Headway Opportunities

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 TEAM & ROLE: One of the most overwhelming parts of finding a therapist comes after you've already shared what you're looking for: asking "which one of these qualified providers is actually right for me?" and deciding who to dive deeper with. You'll design the search results page and the provider cards on it: how results are tiered, what a card says and in what order, how we explain why this person was picked for you, what happens when there are only two options instead of forty. You'll work inside the Patient Onboarding pod with a Staff Product Designer, a PM, an engineering manager, and a researcher, and closely with the team that computes provider relevance. The work is fast and it is measured. This pod runs live experiments continuously, so you'll see patients respond to your decisions in days. You'll be expected to iterate on a shipped surface for weeks at a time rather than designing something once and handing it off, and to hold a high craft bar while doing it. Our design team works AI-first. Designers use Claude Code and Cursor to prototype, ideate, and ship improvements to our codebase. We want designers who already work this way and treat AI as a primary part of their practice. YOU WILL:

• Own design for the patient search results experience: results tiering, provider cards, match explanations, filters and sort, and the sparse and empty states that can dissuade someone from care.
• Design and run sustained experiments on a conversion-critical surface: frame the hypothesis, design the variants, read the results, and decide the next iteration.
• Shape how a provider's style and experience get expressed to a patient, partnering with the Ranking team on what signal exists and with the Profiles team on where it leads.
• Bring a point of view on what search results should become, and turn it into shippable increments with your PM and EM.
• Work directly with research and data to understand why patients hesitate, run research yourself when needed, and design for the patient who genuinely does not know what they want yet.
• Raise the craft bar on one of Headway's highest-traffic patient surfaces, and evolve our design system where it does not yet meet our needs.
• Prototype in code and AI tools so the team can react to something real instead of a static mock. YOU'D BE A GREAT FIT IF:
• You have 5-8 Years of experience designing consumer products, with end-to-end ownership of a live surface people use every day.
• Your portfolio shows mature, shipped craft on something dense and information-heavy.
• You have iterated on a conversion-critical surface over months and can talk honestly about what failed and what worked.
• You are comfortable with numbers and skeptical of them: you can say what you'd measure and also what that measure would miss.
• You have opinions about what to remove. On a page whose core problem is too much choice, restraint is the craft.
• You partner with PM and engineering as peers, share work before it is finished, and hold a position under pressure without getting brittle.
• AI tools are already part of how you work. You can say where they helped, where they were wrong, and what you overrode.
• Experience with marketplaces, search, discovery surfaces, or healthcare is a bonus rather than a requirement. Compensation and Benefits: The expected base pay range for this position is $180,000 - $225,000, 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. https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf 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 http://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.