Head of Product Design at Freshpaint

ABOUT FRESHPAINT: 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. BACKED BY TOP INVESTORS Freshpaint is backed by some of the most respected names in technology, including: - Y Combinator (OpenAI, Stripe, Airbnb, Coinbase, DoorDash) - Intel Capital (Broadcom, Astera Labs, VMware, RedHat, MongoDB) We’ve raised tens of millions of dollars in funding to build the privacy infrastructure layer for healthcare’s digital future. WHO WE’RE LOOKING FOR We’re looking for a Head of Product Design who thrives in complexity and leads from the front. You are a player-coach who sets the bar for craft, speed, and strategic thinking by doing the work alongside your team. You have a track record of turning dense, data-heavy, and regulated workflows into intuitive, empowering experiences for non-technical users. You don’t rely on handoffs. You operate at the intersection of Product and Engineering, using design to shape what gets built and why. You’re outcome-obsessed, using data and rapid iteration to drive metrics like time-to-value and task success. You attract and develop top-tier design talent, coaching them to think like product owners and operate as strategic partners. WHAT YOU’LL BE DOING 1. LEAD AND SCALE (THE COACH) Build a world-class design function by hiring and mentoring designers who are missionaries, not mercenaries. You will establish a coaching rhythm that focuses on strategic thinking, identifying user friction early, and navigating technical trade-offs. Your goal is to foster a culture where designers are expected to participate deeply in the discovery process, not just the delivery process. 2. DIRECT IMPACT (THE PLAYER) Embed as the lead designer for a core product team, owning the end-to-end experience for high-stakes product areas. You will establish usability as a core, non-negotiable success metric. You will lead the charge in ensuring we validate our assumptions through rigorous, scrappy testing before we commit engineering resources. 3. STRATEGIC INFLUENCE Partner with the VP of Product and CPTO to shape the long-term vision of Freshpaint. You will set frictionless user experience and radical simplicity as the north star, then create tangible visions of the future that help the leadership team and the rest of the organization align on the most compelling version of the future possible. You will champion a data-informed culture by insisting on usage telemetry and using instrumentation to find and fix quiet usability issues. 4. SYSTEMS AND PROCESS Evolve our design system to prioritize speed, accessibility, and technical feasibility. You will implement continuous discovery habits, ensuring the team is in a constant dialogue with our users, including healthcare marketers and privacy specialists. You will leverage modern tools and AI-enabled workflows to accelerate the design-to-code pipeline. PRIMARY RESPONSIBILITIES - Build, hire, and mentor a world-class design team focused on strategic impact and risk mitigation - Act as lead designer on a core product area, owning end-to-end user experience for high-stakes workflows - Establish usability as a non-negotiable metric through rapid, scrappy testing and validation - Partner with Product and Engineering early to shape direction and de-risk product decisions before build - Define and drive a culture of continuous discovery and deep user engagement - Influence company strategy by creating clear, compelling product visions grounded in user needs - Use product telemetry and data to identify friction and continuously improve experience quality - Evolve and scale the design system to balance speed of assembly with technical feasibility - Leverage AI and modern tooling to accelerate design iteration and testing DESIRED SKILLS & EXPERIENCE - Pedigree of Complexity: 8+ years in Product Design, with a significant portion spent on complex B2B SaaS, data analytics, or healthtech platforms. - Leadership and Mentorship: Proven experience leading or mentoring other designers, with the ability to show how you helped them grow their strategic impact. - The Startup Gear: You’ve excelled in high-growth, resource-constrained environments where you had to be scrappy to get the right answers. - Technical Literacy: You understand the feasibility leg of the stool. You can speak the language of engineers and understand how data structures impact the user experience. - Discovery-Native: You have a deep, practical toolkit for user research and rapid prototyping. You know how to get a signal on an idea in hours or days. - Data-Informed Mindset: You are comfortable using metrics and telemetry to guide decisions and move from features to outcomes. NICE TO HAVES - Experience in healthcare, privacy, or highly regulated domains - Familiarity with data pipelines, analytics tools, or marketing technology ecosystems - Experience building or scaling design systems in growing organizations - Exposure to AI-enabled design or development workflows - Experience partnering closely with executive leadership on long-term product vision 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 - 16 weeks fully paid parental leave (eligible after 6 months; commission-based roles receive 100% base salary during leave) - 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 - Intentional & engaging company offsites 2x a year (past trips: Arizona, Jackson Hole, Cabo, Nashville, New Orleans & more) + a department offsite 1x per year And more! Check out our careers page [Upgrade to PRO to see link] for the full list.