Engineering Manager, Benefits

About the Team & Role

Mental health care shouldn't come with surprise bills. It shouldn't cost patients hours on the phone to find out what their insurance actually covers, and it shouldn't cost providers sleep wondering whether they'll get paid for the work they did. At Headway, getting insurance right — reliably, accurately, and in real time — is one of the most important problems we solve. And it sits at the heart of a multi-billion-dollar mental health system we're building from the ground up.

We're hiring an Engineering Manager to lead the team that owns Headway's benefits platform: the core systems that determine what every patient's insurance actually covers, what they'll pay out of pocket, and how providers get reimbursed accurately. This is infrastructure that the rest of the company runs on. When it works, millions of appointments happen smoothly; when it doesn't, patients don't get care and providers don't get paid.

You'll lead a team of 4–5 engineers, co-own the roadmap with your PM, and report to our Senior Engineering Manager, who will give you the autonomy to run this team end-to-end while being a close thought partner. This is a role designed for a leader who still wants to be in the weeds — reading PRs, shaping tech specs, showing up to design reviews as a contributor. At Headway, technical credibility is how engineering managers lead.

What You'll Own

• A team of 4–5 engineers — hiring, growing, and coaching them through the most formative stretch of their careers
• A platform that sits at the core of Headway's business — every patient booking, every provider payout, and every claim depends on what your team builds
• The roadmap, in partnership with product — setting the pace, the priorities, and the bets for one of the most leveraged engineering teams at the company
• The technical standards and team culture — how the team scopes work, how it makes architectural decisions, how it responds to incidents, and how it treats on-call as a first-class concern
• A seat at the table — partnering with the leaders of claims, eligibility, billing, and payer partnerships to keep the whole system honest

You'd Be a Great Fit If...

• You built your career as an engineer first. You've spent 5+ years writing and shipping code at a senior or staff level, and you're still close enough to the craft to push back in a design review.
• You're early in your management career — maybe you're already running a small team, or maybe you've been a tech lead with a few reports and you're ready for a bigger scope. We're betting on trajectory, not tenure.
• You've built robust systems and love thinking through all the moving pieces of a complex system. You've owned things other teams depend on, and you take that responsibility seriously.
• You understand deep problems and build intelligent systems with the right leverage — whether that's agents, predictive algorithms, or the rules and infrastructure that hold it all together. You see AI as a tool for solving real business problems, not as a hammer looking for a nail.
• You're energized by mission-driven work. You want your engineering career to matter beyond the code — and you see how better infrastructure for mental health care is better access to mental health care.
• You give direct, kind feedback. You've told someone a hard truth about their work and left the relationship stronger for it.

Bonus points for:

• Deeper machine learning fluency — hands-on experience with eval loops, model rollout, or production ML systems
• Healthcare, insurance, or claims experience
• Scaleup experience, Series B through D

Compensation and Benefits:

The expected base pay range for this position is $190,000 - $237,500, 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