#1FOXO™ Investor Deck#2Disclaimer General This presentation does not constitute an offer or invitation for the sale or purchase of securities and has been prepared solely for informational purposes. The information contained in this presentation (this "Presentation") has been prepared for the exclusive use of the selected persons to whom it is addressed ("Recipients"), solely for the purpose of their own independent evaluation with respect to the proposed business combination (the "Proposed Transaction") between Delwinds Insurance Acquisition Corp. ("Delwinds") and FOXO Technologies Inc. (together with its subsidiaries, "FOXO"), and for no other purpose. This Presentation is subject to updating, completion, revision, verification and further amendment. None of Delwinds, FOXO, or their respective affiliates has authorized anyone to provide interested parties with additional or different information. No securities regulatory authority has expressed an opinion about the securities discussed in this Presentation and it is an offense to claim otherwise. The information contained herein does not purport to be all- inclusive. Nothing herein shall be deemed to constitute investment, legal, tax, financial, accounting or other advice. Neither this Presentation nor its delivery to Recipient shall constitute an offer to sell, invitation or other solicitation of an offer to buy any securities pursuant to the Proposed Transaction or otherwise, nor shall there by any sale of securities in any jurisdiction in which the offer, solicitation or sale would be unlawful prior to the registration or qualification under the securities laws of any such jurisdiction. No offer shall be made except by means of a prospectus meeting the requirements of Section 10 of the Securities Act of 1933, as amended. Only the express provisions of any agreement, if and when it is executed, shall have any legal effect in connection with the Proposed Transaction between the parties thereto. This Presentation is not intended to form the basis of any investment decision. All information herein speaks only as of (1) the date of this Presentation, in the case of information about FOXO, or (2) the date of such information, in the case of information from persons other than FOXO. Confidentiality This information is being distributed to Recipients on a confidential basis. By receiving this information, Recipients agree to maintain the confidentiality of the information contained herein and that no portion of this Presentation may either be reproduced in whole or in part and that neither this Presentation nor any of its contents may be given or disclosed to any third party without the express written permission of Delwinds and FOXO and that the information contained herein is subject to the terms of any confidentiality agreement entered into with Delwinds and FOXO. Any reproduction or distribution of this Presentation, in whole or in part, or the disclosure of its contents, without the prior written consent of Delwinds and FOXO is prohibited. By accepting this Presentation, each Recipient agrees: (i) to maintain the confidentiality of all information that is contained in this Presentation and not already in the public domain, and (ii) to use this Presentation for the sole purpose of independent evaluation of the Proposed Transaction. Forward-Looking Information This Presentation contains forward-looking statements for purposes of the "safe harbor" provisions under the United States Private Securities Litigation Reform Act of 1995. Any statements other than statements of historical fact contained in this Presentation, including statements as to future results of operations and financial position, planned products and services, business strategy and plans, objectives of management for future operations of FOXO, market size and growth opportunities, competitive position and technological and market trends, are forward-looking statements. Such forward-looking statements include, but not limited to, expectations, hopes, beliefs, intentions, plans, prospects, financial results or strategies regarding FOXO and the Proposed Transaction and the future held by the respective management teams of Delwinds or FOXO, the anticipated benefits and the anticipated timing of the Proposed Transaction, future financial condition and performance of FOXO and expected financial impacts of the Proposed Transaction (including future revenue, pro forma enterprise value and cash balance), the satisfaction of closing conditions to the Proposed Transaction, the related financing transaction, the level of redemptions of Delwinds' public stockholders and the products and markets and expected future performance and market opportunities of FOXO. These forward-looking statements generally are identified by the words "anticipate," "believe," "could," "expect," "estimate," "future," "intend," "may," "might," "strategy," "opportunity," "plan," "project," "possible," "potential," "project," "predict," "scales," "representative of," "valuation," "should," "will," "would," "will be," "will continue," "will likely result," and similar expressions, but the absence of these words does not mean that a statement is not forward-looking. Forward-looking statements are predictions, projections and other statements about future events that are based on current expectations and assumptions and, as a result, are subject to risks and uncertainties. Many factors could cause actual future events to differ materially from the forward-looking statements in this Presentation, including but not limited to: (i) the risk that the Proposed Transaction may not be completed in a timely manner or at all, which may adversely affect the price of Delwinds' securities, (ii) the risk that the Proposed Transaction may not be completed by Delwinds' business combination deadline and the potential failure to obtain an extension of the business combination deadline if sought by Delwinds, (iii) the failure to satisfy the conditions to the consummation of the Proposed Transaction, including the approval of the merger agreement by the stockholders of Delwinds and the receipt of certain governmental and regulatory approvals,, (iv) the inability to complete the financing agreements by one or more of the investors, (v) the occurrence of any event, change or other circumstance that could give rise to the termination of the merger agreement, (vi) the effect of the announcement or pendency of the Proposed Transaction on FOXO's business relationships, operating results, and business generally, (vii) risks that the Proposed Transaction disrupts current plans and operations of FOXO, (viii) the outcome of any legal proceedings that maybe instituted against FOXO or against Delwinds related to the merger agreement or the Proposed Transaction, (ix) the ability to maintain the listing of Delwinds' securities on a national securities exchange, (x) changes in the competitive and regulated industries in which FOXO operates, variations in operating performance across competitors, changes in laws and regulations affecting FOXO's business and changes in the combined capital structure, (xi) the ability to implement business plans, forecasts, and other expectations after the completion of the Proposed Transaction, and identify and realize additional opportunities, (xii) the potential inability of FOXO to achieve its commercialization and development plans, (xiii) the enforceability of FOXO's intellectual property, including its patents and the potential infringement on the intellectual property rights of others, (xiv) the risk of downturns and a changing regulatory landscape in the highly competitive industry in which FOXO operates, and (xv) costs related to the Proposed Transaction and the failure to realize anticipated benefits of the Proposed Transaction or to realize estimated pro forma results and underlying assumptions, including with respect to estimated stockholder redemptions. The foregoing list of factors is not exhaustive. Recipients should carefully consider the foregoing factors and the other risks and uncertainties described in the "Risk Factors" section of the registration statement on Form S-4 discussed above and other documents filed or to be filed by Delwinds from time to time with the SEC. These filings identify and address other important risks and uncertainties that could cause actual events and results to differ materially from those contained in the forward-looking statements. Forward-looking statements speak only as of the date they are made. Recipients are cautioned not to put undue reliance on forward-looking statements, and FOXO and Delwinds assume no obligation and do not intend to update or revise these forward-looking statements, whether as a result of new information, future events, or otherwise. Neither FOXO nor Delwinds gives any assurance that either FOXO or Delwinds, or the combined company, will achieve its expectations. FOXO INVESTOR DECK 2022 Page 2#3Disclaimer Continued Financial Information; Use of Projections The financial and operating forecasts and projections contained herein represent certain estimates of FOXO as of the date thereof and include projected financial numbers, including revenues, valuation and other metrics derived therefrom. FOXO's independent public accountants and auditors have not examined, reviewed or compiled the forecasts or projections and, accordingly, does not express an opinion or other form of assurance with respect thereto. Furthermore none of FOXO or its management team can give any assurance that the forecasts or projections contained herein accurately represents FOXO's future operations or financial condition. Such information is subject to a wide variety of significant business, economic and competitive risks and uncertainties that could cause actual results to differ materially from those contained in the prospective financial information. Accordingly, there can be no assurance that the prospective results are indicative of the future performance FOXO or that actual results will not differ materially from those presented in these materials. Some of the assumptions upon which the projections are based inevitably will not materialize and unanticipated events may occur that could affect results. Therefore, actual results achieved during the periods covered by the projections may vary materially from the projected results. Inclusion of the prospective financial information in these materials should not be regarded as a representation by any person that the results contained in the prospective financial information are indicative of future results or will be achieved. Use of Non-GAAP Financial Matters This Presentation and the accompanying oral presentation include certain financial measures not presented in accordance with generally accepted accounting principles ("GAAP") with respect to FOXO's expected future performance and other metrics derived therefrom. These non-GAAP financial measures may exclude items that are significant in understanding and assessing FOXOS financial results. 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 as a measure of our liquidity, profitability or performance. Not all of the information necessary for a quantitative reconciliation of these non-GAAP financial measures to the most directly comparable GAAP financial measures is available without unreasonable efforts at this time. Delwinds and FOXO believe that these forward-looking non-GAAP measures of financial results provide useful supplemental information about FOXO. FOXO's management uses these forward-looking non-GAAP measures to evaluate FOXO'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 FOXO's non-GAAP measures may not be directly comparable to similarly titled measures of other companies. The presentation of such non-GAAP measures, which may include adjustments to exclude unusual or non-recurring items, should not be construed as an inference that FOXO's future results and cash flows will be unaffected by other unusual or nonrecurring items. Industry and Market Data This Presentation has been prepared by FOXO and includes market data and other statistical information from third-party sources. Although FOXO believes these third-party sources are reliable as of their respective dates, none of Delwinds, FOXO, or any of their respective affiliates has independently verified the accuracy or completeness of this information. Some data are also based on FOXO's good faith estimates, which are derived from both internal sources and the third-party sources described above. None of Delwinds, FOXO, their respective affiliates, nor their respective advisors, directors, officers, employees, members, partners, stockholders or agents make any representation or warranty with respect to the accuracy of such information. None of Delwinds, FOXO or their respective affiliates, advisors, directors, officers, employees, members, partners, stockholders or agents or the providers of any such third party information or any other person are responsible for any errors or omissions therein (negligent or otherwise), regardless of the cause, or the results obtained from the use of such content. Each of Delwinds, FOXO and their respective affiliates, advisors, directors, officers, employees, members, partners, stockholders and agents expressly disclaims any responsibility or liability for any damages or losses in connection with the use of such information herein. Important Information Neither the delivery of this Presentation nor the purchase of any of the securities, assets, businesses or undertakings of FOXO after the date hereof shall, under any circumstances, be construed to indicate or imply that there has been no change in the affairs of FOXO since the date hereof. This Presentation does not purport to be all-inclusive or to contain all the information that a Recipient may desire in deciding whether or not to proceed with the Proposed Transaction and is not intended to form the basis of any investment decision. No representation or warranty, express or implied, is or will be given by Delwinds, FOXO or their respective affiliates, representatives, advisors, directors or employees and no responsibility or liability or duty of care is or will be accepted by Delwinds, FOXO or their respective affiliates, representatives, advisers, directors or employees as to the accuracy, completeness, reliability or reasonableness of the information or opinions contained in this Presentation or supplied herewith or any other written or oral information made available to any interested party or its advisers in connection with the Proposed Transaction or otherwise in connection with this Presentation. To the fullest extent possible, by receiving this Presentation the Recipient acknowledges and agrees it is not relying on any information set forth in this Presentation and releases each of Delwinds, FOXO and each of their respective affiliates, representatives, advisers, directors and employees in all circumstances from any liability with respect to the Recipient's participation, or proposed participation, in the Proposed Transaction. In addition, no responsibility or liability or duty of care is or will be accepted by Delwinds, FOXO or their respective affiliates, representatives, advisers, directors or employers for updating or revising this Presentation or providing any additional information to any Recipient and any such liability s expressly disclaimed. Accordingly, none of Delwinds, FOXO or their affiliates, advisers, directors or employees shall be liable for any direct, indirect or consequential loss or damage suffered by any person as a result of relying on any statement in or omission from this Presentation or in any other information or communications in connection with the Proposed Transaction. In particular, no representation or warranty of Delwinds, FOXO or their respective affiliates is given as to the achievement or reasonableness of future projections, management targets, estimates, prospects or turns, if any. Recipients should make their own investigation of the Proposed Transo Delwinds, FOXO and any related entity and all informati provided. vinds and FOXO each reserve the right, without reasons or advance notice, to change or terminate the procedure relating to the Proposed Transaction or any other transaction involving Delwinds or FOXO or to terminate negotiations at any time prior to the signing of any binding agreement in relation thereto. Trademarks and Intellectual Property All trademarks, service marks, and trade names of FOXO, its affiliates or other parties used herein are trademarks, service marks, or registered trade names of FOXO or such other parties, as noted herein. Any other product, company names, or logos mentioned herein are the trademarks and/or intellectual property of their respective owners, and their use is solely for convenience and i not intended to, and does not imply, a relationship with FOXO, or an endorsement or sponsorship by or of FOXO or any other party. The trademarks, service marks and trade names referred to in this presentation may appear without the *, TM or SM symbols, but such references are not intended to indicate, in any way, that FOXO will not assert, to the fullest extent under applicable law, their rights or the right of the applicable licensor to these trademarks, service marks and trade names. FOXO INVESTOR DECK 2022 Page 3#4STRUCTURED FOR SUCCESS Transacting with delwinds Delwinds Insurance Acquisition Corp. Andrew Poole Chairman and CEO IGI TIBERIUS GRAY Diamond back SAIC Swiss Re Hayley Locker Managing Director CINCTIVE B.A:M: Aptigon SCORIA Morgan Stanley FOXO INVESTOR DECK 2022 Page 4 Industry Validator Unparalleled access to potential customer relationships and insurance leaders • Tiberius sponsor remains invested in NASDAQ: IGIC since transaction close and has continued board participation (12) Transaction structure aligned with investors Approximately one-third of deal consideration is subject to management earn-out dependent on achievement of strategic milestones FOXO shareholders rolling 100% of their interest into transaction (3) Transaction closing not dependent on minimum cash condition (1) Mr. Poole was the Chief Investment Officer of Tiberius Acquisition Corporation (Nasdaq: TIBR), or Tiberius, a blank check company which went public in March 2018 with $174.225 million held in trust and which consummated its initial business combination with International General Insurance Holdings Ltd. (Nasdaq: IGIC), or IGI, an international specialty insurance and reinsurance group registered in Bermuda, in March 2020, on the day after the CBOE Volatility Index, or VIX, (which tracks the 30-day implied volatility of the S&P 500) closed at a record high. (2) Lagniappe Ventures, LLC distributed >85% ownership in IGIC to Mr. Poole, Michael T. Gray, Bryce Quin and The Gray Insurance Company, who, collectively, have increased their shareholdings in IGIC since transaction close. (3) Transaction provides FOXO Management with Class V common shares.#5FOXO INVESTOR DECK 2022 Page 5 FOXO TECHNOLOGIES This transaction makes longevity science fundamental to life insurance.#6KEY HIGHLIGHTS Investment thesis Multiple avenues for value creation COVID is driving life insurance sales, agents seeking new products with a smoother, simpler sales journey, and boom in health, wellness, and longevity FOXO INVESTOR DECK 2022 Page 6 Launching with scalable infrastructure E Built on a best-in-class technology platform with infrastructure capable of supporting scaled growth in a large and global industry O Next-Gen Life Insurance Platform to modernize industry with saliva- based epigenetic underwriting technology that eliminates blood and urine requirements, and embed longevity science as new value proposition for consumers Proprietary science and technology Proprietary and first-mover advantage in applying saliva-based epigenetic biomarker technology to underwriting, not easily reproduced or copied World class science and management Science confirmed by experts, value propositions rigorously validated, and prior management success in financial product creation and distribution#7EXPERT TEAM Proven leadership in insurance, longevity science, health, and technology. Jon Sabes CEO & Founder MINNESOTA LAW UNIVERSITY OF MINNESOTA University of Colorado FOXO INVESTOR DECK 2022 Page 7 Erin Sharoni Chief Product Officer HARVARD BRIDGEWATER MEDICAL SCHOOL OCBS Inside Tracker CNBC Brian Chen, PhD Chief Science Officer NIH National Institute on Aging UCLA Berkeley UC San Diego NIVERSITY OF CAU HAVAR Tyler Danielson Chief Technology Officer Cargill ASC Å brightpeak Robby Potashnick Chief Financial Officer pwc Blaige & Company UNITEDHEALTH GROUP#8There are moments in time when innovation is so radical, the course of civilization is forever changed. FOXO INVESTOR DECK 2022 Page 8 1910 Flight 1930 ' Antibiotics 1950 THE NEXT PARADIGM SHIFT Space 1970 PCs 1980 Internet 1990 Genomics 2000 Smart phones 2010 Energy 2020 Longevity#9This is the biological century. The rapid maturation of DNA sequencing, Al, and machine learning is transforming our understanding of biology and longevity. Technology Review, Antonio Regalado, 2021 Extending human healthspan and longevity: a symposium report, New York Academy of Science, 2021 FOXO INVESTOR DECK 2022 Page 9 FI CGG AAG CA TAA#10Molecular biotechnology is transforming human longevity The Economist The new era of corporate scandal Algeria kicks out its dictator Why Europe's banks are so rotten Great wheels of China Redesigning life The promise of synthetic biology FOXO INVESTOR DECK 2022 Page 10 ALTOS Altos Labs is a new biotechnology company focused on cellular rejuvenation programming to restore cell health and resilience, with the goal of reversing disease to transform medicine. A community of leading scientists, clinicians, and leaders from both academia and industry will work together towards this common mission. Altos will be initially based in the US in the San Francisco Bay Area and San Diego, and in the UK in Cambridge. The company will also have significant collaborations in Japan. THE SCIENCE OF HEALTHSPAN The Altos Board of Directors and advisors include Nobel Laureates and scientific leaders. "An elegant and exciting book that deserves to be read broadly and deeply" -Siddhartha Mukherjee, Päe Wi-winning and #1 Note Red Tie bestalling author Lifespan New York Times Bestseller Why We Age- and Why We Don't Have To David A. Sinclair, PhD, with Matthew D. LaPlante Flagship Pioneering The Biological Century The essence of the biological century is a virtuous cycle of advances in biological technologies and biological understanding. THE ᏟᎾᎠᎬ BREAKER #1 Jennifer Doudna, Gene Editing, AND THE Future of the Human Race Bestseller WALTER ISAACSON BESTSELLINE AUTHOR or Leonardo da Vinci a Steve Jobs#11on FOXO INVESTOR DECK 2022 Page 11 65 Co OUR MISSION To make longevity accessible to all, empower people to live healthier, own their data, and control their future.#12Life insurance designed to keep you alive" FOXO INVESTOR DECK 2022. Page 12 NEXT-GEN LIFE INSURANCE FILL TO Longevity by FOXOLIFE SALIVA-BASED UNDERWRITING + LONGEVITY REPORT 9:41 FOXOLIFE Longevity Report Biological Age Your result 36 Your Biological Age 42 Chronological Age TM#13AN UNPRECEDENTED OPPORTUNITY Life insurance is ripe for disruption. All figures are USD per annum. (1) American Council for Life Insurers, Life Insurers Fact Book 2020 (2) McKinsey 2020 Global Insurance Pools statistics and trends (3) Life underinsurance in the US: bridging the USD 25 trillion mortality protection gap, September 2018 FOXO INVESTOR DECK 2022 Page 13 2.6T GLOBAL LIFE INSURANCE PREMIUMS² 125B+ US INDIVIDUAL LIFE PREMIUMS ¹,2 25T+ US INDIVIDUAL LIFE PROTECTION GAP (100M CONSUMERS)³#14INDUSTRY STAKEHOLDERS: CORE CHALLENGES Consumers Product has low relevance and commoditized 1989 77% H.H. ownership of life insurance "Death isn't what it used to be" and products struggle for relevant value proposition (1) FOXO INVESTOR DECK 2022 Page 14 2021 52% (2) ↑ 21% Premium sales have. increased from 2Q20 COVID-19 (1) What Explains the Decline in Life Insurance Ownership?, Daniel Hartley, Anna Paulson, Katerina Powers, 2017; Insurance Barometer Study, Stephen Wood; Maggie Leyes; James T. Scanlon, M.S., HIA, 2021 (2) 2Q 2021 LIMRA U.S. Retail Individual Life Insurance Sales Agents Product is difficult to sell, underwriting is time consuming and invasive 30% Sales breakage rates of independent agents (3) 49% Of all life insurance. premiums are sold by independent agents (3) 52 Days Avg number of days to complete life insurance policy sale using full underwriting by agents (i.e., paramedical blood & urine specimen collection) (3) LIBRA Data (2021) (4) 2Q 2021 LIMRA U.S. Retail Individual Life Insurance Sales Carriers Incumbents are large, old and slow 1886" Avg Year of Founding Top 20 U.S. Carriers (6) 63% Carriers report not prepared to deal with genetic testing Carriers have not made effective use of science and technology to improve their products, cost inefficiencies and lackluster results. (5) LIMRA, Insurance carrier websites (6) Genetics Survey Results Public Report, Reinsurance Group of America, Incorporated, 2021#15FOXOLIFE B2B2C MODEL Insurance platform • Life insurance products Healthy longevity & Saliva-based underwriting • B2B2C: Offer to consumers via agents • Modernize products FOXO INVESTOR DECK 2022 Page 15 NOW FOXOLABS B2B MODEL Services platform • Consumer engagement & underwriting services ● Healthy longevity & Saliva-based underwriting B2B: Offer to insurance carriers . Modernize industry#16B2B2C FOXO FOXO INVESTOR DECK 2022 Page 16 Making longevity accessible healtting the Prot ealthy to moke r help you dople you love is important. So is staying both. Becau emories with th ecause that's how you build a lasting am. At FOXO, we're on an the heart As for up to fu vage 4 WANT Dun Insurance platform Longevity fundamental to life insurance Adaptable infrastructure Experienced team • Workbench for saliva-based underwriting At launch • Term life insurance, 10/20 yr <$1M • Accelerated underwriting - instant issue Epigenetic measures used for consumer engagement ONLY Coming soon Permanent & Term life insurance $1M+ • Distribution model with carrier partner (MGA) Saliva-based underwriting Epigenetic measures for consumer engagement FOXOLIFE BACKBONE 2 unqork aws illumina GENESEEK SALES OPERATIONS Hubspot A aircall SCOR The Art & Science of Risk Heap REINSURANCE PARTNER#17FOXO INVESTOR DECK 2022 Page 17 Longevity science Popularity • 30M+ consumers purchasing 23&Me, Ancestry.com, etc. • Consumer interest in longevity, health, science People want to live longer and healthier Opportunity • US ranks 26th of 35 OECD countries for life expectancy (1) Yet ranks 1st in healthcare spending per capita Reinvent life insurance with health & wellness Reward Healthspan for All Alignment of interests (consumers & insurance company) Health improvements can add $12 trillion or 8% to global GDP in 2040 (2) (1) Organization for Economic Co-operation and Development (2) McKinsey & Co, Prioritizing health: A prescription for prosperity. 2020#18Core values Accuracy "I know the data is correct." Transparency "I know what I'm paying for/receiving and how my data is being used." Trust "I know my data is secure, de-identified, and used ethically." Ownership "I know I have the power to collect and withdraw my data at any time." Non-discrimination "I know my data will not be unfairly used against me." FOXO INVESTOR DECK 2022 Page 18 COB#19Saliva-based underwriting Eliminates the need for invasive blood and urine collection, a revolutionary value proposition: Faster, cheaper, better Digital application / underwriting Instant approval with accelerated underwriting and reinsurance provided by SCOR Next-Gen Life Insurance Portal access View and edit your policy, access and update your health and wellness anytime Data download View, track, download, share, or opt out your epigenetic data FOXO INVESTOR DECK 2022 Page 19 FOXOLIFE Hi, Nicola Wecome to FOXO LIFE. We are so excited that you have joined us in your search for optimal performance and a longer, healthier lifespan. Longevity Report Your Biological Age Your Scores 4 Metabolic On Track " 10 / 20 YEAR TERM Inflammation Requires Attention My data 36 Cardiovascular Needs Improvement Indulgence Requires Attention VIEW Policy Insured Nicola Smith Policy # #100000000000 Net death benefit $1,500,000 Policy 20 Year Term Life Resources Terlal VIEW FOXO featured in Coverager & SCOR Health & Wellness White Paper FOXO featured in OTR. The Journal of the Academy of Life Underwriting Epigenetics in the Fight Against COVID-19 COMING ONINO SOON Longevity Report A first-to-market personalized Longevity Report includes insights into biological aging and epigenetic measures of health to directionally orient consumers toward wellness Biological Age An in-depth and accurate picture of your biological aging measured by epigenetic clock Epigenetic measures Proprietary metabolic, cardiovascular, inflammation and indulgence epigenetic scores based on clinical measures Scientific insights Access to latest scientific research on longevity contribute and health, as well as opportunities to to the growth of scientific knowledge#20FOXO LIFE Perfect product-market fit Epigenetic clock Age Acceleration Age-related disease Risk factors Cancer risk Stress (1) Maddock Douglas Survey (2019) FOXO INVESTOR DECK 2022 Page 20 Molecular health Age Deceleration Healthy aging Protective factors Healthy food intake Physical fitness Consumer & agent survey 58% Consumers in-market were interested in purchasing life insurance bundled with molecular health and wellness offering over other options (1) 10% Consumers out-of- market were interested in purchasing life insurance after hearing about molecular health and wellness offering bundled with life insurance 80% Agents surveyed would recommend life insurance bundled with molecular health and wellness to their clients#21(1) FOXOLIFE Apply in minutes for up to $1 million in coverage Receive actionable epigenetic health insights Uncover your biological age and rate of aging Powered by next-gen science & technology FOXOLIFE Life insurance, reimagined. LONGEVITY SCIENCE FOXO INVESTOR DECK 2022 Page 21 A whole new reason to buy life insurance We're changing how life insurance companies FOXOLIFE Automated Automates analysis of epigenetic data from Illumina arrays that measure DNA modifications that are altered in response to human behavior and biological processes Written in Python These open source software packages can run natively in command line, Jupyter notebooks, or automation scripts READY TO LAUNCH Pre-processing and quality control FOXOLIFE Your result Longevity Report Biological Age 36 Your Biological Age 42 Chronological Age FOXOLIFE FOXO universe 32% Of all participants have a Biological Age less than their Chronological Age. Your result is above average. Your chronological age FOXOLIFE Longevity Report Cardiovascular Score Needs Improvement Your Score Your Cardiovascular Score: Tested Jan 31, 2022 Samantha, your Cardiovascular Score Needs Improvement. = FOXOLIFE Transforming the future of research. We provide scientists with advanced epigenetic#22B2B FOXO INVESTOR DECK 2022 Page 22 Services platform Proprietary science Experienced team Adaptable & scalable infrastructure • Global opportunity to modernize industry Saliva-based underwriting Enhanced accelerated underwriting • Eliminate sales friction / eliminate sales breakage Improved underwriting protective values Open new markets for life insurance sales Consumer engagement • Creating a new value-proposition Improving consumer health and longevity Utilizing multi-omic health and wellness FOXOLABS BACKBONE illumina python DataRobot aws SCOR The Art & Science of Risk#23LONGEVITY SCIENCE We're modernizing underwriting with saliva-based epigenetic biomarkers. FOXO INVESTOR DECK 2022 Page 23 Hogia-value)#24EPIGENETIC BIOMARKERS Why saliva-based underwriting is a compelling opportunity • LIMRA identifies medical underwriting as the single greatest pain point in this customer experience (1) . Agents loathe inconvenient, invasive, time consuming blood & urine specimen collection required for medical underwriting Accelerated underwriting is growing but represents only a fraction of business produced by Agents Agents represent 77% of all life insurance premiums sold in U.S. (2) Regulatory does not prohibit use of epigenetic information to measure same risk factors obtained through blood and urine "All things being equal, the carrier that adopts saliva-based underwriting in replacement of blood and urine specimens doesn't get some of the agent business, they get all of it" (3) (1) LIMRA https://www.limra.com/en/events/conferences/2022/2022-life-insurance-conference/ (2) 2Q 2021 LIMRA U.S. Retail Individual Life Insurance Sales (3) Maddock Douglas Survey (2019) FOXO INVESTOR DECK 2022 Page 24#25What is epigenetics? DNA is your genetic code. x FOXO INVESTOR DECK 2022 Page 25 Inherited from parents Fixed at birth Determines ancestry, ethnicity, gender, eye color, and predisposition to health risks Epigenetics is the expression of that code. DO Changing, modifiable, adapting, and reacting Associated with age-related decline, and disease states Impacted by tobacco, alcohol, diet, exercise, stress, and environmental factors#26EPIGENETIC BIOMARKERS Use case Epigenetics can distinguish between current, former and never smokers comparing favorably to the life insurance industry's use of cotinine biomarkers and self-reporting. Epigenetics can distinguish between individuals of excellent, standard, and poor health - comparing favorably to the life insurance industry's use of underwriting risk classifications. FOXO INVESTOR DECK 2022 Page 26 Genetically identical twins Images: Illustrating Effect of Epigenetic Differences in Identical Twins, Underwriting Risk Classifications Epigenetic Health Profiles Tobacco use Probability of Tobacco Use 1.0 0.8 0.6 04 Decline 0.2 Table Rated. Full Medical Underwriting Risk Classifications : Standard Standard Preferred Preferred Plus Tobacco Non-Tobacco Non-Tobacco Non-Tobacco Current Smoking Categories Never#27PROPRIETARY Epigenetic biomarkers We use automated machine learning to find patterns of DNA methylation occurring along the epigenome that correlate to current states health and wellness. We call these identifiable patterns "epigenetic biomarkers." FOXO Patent Applications Risk Classifier: USAN 16/579,777 (filed September 23, 2019) Biochemical State and/or Medical Condition Estimator: USAN 16/579,818 (filed September 23, 2019) Synthetic Probe: USAN 16/591,296 (filed October 2, 2019) Machine-Learned Quality Control for Epigenetic Data: USAN 17/482,405 (filed September 22, 2021) Licensed Patent Applications from UCLA GrimAge: USAN 17/282,318 (filed April 1, 2021) PhenoAge: USAN 16/963,065 (filed July 17, 2020) M-Panel: USAN 16/323,490 (filed February 5, 2019) (1) Results from STP1 data set, and subject to further testing and validation; FOXO Forward Looking Statement FOXO INVESTOR DECK 2022 Page 27 Health status data *****-- Epigenetic biomarkers Proprietary algorithms to measure human health Epigenetic biomarkers Tobacco / Nicotine Use Hypertension Obesity Cardiovascular Disease NT-proBNP Diabetes Epigenetic data Alcohol Abuse Cannabis Use Accuracy(1) 99% 79% 74% 83% 93% 80% 97% 90%#28RESEARCH Collaborations Physicians' Health Study VITAL Study COSMOS Trial FOXO Study Industry Pilot Studies FOXO INVESTOR DECK 2022 Page 28 • Epigenetic and health status data on 11,340 physicians • 30 years follow-up • 2,000+ mortality events and other major diseases • Epigenetic and health status data in 800 men and women • Clinical trial on vitamin D3 and omega-3 fatty acids (fish oil) supplementation • Focus on cancer, heart disease, and stroke • Epigenetic and health status data in 1,200 men and women • Clinical trial on multivitamins and cocoa flavanol supplementation • Focus on cancer, heart disease, and stroke • Epigenetic data in blood and saliva of ~5,000 men and women • Nation-wide study collecting blood, urine, saliva, and medical records. • Focus on tobacco use, alcohol use, diabetes, obesity, hypertension, and dyslipidemia • Parallel underwriting study with traditional health data and epigenetic data • Focused on achieving same or better risk classification from epigenetic data • Provides data for companies to tailor epigenetic testing into their unique workflows SCIENTIFIC Advisory Board Peter Laird, PhD Hui Shen, PhD Bret Barnes, PhD* Murdoc Khaleghi, MD* Randal Olson, PhD *FOXO Board of Directors Epigenetics Van Andel Institute (VAI) Bioinformatics Van Andel Institute (VAI) Biotechnology Illumina, Inc. Consumer Health WellnessFX AI Data scientist & Al researcher#29EPIGENETIC BIOMARKERS Underwriting protocols Policy face amount $0-$449,999 $500,000-$999,999 $1,000,000-$2,999,999 $3,000,000-$4,999,999 $5,000,000+ 21-30 FOXO INVESTOR DECK 2022 Page 29 Data Data Data Paramed Data Paramed Data Paramed APS (1) Local Life Agents; LIMRA Data (2018); FOXO Forward Looking Statement 31-50 Data Data Data Paramed Data Paramed Data Paramed APS Sweet spot for agent driven business (1) Insured age 51-60 Data Data Data Paramed Data Paramed Data Paramed APS 61-70 Data Paramed Data Paramed Data Paramed Data Paramed APS Data Paramed APS 71+ Data Paramed APS Data Paramed APS Data Paramed APS Data Paramed APS Data Paramed APS Accelerated underwriting Saliva-based underwriting Medical underwriting#30EPIGENETIC BIOMARKERS Underwriting protocols Accelerated underwriting Application Saliva-based underwriting Application Data Application Medical underwriting FOXO INVESTOR DECK 2022 Page 30 Data Data Decision Saliva Blood/Urine Instant Decision Days APS Saliva is less invasive and easier to collect Epigenetics generates information similar to blood/urine tests for underwriting Provides significantly more protective value information than accelerated underwriting data only Decision Weeks#31EPIGENETIC BIOMARKERS Underwriting protective value framework Example: $2M policy, male, age 35 Accelerated Saliva-based Medical Underwriting Information FOXO INVESTOR DECK 2022 Page 31 Online questionnaire / database Accelerated underwriting Epigenetic biomarkers + Online questionnaire / database Blood & Urine specimen Medical Records (APS) Underwriting Cost Over Accelerated N/A $333 (2) $600 Underwriting Expected Claims (1) $17,506 $17,191 (40% of Full) $17,112 (50% of Full) $16,915 (75% of Full) $16,717 (1) SOA VBT Tables (2018) (2) $333 represents the modeled cost to insurance carriers at scale ($160 cost of epigenetic testing plus $173 ( 5% of premiums using services platform) Gross Claims Benefit Over Accelerated Underwriting N/A $316 $395 $592 $789 Net Claims Benefit After Underwriting Cost N/A ($17) $62 $259 $189 Protective Value Benefit#32REVENUES & PROFITABILITY Business model. FOXO INVESTOR DECK 2022 Page 32 126 49546792 V Sara#33COMMERCIALIZATION Development plan We are executing a three phase development plan for the growth of our products and services. FOXO INVESTOR DECK 2022 Page 33 NOW Preparation Complete proprietary epigenetic biomarker R&D • Build technology stack to support operations Acquire life insurance company: FOXO Life Insurance Company B2B2C MODEL Insurance platform Capitalize company and begin selling life insurance products Quickly expand life insurance products with carrier partner (MGA) Adopt Saliva-based Underwriting into products (MGA) Expand distribution with Independent Agents (MGA) B2B MODEL Services platform • Sell saliva-based underwriting technology and consumer engagement services to domestic and international insurance carriers#34SALIVA-BASED UNDERWRITING Market share capture Insurance carriers adopting accelerated underwriting (1) (2) 1 2014 10 FOXO INVESTOR DECK 2022 Page 34 2016 23+ 2018 46+ 2020 (1) AMERICAN ACADEMY OF ACTUARIES Simplified Issue and Accelerated Underwriting (page 9) (2) Automated and Accelerated Underwriting Life Insurance Company Practices in 2019 (page 12) (3) FitchSolutions United States Insurance Report Q4 2021. Society of Actuaries, Emerging Underwriting Methodologies. (2018) Study provides a estimates of % policies submitted through accelerated underwriting for 2018, 2023, and 2028 of 42%, 57%, and 79%, respectively. Projected policies eligible for accelerated underwriting and modelled saliva-based underwriting market share capture (3) 12,000 10,000 8,0 00 6,0 00 4,000 2,000 2022 2023 Accelerated underwriting Medical underwriting 2024 Target market opportunity is the projected growth in accelerated underwriting 2025 2026 Accelerated underwriting projected growth 2027#35POLICIES SOLD & SERVICED Revenues and total EBITDA by platform Pro-forma policies by platform (,000 thousands) 2,000 1,800 1,60 0 1,400 1,200 1,000 80.0 600 400 200 0 20 22 20 23 FOXO MGA 20 24 ✔ FOXO Services FOXO INVESTOR DECK 2022 Page 35 20 25 FOXO LIFE Policies sold by platform are based on the following assumptions: 20 26 . FOXO is targeting large insurance carrier customers, which issue on average 170k policies per annum. . FOXO is modeling product sales growing under a MGA arrangement with third-party insurance carrier in 2023. (1) FOXO Technologies, Pro-Forma Policies Sold, Revenues, and EBITDA Projections are Forward Looking 20 27 Pro-Forma Revenue by Platform and Total EBITDA ($USD Millions) $1,600 $1,400 $1,200 $1,000 $8.00 $6.00 $400 $200 $0 (1) ($ 200 ) 20 22 20 23 FOXO MGA 20 24 FOXO Services 20 25 20 26 FOXO LIFE Premiums Revenue and EBITDA projections are based on the following assumptions: 2027 EBITDA • FOXO MGA revenue is from gross commissions of 135% of the first-year premium of insurance products sold. . FOXO Services revenue is from (i) technology service fees of 7.5% of the first-year premium of policies using Saliva-based Underwriting and Consumer Engagement services; and (ii) costs of providing testing services of -$160 per policy. . FOXO Life premiums from insurance policies sold for The FOXO Life Insurance Company of $1mm, $3mm, $7mm, $5mm, $5mm, and $5mm for the years 2022, 2023, 2024, 2025, 2026, and 2027, respectively. • The average first year premium is modeled at -$3,500#36Transaction Summary Overview Transaction Consideration of $300mm, subject to closing adjustments, inclusive of $100mm management earnout shares, subject to achievement of post-close milestones Transaction will be funded by Delwinds Insurance Acquisition Corp. cash in trust of $201mm (assuming no redemptions) and issuance of common stock to existing FOXO shareholders (1) • Total estimated gross proceeds of $224mm at closing, including cash in trust (assuming no redemptions) and proceeds of FOXO issuance of convertible debentures (1) • Andrew J. Poole, Delwinds' Chairman and CEO, alongside Gray & Company, Inc., to invest $10mm in the event the trust does not maintain at least $10mm in cash (1) • FOXO has secured a $40mm committed equity facility from an affiliate of Cantor Fitzgerald Net cash proceeds to FOXO balance sheet to accelerate and fund growth initiatives There is no cash closing condition for the transaction FOXO existing shareholders and management rolling 100% of their equity into the transaction Cash Sources and Uses ($mm) Sources of Cash Delwinds cash in trust(1) FOXO rollover equity(2) Total sources of cash $201 FOXO INVESTOR DECK 2022 Page 36 $300 $501 Uses of Cash FOXO rollover equity(²) Cash to balance sheet Transaction expenses Total uses of cash $300 $171 $30 $501 Pro Forma Valuation Total shares outstanding (3) Price per share Equity value Less: net cash(4) Total enterprise value TEV / Rev (2023) $mm, except per share data 17.8% 0.9% 10.1% 35.5% 56.3 35.7% $10.00 Pro Forma Illustrative Ownership Breakdown $563 ($194) $369 2.5X Del winds Shareholders FOXO Equity Holders 100% Rollover Management Earnout Delwinds Sponsor Other Shareholders (1) Assumes no redemptions of public shares by Delwinds Insurance Acquisition Corp. stockholders. Amount will be reduced by the amount of cash used to satisfy any redemptions. Contingent subscription obligation, subject to offset, in form of subscription for common stock or convertible debt. (2) FOXO rollover equity is inclusive of convertible debenture. (3) Pro forma share count includes 20.0mm FOXO rollover shares, 20.1mm SPAC shares, 10.0mm Management earnout shares, 5.7mm Sponsor shares, and 0.5mm other shares. FOXO rollover shares are inclusive of convertible debenture. (4) Includes net cash to balance sheet from Delwinds trust account, as well as cash from convertible debenture. (5) Excludes the impact of 10.4mm SPAC warrants#37Implied Valuation Significant potential for meaningful investor value creation Applies 1.7x-6.3x EV / revenue multiple to FOXO's 2025E revenue to arrive at an implied future enterprise value The range reflects the fact that there is no company perfectly comparable to FOXO and we are using a broad peer set Implied future enterprise value is discounted 4 years at an illustrative 50% rate FOXO is offered at a 41% discount to a conservatively derived illustrative enterprise value HIGH GROWTH DISTRIBUTION DIAGNOSTICS BIOTECH INSURTECH FOXO™ Note: This slide contains projected financial information. Such projected financial information constitutes forward looking information and is for illustrative purposes only and should not be relied upon as necessarily being indicative of future results. FOXO INVESTOR DECK 2022 Page 37 Relative Valuation ($B) $5.0 $1.4 2025E EV implied by 1.7x-6.3x revenue of $789M $1.0 $0.3 2025E Current EV implied by discounting EV by 50% discount rate Transaction Value Represents 41% discount to midpoint $369M EV FOXO Note: Valuation utilizes 2023E High Growth Distribution and 2024E Diagnostics Biotech and Insurtech peer multiples due to lack of sufficient analyst estimates beyond those years.#38Comparable company analysis FOXO's focus on longevity differentiates it from peers '22E - ¹23E Revenue Growth '23E '24E Revenue Growth Average 2023E EV / Revenue Average 2024E EV / Revenue Fast Growing Recurring Revenues No / Limited Balance Sheet High R&D Expenditures Exclusive IP Regulatory Oversight FOXO(¹) FOXO FOXO INVESTOR DECK 2022 Page 38 156% 105% 2.5x 1.0x High Growth Distribution (2) BRP goosehead INSURANCE HAGERTY. RSG 36% 29% 8.2x 6.3x Diagnostics Biotech Adaptive BIOCARTIS EXACT SCIENCES Myriad genetics sema4 GUARDANT veracyte natera Prenetics 27% 28% 4.4X CareDx 3.6x INVITAE 23andMe (2) High Growth Distribution based on 2022E-2023E metrics due to lack of sufficient analyst estimates beyond 2023. (3) HSCM Public InsurTech Index comprised of BHG, BRP, CCCS, CLOV, DOMA, DCT, ESNT, EVER, GOCO, GSHD, GWRE, HIPO, KNSL, LMND, MAX, MILE, OSCR, PLMR, QNST, ROOT, SLQT, and TRUP. Insurtech (3³) HSCM Public InsurTech Index 29% 22% 3.0x Source: Company filings, investor presentations, FactSet, and SNL Market data as of 02/18/2022. Note: This slide 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. (1) FOXO revenue growth rates based on '23E-'24E and '24E-25E to illustrate growth incorporating MGA business. 1.7x#39Public Comparable Comps: Benchmarking Operational Valuation 156% FOXO INVESTOR DECK 2022 Page 39 '23-24E FOXO 2.5x 2023E FOXO 36% '21E - ¹22E High Growth Distribution (¹) 8,2x 2022E High Growth Distribution) 27% ¹22E-¹23E Diagnostics Biotech 4.4X Average Revenue Growth Rates (%) 2023E Diagnostics Biotech 29% '22E - ¹23E Insurtech (2) Average Enterprise Value / Revenue Multiples 3.0x 105% 2023E Insurtech (2) $24E-¹25E FOXO 1.0x 2024E FOXO 29% '22E - ¹23E High Growth Distribution (¹) 6.3x 2023E High Growth Distribution) 28% ¹23E-¹24E Diagnostics Biotech 3.6x 2024E Diagnostics Biotech 22% '23E - 24E Insurtech (2) 1.7x 2024E Insurtech (2) Source: Company filings, investor presentations, FactSet, and SNL Market data as of 02/18/2022. Note: This slide 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. (1) High Growth Distribution based on 2022E-2023E metrics due to lack of sufficient analyst estimates beyond 2023. (2) HSCM Public InsurTech Index comprised of BHG, BRP, CCCS, CLOV, DOMA, DCT, ESNT, EVER, GOCO, GSHD, GWRE, HIPO, KNSL, LMND, MAX, MILE, OSCR, PLMR, QNST, ROOT, SLQT, and TRUP.#40Thank you For further information, please contact Jon Sabes CEO & Founder [email protected] fift FOXO Life insurance designed to keep you alive™ Ⓒ2022 FOXO Technologies Inc. All rights reserved.