Jobs at Headway

Partner with cross-functional leaders to translate business plans into financial plans, drive capital allocation, build business cases, own budgeting and forecasting, analyze variances, and define trusted KPIs. The role influences strategic decisions across Product, Sales, Marketing, Operations, and People while applying AI tools to improve financial analysis and decision-making.

Design end-to-end experiences for group practices, owning onboarding, supervisory billing, admin tooling, packaging, and practice-level analytics. Partner with Sales, Customer Success, Product, and Engineering to drive growth, scale supervisory billing nationwide, and contribute AI-driven prototyping and design system improvements.

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 the product strategy and delivery of Headway’s payer and patient outcomes data infrastructure. Build patient segmentation, cost-of-care measurement, and payer-facing data products while defining data architecture and priorities. Partner closely with data engineering, data science, clinical strategy, and commercial teams to create auditable, predictive, and externally defensible outcomes and cost insights.

Lead the Ranking & Relevance team of software and machine-learning engineers. Own retrieval, ranking, recommendation, and personalization systems that match patients with therapists. Drive the transition from filter-based matching to outcome-aware machine learning, establish shared marketplace objectives, improve experimentation and model monitoring, and build evaluation and drift-detection capabilities. Hire and develop engineers, set technical standards, and partner with product, data science, payer, and provider engineering teams in a sensitive healthcare domain.

Partners with Engineering leaders to develop and execute people strategies supporting organizational scale. Advises managers and employees on performance management, talent planning, organizational design, leadership development, and employee experience. Uses workforce data and AI tools to identify trends and guide decisions, coaches managers, leads HR programs end to end, and collaborates with compensation, People Operations, Legal, and Talent Acquisition teams.

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 provider-facing client management product experience across scheduling, availability, messaging, client lists, and intake. Lead the 0-to-1 strategy and execution of AI-powered front-desk workflows, determining automation and human-in-the-loop boundaries. Develop product strategy, roadmap, and success metrics while partnering with engineering, design, data, and clinical teams to deliver reliable, intuitive experiences that improve provider engagement, retention, and patient access.

Lead and grow a data science team focused on provider experience. Define strategy, build roadmaps, run analyses, experiments, and predictive models, surface insights, and partner cross-functionally to drive measurable improvements in provider engagement and product experience.

Lead commercial data science for Headway's commercial business: own roadmap, run proactive strategic analyses for executive accounts, monitor key metrics, enable self-service analytics, mentor data scientists, and translate technical findings into actionable recommendations tied to measurable outcomes.

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 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.

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.