Jobs at Headway

Lead Headway’s Talent Intelligence and Early Careers Recruiting function. Build teams, campus recruiting strategy, talent mapping, sourcing infrastructure, internship programs, market intelligence, reporting, and long-term candidate pipelines. Partner with recruiting, HR, and business leaders to plan hiring capacity, improve sourcing, manage university relationships, deliver internships and events, and own defined hiring outcomes across technical and business functions.

Build and mature Headway’s infrastructure security program across AWS and application platforms. Partner with Product and Infrastructure teams on secure system design, security reviews, platform guardrails, vulnerability remediation, and continuous infrastructure improvement. Support incident response and security operations while advancing AI-native cloud security practices. The role requires strong technical depth, cross-functional collaboration, and the ability to establish secure-by-default engineering practices in an ambiguous, fast-paced environment.

Own Headway’s provider activation funnel, onboarding strategy, patient porting tools, and early provider appointment growth. Define activation metrics, OKRs, and roadmap while partnering cross-functionally with sales, CX, finance, pricing, ranking, and provider experience teams to improve retention, lifetime value, and provider satisfaction.

Lead end-to-end quantitative market research, including research planning, surveys, advanced statistical analysis, synthesis, and stakeholder presentations. Build and manage brand and sentiment measurement programs, identify customer and market trends, and provide strategic recommendations for growth and product opportunities. Partner with business leaders, promote research-driven decision-making, and mentor junior researchers while scaling the organization’s research practice.

Own the patient search results experience, including provider cards, ranking explanations, filters, sorting, and empty states. Design and evaluate sustained experiments on a conversion-critical surface, collaborate with product, engineering, research, data, and ranking teams, and iterate on shipped experiences. Use AI tools and code-based prototyping to develop high-craft solutions, improve the design system, and help patients make confident therapist choices.

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.

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.

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 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.

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.