Senior Engineering Manager, Payer & Outcomes

Headway's mission is to build a new mental healthcare system that everyone can access, one that works for patients, providers, and payers alike. Our Payer & Outcomes group is where we prove that model works. We build the systems that answer two questions insurers have never been able to answer well: did the care actually work, and was it worth it?

As Senior Engineering Manager for Payer & Outcomes, you'll lead the two teams that answer them. Outcomes builds our measurement backbone: collecting patient-reported outcomes at scale, tracking symptom improvement and retention to care, and turning that into evidence we can stand behind. Network Value builds the intelligence behind utilization and cost of care, covering patient acuity and segmentation, provider efficiency ranking, and the sub-network logic that routes a patient to the right level of care.

These two teams share data foundations, a measurement stack, and an audience, which is why they sit together under one leader. You'll own delivery on a company-level goal we have publicly committed to: significantly increasing the share of new patients with a baseline outcome measure, without increasing provider churn. That means holding quality and adoption in tension rather than trading one for the other.

You'll grow and mentor a team of roughly eight engineers plus an engineering manager, set the technical and operational roadmap across both pods, and partner daily with Product, Clinical, Data Science, and our payer-facing commercial teams. This is a deeply cross-functional role: your work is what lets Headway move payers from administrative oversight to genuine care partnership.

The stakes here are concrete. Elsewhere in the group we now review clinical notes and prompt providers to put a safety plan in place when a patient shows signs of suicidal risk. At full adoption across our network, that single intervention is estimated to prevent more than 1,000 deaths a year. Your teams build the measurement and targeting layer that decides where interventions like that get aimed, and whether we can prove they worked.

Who you are

We're looking for an experienced engineering leader who is product-minded, data-informed, and energized by growth. You'll work closely with Engineering Leadership, Product, and Data to shape the future of Headway's payer strategy. There is an unusually direct line from your team's work to whether this model of care survives contact with the market.

In this role you will

• Lead, manage, and grow two engineering teams
• Own delivery on a company-level outcomes key result, including its guardrails
• Set the technical and operational roadmap across measurement, segmentation, and utilization
• Develop your team through weekly 1:1s, mentorship, and direct feedback, and develop the manager reporting to you
• Partner closely with Product, Clinical, Data Science, and Commercial to iterate quickly and rigorously
• Contribute to the broader group and company strategy, not just your own roadmap

Experience we're seeking

• 6+ years of engineering management experience at a high-growth startup or scale-up, including managing managers or tech leads
• 3-5+ years of experience as a software engineer, enough to hold technical direction credibly
• A track record of building and leading high-performing teams that delivered business outcomes through technical investment
• A strong product mindset and cross-functional relationships that build trust with users and stakeholders
• Experience owning an externally-committed metric, with the scope discipline that requires
• Comfort with data- and ML-heavy systems: measurement, experimentation, and metric guardrails
• Nice to have: healthcare, insurance, or another regulated, high-trust domain
• Nice to have: value-based care, quality measurement, or utilization management
• Nice to have: prior experience with Python, React, and AWS infrastructure

You'll love this role if you want to

• Lead the teams that decide whether a new model of mental healthcare can be proven, not just described
• Own a number the company reports externally, with the autonomy that comes with it
• Build an engineering management layer beneath you rather than inherit a finished org

Our interview process

After you apply to Headway, here are some details of what to expect during the interview process.

• Initial screen: You'll connect with someone in recruiting so you can learn more about the team, Headway's mission and exciting growth, and we can get a better idea of your background.
• First rounds: You'll meet with an engineering leader on the team to go deeper into your team and people leadership experience. You'll also complete an AI Coding round - a collaborative session where we're less focused on syntax and more on how you think through problems and work with AI tools in a technical context.
• Final rounds: You'll meet team members across product and engineering leadership for multiple behavioral interviews and one more technical interview (System Design), leaving you with a fuller picture of what it's like to work at Headway.
• References and the Offer: Our favorite part of the process! We'll send over all of the details, including specifics on employee equity, and congratulatory messages from excited future team members!

Compensation and Benefits:

The expected base pay range for this position is $265,200 - 331,500, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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