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Strategic Account Executive

3 weeks, 3 days ago
United States
Full-time
Lead
Account Executive
Sales and Business Development
Salesforce
Apply Now
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
View All Jobs 8

Description

  • Close new business by negotiating terms, executing contracts, and converting signed accounts into paying clients during onboarding.
  • Source and build pipeline, including generating 20-30% of pipeline independently while multi-threading prospects throughout the sales cycle.
  • Lead sales conversations with insight, tailor messaging to each stakeholder, and create urgency to move deals forward.
  • Ask targeted questions, uncover decision-making dynamics, and build consensus across buying committees.
  • Build and maintain relationships with multiple stakeholders, including transportation, operations, finance, and executive leaders.
  • Apply MEDDPICC qualification rigor to evaluate opportunities, identify the economic buyer, and improve forecast accuracy.
  • Partner cross-functionally with Support, Product, Trust & Safety, and Operations to incorporate client feedback and improve offerings.
  • Travel up to 50% of the time, including overnight, for in-person meetings, follow-ups, cold door knocking, and prospecting within the territory.
  • Maintain strong Salesforce discipline by documenting interactions, pipeline stages, and qualification criteria.
  • Build and execute a territory plan that prioritizes accounts by opportunity size, strategic fit, and likelihood to close.
  • Use AI-powered tools such as Gong, Salesforce Agentforce, and Claude to research prospects, prepare for calls, and surface deal risks.

Requirements

  • 8+ years of B2B sales experience, including 2+ years in enterprise sales, account management, or a related role.
  • 5+ years of prospecting by phone or in the field, including cold calling and cold dropping in.
  • Experience selling into K-12 school districts, government agencies, or public sector organizations is a plus.
  • Experience negotiating B2B contracts with multiple stakeholders and navigating RFP strategy.
  • Proven experience presenting to Superintendents, Directors, C-suite stakeholders, or similar executive audiences.
  • Proven Challenger sales experience and a mindset that leads with insight and creates urgency.
  • Comfortable traveling up to 50%, including overnight travel and frequent in-person meetings.
  • Experience using AI-based or AI-enhanced sales tools for meeting recaps, prospect research, or pipeline management.
  • Track record of consistently exceeding targets and delivering measurable results.
  • Remote role with compensation aligned to the location where the position is filled.

Benefits

  • $95,000 base salary with $160,000 OTE.
  • Equity stock options, with full-time employees receiving company equity.
  • Flexible vacation.
  • Medical, dental, vision, and life insurance.
  • 401(k) and FSA.
  • Remote work arrangement.
  • Opportunity to work for a VC-backed company with significant upside potential.

Interested in this position?

Apply directly on the company website

Apply Now

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