Head of Finance

About the Company

We believe it should be easy for pet parents to do the right thing. At Pawlicy Advisor, personalized advice from the most trustworthy experts ensures pets get the best care possible.

Pawlicy Advisor is a fast-growing, venture-backed startup focused on helping pet owners around the country find the right health products for their pets, starting with pet health insurance. Pet insurance’s popularity is growing rapidly as pet owners seek protection from the high cost of veterinary care. Our pet insurance marketplace takes into account a pet’s breed-specific health risks to help people find the right policy for their pet. We also save pet owners money by analyzing pricing differences and premium increases over the lifetime of an animal.

We market to pet parents through a number of channels, but the partners we value the most are veterinarians. Vets love pet insurance because it increases that chance a pet parent will be able to afford the cost of treatment, but vets don’t know what providers to recommend and don’t want the liability associated with recommending a specific brand. Pawlicy Advisor helps thousands of vet offices across the US by simplifying the treatment financing conversation.

About the Role

Pawlicy Advisor is seeking a Head of Finance to own all Finance and Accounting. You will serve as a key operating partner to the CEO as well as other company leaders of this growing and profitable business. You will report directly to the CEO, and build a small, high-caliber team of up to two direct reports immediately.

Location:  New York City (full time position, in-office required with the CEO four days per week)

Responsibilities

Finance, Accounting, and Control

• Own the full finance stack: accounting, FP&A, controllership, AP, and treasury

• Build and manage a lean internal team (up to two immediate hires) and oversee outsourced finance contractors as you bring capabilities in-house
• Ensure a timely, accurate monthly close and maintain GAAP-compliant financials
• Maintain and refine the chart of accounts; align Brex coding and other systems with the GL
• Oversee AR and AP, vendor payments, and billing processes, including partnership revenue programs in collaboration with Product and Marketing
• Oversee payroll and incentive planning in coordination with HR
• Manage tax preparation and filings with external tax firms; ensure federal, state, and local compliance

Operating Model, FP&A, and Reporting

• Own the company operating model: three-statement forecasting and budget
• Proactively identify, evaluate, and recommend capital allocation opportunities
• Lead financial scenario planning and financial performance evaluation for each distribution channel
• Deliver monthly financial packages to the CEO: P&L, cash flow, variance analysis, and clear commentary and recommendations
• Help lead Board slide and supplementary strategic material preparation, preparing actuals vs. budget and key business drivers ahead of each meeting
• Run and maintain LTV/CAC and payback analyses by acquisition channel and by key distribution subsegments 
• Maintain recurring revenue models and update the estimated value of recurring book of business
• Support department Heads in understanding and managing their budgets; highlight ROI of initiatives and tradeoffs in real time.
• Work with Data team to build financial dashboards

Strategic Finance, Capital, and Partnerships

• Lead scenario planning for growth, profitability, and headcount.
• Help lead financial and strategic negotiations with commercial partners, growing key external relationships alongside CEO and Partnerships leader.
• Support capital strategy: assess cash flow and analyze and recommend opportunistic equity vs. debt options, covenant implications, and market conditions
• Own the financial workstream for strategic finance conversations: models, data room, and investor materials alongside in-house Counsel; partner with the CEO on investor conversations
• Evaluate strategic partnership and M&A opportunities, including synergy analysis, unit economics impact, and valuation considerations
• Maintain an up-to-date, investor-ready data room and core metrics dashboard

HR, Compensation, and People Systems (in partnership with HR)

• Own compensation modeling, including geographic and job leveling (cash and equity)
• Support Compensation Committee preparations, materials, and calibration
• Maintain the cap table. Ensure Carta is accurate and fully reconciled to closing docs, offer letters, Board approvals, and signed option agreements
• Partner on performance-based bonuses and incentive programs; ensure payouts are accurate, timely, and clearly communicated
• Collaborate on hiring plans, role scoping, and ROI of new hires; pressure-test comp and incentives before job listings launch

Legal, Compliance, and Risk Stewardship

• Partner with internal and external counsel on corporate, securities, employment, and commercial matters that intersect with finance
• Help manage company risk posture across financial, legal, competitive, and reputational categories alongside Legal and Operations leaders.
• Oversee business registrations and ongoing state and local compliance, especially as it relates to payroll, tax, and operating presence
• Coordinate with insurance counsel and HR Manager on any finance-relevant regulatory workflows (insurance licensing, training records, etc.).
• Ensure business policies, terms and conditions, and employee-facing documents align with our financial and risk posture
• Monitor any debt covenants and keep leadership informed of headroom and risk

Operations, Analytics, and Business Performance

• Identify critical issues to and opportunities for achievement of companywide OKRs weekly and bring structured, data-driven recommendations to the CEO and executive team.
• Collaborate with Data team to use BI and analytics platforms (e.g., Mixpanel, Tableau) to connect product, marketing, sales, and financial data
• Develop and maintain attribution frameworks and understand how attribution impacts reported performance and investment decisions
• Help lead company-level and departmental OKR achievement with clear metrics, baselines, and tracking, and identification of opportunities for more efficient company execution 
• Help design and refine processes that keep the company running cleanly: vendor management, tool selection for finance/ops, and cross-functional workflows

What Success Looks Like

• You are an exceptional communicator, a leading ClickUp user, and demonstrate high agency in your proactive approach to company strategy execution and daily operations. You don’t just report on financial data – you harness it always for optimizing the speed and execution of OKRs across the team. 
• The CEO and Board receive concise, accurate, and insightful financial packages that drive decisions, not just report history, and clearly articulate the progress the business is making toward predictable scalability
• Department leaders understand their numbers, trust the data, and make better choices because of you
• The company knows its LTV/CAC and payback, believes the numbers, and uses them to allocate capital
• The hiring plan, budget, and cash runway are always reconciled and forward-looking, not backward-facing
• Human capital decisions are made with consistency, efficiency, and precision
• Strategic opportunities (partnerships, capital raises, M&A) are evaluated quickly with rigorous analysis and clear recommendations

• 10+ years of experience in senior finance role(s) (Director/VP-level and above)
• 5+ years serving as finance executive or deputy finance manager (second-in-command or above) at a venture-backed startup
• Proven experience scaling a post-Series A startup, including raising capital for venture-backed startups
• Familiarity with B2B2C go-to-market
• Proven track record of building, managing, and developing a small team
• Deep FP&A and three-statement modeling experience; fluency in scenario analysis, unit economics, and sensitivity modeling
• Hands-on experience with accounting, budgeting, and monthly close, working with or overseeing controllers and external accounting firms
• Strong background in LTV/CAC analytics, payback period analysis, capital allocation, and channel performance measurement
• Experience raising capital for mid-stage venture-backed companies (equity and debt)
• Experience collaborating directly with Board members and venture firms, including developing clear Board-level reporting
• Comfort working across HR, legal, and operations topics, even when they fall outside finance
• Strong systems orientation; experience with tools such as QuickBooks Online, Brex, banking platforms, PEOs, Mixpanel, Bill.com (or analogous platforms)
• Demonstrated ability to operate with high urgency and ownership, and galvanizing a large team
• Based in the New York City area, with willingness to work in person with the CEO and team at least four days a week in Midtown Manhattan
• Legally authorized to work in the United States without sponsorship

How You Work

• You are a clear, direct communicator who can distill complexity into simple, actionable narratives
• You have a bias for action and move from analysis to decision and execution very quickly
• You are exceptionally organized, thriving on documenting your work as a means of communicating with and collaborating effectively with colleagues. You believe deeply that digital task management tools are extremely high value-add and require rigorous daily use
• You are comfortable challenging assumptions and being challenged in return
• You uplift others by making the financial picture understandable and useful to non-finance colleagues
• You enjoy being hands-on, close to the details, and wearing multiple hats in a lean environment

• Competitive salary (base $175,000 - $250,000) with performance-related bonus
• Startup equity grants
• Flexible vacation
• Top-tier Health, Dental, Vision insurance
• 401k employer contributions
• The chance to help grow a massive business that will help the veterinary industry thrive

If you’re excited to build and run the financial engine of a profitable, mission-driven company—and to act as a true partner to the CEO and executive team—we’d like to talk. You can learn more about us at https://www.pawlicy.com/about-us/