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Headway

Director, Design (Provider)

Job Summary

This role is for a Design Director responsible for shaping the provider experience at Headway, a company building accessible mental healthcare systems. The candidate will lead the strategy, oversee high-quality design execution, and manage a talented design team. They will collaborate closely with product managers, engineers, and leadership to influence the product lifecycle from acquisition to retention. The position requires extensive experience in design leadership within B2B SaaS environments and a focus on building scalable systems and empowered teams.

Required Skills

B2B SaaS
Team Management
UX Design
User Experience
Product Design
Design Thinking
Design Leadership
Design Systems
Design Strategy
Design Execution

Benefits

Parental Leave
Flexible PTO
401K
Paid Holidays
Employee Assistance Program
Equity Compensation
HSA / FSA
Work-from-Home Stipend
Therapy Reimbursement
Fertility Benefits
Medical, Dental, and Vision coverage
Training and Professional Development

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 45,000 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.

About the role

As Design Director at Headway, you will work closely with product managers, engineers, and senior leadership to help providers grow and manage their practice with Headway. You’ll drive the provider experience vision, strategy, and own the execution of provider product design with a high craft bar that inspires senior designers. Your focus will encompass the entire provider lifecycle, from acquisition to engagement and retention.

Core Responsibilities

  • Drive provider experience strategy and vision - Partner with product managers, engineers, and senior leadership to define and execute the comprehensive provider experience strategy across the entire lifecycle from acquisition to retention.
  • Ensure high-craft design execution - Own the end-to-end design execution of provider products with exceptional attention to detail and craft quality that motivates senior designers
  • Grow and manage a high performing design team

Below are additional experiences we think help leaders succeed at Headway:

  • 5+ years leading design team for complex B2B SaaS platforms with consumer-grade UX
  • Experience with hyper-growth startups (Series C+) and larger companies with mature design practices. Know what good looks like for building an empowered design team.
  • Proven track record partnering with product managers, engineers, and leadership to drive experience vision and influence organizational direction through design thinking
  • Experience building scalable design systems for complex products while leading and mentoring senior design talent across multiple product areas
  • Portfolio demonstrating both high-craft individual work and systematic approaches to design at scale.
Compensation & Benefits:

The expected base pay range for this position is $255,000 - $300,000 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-EM1

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 employees work remotely across the US, with the option to work from offices in New York City, San Francisco and Seattle. Headway participates in E-Verify. To learn more, click here.

Interested in this job?

Application deadline: Open until filled

Logo of Headway

Headway

A platform connecting patients with mental health providers, simplifying access to therapy and psychiatric care.

See more jobs
Date PostedJuly 7th, 2025
Job TypeFull Time
LocationNew York, New York, United States; Remote; San Francisco, California, United States; Seattle, Washington, United States
Salary$255,000 - $300,000
Exciting remote opportunity (requires residency in United States) for a Director, Design (Provider) at Headway. Offering $255,000 - $300,000 (full time). Explore more remote jobs on FlexHired!

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