VP of Strategic Finance for Lucie & Trove

About the role

The VP of Strategic Finance for Lucie & Trove is a pivotal leadership position accountable for architecting and owning the comprehensive financial model and operating plan for these nascent ventures. This role serves as the primary architect of business performance management, rigorously tracking and optimizing all financial and operational metrics through deep collaboration with Corporate Strategy, Sales, Product, Marketing, and Operations teams to fuel scalable growth. The position sits at the critical junction where a mature, established insurance platform intersects with two bold, nascent concepts in Trove and Lucie, requiring navigation of distinct yet intertwined ambitions. You will provide decisive financial counsel and strategic direction directly to the SVP, Deputy CFO, shaping high-stakes choices from inception through scale. The role demands a rare blend of entrepreneurial mindset and corporate discipline, constructing frameworks that translate visionary ideas into viable, profitable businesses. You will own the narrative of financial viability, articulating trade-offs and opportunities to ensure each venture meets its strategic objectives and capital efficiency targets. Success in this role means building the financial backbone and governance that allows these ventures to move from concept to sustainable, measurable growth.

Key facts

What you'll do

Develop and own the end-to-end financial model and operating plan for Lucie and Trove, ensuring alignment with Oscar's overarching strategic goals and resource allocation.

Partner deeply with Corporate Strategy to evaluate growth vectors, assess market opportunities, and model scenarios for strategic investments and potential mergers or acquisitions.

Collaborate with Sales leadership to design pricing structures, forecast revenue pipelines, and analyze go-to-market strategies to maximize market penetration and customer lifetime value.

Work hand-in-hand with Product teams to assess feature investment priorities, quantify build versus buy decisions, and model the financial impact of product roadmaps on unit economics.

Champion data-driven decision making by constructing actionable insights and robust KPI frameworks that guide leadership choices on budgeting, staffing, and channel optimization.

Establish and oversee scalable finance processes, controls, systems, and recurring operating cadences tailored to the unique needs of high-growth ventures.

Design and maintain advanced reporting infrastructure and executive dashboards that deliver clear visibility into financial health, operational performance, and key milestone tracking.

Define and implement rigorous financial governance practices, including cost center allocations, budget ownership frameworks, and variance analysis procedures.

Partner closely with accounting, legal, tax, and compliance teams to ensure all financial operations adhere to internal controls and external regulatory requirements.

Recruit, develop, and lead a high-performing finance function, fostering a culture of excellence, accountability, analytical rigor, and operational discipline as the business expands.

Act as a core horizontal conduit, synthesizing inputs from diverse Oscar teams and distilling them into coherent strategies and recommendations for the venture leadership.

Own the development of leadership reviews, board materials, and investor presentations, ensuring compelling storytelling backed by rigorous financial analysis.

Influence organizational design by advising on team structures, hiring plans, and role design to support scalable execution and efficient operations.

Drive the evaluation and execution of corporate development initiatives, including financial modeling for M&A, valuation analyses, and negotiation support.

Ensure strict compliance with all applicable laws, regulations, and Oscar policies, maintaining the highest standards of financial integrity and risk management.

Requirements

Hold a Bachelor's degree in Finance, Economics, Business Administration, or a closely related quantitative field.

Bring a minimum of 15 years of progressive experience in analytical financial roles, with a demonstrated history of increasing leadership scope and impact.

Possess 12 or more years of hands-on expertise in advanced financial modeling, specifically translating complex data sets and business assumptions into actionable insights, robust strategies, and comprehensive financial plans.

Have a minimum of 8 years of deep corporate development experience, including direct responsibility for M&A financial modeling, valuation exercises, due diligence, and negotiation preparation.

Demonstrate 7 or more years of experience effectively influencing and presenting at the executive level, including direct interaction with C-suite executives and Board members in a corporate environment.

Show a proven track record of building and managing high-performing finance teams, with success in recruiting, developing, and mentoring senior finance professionals.

Exhibit strong written and verbal communication skills, capable of simplifying complex financial concepts for non-financial stakeholders while maintaining precision for technical audiences.

Display unwavering integrity and sound judgment in navigating ambiguous situations, making balanced decisions that consider multiple stakeholders and long-term implications.

Nice to have

Previous experience within the insurance or healthcare technology sector is highly valued.

Prior hands-on experience building and scaling new ventures or startup environments is strongly preferred.

Demonstrated success with fundraising, investor relations, or managing board-level financial processes is a significant advantage.

Experience utilizing advanced data analytics platforms and visualization tools to drive strategic decision-making is beneficial.

A background in product finance, pricing strategy, or subscription-based business models is considered a bonus.

Practical notes

This is a full-time position based in Oscar's New York City office, requiring a hybrid schedule with three days per week in the office. Thursdays are mandatory for in-office presence to facilitate team meetings and company events, while the remaining two office days offer flexibility around your personal schedule. Compensation details and equity grants are aligned with Oscar's pay transparency policy. All employment is contingent upon satisfactory completion of background checks and compliance verification.