Top Tech Jobs & Startup Jobs

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.

Own the patient product experience end-to-end, prototyping in code with AI tools, partnering with PMs/engineers/researchers. Design for finding providers, benefits, booking, and engagement; run experiments with clear metrics, contribute to the Helix design system, and (at staff level) lead 0→1 work, AI-native workflows, and mentor other designers.

Lead end-to-end design for provider workflows (credentialing, scheduling, documentation, billing). Rapidly prototype in code using AI tools, run experiments with metrics, partner with PMs/engineers/researchers, contribute to the design system, and mentor peers (Staff level includes 0→1 work and org-level influence).

Lead two cross-functional engineering teams (~8 engineers plus a manager) building measurement and network intelligence for outcomes and utilization. Own delivery of a company-level outcomes metric, set technical and operational roadmaps, partner with Product/Clinical/Data Science/Commercial, mentor engineers and managers, and balance quality and adoption while scaling data- and ML-heavy systems.

Lead and grow a 5–8 engineer team building measurement, segmentation, and ranking systems to demonstrate payer value. Set technical and operational roadmap, deliver externally committed launches and metrics, partner with Product/Clinical/Data, mentor engineers and tech leads, and ensure rigorous experimentation and metric guardrails to inform payer decisions.

Lead and grow the Infrastructure team owning cloud infrastructure, deployment pipelines, LLM infrastructure, database platform, observability, and incident response. Drive platform strategy toward self-serve infrastructure, reduce blast radius, ensure reliability and performance of the FastAPI/Python monolith on AWS, and partner with Security and product teams to define production readiness for AI workloads.

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.

Lead development of AI-powered patient experiences: LLM-driven intake and therapist matching, between-session support, evaluation and safety infrastructure, outcome measurement, and HIPAA-compliant product delivery. Partner with Engineering, ML, Data Science, Clinical, and Legal to ship and monitor models in production, write evals, design red-teaming and human-in-the-loop flows, and measure patient outcomes.

Own and architect Headway's cloud platform: deployments, autoscaling, capacity, container footprint (ECS/EKS), networking, Terraform self-serve, cost attribution, and Python monolith runtime health to make infrastructure safe, scalable, and self-serve for engineers.