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Salary: USD 185,000 - 250,000 / annual
Pawlicy Advisor, a venture-backed, profitable pet insurance marketplace, is seeking a Head of Finance to own the entire finance function and serve as the CEO's operating partner. This is a hands-on role where you will be the finance team on day one, supported by outsourced accounting and tax contractors whom you direct and may bring in-house as warranted.
Key Responsibilities:
Cash Management & Banking: Own cash forecasting, cash governance, and banking relationships. Assess capital options (equity, debt, non-dilutive) and recommend timing and structure. Lead financial workstreams for strategic transactions including financings, partnerships, and M&A.
Accounting, Close & Control: Deliver timely, accurate monthly closes and GAAP-compliant financials. Direct outsourced accounting and tax firms to defined deliverables. Own commission reconciliation and revenue assurance, including carrier statement reconciliation and revenue recognition. Maintain chart of accounts and system alignment across Brex, payroll, billing, and banking.
Operations, FP&A & Board Reporting: Own the three-statement operating model, annual budget, and scenario planning. Deliver monthly financial packages to CEO and Board including P&L, cash flow, and variance analysis. Own LTV/CAC and payback analyses by channel and segment. Support technical integration of financial data across company systems.
Finance Operating Model & Team: Own the mix of in-house staff and outsourced contractors with authority to restructure. Select and administer the finance systems stack with a bias toward automation.
Cross-functional Partnerships: Partner on compensation modeling, legal/risk matters, commercial partnerships, data and analytics initiatives, and company execution.
Success Metrics (90 days): Monthly close on defined schedule with documented review process. Operating model live and reviewed monthly. Complete audit of financial workstreams. Transaction-ready data room.
Success Metrics (12 months): CEO and Board receive concise, accurate packages driving decisions. Channel-level LTV/CAC published and trusted. Budget, hiring plan, and cash runway always reconciled. Strategic opportunities evaluated with rigorous analysis.
Requirements:
- 7+ years in finance, including 2+ years as second-in-command (Director or VP reporting to CFO or founder) at a venture-backed company
- Hands-on ownership of monthly close, GL, and financial statements
- Deep FP&A and three-statement modeling experience; fluency in scenario analysis, unit economics, and sensitivity modeling
- Direct experience with LTV/CAC, payback, and channel performance measurement in multi-channel or B2B2C business
- Proven experience scaling a startup through significant revenue growth
- Experience managing Board reporting and collaborating with venture firms
- Experience managing outsourced accounting, tax, and finance vendors to defined outcomes and budgets
- Strong systems orientation across QuickBooks Online, Brex, banking platforms, PEOs, Carta, and BI tools (Mixpanel, Tableau)
- Comfort working across HR, legal, and operations topics outside traditional finance
- Legally authorized to work in the United States without sponsorship
- Preferred: familiarity with insurance distribution or commission-based revenue models
