VP of Strategic Finance for Lucie & Trove

Hi, we're Oscar. We're hiring a VP of Strategic Finance for Lucie & Trove 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:

The VP of Strategic Finance for Lucie & Trove is a high-impact leadership role responsible for building and owning the financial model and operating plan for these new ventures. The role drives business performance management across all financial and operational metrics by partnering with Corporate Strategy, Sales, Product, Marketing and Operations teams to drive growth and optimize performance.

This is a high-impact leadership role sitting at the intersection of a mature parent company and two ambitious new ventures (Trove and Lucie).

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:

Strategic Finance & Business Partnership

• Working closely with senior leadership to develop a financial and operating plans that drives a sustainable business model for the new ventures  
• Serve as a trusted thought partner to leadership on growth strategy, strategic investments, pricing, partnerships, and operational scaling decisions
• Develop actionable insights and KPI frameworks to guide decision-making and resource allocation

Build & Scale the Finance Function

• Stand up scalable finance processes, controls, systems, and operating cadences for the new ventures
• Design reporting infrastructure and dashboards that provide visibility into financial and operational performance.
• Establish financial governance practices including cost center allocations
• Partner with accounting, legal, tax, and compliance teams to ensure appropriate controls and risk management.
• Recruit, develop, and lead a high-performing finance organization as the business scales

Executive Leadership

• Serve as one of the core horizontal conduits between Oscar’s executive leadership team and the new ventures
• Help build the operating rhythm of the business, including leadership reviews (MBRs), board materials, and investor presentations
• Influence organizational design, hiring plans, and capital allocation decisions
• Foster a culture of accountability, analytical rigor, and operational excellence

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.