[All remote jobs](https://jobicy.com/jobs.md)[![Headway.co logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/068391a61855fb604bca051cafe3c510.jpeg)](https://jobicy.com/company/headway.md)[Headway.co](https://jobicy.com/company/headway.md) # Product Manager Review the role, location requirements, compensation details, and application process before deciding whether this opportunity fits your next career move. [Apply for this job](#job-application)[View company](https://jobicy.com/company/headway.md)ShareRemote from[USA](https://jobicy.com/job-region/usa.md)SalaryUSD 262,200–375,500 / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceSeniorPublished31 Oct 2026Apply before30 Nov 2026Listing views30Application actions0Application toolkit ## Make your next move. Prepare your resume, explore your fit, and draft a cover letter for this opportunity. AI Summary ## The role, at a glance. Headway is hiring senior-to-principal Product Managers to own high-impact product areas across patient, provider, payer, and platform experiences. The role requires end-to-end product strategy, outcome ownership, and close collaboration with engineering, design, data science, clinical, legal, finance, and operations partners. A central responsibility is identifying and shipping reliable AI and LLM-enabled capabilities in a regulated mental-health and insurance environment. Candidates need deep product leadership experience, strong quantitative judgment, and the ability to communicate clearly with senior stakeholders. The role is remote in the United States and offers an explicitly stated annual base-compensation range. ## Role DNA A quick view of the complexity, pace, ownership and collaboration implied by the job description. ### Job Complexity 5/5EasyHard ### Pace & Pressure 5/5RelaxedFast-paced ### Autonomy Level 5/5GuidedFull ownership ### Communication Load 5/5IndependentCollaborative AI insightThis is a highly senior product role spanning complex healthcare, insurance, marketplace, and AI systems, where decisions carry material compliance and business consequences. Success requires independently setting strategy while influencing numerous technical and non-technical stakeholders. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$318,850US market range (per year)$240k–$380k0$418.00k AI insightHeadway explicitly lists annual compensation of $262,200–$375,500 USD, with a midpoint of $318,850. Estimated US annual market compensation for a senior/principal product leader with AI, platform, and regulated-healthcare scope is approximately $240,000–$380,000 USD; this is an AI estimate rather than verified salary research. ## Core skills Skills and capabilities most closely associated with this opportunity. [Product strategy](https://jobicy.com/jobs?search_keywords=Product%20strategy.md)[Product roadmap](https://jobicy.com/jobs?search_keywords=Product%20roadmap.md)[AI product management](https://jobicy.com/jobs?search_keywords=AI%20product%20management.md)[LLM systems](https://jobicy.com/jobs?search_keywords=LLM%20systems.md)[Prompt engineering](https://jobicy.com/jobs?search_keywords=Prompt%20engineering.md)[Retrieval-augmented generation](https://jobicy.com/jobs?search_keywords=Retrieval-augmented%20generation.md)[Product analytics](https://jobicy.com/jobs?search_keywords=Product%20analytics.md)[Experiment design](https://jobicy.com/jobs?search_keywords=Experiment%20design.md)[Causal analysis](https://jobicy.com/jobs?search_keywords=Causal%20analysis.md)[Marketplace platforms](https://jobicy.com/jobs?search_keywords=Marketplace%20platforms.md)[Healthcare technology](https://jobicy.com/jobs?search_keywords=Healthcare%20technology.md)[Insurance workflows](https://jobicy.com/jobs?search_keywords=Insurance%20workflows.md)[Cross-functional leadership](https://jobicy.com/jobs?search_keywords=Cross-functional%20leadership.md)[Stakeholder management](https://jobicy.com/jobs?search_keywords=Stakeholder%20management.md)[Regulatory compliance](https://jobicy.com/jobs?search_keywords=Regulatory%20compliance.md) Sample interview questionsDescribe an AI-powered product you shipped from concept to production. How did you validate that it delivered durable value rather than a compelling demo?I would explain the user problem, baseline metrics, model and workflow design, and staged rollout plan. I would highlight offline evaluation, guardrails, human-review paths where appropriate, controlled experiments, and production metrics such as adoption, task success, quality, latency, and error rates. How would you decide whether an LLM capability should be used for a provider administrative workflow? I would begin with workflow research to identify high-volume, repetitive, and error-prone tasks. I would assess expected value, risk, data availability, evaluation criteria, privacy and compliance constraints, and fallback mechanisms before prioritizing a limited pilot with measurable outcomes. Tell us about a time you aligned stakeholders with competing incentives around a difficult product decision. I would frame the conflicting objectives, make assumptions and trade-offs explicit, and use customer evidence and quantitative analysis to guide the decision. I would establish shared success metrics, document the decision rationale, and maintain a feedback loop to revisit the plan if evidence changed. How would you measure whether an AI-powered patient-provider matching experience is successful? I would measure successful match completion, appointment booking, time to first appointment, patient retention, clinical appropriateness signals, provider acceptance, and downstream care outcomes. I would also monitor fairness, safety, complaint rates, and differences in outcomes across patient cohorts. What product risks are most important when building AI features in a regulated healthcare setting? Key risks include privacy and security, incorrect or unsafe recommendations, bias, inadequate explainability, unreliable model behavior, and weak auditability. I would partner early with clinical, legal, security, and engineering teams to define guardrails, evaluations, escalation processes, and monitoring requirements. Opportunity details ## About this role. 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 The Role We’re looking for Product Managers across Senior, Staff, Principal, and Senior Principal levels who are curious builders, eager to drive company level impact and to build in an environment where AI is a core part of the toolkit. We are hiring across Patient, Provider, Payer, and Platform. The right candidates will bring strong product fundamentals and a willingness to build with AI in a regulated, high-stakes industry. Product Managers at Headway own product areas end-to-end: setting strategy, partnering deeply with engineering, data science, and design, and driving outcomes that move the company. The way we are building is continuously evolving, and the size of opportunity for Headway to leverage AI is massive. We sit at the intersection of healthcare delivery, complex insurance systems, and a multi-sided marketplace serving tens of thousands of providers and millions of patients. ### The Problems We’re Solving For Patients * Finding the right therapist, understanding your insurance benefits, and staying in care shouldn’t be hard. Today it is. We’re building AI-powered matching and personalized care navigation that help patients get into — and stay in — mental health care at scale. One million patients a month ask for a referral to a mental health provider. We’re building the systems that ensure they actually get there. For Providers * Therapists spend a staggering amount of time on administrative tasks — credentialing, documentation, scheduling, billing — instead of with their patients. We’re using AI to automate clinical workflows, simplify complex insurance requirements, and give providers more time to do what they came here to do. The goal: a thriving practice on Headway that practically runs itself. For Payers * Health insurers are asking harder questions: Is care on Headway actually working? Is it worth what we’re paying? We’re using AI to answer them at scale — measuring clinical outcomes, building dashboards that demonstrate responsible care, and moving toward a model where patients are matched to the right care pathways and providers are aligned around better outcomes. This work protects Headway’s standing with insurers and opens doors to deeper, more strategic partnerships. For Platform * The infrastructure underneath Headway — billing, claims, payments, and trust and safety — needs to scale reliably at the speed of our growth. We’re using AI to automate complex, high-volume workflows, detect fraud and errors faster, and build systems that get smarter over time. This is foundational infrastructure with direct impact on Headway’s economics and compliance posture. ### What You’ll Do at Headway * Define and own the product strategy for your area in partnership with engineering, design, data, clinical, and operations teams * Apply AI where it matters: identify where intelligence creates step-change improvements in your product area and drive those bets from insight through production * Set and own clear success metrics; communicate results and course-correct with urgency * Represent the voice of your customer — patient, provider, or health plan — with conviction in every decision, grounded in data and direct research ### You’d Be a Great Fit If… * You have 8+ years of product management experience with a track record of owning complex, high-impact product areas * You have experience with LLM systems — prompting, retrieval, evaluation, fine-tuning — and a track record of shipping AI-powered products that hold up at scale, not demos. * You’ve built at scale in a marketplace, platform, or data-intensive environment — and can show the outcomes you drove * You’re energized by working in regulated, complex industries and see constraints as a product design challenge rather than a blocker * You can influence across engineering, clinical, legal, finance, and operations — and you’re equally comfortable in the data and in the room * You have strong quantitative fluency and can partner with data scientists on experiment design and causal analysis * You communicate with precision — in writing, in product reviews, and with senior leadership #LI-EM1 ### 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. Headway participates in E-Verify. To learn more, click [here.](https://www.e-verify.gov/sites/default/files/everify/posters/EVerifyParticipationPoster.pdf) 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](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](http://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. Show more [Apply now >](https://jobicy.com/jobs/158212-product-manager-10.md) * ![Upload CV](data:image/svg+xml;base64,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) ### Upload your resume now To unlock remote work opportunities and be discovered by global employers. This job listing has been manually reviewed by the Jobicy Trust & Safety Team for compliance with our posting guidelines, including verification of the company's legitimacy, accuracy of job details, clarity of remote work policy, and absence of misleading or fraudulent content. Next step ## Apply now. Follow the employer’s application method and review Jobicy’s safety guidance before sharing personal information. Keep exploring ## Related remote jobs. * ![LaunchDarkly logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/115b7a27-221.jpg) LaunchDarkly Oct 31 New ### [Director, Internal AI Operations](https://jobicy.com/jobs/158213-director-internal-ai-operations.md) About the Job: LaunchDarkly is looking for a strategic, execution-oriented Director of Internal AI Operations to run and continuously improve how our company adopts and scales AI, establish the operational… * ![CrossFit logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/6966c9ea04a0e651f69f113113a45e27.png) CrossFit Oct 31 New ### [Senior Product Manager, Education](https://jobicy.com/jobs/158186-senior-product-manager-education.md) CrossFit is seeking a Senior Product Manager, Education. You will own product strategy and execution for CrossFit’s Education line of business, including the learner experience, course registration, content authoring and… * ![CrossFit logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2021/12/6966c9ea04a0e651f69f113113a45e27.png) CrossFit Oct 31 New ### [Director of Affiliates](https://jobicy.com/jobs/158172-director-of-affiliates.md) CrossFit is seeking a Director of Affiliates—a proven business leader and experienced affiliate owner to lead our affiliate business and ensure HQ effectively serves and empowers the global CrossFit affiliate… * ![Twilio logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2020/10/WRILS-201023175858-722503.jpg) Twilio Oct 31 New ### [Americas Sales Business Partner Manager](https://jobicy.com/jobs/158143-americas-sales-business-partner-manager.md) Who we are At Twilio, we’re shaping the future of communications, all from the comfort of our homes. We deliver innovative solutions to hundreds of thousands of businesses and empower… * ![Vercel logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/a6aded72-221.png) Vercel Oct 31 New ### [Product Manager, Dashboard](https://jobicy.com/jobs/154269-product-manager-dashboard.md) About Vercel: Vercel is the agentic infrastructure company, freeing people and agents to ship what’s next. For more than a decade we’ve helped builders move from idea to production with… * ![saas.group logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/f6d362c3-221-1.png) saas.group Oct 31 New ### [Chief Executive Officer](https://jobicy.com/jobs/154289-chief-executive-officer-3.md) What is saas.group? The role is for a future CEO position at saas.group, tied to an upcoming acquisition in the HR tech and workforce management space. We are continuously acquiring… * ![Liftoff logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/c47aea9f-221.png) Liftoff Oct 31 New ### [Senior Staff Product Manager, eCommerce](https://jobicy.com/jobs/154258-senior-staff-product-manager-ecommerce.md) Liftoff is a leading AI-powered performance marketing platform for the mobile app economy. Our end-to-end technology stack helps app marketers acquire and retain high-value users, while enabling publishers to maximize… * ![Amplitude logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/bda3af21-221.jpg) Amplitude Oct 30 New ### [Deal Desk Manager](https://jobicy.com/jobs/158131-deal-desk-manager-2.md) Amplitude is the leading AI analytics platform, helping over 5,200 customers—including Atlassian, Burger King, NBCUniversal, and Square—build better products and digital experiences. With powerful AI Agents embedded across our platform,… * ![NVE Experience Agency logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/ddc1676e-221.png) NVE Experience Agency Oct 30 New ### [Growth Operations Manager](https://jobicy.com/jobs/158107-growth-operations-manager.md) NVE is a brand experience and production agency dedicated to building ideas rooted in culture and guided by the principle that ‘The Right Moment Will Transform Someone Forever.’ NVE’s team… * ![Airtm logo](https://jobicy.com/data/server-nyc0409/galaxy/mercury/2025/06/1994f28e-221.png) Airtm Oct 30 New ### [COO](https://jobicy.com/jobs/158101-coo.md) About Airtm Airtm is building the global stablecoin wallet for digital entrepreneurs, the place where people receive earnings, hold balances, convert value, and cash out across 40+ markets. Our mission:… [Browse all jobs](https://jobicy.com/jobs.md)