Regional Director, Customer Success

At HopSkipDrive, our goal is to create opportunity for all through mobility. 

We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around the country. 

Founded by three moms as a solution to their own transportation challenges, we’ve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

* This role will be fully remote in one of the following states AZ, CA, NV, OR, WA*

Who We Are: 

You’re passionate about developing strong relationships with clients and building and scaling a high performing distributed team. With the following skills, you’ll make a tangible and immediate impact:

• Leadership Experience: 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.
• Strategic Client Management: 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.
• Retention & Loyalty Expertise: 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.
• Data-Driven Decision Making: 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.
• Onboarding & Implementation Oversight: Demonstrated success in designing, overseeing, or significantly improving client onboarding and implementation programs, ensuring successful adoption of complex solutions or services.
• Cross-Functional Collaboration: 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.
• Process Improvement & Operational Rigor: Experience in identifying inefficiencies and driving continuous improvement within customer success workflows, processes, and tools to enhance team performance and client outcomes.
• Communication & Advocacy: 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.

Our Investment In You

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. The salary range for this role in Los Angeles, CA is 135,000-150,000 per year. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal-opportunity employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.