Head of Finance

Remote · 8+ years experience · Full-time · Remote · Posted Oct 1, 2026

At a glance

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 is looking for a hands-on, strategic finance leader to serve as Head of Finance.
The role involves owning accounting, financial operations, SaaS FP&A, and serving as a true partner to leadership.
The Head of Finance will define the path, make clear recommendations on where to invest and when to pull back, and drive execution with conviction.

Own the monthly close, P&L, balance sheet, cashflow, 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.
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.
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.

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.

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.