Staff Technical Program Manager

About the role

You will own the end-to-end execution of critical technical and business initiatives that define how Headway delivers on its mission of transforming mental healthcare access. You will serve as the strategic thought partner for the Insurance platform, owning the narrative and execution of complex programs from initial discovery through scaled delivery. You will lead high-impact initiatives that optimize systems, reduce operational friction, and drive financial remediation across the entire insurance ecosystem. You will establish the foundational playbooks and repeatable frameworks that turn chaotic operational challenges into predictable, scalable processes. You will navigate intricate stakeholder environments to align engineering, product, operations, finance, and compliance on a shared technical and business vision. You will communicate program outcomes and technical complexity with clarity and confidence to senior leadership, ensuring every initiative ties directly to business impact and ROI. This role is for a builder who thrives on ownership, structure, and the satisfaction of turning messy, ambiguous problems into efficient, scalable reality.

Key facts

What you'll do

• Lead critical, high-impact technical programs across the Insurance platform, driving key technical initiatives, optimization of systems and processes, and financial remediation initiatives while owning outcomes from discovery through delivery.
• Drive end-to-end cross-team programs by coordinating cross-functional planning and execution to reduce operational costs and eliminate manual workflow inefficiencies across provider and patient experiences.
• Establish repeatable playbooks, tooling, and systematic improvements for cyclical operational challenges, transforming how teams work into predictable, efficient, and scalable processes.
• Lead key data rearchitecture initiatives, delivering on a modernization of data systems, enhancing observability, and accelerating decision-making velocity across research, development, and operations.
• Spearhead financial remediation programs across Research and Development, driving measurable year-over-year improvements in cost efficiency and resource allocation.
• Act as a strategic thought partner with Insurance team leadership to balance competing priorities, manage technical dependencies, and align on investment roadmaps that support the company's long-term vision.
• Create scalable frameworks and operating mechanisms that improve operational efficiency, enhance insurance operations reliability, and elevate team productivity across the entire software platform.
• Navigate complex stakeholder landscapes across engineering, product, operations, finance, and compliance teams to secure alignment on technical strategy, execution plans, and business objectives.
• Communicate program status, risks, and strategic decisions to senior leadership, translating intricate technical details into clear business impact, return on investment, and actionable insights.
• Partner closely with engineering leadership to identify, prioritize, and drive the execution of the company's most important technical priorities in support of product and platform goals.
• Define and manage the timeline, scope, and resourcing for large-scale initiatives, ensuring alignment with business milestones and delivery commitments.
• Identify and mitigate risks early, developing contingency plans and maintaining transparent communication to safeguard project outcomes and stakeholder confidence.
• Champion the use of data and metrics to validate program success, inform continuous improvement, and demonstrate the tangible value of technical and operational investments.
• Build and maintain trusted relationships with cross-functional partners, fostering a culture of collaboration, accountability, and shared ownership of results.
• Contribute to the development of operational standards and best practices that scale as the organization grows and the platform evolves.

Requirements

• You have successfully driven complex, high-impact programs that span engineering, operations, finance, and compliance, with proven experience owning outcomes end-to-end in a fast-paced, growth-stage environment.
• You thrive in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and define a path to execution with limited precedent.
• You are energized by transforming operational chaos into efficient, repeatable processes, turning annual scrambles into smooth, predictable cadences that scale.
• You are a natural collaborator who builds deep trust across diverse stakeholders and can influence without authority to advance priorities and get things done.
• You are a strategic thought partner who can work alongside strong Engineering and Operations leaders, balancing technical excellence with business pragmatism to achieve optimal outcomes.
• You have executive presence and the ability to communicate complex technical programs to senior leadership, translating initiatives into clear business impact, return on investment, and strategic alignment.
• You are passionate about operational efficiency and have a track record of implementing tooling, frameworks, and playbooks that deliver measurable, repeatable improvements.
• You have experience working with insurance, healthcare, or regulated environments, understanding the unique constraints and complexities of these industries.

Nice to have

• Experience implementing modern data platforms, data warehouses, or observability tools to support decision-making at scale.
• Background in billing, claims, or insurance operations systems, with an understanding of the end-to-end revenue cycle.
• Familiarity with credentialing and provider enrollment workflows within mental health or behavioral health ecosystems.
• Experience building and maintaining cross-team communication frameworks or operating rituals that improve execution velocity.
• Knowledge of compliance considerations specific to mental health services and privacy regulations.

Practical notes

This role is fully remote with no location restrictions. There may be travel requirements as business needs evolve, and candidates must be eligible to work in their country of residence without sponsorship. The position is full-time and requires dependable, consistent availability during standard business hours.