Senior / Staff Product Designer - Patient

Headway•New York, NY

2d•Remote

About The Position

Headway's mission is to build a new mental healthcare system that everyone can access by solving the biggest barrier to care: insurance. We have automated the administrative work involved in credentialing, claims, and payment reconciliation. Over 75,000 providers across all 50 states use our software, serving over 1 million patients. We are developing the best tools for therapists to manage their practices, reimagining the process of finding a therapist, and building the platform foundations for scalability. We are more than just a billing solution; we are becoming the platform where care is delivered. As a Series D company with over $325M in funding from investors like a16z, Accel, and Spark Capital, we are seeking exceptional individuals to help us achieve our mission and make this the most meaningful experience of your career. Join us to help transform mental healthcare. We are hiring Senior and Staff Product Designers to lead the patient experience at Headway. This role requires strong design skills, sharp product intuition, deep customer focus, and fluency in an AI-native environment where prototyping in code is essential. Senior designers should have 5+ years of experience and a proven ability to manage complex product areas from start to finish. Staff designers should have 8+ years of experience, with expertise in both new product development (0→1) and scaling existing products, and should be able to influence the broader team's operational methods. Both roles involve close collaboration with Product Managers, Engineers, and Researchers, and accountability for the outcomes their teams deliver. Our design team operates with an AI-first approach, utilizing tools like Claude Code and Cursor for prototyping, ideation, and shipping code improvements. We are looking for designers who already embrace this methodology and consider AI a primary tool in their practice.

Requirements

5+ years of product design experience for Senior level, with a portfolio showcasing strong craft, structured thinking, and measurable business impact.
8+ years of product design experience for Staff level, with a portfolio demonstrating exceptional craft, systems thinking, and measurable business impact.
Experience designing consumer or patient-facing products where user experience quality directly impacts access to help.
Systems thinking ability to transform complex, state-heavy problems into coherent, simple experiences.
Product strategy instinct; ability to shape product direction based on customer insights and contribute a unique perspective to the roadmap.
Fluency in experimentation, including running multi-sprint experiment arcs against real metrics and designing each round for learning.
Fluency with AI prototyping tools, treating them as core to your workflow.
Motivation by Headway's mission to make mental healthcare accessible and affordable.
For Staff level: Proven experience with 0→1 product development, defining new patient-facing product surfaces from scratch.
For Staff level: Experience designing agentic or AI-powered workflows, including conversational flows, intelligent recommendations, or replacing manual care journey steps with AI-driven solutions.
For Staff level: Ability to hold a complex, stateful, multi-actor patient experience in mind and design with awareness of the full pipeline.
For Staff level: Experience elevating design teams through mentorship, critique, or high-quality work.

Nice To Haves

Prototyping in code is core to the role.
Treat AI as a primary part of your practice.
AI-native environment.
AI generates the pixels and prototype.
You define the patterns, behaviors, and quality bar.
You shape what gets built, including scope and priority.
You measure conversion, retention, and task completion, and you treat a negative result as a finding.
You prototype in code and stay involved through launch.
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.
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.
You've done real 0→1 work.
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've elevated the designers around you through mentorship, critique, or the quality of your own work.

Responsibilities

Own the patient product experience end to end, from problem framing through launch and iteration.
Serve as the primary design voice on your team.
Prototype and test ideas quickly using Claude Code, Cursor, or your AI tool of choice, with AI generating the initial pixels and prototype.
Define patterns, behaviors, and the quality bar for the product.
Partner closely with product managers, engineers, and researchers to shape product direction, scope, and priority.
Design for critical moments in a patient's journey: finding a provider, understanding benefits, booking appointments, and maintaining engagement in care.
Run experiments with clear success metrics, measuring conversion, retention, and task completion, and treating negative results as valuable findings.
Contribute to Helix, our design system, and share AI prompts and patterns with the broader design team.
At the Staff level, lead both 0→1 and at-scale work, launching new patient features and significantly improving existing ones.
Design AI-native patient experiences, including conversational flows, intelligent matching, and agentic care navigation to replace manual processes.
Set the standard for AI-native practice within the design team, prototyping in code and staying involved through launch.
Mentor other designers, elevate the craft standard, and influence the design organization's practices through critique, design system contributions, and shared knowledge.
Influence product direction using design rationale, research, and storytelling, with a role in shaping the patient roadmap.