[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) # Staff Product Manager, Enterprise Products 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 265,200–331,500 / yrDepartment[Product & Operations](https://jobicy.com/categories/management.md)EmploymentFull TimeExperienceSeniorPublished28 Oct 2026Apply before27 Nov 2026Listing views44Application actions1Application 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 seeking a Staff Product Manager to build enterprise-grade products for major payer accounts within its mental healthcare platform. The role translates commercial and payer business-development needs into scalable product requirements in close partnership with Engineering and Data. This leader will establish a repeatable enterprise-product framework that avoids bespoke, single-account solutions while supporting contracting, renewals, and expansions. Success requires experience with enterprise sales motions, procurement and legal stakeholders, cross-functional influence, and a startup-oriented delivery pace. ## 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 staff-level, build-from-scratch product role balancing complex payer enterprise requirements with rapid internal execution. The PM must influence Engineering, Data, and BD teams without direct roadmap authority while creating reusable product strategy. ## Salary analysis Estimated compensation compared with the broader US market for similar roles. Estimated job median (per year)Highly competitive$298,350US market range (per year)$230k–$340k0$374.00k AI insightThe employer discloses a yearly base compensation range of $265,200–$331,500 USD, with a midpoint of $298,350. The estimated US market range for a staff-level enterprise product manager is $230,000–$340,000 USD per year; estimates are not 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)[Enterprise product management](https://jobicy.com/jobs?search_keywords=Enterprise%20product%20management.md)[Enterprise sales](https://jobicy.com/jobs?search_keywords=Enterprise%20sales.md)[Payer partnerships](https://jobicy.com/jobs?search_keywords=Payer%20partnerships.md)[Healthcare technology](https://jobicy.com/jobs?search_keywords=Healthcare%20technology.md)[Requirements gathering](https://jobicy.com/jobs?search_keywords=Requirements%20gathering.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)[Product discovery](https://jobicy.com/jobs?search_keywords=Product%20discovery.md)[Roadmap prioritization](https://jobicy.com/jobs?search_keywords=Roadmap%20prioritization.md)[Data collaboration](https://jobicy.com/jobs?search_keywords=Data%20collaboration.md)[Procurement navigation](https://jobicy.com/jobs?search_keywords=Procurement%20navigation.md)[Contracting support](https://jobicy.com/jobs?search_keywords=Contracting%20support.md)[Scalable platform design](https://jobicy.com/jobs?search_keywords=Scalable%20platform%20design.md)[Strategic account management](https://jobicy.com/jobs?search_keywords=Strategic%20account%20management.md) Sample interview questionsHow would you evaluate a strategic payer request to determine whether it should become a reusable product capability?I would identify the underlying workflow and business outcome, validate whether similar needs exist across the payer segment, and assess revenue, retention, operational, and technical impact. I would then frame a modular solution with clear adoption criteria rather than committing to an account-specific implementation. Describe how you would partner with a business-development team during an enterprise deal without allowing every prospect request to dictate the roadmap. I would establish a structured intake and evaluation process that makes commercial context visible, including deal stage, customer impact, urgency, and strategic value. I would communicate trade-offs clearly and offer alternatives such as configuration, phased delivery, or a reusable product direction when a bespoke request is not justified. How do you maintain startup velocity while navigating procurement, legal, and multi-stakeholder approval processes? I separate external decision timelines from internal execution planning, clarify dependencies early, and use incremental releases to validate value quickly. This allows the team to make progress on high-confidence work without waiting for every enterprise approval to conclude. What metrics would you use to assess the success of enterprise payer products? I would combine commercial measures such as contract win rate, renewal and expansion influence, and time to close with product measures such as adoption, workflow completion, reliability, and support burden. I would also track reuse across accounts to ensure the portfolio is becoming more scalable rather than increasingly bespoke. Tell us about a time you influenced technical and commercial stakeholders without direct authority. I aligned stakeholders around a shared customer problem, supported the proposal with qualitative and quantitative evidence, and made trade-offs explicit. By creating a decision framework and maintaining regular communication, I helped the group prioritize a solution that met customer needs while fitting the broader product strategy. 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 Payer & Patient Outcomes at Headway Headway’s relationship with payers is evolving from a credentialing and billing partnership to something far more valuable: a network that can prove what it delivers and build products purpose-built for how health plans actually operate. The Payer & Patient Outcomes team owns that transformation — building the products, data infrastructure, and measurement frameworks that let Headway walk into a payer conversation with more than access to sell. About this role As Enterprise Product Manager, Payer, you’ll own the product layer that turns Headway’s relationships with its largest payer accounts into differentiated, enterprise-grade product — not one-off features built to placate a single account, but capabilities that create real leverage in contracting and open new ways for payers to engage with Headway. You’ll work in lockstep with our Payer BD/Commercial team, translating what actually moves a deal into product requirements, and with Data and Engineering to ship it. This is a build-from-scratch mandate: there’s no existing enterprise-product playbook here, and part of the job is creating one. What You’ll Own * Enterprise-tier products built in direct partnership with named strategic payer accounts — the kind of capability that’s a genuine reason a payer signs, renews, or expands with Headway * The product-side relationship with Payer BD: translating commercial asks into requirements, and pushing back or reshaping them when a better path exists * A repeatable framework for enterprise payer product work, so builds for one payer become reusable rather than bespoke * Navigating enterprise buying process (procurement, legal, multi-stakeholder sign-off) without importing enterprise pace into how the team builds internally You’d be a great fit if… * You’ve operated as a Staff-level PM inside a real enterprise sales motion — you understand what makes a large, slow-moving institutional buyer actually move, and you’re comfortable being evaluated by procurement and legal, not just end users * You can hold enterprise rigor and startup urgency at the same time — you don’t use “enterprise” as an excuse to slow down * You can generalize a single account’s specific ask into something reusable, rather than shipping a one-off every time * You’ve built trust and gotten cross-functional partners (Engineering, Data, BD) to prioritize your work without having authority over their roadmaps * Healthcare/payer experience is a plus, not a requirement — what matters more is that you’ve already proven this pace-vs.-rigor tension somewhere else 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. 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