Hi, we're Oscar. We're hiring a Senior Analyst, Mergers and Acquisitions to join our Strategic Planning Team.

Oscar is the first health insurance company built around a full stack technology platform and a relentless focus on serving our members. We started Oscar in 2012 to create the kind of health insurance company we would want for ourselves—one that behaves like a doctor in the family.

About the role

The Senior Analyst, Mergers & Acquisitions supports Oscar’s growth and diversification initiatives, including M&A, strategic partnerships, venture investments, and portfolio company priorities. This role develops research, financial analysis, market insights, and executive-ready materials to support strategic decision-making and transaction execution. The Analyst independently manages defined workstreams, coordinates cross-functional initiatives, and synthesizes complex information into clear recommendations, escalating higher-risk or ambiguous matters as appropriate.

You will report into the Director, Financial Corporate Strategy.

Work Location: This position is based in our New York, NY office, requiring a hybrid work schedule with 3 days of in-office work per week. Thursdays are a required in-office day for team meetings and events, while your other two office days are flexible to suit your schedule. #LI-Hybrid

Pay Transparency: The base pay for this role is: $91,908 - $120,629 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program and annual performance bonuses.

Responsibilities

Develop financial projections, valuation models, and market-sizing analyses; identify and pressure-test key assumptions to evaluate growth, investment, and transaction opportunities.
Conduct commercial due diligence through quantitative and qualitative research, expert interviews, surveys, and competitive analysis to assess market attractiveness and validate strategic opportunities.
Prepare strategic planning materials, executive-level summaries, and analyses for senior leaders, Board members, and other stakeholders to support timely decision-making.
Support diligence and transaction execution by organizing and synthesizing complex information, identifying key risks and insights, and communicating clear takeaways and recommendations.
Lead defined cross-functional workstreams across Oscar and its portfolio companies through disciplined project management, clear ownership, milestones, dependencies, and follow-through.
Manage multiple concurrent priorities in a dynamic environment, independently progressing assigned work and escalating workload, risk, or decision points when appropriate.
Identify opportunities to improve Corporate Strategy team productivity, analytical quality, and scalability through process improvements, AI, and other innovative tools.
Compliance with all applicable laws and regulations.
Other duties as assigned.

Requirements

Bachelor’s degree in Finance, Economics, Business Administration, Engineering, or a related quantitative discipline, or 4 years of relevant experience
1+ years of experience in investment banking, transaction advisory, corporate development, management consulting, corporate strategy, FP&A, or a related analytical role.
Experience building financial projections, valuation models, market-sizing analyses, or comparable quantitative business cases.
Experience conducting commercial due diligence, market research, competitive analysis, or other quantitative and qualitative strategic analysis.
Experience preparing executive-ready presentations, strategic planning materials, or decision-support analyses for senior stakeholders.
Experience managing multiple concurrent projects or workstreams and coordinating with cross-functional stakeholders.
Experience synthesizing complex or disparate information into clear findings, recommendations, or next steps.

Bonus points

Experience in healthcare, health insurance, healthcare technology, or another regulated industry.
Experience supporting M&A, strategic partnerships, venture investments, or portfolio-company initiatives.