Top Tech Jobs & Startup Jobs

Design end-to-end experiences for group practices, owning onboarding, supervisory billing, admin tooling, packaging, and practice-level analytics. Partner with Sales, Customer Success, Product, and Engineering to drive growth, scale supervisory billing nationwide, and contribute AI-driven prototyping and design system improvements.

Own the operating rhythm and planning system for Headway’s R&D organization. Responsibilities include quarterly and annual planning, headcount and capacity prioritization, leadership meetings, board preparation, decision memos, escalation processes, organizational design, budget governance, and cross-functional alignment across Product, Engineering, Data, and Design. This Director-level individual contributor role solves high-priority, ambiguous organizational problems and drives execution through influence rather than authority.

Lead and scale technical recruiting across Engineering, Data, Product, Design, Security, and IT. Build and manage a high-performing team of senior recruiters and managers, set strategy and operating model, partner with R&D leaders on headcount planning, improve systems and tooling, and drive operational excellence and talent-branding to deliver high-impact hiring outcomes.

Lead payer-facing commercial efforts: own market and buyer analysis, prioritize partners, develop deal content and executive briefings, drive negotiations and recurring external relationships, and use AI tools to inform and validate recommendations while reporting to a Managing Principal.

Headway is hiring an FP&A Manager to be an embedded finance partner across major departments, lead financial deep dives and ad-hoc analyses, consolidate company performance, and drive strategic planning. The role shapes investment decisions, pressures plans, and applies AI to accelerate insights and efficiency across FP&A while translating complex analysis into clear business recommendations.

Build and lead Headway's procurement function: define procurement strategy and policy, manage vendor lifecycle, drive cost optimization and strategic sourcing, implement procurement tooling and reporting, advise leadership on governance and risk, and hire and develop a high-impact procurement team.

Provide strategic regulatory counsel to Clinical, Product, Engineering, and Operations teams on telehealth, clinical practice, and multi-state healthcare compliance. Draft policy, support audits and remediation, translate complex regulations into practical guidance, anticipate regulatory risks, and enable compliant product innovation while partnering cross-functionally.

Lead and build Headway's payer marketing function: set strategy, craft positioning and narratives, commercialize payer solutions, translate clinical data into commercial proof, enable sales and field teams, run events and competitive intelligence, and measure relationship and commercial impact.

Lead end-to-end, high-impact technical programs for Headway's Insurance platform. Coordinate cross-functional teams (engineering, product, ops, finance, compliance), own discovery through delivery, drive data rearchitecture and observability, establish repeatable playbooks and tooling, spearhead financial remediation, and communicate program status and ROI to senior leadership to improve operational efficiency and reliability.

Lead and grow the Data Safety engineering team to enable safe use of highly sensitive mental-health data. Own de-identification, access controls, entitlements, LLM data handling, and compliance audit evidence. Partner with Security, Legal, Compliance, Data Platform, and product teams to set roadmap, deliver privacy commitments, and enable company-wide safe data practices.