Staff Technical Program Manager

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Headway

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2019

🏥 Healthcare

🏪 Marketplace

☁️ SaaS

💰 $100M Series D - Headway on 2024-07

Healthcare • Marketplace • SaaS

Headway is a healthcare technology company (Therapymatch, Inc. ) that operates an insurance-native marketplace connecting people with licensed mental health providers — therapists and psychiatrists — for in-person and online care. Headway matches users with providers by specialty, location, and insurance coverage, handles insurance verification and billing, and offers tools for providers (provider portal and an insurance-native EHR) to reduce administrative burden. The platform partners with 100+ insurance plans, supports many languages, and emphasizes affordable, in-network mental health care.

📋 Description

• Lead critical, high-impact technical programs across Insurance platform including driving key technical initiatives, optimization of systems and processes, and financial remediation initiatives—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 manual workflow inefficiencies • Establish repeatable playbooks, tooling, and systematic improvements for cyclical operational challenges, transforming how we work into predictable, efficient processes • Lead key data rearchitecture initiatives, delivering on a modernization of our data systems, observability, and accelerate 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, improve insurance operations reliability, and enhance 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

🎯 Requirements

• You've driven complex, high-impact programs that span engineering, operations, finance, and compliance—with proven experience owning outcomes end-to-end • You thrive in ambiguous, fast-moving environments where you can structure messy problems, establish clarity, and drive systematic improvements • You're energized by transforming operational chaos into efficient, repeatable processes—turning annual scrambles into smooth, predictable cadences • You're a natural collaborator who builds trust across diverse stakeholders and can influence without authority to get things done • You're a strategic thought partner who can work alongside strong Engineering and Operations leaders to balance technical excellence with business pragmatism • You have executive presence and can communicate complex technical programs to senior leadership, translating initiatives into clear business impact and ROI • You're passionate about operational efficiency and have experience implementing tooling, frameworks, and playbooks that deliver measurable improvements year-over-year • You're a force multiplier who removes blockers, accelerates decision-making, and enables teams to focus on high-value work • You're comfortable with high autonomy and can tackle technical and operational challenges across the stack with minimal guidance • You care about our mission of building a mental healthcare system that everyone can access.

🏖️ 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