Regional Account Manager- Future Opportunity

The role

The Regional Account Manager manages day-to-day account management and long-term strategy for a Tier 2 book of business. This role focuses on driving retention, expansion, and account health through strategic planning and cross-functional collaboration.

What you will do

• Dedicate 2-3 days each week to on-site client visits
• Drive strategic expansion across product suite through structured discovery and Challenger methodology
• Build and execute district-level growth strategies
• Own retention, expansion, and overall performance of named accounts
• Deliver client service and maintain multi-threaded relationships
• Lead multi-department discovery within districts to uncover unmet needs
• Communicate with client executives using data and insight
• Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities
• Lead renewals and expansions including structured negotiations and closing motions
• Utilize AI to craft meeting agendas, synthesize needs, and draft communications

Required qualifications

• 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
• Reliable transportation

Benefits

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

About the company

HopSkipDrive is a Series D company that provides supplemental student transportation through a marketplace connecting kids to vetted caregivers. The company uses AI to solve transportation challenges for schools and school districts.