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.
• Own retention, expansion, and overall performance of named accounts.
• Deliver exceptional client service and build/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.
• Lead renewals and expansions, including structured negotiations and closing motions.
• Collaborate cross-functionally with Metro Service Managers to drive operational excellence.
• Identify product-level gaps and strategies for product penetration by account.
• Provide recommendations to senior staff for required resources.

Requirements

• 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.
• Must be based in the Great Lakes Region (PA, MI, IL, WI).
• Reliable transportation and ability to travel 2-3 days per week for on-site client visits.

Preferred

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

Compensation

• Base salary: $85,000 - $90,000
• On-Target Earnings (OTE): $130,000 - $140,000
• Equity stock options
• Flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA