Note: The job is a remote job and is open to candidates in USA. HopSkipDrive is a leader in safe, fast, and simple supplemental student transportation. The Regional Account Manager is responsible for day-to-day account management and long-term account strategy, focusing on retention, expansion, and overall account health while collaborating cross-functionally to drive operational excellence.

Responsibilities

• Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required
• Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts
• Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders
• Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology
• Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations
• Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs
• Lead renewals and expansions, including structured negotiations and closing motions
• Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships

Skills

• 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments
• Proven ownership of retention and expansion revenue
• Strong executive communication and presentation skills
• Demonstrated success managing complex, multi-stakeholder accounts
• Advanced CRM discipline and data fluency (Salesforce or equivalent)
• Experience leading cross-functional account execution
• Comfort operating in ambiguity with accountability for outcomes
• High operational rigor and the ability to leverage AI into daily workflows
• Experience in education, government, or regulated markets
• Familiarity with Challenger or similar insight-led sales methodologies
• Background in transportation, logistics, or marketplace platforms

Benefits

• Equity
• Flexible vacation
• Medical
• Dental
• Vision
• Life insurance
• 401(k)
• FSA
• Equity stock options

Company Overview