Head of Finance

About the Role

Pawlicy Advisor is a venture-backed pet insurance marketplace that helps pet parents compare plans and choose the right coverage, distributed through veterinary clinics and partners nationwide. The business is profitable and growing. Pawlicy Advisor is hiring a Head of Finance to own the entire finance function and serve as the CEO’s operating partner. This is 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 the business case warrants.

You will own cash, the monthly close, the operating model, financial reporting, and partner in operational and strategic decision-making. The role reports directly to the CEO and is designed to grow into an executive seat as the business scales.

• Own the cash forecast and cash governance to proactively drive capital allocation and growth investment decision-making.
• Manage banking and investor reporting relationships.
• Assess capital options (equity, debt, non-dilutive) and recommend timing and structure with clear tradeoffs.
• Own the financial workstream for strategic transactions (financings, partnerships, M&A): models, data room, and investor and counter party materials, in partnership with the CEO and counsel.

• Deliver a timely, accurate monthly close and GAAP-compliant financials; you review every close personally.
• Direct outsourced accounting and tax firms; hold them to defined deliverables, timelines, and cost.
• Own commission reconciliation and revenue assurance: carrier statement reconciliation, commission receivables, and revenue recognition to identify unpaid, underpaid, and misattributed commissions and recover what Pawlicy is owed.
• Maintain the chart of accounts and keep Brex, payroll, billing, and banking systems aligned with the general ledger.
• Oversee AP, AR, vendor payments, payroll, and federal, state, and local tax compliance.

• Own the three-statement operating model, annual budget, and scenario planning for growth, profitability, and headcount.
• Deliver the monthly financial package to the CEO and Board: P&L, cash flow, variance analysis, and proactive recommendations.
• Prepare Board materials: actuals vs. budget, key business drivers.
• Serve as a key operator, galvanizing the team toward achievement of OKRs.
• Own LTV/CAC and payback analyses by acquisition channel and distribution segment.
• Support technical integration of financial data across company wide systems to help department heads understand and manage their budgets, and make the ROI of initiatives visible in real time.

• Own the mix of in-house staff and outsourced contractors. You have authority to restructure, replace, or bring work in-house, and you are expected to do so only when it lowers total cost or materially improves speed and accuracy.
• Every financial decision is rooted in a defensible, data-driven case: current fully loaded cost, proposed cost, what is the range of outcomes and their probabilities, and payback periods.
• Select and administer the finance systems stack (Quick Books Online, Brex, payroll and PEO, banking, billing) with a bias toward automation over headcount.

• Compensation and equity: comp modeling and leveling, developing Compensation Committee materials, optimizing incentive structures to align with company OKRs, preparing hiring plans including role scoping and ROI pressure-testing, and ensuring cap table accuracy in Carta, in partnership with HR and counsel.
• Legal and risk: corporate, commercial, and employment matters that intersect with finance; state registrations and compliance tied to payroll and operating presence.
• Commercial partnerships: financial terms, revenue share structures, and partner economics alongside the CEO, Chief Product Officer, and Partnerships lead. Additionally, you are eager to help lead business development initiatives as an externally-facile member of the team.
• Data and analytics: work with the Data team to connect product, marketing, sales, and financial data in Mixpanel and Tableau, building dashboards the whole company trusts.
• Company…