Teams at Headway

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 Headway's CX product function to transform support with AI-powered self-resolution, agent tooling, multi-channel routing, proactive engagement, knowledge/quality systems, and feedback loops tying support insights to product outcomes.

Lead day-to-day accounting operations and a team of four accountants. Own month-end/quarter/year-end close, reconciliations, technical US GAAP accounting, audit support, and payroll accounting. Drive automation using LLMs/AI, implement process improvements with Netsuite/Workday/Ramp, and partner cross-functionally on strategic accounting projects and audit readiness.