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Salary: USD 185,000 - 250,000 / annual
Pawlicy Advisor is a venture-backed, profitable pet insurance marketplace that helps pet parents compare plans and choose coverage through veterinary clinics and partners nationwide. You will join as Head of Finance, owning the entire finance function and serving as the CEO's operating partner in a hands-on role.
On day one, you are the finance team, supported by outsourced accounting and tax contractors whom you direct and may bring in-house as warranted. You will own cash management, the monthly close, the operating model, financial reporting, and partner in operational and strategic decision-making, reporting directly to the CEO with a defined path to CFO as the business scales.
Key Responsibilities:
Cash Management & Banking: Own cash forecasting and governance to drive capital allocation and growth investment decisions. Manage banking and investor reporting relationships. Assess capital options (equity, debt, non-dilutive) and recommend timing and structure. Own the financial workstream 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 and timelines. Own commission reconciliation and revenue assurance, including carrier statement reconciliation and revenue recognition. Maintain chart of accounts and system alignment. Oversee AP, AR, vendor payments, payroll, and tax compliance.
Operations, FP&A & Board Reporting: Own the three-statement operating model, annual budget, and scenario planning. Deliver monthly financial packages to CEO and Board with P&L, cash flow, variance analysis, and proactive recommendations. Prepare Board materials and serve as a key operator galvanizing the team toward OKRs. Own LTV/CAC and payback analyses by channel and segment. Support technical integration of financial data across systems.
Finance Operating Model & Team: Own the mix of in-house staff and outsourced contractors with authority to restructure, replace, or bring work in-house based on defensible, data-driven cases. Select and administer the finance systems stack (QuickBooks Online, Brex, payroll, banking, billing) with bias toward automation.
Cross-functional Partnerships: Work with HR on compensation modeling, leveling, and equity; with Legal on corporate and commercial matters; with Product and Partnerships on commercial terms and partner economics; with Data on dashboards and analytics; and contribute to business development initiatives as an externally-facing team member.
Success Metrics (90 days): Monthly close on defined schedule with documented review process. Operating model live and reviewed monthly. Become expert on company's market, strategy, and operations. Complete audit of financial workstreams with scoped processes. Transaction-ready data room. Support 2027 budget development.
Success Metrics (12 months): CEO and Board receive concise, accurate packages driving decisions. Channel-level LTV/CAC and payback published and trusted. Budget, hiring plan, and cash runway always reconciled and forward-looking. Strategic opportunities evaluated in days with rigorous analysis. Maintain active operational presence across company.
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; you have done the work, not just reviewed it
- 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 directly 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 or 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
Work Style: You are hungry to scale a company and have done high-paced operational work beyond finance. You do the work yourself first, then build process around it. You are comfortable being the entire finance function for a period. You are a clear, direct communicator who distills complexity into simple, actionable narratives for non-finance colleagues. You have a bias for action and move from analysis to decision to execution quickly. You are rigorously organized, document your work as a way of collaborating, and use digital task management tools (ClickUp) and AI tools (Claude) daily. You streamline and compound productivity with AI before hiring. You challenge assumptions and welcome being challenged in return. You treat every dollar of finance spend like any other investment: clear hypothesis, measured payback, and learnings that feed the next iteration.
