Sr. Regional Account Manager

The role

The Sr. Regional Account Manager manages day-to-day account management and long-term strategy for a Tier 1 book of business. This role owns retention, expansion, and account health for complex districts.

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
• Deliver exceptional 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 stakeholder needs, and draft communications
• Leverage AI to generate automated summaries of Salesforce data and build recurring account reports

Required qualifications

• 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
• Reliable transportation

Nice to have

• 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 the ability to leverage AI into daily workflows

Benefits

• equity
• flexible vacation
• medical
• dental
• vision
• life insurance
• 401(k)
• FSA

About the company

HopSkipDrive is a Series D company that connects kids to highly-vetted caregivers on wheels through a marketplace and software. Their mission is to create opportunity for all through mobility.