Design Director, Core Insurance & Design Systems
HeadwayNew York, New York, United States; San Francisco, California, United States; Seattle, Washington, United StatesPosted 24 March 2026
Tech Stack
Job Description
Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.
1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.
Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.
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.
In this role, you will:
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.
Experience we're seeking:
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.
Compensation and Benefits:
The expected base pay range for this position is $ 249,600 to $312,000 , based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level.
We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential.
Benefits offered include:
Equity compensation
Medical, Dental, and Vision coverage
HSA / FSA
401K
Work-from-Home Stipend
Therapy Reimbursement
16-week parental leave for eligible employees
Carrot Fertility annual reimbursement and membership
13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st
Flexible PTO
Employee Assistance Program (EAP)
Training ... (truncated, view full listing at source)
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