First Stop Health

Senior Director – Customer Success

First Stop Health

full-time

Posted on:

Location Type: Remote

Location: Remote • 🇺🇸 United States

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Salary

💰 $45,000 per year

Job Level

Senior

About the role

  • 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

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
data-driven decision makingrevenue growthclient retentionquota managementteam leadershiprisk managementclient health metricsupsellingaccount managementcustomer success
Soft skills
relationship buildingcommunicationcollaborative leadershipteam developmentclient-centric culturecoachingfeedback provisionaccountabilityinspirationcontinuous learning
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