• Own the full product lifecycle: discovery, prioritisation, specs, delivery, and iteration • Map current manual operations (partner analytics, escalations, write-offs, refunds, chargebacks) and systematically eliminate them through product solutions • Build a product that surfaces cost-reduction opportunities automatically • Design partner-facing flows that resolve issues without human escalation • Define and instrument the metrics that prove the product is working • Work directly with engineering and data teams to ship • Identify and integrate tooling that reduces manual overhead across the team • Deliver a long-term initiatives roadmap with clear, measurable financial impact

• Own and evolve the strategic roadmap for PHIL’s external integrations including electronic health records, payers and plans, third party providers, etc., linking high-level business strategy to technical requirements and product outcomes. • Benchmark against industry best practices, and build a plan to achieve best-in-class service offerings based on strategic direction and priorities. • Solve complex problems efficiently by driving significant improvements in quality and speed through optimized processing and judicious use of platform capabilities vs internal development. • Develop and champion new platform capabilities to support expanded therapeutic categories and patient therapy management. • Set long-term success metrics and operational KPIs, and ensure the product roadmap is tightly aligned with measurable outcomes. • Act as a venturesome industry leader, identifying and evaluating third-party systems and service providers to keep PHIL at the forefront of the health-tech landscape. • Lead cross-functional partnership with senior stakeholders across Product, Engineering, Operations, and Commercial teams to define priorities and deliver value. • Lead discovery efforts and user research to identify top opportunities to deliver value, and ruthlessly prioritize to maintain organization focus. • Mentor product team members and elevate the overall product team capability through thought leadership, strategic rigor, and operational depth

• Partner closely with sales, account management, marketing, finance, and leadership teams to standardize workflows, improve systems of record, and shape how AI becomes embedded in the day-to-day operation of the Commercial organization. • Identify opportunities to build, test, and deploy AI-powered tools, workflows, and interfaces that help teams access information, automate work, and make better decisions.

1 in 4 people in the US have a treatable mental health condition, but most providers don't accept insurance, making therapy too expensive for most people. Headway’s mission is to fix this by building a new mental healthcare system everyone can access. We started by solving the biggest barrier to care: insurance. The admin work - credentialing, claims, payment reconciliation - is a nightmare. We've automated that. But we're going further. Over 75,000 providers across all 50 states run their practice on our software, serving over 1 million patients. We are building the best tools for therapists to run their entire practice, reimagining the experience of finding a therapist, and investing in the platform foundations to enable this at scale. We aren't just a billing layer; we are becoming the platform where care actually happens. We're a Series D company with $325M+ in funding (a16z, Accel, Spark Capital, etc.), looking for exceptional people to help us achieve this mission. We want your time here to be the most meaningful experience of your career. Join us, and help change mental healthcare for the better. About This Role: Every month, hundreds of thousands of patients and providers interact with Headway's support systems. Today, most interactions are handled by human agents working across disconnected tools. We believe CX is a product, not just a department — and the right product leader can transform how Headway supports its customers while dramatically improving both satisfaction and cost efficiency. As Director of Product for CX, you will build Headway's CX product function from the ground up. You'll own the product vision and strategy for how patients and providers get help — from AI-powered self-resolution to context-aware agent tooling to the feedback loops that connect support insights back to the product. You will: - Define the vision and strategy for Headway's CX product — spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and the feedback loops that connect support insights back to the product. - Build and lead a team of product managers focused on reducing cost-to-serve while increasing resolution quality and customer satisfaction. - Own the AI resolution layer — build the agentic workflows and API integrations that enable the AI agent to actually resolve problems, not just answer questions. Define the autonomy framework: what AI handles without human involvement, what needs guardrails, and what requires a human. - Build proactive engagement — systems that contact customers before they discover problems. Shift Headway's CX from reactive to proactive. - Launch and unify all contact channels — email, text, and voice — with intelligent routing that delivers differentiated experiences based on customer context, value, and issue type. - Own the knowledge and quality layer — machine-readable SOPs, AI evaluation frameworks and crisis escalation pathways. - Partner deeply with CX Operations to build agent tooling that makes human agents dramatically more effective — AI copilot, full journey context, auto-generated summaries. - Close the feedback loop: build the system that identifies the highest-impact product defects driving support volume and surfaces them to insurance platform teams for upstream fixes. - Establish measurement frameworks that connect CX product investments to business outcomes.. You'd Be a Great Fit If... - You are a product leader with 8+ years of experience, including at least 3 years managing PMs, with a track record of building CX/support products at scale. - You have a strong point of view on how AI will transform customer support — and you've shipped AI-powered CX products. - You've launched or scaled multi-channel CX systems and used intelligent routing for personalized experiences. - You've demonstrated the ability to simultaneously reduce support costs and improve customer satisfaction. - You thrive at the intersection of product and operations. - Nice to have: experience in healthcare, insurance, or other industries with complex customer interactions. Compensation and Benefits: The expected base pay range for this position is $300,000 - $375,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for an equity grant, depending on the position and level. We are committed to offering a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Compensation decisions are made holistically, ensuring fairness and alignment with market benchmarks while recognizing individual contributions and potential. - Benefits offered include: - Equity compensation - Medical, Dental, and Vision coverage - HSA / FSA - 401K - Work-from-Home Stipend - Therapy Reimbursement - 16-week parental leave for eligible employees - Carrot Fertility annual reimbursement and membership - 13 paid holidays each year as well as a Holiday Break during the week between December 25th and December 31st - Flexible PTO - Employee Assistance Program (EAP) - Training and professional development We believe a team's strength is in its people, and we cannot achieve this mission without a team that reflects the diversity of this problem – across race, ethnicity, gender, sexuality, age, national origin, religion, family status, disability, military status, and experience. Headway is committed to the full inclusion of all qualified individuals. As part of this commitment, Headway will ensure that persons with disabilities are provided with reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or receive other benefits and privileges of employment, please inform the recruiter when they contact you to schedule your interview. Headway participates in E-Verify. To learn more, click here. A notice to Headway applicants: To protect yourself against phishing and recruitment fraud, please note that Headway only accepts applications through our official careers page at https://headway.co/careers. Headway will never refer you to external websites, ask for payment or personal information, or conduct interviews via messaging apps. All official communication will come from a @findheadway.com email address. If you are contacted by someone claiming to be from Headway via an unofficial channel, please do not share any information and report it as spam.