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 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.