Senior Manager, Agent Success

Summary

Join Headway and help transform mental healthcare! As a Senior Manager of Agent Success, you will lead Enablement, Knowledge Management, and QA teams, developing and executing a cohesive strategy to enhance customer experience. You will build scalable enablement programs, maintain an accurate knowledge base, oversee quality assessment, and collaborate with cross-functional teams. This critical leadership role directly impacts customer satisfaction and agent performance. The ideal candidate possesses 7+ years of experience in customer experience operations and a proven track record of developing high-performing teams. Headway offers a competitive compensation package including base pay, variable compensation, equity, and comprehensive benefits.

Requirements

• Have 7+ years in customer experience operations, enablement, or quality assurance leadership, ideally in high-scale environments
• Are a proven people manager with a track record of developing high-performing teams
• Are data-driven and skilled at translating performance metrics into actionable improvements
• Have experience building scalable enablement and QA programs for internal and outsourced teams
• Are highly organized, operationally excellent, and adept at leading in complex, fast-paced environments
• Have strong collaboration and influencing skills with the ability to align multiple stakeholders

Responsibilities

• Lead the Enablement, Knowledge Management, and QA teams, ensuring strategic alignment and collaboration across pillars
• Develop and execute a cohesive Agent Success strategy informed by QA insights and operational data
• Build scalable, high-impact enablement programs for onboarding, ongoing training, and continuous skill development
• Ensure our knowledge base is accurate, accessible, and integrated into workflows for maximum efficiency
• Oversee quality assessment programs to monitor and improve agent performance across all support channels
• Create feedback loops between QA, enablement, and knowledge to continuously improve processes and outcomes
• Partner with cross-functional teams (WFM, Vendor Management, Product, Data) to support operational priorities and drive results

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 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