Senior / Staff Product Designer, Headway
Patient
$180-265k
+ Equity
Therapist-by-insurance marketplace
Posted today
Therapist-by-insurance marketplace
1001+ employees
Posted today
$180-265k
+ Equity
1001+ employees
Company mission
To build a new mental healthcare system, rewired for access and affordability.
Role
Who you are
- 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 consumer or patient-facing products where the quality of the experience directly affects whether people get help
- You're a systems thinker who can take a complex, state-heavy problem and shape it into a coherent, simple 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 patient-facing product surface from scratch, and you're comfortable when the requirements aren't written yet
- You've designed agentic or AI-powered workflows: conversational flows, intelligent recommendations, or replacing a manual step in the care journey with an AI-driven one
- You're a systems thinker who can hold a stateful, multi-actor patient experience 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
What the job involves
- We're hiring Senior and Staff Product Designers to own the patient 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
- Own the patient 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 moments that matter most in a patient's journey: finding a provider, understanding their benefits, booking an appointment, and staying engaged in care
- Run experiments with clear success metrics. You measure conversion, retention, and task completion, 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 patient surfaces and meaningfully improve what's already running at scale
- Design AI-native patient experiences: conversational flows, intelligent matching, and agentic care navigation 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 patient roadmap is part of the job
Our take
In the US, 1 in 4 citizens are living with treatable mental health conditions. But a vast majority of people are unable to access the care they need, often due to cost. Headway connects clients with therapists who accept insurance as payment, and provides independent practitioners with the tools and resources needed to both serve their patients and manage administrative workloads.
Headway’s concept is timely, with national mental health under particular strain following recent events. The company facilitates over 600,000 appointments per month and has attracted backing from the likes of Accel and Google Ventures. It is working to broaden its presence across the US while building out its product and pursuing the application of AI in health care.
Freddie
Company Specialist at Welcome to the Jungle
Insights
64% employee growth in 12 months
Company
Funding (last 2 of 6 rounds)
Jul 2024
$100m
LATE VC
Oct 2023
$125m
SERIES C
Total funding: $327m
Company HQ
Tribeca, New York, NY
Leadership
Andrew Adams
(Founder & CEO)Prior to founding Headway in 2017, Andrew was a Product Analyst at Spring Inc.
Salary benchmarks
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