Design Director, Core Insurance & Design Systems at Headway

This role is for a seasoned design leader with a specialized background in systems architecture and foundational product infrastructure. The ideal candidate has

Work type: remote

Location: New York, New York, United States; San Francisco, California, United States; Seattle, Washington, United States

Salary: $249,600 – $312,000/yr

Type: Full-time

Summary

This role is for a seasoned design leader with a specialized background in systems architecture and foundational product infrastructure. The ideal candidate has at least 3 years of management experience and a proven track record of scaling design systems, content design, and internal tools within a high-growth tech environment. You should be a "crafter" at heart who understands how to translate complex technical requirements into cohesive, high-quality user experiences. The compensation is highly competitive, ranging from **$212,000 to $265,000** plus equity. This is a fully remote position (within the US) at a well-funded, mission-driven Series D company. Notable perks include a "holiday break" week in December, therapy reimbursement, 16-week parental leave, and a dedicated work-from-home stipend. **You might be a good fit if you...** * Have built and managed multi-disciplinary teams of product, system, and content designers. * Are an expert in Figma and modern design system documentation and deployment. * Enjoy solving "backend" design challenges like insurance workflows and internal operational software. * Prioritize visual polish and "wildly predictable" user journeys over flashy, experimental UI.

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:





Experience we're seeking:






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.














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We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview.

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