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.

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.

Owns the clinical organization’s governance and operating system, including committee operations, OKRs, policy lifecycle, clinical programs, risk registers, reporting, and cross-functional coordination. The role leads through influence while clinical leaders retain decision rights and accountability for clinical outcomes. Candidates need an active clinical license, substantial mental health experience, governance and policy expertise, strong program execution, data fluency, and the ability to build scalable systems in an ambiguous, technology-enabled healthcare environment.

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. Responsibilities include performance management, talent reviews, organizational design, workforce planning, manager coaching, leadership development, employee experience, people analytics, and end-to-end HR program execution. The role uses data and AI tools to identify workforce trends, influence decisions, strengthen manager capabilities, and promote a fair, inclusive, high-performance culture.

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.

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.

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.

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.

Own and improve Headway’s privacy program across HIPAA, 42 CFR Part 2, state privacy laws, individual rights, incidents, vendor governance, and AI use. Maintain controls, data maps, metrics, training, and operational workflows. Conduct product, vendor, and AI privacy assessments; manage rights requests and incident investigations; coordinate notifications and regulatory submissions; and translate complex requirements into practical guidance for cross-functional teams.

Owns Headway’s patient safety triage operations, including SOPs, quality assurance, escalation workflows, clinical product launch readiness, safety reporting, dashboards, vendor management, and incident response. The role coordinates clinical, product, and engineering teams, drives quality improvement initiatives, and builds scalable systems and reporting for clinical leadership and the Board.

Own the strategy and roadmap for patient-provider search, retrieval, ranking, and marketplace matching. Lead experimentation, objective functions, evaluation, and ML platform foundations while partnering with ML engineers, data scientists, design, clinical teams, and executives. Improve successful, lasting care matches rather than optimizing only clicks or bookings. Balance patient access, provider growth, clinical quality, and payer priorities, while setting the standard for technically grounded product management.

Provide empathetic customer support to healthcare providers and patients through email, live chat, and phone. Resolve approximately 40 daily operational and technical inquiries, explain Headway’s products and insurance practices, de-escalate challenging situations, and identify customer experience improvements. The role requires weekend availability, remote work from a quiet private workspace, and strong communication, judgment, problem-solving, and goal-oriented performance.

Lead Headway’s customer experience operation across Agent Success, Customer Care, Programs, and Systems, managing over 100 employees and 800 partner agents. Own end-to-end support quality, performance, staffing, forecasting, costs, training, QA, procedures, systems, and AI-enabled automation. Partner with Product and R&D to improve customer experience and reduce support demand while developing a high-performing leadership team.

Owns the full business development cycle for mid-market health system partnerships, including prospecting, qualification, pitching, closing, and launch. Builds relationships with care management, population health, and clinical operations leaders; develops account strategies; supports enterprise opportunities; and collaborates with Partner Success, Product, and Operations to ensure successful referrals and launches. Also mentors the BDR team.

Owns AI-powered tools and strategic analytics for Headway’s provider growth and revenue operations. Responsibilities include optimizing provider outreach and conversion, analyzing funnel trends, pipeline health, and cohort performance, supporting weekly business reviews and executive reporting, and enabling sales leaders to self-serve performance insights. The role requires strategic initiative ownership, strong analytical and forecasting skills, and collaboration with revenue leadership in a growth-stage environment.