Director, Customer Success

Summary

Join HopSkipDrive, a technology company focused on safe and equitable transportation solutions, as a remote Customer Success leader. You will build, scale, and lead a high-performing team, managing complex enterprise-level clients, primarily school districts and government agencies. Leverage your extensive experience in strategic client management, retention, and data-driven decision-making to drive successful outcomes. Demonstrate expertise in onboarding, implementation, cross-functional collaboration, and process improvement. This role requires strong communication and advocacy skills to effectively represent client needs. HopSkipDrive offers competitive compensation, equity, flexible vacation, comprehensive benefits, and the opportunity to work for a rapidly growing, VC-backed company.

Requirements

• Minimum of 5+ years experience building, scaling, and leading high-performing Customer Success or strategic Account Management teams, preferably in a B2B environment focused on complex clients
• Extensive experience (e.g., 10+ years) managing relationships and driving successful outcomes for complex, strategic enterprise-level clients; experience specifically with school districts or government agencies, fleet management and logistics is highly desirable
• Proven track record of developing and implementing successful regional or portfolio-wide strategies to proactively monitor client health, improve retention rates, and foster long-term loyalty
• Strong analytical skills and a data-driven mindset, with experience using key customer success metrics and client data to derive actionable insights, measure performance, and inform strategic planning
• Demonstrated success in designing, overseeing, or significantly improving client onboarding and implementation programs, ensuring successful adoption of complex solutions or services
• Proven ability to partner effectively with senior leaders across different functions (e.g., Sales, Operations, General Management) to align strategies, support growth initiatives, and ensure a cohesive client experience
• Experience in identifying inefficiencies and driving continuous improvement within customer success workflows, processes, and tools to enhance team performance and client outcomes
• Excellent communication and influencing skills, with the ability to synthesize diverse client feedback, effectively advocate for customer needs internally, and contribute to product/service strategy

Responsibilities

• Build, scale, and lead a high-performing Customer Success or strategic Account Management team
• Manage relationships and drive successful outcomes for complex, strategic enterprise-level clients
• Develop and implement successful regional or portfolio-wide strategies to proactively monitor client health, improve retention rates, and foster long-term loyalty
• Use key customer success metrics and client data to derive actionable insights, measure performance, and inform strategic planning
• Design, oversee, or significantly improve client onboarding and implementation programs
• Partner effectively with senior leaders across different functions (e.g., Sales, Operations, General Management) to align strategies, support growth initiatives, and ensure a cohesive client experience
• Identify inefficiencies and drive continuous improvement within customer success workflows, processes, and tools to enhance team performance and client outcomes
• Synthesize diverse client feedback, effectively advocate for customer needs internally, and contribute to product/service strategy

Preferred Qualifications

Experience specifically with school districts or government agencies, fleet management and logistics

Benefits

• Flexible vacation
• Medical, dental, vision, and life insurance
• 401(k)
• FSA
• Equity stock options