Top Engineering Jobs

Own Headway’s cloud platform and infrastructure engineering strategy. Lead deployment isolation, container orchestration, AWS networking and compute, autoscaling, capacity planning, Terraform self-service infrastructure, cloud cost attribution, and Python runtime performance. Build reliable paved-road tooling that enables engineering teams to deploy safely and independently while improving scalability, observability, and operational resilience.

Lead the technical strategy and evolution of Headway’s billing platform, including a financial state-machine orchestration layer, guardrail APIs, remittance ingestion, refunds, recoups, reconciliation, and explainability. Manage platform engineering teams, establish technical standards, coordinate cross-functional dependencies, and partner with Finance and Accounting to ensure accurate, auditable financial records at significant scale.

Own escalated IT support issues and identify systemic fixes. Manage network health, wireless infrastructure, VLANs, multi-ISP failover, and conference room AV across three offices. Provide after-hours and event-day support, administer identity, collaboration, service management, and endpoint platforms, and deliver office technology projects from design through cutover. Build automation, monitoring, documentation, and runbooks while partnering with Workplace Experience, Security, and Employee Experience.

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.

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.

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.

Own architecture and technical direction for Headway's Journey communications platform: design the decision engine, experimentation layer, channel orchestration, unified message ledger, and productionize LLM-powered personalization across multi-vendor delivery systems to improve patient and provider engagement.

Own and build Headways experimentation platform: assignment, exposure, identity resolution, feature flags, and data pipelines. Drive technical direction, reliability, and company-wide experimentation practices, integrate AI for diagnostics, and enable market-level tests across teams.