Staff Product Designer, Design Systems

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

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