Director of Product, CX Product

Headway’s mission is to build a new mental healthcare system accessible to everyone, addressing the significant barriers to care, particularly the high cost of therapy due to insurance issues.

About the role

We are seeking a Director of Product for Customer Experience (CX) to lead the transformation of how Headway supports its patients and providers. The ideal candidate will build the CX product function from the ground up, focusing on AI-powered self-resolution, agent tooling, proactive engagement, and feedback loops.

Responsibilities

• Define the vision and strategy for Headway's CX product, spanning AI-powered resolution, agent tooling, proactive engagement, channel strategy, knowledge systems, and feedback loops.
• 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, building the agentic workflows and API integrations that enable the AI agent to resolve problems effectively.
• Define the autonomy framework, determining what AI handles, what needs guardrails, and what requires a human intervention.
• 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, including 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, such as AI copilot, full journey context, and auto-generated summaries.
• Close the feedback loop by identifying the highest-impact product defects driving support volume and surfacing them to insurance platform teams for upstream fixes.
• Establish measurement frameworks connecting CX product investments to business outcomes.

Qualifications

• 8+ years of experience, including at least 3 years managing product managers.
• A strong point of view on how AI will transform customer support and a track record of shipping AI-powered CX products.
• Experience launching or scaling multi-channel CX systems and using intelligent routing for personalized experiences.
• Proven ability to simultaneously reduce support costs and improve customer satisfaction.
• Able to thrive at the intersection of product and operations.

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 offer a comprehensive and competitive total rewards package, including robust health and wellness benefits, retirement savings, and meaningful ownership opportunities through equity. Benefits 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, including a Holiday Break during the week between December 25th and December 31st
• Flexible PTO
• Employee Assistance Program (EAP)
• Training and professional development

We are committed to the full inclusion of all qualified individuals. Headway participates in E-Verify. For more information, visit our careers page.