Head of Product Design

Head of Product Design 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 an ... (truncated, view full listing at source)