HopSkipDrive

HopSkipDrive

Sr. Regional Account Manager

Remote USA · Senior · Full-time

Sponsorship not specified$90k-$100kDetected 22 days ago
SalesforceCRMAccount ManagementExcelLogisticsCustomer SuccessCommunication

About the role

  • We're the leader in safe, fast, and simple supplemental student transportation.
  • Through our marketplace, we connect kids to highly-vetted caregivers on wheels.
  • Through our software, we solve the biggest transportation challenges facing schools and school districts across the country.

Responsibilities

  • Spearhead Enterprise Growth: 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.
  • Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
  • Seek Net-New Opportunities: 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.
  • Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
  • Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions.
  • 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.
  • drive revenue growth, deliver value to our clients, and redefine what's possible in mobility-while making a meaningful difference for those who need it most.
  • RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.

Requirements

  • 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.
  • 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

Nice to have

  • Familiarity with Challenger or similar insight-led sales methodologies highly preferred
  • Background in transportation, logistics, or marketplace platforms highly preferred

Skills

  • About HopSkipDrive
  • 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list.
  • HopSkipDrive is a Series D company and has raised $100M to date.

Compensation

  • The salary range for this role is an $90,000-100,000 base with an OTE of $150,000 - $170,000.

Benefits

  • This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts.
  • We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity.
  • The total compensation package for this role also includes equity stock options.
  • Experience in education, government, or regulated markets highly preferred

Company info

  • We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.
  • As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what's possible in mobility-while making a meaningful difference for those who need it most.
  • The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.
  • This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.
  • We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact.
  • Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.
  • Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business.
  • This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution.
  • Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.
  • To excel in this role, you will be expected to take ownership of and demonstrate the following key job
  • To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:
  • In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
  • Spearhead Enterprise Growth: 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.
  • Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
  • AI Enabled Operational Excellence: 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.
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