OSCR Stock: Insider Activity, Filings & Research

Oscar Health, Inc. (OSCR) — Drillr’s hub for OSCR insider activity, SEC filings, earnings signals and AI research. Over the trailing 3 months, OSCR insiders filed 1 open-market buy and 13 sales (SEC Form 4).

Sentiment

64/100

Buys (3m)

Sells (3m)

Net (3m)

$4.9M

Insiders buyingFirst buy in 6 quarters

Insider trades by month Buys Sells

Dec

Jan

Mar

Apr

May

Jun

Context3-month price +36.2%Institutions mixed (13F)

Date	Insider	Type	Shares	Price
Jun 4, 2026	McAnaney Adamofficer: Chief Legal Officer	Sell	7,065	$21.74
Jun 4, 2026	Baltrus Victoriaofficer: Chief Accounting Officer	Sell	1,091	$21.74
Jun 4, 2026	Baltrus Victoriaofficer: Chief Accounting Officer	Sell	432	$22.45
Jun 4, 2026	Liang Janetofficer: President, Oscar Insurance	Sell	3,535	$22.45
Jun 4, 2026	Blackley Richard Scottofficer: Chief Financial Officer	Sell	22,706	$21.74
Jun 4, 2026	Schlosser Mariodirector	Sell	9,668	$22.45
Jun 4, 2026	Blackley Richard Scottofficer: Chief Financial Officer	Sell	8,977	$22.45
Jun 4, 2026	McAnaney Adamofficer: Chief Legal Officer	Sell	2,794	$22.45
Jun 4, 2026	Schlosser Mariodirector	Sell	24,452	$21.74
Jun 4, 2026	Liang Janetofficer: President, Oscar Insurance	Sell	8,940	$21.74
May 20, 2026	Blackley Richard Scottofficer: Chief Financial Officer	Sell	110,000	$25.03
May 18, 2026	Blackley Richard Scottofficer: Chief Financial Officer	Sell	8,741	$23.79
May 18, 2026	Blackley Richard Scottofficer: Chief Financial Officer	Sell	91,259	$23.10
Apr 13, 2026	Plouffe Daviddirector	Grant	1,461	—
Apr 13, 2026	BOYD JEFFERY Hdirector	Grant	3,610	—

Source: OSCR SEC Form 4 filings, latest Jun 4, 2026. For informational purposes only — not investment advice.

Overview

Oscar Health, Inc. (NYSE:OSCR) is a technology-driven health insurance company founded in 2012 and headquartered in New York, New York. The company went public in March 2021, having previously operated under the name Mulberry Health Inc. Oscar represents a new generation of health insurers that leverages artificial intelligence, digital platforms, and consumer-centric design to modernize the health insurance experience. After years of losses during its growth phase, the company achieved profitability in 2024 and has emerged as one of the largest carriers in the Affordable Care Act (ACA) marketplace with approximately 2 million members as of 2025.

Business

Oscar Health operates in the health insurance industry, specifically focusing on individual and small group health insurance plans sold through government-regulated marketplaces. The company's core business revolves around three main product lines that generate revenue through insurance premiums. Individual & Family Plans represent Oscar's largest segment, accounting for the majority of its revenue. These are health insurance plans sold to individuals and families primarily through the ACA marketplace (also known as Obamacare exchanges). The ACA marketplace was created in 2014 to provide subsidized health insurance to Americans who don't receive coverage through employers or government programs like Medicare and Medicaid. Oscar competes with traditional insurers like UnitedHealthcare, Anthem, and Centene in this space, but differentiates itself through technology-first approach and consumer-friendly digital experiences. Small Group Plans target small businesses with fewer than 50 employees that want to provide health insurance benefits to their workers. This market segment allows Oscar to expand beyond individual consumers into the employer-sponsored insurance space, though it remains a smaller portion of their business compared to individual plans. Medicare Advantage Plans serve seniors aged 65 and older as an alternative to traditional Medicare. Medicare Advantage plans are offered by private insurers but regulated and subsidized by the federal government. This represents Oscar's newest product line and a significant growth opportunity given the aging U.S. population. The company also operates +Oscar, a technology platform that Oscar licenses to other health insurers and healthcare organizations. This business-to-business offering allows Oscar to monetize its proprietary technology, data analytics, and operational expertise beyond its own insurance products. Additionally, Oscar has been expanding into ICRA (Individual Coverage Reimbursement Arrangement) products, which allow employers to reimburse employees for individual health insurance premiums rather than offering traditional group plans.

Competitive moat

Oscar's competitive moat is moderate but growing, built primarily around its technology platform and operational efficiency rather than traditional insurance industry advantages like provider network scale or regulatory barriers. The company's strongest moat element is its proprietary technology stack, which includes AI-powered care management tools, digital member engagement platforms, and data analytics capabilities that have taken years to develop and refine. This technology enables Oscar to operate with lower administrative costs and better medical cost management compared to legacy insurers still relying on outdated systems. The company benefits from network effects within its technology platform, as more data from members and providers improves the effectiveness of its AI algorithms and care coordination tools. Oscar's consumer-centric approach and digital-first experience also create switching costs, as members become accustomed to features like virtual urgent care, AI-powered care guides, and seamless mobile app experiences that traditional insurers struggle to match. However, Oscar's moat faces significant challenges. Large incumbents like UnitedHealthcare, Anthem, and Aetna have vastly superior financial resources, established provider relationships, and economies of scale that allow them to offer more competitive pricing and broader network access. These companies are also investing heavily in their own digital transformation initiatives, potentially eroding Oscar's technology advantage over time. Regulatory risks pose another threat, as changes to ACA subsidies, risk adjustment formulas, or marketplace rules could disproportionately impact Oscar's business model. The health insurance industry also has relatively low barriers to entry for well-capitalized competitors, and Oscar must compete on price in government-regulated marketplaces where product differentiation is limited. New entrants backed by major technology companies or private equity firms could potentially replicate Oscar's technology-first approach while bringing superior capital resources to bear. The company's moat is strongest in markets where it has achieved scale and operational efficiency, but remains vulnerable in newer markets where it lacks established provider relationships and member density.

Risks & safety

Oscar's margin of safety appears reasonable but not exceptional, with the company having achieved profitability and positive cash generation but still facing inherent volatility in the health insurance business. • Liquidity and Solvency: Strong cash position with $2.2 billion in cash and short-term investments as of Q1 2025. Positive operating cash flow of $879 million and free cash flow of $870 million in Q1 2025. Debt-to-equity ratio of 0.22 indicates conservative leverage. No immediate solvency concerns. • Valuation Metrics: Trading at attractive multiples with P/E ratio of 3.0 and EV/EBITDA of 1.1 based on Q1 2025 results. Price-to-book ratio of 2.5 is reasonable for a profitable growth company. However, these metrics are based on a strong quarter and may not reflect normalized earnings. • Other Considerations: Health insurance earnings are inherently volatile due to medical cost fluctuations. Regulatory dependency on ACA marketplace creates policy risk. Strong revenue growth of 42% year-over-year provides growth cushion. Membership base of 2 million provides reasonable scale, though still smaller than major competitors.

Recent development

Over the past few years, Oscar has undergone a significant strategic transformation from a growth-at-all-costs startup to a disciplined, profitable health insurer. The company's most important pivot occurred in 2022-2023 when management shifted focus from pure membership growth to achieving profitability through improved medical cost management and operational efficiency. Technology and AI Integration has become central to Oscar's strategy, with the company implementing over 50 AI use cases across its operations. Recent innovations include AI-powered care guides that improve member service efficiency, clinical intake bots, and tools that help reduce hospital readmission rates by 10%. The company has also developed AI systems for fraud detection and provider administrative support, with over 50% of urgent care onboarding now AI-powered. Product Innovation has accelerated with the launch of specialized offerings like multi-condition plans for managing diabetes, pulmonary, and cardiovascular diseases together. Oscar introduced "Buena Salud," a Spanish-first solution targeting Hispanic and Latino members, and developed tech-first HMO products designed to provide frictionless healthcare experiences. The company has also expanded geographically, entering 165 new counties across 20 states in recent years. Business Model Diversification includes the development of +Oscar as a technology platform for other insurers and the expansion into ICRA (Individual Coverage Reimbursement Arrangement) products. While still small, the ICRA business represents access to over 70 million potential lives in the under-50 employee and middle market segments. Oscar has also been exploring opportunities in Medicare Advantage and small group markets to reduce dependence on the individual ACA marketplace. Operational Excellence initiatives have focused on achieving the company's stated goals of 20% revenue compound annual growth rate and 5% operating margin by 2027. This includes significant improvements in the SG&A expense ratio, which improved by 520 basis points in 2024, and continued focus on medical loss ratio management through better care coordination and member engagement.

OSCR company profile · for informational purposes only — not investment advice.

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