and trading volume could materially decline. 66. Some provisions of our charter documents and Delaware law may have anti-takeover effects that could discourage an acquisition of us by others, even if an acquisition would be beneficial to our stockholders, and may prevent attempts by our stockholders to replace or remove our current management. 67. Applicable insurance laws may make it difficult to effect a change of control. 68. 50. Severe weather events and other catastrophes, including the effects of climate change, global pandemics and terrorism, are inherently unpredictable and may have a material adverse effect on our financial results and financial condition. 51. We expect our results of operations to fluctuate on a quarterly and annual basis. In addition, our operating results and operating metrics are subject to seasonality and volatility, which could result in fluctuations in our quarterly revenues and operating results or in perceptions of our business prospects. Our Amended Charter designates the Court of Chancery of the State of Delaware as the exclusive forum for certain litigation that may be initiated by our stockholders, which could limit our stockholders' ability to obtain a favorable judicial forum for disputes with us. 69. Claims for indemnification by our directors and officers may reduce our available funds to satisfy successful third-party claims against us and may reduce the amount of money available to us. 70. Taking advantage of the reduced disclosure requirements applicable to "emerging growth companies" may make our common stock less attractive to investors. 52. An overall decline in economic activity could have a material adverse effect on the financial condition and results of operations 71. Failure to establish and maintain effective internal controls in accordance with Section 404 of the Sarbanes-Oxley Act could of our business. 53. We rely on data from our customers and third parties for pricing and underwriting our insurance policies and handling claims, the unavailability or inaccuracy of which could limit the functionality of our products and disrupt our business. 54. Our results of operations and financial condition may be adversely affected due to limitations in the analytical models used to assess and predict our exposure to catastrophe losses. 55. We are subject to payment processing risk. 56. Our success depends upon the continued growth and acceptance of our products and services. 57. Our actual incurred losses may be greater than our loss and loss adjustment expense reserves, which could have a material adverse effect on our financial condition and results of operations. 58. Our insurance company subsidiaries are subject to minimum capital and surplus requirements, and failure to meet these requirements could subject us to regulatory action. have a material adverse effect on our business and stock price. 72. We depend on the ability of our subsidiaries to transfer funds to us to meet our obligations, and our insurance company subsidiaries ability to pay dividends to us is restricted by law. 73. We do not currently expect to pay any cash dividends. 74. The requirements of being a public company, including compliance with the reporting requirements of the Exchange Act, the requirements of the Sarbanes-Oxley Act and the Dodd-Frank Act and the listing standards of NYSE, may strain our resources, increase our costs, and divert management's attention, and we may be unable to comply with these requirements in a timely or cost-effective manner. In addition, key members of our management team have limited experience managing a public company. Proprietary and Confidential | 50