P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N1 Progyny Investor Day August 2024

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N2 Forward-Looking Statements This presentation contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. We intend such forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. All statements contained in this presentation other than statements of historical fact, including, without limitation, statements regarding our financial outlook for the third quarter and full year 2024 and beyond as well as our long term targets, including the impact of our sales season and client launches; our anticipated number of clients and covered lives for 2024 and beyond; our positioning to successfully manage economic uncertainty on our business; the timing of client decisions; our expected utilization rates and mix; our ability to retain existing clients and acquire new clients; the expected benefits of our pharmacy program partner agreements; and our business strategy, plans, goals and expectations concerning our market position, future operations, and other financial and operating information. The words “anticipates,” “assumes,” “believe,” “contemplate,” “continues,” “could,” “estimates,” “expects,” “future,” “intends,” “may,” “plans,” “predict,” “potential,” “project,” “seeks,” “should,” “target,” “will,” and the negative of these or similar expressions and phrases are intended to identify forward-looking statements, though not all forward-looking statements use these words or expressions. Forward-looking statements are neither promises nor guarantees, but involve known and unknown risks, uncertainties and other important factors that may cause our actual results, performance or achievements to be materially different from any future results, performance or achievements expressed or implied by the forward-looking statements. These risks include, without limitation, failure to meet our publicly announced guidance, or other expectations about our business; competition in the market in which we operate; our history of operating losses and ability to sustain profitability; unfavorable conditions in our industry or the United States economy; our limited operating history and the difficulty in predicting our future results of operations; our ability to attract and retain clients and increase the adoption of services within our client base; the loss of any of our largest client accounts; changes in the technology industry; changes or developments in the health insurance market; negative publicity in the health benefits industry; lags, failures or security breaches in our computer systems or those of our vendors; a significant change in the level or the mix of utilization of our solutions; our ability to offer high-quality support; positive references from our existing clients; our ability to develop and expand our marketing and sales capabilities; the rate of growth of our future revenue; the accuracy of the estimates and assumptions we use to determine the size of target markets; our ability to successfully manage our growth; reductions in employee benefits spending; seasonal fluctuations in our sales; the adoption of new solutions and services by our clients or members; our ability to innovate and develop new offerings; our ability to adapt and respond to the medical landscape, regulations, client needs, requirements or preferences; our ability to maintain and enhance our brand; our ability to attract and retain members of our management team, key employees, or other qualified personnel; our ability to maintain our Company culture; risks related to any litigation against us; our ability to maintain our Center of Excellence network of healthcare providers; our strategic relationships with and monitoring of third parties; our ability to maintain or any disruption of our pharmacy distribution network or their supply chain; our relationship with key pharmacy program partners or any decline in rebates provided by them; our ability to maintain our relationships with benefits consultants; exposure to credit risk from our members; risks related to government regulation; risks related to potential sales to government entities; our ability to protect our intellectual property rights; risks related to acquisitions, strategic investments, partnerships, or alliances; federal tax reform and changes to our effective tax rate; the imposition of state and local taxes; our ability to utilize a significant portion of our net operating loss or research tax credit carryforwards; our ability to maintain effective internal control over financial reporting; our ability to adapt and respond to the changing SEC expectations regarding environmental, social and governance practices. For a detailed discussion of these and other risk factors, please refer to our filings with the Securities and Exchange Commission (the “SEC”), including in the section entitled “Risk Factors” in our Annual Report on Form 10-K for the fiscal year ended December 31, 2023, and subsequent reports, including our Quarterly Reports on Form 10-Q, that we file with the SEC which are available at http://investors.progyny.com and on the SEC’s website at https://www.sec.gov. Forward-looking statements represent our management’s beliefs and assumptions only as of the date of our August 6, 2024 press release. Our actual future results could differ materially from what we expect. Except as required by law, we assume no obligation to update these forward- looking statements publicly, or to update the reasons. Non-GAAP Financial Measures Adjusted EBITDA, Adjusted EBITDA margin and Adjusted EBITDA margin on incremental revenue are supplemental financial measures that are not required by, or presented in accordance with, GAAP. We believe that these non-GAAP measures, when taken together with our GAAP financial results, provides meaningful supplemental information regarding our operating performance and facilitates internal comparisons of our historical operating performance on a more consistent basis by excluding certain items that may not be indicative of our business, results of operations or outlook. In particular, we believe that the use of Adjusted EBITDA, Adjusted EBITDA margin and Adjusted EBITDA margin on incremental revenue are helpful to our investors as they are measures used by management in assessing the health of our business, determining incentive compensation, evaluating our operating performance, and for internal planning and forecasting purposes. Adjusted EBITDA, Adjusted EBITDA margin and Adjusted EBITDA margin on incremental revenue are presented for supplemental informational purposes only, have limitations as analytical tools and should not be considered in isolation or as a substitute for financial information presented in accordance with GAAP. Some of the limitations of Adjusted EBITDA, Adjusted EBITDA margin and Adjusted EBITDA margin on incremental revenue include: (1) it does not properly reflect capital commitments to be paid in the future; (2) although depreciation and amortization are non-cash charges, the underlying assets may need to be replaced and Adjusted EBITDA does not reflect these capital expenditures; (3) it does not consider the impact of stock-based compensation expense; (4) it does not reflect other non-operating income and expenses, including other (income) expense, net and interest (income) expense, net; (5) it does not reflect tax payments that may represent a reduction in cash available to us. In addition, our non-GAAP measures may not be comparable to similarly titled measures of other companies because they may not calculate such measures in the same manner as we calculate these measures, limiting their usefulness as comparative measures. Because of these limitations, when evaluating our performance, you should consider Adjusted EBITDA, Adjusted EBITDA margin and Adjusted EBITDA margin on incremental revenue alongside other financial performance measures, including our net income, gross margin, and our other GAAP results. We calculate Adjusted EBITDA as net income, adjusted to exclude depreciation and amortization; stock-based compensation expense; other income, net; interest income, net; and provision (benefit) for income taxes. We calculate Adjusted EBITDA margin as Adjusted EBITDA divided by revenue. We calculate Adjusted EBITDA margin on incremental revenue as incremental Adjusted EBITDA in 2023 divided by incremental revenue in 2023. Please see the appendix: “Reconciliation of GAAP to Non-GAAP Financial Measures” elsewhere in this presentation. Safe Harbor Statement

altern Today’s Agenda Investor Day Pete Anevski, CEO Michael Sturmer, President Katie Higgins, Chief Commercial Officer 9:00am Client Perspectives Panel9:45am Joanna Balogh-Reynolds, VP Product Strategy10:20am Break10:35am Provider Perspectives Panel Dr. Janet Choi, Chief Medical Officer Dr. Catha Fischer, Spring Fertility Lissa Kline, SVP, Member and Provider Services Sam Correll, SVP, Network Management 10:50am Member Perspectives Panel11:10am Mark Livingston, Chief Financial Officer11:35am Q&A11:55am Lunch12:30pm P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N3

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N4 Pete Anevski Chief Executive Officer

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N5 The foundation of our success The relationships we’ve built over years with our clients, members, providers, employees and shareholders

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N6 • Advancing our go-to-market strategy to seize our opportunities • Investing to build a robust pipeline of new products • Our differentiation through our provider network relationships • Delivering superior member experiences to drive value to all of our constituencies • Leveraging our financial strength to deepen our competitive advantages Today’s Themes

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N7 At Progyny, we believe in a world where everyone can realize dreams of family and ideal health Progyny is a mission-driven company

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N8 Significant growth over the past 5 years 0 1400 2019 2024E Revenue +5.1x 0.0% 20.0% 2019 2024E Adj. EBITDA Margin +930 bps $1.4B 0 500 2019 Today 0 7000 2019 2024E Clients Covered Lives +4.3x 0 70,000 2019 2024E +4.6x ART Cycles Operational Metrics Financial Metrics 1. As per press release issued on August 6, 2024 2. Reflects midpoint of ranges provided in press release issued on August 6, 2024 2 21 1 2 +5.3x 0 7M 0

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N9 Measuring our impact Since launching our services in 2016, we’ve supported over 300,000 people on their family building journeys 300,000 people would stretch from NY to D.C.

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N10 compounded annual decline in births for women 34 and under since 20101 Societal trends are continuing (1.8%) average age of patient using assisted reproductive technology236.3 compounded annual growth in births for women 35 and over since 201012.2% 8.3% decrease in US birth rates since 20101 10% CAGR increase in the use of ART since 20102

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N11 couples struggle with infertility, up from 1 in 8 five years ago, yet many are left out of existing coverage1 Medical need is increasing 1 in 5 of women of child-bearing age have 2 or more chronic conditions220% excess direct medical expenditures related to menopause attributed to US women aged 45 to 603 $24.8 billion

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N12 of workers say fertility coverage is an important factor when considering where they want to work1 Workplace dynamics are very favorable ~50% of workers would change jobs for better fertility benefits266%+ of employers with at least 500 employees offer some sort of fertility support,3 though it’s limited in many cases More than half

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N13 What has changed since our IPO? • Growing demand has persisted through the pandemic, sustained periods of high inflation, and softening/shifting labor market • Our customer base has become even more diverse, reflecting the universal appeal of our services • Our competitive moat has widened, as the impact of our evidence-based solutions have become even more significant • Increasing opportunities to extend our reach through partnerships, including with health plans • Recognition of women’s health has increased, reflecting higher prevalence and more consequential impacts from deficiencies in traditional care delivery

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N14 … produces sustained, leading clinical outcomes A data-driven approach to plan design and benefit management… … delivers the right care, at the right time, for every member Value-based care personalized to the individual… … yields unique partnership-in-care model Unparalleled level of collaboration across our provider network… Progyny’s core pillars

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N15 Multi-year targets (By 2028) In 2028: • Achieve a revenue CAGR of ~20% • Achieve an Adj. EBITDA CAGR of ~25%$2.4B+ revenue (~2X 20241) $500M+ Adj. EBITDA (2.5x+ 20241) 1. Midpoint of ranges used in calculation as provided in press release issued on August 6, 2024

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N16 • Continue market share growth from large, untapped TAM • Continue expanding our products that address overlooked areas in women’s health • Increase diversification of revenue streams beyond core family building product Strategic Priorities

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N17 Michael Sturmer President

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N18 Delivering the right solution at the right time for each member Concierge support 1:1 and matched to members for their entire journey, paired with robust digital experience Specialized and managed network of the nation’s top fertility and women's health specialists Equitable benefit design that enables coverage and access to evidence-based care and Rx, personal to each member Delivering superior outcomes is in our DNA Data-driven care enabling proactive member outreach, client-level reporting with unique visibility on member outcomes

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N19 I I I I Measuring our impact on individuals and employers 1. Reflects ranges of cash pay rates across the US for an IVF fertility patient without medical coverage, including medication; reflects that the average patient requires more than one round of treatment to achieve a live birth; source: Fertility IQ (here) Out-of-pocket treatment costs to patient Downstream impacts to patient and the employer Progyny’s Impact Average annual Progyny member out-of-pocket cost: ~$1,500 • Fewer treatments needed to achieve a live birth • Lower rates of miscarriages • Reduced stress and anxiety • Fewer higher-risk pregnancies and deliveries • Reduced NICU care costs • Higher productivity Unsupported Fertility Journey Average uninsured patient cost: ~$48,000 to $65,0001 • More treatments needed to achieve a live birth • Higher rates of miscarriages • Heightened stress and anxiety • More high-risk pregnancies and deliveries • Higher NICU care costs • Lost productivity

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N20 Expanding our levers for growth NewExisting N ew Ex is tin g Products M ar ke ts Future diversification Our existing base Upsells of our newest services TAM expansions

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N21 Pathways to expand client relationships NewExisting N ew Ex is tin g Products M ar ke ts Our existing base Upsells of our newest services • Progyny Rx • Adoption and surrogacy • Additional Smart Cycles • Fertility preservation • Donor tissue Expanded Fertility Coverage On average, 20% of Progyny clients have expanded their benefit in some way each year • Pregnancy and Postpartum • Menopause • Global services • New client segments • Additions through M&A Share of Wallet New Populations

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N22 I I I I Gr Expanding market share Greenfield win, expanding the market (clients won who are adding fertility coverage for the first time with Progyny) Brownfield win (clients won who had a previous benefit with a health plan) 2021 - 2023 Selling Seasons +275 clients won 2020 Selling Season +45 clients won 2016 – 2019 Selling Seasons +140 clients won TAM expansions NewExisting Products M ar ke ts Our existing base N ew Ex is tin g

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N23 Growing our addressable market Pre-2021 2022-2023 2024 Future Covered lives 80 million Self-insureds Taft-Hartley (labor) +20 million Federal +6 million 50 plus million Today =106 million Our penetration today + Global 250 - 1000 Employees TAM expansions NewExisting Products M ar ke ts N ew Ex is tin g (ASO, Minimum Premium, Fully Insured)

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N24 Diversification of client base Composition of 2024 Member Base By Industry Continuous Expansion into New Industries Reflects number of industries in our client base 0 20 40 60 2016 2018 2020 2022 2024 Launched in just 2 industries Present in over 45 industries today 1,000 - 2,500 2,501 - 10,000 10,001 - 50,000 50,000+ YE 2017 2024E 1,000 - 2,500 2,501 - 10,000 10,001 - 50,000 50,000+ Distribution of Clients By Size 1. Healthcare 2. Consumer goods 3. Tech 4. Financial services 5. Media/ Entertainment 6. Retail 7. Taft-Hartley (Labor) 8. Manufacturing 9. Pharma/Biotechnology 10. Energy The composition our client base by size is virtually unchanged since 2017 Percent of clients within each tier of covered lives NewExisting Products M ar ke ts Our existing base N ew Ex is tin g Top 10 Industries by Lives: No industry exceeds 18% of base

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N25 Relationships are the foundation of our growth 460+ Clients 6.5M Lives 45+ Industries 99+% retention 8 strategic partnerships +80 NPS Health Plans and PBMS Channel Partners Clinical Partners Clients Our Demonstrated Success

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N26 Katie Higgins Chief Commercial Officer

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N27 At an early stage of penetrating our market opportunity Lives covered by large, self-insured employers Large, self-insured employers Future TAM expansion opportunities Addressable market: 8,000 employers Just 6% of large, self-insured employers are clients today Progyny client today Future opportunity/not yet a Progyny client Addressable market: 106 million lives Just 7% of our addressable lives are Progyny members today Progyny member today Future opportunity/not yet a Progyny client • State and local government populations; 2023 won first federal client • Universities and school systems • Fully-insured/ASO populations • Global populations • Other underserved and underfunded areas of women’s health

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N28 Commercial team covers geographic markets and key buying channels Direct employer selling and expansion Consultant Relations Partnerships Teams of Sales and Client Success Reps covering East, Midwest and West Coast Markets Education and relationship mapping of top consulting influencers Partnership team focused on increasing reseller relationships measuring pipeline and new logo wins

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N29 Understanding benefit consultant ecosystem Negotiating with carriers, PBMs, analyzing workforce health needs, vendor selection and management Consultants leveraged to provide expertise Benefit recommendations and run vendor selections through RFPs or other managed reviews as well as negotiate vendor contracts 65% of deals attached to a consultancy Key sales imperatives to shape buying preferences: 1. Develop trust through credible education with national SMEs on family building 2. Identify and develop trusted relationships with key influencers within national and regional offices 3. Leverage successful shared client success stories to reinforce value propositions well as consultant trust Employer benefit leaders manage the intersection of health care spend and access:

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N30 Partnerships accelerating access to millions of additional lives to serve through: 1. Collaboration through shared growth teams 2. Ease of contracting for employers through existing partnerships 3. Reduction of point solution fatigue Partnerships offer an opportunity to scale growth 30M35M 3.1M 4M+ Potential lives and growing 6M 2M Channel Partners (Potential Lives) Health Plan Partnership Growth Other Partnerships 3M+

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N31 * Represents timeline for clients with 1/1 health plan years Building pipeline and converting into wins January March May July September November C om po ne nt s of se lli ng s ea so n Building Pipeline Progressing Opportunities Peak Commitments Not Nows Carrying Forward Early Commits (Prior Not Nows)

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N32 Majority of non-wins comprised of deferred decisions vs competitive losses Wins Not Nows • Deep experience and data drives accurate projections and guarantees on investment savings and clinical outcomes • Access to curated, actively managed network & dedicated patient care advocates ensure highly supported member experience • Status quo option • Basic dollar cap or cycle- based benefit design • Minimal focus on member experience or outcomes • Shifting priorities including medical rate increases, new innovations such as GLP-1s and chronic condition management can push decision making • Family building and women's health solutions are table stakes for talent VC-Backed Digital Health • Value proposition centered on episodic coaching, navigation and digital content leads to minimal ability to project, control, or guarantee cost or clinical outcomes Deferred Decisions represent majority of Non-Wins; 25% of annual wins attributed to deferred pipeline Reliably win 1M+ new lives annually Default to carrier option Mindshare/Prioritization Competitive Losses represent less than 6% of pipeline

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N33 0-30 Days 30-60 Days 60-90 Days Monitor Member Engagement Streamlined implementation and member experience “ ” There is absolutely nothing I can recommend that would enhance the Progyny implementation experience - it was PERFECT! I wish all vendor/benefit implementations were this easy! “ ” It was truly an exceptional experience. Without question, I would share with other HR colleagues and refer them in the future. Kick-off and Integration Launch Benefit Coordination and Communication Integration Complete & Member Support Launches Progyny Client Progyny Client Go Live

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N34 Robust reporting for a unique level of transparency Quarterly and annual reporting: • Pregnancy and treatment outcomes • Reporting also includes: • Demographics* • Member Activity & Engagement • Clinical Best Practices • IVF & IUI Outcomes • Total Utilization by Therapeutic Class • Quality • Inferred Birth Rate • Network and Utilization & Access* • Pharmacy-Specific Data

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N35 Client Success: The key to driving GTM success and client loyalty Revenue Retention & GrowthClient Satisfaction Client Advocacy 80+ of clients grow spend annually of clients engaged in external advocacy annually The path to parenthood is full of twists and turns, and it looks different for everyone—that’s exactly why we want to help interested employees prepare for it however we can, with a comprehensive and member-centric benefit. ” “ Sonja Kellen, Sr. Dir. Global Health and Wellness at Microsoft Client NPS 99% retention by lives 20% 40+%

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N36 Samantha Elliot Head of US Well-being and Digital Health • Partner since 2024 • $50k prior benefit • Currently pursuing expansion into Menopause Janet Brunk Director Global Benefits Juliet Vestal Corporate VP of Total Rewards Renee Albert Global Benefits Strategy & Experience Leader • Partner since 2024 • No prior fertility benefit • Valued Progyny's vetted, contracted network and outcomes driven approach • Partner since 2021 • $5K prior benefit • 25.4% higher live birth rate, 0 multiples, $545K in cost avoidance • Offering Menopause through Progyny • Long-standing Progyny partner for two leading employer clients • Valued Progyny's high touch model with robust network and equitable plan design Voice of the client: Providing life changing support to employees nationally

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N37 Perspectives from our Clients

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N38 Driving Health Care Innovation Concierge support 1:1 and matched to members for their entire journey, paired with robust digital experience Specialized and managed network of the nation’s top fertility and women's health specialists Equitable benefit design that enables coverage and access to evidence-based care and Rx, personal to each member Delivering superior outcomes is in our DNA Data-driven care enabling proactive member outreach, client-level reporting with unique visibility on member outcomes

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N39 Joanna Balogh-Reynolds VP, Product Strategy

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N40 Designed for the right care, at the right time, for every member Pregnancy & Postpartum Menopause & Midlife Fertility & Family Building Leveraging what we do best: personalized guidance, sophisticated network management, streamlined care coordination and data sharing, and driving cost effective client solution. Preconception and Trying-to-Conceive In-house nurse coaching with diverse experts Expanded network of specialists for women's health Integrated ecosystemClinical expertise Personalized digital experience

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N41 1 in 10 Experience issues such as endometriosis that can take an average of 10 years to diagnose 1993 NIH inclusion policy passes 1977 FDA bans women from research Sources: World Health Organization; https://www.who.int/news/item/04-04-2023-1-in-6-people-globally- affected-by-infertility 2. New York Times: https://www.nytimes.com/2021/09/13/health/women-doctors- infertility.html#:~:text=In%20fact%2C%20a%202016%20survey,rate%20of%20the%20general%20public. 3. NSI, Redefining care for women 2011 Urogynecology recognized as a subspecialty Effective care for conditions that specifically impact women or impact them differently are still emerging.

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N42 Investing in the future of women’s health • Investment in women’s health care reached an all-time high of $3.3 billion in 2022 1 • In 2022, startups focused on women’s health earned 13.26% of health tech funding 2 • For every $1 spent on improving access to family planning services, society yields $120 in benefits 3 • Melinda French Gates says she will donate $1 billion globally over the next two years to help support women and families, including reproductive rights. 4 • Biden-Harris Administration Announces White House Initiative on Women’s Health Research5 1. BCG, Investing in the next generation of Women’s Health | 2. Forbes, Driving a Paradigm Shift in Women’s Health Care | 3. World Economic Forum, Women’s Health: rethinking the cost as an investment for societal gain | 4. NPR, Melinda French Gates to give $1 billion to women’s rights groups | 5 HHS, Biden-Harris Administration Announces $27.5 Million in Funding Opportunities Enhancing Women’s Behavioral Health

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N43 A growing need: Preconception Societal Trends of women of child- bearing age have 2 or more chronic conditions1 20% 1. Commonwealth Fund, Health Care for Women of Reproductive Age| 2. NIH, Can pelvic pain affect my ability to become pregnant? | NICHD - Eunice Kennedy Shriver National Institute of Child Health and Human Development (nih.gov) of women with endometriosis are not able to get pregnant, making this condition one of the top three causes of female infertility2 30% to 50% What Do We Do? Outbound and inbound dedicated coaching at the start of members' conception journey • Nutrition, mental health and lifestyle behaviors • Ovulation and intercourse tracking • Navigating underlying concerns and conditions • Vetted pelvic floor therapy network • Family building process options • Tailored referrals

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N44 A growing need: Conception and Fertility Societal Trends What Do We Do? While overall birth rates are declining sharply, that is being driven by women under 30 who are significantly less likely to struggle with conception Down 12.6% since 2010 birth rates per 1,000 women since 2010 Overall birth rates Birth rates for women ages 35-42 Up 20+% since 2010 • Highly managed network of fertility providers including reproductive urologists • Equitable treatment coverage • Streamlined Rx • Unlimited 1:1 education & emotional support • Partner support • Surrogacy and adoption • Outreach and education timed to critical decision-points A comprehensive and equitable benefit that supports all paths to parenthood

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N45 A growing need: Pregnancy and Postpartum of pregnant women are employed during the year of their pregnancy2 70% pregnancies annually in the US1 5.5 million What Do We Do? Societal Trends What Do We Do? • Timely, programmatic coaching check-ins • Early engagement on health risks • Unlimited Q&A with in- house experts • Doula coaching and vetted network • Robust digital resources, seamlessly available through their Progyny app • Parenting and RTW Support Overcome engagement barriers with a connected experience that members trust over the past 20 years in severe maternal morbidity, a pregnancy complication causing significant maternal harm or risk of death3 Near 200% increase

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N46 A growing need: Menopause What Do We Do? Societal Trends What Do We Do? +20% percent of women in the workforce aged 45 to 541 women entering menopause each year in the United States2 1.3 million 4 years average length of time women are in peri-menopause, though it can last up to 8 years3,4 Progyny addresses the care vacuum – not just hot flashes • Trained, NAMS-certified providers • Education and destigmatization to address the menopause factor • Specialized concierge services • Tailored and personalized digital tools • Preventive referrals for comorbid conditions • Measuring symptom improvement, utilization, engagement, satisfaction and more

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N47 Women and Health A specialized benefits platform created to expedite interventions addressing interconnected health issues that are diagnosed or treated disparately in women. PROGYNY Fertility & Family Building Care Specialized Conditions Ancillary Services Pelvic floor Mental Health Lactation & milk shipping Parenting & Caregiver Support Social Determinants Nutrition & Lifestyle Menstruation PregnancyPCOS Endometriosis Autoimmune CardiacDiabetes Preeclampsia & hypertension Menopause Breast & gynecological cancers Thyroid Preconception Assisted Fertility AdoptionSurrogacy Pregnancy & postpartum Return-to-work Patient education Male infertility Fertility medicationsGenetic testing Weight management Care navigation & access to care Sexual Health Primary/well woman care LGBTQIA+ specific Stress & emotional support

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N48 Expanding adjacent areas of care Addressing unmet needs that: Addressing often overlooked and underserved conditions that impact women and reproductive health disproportionately and differently Lead to costly outcomes when delaying care or not addressing Are under-covered by traditional carriers / are private pay Members don't understand and need support navigating Improve access to high quality care

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N49 Women have a range of care needs Obstetric & Gynecologic conditions PCOS Conditions that affect women differently than men Cardiovascular diseases OsteoporosisObesity Conditions that affect women disproportionally Anxiety & depression Hormonal disruption Autoimmune diseases Gynecologic cancers Endometriosis

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N50 Break

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N51 Perspectives from our Providers

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N52 Perspectives from our Members

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N53 Mark Livingston Chief Financial Officer

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N54 Platform built for growth, profitability, cash flow Consistency of embedded base provides a solid foundation to build upon Scalability for further margin expansion Significant cash flow conversion creates optionality

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N55 Achievements vs previous five-year model IPO Model (view of 2023 from 2019) 2023 Actuals Revenue $1.2B $1.1B Adj. EBITDA $187.6M $187.1M Operating Cash Flow (cumulative 2019 - 2023) $327M $330M Lives 6.5M 5.4M

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N56 Key drivers to our financial model Revenue Profitability High conversion rate to operating cash flow: • Expanding Adjusted EBITDA + low ongoing capital needs • Affords flexibility to invest for growth even as margins and cash flow expand Future considerations: • Cash taxes Cash Flow Gross margin: • Increasing volumes/ scale across clinical footprint • Continuous efficiencies in care management delivery Sales & marketing costs: • High retention, persistent utilization drive efficiencies General & admin costs: • Designed for scalability Growth drivers: • New client lives • Upsells: expanded coverage levels of family building services, additional services • New products

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N57 First year of new cohorts vs full book • Across our largest cohorts, we’ve seen a consistent initial utilization rate in the first year of launching the benefit • The initial (year one) rate of utilization is lower than the blended base due to an inherent ramping period within each client • Utilization for each cohort increases in each successive year following launch For ease of presentation, each year refers to the selling season completed in the prior year (the 2019 cohort reflects the 2018 selling season for launches in 2019, etc.) 0.82% 0.58% 0.67% 0.67% 0.67% 1.09% 0.97% 1.07% 1.03% 1.09% 2019 2020 2021 2022 2023 1.3M 2.2M 2.8M 4.3M 5.4MAnnual Avg. Lives 0.6M 0.8M 0.5M 1.2M 1.2M Newest cohort (first year utilization rate) Newest Cohort (first year lives) Overall utilization rate Utilization rates - New cohorts vs full book

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N58 19 20 21 2220 21 22 2321 22 2322 2323 Utilization growth spanning every cohort Chart reflects female utilization rate blended across full cohort. Year one baseline (index value = 100) Cohort size 1.2M lives0.5M lives0.8M lives0.6M lives Utilization by selling season cohort (indexed utilization from launch year through to 2023) • Since launching in 2016, every annual cohort has experienced increasing utilization over time • Our largest cohorts have seen comparable rates of increase across years 2, 3 and 4 Selling Season 2021202020192018

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N59 0.00% 0.10% 0.20% 0.30% 0.40% 0.50% 0.60% 0.70% Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q4 2019 2020 2021 2022 2023 Covid-related clinic closures Utilization rate ±3 basis points vs. average in any given quarter Q ua rt er ly F em al e U til iz at io n 2024 2

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N60 Key components of revenue estimates • Retrievals are significant medical treatments and day-to-day life/other responsibilities can affect timing for some • Volume of appointments actually scheduled is small beyond 6 weeks out • Medication response varies by patient, may necessitate reschedule Inherent constraints Authorizations Specific treatments which span a defined period. Adjusted lower to allow for cancellations, postponements or other changes based on historical analytics. Claims Actual transactions received which confirm treatment rendered and date of service. Expected Authorizations New Authorizations which are estimated to be received in the future based on current activity and pacing along with historical utilization patterns.

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N61 Visibility into fertility revenue Month 1 Month 2 Month 3 Claims Authorizations Expected Authorizations Start of Quarter

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N62 Visibility into fertility revenue Month 1 Month 2 Month 3 Claims Authorizations Expected Authorizations End of Month 1

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N63 Visibility into fertility revenue Month 1 Month 2 Month 3 Claims Authorizations Expected Authorizations End of Month 2

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N64 Visibility into fertility revenue Month 1 Month 2 Month 3 Claims Authorizations Expected Authorizations End of Month 3

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N65 Historical trend and guidance assumptions 2024 High End Guidance August 6th 2024 Low End Guidance August 6th 2024 High End Guidance May 9th 202320222021 6,1186,1186,1985,3834,3492,812 Average Members* (in 000s) 1.08%1.05%1.08%1.09%1.03%1.07%Female Utilization Rate 66,08764,45667,15458,59644,60030,053Female Unique Utilizers 63,36161,46768,16058,01342,59828,413ART Cycles 0.960.951.010.990.960.95 ART Cycles per Female Unique Utilizer $1,200$1,165$1,270$1,089$787$501Revenue ($ in millions) * Calculations for 2024 exclude 300,000 members from a single client not reflected in female utilizers as a result of the client’s chosen benefit design.

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N66 0.50 0.51 0.53 0.53 0.55 0.55 0.54 0.54 0.56 0.56 0.54 0.54 0.58 0.58 0.53 0.55 0.40 0.45 0.50 0.55 0.60 0.65 Q1 Q2 Q3 Q4 2022 2023 2024 (High-End) 2024 (Low-End) Historical trend: • ART Cycles per Female Unique Utilizer historically steps up from Q1 to Q2 given that a greater proportion of utilizers start their journeys in Q1 and progress to ART in subsequent quarters • Similar sequential step ups typically continue from Q2 thru Q4 for the same reason albeit less pronounced • Given a small step up in Q2 24, and that Q3 data to date suggests a similar level as Q2, current guidance assumes lower than historical levels ART cycles per female unique utilizers quarterly trends and guidance 0.96 0.99 0.95 0.96 2022 2023 2024E (Low-End) 2024E (High-End) Full Year Q1 Q2 Q3 Q4 Q1 Q2 Q3E Q1 Q2Q4E Q3E Q4E

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N67 Demonstrated operating leverage $230 $345 $501 $787 $1,089 $18 $32 $67 $126 $187 8.0% 9.4% 13.5% 16.0% 17.2% 2019 2020 2021 2022 2023 • High rate of client retention • Persistent utilization • Purchasing power given increasing scale • Continuous improvement initiatives across care management delivery • Scalable infrastructure Revenue Adjusted EBITDA Adjusted EBITDA Margin Key drivers of operating leverage:

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N68 Stock-based compensation 2% 4% 7% 13% 11% 11% 10% 7% 6% 6% 2019 2020 2021 2022 2023 2024E 2025E 2026E 2027E 2028E Key drivers of stock- based compensation: • Step up in 2022 reflects a significant grant across a broad base of employees in late 2021 • Staff grants are now RSU based • Step down in 2026 reflects the roll off of expense from the late 2021 grant As a % of revenue

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N69 Sustained growth through multiple levers FY23 FY24 Mid FY28 Target FY25-27 $1.09B $1.18B $2.4B+ • 20% CAGR (’24-’28) yields $2.4B+ in revenue • Covered lives grow to ~11.5M • New products contribute 8-10% of annual revenue in 2028 • Maintain high retention rate Through 2028

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N70 17.2% 17.3% 0.0% 5.0% 10.0% 15.0% 20.0% 25.0% 30.0% 35.0% 40.0% $- $100 $200 $300 $400 $500 $600 $700 FY23 FY24 Mid FY25 FY26 FY27 FY28 Target Adj. EBITDA Adj. EBITDA % Continued expansion in profitability $500M+ • Revenue CAGR of 20% yields Adjusted EBITDA CAGR of 25% • Gross Margins to grow by 400-500 bps* driven by higher new product gross margins while core fertility margins increase slightly • Sales & Marketing costs reflect higher investments in marketing to drive new product growth (additional 100-200 bps*) • General & Administrative costs continue to be leveraged as the Company scales (reduction of 100 bps*) • Given long term Adjusted EBITDA cash conversion rates of ~75%, operating cash flow is estimated to be approaching $400M in 2028 21+% $187M $204M Through 2028 * Basis point changes are expressed on an Adjusted EBITDA basis.

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N71 Strong cash flow enables our strategic capital priorities • Continued evaluation of share repurchases • Expand core business through investments in new products addressing other key life milestones • Investments in go-to-market resources • Create value through disciplined, selective M&A Capital Priorities

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N72 • Advancing our go-to-market strategy to seize our opportunities • Investing to build a robust pipeline of new products • Our differentiation through our provider network relationships • Leveraging our financial strength to deepen our competitive advantages • Delivering superior member experiences to drive value to all of our constituencies Today’s Themes

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N73 Q&A

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N74 Thank you for joining us!

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N75 Appendix: Reconciliation of GAAP to Non-GAAP Financial Measures

P L E A S E R E F E R T O S L I D E 2 F O R T H E S A F E H A R B O R L A N G U A G E R E G A R D I N G T H I S P R E S E N T A T I O N76 Appendix: Reconciliation of GAAP to Non-GAAP Financial Measures