Senior Director of Customer Success

Description

Job Title: Senior Director of Customer Success

About Us

On a mission to deliver affordable, delightful healthcare for all, First Stop Health provides connected, whole-person virtual care to employers 24/7 through app, website, or phone in all 50 states. First Stop Health prioritizes an engaging and easy-to-use experience, setting people on healthier journeys through care at multiple stages.

First Stop Health offers a comprehensive benefits package that includes various health and medical coverage options, dental and vision coverage, disability and life coverage, making healthcare easily accessible. For those that choose to waive medical coverage a monthly medical waiver allowance will be provided.

First Stop Health offers a remote-first work environment and flexible paid time off, including Summer Fridays. Furthermore, the employer match 401k plan and monthly phone stipend demonstrate the company's commitment to employee financial well-being. The First Stop Health membership benefit is another added perk for employees and provides our virtual care solutions - Urgent Care, Mental Health, and Primary Care - from their very first day!

Job Description

At First Stop Health we believe that strong, lasting relationships are at the heart of everything we do — with our clients, our partners, and each other. We are looking for a Senior Director of Customer Success who shares that belief and is excited to lead a high-performing, mission-driven team.

In this key leadership role, you will be responsible for driving revenue growth across our existing client base while supporting client retention strategies. You will lead with purpose, empower your team, and collaborate across departments to deliver measurable results and exceptional client experiences. If you are a results-oriented leader who thrives in a fast-paced, relationship-focused environment, we would love to meet you.

Key Responsibilities

Revenue Growth & Retention

• 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
  
  

Team Leadership & Development

• 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
  
  

First Stop Health is committed to diversity, equity, inclusion, and belonging. Research shows that women, people of color and other historically underrepresented groups tend to only apply to jobs in which they meet all of the job requirements. Unsure if you check every box? Apply. We’d love to consider your unique experiences and how you could make First Stop Health even better.

To learn more about First Stop Health, visit https://www.firststophealth.com/ and if you require any assistance during the application process or have questions, please don't hesitate to contact our talent acquisition team via email at [email protected].