Staff Technical Program Manager

Headway’s mission is a big one – to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance. 

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice. 

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 60,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

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 our first 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 top line business impact on our most critical company OKRs.

Primarily partnering with our Foundations team, you'll tackle the engineering programs that touch every aspect of our systems and processes. This isn't about project coordination—you're an end-to-end leader of complex technical initiatives that are essential to our business success. As the foundational TPM hire, you'll have the unique opportunity to establish the TPM function 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.

What you'll do at Headway:

• Lead end-to-end technical programs that span across engineering and the company, owning outcomes from definition through delivery
• Enumerate and prioritize technical investments across our engineering organization, creating comprehensive programs to systematically address key technical challenges to help us scale 10x-100x
• Spearhead Operational Health initiatives to improve system observability, reliability, performance, and operational excellence
• Be a strategic thought partner with the Foundations team leadership to align on priorities and drive execution on key investments
• Establish operational health metrics and drive continuous improvement programs that enhance developer experience
• Leadership in cross-functional alignment between engineering, product, and business teams on technical strategy, roadmap, and prioritization
• Create scalable processes and playbooks that improve engineering velocity, predictability, and quality
• Communicate with senior leadership on program status, risks, and strategic technical decisions

You'll be great for this role if you:

• You've driven large-scale programs across diverse, cross-functional teams and have proven experience with end-to-end program ownership
• You thrive in ambiguous environments and can structure complex problems while navigating competing priorities
• You're a natural collaborator who builds trust across teams and can influence without authority
• You’re a strategic thought leader who can partner and contribute alongside strong Engineering leaders towards realizing a technical vision
• You have executive presence and can communicate effectively with senior leadership while escalating and resolving conflicts
• You're passionate about operational excellence and have experience implementing best practices, tooling, and processes that scale
• You're energized by being a force multiplier who enables teams to move faster and deliver higher quality outcomes
• You want to build something from the ground up and define how technical program management works at a quickly growing company
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