[Hiring] Director of Customer Experience Operations @Headway

Role Description

As Director of Customer Experience (CX) Operations, you will lead the entire CX operation across Agent Success, Customer Care, Programs, and Systems, an operation of more than 100 Headway employees and over 800 partner agents, reporting to the Head of Operations. You will be directly responsible for customer experience at Headway and will represent the function to the executive team. This is a senior leadership role for a driver who can turn ambiguity into clarity, build a high-performing team, and create the support operation a fast-growing consumer healthcare business needs to win.

What You'll Do

• Own the customer experience end to end, setting the standard for great support at Headway for both patients and providers.
• Lead and grow the team across Agent Success, Customer Care, Programs, and Systems.
• Bring AI into the operation to enhance the customer experience.
• Own capacity and cost, building an operation that scales with growth.
• Build the engine behind great support, including training, quality assurance, and technology.
• Be the customer's voice inside R&D, using evidence from contacts to influence improvements.

Qualifications

• 10+ years in customer experience, support, or service operations and strategy, including 5+ years leading teams of managers.
• Experience running a blended internal and outsourced support organization at the scale of several hundred agents.
• Ownership of cost lines, demand forecasting, capacity planning, and headcount ownership.
• Experience leading a support organization through an AI or automation transition.
• Deep knowledge of the CX landscape and tooling stack, with an AI-native approach.
• Experience partnering closely with R&D to influence product development.
• Commitment to advancing Headway's mission to make mental healthcare more accessible and affordable.
• Nice to have: experience in healthcare, insurance, or industries with complex customer interactions.

Requirements

• Ability to turn ambiguity into clarity.
• Experience in building high-performing teams.
• Capability to set quality standards and accountability for operations.
• Experience in managing performance and commercial commitments with partners.
• Understanding of how to leverage AI for better customer experiences.

Benefits

• 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 plus a Holiday Break between December 25th and December 31st.
• Flexible PTO.
• Employee Assistance Program (EAP).
• Training and professional development.