📜 What This Document Is 🗓️

This is a Proxy Statement (DEF 14A) for the 2026 Annual Meeting of Stockholders. This document is required by the SEC to give shareholders detailed information about how the company is governed, who the key executives are, and how they were compensated in the past year.

The purpose is twofold: to let shareholders vote on board director nominees and to allow them to vote (on an advisory basis) on the company's Named Executive Officer (NEO) compensation structure. The general theme is governance, focusing heavily on the board’s commitment to oversight and its strategy for future leadership.

👉 The key dates to remember are the Record Date (April 10, 2026) and the Annual Meeting itself (June 4, 2026).

🏢 About Oscar Health, Inc. 🏥

Oscar Health, Inc. operates in the complex world of health insurance, acting as a technology-enabled marketplace. In simple terms, they aim to improve the consumer healthcare experience by leveraging technology to streamline services.

The company's focus is building a "technology-enabled health insurance marketplace" to manage services for members and providers. Their goal is to drive continuous above-market growth and achieve profitability.

👉 The organization uses advanced risk management tools, including those related to AI, to operate within the highly regulated healthcare industry.

📋 Governance and Board Structure Changes 🧑‍⚖️

The Proxy Statement details structural changes occurring at the company's board level, which investors should pay close attention to. The Board plans to reduce its size to eight directors, effective after the Annual Meeting, as director Jeffery Boyd is not standing for reelection.

Furthermore, the Board is implementing a clear leadership shift: Mr. Siddhartha Sankaran, currently a director, has been designated as the independent Chair of the Board, effective after the Annual Meeting.

👉 This signals a strengthening of corporate governance, aiming to reinforce the independence of the board from management and the CEO.

⚖️ Board Committee Oversight & Roles 🗄️

The Board has established three core, standing committees: Audit, Talent and Compensation (T&C), and Nominating and Corporate Governance (N&CG). These committees ensure specialized oversight across the company's most critical risk areas.

• Audit Committee: Chaired by Ms. Vanessa Ames Wittman, this committee oversees financial reporting, internal controls, and major risk areas, including cybersecurity and AI.
• Talent and Compensation Committee (T&C): Chaired by Ms. Laura Lang, this committee is responsible for setting and reviewing the compensation for the CEO and other executives.
• N&CG Committee: Chaired by Jeffery Boyd (until the meeting), this committee focuses on overall corporate governance, recommending board nominees, and overseeing ESG (Environmental, Social, and Governance) matters.

👉 The Board has established a formal structure where all three committees are 100% independent, which reinforces the objective oversight of management.

🧠 Deep Dive: Oversight of Technology Risk 💻

Given that Oscar is a technology company operating in healthcare, the Board dedicates specific attention to technological and external risks. Oversight of cybersecurity and Artificial Intelligence (AI) are central to this commitment.

• Cybersecurity: The Audit Committee oversees cybersecurity risks, reviewing major exposures quarterly. The company uses established global guidelines like ISO 27001 and NIST 800-53 standards to guide its risk management program.
• Artificial Intelligence (AI): The Board oversees AI risks and opportunities, recognizing its potential to improve customer experience and lower costs. The company even established a dedicated AI Governance Committee to ensure safe and responsible use, adhering to best practices and ethical standards.

👉 The formalization of AI oversight shows the company is proactively managing how it uses cutting-edge technology, which is a significant focus for modern health tech firms.

💸 Executive Compensation Review and Plan 💰

The proxy details Oscar’s compensation philosophy, which is "pay-for-performance." The T&C Committee's goal is to ensure executive pay is directly linked to the company’s success and the long-term interest of shareholders.

🎯 2025 Year in Review

The 2025 fiscal year was described as a "reset year" for the individual market, presenting significant headwinds, including a $396.3 million loss from operations. Despite this, the company saw strong operational success:

• Revenue increased 28% year-over-year, reaching $11.7 billion.
• The SG&A expense ratio improved by 160 basis points.

The T&C Committee exercised "downward discretion," awarding an annual incentive payout of 91.0% of target, despite the company achieving 105.9% of its performance goals. This action acknowledged the challenging industry environment.

🚀 2026 Compensation Strategy

For 2026, the long-term incentive plan is set as an equal mix of time-based Restricted Stock Units (RSUs) and Performance Stock Units (PSUs). Crucially, the PSUs are tied to the Company’s Total Shareholder Return (TSR) relative to a peer group (rTSR) and include a cap on payouts if the absolute TSR is negative.

👉 The shift to TSR-based performance metrics is a direct response to shareholder feedback, designed to ensure executive rewards are tied to the overall value delivered to stockholders.

🧑‍💼 Key Management and Board Personnel 🌟

The document provided extensive bios for both the executives and the board nominees, demonstrating the depth of experience guiding the company.

• CEO: Mark T. Bertolini (Director since 2023) brings extensive executive leadership and deep healthcare experience, having served as CEO of Aetna Inc.
• Technology Leader: Mario Schlosser (Co-Founder, President of Technology, CTO) is noted for his technical acumen and experience co-founding the company.
• Finance: Richard Scott Blackley (CFO) brings deep financial expertise, having previously served at Capital One Financial Corporation.
• Insurance/Ops: Janet Liang (President of Oscar Insurance) is a seasoned leader in health plan administration, having previously worked at Kaiser Permanente.
• Legal/Compliance: Adam McAnaney (Chief Legal Officer) brings significant experience in corporate governance and regulatory compliance from large health tech firms.

🔄 Board and Committee Governance Practices ⚙️

The Board emphasizes active governance, which involves continuously reviewing its own composition and the services of its committees. They note that in the last five years, the Board added 3 new directors and 5 directors departed, demonstrating active refreshment.

Regarding director tenure, the Board values having a blend of long-tenured directors (for institutional knowledge) and shorter-tenured directors (for fresh perspectives).

🗣️ Key Calls to Action and Voting Proposals 🗳️

The Proxy Statement outlines the two main decisions shareholders must consider:

1. Election of Directors: Stockholders vote to elect eight director nominees to serve until the 2027 Annual Meeting.
2. "Say-on-Pay" Vote: Shareholders vote (advisory/non-binding) on the compensation of Named Executive Officers for the 2025 fiscal year.

The Board recommends voting FOR both proposals.

📅 Meeting Logistics and Contacts 📞

• Annual Meeting: Thursday, June 4, 2026, at 10:00 a.m. Eastern time.
• Format: The meeting will be completely virtual via live webcast.
• How to Vote: Stockholders can vote online at www.virtualshareholdermeeting.com/OSCR2026.
• Record Date: Stockholders of record at the close of business on April 10, 2026, are entitled to vote.
• Board Contact: Stockholders can send written communication to the Secretary, c/o Secretary, Oscar Health, Inc., 75 Varick Street, 5th Floor, New York, New York 10013.

🧠 The Analogy 🏗️

The relationship between a company's executives and its board is like that of a highly complex cruise ship. The Chief Executive Officer (CEO) is the captain—they operate the ship day-to-day. The Board of Directors acts as the corporate advisory council. This council doesn't steer the ship itself, but they are responsible for making sure the captain has the right tools, the right team around him, and that the overall vessel is seaworthy, profitable, and compliant with all international maritime laws. The proxy statement shows the council doing its annual check-ups (governance, risk, pay) to make sure the ship is ready for the next voyage.

🧩 Final Takeaway ✨

Oscar Health is strategically reinforcing its governance structure and executive leadership to prepare for profitability. The company’s primary message to shareholders is that while the industry is challenging, disciplined operations and a strong focus on technology and robust board oversight will drive future value.