Chief of Staff supporting Payer Partnerships and Clinical organizations. Translates executive strategy into cross-functional goals, drives initiative execution, tracks blockers, manages operating cadences, facilitates leadership decisions, writes decision memos and communications, and improves organizational processes. The role requires influencing without authority, managing multiple workstreams, bringing structure to ambiguity, and leading initiatives across Commercial, Clinical, R&D, Finance, Product, and other teams.

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.