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:

This is a high-impact leadership role sitting at the intersection of a mature parent company and two ambitious new ventures (Trove and Lucie). 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. This role is the "CFO of the Spin-Off" and the financial architect for the tech org, ensuring these ventures scale with speed while maintaining the financial discipline and strategic rigor required by the enterprise.

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 

Requirements:

• Bachelor's degree in Finance, Economics, Business Administration, or a related field.
• 15+ years of progressive experience in analytical financial roles, with significant leadership responsibilities.
• 12+ years of demonstrated ability using expert financial modeling skills to effectively translate complex data into actionable insights, robust strategies, and comprehensive financial plans, particularly in a corporate development context.
• 8+ years of significant corporate development experience, including direct involvement in M&A financial modeling, valuation, and negotiation.
• 7+ years of experience collaborating, influencing, and presenting at the executive level, including direct interaction with C-suite and Board members.

Bonus points:

• Experience in similar roles in strategy consulting, financial services, or insurance industries (ex: private equity, venture capital, investment banking)
• Strong preference for healthcare industry experience and deep market knowledge.
• Advanced degrees or professional designations, such as an MBA or CFA.
• Proven experience supporting a Technology or Engineering organization, with familiarity in managing cloud costs (AWS/GCP), R&D efficiency, and software capitalization rules.