Staff Product Designer, Design Systems

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.

Headway is building a new mental health care system that everyone can access. We're a three-sided marketplace connecting patients, therapists, and insurance companies—making it easy for therapists to accept insurance and easy for patients to find quality, in-network care.

You'll be the first dedicated Design System Designer at Headway, reporting into our Design Director, Foundations. Your work enables our design and product teams to move fast while maintaining craft and coherence across a complex, multi-sided platform.

You'll partner closely with the Web Platform team, supporting Product and Brand development to ensure the system is both flexible and opinionated, empowering teams to ship with confidence while keeping quality high.

What you'll do:

• Scale Headway's existing design system from its current state into a robust, well-documented system that serves patients, providers, and payers.
• Define the principles, patterns, and components that enable consistent, high-quality experiences across web and mobile platforms.
• Partner with Creative team to ensure the design system reflects and amplifies Headway's identity across all touchpoints.
• Collaborate with Engineering to ensure components are built for reusability, accessibility, and performance.
• Establish governance models and contribution frameworks so teams can extend the system without breaking it.
• Educate and enable product teams to use the system effectively—through documentation, office hours, and hands-on partnership.
• Balance the needs of three distinct audiences while maintaining a unified Headway experience.
• Identify gaps, inconsistencies, and opportunities to improve the system as the product evolves.

What we're looking for

• 8+ years of experience in product design, with significant focus on design systems.
• Deep expertise building and scaling design systems in complex, multi-product environments.
• Strong systems thinking—you see patterns, anticipate edge cases, and design for scale.
• Fluency in designing for accessibility, responsiveness, and technical constraints.
• Experience partnering with Engineering to build and maintain component libraries.
• A collaborative mindset—you enable others to do their best work.

Compensation & Benefits:

The expected base pay range for this position is $215,000 - $254,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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 and professional development

#LI-RJ1

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.

Headway participates in E-Verify. To learn more, click here.