Full-Time
Tech-driven health insurance with virtual care
$163.9k - $215.2k/yr
New York, NY, USA
Hybrid
Hybrid role; 3 days in-office per week with Thursdays mandatory in NYC.
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Oscar Health is a U.S. health insurer that uses technology to simplify health care for individuals, families, and small businesses, offering ACA-compliant and other plans. Its products run on a digital platform with 24/7 virtual care and tools to find in-network doctors, hospitals, and pharmacies, plus cost-management features. It differentiates itself with a tech-driven member experience, high accessibility, round-the-clock telemedicine, and clear access to in-network providers. The goal is to make healthcare simple, accessible, and affordable in the United States by streamlining enrollment, care access, and costs.
Company Size
1,001-5,000
Company Stage
IPO
Headquarters
New York City, New York
Founded
2012
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Health insurance - That’s a given. Employees and their families receive incredible health insurance.
Financial benefits - A penny saved....we’re talking about a 401K plan, health savings accounts, and more.
Well @ Oscar - We care about your wellness with fitness classes and access to mental health support.
Work-Life Balance - We offer multiple time-off options, wellness days, and 10+ weeks of parental leave.
Learning & Development - We offer everything from mentorship to management training.
Oscar Health reported second-quarter results that exceeded analysts' expectations, with revenue rising 70.4% year on year to $4.88 billion. The health insurance company's adjusted earnings per share of $1.10 significantly beat consensus estimates of $0.38. CEO Mark Bertolini credited disciplined pricing, technology-driven cost efficiencies, and strong execution in the individual health insurance market for the performance. Membership grew 46% whilst administrative cost ratios reached historic lows. The company is focusing on AI-powered cost controls and operational efficiency going forward. Its proprietary Oswell Agent uses member data to guide care decisions, saving members an average of $75 per appointment. AI-powered claims processing achieved 98.7% first pass accuracy. Oscar Health is targeting expansion in the gig and part-time worker market through products like ICHRA. Management noted caution regarding CMS eligibility reviews' impact on membership churn.
Oscar Health reported record first-half profitability of $1 billion in net income for the first half of 2026, driven by disciplined pricing and a scalable technology platform. The company raised its full-year earnings from operations guidance to $500 million–$700 million. The insurer leveraged its proprietary AI agent "Oswell" to guide one in four members to high-value care sites, saving an average of $75 per appointment. AI-powered medical economics models are expected to generate tens of millions in annual savings by identifying pharmacy cost outliers early. Oscar recognised a $160 million favourable risk adjustment for 2025 in the second quarter. The company projects a full-year MLR between 81.5% and 82.5%, anticipating seasonal utilisation increases as members meet deductibles. The firm launched ICHRAx, an electronic data exchange platform designed to facilitate employer transitions from defined benefit to defined contribution plans.
Oscar Health beat Wall Street's revenue expectations in Q2 CY2026, reporting sales of $4.88 billion, up 70.4% year on year and 2.9% above analyst estimates of $4.74 billion. The health insurance company's GAAP profit of $1.10 per share significantly exceeded consensus estimates of $0.41. The company also reported adjusted EBITDA of $415.3 million, well above the $170.9 million analysts expected. Operating margin improved to 8%, compared with negative 8% in the same quarter last year. Free cash flow margin rose to 42.6% from 17.5% year on year. Following the results, Oscar Health's stock jumped 11.8%. Analysts expect revenue to grow 25.5% over the next 12 months.
This article examines three companies based on their cash-generating capabilities and investment potential. Starbucks, with a 9.5% trailing 12-month free cash flow margin, faces challenges including declining same-store sales and a projected 1.6% sales decline. Operating margins fell by 3 percentage points as expenses increased relative to revenue. The stock trades at 35.5x forward P/E. Inter Parfums, which manufactures fragrances for brands like Kate Spade and Van Cleef & Arpels, shows stronger fundamentals with a 14.4% free cash flow margin and 59.7% gross margin. The company trades at 24.8x forward P/E. Oscar Health, a technology-focused health insurer, demonstrates the strongest performance with 21% free cash flow margin. The company achieved 42.6% annual revenue growth over two years and 31.5% annual earnings per share growth over four years. Its free cash flow margin expanded by 19.9 percentage points over five years.
Oscar Health has attracted attention following strong revenue growth and increased exposure to the Affordable Care Act market, alongside mixed analyst views on valuation. The company reported 52.6% revenue growth and solid free cash flow, supporting its tech-focused ACA platform strategy. A family trust linked to director Mario Schlosser recently sold and converted Class A and Class B shares under a pre-arranged trading plan, representing portfolio diversification rather than a shift in ownership. The investment case centres on whether Oscar can convert revenue and membership growth into sustainable profitability whilst managing medical costs and regulation. Analysts project widely varying outcomes, with optimistic forecasts reaching $25.5 billion revenue and $1.1 billion earnings by 2029. Key risks include persistent medical cost volatility and margin sensitivity to regulatory decisions.