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 You're comfortable with high autonomy and can tackle any technical challenge with minimal guidance You care about our mission of building a mental healthcare system that everyone can access

Compensation & Benefits:

The expected base pay range for this position is $215,900 - $254,000 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

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