Regional Account Manager

HopSkipDrive

Regional Account Manager responsible for account management and growth strategies at HopSkipDrive. Focusing on retention and expansion within educational and governmental sectors.

Posted 6/18/2026full-timeIllinois, Minnesota, Missouri, Pennsylvania, Wisconsin • 🇺🇸 United StatesMid-LevelSenior💰 $85,000 - $90,000 per yearWebsite

Tech Stack

Tools & technologies

SFDC

About the role

Key responsibilities & impact

Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement.
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 while owning retention, expansion, and overall performance of named accounts.
Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
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 and optimize our offerings to their needs.
Lead renewals and expansions, including structured negotiations and closing motions.
Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Requirements

What you’ll need

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.

Benefits

Comp & perks

equity
flexible vacation
medical insurance
dental insurance
vision insurance
life insurance
401(k)
FSA
opportunity to work for a uniquely positioned, VC-backed company

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

Account ManagementCustomer SuccessConsultative SalesRetention RevenueExpansion RevenueCRM DisciplineData FluencyChallenger MethodologyCross-Functional Account ExecutionAI Integration

Soft Skills

Executive CommunicationPresentation SkillsRelationship BuildingInfluencing Decision-MakingOperational RigorComfort in AmbiguityAccountability for OutcomesNegotiation SkillsClient EngagementStrategic Thinking