Similar Jobs at Headway
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 70,000 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, GV, 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.
This role sits at the intersection of patients, providers, and insurance, designing the billing and payment experiences that make Headway's financial engine feel simple, transparent, and trustworthy.
This is a complex, high-stakes design challenge. A single appointment at Headway touches insurance verification, claims processing, provider payouts, and patient billing — all with different timelines, edge cases, and failure modes. Today, confusion around billing is one of the top drivers of support tickets and a key factor in provider trust.
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’re already working this way and see AI as a primary part of their workflow.
In This Role, You Will- Own the end-to-end payment and billing experience across patients and providers. Navigate complexity with systems thinking. Payment flows touch insurance confirmation, claims, ERA ingestion, refunds, cancellation fees, and provider payouts. You'll map these dependencies and design experiences that absorb complexity rather than expose it.
- Start in planning mode, use tools like Claude.ai to clarify the problem space, understand data, and initial assumptions.
- Prototype with Claude Code/Cursor and MagicPattern to build and iterate on the 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 directly talk to customers to validate the solution for most of BAU projects with the research team’s support.
- Contribute to the design system and culture, share your AI practice, prompts, and patterns with the design team.
Compensation and 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.
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