Head of Product Design

Freshpaint

3d • Remote

About The Position

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.

Requirements

• 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

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

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) + a department offsite 1x per year
• And more! Check out our careers page for the full list.

What This Job Offers

• Job Type: Full-time
• Career Level: Executive
• Education Level: No Education Listed