Regional Account Manager

Responsibilities

• Manage day-to-day account management and long-term strategy for a Tier 2 book of business
• Drive retention, expansion, and overall account health
• Conduct 2-3 days of in-person client visits each week to foster relationships
• Spearhead enterprise growth using Challenger methodology and structured discovery
• Lead renewals, expansions, and structured pricing negotiations
• Partner cross-functionally with Sales, Operations, Product, Finance, and Support teams
• Utilize AI tools to automate reporting, synthesize stakeholder needs, and draft communications

Requirements

• 5+ years of experience in Account Management, Customer Success, or Consultative Sales
• Experience in SaaS, marketplace, logistics, or services environments
• Proven track record of owning retention and expansion revenue
• Advanced CRM discipline and data fluency (Salesforce)
• Experience in education, government, or regulated markets
• Familiarity with Challenger or similar insight-led sales methodologies
• Background in transportation, logistics, or marketplace platforms
• Ability to travel regionally for 2-3 days of on-site client visits per week

Benefits

• Equity stock options
• Flexible vacation
• Medical, dental, vision, and life insurance
• 401(k) and FSA

About the Company

HopSkipDrive is a mission-driven, AI-forward company that provides safe, fast, and simple supplemental student transportation. We connect kids to highly-vetted caregivers through our marketplace and software solutions for schools and districts.