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First Stop Health

First Stop Health

via Remote Rocketship

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Senior Director – Customer Success

Anywhere
full-time
Posted 10/6/2025
Verified Source
Key Skills:
Leadership
Sales Management
Customer Success
Account Management
Revenue Growth
Client Retention
Data-Driven Strategy
Executive Relationship Management

Compensation

Salary Range

$150K - 250K a year

Responsibilities

Lead and execute renewal and growth strategies for a $45M+ business, manage and develop a team of 8-10 customer success professionals, and build systems to proactively manage client health and retention.

Requirements

10+ years in leadership roles within sales, customer success, or account management managing large teams and quotas, strong business acumen, excellent communication skills, and willingness to travel.

Full Description

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

This job posting was last updated on 10/8/2025

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