Senior / Staff Product Designer

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 90,000 providers across all 50 states run their practice on our software, serving over 2.6 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, and building much of it with AI. 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 THIS ROLE

We're hiring Senior and Staff Product Designers to own the provider experience at Headway. The work calls for strong craft, sharp product instincts, deep customer obsession, and real fluency in an AI-native environment where prototyping in code is core to the role.

Senior designers bring 5+ years of experience and a track record of owning complex surfaces end to end. Staff designers bring 8+ years, span both 0→1 and at-scale work, and shape how the broader team operates. Both levels partner closely with PMs, engineers, and researchers, and own the outcomes their team ships.

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.

THE PROBLEM WE'RE SOLVING

Therapists lose hours to credentialing, documentation, scheduling, and billing. We're using AI to take that work off their plate and give them more time with patients. Our mission is to help providers build a thriving practice on Headway that practically runs itself, on product surfaces that are fast, reliable, and a delight to use.

YOU WILL…

• Own the provider product experience end to end, from problem framing through launch and iteration. You're the primary design voice on your team.

• Prototype and test ideas quickly with Claude Code, Cursor, or your AI tool of choice. AI generates the pixels and prototype. You define the patterns, behaviors, and quality bar.

• Partner closely with product managers, engineers, and researchers. You shape what gets built, including scope and priority.

• Design for the workflows providers live in every day: credentialing, scheduling, clinical documentation, and billing. You’ll make complex, high-stakes tasks fast and reliable.

• Run experiments with clear success metrics. You measure task completion, error rates, and provider satisfaction, and you treat a negative result as a finding.

• Contribute to Helix, our design system, and share your AI prompts and patterns with the broader design team.

At the Staff level, you'll also:

• Lead both 0→1 and at-scale work. You’ll launch new provider capabilities and meaningfully improve what's already running at scale.

• Design AI-native provider experiences: agentic documentation, intelligent billing automation, and workflows that replace manual processes outright.

• Set the standard for AI-native practice on the design team. You prototype in code and stay involved through launch.

• Mentor other designers, raise the craft bar, and shape how the design org works through critique, design system contributions, and shared practice.

• Influence product direction with design rationale, research, and storytelling. Shaping the provider roadmap is part of the job.

YOU'LL BE A GREAT FIT IF…

Senior:

• You have 5+ years of product design experience, with a portfolio that shows strong craft, structured thinking, and measurable business impact.

• You have experience designing B2B or professional tools where users are experts who need efficiency and reliability, not hand-holding.

• You're a systems thinker who can take a complex, state-heavy problem and shape it into a coherent experience.

• You bring product strategy instinct. You shape what to build from customer insight and bring your own point of view to the roadmap.

• You're fluent in experimentation. You've run multi-sprint experiment arcs against real metrics, and you design each round to teach you something.

• You're fluent with AI prototyping tools and treat them as core to how you work.

• You're motivated by Headway's mission of making mental healthcare accessible and affordable.

Staff (all of the above, plus):

• You have 8+ years of product design experience, with a portfolio that shows exceptional craft, systems thinking, and measurable business impact.

• You've done real 0→1 work. You've defined a provider-facing product surface from scratch, and you're comfortable when the requirements aren't written yet.

• You've designed agentic or AI-powered workflows: clinical documentation, intelligent billing, or replacing a manual provider process end to end with an AI-driven one.

• You're a systems thinker who can hold a stateful, multi-actor provider workflow in your head and design with awareness of the full pipeline.

• You've elevated the designers around you through mentorship, critique, or the quality of your own work.

Compensation

The expected base pay range for this position is $180,000 - $225,000 (Senior) & $212,000 - $265,000 (Staff), 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.

Comprehensive benefits:

Medical, dental, vision, HSA/FSA, 401(k) including match for 2027!, Carrot Fertility reimbursement, and paid parental, medical and caregiver leave.

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.

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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.