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.

Leads Headway’s real estate and workplace portfolio across New York, San Francisco, and Seattle. Responsibilities include real estate strategy, lease negotiations, subtenant management, buildouts, capital projects, facilities operations, workplace experience, budgeting, vendor oversight, and team leadership. Partners with executives and cross-functional teams to scale the company’s physical footprint, improve office experiences, and manage costs and performance metrics.

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.

Partner with Engineering leaders to develop and execute people strategies supporting organizational growth. Advise managers on performance management, talent planning, organizational design, leadership development, and employee experience. Use workforce data to identify trends and guide decisions, coach managers, lead HR programs, and collaborate with Total Rewards, People Operations, Legal, and Talent Acquisition teams. The role also promotes cultural integrity, inclusion, accountability, and scalable operational excellence.

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.

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.

Owns commercial KPI production, competitive intelligence resources, reporting cycles, and enablement infrastructure for Headway’s payer partnerships organization. The role drives strategic and operational workstreams, coordinates commercial reporting, supports team scaling, and applies AI tools critically to produce reliable recommendations. Success requires strong operational execution, resourcefulness, analytical problem-solving, and comfort working in ambiguity within a digital health environment.

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.

Own the operating rhythm and planning system for Headway’s R&D organization. Responsibilities include quarterly and annual planning, headcount and capacity prioritization, leadership meetings, board preparation, decision memos, escalation processes, organizational design, budget governance, and cross-functional alignment across Product, Engineering, Data, and Design. This Director-level individual contributor role solves high-priority, ambiguous organizational problems and drives execution through influence rather than authority.

Lead payer-facing commercial efforts: own market and buyer analysis, prioritize partners, develop deal content and executive briefings, drive negotiations and recurring external relationships, and use AI tools to inform and validate recommendations while reporting to a Managing Principal.

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.