Oscar Health, Inc. ir.hioscar.com News Release Oscar Health Delivers Historic Growth, Issues Guidance for 2022 of More than $6B in Premiums Total enrollment for 2022 tops one million members across the Oscar platform Pro

Oscar Health Delivers Historic Growth, Issues Guidance for 2022 of More than $6B in Premiums

NEW YORK, New York, January 27, 2022 Oscar Health, Inc. ( Oscar or the Company )

(NYSE: OSCR), the first health insurance company built on a full stack technology platform, today issued 2022 guidance reflecting significant growth for its business with premiums expected to increase more than 80% YoY at the midpoint. In

conjunction with guidance, the Company also announced a $305 million convertible notes transaction to strengthen the balance sheet and provide strong liquidity to support the growth of the organization.

Oscar saw historic membership growth at the beginning of 2022, with more than one million members now being served on the Oscar technology platform. The

increased membership is driven largely by growth in the Individual and Small Group lines of business. Additionally, the platform is serving new membership from +Oscar clients. Oscar s growth also reflects strong retention and growth in core

markets during open enrollment, including in Florida, Texas and Georgia, despite having the lowest cost plan in only 5% of its markets.

seen more than 70% annual premium growth, on average, over the past 5 years, demonstrating that our exceptional member experience is resonating with new and existing members alike, said Mario Schlosser, CEO and

co-founder at Oscar. We are honored to welcome our new members and serve the more than one million individuals across the country who are trusting us with their healthcare.

The additional capital supports Oscar s record-high growth and long-term strategy of making a healthier life more accessible and affordable.

Specifically, the Company has agreed to issue and sell, via a private placement, $305 million of 7.25% convertible senior notes due 2031 (the Notes ). The Notes may be converted, subject to certain conditions, at an initial

conversion price of $8.32, which reflects a 38% premium to the price of the Company s Class A common stock (the Class A Common Stock ) as of the close of business on January 26, 2022. Upon conversion, the Notes will be

settled, at the Company s election, in shares of Class A Common Stock, cash, or a combination of cash and shares of Class A Common Stock (subject to certain exceptions). Dragoneer Investment Group has committed to a strategic

investment by agreeing to purchase $250 million of the Notes, in addition to Thrive Capital purchasing $35 million and LionTree and Tenere Capital collectively purchasing $20 million of the Notes (collectively, the

Purchasers ). The Notes have an initial term of ten years, and have a stated maturity of December 31, 2031, subject to earlier conversion, redemption or repurchase in accordance with their terms. Additionally, after the fifth

anniversary of the closing date of the Notes, the initial Purchasers of the Notes will have the right to require the Company to repurchase all of their Notes for cash, subject to certain conditions. The Company may not redeem the Notes prior to

December 31, 2026. The Company may redeem all, but not less than all, of the Notes, at its option, on or after December 31, 2026 and on or before the 35th scheduled trading day immediately preceding the maturity date, for a cash purchase price equal

to the redemption price (as defined in the Indenture), but only if the last reported sale price (as defined in the Indenture) per share of Class A Common Stock exceeds 200% of the conversion price on each of at least 20 trading days (whether or not

consecutive) during the 30 consecutive trading days ending on, and including, the trading day immediately before the date on which the Company sends the redemption notice for such redemption. The Notes transaction is expected to close on or around

February 3, 2022, subject to customary closing conditions. For more information about the terms of the Notes, please refer to our Current Report on Form 8-K filed today.

Centerview Partners LLC is serving as a financial advisor and placement agent to Oscar in connection with

the convertible notes transaction and related matters. In addition, LionTree is serving as a financial advisor to Oscar and is an investor in the convertible notes transaction.

Dragoneer s investment in Oscar further strengthens the relationship between the two companies. We are thrilled to have the opportunity to invest

in Oscar at this stage of their growth journey, said Eric Jones, Partner at Dragoneer. We have immense conviction in this team s ability to manage risk while rapidly growing their member base all of which was developed

through months of diligence with the company. Oscar s consistent share gains in the individual market, across a variety of states and metros, speak to the company s exceptional customer experience, technology, and benefit design. We look

forward to seeing the Oscar team continue to execute against its long-term strategy, further leveraging its technology and driving better outcomes in managed care.

For full year 2022, Oscar projects premiums will increase to $6.1 billion - $6.4 billion, a YoY increase of roughly 80% at the midpoint. The Company is

also projecting an Adjusted EBITDA loss of ($380) million to ($480) million, which reflects both improving MLR and administrative expense ratios YoY. Finally, the Company is introducing a new key performance indicator, the Adjusted Administrative

Expense Ratio, which includes insurance and technology related expenses, as well as other corporate expenses. The Company believes this additional metric provides greater visibility into its overall path to profitability.

Full Year 2022 Outlook

The foregoing statements represent management s current projections as of the date of this release. Actual results may differ materially depending on a

number of factors. Investors are urged to read the Financial Disclosure Advisory and Cautionary Note Regarding Forward-Looking Statements included in this release. Management does not assume any obligation to update these

Oscar is also providing a preliminary view of its full year 2021 results below. Specifically, direct and assumed policy premiums of

$3.44 billion are projected to be at the high end of the guidance range of $3.35 - $3.45 billion. The Medical Loss Ratio is projected to be approximately 89%, at the low end of the range. Net loss is projected to be approximately $(570)

million. The projected 2021 Adjusted EBITDA loss of approximately ($430) million is projected to be better than the Company s ($480) million to ($450) million guidance range. Oscar will report its results for the fourth quarter and year ended

December 31, 2021 after market close on February 10, 2022.

Preliminary Full Year 2021 Key Operating and Non-GAAP Financial Metrics

Conference Call Details

will host a conference call to discuss the information in this release today, January 27, 2022 at 5:00 p.m. (ET). A live audio webcast will be available via the Investor Relations page of Oscar s website at ir.hioscar.com. A replay of the

webcast will be available for on-demand listening shortly after the completion of the call, at the same web link, and will remain available for approximately 90 days.

Non-GAAP Financial Information

This release presents Adjusted EBITDA, a non-GAAP financial metric, which is provided as a complement to the

preliminary results provided in accordance with accounting principles generally accepted in the United States of America ( GAAP ). A reconciliation of Adjusted EBITDA to the most directly comparable GAAP financial measure is provided in

the accompanying tables found at the end of this release.

Financial Disclosure Advisory

The preliminary 2021 financial results discussed in this press release are estimates and represent the most current information available to the Company s

management, as financial closing procedures for the fourth quarter and fiscal year ended December 31, 2021 are not yet complete. Oscar expects that its actual results to be reported in its Annual Report on Form

10-K for the year ended December 31, 2021 will not differ materially from the preliminary results reported in this press release, however, these results are subject to change following the completion of year-end accounting procedures and adjustments, including the execution of the Company s internal control over financial reporting, the completion of the preparation and audit of the Company s financial

statements and the subsequent occurrence or identification of events prior to the formal issuance of the audited financial statements for fiscal 2021.

Forward Looking Statements

This release contains

forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995. All statements other than statements of historical facts contained in this release are forward-looking statements. These statements include, but

are not limited to, statements about our financial outlook and estimates, including direct and assumed policy premiums, medical loss ratio, InsureCo administrative expense ratio, adjusted administrative expense ratio and other financial performance,

and the related underlying assumptions, our business and financial prospects, general and healthcare industry market conditions and trends, our management s plans and objectives for future operations, expectations and business strategy, the

Notes offering described herein, and the benefits of the Notes offering. In some cases, you can identify forward-looking statements by terms such as may, will, should, expects, plans,

anticipates, could, intends, targets, projects, contemplates, believes, estimates, forecasts, predicts, potential or

continue or the negative of these terms or other similar expressions. Accordingly, we caution you that any such forward-looking statements are not guarantees of future performance and are subject to risks, assumptions, and uncertainties

that are difficult to predict and generally beyond our control.

Although we believe that the expectations reflected in these forward-looking statements

are reasonable as of the date made, there are or will be important factors that could cause our actual results to differ materially from those indicated in these forward-looking statements, including, but not limited to, the following: the impact of

COVID-19 on global markets, economic conditions, the healthcare industry and our results of operations, and the response by governments and other third parties; our ability to retain and expand our member

base; our ability to execute our growth strategy; our ability to maintain or enter into new partnerships or collaborations with healthcare industry participants; negative publicity, unfavorable shifts in perception of our digital platform or other

member service channels; our ability to achieve and/or maintain profitability in the future; changes in federal or state laws or regulations, including changes with respect to the Patient Protection and Affordable Care Act and the Health Care and

Education Reconciliation Act of 2010, as amended (collectively, the ACA ) and any regulations enacted thereunder; our ability to accurately estimate our incurred claims expenses or effectively manage our claims costs or related

administrative costs, including as a result of fluctuations in medical utilization rates due to the impact of COVID-19; our ability to comply with ongoing regulatory requirements and applicable performance

standards, including as a result of our participation in government-sponsored programs, such as Medicare; changes or developments in the health insurance markets in the United States, including the passage and implementation of a law to create a

single-payer or government-run health insurance program; our ability to comply with applicable privacy, security, and data laws, regulations, and standards; our ability to maintain key in-network providers and good relations with the physicians, hospitals, and other providers within and outside our provider networks, or to arrange for the delivery of quality care; unfavorable or otherwise costly

outcomes of lawsuits and claims that arise from the extensive laws and regulations to which we are subject; unanticipated results of risk adjustment programs; delays in our receipt of premiums; disruptions or challenges to our relationship with the

Oscar Medical Group; cyber-security breaches of our and our partners information and technology systems; unanticipated changes in population morbidity and large-scale changes in health care utilization; and the other factors set forth under

the caption Risk Factors in our Quarterly Report on Form 10-Q for the quarterly period ended September 30, 2021, filed with the Securities and Exchange Commission ( SEC ), and our

other filings with the SEC.

You are cautioned not to place undue reliance on any forward-looking statements made in this press release.

Any forward-looking statement speaks only as of the date as of which it is made, and, except as otherwise required by law, we do not undertake any obligation to publicly update or review any forward-looking statement, whether as a result of new

information, future developments or otherwise. New factors emerge from time to time, and it is not possible for us to predict which will arise.

Oscar Health, Inc. is the first health insurance company built around a full stack technology platform and a relentless focus on serving its

members. At Oscar, our mission is to make a healthier life accessible and affordable for all. Headquartered in New York City, Oscar has been challenging the healthcare system s status quo since our founding in 2012. The Company s

member-first philosophy and innovative approach to care has earned us the trust of over one million members as of January 2022. We offer Individual & Family, Small Group and Medicare Advantage plans, and +Oscar, our full stack technology

platform to others within the provider and payor space. Our vision is to refactor healthcare to make good care cost less. Refactor is a term used in software engineering that means to improve the design, structure, and implementation of the

software, while preserving its functionality. At Oscar, we take this definition a step further. We improve our members experience by building trust through deep engagement, personalized guidance, and rapid iteration.

For more information, please visit www.hioscar.com.

Dragoneer Investment Group

Dragoneer is a growth-oriented investment firm with over $25 billion in long-duration capital. Dragoneer has a history

of partnering with management teams growing exceptional companies characterized by sustainable differentiation and superior economic models. The firm s track record includes public and private investments across industries and geographies, with

a particular focus on technology-enabled businesses. Dragoneer has been an investor in companies such as Airbnb, Alibaba, Atlassian, AppFolio, Bytedance, Carbon Health, Ceridian, Chime, Datadog, Doordash, Duck Creek, Livongo, Lyra Health, Maven,

PointClickCare, Procore, Slack, Samsara, ServiceTitan, Snowflake, Spotify, Uber, UiPath, and others.

Investor Relations Contact:

VP of Investor Relations

Chief Communications Officer

Key Operating and Non-GAAP Financial Metrics

We regularly review a number of metrics, including the following key operating and non-GAAP financial metrics, to

evaluate our business, measure our performance, identify trends in our business, prepare financial projections, and make strategic decisions. We believe these operational and financial measures are useful in evaluating our performance, in addition

to our financial results prepared in accordance with GAAP.

Members are defined as any individual covered by one of our health plans. We view the number of members enrolled in our health plans as an important metric to

help evaluate and estimate revenue and market share. Additionally, the more members we enroll, the more data we have, which allows us to improve the functionality of our platform.

Direct and Assumed Policy Premiums

Premiums are defined as the premiums collected from our members or from the federal government during the period indicated, before risk adjustment and reinsurance. These premiums include APTC, or premium subsidies, which are available to individuals