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 RoleYou will be the first dedicated AI Product Manager on the Patient side at Headway. Your mission: build AI-powered products that help patients find the right therapist, stay engaged in care, and achieve measurable improvements in their mental health. This is not an AI-strategy-deck role. You will ship. You will write evals. You will debug prompt chains. You will partner with ML engineers and data scientists to build products that work for real patients in a HIPAA-compliant environment. We power over 500,000 appointments per month. Now we are building AI-powered experiences to help patients find the right care and stay in it! What you’ll do at Headway: - Own AI-powered patient intake and therapist matching: design LLM-driven flows that understand patient needs and recommend the right provider. - Build between-session AI support experiences: personalized tools that help patients reflect, prepare, and build therapeutic habits. - Establish evaluation and safety infrastructure: write evals, build test suites, design red-teaming protocols, and implement human-in-the-loop escalation. - Advance outcome measurement: move beyond PHQ-9/GAD-7 to AI-informed measurement. - Partner with Engineering, ML, Data Science, Clinical, and Legal to ship AI products in a HIPAA-compliant architecture. You’ll be great for this role if you: - 8+ years of PM experience, with at least 2 years shipping AI/ML-powered products to real customers. - You have personally written evals for AI product quality. - You have built multi-step LLM-powered user flows in production. - Strong technical fluency with LLMs: model selection, RAG architectures, fine-tuning, cost/latency/quality. - You are a builder who has shipped AI products in partnership with ML engineers. - Bonus: Experience in regulated industries (healthcare, fintech, insurance). - Bonus: Experience in healthcare or mental health. - You understand that building AI for people managing their mental health requires a different level of care and safety. 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 #LI-EM1 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.

• Play a crucial role in shaping and driving the development of our Financials solutions • Maximize the value of our product by effectively managing the product backlog and collaborating with cross-functional teams • Support by providing insights or feedback collected from ongoing interactions with stakeholders and customers • Provide tactical insights and historical data from previous projects or current product usage • Represent customer needs, priorities and constraints in every decision • Manage detailed requirements and user stories • Collaborate with UX and engineering to develop prototypes • Gather feedback from prototype testing • Work closely with Engineering to ensure features are developed as per requirements • Engage with Support and manage maintenance backlog for the squad and teams • Support quality assurance from functional perspective • Define acceptance criteria for each deliverable and sign off completed work on behalf of the customer • Monitor post-release performance metrics and gather feedback.

• play a crucial role in shaping and driving the development of our Financials solutions • responsible for maximizing the value of our product by effectively managing the product backlog and collaborating with cross-functional teams • provide tactical insights and historical data from previous projects or current product usage • assist in refining high-level requirements by sharing practical constraints or opportunities identified during day-to-day operations • represent customer needs, priorities and constraints in every decision • own all aspects of the delivery, including scope, pricing context and customer facing trade-offs • manage detailed requirements and user stories • collaborate with UX and engineering to develop prototypes • gather feedback from prototype testing • ensure backlog reflects the evolving requirements as a result of refinement and solutioning • manage sprint planning and team-level backlog refinement • work closely with Engineering to ensure features are developed as per requirements • track progress and address any blockers • engage with Support and manage maintenance backlog for the squad and teams • support quality assurance from functional perspective • define acceptance criteria for each deliverable and sign off completed work on behalf of the customer • monitor post-release performance metrics and gather feedback. • partner with the Product Lead to balance commercial urgency against technical quality and sustainability

• Shape and drive the development of Financials solutions • Maximize the value of the product by managing the product backlog • Collaborate with cross-functional teams • Provide tactical insights and historical data from previous projects • Represent customer needs, priorities, and constraints in decisions • Manage detailed requirements and user stories • Collaborate with UX and engineering to develop prototypes • Manage sprint planning and team-level backlog refinement • Ensure features are developed as per requirements • Monitor post-release performance metrics and gather feedback