Head of Finance

Pawlicy Advisor

2h • $185,000 - $250,000 • Remote

About The Position

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.

Requirements

• 7+ years in finance, including 2+ years as the second-in-command (Director or VP reporting to a CFO or founder) at a venture-backed company.
• Hands-on ownership of the 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 a multi-channel or B2B2C business.
• Proven experience scaling a startup through a period of 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 such as Mixpanel or Tableau.
• Comfort working across HR, legal, and operations topics that fall outside traditional finance.
• Legally authorized to work in the United States without sponsorship.
• 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 (will use ClickUp daily for task management and AI tools such as Claude to compound your output) 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, including your own team, like any other investment: clear hypothesis, measured payback, and learnings that feed the next iteration.

Nice To Haves

• Preferred: familiarity with insurance distribution or commission-based revenue models.
• You are hungry to scale a company and have done high-paced operational work beyond finance.

Responsibilities

• 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 counterparty 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 companywide 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.
• Select and administer the finance systems stack (QuickBooks Online, Brex, payroll and PEO, banking, billing) with a bias toward automation over headcount.
• Partner on 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.
• Partner on legal and risk: corporate, commercial, and employment matters that intersect with finance; state registrations and compliance tied to payroll and operating presence.
• Partner on 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-facing member of the team.
• Partner with the Data team to connect product, marketing, sales, and financial data in Mixpanel and Tableau, building dashboards the whole company trusts.
• Contribute structured, data-driven recommendations on company OKRs and surface the highest-ROI opportunities and risks to the executive team.

Benefits

• Base salary $185,000 to $250,000, depending on experience and location.
• Target annual bonus tied to company and individual performance.
• Meaningful equity grant with a defined path to an executive title as the business scales.
• Top-tier health, dental, and vision insurance; 401(k) employer contributions; flexible vacation.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed