Staff Technical Program Manager
About the role
Headway is a Series D company dedicated to making mental healthcare more accessible and affordable. Our mission is to solve the biggest barriers to care, starting with insurance. We automate administrative tasks and are building the platform where care actually happens.
Responsibilities
- Lead critical, high-impact technical programs across the Insurance platform, including driving key technical initiatives, optimizing systems and processes, and financial remediation initiatives.
- Own outcomes from discovery through delivery, 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.
- Pursue data rearchitecture initiatives, delivering a modernization of our data systems, observability, and accelerating 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, enhance insurance operations reliability, and boost 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.
Qualifications
- Proven experience driving complex, high-impact programs that span engineering, operations, finance, and compliance.
- Experience structuring messy problems, establishing clarity, and driving systematic improvements.
- Energetic passion for transforming operational chaos into efficient, repeatable processes.
- Natural collaboration skills, building trust across diverse stakeholders and influencing without authority.
- Strategic thought partnership ability to work alongside strong Engineering and Operations leaders, balancing technical excellence with business pragmatism.
- Executive presence and capability to communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI.
- Experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year.
- Comfort with high autonomy and ability to tackle technical and operational challenges across the stack with minimal guidance.
Benefits
- Compensation: 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.
- Benefits: 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.
Company Culture
We are 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.
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.