DEF 14A of Oscar Health, Inc., Apr 25, 2024

DEF 14A of Oscar Health, Inc.

Filed Apr 25, 2024 · FY20230001140361-24-021911

Open on EDGAR

  1. Melissa Curtin

    | Compensation Committee Report | 45 | | Executive Compensation Tables | 46 | | Summary Compensation Table | 46 | | Grants of Plan-Based Awards in Fiscal 2023 | 47 | | Summary of Executive Compensation Arrangements | 48 | | Outstanding Equity Awards at Fiscal Year-End Table | 50 | | Option Exercises and Stock Vested in Fiscal 2023 | 52 | | Potential Payments Upon Termination or Change in Control | 52 | | CEO Pay Ratio | 57 | | Pay Versus Performance | 58 | | 2023 Director Compensation | 62 | | Compensation Risk Assessment | 65 | | Equity Compensation Plan Information | 66 | | Security Ownership of Certain Beneficial Owners and Management | 70 | | Certain Relationships and Related Person Transactions | 73 | | Policies and Procedures for Related Person Transactions | 73 | | +O Transaction with Sanford Health | 73 | | Issuance and Sale of 7.25% Convertible Senior Notes due 2031 | 73 | | Amended and Restated Investors’ Rights Agreement | 74 | | Alphabet Agreements | 74 | | Director and Officer Indemnification and Insurance | 74 | | Stockholders’ Proposals | 75 | | Other Matters | 76 | | Solicitation of Proxies | 76 | | Oscar’s Annual Report on Form 10-K | 77 |

  2. Proposal 1: Election of Directors

    Proposal 1: Election of Directors At the Annual Meeting, ten directors are to be elected to hold office until the Annual Meeting of Stockholders to be held in 2025 and until each such director’s respective successor is elected and qualified or until each such director’s earlier death, resignation, or removal. We currently have ten directors on our Board of Directors. Our current directors, who are also our director nominees for election at the Annual Meeting, are Mark T. Bertolini, Jeffery H. Boyd, William Gassen III, Joshua Kushner, Laura Lang, David Plouffe, Elbert O. Robinson, Jr., Siddhartha Sankaran, Mario Schlosser, and Vanessa A. Wittman. The Board has nominated each of the foregoing director candidates to serve as directors until the 2025 Annual Meeting. In accordance with our Amended and Restated Certificate of Incorporation and Amended and Restated Bylaws, all director nominees will stand for election for one-year terms that expire at the following year’s annual meeting. Our Amended and Restated Certificate of Incorporation and Amended and Restated Bylaws provide that the authorized number of directors may be changed only by resolution of the Board of Directors, subject to the rights of holders of any series of preferred stock. Subject to the rights of the holders of any series of preferred stock then outstanding in respect of preferred stock directors, any director may be removed with or without cause only by an affirmative vote of at least two-thirds of the voting power of all the outstanding shares of stock entitled to vote generally in the election of directors. If you submit a proxy but do not indicate any voting instructions, the persons named as proxies will vote the shares of common stock represented thereby for the election as directors of the persons whose names and biographies appear below. In the event that any of Mr. Bertolini, Mr. Boyd, Mr. Gassen, Mr. Kushner, Ms. Lang, Mr. Plouffe, Mr. Robinson, Mr. Sankaran, Mr. Schlosser, or Ms. Wittman should become unable to serve, or for good cause will not serve, as a director, it is intended that votes will be cast for a substitute nominee designated by the Board of Directors or the Board may elect to reduce its size. The Board of Directors has no reason to believe that any of the director nominees will be unable to serve if elected. Each of the director nominees has consented to being named in this proxy statement and to serve if elected.

  3. Recommendation of the Board of Directors

    Recommendation of the Board of Directors The Board of Directors unanimously recommends a vote FOR the election of each of the below director nominees.

  4. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 9 | 2024 Proxy Statement |

  5. Recommendation of the Board of Directors

    The current members of the Board of Directors who are also nominees for election to the Board of Directors are as follows:

  6. Recommendation of the Board of Directors

    | Name | Age | Served as a Director Since | Position with Oscar | | Mark T. Bertolini | 67 | 2023 | Chief Executive Officer and Director | | Mario Schlosser | 45 | 2012 | Co-Founder, President of Technology & Chief Technology Officer and Director | | Joshua Kushner | 38 | 2012 | Co-Founder, Vice Chair of the Board and Director | | Jeffery H. Boyd | 67 | 2021 | Chair of the Board | | Siddhartha Sankaran | 46 | 2021 | Director | | William Gassen III | 43 | 2022 | Director | | Laura Lang | 68 | 2022 | Director | | David Plouffe | 56 | 2021 | Director | | Elbert O. Robinson, Jr. | 47 | 2021 | Director | | Vanessa A. Wittman | 57 | 2021 | Director |

  7. Recommendation of the Board of Directors

    The principal occupations and business experience, for at least the past five years, of each director nominee for election at the Annual Meeting are as follows:

  8. Recommendation of the Board of Directors

    | Mark T. Bertolini | Mark T. Bertolini has served as our Chief Executive Officer and as a member of our Board of Directors since April 2023. Mr. Bertolini served as Co-Chief Executive Officer of Bridgewater Associates, LP (“Bridgewater”), a global investment management firm, from January 2022 to March 2023, and previously served as CEO of Aetna Inc., a managed health care company, from November 2010 to November 2018 and as Chairman of Aetna from April 2011 to November 2018. Before joining Aetna, Mr. Bertolini gained extensive experience across the healthcare industry in various executive roles at The Cigna Group, NYLCare Health Plans, and SelectCare, Inc. Mr. Bertolini serves as a director of Verizon Communications Inc., Thrive Global, and the FIDELCO Guide Dog Foundation, and previously served as a director of CVS Health Corporation from 2018 to 2020. Mr. Bertolini holds a Bachelor of Science degree in Business from Wayne State University and a Master of Business Administration from Cornell University. We believe Mr. Bertolini’s extensive executive leadership, tech-forward thinking, and deep healthcare experience make him particularly qualified to serve as a member of our Board of Directors. |

  9. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 10 | 2024 Proxy Statement |

  10. Recommendation of the Board of Directors

    | Mario Schlosser | Mario Schlosser co-founded Oscar in October 2012, and has served as President of Technology since April 2023 and was additionally appointed as Chief Technology Officer in August 2023. Mr. Schlosser has also served as a Director since December 2012. Previously, Mr. Schlosser served as Chief Executive Officer from December 2012 to April 2023, leading the company from inception to serving over one million numbers across Individual & Family and Small Group health plans. In his current officer role, Mr. Schlosser leads product and engineering, data science and cybersecurity, with a focus on building Oscar’s technology platform for the future and continuing to set the strategy for +Oscar. Prior to Oscar, Mr. Schlosser co-founded Vostu, Ltd., a social gaming company in Latin America, where he led the company’s analytics and game design practices from August 2006 to November 2012. From August 2007 to March 2010, Mr. Schlosser served as a Senior Investment Associate at Bridgewater Associates, where he developed analytical trading models. Prior to joining Bridgewater Associates, Mr. Schlosser worked as a consultant for McKinsey & Company in Europe, the United States, and Brazil from November 2002 to May 2007. Mr. Schlosser holds a degree in computer science with highest distinction from the University of Hannover and a Master of Business Administration from Harvard Business School. As a visiting scholar at Stanford University, Mr. Schlosser wrote and co-authored 10 computer science publications. We believe Mr. Schlosser’s perspective and experience from serving as a Co-Founder and Chief Executive Officer of various companies, including Oscar, as well as his technical acumen, make him particularly qualified to serve as a member of our Board of Directors. |

  11. Recommendation of the Board of Directors

    | Joshua Kushner | Joshua Kushner co-founded Oscar in October 2012, has served as a member of our Board of Directors since December 2012 and has served as Vice Chair of our Board of Directors since February 2021. Mr. Kushner is the Founder and Chief Executive Officer of Thrive Capital Management, LLC (“Thrive Capital”), a New York-based venture capital firm. Mr. Kushner holds a Bachelor of Arts degree, majoring in Government, from Harvard College, and a Master of Business Administration from Harvard Business School. We believe Mr. Kushner’s experience as an investor in innovative technology companies makes him particularly qualified to serve as a member of our Board of Directors. |

  12. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 11 | 2024 Proxy Statement |

  13. Recommendation of the Board of Directors

    | Jeffery H. Boyd | Jeffery H. Boyd has served as Chair of our Board of Directors since February 2021. Since 2014, Mr. Boyd has served as Managing Director of Compleat Angler Capital, LLC, a strategic investment firm. Previously, Mr. Boyd served as Chief Executive Officer and President of Booking Holdings Inc. (“Booking”, formerly known as The Priceline Group, Inc.), an online travel company, from November 2002 to December 2013, as interim Chief Executive Officer from April 2016 to December 2016, and as Chairman of the Board from 2013 to 2020. Prior to joining Booking, Mr. Boyd served as Executive Vice President, General Counsel, and Secretary of Oxford Health Plans, Inc., a U.S. healthcare company, from 1995 to 1999. Mr. Boyd has served as a member of the board of directors of The Home Depot, Inc. since 2016. Mr. Boyd has also served as a member of the board of directors and lead independent director of Clear Secure, Inc. since September 2021. Mr. Boyd holds a Bachelor of Arts degree from St. Lawrence University, majoring in Government, and a Juris Doctor from Cornell Law School. We believe Mr. Boyd’s extensive experience in healthcare, e-commerce, sales, and digital marketing, as well as proven leadership, corporate governance, and strategic management skills, makes him particularly qualified to serve as a member of our Board of Directors. |

  14. Recommendation of the Board of Directors

    | Siddhartha Sankaran | Siddhartha Sankaran has served as a member of our Board of Directors since February 2021. Mr. Sankaran also served as our Chief Financial Officer from March 2019 to March 2021, provided transitional services to Oscar from March 2021 to June 2021 and served as our Interim Chief Financial Officer from December 2022 to September 2023. Mr. Sankaran is currently the Managing Director and Group Chief Financial Officer of FWD Group Holdings Limited since September 2023 after serving as their Senior Advisor from June 2023 to September 2023. Mr. Sankaran has also had a number of executive roles in the insurance industry, including as the Chairman and Chief Executive Officer of SiriusPoint Ltd., a global (re)insurance company, from March 2021 to May 2022. He also served as a member of the board of directors of Third Point Reinsurance Ltd., the predecessor to SiriusPoint, from August 2019 to February 2021, including as its chairman from August 2020 to February 2021. Prior to that, Mr. Sankaran served as Executive Vice President and Chief Financial Officer of American International Group, Inc. (“AIG”), a global insurance company, from February 2016 to December 2018. Mr. Sankaran also served as Executive Vice President and Chief Risk Officer at AIG from November 2010 to February 2016. Prior to AIG, he was a Partner at Oliver Wyman, a global management consultancy. Mr. Sankaran holds a Bachelor of Mathematics degree, majoring in actuarial science, with distinction from the University of Waterloo. We believe Mr. Sankaran’s extensive leadership and financial and risk-management experience makes him particularly qualified to serve as a member of our Board of Directors. |

  15. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 12 | 2024 Proxy Statement |

  16. Recommendation of the Board of Directors

    | William Gassen III | William Gassen III has served as a member of our Board of Directors since December 2022. Mr. Gassen has been the President and Chief Executive Officer of Sanford Health, an integrated health system serving communities across the upper Midwest, since November 2020 and is an ex officio member of Sanford Health’s Board of Trustees. In addition, he previously served in a number of leadership roles for Sanford Health over a ten- year period including Chief Administrative Officer, Chief Human Resources Officer, and Corporate Counsel. Mr. Gassen is a former healthcare litigator and is a current member of the State Bar of South Dakota. Mr. Gassen has served on the board of directors of the American Hospital Association since January 2024 and previously served on the Association's Health Systems Committee. Mr. Gassen holds a Bachelor of Science degree, majoring in criminal justice and religious studies, and a Juris Doctor, both from the University of South Dakota. We believe Mr. Gassen’s healthcare industry experience makes him particularly qualified to serve as a member of our Board of Directors. |

  17. Recommendation of the Board of Directors

    | Laura Lang | Laura Lang has served as a member of our Board of Directors since December 2022. Ms. Lang has served as the Managing Director of Narragansett Ventures, LLC, a strategic advisory firm focused on digital business transformation and growth investing, since January 2014. Since November 2018, Ms. Lang has also served as an adviser to L Catterton. Ms. Lang was the Chief Executive Officer of Time Inc., one of the largest branded media companies in the world, from January 2012 until December 2013. From 2008 until she joined Time Inc. in 2012, Ms. Lang was Chief Executive Officer of Digitas Inc., a global marketing and technology agency and unit of Publicis Groupe S.A. In addition, she headed the company’s pure-play digital agencies, including Razorfish, Big Fuel, Denuo and Phonevalley. Ms. Lang currently serves as a member of the Board of Directors and the Talent and Compensation and Finance committees of V. F. Corporation, an international apparel and footwear company. She also serves on the Board of Directors and the Compensation and Audit Committees of Vroom Inc, an e-commerce auto retailer. She previously served as a member of the Board of Directors of Care.com Inc., Nutrisystem, Inc., and Benchmark Electronics, Inc. Ms. Lang holds a Bachelor of Arts from Tufts University, majoring in political science, and a Master of Business Administration from the Wharton School of the University of Pennsylvania. We believe that Ms. Lang’s extensive financial and executive experience, including on compensation committees, makes her particularly qualified to serve as a member of our Board of Directors. |

  18. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 13 | 2024 Proxy Statement |

  19. Recommendation of the Board of Directors

    | David Plouffe | David Plouffe has served as a member of our Board of Directors since February 2021. Mr. Plouffe served as President, Policy and Advocacy of the Chan Zuckerberg Initiative (“CZI”), a charitable organization established by Priscilla Chan and Facebook founder Mark Zuckerberg, from January 2017 to November 2019. Prior to joining CZI, Mr. Plouffe served as Senior Vice President of Policy and Strategy of Uber Technologies, Inc. (“Uber”), a technology-driven transportation company, from August 2014 to January 2017. Before Uber, Mr. Plouffe served in The White House as Senior Advisor to former U.S. President Barack Obama from January 2011 to January 2013 and as Campaign Manager for President Obama’s historic campaign victory in 2008. Prior to the Obama White House years, Mr. Plouffe managed and served as the strategist in election efforts of U.S. senators, governors, members of congress, and mayors, and served as the Deputy Chief of Staff to the House Democratic leader on Capitol Hill. Mr. Plouffe has served as a member of the board of directors of the Obama Foundation, a nonprofit organization founded by First Lady Michelle Obama and President Barack Obama, since January 2014, and currently serves on the boards of directors of a number of other nonprofit organizations. Mr. Plouffe holds a Bachelor of Arts degree, majoring in Political Science and Government, from the University of Delaware. We believe Mr. Plouffe’s extensive experience in public policy and advocacy makes him particularly qualified to serve as a member of our Board of Directors. |

  20. Recommendation of the Board of Directors

    | Elbert O. Robinson, Jr. | Elbert (“Robbie”) O. Robinson, Jr. has served as a member of our Board of Directors since February 2021. Mr. Robinson is the Co-Founder and Chief Executive Officer of Pendulum Holdings LLC (“Pendulum”), an inclusive and strategic growth investing and advisory platform that seeks to reimagine how great companies are built and who gets to build them, which he founded in September 2019. Prior to founding Pendulum, Mr. Robinson served as a Partner of BDT & MSD Partners a merchant bank he joined in May 2009. Mr. Robinson began his career with Goldman, Sachs & Co., where he spent several years working in various investment, advisory, and financing capacities. Mr. Robinson serves on the boards of a number of nonprofit organizations, including, since December 2022, the Royal Trust Academy. Mr. Robinson holds a Bachelor of Arts degree, majoring in Political Science, from Morehouse College. We believe Mr. Robinson’s extensive leadership and investment experience makes him particularly qualified to serve as a member of our Board of Directors. |

  21. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 14 | 2024 Proxy Statement |

  22. Recommendation of the Board of Directors

    | Vanessa A. Wittman | Vanessa A. Wittman has served as a member of our Board of Directors since February 2021. Ms. Wittman was the Chief Financial Officer of Glossier, Inc. (“Glossier”), an online beauty product company, from April 2019 to April 2022, and served as an Advisor until December 2022. Prior to Glossier, Ms. Wittman served as Chief Financial Officer of Oath Inc., a digital media company, from January 2018 to January 2019. Ms. Wittman served as Chief Financial Officer of Dropbox, Inc., a cloud storage and collaboration company, from February 2015 to October 2016, and as Chief Financial Officer of Motorola Mobility Holdings, Inc., a consumer electronics and telecommunications company, from March 2012 to February 2015. From October 2008 to March 2012, Ms. Wittman served as Executive Vice President and Chief Financial Officer of Marsh & McLennan Companies, a global professional services company. Prior to Marsh & McLennan Companies, Ms. Wittman held a number of other senior finance roles during her career. Ms. Wittman has served on the boards of directors of AIG since March 2023, Booking, including as a member of the Audit Committee, since June 2019, and Impossible Foods Inc., a sustainable foods company, since March 2019. From June 2014 to March 2019, Ms. Wittman was a member of the board of directors of Ulta Beauty, Inc., a cosmetics and beauty supply company. She also served as a member of the board of directors of Sirius XM Holdings Inc., an audio entertainment company, from April 2011 to June 2018. Ms. Wittman holds a Bachelor of Arts degree, majoring in Business Administration, from the University of North Carolina at Chapel Hill, and a Master of Business Administration from the University of Virginia. We believe Ms. Wittman’s extensive financial and executive experience, including as Chief Financial Officer of global technology companies, makes her particularly qualified to serve as a member of our Board of Directors. |

  23. Recommendation of the Board of Directors

    | Oscar Health, Inc. | 15 | 2024 Proxy Statement |

  24. Audit Committee Pre-Approval Policy and Procedures

    | R. Scott Blackley | | | | R. Scott Blackley has served as our Chief Financial Officer since August 2023, where he oversees treasury, actuarial, financial reporting, capital management, internal audit, enterprise risk management, and investor relations. Prior to that, Mr. Blackley served as our Chief Transformation Officer from December 2022 to August 2023, and as our Chief Financial Officer from March 2021 to December 2022. Mr. Blackley previously served as Chief Financial Officer of Capital One Financial Corporation (“Capital One”), a financial services firm, from May 2016 to March 2021. Prior to that, he served as Capital One’s Controller and Principal Accounting Officer from March 2011 to May 2016. Before joining Capital One, Mr. Blackley held various executive positions at Fannie Mae, the U.S. Securities and Exchange Commission, and KPMG, LLP. Mr. Blackley holds a Bachelor of Science degree in Accounting from the University of Utah. |

  25. Audit Committee Pre-Approval Policy and Procedures

    | Ranmali Bopitiya | Ranmali Bopitiya has served as our Chief Legal Officer since January 2022, where she oversees corporate governance, legal, compliance and government affairs. Prior to joining Oscar, Ms. Bopitiya served as the Chief Legal Officer for Everside Health, a national direct primary care provider, leading the legal, compliance and risk management teams from July 2019 to December 2021. Prior to that, Ms. Bopitiya served as the Vice President and General Counsel for Colorado Permanente Medical Group (CPMG), the care delivery provider for Kaiser Permanente Colorado, from November 2016 to June 2019. She also led the legal function of University HealthCare Alliance (UHA) a subsidiary of the Stanford Health Care system, from July 2012 to October 2016. Ms. Bopitiya holds a Bachelor of Arts degree in Biology and Religious Studies from the University of Virginia, a Juris Doctor from Yale Law School, and a Master of Public Health from the Harvard School of Public Health. |

  26. Audit Committee Pre-Approval Policy and Procedures

    | Alessandrea Quane | Alessandrea Quane has served as our Chief Insurance Officer since March 2021. Prior to joining Oscar, Ms. Quane served as Executive Vice President and Chief Risk Officer for AIG from March 2016 to March 2021, as well as Chief Corporate Actuary, Head of Global Actuarial and Value Management from March 2015 to March 2016, and Chief Risk Officer of AIG Property Casualty from June 2013 to March 2015. Ms. Quane held roles of increasing responsibility within the Actuarial and Enterprise Risk Management functions at AIG from July 1996 to June 2013. Prior to her tenure with AIG, Ms. Quane specialized in pricing and research for non-standard auto at Allstate. Ms. Quane has served on the Board of XL Bermuda, Ltd. since January 2022. Ms. Quane is a Fellow of the Casualty Actuarial Society and a member of the American Academy of Actuaries. In addition, Ms. Quane holds a Bachelor of Science degree in Business Administration with a major in Actuarial Science from Drake University. |

  27. Talent and Compensation Committee

    | • | making recommendations to our Board of Directors regarding the compensation of our directors; |

  28. 2023 Compensation Highlights

    | • | CEO Transition. In connection with Mr. Bertolini’s appointment, we granted to Mr. Bertolini 2,866,666 restricted stock units (“RSUs”) which vest based solely on continued service, and 7,453,334 performance-based RSUs (“PSUs”), which vest based both on the achievement of specified stock price performance goals and continuation of employment through a set date. The Talent and Compensation Committee designed Mr. Bertolini’s compensation opportunity to align his interests with those of our stockholders, with a focus on achieving sustained, significant stock price growth and stockholder value. The first of the stock price hurdles was achieved in March of 2024. This achievement demonstrates that shareholder value has begun to be realized as meeting the target required a 54% increase in our stock price from the grant date. The Committee does not intend to grant Mr. Bertolini additional long-term incentive or equity-based compensatory awards prior to calendar year 2026. |

  29. 2023 Compensation Highlights

    | • | Founders Awards Cancellation. In support of reducing the dilutive effects of equity awards granted to Mr. Bertolini in connection with his hiring as Chief Executive Officer and the Company’s annual employee equity awards granted in 2023, on March 28, 2023, the Company’s founders, Mr. Schlosser and Joshua Kushner (our Vice Chair), each forfeited the Founders Award that was granted to him in connection with our initial public offering. The Committee did not make any new grants to Messrs. Schlosser and Kushner in 2023. |

  30. 2023 Compensation Highlights

    | • | Base Salaries and Target Annual Cash Incentive Opportunities. The 2023 base salaries and target bonuses for our NEOs remained at 2022 levels, and Mr. Bertolini, who was hired in 2023, receives the same salary and target bonus opportunity as the other NEOs. Mr. Sankaran only received equity compensation related to his role as the Interim Chief Financial Officer and did not receive an annual base salary or participate in the annual cash incentive plan during 2023. |

  31. 2023 Compensation Highlights

    | • | Annual Cash Incentive Achievement. For 2023, annual cash incentive awards were earned based on the achievement of specified Company financial, operational/strategic, growth/innovation and human capital goals (as outlined later in this CD&A). Our Talent and Compensation Committee approved performance goals for our performance-based annual bonus program that were intended to reward successful execution of our business plan and achievement of our short-term strategic priorities. Based on an assessment of the Company’s strong performance relative to pre-established targets and an overall review of management’s performance, most notably with respect to the outperformance on the Adjusted EBITDA metric, the Talent and Compensation Committee determined to pay out annual bonuses at 135% of target for each of our NEOs (other than Mr. Sankaran, who was not eligible for cash incentives). |

  32. 2023 Compensation Highlights

    | • | Equity-Based Long Term Incentives. We believe that equity-based compensation effectively aligns the interests of our executives with those of our stockholders by directly linking compensation to the value of our common stock. In 2023, Mr. Blackley and Mmes. Quane and Bopitiya were granted a blend of stock options and RSUs. The stock options were intended to align executive and long-term stockholder interests and reward for increases in stockholder value. The stock options and RSUs also have a retentive component as they vest over a four-year period. As noted below, the Company is moving towards an equity program that further ties the achievement of equity compensation to the Company’s long term strategic performance. |

  33. 2023 Compensation Highlights

    | • | InsuranceCo Profitability PSU Achievements. In 2023, we also saw the achievement of PSUs that were granted in 2021 to Mr. Blackley, Ms. Bopitiya and Ms. Quane to incentivize the achievement of InsuranceCo profitability. The PSUs will vest on September 1, 2024, subject to the executive’s continued service through that date. This PSU award helped drive significant financial milestone achievement. |

  34. 2023 Compensation Highlights

    | • | 2024 Long-Term Incentive Program. To retain and to further align the interests of our executives with those of our stockholders, our Talent and Compensation Committee designed a long-term incentive program for 2024 that ties our equity-based long-term incentive award structure to the Company’s long-term strategy. Our 2024 program will be comprised of 50% RSUs and 50% PSUs, driving the executive management team towards shared financial performance objectives. The PSUs cliff vest at the end of a three-year performance period, covering 2024 through 2026, and are tied to the achievement of a cumulative financial performance goal, with a relative total shareholder return modifier. |

  35. Compensation Governance and Best Practices

    | What We Do | | What We Do Not Do | | | • | Emphasize performance-based, at risk compensation. | • | Grant uncapped cash or equity incentives or guaranteed equity compensation. | | • | Emphasize the use of equity compensation to reward long-term value creation and promote executive retention. | • | Provide significant perquisites. | | • | Weight the overall pay mix towards incentive compensation for senior executives. | • | Permit hedging or pledging of our stock. | | • | Engage an independent compensation consultant to advise our Talent and Compensation Committee. | • | Provide single-trigger cash payments or benefits upon a change in control. | | • | Maintain an SEC- and NYSE-compliant clawback policy. | • | Provide any excise tax gross-ups. | | • | Maintain robust stock ownership guidelines for our executives and non-employee directors. | | |

  36. Executive Compensation Objectives and Philosophy

    | • | We believe it is important for our employees to participate in long-term value creation; |

  37. Executive Compensation Objectives and Philosophy

    | • | We aim to retain and reward high-performing employees by awarding them cash and equity incentives as part of their compensation package; |

  38. Executive Compensation Objectives and Philosophy

    | • | Equity awards are sized based on market competitive analysis by job type as well as company performance while also considering potential dilution; and |

  39. Executive Compensation Objectives and Philosophy

    | • | Equity is a long-term incentive granted as a strategic component of compensation to promote retention and alignment with Company goals. |

  40. Role of Compensation Consultant

    Role of Compensation Consultant FW Cook provides executive compensation consulting services to our Talent and Compensation Committee. During 2023, FW Cook provided services related to the review of 2023 compensation levels, awards under our long-term incentive program, the structure and terms of our incentive compensation plans and awards, executive compensation trends and regulatory developments, our compensation peer group, CEO compensation, non-employee director compensation, and assistance with this CD&A, as well as our stock ownership guidelines. FW Cook is retained by and reports to the Talent and Compensation Committee and, at the request of the Talent and Compensation Committee, participates in Committee meetings. FW Cook did not provide any services to the Company in 2023 other than through its engagement by the Talent and Compensation Committee. The Talent and Compensation Committee reviewed the independence of FW Cook under NYSE and SEC rules and concluded that its work has not raised any conflict of interest.

  41. Peer Group

    Peer Group The Talent and Compensation Committee uses a custom peer group that serves as a primary reference point for various compensation analyses, including EVP equity holdings, incentive plan design, aggregate company-wide equity grant practices, and non-employee director compensation. The Committee considers data from the custom peer group alongside multiple surveys when evaluating EVP pay levels. The Company’s custom compensation peer group has evolved substantially from the IPO planning process through 2023, and the rapid rate of change both at the Company and among its peers could continue to evolve the group over time. The Talent and Compensation Committee expects to review the relevance of the peer group on an annual basis and determine if any future modifications are necessary at that time. The peer group reflects a “hybrid” approach intended to reflect the Company’s disruptive business model and talent strategy that straddles the managed care and healthtech industries. In August 2022, we developed the below peer group with FW Cook, which informed the Talent and Compensation Committee’s review of our executive compensation program for fiscal year 2023. We selected the peer group companies based on a combination of relevant factors, including industry classification, business model, and size (including employee count, revenue, and market capitalization).

  42. Peer Group

    | 1Life Healthcare | Alignment Healthcare | Allscripts | Bright Health Group | | Ceridian | Change Healthcare | Clover Health | Concentrix | | eHealth | Evolent Health | GoodRx | HealthEquity | | Molina Healthcare | Oak Street Health | Omnicell | Paylocity | | Premier | R1 RCM | SS&C Technologies | Teladoc Health |

  43. Peer Group

    | Oscar Health, Inc. | 37 | 2024 Proxy Statement |

  44. Peer Group

    In August 2022, when the above peer group was approved, the Company’s projected 2022 revenues exceeded the peer group 75th percentile, while its market cap fell below the 25th percentile. In August 2023, the Talent and Compensation Committee conducted its annual review of the peer group and determined to maintain a hybrid peer group of health insurance and technology-enabled companies, revising the group to better align with the Company’s evolving business strategy and financial profile. In particular, the Committee approved the removal of the following companies from the peer group due to acquisition or differences in business model or financial profile: 1Life Healthcare, Bright Health Group, Ceridian, Change Healthcare, eHealth, Oak Street Health, Paylocity, SS&C Technologies and Veradigm (f/k/a Allscripts). The Committee approved the addition of two comparably-sized healthcare technology companies: Agilon Health and Privia Health. The Committee approved the below peer group, which was developed with FW Cook, to inform our executive compensation program for fiscal year 2024.

  45. Peer Group

    | Agilon Health | Alignment Healthcare | Clover Health | Concentrix | | Evolent Health | GoodRx | HealthEquity | Molina Healthcare | | Omnicell | Premier | Privia Health | R1 RCM | | Teladoc Health | | | |

  46. Peer Group

    In August 2023, when this peer group was approved, the Company’s projected 2023 revenues exceeded the peer group 75th percentile, while its market cap was slightly above the 25th percentile. As of the date of this proxy, the Company’s revenues continue to exceed the peer group 75th percentile, while its market cap is now closer to the median of the peer group.

  47. Elements of Compensation

    | • | Annual Performance-Based Incentive Compensation. Annual performance bonuses promote short-term performance objectives and reward executives for their contributions toward achieving those objectives. |

  48. Elements of Compensation

    | • | Equity Based Long-Term Incentive Compensation. Equity compensation aligns executives’ interests with our stockholders’ interests, emphasizes long-term financial, operational and stock price performance, and helps retain executive talent over the long term. |

  49. Cash Incentive Compensation

    Cash Incentive Compensation Annual Cash Incentive Bonuses We consider annual cash incentive bonuses to be an important component of our total compensation program in incentivizing achievement of our near-term priorities that are expected to drive sustainable long-term stockholder value. Other than Mr. Sankaran, each NEO is eligible to receive an annual performance-based cash bonus based on a specified target annual bonus award amount, expressed as a percentage of the NEO’s base salary. For fiscal year 2023, the target cash bonus for each eligible NEO was 30% of base salary. In future annual incentive cycles, we plan to differentiate the values of executive annual cash incentive bonus targets. The 2023 annual bonuses for the eligible NEOs were determined based on the achievement of company performance goals (the “Company Performance Goals”) that were established at the beginning of 2023 and were aligned with the Company’s financial, operational/strategic, human capital and growth/innovation goals and targets applied to all employees. For each category other than the financial category, the threshold, target, and maximum payouts for our NEOs were 30%, 100% and 130%, respectively, of the applicable target bonus opportunity. For the financial category, there was an additional NEO maximum opportunity of 200% of target for outperformance. This was intended to reflect the criticality of these financial goals in driving sustainable stockholder value.

  50. Cash Incentive Compensation

    | Oscar Health, Inc. | 39 | 2024 Proxy Statement |

  51. Cash Incentive Compensation

    The following table provides additional detail about the Company Performance Goals, including the weight, metric, and our achievement of the goals with respect to our NEOs in 2023:

  52. Cash Incentive Compensation

    | | Weight | Metric | Actual Achievement (as a % of Target) | | Financial | 50% | Adjusted EBITDA of ($125 million)(1) and Direct and Assumed Premiums $6.5B | 160% | | Operational/Strategic | 30% | Goals relating to operational process and infrastructure initiatives | 97% | | Human Capital | 10% | Goals relating to employee retention | 130% | | Growth | 10% | Goals relating to supporting diversity and inclusion as it relates to membership growth; and preparing for expansion | 130% | | Total | 100% | | 135% |

  53. Cash Incentive Compensation

    | 1. | For purposes of determining the achievement of this financial goal, Adjusted EBITDA is defined as net income (loss) for the Company and its consolidated subsidiaries before interest expense, income tax expense (benefit), depreciation and amortization as further adjusted for stock-based compensation and other expenses (income) that are considered unusual or not representative of underlying trends of our business. |

  54. Cash Incentive Compensation

    Our actual Adjusted EBITDA for 2023 was ($45 million) and our actual Direct and Assumed Premiums were $6.6 billion. In considering our achievement of the operational/strategic, human capital and growth goals, the Talent and Compensation Committee determined that we achieved slightly below target on the operational/strategic goals and achieved the maximum goals relating to employee retention, member inclusion and preparing for expansion. Based on the Company’s achievement of the applicable Company Performance Goals and the weighting applied to each of the targets, as noted in the chart above, the Talent and Compensation Committee determined that 135% of the executives’ applicable target bonus opportunity was achieved. The participating executives’ 2023 annual bonuses are set forth in the column entitled “Non-Equity Incentive Plan Compensation” (with respect to the Company Performance Component) in the “Summary Compensation Table” below.

  55. Equity-Based Long-Term Incentive Awards

    Equity-Based Long-Term Incentive Awards We view equity-based compensation as the most critical component of our executive total compensation program, as it aligns the interests of our executive officers with those of our stockholders over the long term, reinforcing our commitment to ensuring a strong linkage between Company performance and pay. Given Oscar’s evolutionary trajectory, we also view equity-based compensation as our most retentive compensation component, intrinsically connecting executives to the Company’s long term strategic objectives. In 2023, we granted equity-based compensation to certain of our NEOs in the form of stock options and/or RSUs, as described below. Our equity-based compensation program for 2023 consisted of an annual equity award program for Mr. Blackley, Ms. Quane and Ms. Bopitiya. These equity-based awards comprised 70% to 84% of Mr. Blackley and Mmes. Quane and Bopitiya’s total direct compensation in 2023. Mr. Bertolini did not participate in our annual equity award program but instead received sign-on equity awards granted in connection with his appointment as our Chief Executive Officer. In addition, Mr. Schlosser (along with Mr. Kushner, our Vice Chair) recommended the forfeiture of the Founders Awards granted to them in connection with our initial public offering.

  56. Equity-Based Long-Term Incentive Awards

    | Oscar Health, Inc. | 40 | 2024 Proxy Statement |

  57. Equity-Based Long-Term Incentive Awards

    2023 Annual Equity Awards In March 2023, the Talent and Compensation Committee approved grants of stock options and RSUs to each of Mr. Blackley, Ms. Bopitiya and Ms. Quane. Mr. Schlosser did not receive an equity award in 2023. The Talent and Compensation Committee approved the following equity awards:

  58. Equity-Based Long-Term Incentive Awards

    | Named Executive Officer | Total Dollar- Denominated Value | Options- Dollar- Denominated Value | Options (#)(1) | RSUs-Dollar- Denominated Value | RSUs (#)(2) | | R. Scott Blackley | $4,112,500 | $1,370,833 | 355,138 | $2,741,667 | 601,243 | | Alessandrea Quane | $3,762,500 | $1,254,167 | 324,914 | $2,508,333 | 550,073 | | Ranmali Bopitiya | $1,800,000 | $600,000 | 155,440 | $1,200,000 | 263,158 |

  59. Equity-Based Long-Term Incentive Awards

    | 1. | The number of shares of Class A common stock subject to the option was determined by dividing the dollar-denominated value of the option by the per share Black Scholes valuation as of the grant date, utilizing the same assumptions that the Company uses in preparation of its financial statements. |

  60. Equity-Based Long-Term Incentive Awards

    | 2. | The number of shares of Class A common stock subject to the RSU award was determined by dividing the dollar-denominated value of the RSU award by the average per share closing price of the Company’s Class A common stock for the 30 consecutive trading days prior to (and including) the date immediately preceding the grant date ($4.56). |

  61. Equity-Based Long-Term Incentive Awards

    Each annual equity award granted in 2023 will vest over a four-year period in sixteen equal quarterly installments beginning on June 1, 2023, subject to the executive’s continued service through the applicable vesting date. Bertolini Awards In connection with his appointment as our Chief Executive Officer in April 2023, the Talent and Compensation Committee approved the grant of 2,866,666 RSUs and 7,453,334 PSUs to Mr. Bertolini. The Talent and Compensation Committee designed Mr. Bertolini’s compensation opportunity to align his interests with those of our stockholders, with a focus on achieving sustained, significant stock price growth and stockholder value. The awards were also designed to be retentive, with both sets of awards having a three-year vesting period. The Company does not intend to grant Mr. Bertolini any additional long-term incentive or equity-based compensatory awards prior to calendar year 2026. The RSU award vests with respect to one-third of the RSUs on each of the first three anniversaries of Mr. Bertolini’s employment start date, subject to his continued employment or service as the Company’s Chief Executive Officer or a member of the Board through the applicable vesting date. The PSU award vests based on both (i) the achievement of pre-determined price per share goals over the period commencing on (and including) the grant date and ending on (and including) the third anniversary of Mr. Bertolini’s employment start date (the “performance period”); and (ii) Mr. Bertolini’s continued employment or service as the Company’s Chief Executive Officer through the end of the performance period. The PSUs will become “earned PSUs” based on the achievement of applicable price per share goals sustained over a 90 consecutive trading-day period, during the three-year performance period, as set forth in the following table. The Talent and Compensation Committee determined the price per share goals during the first quarter of 2023 when the stock closing prices ranged from $2.46 to $5.70 leading up to the announcement of Mr. Bertolini’s appointment. They determined the price-per-share goals listed below were challenging yet achievable given Mr. Bertolini’s expertise and track record of building and scaling companies. Moreover, the

  62. Equity-Based Long-Term Incentive Awards

    | Oscar Health, Inc. | 41 | 2024 Proxy Statement |

  63. Equity-Based Long-Term Incentive Awards

    enterprise value at these sustained price points of $3 billion, $4 billion, and $10 billion, respectively, would create significant stockholder value. This value has begun to be realized as the first of the stock price hurdles was achieved in March of 2024. All earned PSUs as of the last day of the performance period will vest in full, subject to Mr. Bertolini’s continued service as the CEO through such date.

  64. Equity-Based Long-Term Incentive Awards

    | Price Per Share Goals | Number of Earned PSUs | | $11.00 | 2,866,667 | | $16.00 | 2,866,667 | | $39.00 | 1,720,000 |

  65. Equity-Based Long-Term Incentive Awards

    As noted above, the share price is measured by averaging the closing price per share over any 90 consecutive trading-day period during the performance period; however, upon a change in control, the share price will be determined based on the price per share paid by an acquirer (or, as applicable, the implied value per share) in the transaction (the “CIC price”). Any vested PSUs will be paid in shares of the Company’s Class A common stock within 30 days following the earlier to occur of the last day of the performance period and Mr. Bertolini’s separation from service following a change in control event of the Company. As noted above, in March 2024, 2,866,667 PSUs became earned PSUs based on the achievement of the $11.00 price per share goal. Founders Awards Cancellation In support of reducing the dilutive effects of equity awards granted to Mr. Bertolini in connection with his hiring as Chief Executive Officer, and the Company’s annual employee equity awards granted in 2023, the Company’s founders, Mr. Schlosser and Mr. Kushner, each recommended to the Company’s Board of Directors that the Company cancel and terminate the Founders Award that was granted to him in connection with our initial public offering. Mr. Schlosser and Mr. Kushner each entered into an agreement in March 2023 to cancel and terminate their Founders Awards, which consisted of PSUs covering 4,229,853 shares (for Mr. Schlosser) and 2,114,926 shares (for Mr. Kushner) of the Company’s Class A common stock. 2021 PSU Award Achievement We granted PSUs to Mr. Blackley, Ms. Bopitiya and Ms. Quane in 2021 that were designed to incentivize the grantees to achieve profitability of the Company’s insurance business during the fiscal year 2023, and promote retention through cliff vesting on September 1, 2024 for any earned shares. The PSUs were eligible to vest only if we achieved InsuranceCo profitability for calendar year 2023. When approving the PSUs in 2021, the Company primarily assessed profitability based on our achievement of an InsuranceCo Combined Ratio of 100% or less. Following 2021, we had refined our method of assessing InsuranceCo profitability to also include our achievement of a break-even InsuranceCo Adjusted EBITDA, which is an additional metric we referenced when discussing InsuranceCo profitability with our stockholders, and which we believed presents a more complete financial picture of our InsuranceCo business. As such, the Committee believed that it was also appropriate to review our achievement of InsuranceCo Adjusted EBITDA at a level of $20 million or above for 2023 in determining whether the PSUs’ profitability goal was satisfied. Because our InsuranceCo Combined Ratio was 99.5% and we achieved a positive InsuranceCo Adjusted EBITDA of $168.7 million, the PSUs were earned and will vest on September 1, 2024, subject to the executive’s continued service through that date. See Appendix A for further information on InsuranceCo Adjusted EBITDA and InsuranceCo Combined Ratio.

  66. Equity-Based Long-Term Incentive Awards

    | Oscar Health, Inc. | 42 | 2024 Proxy Statement |

  67. Severance and Change in Control Arrangements

    Severance and Change in Control Arrangements We are party to employment agreements with certain of our NEOs, which provide for severance benefits and payments upon certain terminations without cause or resignations for good reason. In addition, certain of the equity awards granted to our NEOs include specialized treatment in connection with a qualifying termination and/or a change in control. Our Talent and Compensation Committee believes that these types of arrangements are necessary to attract and retain executive talent, and are a customary component of executive compensation. In particular, such arrangements can serve to mitigate a potential disincentive for them when they are evaluating a potential acquisition of the Company and can encourage retention through the conclusion of the transaction. The payments and benefits provided under our severance and change in control arrangements are designed to provide these NEOs with treatment that is competitive with market practices. A description of these arrangements, as well as information on the estimated payments and benefits that our NEOs would have been eligible to receive as of December 31, 2023, are set forth in “Potential Payments Upon Termination or Change in Control” below.

  68. Accounting for Share-Based Compensation

    Accounting for Share-Based Compensation We follow Financial Accounting Standard Board Accounting Standards Codification Topic 718, (“ASC Topic 718”), for our share-based compensation awards. ASC Topic 718 requires companies to measure the compensation expense for all share-based payment awards made to employees and directors, including stock options, RSUs and PSUs, based on the grant date fair value of these awards. This calculation is performed for accounting purposes and reported in the compensation tables below, even though our executive officers may never realize any value from their awards. ASC Topic 718 also requires companies to recognize the compensation cost of their share-based compensation awards in their income statements over the period that an executive officer is required to render service in exchange for the option or other award.

  69. “Golden Parachute” Payments

    “Golden Parachute” Payments Sections 280G and 4999 of the Internal Revenue Code provide that certain executive officers and other service providers who are highly compensated or hold significant equity interests may be subject to an excise tax if they receive payments or benefits in connection with a change in control of the Company that exceeds certain prescribed limits, and that we, or a successor, may forfeit a deduction on the amounts subject to this additional tax. We do not provide any tax gross-ups to cover excise taxes under Section 4999 in connection with a change in control.

  70. Summary Compensation Table

    Summary Compensation Table The following table contains information about the compensation earned by each of our NEOs during the fiscal years ended December 31, 2023, December 31, 2022, and December 31, 2021, as well as their positions for 2023.

  71. Summary Compensation Table

    | Name and Principal Position | Year | Salary ($) | Bonus ($) | Stock Awards ($)(1) | Option Awards ($)(1) | Non-Equity Incentive Plan Compensation ($)(2) | All Other Compensation ($)(3) | Total ($) | | Mark Bertolini Chief Executive Officer(4) | 2023 | 450,000 | — | 43,905,864 | — | 182,250 | — | 44,538,114 | | Mario Schlosser President of Technology and Chief Technology Officer, and Former Chief Executive Officer | 2023 | 600,000 | — | —(6) | — | 243,000 | 11,000 | 854,000 | | | 2022 | 495,681 | — | — | — | 147,600 | 9,123 | 652,405 | | | 2021 | 430,000 | 42,480 | 60,161,726 | — | 127,440 | 52,900 | 60,814,546 | | Siddhartha Sankaran(5) Former Interim Chief Financial Officer | 2023 | — | — | — | — | — | — | — | | | 2022 | — | — | 2,141,771 | — | — | — | 2,141,771 | | | 2021 | 125,000 | — | 527 | — | — | 2,500 | 128,027 | | R. Scott Blackley Chief Financial Officer and Former Chief Transformation Officer | 2023 | 600,000 | — | 3,980,228 | 1,370,832 | 243,000 | 6,600 | 6,200,660 | | | 2022 | 600,000 | — | — | — | 147,600 | 2,500 | 750,100 | | | 2021 | 490,625 | 34,944 | 5,249,994 | 1,749,998 | 104,832 | — | 7,630,394 | | Alessandrea Quane Chief Insurance Officer | 2023 | 600,000 | — | 3,641,483 | 1,254,168 | 243,000 | 6,600 | 5,745,251 | | | 2022 | 600,000 | — | — | — | 147,600 | 6,100 | 753,700 | | | 2021 | 500,000 | 35,613 | 5,249,994 | 1,749,998 | 106,840 | 1,450 | 7,643,896 | | Ranmali Bopitiya Chief Legal Officer | 2023 | 600,000 | — | 1,742,105 | 599,998 | 243,000 | 6,600 | 3,191,703 | | | 2022 | 552,272 | 250,000 | — | — | 147,600 | 6,100 | 955,972 |

  72. Summary Compensation Table

    | 1. | Amounts reflect the full grant-date fair value of stock options, RSUs and PSUs granted during the applicable fiscal year computed in accordance with ASC Topic 718, rather than the amounts paid to or realized by the NEO. We provide information regarding the assumptions used to calculate the value of all equity awards made to our NEOs in 2023 in Note 10 to the consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2023. |

  73. Summary Compensation Table

    | 2. | Amounts represent bonuses earned by our NEOs under our 2023 annual bonus program. Please see the description of the annual bonus program under “Cash Incentive Compensation” in the CD&A above. |

  74. Summary Compensation Table

    | 3. | Amounts represent: |

  75. Summary Compensation Table

    | • | Mr. Schlosser received 401(k) matching contributions from the Company of $6,000 and a one-time $5,000 gift payment for his 10-years of tenure as the Chief Executive Officer. |

  76. Summary Compensation Table

    | • | Mr. Blackley and Mmes. Quane and Bopitiya each received 401(k) matching contributions from the Company of $6,600. |

  77. Summary Compensation Table

    | 4. | Mr. Bertolini joined the Company as our Chief Executive Officer on April 3, 2023, and his salary reflects his partial year of service. |

  78. Summary Compensation Table

    | 5. | Mr. Sankaran served as Interim Chief Financial Officer from December 1, 2022 until August 14, 2023. Mr. Sankaran remains a member of the Board of Directors. |

  79. Summary Compensation Table

    | 6. | On March 28, 2023, Mr. Schlosser and the Company mutually agreed to cancel and terminate 4,229,853 shares of performance stock units. |

  80. Summary Compensation Table

    | Oscar Health, Inc. | 46 | 2024 Proxy Statement |

  81. Grants of Plan-Based Awards in Fiscal 2023

    Grants of Plan-Based Awards in Fiscal 2023 The following table provides supplemental information relating to grants of plan-based awards made during fiscal year 2023 to help explain information provided above in our Summary Compensation Table. This table presents information regarding all grants of plan-based awards occurring during fiscal year 2023.

  82. Grants of Plan-Based Awards in Fiscal 2023

    | | | Estimated Possible Payouts Under Non-Equity Incentive Plan Awards(1) | | | Estimated Future Payouts Under Equity Incentive Plan Awards | | | All Other Stock Awards: Number of Shares of Stock or Units (#) | All Other Option Awards: Number of Securities Underlying Options (#) | Exercise or Base Price of Option Awards ($/Sh) | Grant Date Fair Value of Stock and Option Awards ($)(2) | | Name | Grant Date | Threshold ($) | Target ($) | Maximum ($) | Threshold (#) | Target (#) | Maximum (#) | | | | | | Mark Bertolini | — | 40,500 | 135,000 | 222,750 | — | — | — | — | — | — | — | | | 4/3/23 | — | — | — | 2,866,667 | 7,453,334(3) | 7,453,334 | — | — | — | 24,584,535 | | | 4/3/23 | — | — | — | — | — | — | 2,866,666(4) | — | — | 19,321,328 | | Mario Schlosser | — | 54,000 | 180,000 | 297,000 | — | — | — | — | — | — | — | | Siddhartha Sankaran | — | — | — | — | — | — | — | — | — | — | — | | R. Scott Blackley | — | 54,000 | 180,000 | 297,000 | — | — | — | — | — | — | — | | | 3/30/23 | — | — | — | — | — | — | 601,243(5) | — | — | 3,980,228 | | | 3/30/23 | — | — | — | — | — | — | — | 355,138(6) | 6.62 | 1,370,832 | | Alessandrea Quane | — | 54,000 | 180,000 | 297,000 | — | — | — | — | — | — | — | | | 3/30/23 | — | — | — | — | — | — | 550,073(5) | — | — | 3,641,483 | | | 3/30/23 | — | — | — | — | — | — | — | 324,914(6) | 6.62 | 1,254,168 | | Ranmali Bopitiya | — | 54,000 | 180,000 | 297,000 | — | — | — | — | — | — | — | | | 3/30/23 | — | — | — | — | — | — | 263,158(5) | — | — | 1,742,105 | | | 3/30/23 | — | — | — | — | — | — | — | 155,440(6) | 6.62 | 599,998 |

  83. Grants of Plan-Based Awards in Fiscal 2023

    | 1. | Amounts reflect potential payouts pursuant to the Company Performance Goals of our 2023 annual bonus program. Please see the description of the annual bonus program under “Cash Incentive Compensation” in the CD&A above. Mr. Sankaran was not eligible to participate in our 2023 annual bonus program under the terms of his Interim Chief Financial Officer offer letter. |

  84. Grants of Plan-Based Awards in Fiscal 2023

    | 2. | Amounts reflect the full grant-date fair value of equity awards granted during fiscal 2023 computed in accordance with ASC Topic 718, rather than the amounts paid to or realized by the NEO. We provide information regarding the assumptions used to calculate the value of all equity awards made to our NEOs in Note 10 to the consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2023. |

  85. Grants of Plan-Based Awards in Fiscal 2023

    | 3. | The PSUs vest upon the achievement of the price-per-share goals set forth below over the period from April 3, 2023 through April 3, 2026 subject to Mr. Bertolini’s continued employment or service as the Chief Executive Officer through April 3, 2026. |

  86. Grants of Plan-Based Awards in Fiscal 2023

    | Price per Share Goal* | Number of Earned PSUs | | $11.00 | 2,866,667 | | $16.00 | 2,866,667 | | $39.00 | 1,720,000 |

  87. Grants of Plan-Based Awards in Fiscal 2023

    | * Average closing price per share of the Company’s Class A common stock equal to or exceeding the applicable stock price goal, measured over a 90 consecutive trading-day period during the performance period |

  88. Grants of Plan-Based Awards in Fiscal 2023

    | 4. | The RSUs vest in three equal annual installments beginning on April 3, 2024, subject to continued employment or service as the Chief Executive Officer or as a member of the Board of Directors through the applicable vesting date. |

  89. Grants of Plan-Based Awards in Fiscal 2023

    | 5. | The RSUs vest over a four-year period in 16 equal quarterly installments beginning on June 1, 2023, subject to the executive’s continued service. |

  90. Grants of Plan-Based Awards in Fiscal 2023

    | 6. | The options will vest over a four-year period in 16 equal quarterly installments beginning on June 1, 2023, subject to the executive’s continued service. |

  91. Grants of Plan-Based Awards in Fiscal 2023

    | Oscar Health, Inc. | 47 | 2024 Proxy Statement |

  92. Outstanding Equity Awards at Fiscal Year-End Table

    Outstanding Equity Awards at Fiscal Year-End Table The following table summarizes the number of shares of common stock underlying outstanding equity incentive plan awards for each NEO as of December 31, 2023. Awards granted prior to March 2021 were granted under our Amended and Restated 2012 Plan (the “2012 Plan”); awards granted from or after March 2021 were granted under our 2021 Incentive Award Plan (the “2021 Plan”) or, with respect to Mr. Bertolini’s 2023 awards, our 2022 Employment Inducement Incentive Award Plan (the “Inducement Plan”).

  93. Outstanding Equity Awards at Fiscal Year-End Table

    | | | Option Awards | | | | Stock Awards | | | | | Name | Grant Date | Number of Securities Underlying Unexercised Options (#) Exercisable | Number of Securities Underlying Unexercised Options (#) Unexercisable | Option Exercise Price ($) | Option Expiration Date | Number of Shares or Units of Stock That Have Not Vested (#) | Market Value of Shares or Units of Stock That Have Not Vested ($)(1) | Equity Incentive Plan Awards: Number of Unearned Shares, Units or Other Rights That Have Not Vested (#) | Equity Incentive Plan Awards: Market or Payout Value of Unearned Shares, Units or Other Rights That Have Not Vested ($)(1) | | Mark Bertolini | 11/15/2020(2) | 20,000 | — | 12.72 | 11/14/2030 | — | — | — | — | | | 10/5/2021(3) | 268,493 | 103,267 | 16.14 | 10/4/2031 | — | — | — | — | | | 4/3/2023(4) | — | — | — | — | 2,866,666 | 26,229,993 | — | — | | | 4/3/2023(5) | — | — | — | — | — | — | 7,453,334 | $39,061,204 | | Mario Schlosser | 12/7/2015(6) | 555,165 | — | 6.36 | 12/7/2025 | — | — | — | — | | | 12/7/2015(6) | 555,165 | — | 6.36 | 12/7/2025 | — | — | — | — | | | 12/17/2019(6) | 4,400,000 | — | 9.75 | 12/16/2029 | — | — | — | — | | R. Scott Blackley | 12/6/2020(7) | 750,003 | 249,996 | 15.93 | 12/5/2030 | — | — | — | — | | | 12/6/2020(8) | — | — | — | — | 250,000 | 2,287,500 | — | — | | | 8/31/2021(9) | 148,055 | 115,155 | 15.59 | 8/30/2031 | — | — | — | — | | | 8/31/2021(10) | — | — | — | — | 49,110 | 449,356 | — | — | | | 8/31/2021(11) | — | — | — | — | 244,503 | 2,054,202 | — | — | | | 3/30/2023(12) | 66,588 | 288,550 | 6.62 | 3/29/2033 | — | — | — | — | | | 3/30/2023(13) | — | — | — | — | 488,510 | 4,469,866 | — | — | | Siddhartha Sankaran | 3/13/2019(14) | 799,169 | 62,496 | 9.51 | 3/12/2029 | — | — | — | — | | Alessandrea Quane | 12/6/2020(7) | 625,001 | 208,332 | 15.93 | 12/5/2030 | — | — | — | — | | | 12/6/2020(8) | — | — | — | — | 125,000 | 1,143,750 | — | — | | | 8/31/2021(9) | 148,055 | 115,155 | 15.59 | 8/30/2031 | — | — | — | — | | | 8/31/2021(10) | — | — | — | — | 49,110 | 449,356 | — | — | | | 8/31/2021(11) | — | — | — | — | 224,503 | 2,054,202 | — | — | | | 3/30/2023(12) | 60,921 | 263,993 | 6.62 | 3/29/2033 | — | — | — | — | | | 3/30/2023(13) | — | — | — | — | 446,935 | 4,089,455 | — | — | | Ranmali Bopitiya | 12/31/2021(11) | — | — | — | — | 108,932 | 996,727 | — | — | | | 12/31/2021(15) | — | — | — | — | 183,824 | 1,681,989 | — | — | | | 3/30/2023(12) | 29,145 | 126,295 | 6.62 | 3/29/2033 | — | — | — | — | | | 3/30/2023(13) | — | — | — | — | 213,816 | 1,956,416 | — | — |

  94. Outstanding Equity Awards at Fiscal Year-End Table

    | 1. | Amounts are calculated based on multiplying the number of shares shown in the table by the per share closing price of our common stock on |

  95. Outstanding Equity Awards at Fiscal Year-End Table

    December 29, 2023 (i.e., the last trading day of our last completed fiscal year), which was $9.15.

  96. Outstanding Equity Awards at Fiscal Year-End Table

    | 2. | These options are fully vested and are exercisable for shares of Class A common stock. |

  97. Outstanding Equity Awards at Fiscal Year-End Table

    | Oscar Health, Inc. | 50 | 2024 Proxy Statement |

  98. Outstanding Equity Awards at Fiscal Year-End Table

    | 3. | The option vests in equal monthly installments through October 1, 2024, subject to continued service. |

  99. Outstanding Equity Awards at Fiscal Year-End Table

    | 4. | The restricted stock units vest in three equal annual installments beginning on April 3, 2024, subject to continued employment or service as the Chief Executive Officer or as a member of the Board of Directors through the applicable vesting date. |

  100. Outstanding Equity Awards at Fiscal Year-End Table

    | 5. | The performance restricted stock units are earned upon the achievement of the price-per-share goals set forth below over the period from April 3, 2023 through April 3, 2026. To the extent the award is earned, it will vest on April 3, 2026, subject to continued employment or service as the Chief Executive Officer. |

  101. Outstanding Equity Awards at Fiscal Year-End Table

    | Price per Share Goal* | Number of Earned PSUs | | $11.00 | 2,866,667 | | $16.00 | 2,866,667 | | $39.00 | 1,720,000 |

  102. Outstanding Equity Awards at Fiscal Year-End Table

    | * based on any 90 consecutive trading-day period. |

  103. Outstanding Equity Awards at Fiscal Year-End Table

    | 6. | These options are fully vested and are exercisable for shares of Class B common stock. |

  104. Outstanding Equity Awards at Fiscal Year-End Table

    | 7. | 25% of the shares subject to this option vested on the one-year anniversary of the vesting commencement date of December 2, 2020, and 1/48th of the shares subject to this option will vest on each subsequent monthly anniversary of the vesting commencement date, subject to the executive’s continued service. In addition, the option is subject to accelerated vesting provisions contained in the executive’s employment agreement. |

  105. Outstanding Equity Awards at Fiscal Year-End Table

    | 8. | 25% of the RSUs subject to this award will vest on the one-year anniversary of the vesting commencement date of December 5, 2020, and 1/16th of the RSUs will vest on each subsequent quarterly anniversary of the vesting commencement date, subject to the executive’s continued service. In addition, the RSUs are subject to accelerated vesting provisions contained in the executive’s employment agreement. |

  106. Outstanding Equity Awards at Fiscal Year-End Table

    | 9. | 1/16th of the shares subject to these options vest and become exercisable on each quarterly anniversary of the vesting commencement date of September 1, 2021, subject to the executive’s continued service. In addition, the options are subject to accelerated vesting and exercise provisions contained in the executive’s employment agreement. |

  107. Outstanding Equity Awards at Fiscal Year-End Table

    | 10. | 1/16th of the RSUs subject to these awards vest on each quarterly anniversary of the vesting commencement date of September 1, 2021, subject to the executive’s continued service. |

  108. Outstanding Equity Awards at Fiscal Year-End Table

    | 11. | These PSU awards were earned as of December 31, 2023 based on the achievement of InsuranceCo profitability goals, and will vest on September 1, 2024, subject to the executive’s continued service through the vesting date. |

  109. Outstanding Equity Awards at Fiscal Year-End Table

    | 12. | 1/16th of the shares subject to these options vest and become exercisable on each quarterly anniversary of the vesting commencement date of June 1, 2023, subject to the executive’s continued service. In addition, the options are subject to accelerated vesting and exercise provisions contained in the executive’s employment agreement. |

  110. Outstanding Equity Awards at Fiscal Year-End Table

    | 13. | 1/16th of the RSUs subject to these awards vest on each quarterly anniversary of the vesting commencement date of June 1, 2023, subject to the executive’s continued service. In addition, the RSUs are subject to accelerated vesting provisions contained in the executive’s employment agreement. |

  111. Outstanding Equity Awards at Fiscal Year-End Table

    | 14. | These options vest and become exercisable as to 1/48th of the underlying shares on the first day of each month from the vesting commencement date of July 1, 2021 through June 1, 2025, subject to Mr. Sankaran’s continued service on the Company’s board of directors. If his service on the board of directors is terminated without cause, the options will accelerate in full. |

  112. Outstanding Equity Awards at Fiscal Year-End Table

    | 15. | 1/16 of the RSUs subject to this award vest each quarterly anniversary of the vesting commencement date of March 1, 2022, subject to the executive’s continued service. In addition, the RSUs are subject to accelerated vesting provisions contained in the executive’s employment agreement. |

  113. Outstanding Equity Awards at Fiscal Year-End Table

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  114. Option Exercises and Stock Vested in Fiscal 2023

    Option Exercises and Stock Vested in Fiscal 2023 The following table sets forth information regarding the exercise of vested stock options and vesting of stock awards by our NEOs during fiscal year 2023.

  115. Option Exercises and Stock Vested in Fiscal 2023

    | | Option Awards | | Stock Awards | | | Name | Number of Shares Acquired on Exercise (#) | Value Realized on Exercise(1) ($) | Number of Shares Acquired on Vesting (#) | Value Realized on Vesting(2) ($) | | Mark Bertolini | — | — | — | — | | Mario Schlosser | 1,023,799 | 6,446,065 | — | — | | R. Scott Blackley | — | — | 390,796 | 2,769,798 | | Alessandrea Quane | — | — | 256,201 | 1,830,903 | | Ranmali Bopitiya | — | — | 131,041 | 930,431 | | Siddhartha Sankaran | — | — | 683,544 | 4,349,618 |

  116. Option Exercises and Stock Vested in Fiscal 2023

    | 1. | Amounts are calculated by multiplying the number of shares as to which the option was exercised by the market price of the shares on the exercise date, net of the exercise price. |

  117. Option Exercises and Stock Vested in Fiscal 2023

    | 2. | Amounts are calculated by multiplying the number of shares vested by our closing stock price on the vesting date. |

  118. Potential Payments Upon Termination or Change in Control

    Potential Payments Upon Termination or Change in Control

  119. Estimated Potential Payments

    Estimated Potential Payments The following table summarizes the payments that would be made to our NEOs upon the occurrence of certain qualifying terminations of service or a change in control, in any case, occurring on December 31, 2023. Amounts shown do not include (i) accrued but unpaid base salary through the date of termination, or (ii) other benefits earned or accrued by the NEO during his or her employment that are available to all salaried employees, such as accrued vacation.

  120. Estimated Potential Payments

    | Name | Benefit | Termination Without Cause or for Good Reason / Cause (no Change in Control) ($) | Change in Control (no Termination) ($)(1) | Termination Without Cause or for Good Reason /Cause in Connection with a Change in Control ($) | Death/Disability ($) | | Mark Bertolini | Cash(2) | 915,000 | — | 915,000 | — | | | Equity Acceleration(3)(4) | 8,743,328 | — | 26,229,993 | 6,497,774 | | | Continued Health Care(5) | — | — | — | — | | | Total(6) | 9,658,328 | — | 27,144,993 | — | | Mario Schlosser | Cash(2) | 960,000 | — | — | — | | | Equity Acceleration(3) | — | — | — | — | | | Continued Health Care(5) | 31,700 | — | 31,700 | — | | | Total(6) | 991,700 | — | 31,700 | — | | R. Scott Blackley | Cash(2) | 960,000 | — | 960,000 | — | | | Equity Acceleration(3) | — | — | 9,990,956 | — | | | Continued Health Care(6) | 31,700 | — | 31,700 | — | | | Total(6) | 991,700 | — | 10,982,656 | — |

  121. Estimated Potential Payments

    | Oscar Health, Inc. | 55 | 2024 Proxy Statement |

  122. Estimated Potential Payments

    | Name | Benefit | Termination Without Cause or for Good Reason / Cause (no Change in Control) ($) | Change in Control (no Termination) ($)(1) | Termination Without Cause or for Good Reason /Cause in Connection with a Change in Control ($) | Death/Disability ($) | | Alessandrea Quane | Cash(2) | 960,000 | — | 960,000 | — | | | Equity Acceleration(3) | 2,864,313 | — | 8,404,666 | — | | | Continued Health Care(5) | 31,700 | — | 31,700 | — | | | Total(6) | 3,856,013 | — | 9,396,366 | — | | Ranmali Bopitiya | Cash(2) | 960,000 | — | 960,000 | — | | | Equity Acceleration(3) | 1,447,831 | — | 4,954,660 | — | | | Continued Health Care(5) | 31,700 | — | 31,700 | — | | | Total(6) | 2,439,531 | — | 5,946,360 | — |

  123. Estimated Potential Payments

    | 1. | Assumes awards are assumed or substituted in connection with the change in control. |

  124. Estimated Potential Payments

    | 2. | Cash termination payments to our NEOs will be paid in substantially equal installments over the 12-month period following the applicable NEO’s date of termination. |

  125. Estimated Potential Payments

    | 3. | With respect to options, the value of equity acceleration was calculated by (i) multiplying the number of accelerated shares of common stock underlying the options by $9.15, the closing trading price of our common stock on December 29, 2023 (i.e., the last trading day of our last completed fiscal year) and (ii) subtracting the exercise price for the options. With respect to RSUs, the value of equity acceleration was calculated by multiplying the number of accelerated RSUs by $9.15, the closing trading price of our common stock on December 29, 2023 (i.e., the last trading day of our last completed fiscal year). |

  126. Estimated Potential Payments

    | 4. | Mr. Bertolini’s 2023 PSU awards vest upon the achievement of the price-per-share goals based on any 90 consecutive trading-day period. None of the PSUs were earned as of December 31, 2023. |

  127. Estimated Potential Payments

    | 5. | Continued healthcare will be provided each month over the one-year period following the applicable NEO’s date of termination. |

  128. Estimated Potential Payments

    | 6. | Amounts shown represent the maximum potential payment the NEO would have received as of December 31, 2023. Amounts of any reduction pursuant to the 280G best pay provision, if any, would be calculated upon actual termination of employment. |

  129. Termination Payments to Mr. Sankaran

    | b. | The fair values of unvested and outstanding equity awards to our NEOs were remeasured as of the end of each fiscal year, and as of each vesting date, during the years displayed in the table above. Fair values as of each measurement date were determined using valuation assumptions and methodologies (including volatility, dividend yield, and risk-free interest rates) that are generally consistent with those used to estimate fair value at grant in accordance with ASC Topic 718. For stock options, the grant-date fair values were estimated using Black-Scholes. Subsequent valuations at the end of each fiscal year and as of each vest date are performed using a lattice model, as the latter provides a better estimate of options that are no longer at-the-money. The term used to estimate the option fair values under the lattice model in 2023 ranged between 5.2 years to 9.8 years. For market-based restricted stock units, fair values were estimated using a Monte Carlo simulation model, using assumptions that are consistent with those used at grant. For other performance-based awards, the fair values reflect the probable outcome of the performance vesting conditions as of each measurement date. See “Stock Compensation Plans” in the Notes to Consolidated Financial Statements contained in the Company’s Annual Report on Form 10-K for the corresponding fiscal year, where we explain assumptions made in valuing equity awards at grant. |

  130. Relationship Between Compensation Actually Paid and Performance Measures*

    Relationship Between Compensation Actually Paid and Performance Measures*

  131. Relationship Between Compensation Actually Paid and Performance Measures*

    | Oscar Health, Inc. | 60 | 2024 Proxy Statement |

  132. Relationship Between Compensation Actually Paid and Performance Measures*

    | * Note that our CEO’s 2023 values include the grant date fair value (in his SCT Total) and the fair value as of December 31, 2023 (in his CAP) for his April 3, 2023 grant, which was intended to represent the only equity grant he would receive for 2023, 2024, and 2025. |

  133. Director Compensation Program

    Director Compensation Program We maintain a nonemployee director compensation program (the “Director Compensation Program”), which provides for annual retainer fees and long-term equity awards for eligible non-employee directors (“Eligible Directors”). The Director Compensation Program consists of the following components:

  134. Director Compensation Program

    | Cash Compensation | | | Annual Retainer: | $70,000 | | Annual Chairperson Retainer: | $55,000 | | Annual Committee Chair Retainer | | | Audit: | $25,000 (increased to $30,000 effective January 1, 2024) | | Talent and Compensation: | $20,000 | | Nominating and Governance: | $15,000 | | Annual Committee Member (Non-Chair) Retainer | | | Audit: | $10,000 | | Talent and Compensation: | $7,500 | | Nominating and Governance: | $5,000 |

  135. Director Compensation Program

    Annual cash retainers will be paid in quarterly installments in arrears and will be pro-rated for any partial calendar quarter of service. Equity Compensation

  136. Director Compensation Program

    | • | Annual Grant: An Eligible Director who is serving on the board of directors as of the date of the annual meeting of the Company’s stockholders each calendar year will be granted, on such annual meeting date, an RSU award with a value of approximately $175,000 (each, an “Annual Grant”). Each Annual Grant will vest in full on the earlier to occur of (A) the first anniversary of the applicable grant date and (B) the date of the next annual meeting following the grant date, subject to such Eligible Director’s continued service through the applicable vesting date. |

  137. Director Compensation Program

    | • | Initial Grant: Each Eligible Director who is initially elected or appointed to serve on our board of directors will automatically be granted an RSU award with a value equal to the value of the Annual Grant prorated for the portion of the year such Eligible Director is expected to serve (each, an “Initial Grant”). The Initial Grants will vest in full on the earlier to occur of (A) the first anniversary of the applicable grant date and (B) the date of the next annual meeting following the grant date, subject to such Eligible Director’s continued service through the applicable vesting date. |

  138. Director Compensation Program

    In addition, each Initial Grant and Annual Grant will vest in full upon a change in control of our company (as defined in the 2021 Plan). Compensation under our Director Compensation Program will be subject to the annual limits on non-employee director compensation set forth in the 2021 Plan.

  139. Director Compensation Program

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  140. Director Compensation Table

    Director Compensation Table The following table sets forth compensation paid to or earned by our non-employee directors during the year ended December 31, 2023.

  141. Director Compensation Table

    | Name(1) | Fees Earned or Paid in 2023 Cash ($) | Stock Awards ($)(2) | Total ($) | | Jeffery H. Boyd | — | 299,976 | 299,976 | | David Plouffe | 85,000 | 174,993 | 259,993 | | Elbert O. Robinson, Jr. | 84,966 | 174,993 | 259,959 | | Vanessa A. Wittman. | 102,500 | 174,993 | 277,493 | | William Gassen III | 75,000 | 174,993 | 249,993 | | Laura Lang | 90,000 | 174,993 | 264,993 | | Siddhartha Sankaran | — | — | — |

  142. Director Compensation Table

    | 1. | Mark Bertolini, our Chief Executive Officer, Mario Schlosser, our President of Technology and Chief Technology Officer, and Mr. Sankaran, our former Interim Chief Financial Officer, did not receive any compensation for their services as members of our board in 2023; the compensation paid to Messrs. Bertolini, Schlosser, and Sankaran for the services they provided to our Company during 2023 is reflected in the section titled, “Executive Compensation Tables—Summary Compensation Table.” Joshua Kushner, our Vice Chair, is an executive officer (who is not a named executive officer) of the Company and also did not receive any compensation for his service as a member of our board in 2023. |

  143. Director Compensation Table

    | 2. | Amounts reflect the full grant-date fair value of RSU awards and Deferred Stock Unit (DSU) awards granted during 2023 computed in accordance with ASC Topic 718, rather than the amounts paid to or realized by the named individual. We provide information regarding the assumptions used to calculate the value of all RSU awards and DSU awards made to our directors in Note 10 to the consolidated financial statements included in our Annual Report on Form 10-K for the year ended December 31, 2023. |

  144. Director Compensation Table

    The table below shows the aggregate numbers of option awards (exercisable and unexercisable) and unvested stock awards held as of December 31, 2023 by each non-employee director.

  145. Director Compensation Table

    | Name | Option Awards Outstanding at 2023 Fiscal Year End (#) | Unvested Stock Awards Outstanding at 2023 Fiscal Year End (#) | | Jeffery H. Boyd | 693,693 | 19,751 | | David Plouffe | — | 23,918 | | Elbert O. Robinson, Jr. | — | 23,918 | | Vanessa A. Wittman | — | 23,918 | | Siddhartha Sankaran | 861,665 | — | | William Gassen III | — | 19,751 | | Laura Lang | — | 19,751 |

  146. Director Compensation Table

    | Oscar Health, Inc. | 64 | 2024 Proxy Statement |

  147. Director Compensation Table

    Compensation Risk Assessment We have assessed our compensation programs for all employees. We have concluded that our compensation policies and practices do not create risks that are reasonably likely to have a material adverse effect on us. Together with our management, we have also evaluated our executive and employee compensation and benefits programs to determine if these programs’ provisions and operations create undesired or unintentional risk of a material nature. The risk assessment process includes a review of program policies and practices; analysis to identify risks and risk controls related to our compensation programs; and determinations as to the sufficiency of risk identification, the balance of potential risk to potential reward, the effectiveness of our risk controls and the impacts of our compensation programs and their risks to our strategy. Although we periodically review all compensation programs, we focus on the programs with variability of payout, with the ability of a participant to directly affect payout and the controls on participant action and payout. In relation to this, we believe that our incentive compensation arrangements provide incentives that do not encourage risk taking beyond our ability to effectively identify and manage significant risks and are compatible with effective internal controls and our risk management practices. The Talent and Compensation Committee monitors our compensation programs on an annual basis and expects to make modifications as necessary to address any changes in our business or risk profile.

  148. Director Compensation Table

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  149. Director Compensation Table

    Equity Compensation Plan Information The following table provides information as of December 31, 2023, with respect to the shares of the Company’s common stock that may be issued under the Company’s existing compensation plans.

  150. Director Compensation Table

    | Plan Category | Number of Securities to be Issued Upon Exercise of Outstanding Options, Warrants and Rights | Weighted Average Exercise Price of Outstanding Options, Warrants and Rights(2) | Number of Securities Remaining Available for Future Issuance Under Equity Compensation Plans | | Equity compensation plans approved by security holders | 45,837,317(1) | $10.18 | 14,708,089(3) | | Equity compensation plans not approved by security holders | 11,567,936(4) | $6.36 | 5,815,343(5) | | Totals | 57,405,253 | $10.18 | 20,523,432 |

  151. Director Compensation Table

    | 1. | Includes shares subject to outstanding awards granted under our 2021 Plan and 2012 Plan as of December 31, 2023, of which 26,371,446 shares are subject to outstanding options, 1,851,269 shares are subject to outstanding PSUs and 17,614,602 shares are subject to outstanding RSUs. As of December 31, 2023, no rights to purchase our common stock had been granted under the ESPP. |

  152. Director Compensation Table

    | 2. | The weighted average exercise price is calculated based solely on the exercise prices of the outstanding options and does not reflect the shares that will be issued upon the vesting of outstanding PSUs and/or RSUs, which have no exercise price. |

  153. Director Compensation Table

    | 3. | Includes 6,325,153 shares available for future issuance under our 2021 Plan and 8,382,936 shares available for future issuance under our ESPP. No additional awards will be granted under the 2012 Plan and, as a result, no shares remain available for issuance for new awards under the 2012 Plan. |

  154. Director Compensation Table

    | The number of shares available for issuance under the 2021 Plan will be annually increased on January 1 of each calendar year (beginning in 2022 and ending in 2031) by an amount equal to the lesser of (i) a number of shares of Class A common stock and Class B common stock such that the aggregate number of shares available for grant under the 2021 Plan immediately following such increase shall equal 5% of the aggregate number of shares outstanding on the final day of the immediately preceding calendar year, or (ii) such smaller number of shares as is determined by our Board. |

  155. Director Compensation Table

    | The number of shares available for issuance under the ESPP will be annually increased on January 1 of each calendar year (beginning in 2022 and ending in 2031) by an amount equal to the lesser of (i) 1% of the aggregate number of shares of Class A common stock and Class B common stock outstanding on the final day of the immediately preceding calendar year and (ii) such smaller number of shares as is determined by our Board. |

  156. Director Compensation Table

    | 4. | Includes (i) 11,561,270 shares subject to outstanding awards granted under our 2022 Employment Inducement Award Plan as of December 31, 2023 and (ii) 6,666 shares subject to one stock option granted prior to our initial public offering pursuant to individual award agreements not approved by stockholders. The outstanding options were granted to advisors to the Company, are fully vested, have an exercise price of $6.36 per share and will expire no later than December 1, 2025. |

  157. Director Compensation Table

    | 5. | Includes shares available for issuance under our 2022 Employment Inducement Award Plan as of December 31, 2023. |

  158. Medical Loss Ratio

    Medical Loss Ratio Medical Loss Ratio is calculated as set forth in the table below. Direct claims incurred before ceded reinsurance are medical claims, the total medical expenses incurred in order for members to utilize healthcare services, less any member cost sharing. These services include inpatient, outpatient, pharmacy, and physician costs. Direct claims incurred before ceded reinsurance also include risk sharing arrangements with certain of our providers. The impact of the federal risk adjustment program is included in the denominator of our MLR. We believe MLR is an important metric to demonstrate the ratio of our costs to pay for healthcare of our members to net premiums before ceded quota share reinsurance. MLRs in our existing products are subject to various federal and state minimum requirements.

  159. Medical Loss Ratio

    | | Year Ended December 31, | | | (in thousands, except percentages) | 2023 | 2022 | | Direct claims incurred before ceded reinsurance | $4,459,702 | $4,428,000 | | Assumed reinsurance claims | 227,058 | 143,147 | | Excess of loss ceded claims(1) | (3,117) | (18,632) | | State reinsurance(2) | (43,676) | (30,544) | | Net claims before ceded quota share reinsurance(A) | $4,639,967 | $4,521,971 | | Premiums before ceded reinsurance | $5,696,978 | $5,334,520 | | Excess of loss reinsurance premiums(3) | (8,698) | (31,502) | | Net premiums before ceded quota share reinsurance(B) | $5,688,280 | $5,303,018 | | Medical Loss Ratio(A divided by B) | 81.6% | 85.3% |

  160. Medical Loss Ratio

    | 1. | Represents claims ceded to reinsurers pursuant to an excess of loss treaty, for which such reinsurers are financially liable. We use excess of loss reinsurance to limit the losses on individual claims of our members. |

  161. Medical Loss Ratio

    | 2. | Represents payments made by certain state-run reinsurance programs established subject to CMS approval under Section 1332 of the ACA. |

  162. Medical Loss Ratio

    | 3. | Represents excess of loss reinsurance premiums paid. |

  163. Medical Loss Ratio

    | Oscar Health, Inc. | 80 | 2024 Proxy Statement |

  164. InsuranceCo Administrative Expense Ratio

    InsuranceCo Administrative Expense Ratio InsuranceCo Administrative Expense Ratio is calculated as set forth in the table below. The ratio reflects the costs associated with running our insurance companies. We believe InsuranceCo Administrative Expense Ratio is useful to evaluate our ability to manage our expenses as a percentage of net premiums before quota share reinsurance. Expenses necessary to run the insurance companies are included in Other insurance costs and Federal and state assessments. These expenses include variable expenses paid to distribution partners and vendors, premium taxes and healthcare exchange fees, employee-related compensation, benefits, marketing costs, and other administrative expenses.

  165. InsuranceCo Administrative Expense Ratio

    | | Year Ended December 31, | | | (in thousands, except percentages) | 2023 | 2022 | | Other insurance costs | $824,457 | $706,439 | | Impact of quota share reinsurance(1) | (30,454) | 154,741 | | Stock-based compensation expense | (66,060) | (51,495) | | Federal and state assessment of health insurance subsidiaries | 289,647 | 281,049 | | Health insurance subsidiary adjusted administrative expenses(A) | $1,017,590 | $1,090,734 | | Premiums before ceded reinsurance | $5,696,978 | $5,334,520 | | Excess of loss reinsurance premiums | (8,698) | (31,502) | | Net premiums before ceded quota share reinsurance(B) | $5,688,280 | $5,303,018 | | InsuranceCo Administrative Expense Ratio(A divided by B) | 17.9% | 20.6% |

  166. InsuranceCo Administrative Expense Ratio

    | 1. | Includes ceding commissions received from reinsurers, net of the impact of deposit accounting of $(29,451) and $(7,205) for the year ended December 31, 2023 and 2022, respectively. |

  167. InsuranceCo Combined Ratio

    InsuranceCo Combined Ratio InsuranceCo Combined Ratio is defined as the sum of MLR and InsuranceCo Administrative Expense Ratio. We believe this ratio best represents the core performance of the insurance business, prior to the impact of quota share and net investment income.

  168. InsuranceCo Combined Ratio

    | | Year Ended December 31, | | | | 2023 | 2022 | | Medical Loss Ratio | 81.6% | 85.3% | | InsuranceCo Administrative Expense Ratio | 17.9% | 20.6% | | InsuranceCo Combined Ratio | 99.5% | 105.8% |

  169. InsuranceCo Combined Ratio

    | Oscar Health, Inc. | 81 | 2024 Proxy Statement |

  170. Adjusted Administrative Expense Ratio

    Adjusted Administrative Expense Ratio The Adjusted Administrative Expense Ratio is an operating ratio that reflects the Company’s total administrative expenses (“Total Administrative Expenses”), net of non-cash and non-recurring items (as adjusted, “Adjusted Administrative Expenses”), as a percentage of total revenue, excluding the impact of quota share reinsurance premiums less excess of loss reinsurance premiums ceded (“Adjusted Total Revenue”). Total Administrative Expenses are calculated as Total operating expenses, excluding non-administrative insurance-based expenses and the impact of quota share reinsurance. Adjusted Administrative Expenses are Total Administrative Expenses, net of non-cash and non-recurring expense items. We believe Adjusted Administrative Expense Ratio is useful to evaluate our ability to manage our overall administrative expense base. This ratio also provides further clarity into our overall path to profitability.

  171. Adjusted Administrative Expense Ratio

    | | Year Ended December 31, | | | (in thousands, except percentages) | 2023 | 2022 | | Total Operating Expenses | $6,098,484 | $4,553,505 | | Claims incurred, net | (4,642,024) | (3,280,798) | | Premium deficiency reserve (release) | (1,562) | 25,033 | | Impact of quota share reinsurance(1) | (30,454) | 154,741 | | Total Administrative Expenses | $1,424,444 | $1,452,481 | | Stock-based compensation expense | (159,683) | (112,329) | | Depreciation and amortization | (30,694) | (15,283) | | Adjusted Administrative Expenses(A) | $1,234,067 | $1,324,869 | | Total Revenue | $5,862,869 | $3,963,638 | | Reinsurance premiums ceded | 10,909 | 1,463,403 | | Excess of loss reinsurance premiums | (8,698) | (31,502) | | Adjusted Total Revenue(B) | $5,865,080 | $5,395,539 | | Adjusted Administrative Expense Ratio(A divided by B) | 21.0% | 24.6% |

  172. Adjusted Administrative Expense Ratio

    | 1. | Includes ceding commissions received from reinsurers, net of the impact of deposit accounting of $(29,451) and $(7,205) for the year ended December 31, 2023 and 2022, respectively. |

  173. Adjusted EBITDA

    Adjusted EBITDA Adjusted EBITDA is defined as Net loss for the Company and its consolidated subsidiaries before interest expense, income tax expense (benefit), and depreciation and amortization as further adjusted for stock-based compensation, and other items that are considered unusual or not representative of underlying trends of our business, where applicable for the period presented. We present Adjusted EBITDA because we consider it to be an important supplemental measure of our performance and believe it is frequently used by securities analysts, investors, and other interested parties in the evaluation of companies in our industry. Adjusted EBITDA is a non-GAAP measure. Management believes that investors’ understanding of our performance is enhanced by including this non-GAAP financial measure as a reasonable basis for comparing our ongoing results of operations.

  174. Adjusted EBITDA

    | Oscar Health, Inc. | 82 | 2024 Proxy Statement |

  175. Adjusted EBITDA

    We caution investors that amounts presented in accordance with our definition of Adjusted EBITDA may not be comparable to similar measures disclosed by our competitors, because not all companies and analysts calculate Adjusted EBITDA in the same manner. Management uses Adjusted EBITDA:

  176. Adjusted EBITDA

    | • | as a measurement of operating performance because it assists us in comparing the operating performance of our business on a consistent basis, as it removes the impact of items not directly resulting from our core operations; |

  177. Adjusted EBITDA

    | • | for planning purposes, including the preparation of our internal annual operating budget and financial projections; |

  178. Adjusted EBITDA

    | • | to evaluate the performance and effectiveness of our operational strategies; and |

  179. Adjusted EBITDA

    | • | to evaluate our capacity to expand our business. |

  180. Adjusted EBITDA

    By providing this non-GAAP financial measure, together with a reconciliation to the most comparable U.S. GAAP measure, Net loss, we believe we are enhancing investors’ understanding of our business and our results of operations, as well as assisting investors in evaluating how well we are executing our strategic initiatives. Adjusted EBITDA has limitations as an analytical tool, and should not be considered in isolation, or as an alternative to, or a substitute for Net loss or other financial statement data presented in our Consolidated Financial Statements as indicators of financial performance.

  181. Adjusted EBITDA

    | | Year Ended December 31, | | | (in thousands) | 2023 | 2022 | | Net loss | $(270,594) | $(609,552) | | Interest expense | 24,603 | 22,623 | | Other expenses (income) | 7,082 | (2,415) | | Income tax expense (benefit) | 3,294 | (523) | | Depreciation and amortization (“D&A”) | 30,694 | 15,283 | | Stock-based compensation (“SBC”)(1) | 159,683 | 112,329 | | Adjusted EBITDA | $(45,238) | $(462,255) | | General and administrative expenses (excluding SBC and D&A) | $244,085 | $246,735 | | Administrative services revenue | $(15,442) | (61,047) | | Investment income and other revenue (Non-InsuranceCo) | $(14,672) | $(5,711) | | InsuranceCo Adjusted EBITDA(2) | $168,733 | $(282,278) |

  182. Adjusted EBITDA

    | 1. | Represents non-cash expenses related to equity-based compensation programs, which vary from period to period depending on various factors including the timing, number, and the valuation of awards. Year ended December 31, 2023 includes a non-recurring charge of $46.3 million related to accelerated stock-based compensation expense recognized as a result of the cancellation of the Founders Awards previously granted to Mario Schlosser and Joshua Kushner. |

  183. Adjusted EBITDA

    | 2. | We believe that InsuranceCo Adjusted EBITDA provides investors with additional insight into the earnings and capital generation potential of the Company’s insurance subsidiaries. |

  184. Adjusted EBITDA

    | Oscar Health, Inc. | 83 | 2024 Proxy Statement |