Senior Manager, Agent Success

About Headway

Headway’s mission is to build a new mental health care system everyone can access. We’ve built technology that helps people find great therapists with the first software-enabled national network of providers accepting insurance.

1 in 4 people in the US have a treatable mental health condition, but the majority of providers don’t accept insurance, making therapy too expensive for most people. Headway is building a new mental healthcare system that everyone can access by making it easy for therapists to accept insurance and scale their practice.

Headway was founded in 2019. Since then, we’ve grown into a diverse, national network of over 45,000 mental healthcare providers across all 50 states who run their practice on our software and have served over 1 million patients. We’re a Series D company with over $325m in funding from a16z (Andreessen Horowitz), Accel, GV (formerly Google Ventures), Spark Capital, Thrive Capital, Forerunner Ventures and Health Care Service Corporation.

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 the Role

The Agent Success function ensures that our Customer Experience teams are consistently equipped, supported, and enabled to deliver an exceptional customer experience at every interaction.

We’re seeking a Senior Manager, Agent Success to lead and integrate our Enablement, Knowledge Management, and QA programs. You’ll manage an established team, bring strategic leadership, and build scalable operating systems to drive excellence across our frontline operations. This is a critical leadership role that will have a direct impact on customer satisfaction, operational efficiency, and the performance of hundreds of agents.

You Will

• 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

You’d be a great fit if you:

• 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.

Compensation and Benefits

The expected base pay range for this position is $130,560 - $192,000, based on a variety of factors including qualifications, experience, and geographic location. In addition to base salary, this role may be eligible for performance-based variable compensation and 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, Dent