1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that.

But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens.

We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. 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

Every provider who joins Headway starts with onboarding — a multi-step credentialing process that collects licenses, CAQH data, NPI verification, payer enrollment, and more. Today, only ~20% of qualified providers make it from interest to their first appointment. That gap represents over $100M in unrealized annual revenue and, more importantly, tens of thousands of patients who can't access the care they need.

We're not looking to optimize the existing form. We're looking to replace it. This role will lead the design of an AI-agent-powered onboarding experience that fundamentally reimagines how providers join Headway — transforming a high-friction, multi-page credentialing flow into an intelligent, conversational experience that gets providers credentialed and seeing patients faster than they thought possible.

We're building an AI-first design team at Headway. Designers are expected to use AI tools like Claude, Cursor, and MagicPatterns to prototype and stay involved through launch and iteration directly in code. We're looking for designers who are already working this way and see AI as a primary part of their workflow.

In this role, you will:

Own the end-to-end provider onboarding experience from lead form submission through credentialing to first appointment. You'll be the design anchor for the Onboarding pod, partnering with PM and Eng to drive the biggest conversion lever in our provider funnel.
Design AI-agent-powered intake flows that replace manual, multi-page credentialing forms with intelligent interactions. You'll define what agentic onboarding looks like at Headway — new interaction patterns, trust signals, and automation boundaries that don't yet exist in our design system.
Scale our self-serve onboarding vision beyond v2. We've proven that product-led onboarding can dramatically improve conversion; you'll push this further, enabling providers to go from interest to credentialed with minimal human intervention.
Start in planning mode, using tools like Claude.ai to clarify the problem space, understand data, and test initial assumptions. Prototype with Claude Code/Cursor and MagicPatterns to build and iterate on flows and IAs. Let AI generate the pixels and code while you define the right patterns, behaviors, and quality. Partner with product & Eng to decide when to move into production.
Conduct research and talk directly to providers to validate solutions, with the research team's support. Understand why providers get stuck, what builds their confidence, and where automation helps vs. hinders.
Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.

You'll be a great fit if you:

Have 8+ years of product design experience, with significant time spent on onboarding, activation, or conversion-focused product work
Have shipped measurable conversion improvements — you think in funnels, know how to diagnose drop-off, and get excited when a design change moves a metric
Are a systems thinker who can reason about how a form redesign connects to CAQH, NPI, payer credentialing, and downstream provider activation — you design with awareness of the full pipeline
Have experience designing agentic or AI-powered workflows — conversational flows, intelligent automation, or replacing manual processes with AI-driven experiences (not just chatbots)
Bring strong visual and interaction design craft — you care deeply about the details and can produce polished, high-quality work at speed
Are comfortable with AI prototyping tools (Claude Code, Cursor, MagicPatterns) and see them as a core part of how you work
Want your work to make a meaningful difference in people's lives — this role directly impacts how many providers join Headway and how many patients get access to affordable mental healthcare

Compensation & Benefits:

The expected base pay range for this position is $212,000 - $265,000, 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 and professional development

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.

A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.