• Carvana for health insurance
• Netflix for health insurance
• Chime for health insurance

• Individual & Family Health Insurance: Provides health coverage directly to individuals and families via Affordable Care Act marketplaces.
• Small Group Health Insurance: Offers health insurance plans to small businesses for their employees.
• Medicare Advantage Plans: Delivers comprehensive health insurance options for eligible seniors and certain disabled individuals.
• +Oscar (Technology Platform): Licenses a full-stack technology platform and services to other healthcare organizations, enabling them to power their own insurance operations and care delivery.

Oscar Health (OSCR) primarily sells health insurance plans to individuals, families, and small businesses, meaning its customer base is predominantly made up of individuals.

The company serves the following categories of customers:

1. Individuals and Families: These are direct consumers who purchase Oscar Health insurance plans for themselves and their dependents. This often occurs through the Affordable Care Act (ACA) marketplaces (health insurance exchanges) or directly from Oscar Health.

2. Employees of Small Businesses: Individuals who receive their health insurance coverage through small group health plans provided by their employers. While the employer is the policyholder, the ultimate beneficiaries and users of the insurance are the employees.

While Oscar Health also has a "C + O" segment that provides technology and administrative services to other companies (such as other health plans or self-insured employers), the overwhelming majority of its covered members and premium revenue come from its individual and small group health insurance offerings.

• UnitedHealth Group (NYSE: UNH)
• CVS Health (NYSE: CVS)

Mark Bertolini Chief Executive Officer

Mark Bertolini assumed the role of CEO of Oscar Health in April 2023. He previously served as the Chairman and CEO of Aetna Inc. from 2011 until its acquisition by CVS Health in 2018 for $69 billion, where he led Aetna's transition into a consumer-oriented healthcare company. Bertolini also served as co-CEO of Bridgewater Associates, a large hedge fund, from January 2022 to May 2023. His career includes executive positions at Cigna, NYLCare Health Plans, and SelectCare, Inc., where he was President and Chief Executive Officer.

R. Scott Blackley Chief Financial Officer

R. Scott Blackley returned to the CFO role at Oscar Health in August 2023, having previously held the position from September 2021 to December 2022. He is responsible for treasury, actuarial, financial reporting, capital management, and investor relations. Before joining Oscar Health in March 2021, Blackley was the Chief Financial Officer of Capital One since May 2016, overseeing its financial management and strategic agenda. His prior experience includes executive roles at Fannie Mae, serving as a Professional Accounting Fellow at the U.S. Securities and Exchange Commission, and being a Partner at KPMG, LLP.

Mario Schlosser Co-Founder & Chief Technology Officer

Mario Schlosser co-founded Oscar Health in 2012 and served as its CEO from inception until April 2023, when he transitioned to President of Technology. In his current role, he leads product and engineering, focusing on developing Oscar's technology platform. Before Oscar Health, Schlosser co-founded the largest social gaming company in Latin America, where he managed analytics and game design. He also worked as a Senior Investment Associate at Bridgewater Associates and as a consultant for McKinsey & Company.

Janet Liang EVP and President of Oscar Insurance

Janet Liang is the Executive Vice President and President of Oscar Insurance, where she oversees all insurance functions for the company.

Jesse Horowitz SVP, Member Experience

Jesse Horowitz joined Oscar Health in 2014 and currently serves as the Senior Vice President of Member Experience. Throughout his tenure, he has held various roles within the company, including positions in Product, Insurance Operations, and Concierge.

The key risks to Oscar Health's (OSCR) business include its ongoing challenges with profitability and cost management, the inherent vulnerability to regulatory and policy changes, and the effective execution of its growth strategy.

1. Profitability and Cost Management

Oscar Health has faced consistent challenges in achieving sustained profitability, having reported only one profitable year since becoming a public company in 2024. The company's financial performance is significantly impacted by its ability to manage medical and administrative costs, as well as its medical loss ratio (MLR). Despite efforts to improve, Oscar Health's net margin remains modestly negative, with investors closely watching for a breakeven-to-positive inflection in profitability by 2026. Inability to effectively manage costs, especially if revenue declines, could harm the company's financial position as many costs are fixed in the short term.

2. Regulatory and Policy Changes

Oscar Health's business model is highly sensitive to changes in healthcare policy and regulation, particularly those related to the Affordable Care Act (ACA). Alterations to ACA subsidies or regulations could negatively impact the company's revenue base and operations. The company must also navigate a complex landscape of state and federal laws, including evolving data privacy regulations such as HIPAA and CCPA, which require substantial resources for compliance. Additionally, increasing capital requirements tied to membership growth and the potential for costly outcomes from lawsuits and investigations pose significant regulatory risks.

3. Execution of Strategy and Growth Management

A critical risk for Oscar Health is its ability to effectively execute its strategic initiatives and manage growth. This includes expanding into new markets and lines of business, as well as successfully monetizing its technology platform through +Oscar. Failure to acquire and retain new members, the underperformance of new business lines or insurance products, or delays in achieving timely profitability in these ventures could result in financial or reputational harm. The success of its strategy hinges on disciplined execution, including pricing, provider networks, engagement, and risk-adjustment execution.

• Entry and Expansion of Large Technology Companies into Healthcare Services and Integrated Platforms: Companies such as Amazon, with their acquisitions (e.g., One Medical) and initiatives (e.g., Amazon Pharmacy, Amazon Clinic), are actively building and expanding direct healthcare delivery and pharmacy services. This strategic direction positions them to potentially develop highly integrated health platforms that could eventually include or directly compete with health insurance offerings. Leveraging their immense capital, technological prowess, vast data capabilities, and existing customer relationships, these tech giants could offer a more seamless, comprehensive, and potentially lower-cost alternative to existing models. This mirrors the disruptive impact of Apple's iPhone on Research in Motion's BlackBerry, where a new entrant with a superior, integrated platform fundamentally changed market expectations.
• Accelerated Vertical Integration and Ecosystem Development by Established Healthcare Giants: Major traditional healthcare players like UnitedHealth Group (through Optum) and CVS Health (through Aetna, MinuteClinic, and Oak Street Health) are aggressively acquiring and integrating care delivery assets, including physician groups, clinics, and pharmacies. This strategy aims to create highly efficient, end-to-end healthcare ecosystems that control costs, improve care coordination, and offer a unified experience. These vertically integrated behemoths can potentially offer superior value propositions by controlling the entire care continuum, from insurance to actual care delivery, making it challenging for tech-enabled insurers like Oscar to compete effectively on price or comprehensive service within a fragmented system. This parallels Netflix's ability to vertically integrate content creation and distribution, making Blockbuster's traditional model less viable.

Oscar Health (symbol: OSCR) operates in three main health insurance markets in the U.S.: individual and family plans, small group plans, and Medicare Advantage plans.

• Individual and Family Plans: The U.S. individual health insurance market is estimated at approximately $35.50 billion in 2024 and is projected to reach around $67.57 billion by 2034.
• Small Group Plans: The U.S. small group health insurance market covered over 9.6 million lives in 2023.
• Medicare Advantage Plans: The U.S. Medicare Advantage market reached 34.5 million beneficiaries in 2024. More than half (54%) of eligible Medicare beneficiaries, which translates to 34.1 million out of approximately 62.8 million individuals with Medicare Parts A and B, were enrolled in Medicare Advantage plans in 2025.

For Oscar Health (OSCR), several key drivers are expected to contribute to future revenue growth over the next two to three years:

1. Membership Growth: Oscar Health consistently identifies increasing its membership base as a primary driver of revenue. The company has demonstrated significant year-over-year membership growth, with a 28% increase to 2.1 million members by Q3 2025, and aims for continued expansion within the Affordable Care Act (ACA) marketplace. For example, membership grew by 41% year-over-year in Q1 2025, reaching 2 million members. Oscar Health also reported a 68% year-over-year increase in membership in Q3 2024, reaching approximately 1.65 million members.
2. Geographic Expansion: Oscar Health is actively expanding its presence by entering new states and increasing its county-level footprint. For instance, the company is expanding into Alabama and Mississippi, and plans to offer services in 573 counties across 20 states by 2026. This strategic expansion aims to capture a larger share of the individual market.
3. Disciplined Pricing and Rate Increases: The company has implemented a "disciplined pricing" strategy, including rate increases, to drive revenue growth and move towards profitability. Management has emphasized a weighted average rate increase of approximately 28% for 2026.
4. Growth in Individual Coverage Health Reimbursement Arrangement (ICHRA) Offerings: Oscar Health views the ICHRA market as a significant growth opportunity to attract small and medium-sized businesses and expand its individual market presence. The company plans to launch new ICHRA products in 2025, including those designed for "richer plans" and offering health savings account compatibility.
5. Launch of New Products and Services: Innovation through new product launches and health solutions is another expected driver. Oscar Health has highlighted strategic initiatives such as launching innovative health solutions like "HelloMeno" and an "AI health agent Oswell" to enhance its offerings and attract members.

Share Issuance

• In March 2021, Oscar Health raised approximately $1.4 billion in gross proceeds from its Initial Public Offering (IPO) by offering 36,391,946 shares of Class A common stock at $39.00 per share.
• In September 2025, Oscar Health priced a private offering of $355 million in 2.25% convertible senior subordinated notes due 2030, with an option for an additional $55 million in notes, with net proceeds estimated at about $342.5 million. These funds are intended for general corporate purposes, including AI-driven initiatives and enhancing consumer healthcare experiences.
• In 2025, Oscar Health issued $305 million in 7.25% convertible senior notes due 2031 to strengthen its capital structure. Additionally, in November 2025, $187.5 million of these notes were exchanged for 23,273,179 Class A shares.

Capital Expenditures

• Oscar Health reported capital expenditures of approximately $26 million in 2024, $29 million in 2023, and $26 million in 2022.
• For the last 12 months (as of November 2025), capital expenditures were reported as approximately -$34.13 million.
• The company intends to use capital for strategic initiatives focused on artificial intelligence, lowering the cost of care, and enhancing consumer healthcare experiences.