Headway
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Consumer Web • Healthtech • Professional Services • Social Impact • Software
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.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
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.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
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.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Build, deploy, and iterate AI-powered revenue workflows to automate and scale provider GTM motions. Lead end-to-end Rev Ops initiatives from problem definition and data analysis through implementation, partnering with R&D and Data teams. Shadow reps to design usable processes, measure performance via quantitative analysis, and drive adoption and continuous optimization of AI-native tools and systems.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
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.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
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.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead and grow the Web Platform engineering team through people development, strategic planning, and cross-functional partnership. Define and advocate platform roadmap, drive platform investments that enable product goals, align multiple product teams, and ensure visibility through documentation, metrics, and stakeholder engagement.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead Headway's AI platform vision and roadmap, own the internal assistant Eddy, write evals and prompts, configure agents and integrations, and partner with CX, Ops, Sales, Finance, and Clinical teams to identify high-value AI workflows and drive adoption across the company.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead a backend engineering team owning Headway's billing and claims systems: design architecture, ensure financial correctness and observability, run incidents/on-call, hire and grow engineers, partner cross-functionally with Product, Data, Operations, Finance, and drive a roadmap for reliable money movement.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead a major product domain end-to-end at Headway, defining strategy, shipping AI-enabled features, building long-lived platform foundations, mentoring PMs, and aligning cross-functional stakeholders to drive measurable outcomes for patients, providers, payers, and platform infrastructure.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Design, standardize, and automate the IAM lifecycle and workflows. Integrate and maintain IdP connections, drive RBAC/least-privilege adoption, automate provisioning/deprovisioning, resolve identity incidents, document processes, and partner with stakeholders to establish IAM governance.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Own strategy and roadmap for core insurance/payment platforms, driving claims processing through reconciliation. Design automated workflows with robust exception handling, reduce financial leakage, build internal tooling for operations, and lead cross-functional initiatives with Engineering, Data, Operations, and Finance to improve provider and patient payment experiences.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead design for calendar, scheduling, and provider-patient messaging to reduce administrative burden for therapists. Solve complex multi-state problems (timezones, booking, conflicts), improve notifications and EHR usability, conduct research with providers, contribute patterns to the Helix design system, and prototype using AI tools through launch and iteration.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead the end-to-end design of the provider CRM and AI front-desk/scheduling assistant, turning client lists into a prospect pipeline. Define stages, signals, automation boundaries, and interactions for diverse providers. Prototype with AI tools, conduct provider research, partner with PM and Eng to ship 0→1 features, and contribute to the design system and AI design practices.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Design high-converting provider acquisition experiences across external landing pages, lead forms, and internal PGA tooling. Diagnose SQL→Intake-Complete funnel drop-off, run experiments, partner with Creative/PM/Eng, conduct provider and agent research, and contribute patterns to the Helix design system while using AI prototyping tools.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead full-cycle technical recruiting for engineering teams: partner with hiring managers, design sourcing strategies, run searches from intake to offer, use data to diagnose and improve searches, and ensure a structured, inclusive candidate experience while building high-quality pipelines.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead product and application security by partnering with product and engineering to design secure features, perform code and architecture reviews, build AI-native security tooling, create developer guardrails, and support incident response, vulnerability management, and penetration testing to scale Headway's security program.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead architecture and evolution of Headway's data platform (warehouse, ingestion, orchestration, CI/CD, monitoring, cloud infra). Serve as technical anchor across analytics, product, and ML teams, drive platform roadmaps, set standards, mentor engineers, and own end-to-end infrastructure decisions for scale and performance.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead and grow a data engineering team, define data platform architecture and reliability (warehouse, ingestion, transformations, orchestration), set engineering standards, partner cross-functionally to support analytics and ML, and translate technical decisions for executive stakeholders.
Consumer Web • Healthtech • Professional Services • Social Impact • Software
Lead measurement and decision systems for patient growth: own incrementality, design experiments, build LTV/retention/forecasting models, create trusted marketing metrics, partner with Engineering for measurement plumbing, diagnose performance shifts, influence channel allocation, and mentor growth analytics teams.
