Full-Time
Associate – Strategic Finance
Updated on 8/20/2026
Oscar Health
1,001-5,000 employees
Tech-driven health insurance with virtual care
Compensation Overview
$87.2k - $114.4k/yr
New York, NY, USA
Hybrid
Hybrid role; 3 days on-site per week, Thursdays required, at NYC office.
Bachelor's, Master's, MBA
 Finance & Banking |
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- Bachelor's degree in Finance, Economics, or Actuarial or equivalent work experience
- 4+ years of finance experience including experience in Healthcare, Consulting, Insurance or Financial Services
- 2+ years of experience with google products - Sheets, Docs and Slides or Microsoft products.
- 2+ years of experience working with C-level executives.
- Craft recommendations using a data-driven approach combined with business intuition for senior executives to make pricing decisions that influence our growth and bottom-line
- Support build of models and tooling that produce relevant business insights, including competitive intelligence insights and scenario modeling
- Collaborate with Actuarial, Regional Leaders, Plan Design and Sales teams to develop portfolio strategy for each Oscar market
- Identify and research profitability tradeoffs, market trends, and membership insights to help guide company-wide strategic decisions
- Source, organize, and analyze data to support all strategic programs in the team
- Monitor important metrics and identify latest trends around the ACA landscape for leadership to help quickly inform tactics during selling season
- Report intra-year membership analytics to leadership to understand health of the business
- Compliance with all applicable laws and regulations
- Other duties as assigned
- MBA in finance, MS in Financial Analysis
- Experience in the managed care, healthcare or insurance
- Proficiency in SQL/BigQuery to analyze large datasets
- Proficiency working with NetSuite and Adaptive
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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Simplify's Take
What believers are saying
- On August 6, 2026, Oscar raised full-year operating earnings guidance to $500 million-$700 million.
- Q2 2026 revenue reached $4.88 billion, up 70.4%, with 2.96 million members.
- Mario Schlosser's June 1, 2026 advisor role keeps him focused on AI.
What critics are saying
- Oscar expects 250,000-300,000 retroactive ACA disenrollments from CMS in 2026.
- House Judiciary subpoena pressure over Obamacare subsidy fraud extends Oscar's regulatory overhang into 2026.
- If CMS removes too many members, Oscar's ACA concentration breaks its growth model.
What makes Oscar Health unique
- Oscar's Oswell AI routed one-in-four members to care sites, saving $75 per visit.
- Oscar's ICHRAx, launched August 2026, targets gig and part-time workers through employers.
- Oscar's claims platform hit 98.7% first-pass accuracy and processed most claims under 48 hours.
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Benefits
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.
Growth & Insights and Company News
6 month growth
↓ -1%1 year growth
↓ -1%2 year growth
↓ -1%Oscar Health reported second-quarter results that exceeded Wall Street expectations, though the market reacted negatively. Revenue reached $4.88 billion, beating estimates of $4.74 billion and marking 70.4% year-over-year growth. Adjusted earnings per share came in at $1.10, significantly above the $0.38 estimate. CEO Mark Bertolini attributed the performance to disciplined pricing, technology-driven efficiencies, and strong execution in individual health insurance. Membership increased 46% year-over-year, whilst administrative cost ratios hit historic lows. Operating margin improved to 8%, up from negative 8% in the same quarter last year. Adjusted EBITDA of $415.3 million substantially exceeded the $170.9 million estimate. During the earnings call, analysts questioned management on outpatient utilisation trends, medical loss ratio guidance, and the potential impact of CMS eligibility reviews on member retention.
Wall Street analysts have issued bearish price targets for several stocks, signalling serious concerns about their prospects. StockStory conducted independent analysis to identify buying opportunities and companies to avoid. The firm recommends avoiding Envista Holdings, a global dental products company. Its revenue grew just 3.4% annually over five years, whilst earnings per share fell 7% annually. Negative returns on capital suggest growth strategies have backfired. StockStory also advises caution on OneMain Holdings, which provides personal loans to nonprime consumers. Despite 5.5% annual revenue growth over five years, earnings per share declined 9.3% annually. The firm identifies Oscar Health, a technology-focused health insurance company founded in 2012, as a potential buying opportunity despite Wall Street's pessimism.
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.