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 75,000 providers across all 50 states run their practice on our software, serving over 1 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. 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 TPM at Headway:

Join Headway's Engineering team as a Staff Technical Program Manager—a pivotal role where you'll define how we execute our most critical technical initiatives. You'll be the strategic thought partner who transforms complex, cross-functional challenges into clear execution plans that deliver topline business impact on our most critical company OKRs.

Primarily partnering with our Insurance team, you'll lead key programs that touch nearly every aspect of our insurance systems, platform, and patient & provider product areas. This isn't about project coordination—you're an end-to-end leader of complex technical and critical product-dependent initiatives that are essential to our business success. As the sole TPM for the Insurance platform, you'll have the unique opportunity to establish the TPM function in this space while partnering with engineering leadership to drive our most important technical priorities.

In making mental health more accessible and affordable, we pride ourselves in tackling the largest, most critical problems and opportunities at the company. The TPM brand is a strategic thought partner who simplifies complexity, drives craft and velocity into execution, and raises the bar on operational excellence that scales.

Responsibilities:

Lead critical, high-impact technical programs across Insurance platform including driving key technical initiatives, optimization of systems and processes, and financial remediation initiatives—owning outcomes from discovery through delivery
Drive end-to-end cross-team programs by coordinating cross-functional planning and execution to reduce operational costs and manual workflow inefficiencies
Establish repeatable playbooks, tooling, and systematic improvements for cyclical operational challenges, transforming how we work into predictable, efficient processes
Lead key data rearchitecture initiatives, delivering on a modernization of our data systems, observability, and accelerate decision-making velocity across R&D
Spearhead financial remediation programs across R&D, driving year-over-year improvements
Be a strategic thought partner with Insurance team leadership to balance competing priorities, manage technical dependencies, and align on investment roadmaps
Create scalable frameworks and operating mechanisms that improve operational efficiency, improve insurance operations reliability, and enhance team productivity
Navigate complex stakeholder landscapes across engineering, product, operations, finance, and compliance teams to drive alignment on technical strategy and execution
Communicate program status, risks, and strategic decisions to senior leadership, translating technical complexity into business impact and ROI

You’ll love this role if:

You've driven complex, high-impact programs that span engineering, operations, finance, and compliance—with proven experience owning outcomes end-to-end
You thrive in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and drive systematic improvements
You're energized by transforming operational chaos into efficient, repeatable processes—turning annual scrambles into smooth, predictable cadences
You're a natural collaborator who builds trust across diverse stakeholders and can influence without authority to get things done
You're a strategic thought partner who can work alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism
You have executive presence and can communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI
You're passionate about operational efficiency and have experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year
You're a force multiplier who removes blockers, accelerates decision-making, and enables teams to focus on high-value work
You're comfortable with high autonomy and can tackle technical and operational challenges across the stack with minimal guidance
You care about our mission of building a mental healthcare system that everyone can access

Compensation and Benefits:

The expected base pay range for this position is $190,400 - $238,000 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

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.