Strategic Account Executive

3 months ago
Full-time
Lead
Sales and Business Development
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

  • 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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