Senior Regional Account Manager

About the Company

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers through our marketplace and software.

Responsibilities

• Dedicate 2-3 days each week to on-site client visits to foster relationships and drive engagement
• Drive strategic expansion across the product suite using Challenger methodology
• Manage retention, expansion, and overall performance of a Tier 1 book of business
• Build and maintain multi-threaded relationships across operational, technical, and executive stakeholders
• Lead pricing discussions, renewals, and structured negotiations
• Partner cross-functionally with Sales, Operations, Product, Finance, and Trust & Safety
• Utilize AI tools to automate reporting, synthesize stakeholder needs, and craft communications

Requirements

• 8+ 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
• Strong executive communication and presentation skills
• Advanced CRM discipline and data fluency (Salesforce)
• Ability to travel regionally for 2-3 days of on-site client visits per week

Preferred Qualifications

• Experience in education, government, or regulated markets
• Familiarity with Challenger or similar insight-led sales methodologies
• Background in transportation, logistics, or marketplace platforms
• High operational rigor and ability to leverage AI into daily workflows

Benefits

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