About Freshpaint:

Customer data is the fuel that drives all modern businesses. From product analytics, to marketing, to support, to advertising, advanced data analysis in the warehouse, and even sales – customer data is the raw material for each function at a modern business.

For highly regulated businesses in healthcare, it’s always been a challenge to harness that customer data and get it to the marketing and analytics tools that require it while following patient privacy laws….until now.

Something as simple as running ads to get more users is simple for an e-commerce of software company to do. But common web analytics and advertising tools collect sensitive user identifiers and healthcare information automatically. Those same tools are not HIPAA compliant.

We provide a layer of data governance to make current web analytics tools HIPAA-compliant. For analytics, our customers can continue getting the insights they need to improve the patient experience. For marketing, Freshpaint safeguards health information while helping our customers promote access to care through popular advertising platforms like Facebook, Google, and others.

In short, we help healthcare marketers promote access to care and safeguard patient privacy at the same time. This is an important, complex problem in a massive market (healthcare is 20% of the US GDP).

Our customers manage their customer data with:

1. Privacy Platform. We help healthcare providers automate their website’s + app’s HIPAA compliance, and safeguard patient data. This is our core product today

2. Future additional product lines! Our core product provides a platform that we're building marketing applications on top of.

We’re fully remote. If you strongly value in-person work, Freshpaint is likely not the best fit for you. Even though we don’t care where you’re located, we only hire within the US. Many of our team is concentrated in various metro areas like SF or NYC. To balance out our remote-ness, we gather the team 2x times per year for offsites. We’re backed by leading investors including Y-Combinator, Intel Capital, and angel investors like the Head of Data from Slack, Head of Data at LinkedIn, and more.

Who we are:

Freshpaint was founded by web analytics veterans who realized how hard it was for highly regulated companies to collect and use customer data in a compliant way. We started as part of Y Combinator’s S19 cohort and have been focused on enabling healthcare companies collect, safeguard, and activate patient data since.

In 2022 the government issued updated guidance around HIPAA, basically making our software a requirement to use for healthcare companies. As a result, we're one of the fastest growing software companies on earth right now.

Our team has deep analytics and growth experience, with all of us coming from high-growth companies like Heap, Pendo, Iterable, Quantum Metric, and Retool. If you value lots of freedom and ownership in your work, interfacing with customers, and working on a product with high customer impact, then Freshpaint is your home.

About the Role

We’re looking for a strategic executor – a Head of Finance who not only understands the financial landscape, but knows how to drive the business forward. This is not a “tell us what you need and we’ll make it happen” role. We need someone who defines the path, sets the financial strategy, and executes decisively.

You will be the company’s financial architect: designing systems, processes, models, and operational rhythms that enable us to scale with clarity and confidence. You will partner closely with leadership to make informed decisions, but more importantly, you will lead with conviction and tell us how to do things, not the other way around

What You’ll Do

• Own all financial strategy, planning, forecasting, and analysis with a strong bias toward clear, decisive execution.

• Design and operationalize the company’s financial infrastructure—processes, systems, reporting cadences, and the overall financial operating model (how we budget, plan, track, measure, and adapt).

• Develop and maintain scalable financial models that support strategic decisions, scenario planning, and long-term planning.

• Create operational discipline around budgeting, runway management, spend, and cash flow optimization.

• Provide leadership with data-driven guidance on investments, trade-offs, pacing of growth, and when/where to pull back.

• Evaluate key cross-functional initiatives (Product, GTM, Operations) and provide strategic, actionable financial recommendations.

• Ensure compliance, strong financial controls, and accurate reporting across accounting, FP&A, tax, audit, and treasury.

• Partner closely with the CEO and executive team to align financial strategy with company priorities and drive execution.

• Translate financial insights into clear, actionable recommendations for the leadership team and board.

• Support fundraising, investor reporting, and potential M&A processes.

• Build and scale a small but high-impact finance team over time (FP&A essential; accounting/controller experience a plus).

What We’re Looking For

Experience & Background

• 8–12+ years of progressive finance experience, including leadership roles in high-growth startups or scale-ups (ideally Series A–C).

• Proven ability to partner directly with CEOs, founders, and boards in fast-moving environments.

• SaaS experience is a must, with a strong grasp of SaaS metrics, unit economics, subscription dynamics, and operational levers.

• Experience managing fundraising, investor reporting, and/or M&A is a significant plus.

Strategic Executor Profile

• Squarely in the strategic executor zone. You articulate the how, not just the what.

• Has a clear vision for how finance should operate at a high-growth startup, grounded in practicality rather than theory.

• Able to design lean, effective systems that drive operational and financial execution.

Skills & Capabilities

• Strong command of financial modeling, forecasting, scenario planning, and metrics-driven decision making.

• Ability to simplify complex financial concepts for non-financial stakeholders.

• High ownership, high judgment, and a bias toward clarity, speed, and action.

• Proactive problem-solver who identifies gaps, proposes solutions, and executes without hand-holding.

Mindset & Operating Style

• Clear sense of what “good” finance looks like at startup scale.

• A self-starter who can turn ambiguity into structured systems and repeatable processes.

• Practical, resourceful, and fast-moving. Someone who gets things done.

Management & Team Leadership

• Experience managing managers or leading small, high-impact teams.

• Comfortable overseeing a lean finance org (FP&A essential; accounting/controller experience a strong bonus).

• Not an empire builder. Motivated to run a small, efficient, high-leverage team.

Who You Are

• A practical strategist with strong execution instincts. Someone who sees around corners and then builds the plan to address what’s coming.

• A doer who rolls up their sleeves, bringing structure, rigor, and accountability to the organization.

• A leader who provides direction, not just analysis, and drives alignment across teams.

• Someone who creates order, clarity, and repeatability in how we operate.

• Comfortable making decisions with imperfect information and moving quickly.

• Energized by building, improving, and scaling without adding unnecessary complexity.

Perks & Benefits

We take care of our team—here’s a peek at what you get when you join:

• Competitive pay + generous equity (10-year exercise window)

• Fully remote (U.S. only) with a $150/month coworking stipend

• Half-day Fridays, every Friday

• Unlimited PTO—with a required 2-week minimum

• Top-tier health, dental & vision (100% covered for you, 80% for dependents)

• 2 “Treat Yourself” days a year—$100 and a day off, just because

• Generous parental leave

• Epic offsites twice a year (past trips: Greece, Jackson Hole, Cabo, wine country + more)

And more—check out our careers page for the full list.