Healthcare · Profile from Healthcare Research Companion
Oscar Health, Inc.
The venture-backed, technology-first health insurer that bet its existence on the Affordable Care Act's individual exchanges. Oscar spent a decade losing money, went public in 2021 at ~$7.9bn and lost most of that value, then under Mark Bertolini became the largest ACA-focused insurtech and the first of its cohort to post an annual profit (2024). It was knocked back into loss by the 2025 exchange morbidity shock and returned to strong profit in the first half of 2026 (verify).
At a glance
- Founded
- 2012, New York City; first plans sold on the New York ACA exchange for coverage starting January 2014
- Founders
- Mario Schlosser (CEO to 2023), Joshua Kushner (Thrive Capital) and Kevin Nazemi
- Headquarters
- New York, New York
- Ownership / structure
- Public company, NYSE: OSCR (IPO March 2021); dual-class shares (Class B held by founders/Thrive-related holders)
- Leadership (2026)
- Mark Bertolini, CEO (since April 2023; former Aetna CEO); Scott Blackley, CFO (verify); Joshua Kushner, vice chair (verify current titles)
- Segment and buyer
- Payer: individual (ACA marketplace) health insurance, increasingly sold through ICHRA (employer-funded individual coverage); formerly small group (Cigna+Oscar), Medicare Advantage and a software platform (+Oscar)
- Scale
- ~2.04m individual and small-group members at 31 December 2025; record ~3.4m members after 2026 open enrollment (1 February 2026), ~2.96m effectuated at 30 June 2026 (reported); 2025 revenue ~$11.7bn
- Capital raised / valuation / market cap
- ~$1.6bn+ raised privately (2013–2020, reported); IPO raised ~$1.4bn at $39/share (~$7.9bn valuation); shares fell to ~$2–3 by late 2022, recovered in 2024–2026 (verify current market cap)
- Signature moves (incl. failures)
- ACA exchange bet (2012–14); retreat from Dallas and New Jersey (2016); Alphabet investment (2018); Cigna+Oscar small group (2020–24); 2021 IPO and collapse; +Oscar platform and Medicare Advantage exit (2021–23); Bertolini turnaround (2023); first annual profit (2024); ICHRA push and 2025 morbidity shock; 2026 rebound (verify)
9 strategic moves analysed
Each one gets a full strategy file in the companion: context, the decision, the financing, what happened, and the lesson.
2012
Founding and ACA Exchange Bet
Founding / launch
2016
Market Retreat Dallas New Jersey
Restructuring (market exit and network redesign)
2018
Alphabet Investment
Funding round / strategic partnership
2020
Cigna Oscar Small Group
Partnership (co-branded insurance product with risk sharing)
2021
IPO
IPO
2021
Plus Oscar and Medicare Advantage Exit
Launch (platform business) followed by divestiture/market exit
2023
Bertolini Turnaround
Restructuring / leadership change
2024
First Annual Profit
Restructuring outcome / profitability milestone
2025
ICHRA Push and Morbidity Shock
Pricing change / strategy reset (guidance cut, rate refiling, reduction in force, ICHRA expansion)