Regional Account Manager

3 weeks, 3 days ago
Full-time
Senior
Customer and Technical Support
HopSkipDrive

HopSkipDrive

HopSkipDrive provides safe and innovative youth transportation solutions, simplifying logistics for schools and families while prioritizing safety and efficiency.

Road & Rail
251-1K
Founded 2015
$124M raised

Description

  • Own day-to-day account management and long-term account strategy for a Tier 2 book of business.
  • Drive retention, expansion, and overall account performance for named accounts.
  • Serve as the strategic lead for complex districts and coordinate internal and external stakeholders.
  • Conduct in-person client visits 2-3 days per week and manage additional national travel as needed.
  • Build district-level growth strategies using structured discovery and Challenger methodology.
  • Develop and maintain multi-threaded relationships across operational, technical, and executive stakeholders.
  • Lead renewals, pricing discussions, and expansion negotiations to close business.
  • Partner with Sales, Operations, Product, Finance, Trust & Safety, and Support to align on client priorities.
  • Identify product-level gaps and recommend strategies to increase product penetration by account.
  • Use AI and Salesforce data to create meeting agendas, follow-ups, account summaries, reports, and growth recommendations.

Requirements

  • 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, preferably with Salesforce or an equivalent system.
  • Experience leading cross-functional account execution.
  • Comfort operating in ambiguity with accountability for outcomes.
  • High operational rigor and the ability to leverage AI in daily workflows.
  • Experience in education, government, or regulated markets is preferred.
  • Familiarity with Challenger or similar insight-led sales methodologies is preferred.
  • Background in transportation, logistics, or marketplace platforms is preferred.
  • Candidates must be based in WI, MN, VA, MI, or PA and be willing to travel for regular on-site client visits.

Benefits

  • $85,000-$90,000 base salary with $130,000-$140,000 OTE.
  • Equity and stock options in the company.
  • Flexible vacation policy.
  • Medical, dental, vision, and life insurance.
  • 401(k) retirement plan.
  • FSA benefits.
  • Remote work arrangement with required travel for client visits.
  • Opportunity to join a VC-backed company with significant upside potential.

Interested in this position?

Apply directly on the company website

Apply Now

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