Vice President, Corporate Development & Strategic Finance

Hi, we're Oscar. We're hiring a Vice President, Corporate Development & Strategic Finance to join our FP&A 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:

As a senior leader within the Oscar FP&A organization, this role will be the dedicated Strategic Finance Partner to the startup leadership teams and lead Corporate Development activities. Additionally, the VP, Corporate Development & Strategic Finance will serve as the primary FP&A Partner for the Technology organization, ensuring that our technical roadmap, engineering resources, and infrastructure investments are financially optimized and aligned with long-term business goals. 

You will report into the SVP, Deputy CFO.

Work Location: This position is based in our New York 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: $240,120 - $315,157 per year. You are also eligible for employee benefits, participation in Oscar's unlimited vacation program, company equity grants and annual performance bonuses.

Responsibilities:

Technology FP&A Partnership & Tech Business Strategy

• Serve as the lead finance partner to the CTO and Technology leadership, providing strategic oversight for the tech organization's budget and long-term financial health.
• Manage the financial complexities of a high-growth tech business, including cloud infrastructure optimization (e.g., AWS/GCP spend), R&D capitalization, and engineering headcount planning.
• Align technical roadmaps with financial targets, ensuring that engineering velocity is matched with disciplined capital allocation and ROI tracking.

Startup Business Partnership & "0 to 1" Strategy

• Act as the strategic co-pilot to Oscar's business development ventures, navigating the transition from initial concept to a scalable, margin-positive business model.
• Build the financial DNA, pro forma foundations, and "0 to 1" business cases from a blank canvas.
• Analyze cost structures and revenue quality early in the lifecycle to identify margin levers.
• Ensure ventures build a sustainable path to profitability through rigorous financial management.

Corporate Development & Deal Execution

• Provide Finance oversight for end-to-end deal execution (M&A, strategic partnerships).
• Identify disruptive HealthTech assets, build investment cases, and own the pro forma modeling, diligence, and integration handoff.
• Lead sophisticated, enterprise-wide financial and capital modeling to inform strategic decisions on growth initiatives and capital allocation.
• Conduct deep-dive ROI analyses to pressure-test assumptions on where to spend and expected returns.

Operating Plan Development & Parent Co Integration

• Lead the development of the multi-year enterprise Operating Plan, ensuring alignment with the overarching strategic plan.
• Serve as the primary bridge between venture leadership and the broader FP&A team for reporting, budgeting, and long-range planning.

Narrative Building & Executive Influence 

• Translate "startup metrics" and complex financial data into a clear story for the Board, Management Committee, and Operating Committee.
• Collaborate with executive stakeholders to drive strategic outcomes and corporate alignment.

Compliance & Other Duties

Compliance with all applicable laws and regulations 

Other duties as assigned 

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