Senior Technical Program Manager

Summary

Join Headway's Engineering team as a Senior Technical Program Manager specializing in Security. This pivotal role involves defining and executing critical security initiatives, acting as a strategic partner with the Trust team to translate complex challenges into effective execution plans. You will lead end-to-end technical programs, prioritize technical investments, spearhead operational health initiatives, and establish key metrics. The position requires cross-functional collaboration with engineering, product, and business teams. You will communicate program status to senior leadership and create scalable processes to improve engineering efficiency. This is a unique opportunity to shape the role and contribute to Headway's mission of improving mental healthcare access.

Requirements

• 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

Responsibilities

• 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

Benefits

• 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