Jobs at Headway

Leads and coaches a team of 6–7 recruiters supporting Provider Sales and Care Partnerships. Owns recruiting strategy, complex requisitions, sourcing, process design, pipeline health, offer closing, recruiting metrics, stakeholder partnerships, interviewer training, and process improvement. Serves as an executive-facing talent advisor while driving consistent, inclusive, data-informed hiring practices in a high-growth environment.

Own the strategy and execution of new payer partnerships with U.S. health plans. Lead contract expansion, including value-based arrangements and lines of business, while shaping scalable mental healthcare networks and expanding affordable coverage. The role requires deep payer economics knowledge, end-to-end business development experience, strong relationship-building skills, operational excellence, and the ability to navigate ambiguity and drive strategic outcomes.

Lead Headway’s Infrastructure team, owning AWS cloud infrastructure, deployment pipelines, LLM platform capabilities, databases, observability, reliability, and incident response. Hire and develop engineers, establish self-service platform practices, reduce incident blast radius, define production readiness for AI workloads, and partner with Security and product engineering teams. The role combines technical leadership, people management, platform strategy, design reviews, and hands-on incident response.

Own day-to-day performance of outsourced BPO partners supporting patient-facing customer experience. Track metrics, identify root causes, lead improvement initiatives, align partner and internal teams, and build scalable processes. Manage BPO leadership relationships while improving conversion, quality, responsiveness, and patient satisfaction. Contribute to short-, medium-, and long-term BPO operations strategy.

The Chief of Staff will support the Clinical leadership team by driving cross-functional initiatives, managing operating rhythms, leading OKR and planning processes, coordinating meetings and onsites, drafting leadership communications, and developing durable governance processes. The role requires strong program management, organizational skills, writing ability, influence without authority, and comfort operating in ambiguity within a healthcare technology environment.

Lead Headway’s Web Platform team of five frontend engineers. Own frontend strategy, design systems, web architecture, accessibility, performance, testing, and agentic UI workflows. Hire and develop engineers, manage performance, align with Design and product teams, define roadmaps and metrics, and advocate for frontend standards company-wide. Remain hands-on with code and AI tools while evolving shared frameworks, tooling, documentation, and automated quality checks.

Leads clinical product strategy for payer and outcomes initiatives, translating behavioral health workflows, reimbursement requirements, and quality standards into product requirements. Partners with product, engineering, data, payers, and health systems to measure outcomes, improve clinical quality and safety, influence roadmaps, and represent Headway externally. Requires an active psychologist or psychiatrist license, extensive clinical experience, payer-facing expertise, claims or outcomes experience, and strong analytical and presentation skills.

Lead clinical product strategy for a digital mental healthcare platform. Embed behavioral health expertise into product design, AI governance, patient safety, clinical quality, and measurable outcomes. Translate clinical workflows into product requirements, guide safe AI-enabled features, monitor provider and patient outcomes, and align product, design, data, and engineering teams. The role requires a licensed psychiatrist or psychologist with substantial clinical experience and prior collaboration with product and engineering teams.

Evaluate AI-generated outputs for clinical accuracy, safety, and appropriateness across patient and provider products. Apply and refine evaluation rubrics, document clinical reasoning, participate in calibration and inter-rater reliability reviews, provide structured feedback to Clinical Product teams, label datasets, and review product use cases. Work within designated systems while maintaining HIPAA compliance and patient confidentiality.

Build and manage patient lifecycle campaigns across email, SMS, push, and in-app channels. Own audience segmentation, campaign QA, experimentation, holdout measurement, and retention optimization. Partner with Product, Engineering, and Data Science to instrument events, develop notification infrastructure, and apply predictive personalization signals such as churn propensity and appointment readiness. The role requires hands-on campaign execution, strong lifecycle platform expertise, data fluency, and comfort operating in an ambiguous environment.

Leads patient and brand marketing strategy, product marketing, media planning, influencer campaigns, partnerships, creative strategy, and brand measurement. Owns awareness, trust, patient acquisition, funnel conversion, and marketing efficiency while managing budgets, testing campaigns, and building a high-performing marketing team. Partners across product and brand functions to create differentiated healthcare experiences and drive company growth.

Own the Supervisory Billing product end to end, including strategy, roadmap, revenue growth, state and payer expansion, operational scaling, and new product development. Lead cross-functional initiatives to expand the addressable market, improve efficiency for thousands of customers and appointments, and launch concepts such as a supervisor-supervisee marketplace.

Build and lead product and application security efforts, partnering with Product and Engineering on secure design, development, code reviews, vulnerability discovery, and security guardrails. Develop AI-native security tooling and support incident response, vulnerability management, penetration testing, and security operations. Help establish secure development practices and scalable security systems across Headway’s platform.

Leads and coaches a pod of 7–8 Business Development Associates responsible for outbound meeting generation. Owns funnel performance, quotas, qualification targets, coaching, call reviews, experimentation, hiring, and onboarding. Partners with regional and business development leaders to improve handoffs and meeting quality. The role has no individual quota and focuses on developing representatives and scaling outbound sales processes for healthcare partnerships.

Own Headway’s provider lifecycle marketing program end to end, from segmentation and trigger design through campaign deployment in Iterable and Intercom. Build journeys that improve provider activation, product adoption, engagement, and retention. Develop experiments, define success metrics, analyze performance, and continuously optimize programs. Partner with Product, Product Marketing, Customer Success, and Creative to align lifecycle campaigns with product priorities and create consistent provider experiences.

Leads provider growth marketing to expand Headway’s provider network and improve acquisition efficiency. Owns paid, organic, lifecycle, referral, segmentation, experimentation, channel strategy, and performance measurement. Builds and manages the marketing team while partnering with Sales, RevOps, Finance, Product, and R&D to align growth goals, reduce CAC, optimize provider mix, and develop value-based acquisition frameworks.

Lead data recruiting across Data Science and Data Engineering, managing and developing a team of recruiters. Partner with senior data leaders to design hiring strategies, use metrics and market insights to improve recruiting funnels, and deliver high-quality hiring outcomes. Establish operational standards, prioritize critical hiring initiatives, remove obstacles, and serve as a trusted advisor while building a scalable, high-performing recruiting organization.

Own Headway’s enterprise payer product strategy, partnering with strategic payer accounts, Payer BD, Data, and Engineering. Translate commercial needs into reusable product capabilities, establish a repeatable enterprise product framework, and support procurement, legal, and multi-stakeholder buying processes. The role requires balancing enterprise rigor with startup speed while building the function from scratch.

Drive high-volume outbound outreach through phone, email, and LinkedIn to generate qualified meetings with care management leaders at health systems. Responsibilities include prospect qualification, contact-list development, CRM activity documentation, clean handoffs to the business development team, and collaboration on messaging and outreach strategy. The role also contributes insights on personas, objections, and conversion performance to improve the team's sales playbook.

Own third-party and vendor contracting, AI-assisted contract review, escalated disputes and regulatory inquiries, corporate insurance administration, and other corporate risk matters. Partner with Procurement, Finance, Customer Experience, and Communications in a fast-growing healthcare technology company. Translate legal risks into actionable guidance, manage complex processes, and resolve sensitive matters with sound judgment and strong cross-functional collaboration.