Headway.co

Staff Product Manager, Enterprise Products

USA, United States full-time Mid Salary not listed
full-time Mid level Technology & IT Curated
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About the 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.

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.

Interview prep

Walk in with sharper answers.

Use this as a quick practice sheet before you speak with the employer.

Mid
Technology & IT Human Resources Sales Staff Product Manager Mid level

Likely questions

  1. Tell us about work you have done that is close to the Staff Product Manager, Enterprise Products role.
  2. How would you approach your first 30 days at Headway.co?
  3. Which of Human Resources, Sales and Staff have you used recently, and what did it help you achieve?
  4. Describe a time you solved a problem without waiting to be told exactly what to do.
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Human Resources, Sales and Staff.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Staff Product Manager, Enterprise Products role because I can bring practical experience in Human Resources, Sales and Staff, learn the team quickly, and contribute to the outcomes Headway.co needs from this hire.

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