Head of Finance

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-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 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.

• 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.
• Preferred: familiarity with insurance distribution or commission-based revenue models.
• Legally authorized to work in the United States without sponsorship.

How You Work

• 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 (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.

AI and the Hiring Process

We embrace AI at Pawlicy and our work still relies on what the humans bring to it.

Prep with AI all you like, but in the room, we want your thinking, your questions, and your judgment. These stages exist so we can get to know you and how you'd work with our team. We're hiring you, not a model and it is you we want to see.

To be concrete: no AI assistants or chatbots on any device during your interviews, and nobody else feeding you answers. If it turns out AI was used where we've asked you not to, it may end your candidacy.

If any part of our process is a barrier because of how you read, write or communicate, email View email address on click.appcast.io before that stage and we'll talk through the options. The skills we're assessing stay the same; what changes is the format. Asking has no bearing on how we assess you.

Interview Recording Notice

By submitting your application, you acknowledge that interviews with Pawlicy Advisor may be recorded (audio, video, and/or transcript) to support a fair and consistent hiring process. Recordings are used only for hiring purposes and are accessible only to those involved in the hiring decision. You will be asked to confirm your consent at the start of any recorded interview.

• 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.
• Remote-first, with regular in-person opportunities to collaborate with the CEO.

Career Path

This role is scoped as Head of Finance with a path to CFO. The promotion is tied to outcomes: consistent, high-quality execution and ownership across finance and operations resulting in achievement of company goals.

If you want to build and run the financial engine of a profitable, venture-backed, mission-driven company at an inflection point, and to act as a true partner to the CEO, Pawlicy would like to talk. Learn more at