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Jerry is a fintech/insurtech platform managing car insurance, home, motorcycle, and RV ownership. The company has reached 5M+ customers, raised $240M+, and achieved profitability in 2024. It is now expanding into adjacent verticals and making increasingly consequential capital allocation decisions.
You will join as Strategic Finance Manager reporting to the VP of Finance, owning the financial operating model, planning cycle, and analytical partnership on new opportunities. This is a foundational role building the financial infrastructure and discipline the company runs on.
Key responsibilities:
**Operating Model & Planning:** Own Jerry's driver-based operating model for the base business and expand it as new insurance products and business lines launch. Run the annual budget and long-range planning process end-to-end, including cadence, assumptions, stakeholder inputs, and consolidated executive commitments. Own the monthly and quarterly forecast cycle and variance analysis, explaining what moved against plan and what it means for the forecast.
**Executive Reporting & Leadership:** Write the executive narrative translating financial results into clear business insights for the CFO, founders, board, and investors at a standard that survives external diligence. Lead monthly business reviews with functional leaders, turning numbers into actionable business decisions.
**New Opportunity Analysis:** Build financial models for new products, verticals, channels, or partnerships—sizing markets, modeling economics, and evaluating capital commitment and return profiles. Read results back against the case once live, monitoring product and channel economics (CAC, payback, retention, LTV, contribution margin). Support corporate development on capital markets, investor workstreams, diligence, and transaction analysis. Frame build/buy/partner decisions.
**Vendor & Spend Management:** Build business cases before vendor commitments, support negotiation on terms, and give budget owners visibility to manage their numbers.
**Systems & Process:** Support evaluation and implementation of a planning system, assessing options, making recommendations, and owning rollout.
You will work closely with the CFO and founders in a remote-first environment with optional offices in Palo Alto, NYC, Chicago, and Toronto.
**Requirements:**
- 4+ years of relevant experience, ideally combining 2+ years at a reputable investment bank, corporate development group, or private equity firm with 2+ years in strategic finance or FP&A at a high-growth company
- Bachelor's degree in finance, accounting, economics, or a similarly quantitative field
- Strong financial modeling skills: driver-based operating models, three-statement mechanics, scenario and sensitivity analysis, working command of accounting concepts and GAAP
- Experience with unit economics in a consumer or marketplace business, including CAC, LTV, payback, cohort retention, and contribution margin
- Track record of translating complex analysis into clear narrative for executive or investor audience
- Startup or high-growth experience strongly preferred, including building financial processes from scratch
- Hands-on fluency with AI tools for analysis, research, and workflow automation
**Nice to have:**
- Insurance, insurtech, fintech, or marketplace experience
- CFA certification
- Vendor negotiation or procurement exposure
- Finance tech stack experience (NetSuite, Ramp, planning tools)
