Senior Director – Customer Success

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October 7

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First Stop Health

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Healthcare Insurance • B2B • B2C

First Stop Health is a comprehensive virtual healthcare provider that offers a range of services including urgent care, primary care, mental health counseling, and health coaching. Designed for both individuals and businesses, First Stop Health aims to create a delightful healthcare experience by providing accessible, affordable, and engaging care options. Their team consists of board-certified doctors, registered dietitians, health coaches, and licensed therapists who collaborate to support the complete health journey of their patients, ensuring that care is available anytime, anywhere, through a user-friendly digital platform.

51 - 200 employees

Founded 2011

⚕️ Healthcare Insurance

🤝 B2B

👥 B2C

📋 Description

• Maintain accountability for ~$45M+ in existing business and same growth in 2026 (expectation of quota growth 40% YoY) • In partnership with CS leadership, set, lead, and execute renewal and growth strategy — driving expansion and upsell within existing accounts • Ensure the team delivers exceptional service and cultivates executive-level client and broker relationships that foster long-term loyalty • Build and operationalize systems to anticipate churn, proactively manage book health, and mitigate risks before they surface • Leverage client health metrics to drive insights, flag risks early, and activate data-driven action plans that ensure satisfaction and renewal • Act as the key point of escalation for complex client needs and broker relationships, reinforcing First Stop Health’s position as a trusted partner • Lead, coach, and develop a team of 8-10 customer success professionals focused on client growth and retention • Support organizational planning and team evaluation processes, along with recommendations for leadership on infrastructure, tooling, and data required for scaling • Set clear expectations, provide regular feedback, and foster a high-performance, client-centric team culture • Encourage collaboration, accountability, and continuous learning across the team

🎯 Requirements

• 10+ years of experience in leadership roles within sales, customer success, or account management • Experience managing large teams & responsibility for team quotas between $30-$70M in ARR • Demonstrated success in driving revenue growth and improving client retention in a fast-paced environment • Strong business acumen and the ability to use data to inform decisions and strategy • Excellent relationship-building and communication skills; you are a confident presenter and trusted advisor • Collaborative, inspiring leadership style with a passion for client success and team growth • Willingness to travel to support key relationships and leadership initiatives • Experience in broker/employee benefit consultant channels preferred

🏖️ Benefits

• Various health and medical coverage options • Dental and vision coverage • Disability and life coverage • Monthly medical waiver allowance for those who waive medical coverage • Remote-first work environment • Flexible paid time off, including Summer Fridays • Employer match 401k plan • Monthly phone stipend • First Stop Health membership benefit providing virtual care solutions