Sr. Regional Account Manager

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.
• 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.
• 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 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.

Requirements

• 8+ 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.

Nice-to-Haves

• Experience in education, government, or regulated markets.
• Familiarity with Challenger or similar insight-led sales methodologies.
• Background in transportation, logistics, or marketplace platforms.