Director of Strategic Finance

Root was founded on the belief that car insurance is broken, and we set out to change it. We’re harnessing the power of technology to revolutionize this archaic, complicated industry. Using machine learning and mobile telematic platforms, we’ve built one of the most innovative insurtech companies in the world.

The Opportunity

We are seeking a strategically minded finance leader who can shape Root’s long-term financial strategy, drive capital allocation, and influence executive decision-making in a dynamic, high-growth environment. The Director of Strategic Finance will be a critical partner to the VP of Finance, with a dotted-line relationship to the Head of Investor Relations and Corporate Development, and regular exposure to the CFO and CEO.

This leader will establish a new, dedicated Strategic Finance function — focused on long-term financial planning, capital strategy, and strategic decision support. Unlike FP&A, which owns Root’s short-term budgeting and forecasting, this role looks beyond — building the models, frameworks, and insights that connect Root’s capital to its strategy. The Director of Strategic Finance will play a pivotal role in shaping Root’s financial future and providing executive-ready insights to guide growth, capital allocation, and strategic execution.

This is initially an individual contributor role, however you will shape strategy through influence and executive advisory, with the opportunity to build a team over time.

Salary Range:  $175,000 - $200,000 (STI & LTI Eligible)
Root is a “work where it works best” company. This means we will support you working in whatever location that works best for you across the US.

How You Will Make an Impact

Capital & Strategic Planning

• Build and own Root’s long-term financial model, linking capital requirements to growth ambitions.
• Conduct scenario planning, sensitivity analyses, and strategy math to support executive and board decisions.
• Partner with Corporate FP&A to extend quarterly insights into long-range views that inform enterprise strategy.

Capital Allocation & Transactions

• Develop ROI and capital efficiency frameworks to guide investment in new products, markets, and business initiatives.
• Support M&A evaluation and execution, including diligence, financial modeling, and integration planning.
• Collaborate with Investor Relations on capital strategy messaging, peer benchmarking, and market positioning.

Strategic Decision Support

• Track and analyze Root’s KPIs and OKRs, surfacing forward-looking insights and identifying areas of opportunity.
• Lead competitor benchmarking and external market research to inform decision-making.
• Partner with Product Delivery teams and Operations leaders to embed unit economics and growth efficiency metrics into strategic planning.

Organizational Capacity Planning

• Partner with HR and Product Delivery Teams (primarily Engineering leadership) to build integrated workforce and capacity plans, ensuring resources (product, engineering, analytics, data science, etc.) are aligned with Root’s annual planning and long-term strategy.
• Build frameworks to measure return on product investment, connecting headcount allocation and project spend to product outcomes and enterprise value.
• Develop dynamic capacity models that adjust for product roadmap changes, technology investments, and market conditions.
• Lead BvA (Budget vs. Actual) analysis for quarterly commitments and major strategic initiatives, providing transparency into resourcing efficiency and highlighting areas for reallocation or improvement.

Executive, Board & Investor Engagement

• Develop clear, compelling materials that translate complex financial analysis into concise narratives for executives, the Board, and external stakeholders.
• Play a visible role in quarterly board prep, investor days, and strategic offsites.
• Serve as a trusted advisor to the VP of Finance, CFO, and CEO on capital deployment, financial strategy, and organizational investment.
• Influence broadly across the CFO org, elevating strategic and financial rigor even without direct reports.

What You Will Need to Succeed

• 5+ years of progressive experience in Investment Banking, Private Equity, Strategic Finance, Management Consulting, or Corporate Development, ideally with exposure to insurance, fintech, or financial services.
• Deep expertise in capital modeling, valuation, and long-term financial planning.
• Experience supporting M&A transactions and/or complex financing initiatives.
• Strong background in organizational capacity or workforce planning, ideally with HR/People team collaboration.
• Proven ability to synthesize complex analysis into board-level communication.
• Self-starter with strong cross-functional influence, comfortable operating as an IC with executive exposure.
• Experience with insurance capital frameworks (RBC, reinsurance structures) is a strong plus

As part of Root's interview process, we kindly ask that all candidates be on camera for virtual interviews. This helps us create a more personal and engaging experience for both you and our interviewers. Being on camera is a standard requirement for our process and part of how we assess fit and communication style, so we do require it to move forward with any applicant's candidacy. If you have any concerns, feel free to let us know once you are contacted. We’re happy to talk it through.