[Hiring] Director of Product, CX Product @Headway

Role Description

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.

• 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.

Qualifications

• 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 $249,600 - $312,000, 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.

• 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