Design Director, Core Insurance & Design Systems
Quick Summary
1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people.
1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.
But we're going further. Over 70,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.
We're a Series D company with $325M+ in funding (a16z, Accel, GV, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better.
At Headway, our mission is to build a new mental healthcare system that everyone can access. Behind the magic for patients to find right and predictable care is our robust design system, insurance platform and internal tools.
As the Product Design Director for this team, you will help contribute to our mission by making Headway’s operation more efficient, by building a powerful design system, strategic content design, wildly predictable insurance experience and robust internal tools. In this role, you will lead and continue building a talented team of product designers, design system designers and content designers. You'll be a key partner to other teams, ensuring our design systems empower teams to build cohesive, high-quality experiences at scale.
- Lead the design systems across our products, as well as lead the team defining these systems. You will also be an advocate of design craftsmanship across our product, design, and engineering organizations.
- Oversee the foundational experiences including insurance experiences, support experiences and security experiences for our customers.
- Manage the internal tooling experiences that helps Headway operate efficiently.
- Hire, lead, and coach a team of design system designers, content designers, and product designers responsible for design systems and foundational experiences.
- 3+ years of experience leading successful design system or product design teams.
- Extensive experience in building and shipping design systems across a variety of systems.
- Experience building and scaling a design team.
- Great communication and excel in making complex technical details easy to understand.
- Value high quality visual design with attention to detail.
What We Offer
~2 min readListing Details
- Posted
- March 16, 2026
- First seen
- March 25, 2026
- Last seen
- April 21, 2026
Posting Health
- Days active
- 27
- Repost count
- 0
- Trust Level
- 31%
- Scored at
- April 21, 2026
Signal breakdown

We're building a new mental healthcare system. Tens of millions of Americans seek mental health care every day, but the vast majority never get the care they need. Headway is solving this, and we’re doing it all through software.
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