About TPM at Headway 

Join Headway's Engineering team as a Senior Technical Program Manager and first TPM to focus on Security — a pivotal role where you'll define how we execute our most critical security initiatives. You'll be a strategic thought partner with the Trust team to transforms complex, cross-functional challenges into clear execution plans that deliver topline business impact.

Primarily partnering with our Trust team, you'll tackle broad security programs that touch every aspect of our systems and teams. This isn't about project coordination—you're an end-to-end leader of complex security initiatives that are essential to our business short and long term success. As the first TPM to focus on Security, you'll have the unique opportunity to define this role 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 in Security 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 and security challenges to help us safely scale 10x-100x
• Spearhead Operational Health initiatives to improve system observability, reliability, performance, and operational excellence
• Be a strategic thought partner with the Trust team leadership to align on priorities and drive execution on key investments
• Establish operational health metrics and drive continuous improvement programs that enhance our security posture
• 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 security 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 and cross-functional 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

Our Interview Process

• Pre-onsite: Recruiter screen
• On-site 1: Hiring manager
• On-site 2: A full loop with senior members across the team
  • TPM Competency
  • Peer Leadership
  • Driver of Results
  • Architecture (system design)

Compensation & Benefits:

The expected base pay range for this position is $183,600 - $216,000, 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