[Hiring] Head of Product Design @Freshpaint

Role Description

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

• Lead and Scale (The Coach)
  • Build a world-class design function by hiring and mentoring designers who are missionaries, not mercenaries.
  • Establish a coaching rhythm that focuses on strategic thinking, identifying user friction early, and navigating technical trade-offs.
  • Foster a culture where designers participate deeply in the discovery process, not just the delivery process.
• 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.
  • Establish usability as a core, non-negotiable success metric.
  • Lead the charge in ensuring we validate our assumptions through rigorous, scrappy testing before we commit engineering resources.
• Strategic Influence
  • Partner with the VP of Product and CPTO to shape the long-term vision of Freshpaint.
  • Set frictionless user experience and radical simplicity as the north star.
  • Create tangible visions of the future to help the leadership team and the organization align on the most compelling version of the future possible.
  • Champion a data-informed culture by insisting on usage telemetry and using instrumentation to find and fix quiet usability issues.
• Systems and Process
  • Evolve our design system to prioritize speed, accessibility, and technical feasibility.
  • Implement continuous discovery habits, ensuring the team is in constant dialogue with our users, including healthcare marketers and privacy specialists.
  • 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.

Qualifications

• 8+ years in Product Design, with a significant portion spent on complex B2B SaaS, data analytics, or healthtech platforms.
• Proven experience leading or mentoring other designers, with the ability to show how you helped them grow their strategic impact.
• You’ve excelled in high-growth, resource-constrained environments where you had to be scrappy to get the right answers.
• You understand the feasibility leg of the stool and can speak the language of engineers.
• You have a deep, practical toolkit for user research and rapid prototyping.
• 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.

Benefits

• 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).
• And more!