Regional Account Manager

1 week, 5 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

  • Manage day-to-day account relationships and long-term strategy for a Tier 2 book of business.
  • Own retention, expansion, and overall account health for named accounts.
  • Act as the strategic quarterback for complex districts and coordinate internal and external stakeholders.
  • Conduct 2-3 days of in-person client visits each week, with additional travel as needed.
  • Lead district-level growth planning using structured discovery and Challenger methodology.
  • Build multi-threaded relationships across operational, technical, and executive stakeholders.
  • Identify unmet needs, quantify opportunity, and surface net-new expansion opportunities.
  • Communicate tailored value and outcome-based recommendations to client executives.
  • Partner with Sales, Operations, Product, Finance, Trust & Safety, and Support to align on client priorities.
  • Lead renewals, pricing discussions, negotiations, and closing motions.

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, such as Salesforce or an equivalent system.
  • Experience leading cross-functional account execution.
  • Comfort operating in ambiguity with accountability for outcomes.
  • 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.
  • Must be based in the Great Lakes Region, including PA, MI, IL, or WI.
  • Reliable transportation is required for regular on-site client visits and travel.

Benefits

  • Full-time equity so employees can own a share of the company.
  • Flexible vacation policy.
  • Medical, dental, vision, and life insurance.
  • 401(k) retirement plan.
  • FSA benefit.
  • Remote work arrangement.
  • Base salary of $85,000-$90,000 with OTE of $130,000-$140,000.
  • Total compensation includes equity stock options.

Interested in this position?

Apply directly on the company website

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