Regional Director, Customer Success

Summary

Join HopSkipDrive, a technology company focused on safe and equitable transportation solutions, as a Customer Success Manager. You will be responsible for building and scaling a high-performing team, managing relationships with complex clients, and driving successful outcomes. This role requires extensive experience in customer success, strategic account management, and client retention. You will also need strong analytical skills, experience with onboarding and implementation programs, and the ability to collaborate effectively with cross-functional teams. HopSkipDrive offers competitive compensation, equity, flexible vacation, comprehensive benefits, and the opportunity to work for a VC-backed company with significant growth potential.

Requirements

• You’re passionate about developing strong relationships with clients and building and scaling a high performing distributed team
• 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 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

Benefits

• We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity
• In addition, we offer flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential
• HopSkipDrive is committed to fair and equitable compensation practices