Head of Finance

About this role

Location: Remote, US-based. Full time. Remote within the Eastern or Central time zones, with a preference for the NYC metro area. The work schedule is Eastern business hours. Travel to meet with the CEO in NY is expected, and is tied to the work need and opportunity.
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.
What You Own
Cash Management and Banking Relationships

• 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.

Accounting, Close, and Control

• 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.

Operations, FP&A, and Board Reporting

• 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.

Finance Operating Model and Team

• 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 (QuickBooks Online, Brex, payroll and PEO, banking, billing) with a bias toward automation over headcount.

Where You Partner

• 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-facing 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 execution: contribute structured, data-driven recommendations on company OKRs and surface the highest-ROI opportunities and risks to the executive team.

What Success Looks Like
First 90 days

• Monthly close delivered on a defined schedule with a documented review process. You can explain every material line.

• Operating Model (forecast) is live, updated with actuals, and reviewed monthly.

• Become expert on company’s market, strategy, and operations.

• Audit of current financial workstreams complete, with scoped processes for completing needed workstreams and defined plan regarding contractors and bringing capabilities in-house.

• Transaction-ready data room with updated diligence materials.

• Support 2027 budget development as part of Operating Model build.

First 12 months

• The CEO and Board receive concise, accurate packages that drive decisions and show progress toward scalable growth.

• Channel-level LTV/CAC and payback are published, trusted, and used by department heads to allocate capital.

• Budget, hiring plan, and cash runway are always reconciled and forward-looking.

• Strategic opportunities are evaluated in days with rigorous analysis and a clear recommendation.

• Maintain active operational presence across the company, partnering on OKR development and guiding the business toward achievement of its OKRs.

Requirements

• 7+ years in finance, including 2+…