Head of Finance

Healthcare is a $4+ trillion industry in the U.S. alone, and it’s undergoing a rapid digital transformation. Hospitals, digital health companies, and life sciences organizations rely on analytics and advertising tools to reach patients, measure performance, and grow. But those tools weren’t built for regulated healthcare data. That creates real compliance risk and forces teams to choose between growth and privacy.

Freshpaint eliminates that trade-off. We’re a privacy-first data platform that helps healthcare organizations use modern marketing and analytics tools without exposing protected health information (PHI). Freshpaint sits between a company’s website or app and the third-party tools they use, automatically detecting and controlling sensitive data before it’s shared.

In short: we let healthcare teams move fast, safely.

Who we’re looking for

We're looking for a hands-on, strategic finance leader to serve as Freshpaint's Head of Finance. You've owned accounting, not just FP&A: you've run the monthly close, owned the P&L, balance sheet, cash flow, and ideally taken a company through an audit. You also bring the SaaS FP&A chops and commercial instincts to be a true partner to leadership. You don't wait to be told what the business needs: you define the path, make clear recommendations on where to invest and when to pull back, and drive execution with conviction. You're a doer who builds lean, scalable systems, thrives on turning ambiguity into structure, and is hungry to grow your visibility with our board and investors.

What you’ll be doing

As Freshpaint's Head of Finance, you'll own the finance function that powers our next stage of growth. Reporting directly to the CEO, you'll run day-to-day finance operations, from the books and monthly close to designing how we plan, budget, forecast, and measure the business. We've moved from a marketing-led to a sales-led GTM motion, so you'll play a central role in how we invest in growth, pressure-test our commercial economics, and manage runway. Over time, you'll build a strong presence with our board and investors as we prepare for what's next. This is a highly visible, hands-on role for a finance operator who wants to shape how a company runs, not just report on it.

Primary Responsibilities

Financial operations & accounting

• Own the monthly close, P&L, balance sheet, and cash flow, and ensure accurate, timely financial statements.
• Maintain strong controls and audit readiness across accounting, revenue recognition, tax, and treasury.
• Manage our day-to-day finance team and external accounting partner, keeping the finance org lean and high-leverage.
• Design and operationalize our financial operating model: processes, systems, reporting cadences, and budget ownership across teams.

Strategic planning & FP&A

• Own annual planning, budgeting, and rolling forecasts, with clear budget owners, org ratios, and spend guardrails.
• Build and maintain scalable, driver-based financial models that support scenario planning, hiring plans, and long-term strategy.
• Drive operational discipline around spend, cash flow, and runway management.
• Partner with GTM leadership on comp plans, capacity planning, pricing guardrails, and unit economics, challenging the commercial economics as we scale a sales-led motion.

Executive partnership & board

• Serve as a trusted thought partner to the CEO and exec team, giving data-driven recommendations on investments, trade-offs, and pacing of growth.
• Deliver clear, decision-ready reporting on the core SaaS metrics that leadership relies on.
• Grow into ownership of board and investor reporting, and support fundraising preparation and potential strategic processes when the time comes.

Desired skills & experience

• 8+ years of progressive finance experience, including leadership roles at high-growth B2B SaaS startups or scale-ups (ideally Series A–C).
• Hands-on accounting ownership: you've run the monthly close and owned the balance sheet and income statement, ideally through a controller role or Big 4 audit experience.
• Experience taking a company through an audit.
• Strong command of SaaS metrics, subscription economics, financial modeling, forecasting, and scenario planning.
• Experience partnering with GTM leaders on commercial economics, comp design, and pricing.
• Proven experience partnering directly with CEOs and executive teams.
• Ability to simplify complex financial concepts and influence non-finance stakeholders.
• High ownership and sound judgment. Comfortable rolling up your sleeves and making decisions with imperfect information in a fully remote, fast-moving environment.

Nice to haves

• CPA.
• Experience with board reporting, investor updates, or supporting a fundraise or M&A process.
• Experience supporting a shift from a product- or marketing-led motion to a sales-led or enterprise GTM motion.
• Healthcare, health tech, or other regulated-industry SaaS experience.
• Hands-on experience implementing finance tools, e.g. an ERP/GL, billing, FP&A software, or spend management.

Perks & Benefits

• Competitive pay + generous equity
• Half-day Fridays, every Friday
• 16 weeks fully paid parental leave (eligible after 6 months; commission-based roles receive 100% base salary during leave)
• Flexible PTO with a required 2-week minimum
• Top-tier health, dental & vision (100% covered for you, 80% for dependents)
• Intentional & engaging company offsites (past trips: Arizona, Jackson Hole, Nashville, New Orleans & more)