Jobs at Headway

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.

Serve as the primary product attorney and regulatory advisor to Product, Engineering, and Operations teams. Provide practical guidance on AI, data use, healthcare technology, clinical modalities, and applicable regulations. Translate complex legal requirements into actionable tools, anticipate regulatory risks, support product innovation, and balance business objectives with risk. Build cross-functional partnerships in a fast-paced healthcare technology environment.

Lead and build Headway's payer marketing function: set strategy, craft positioning and narratives, commercialize payer solutions, translate clinical data into commercial proof, enable sales and field teams, run events and competitive intelligence, and measure relationship and commercial impact.

Lead end-to-end, high-impact technical programs for Headway's Insurance platform. Coordinate cross-functional teams (engineering, product, ops, finance, compliance), own discovery through delivery, drive data rearchitecture and observability, establish repeatable playbooks and tooling, spearhead financial remediation, and communicate program status and ROI to senior leadership to improve operational efficiency and reliability.

Lead day-to-day accounting operations and a team of four accountants. Own month-end/quarter/year-end close, reconciliations, technical US GAAP accounting, audit support, and payroll accounting. Drive automation using LLMs/AI, implement process improvements with Netsuite/Workday/Ramp, and partner cross-functionally on strategic accounting projects and audit readiness.

Own long-term health plan partnerships, drive contract strategy and renegotiations, build cross-functional payer relationships, perform market and data-driven analyses to identify growth opportunities, and collaborate with product and operations to inform strategy and scale partnerships.

Build and own analytics and AI-driven reporting for Care Partnerships. Create self-service insights, predict partner health, prioritize outreach, instrument experiments and launch analytics infrastructure to scale referrals and partner relationships.

Lead cross-functional, high-impact initiatives across Product, Data, and Operations. Design and scale 0-1 initiatives, build repeatable processes, analyze complex data to set strategy, drive OKRs, and hire and manage a growing operations team to improve provider and patient outcomes.

Lead development of a unified billing platform and ledger to ensure correct appointment billing, reliable reconciliation, and trusted financial datasets and reports. Own architecture and roadmap for ledger, reconciliation, and data-integrity systems; partner with Engineering, Data, Finance, Accounting, and Compliance to improve payment health, automate reconciliation, and enable accurate, timely close and audit readiness.

Run and scale Talent Acquisition enablement and AI-adoption programs: design training and onboarding for recruiters and hiring managers, define success metrics, build dashboards, document processes, and partner cross-functionally to measure and iterate program impact.

Lead development of Headway's brand strategy and creative direction across campaigns, product launches, and experiences. Partner with Customer Insights to ground briefs, run cultural listening, maintain competitive differentiation, steward brand systems and guidelines, build scalable brand tools (including AI agents), educate internal teams, and measure brand health and creative effectiveness to iterate on strategy.

Own and publish enterprise contact-center schedules in Verint, manage rosters and headcount across internal and BPO teams, reconcile scheduled vs. invoiced hours, handle exceptions and intraday adjustments, drive quarterly scheduling optimization and policy, and govern AI-assisted scheduling drafts to improve staffing efficiency and agent wellbeing.

Lead design and implementation of Headway's insurance systems (eligibility, pricing, matching, claims). Build data-intensive, ML-powered platforms and automation, mentor engineers, write high-impact code, and improve accuracy and reliability across state and payer complexity to scale insurance-covered therapy.

Lead strategy and execution for Headway’s provider community and content programs. Define member journeys, manage channels and events, build an ambassador program, capture provider stories, and measure engagement to drive business outcomes and provider advocacy.