Strategic Account Executive

Responsibilities

• Close new business by negotiating terms, executing contracts, converting to paying clients, and growing accounts during onboarding
• Source 20-30% of pipeline independently while multi-threading opportunities
• Lead conversations with insights rather than pitches; teach prospects new perspectives, tailor messaging, and create urgency
• Ask targeted questions to understand concerns, political dynamics, and decision-making structures across buying committees
• Build and maintain relationships across multiple stakeholders including transportation directors, operations leads, finance, and executive leadership
• Apply MEDDPICC qualification rigor to every deal; identify economic buyers early and develop internal champions
• Collaborate cross-functionally with Support, Product, Trust & Safety, and Operations teams
• Dedicate up to 50% of time to travel within assigned territory for in-person meetings, cold door knocking, and prospecting
• Maintain meticulous Salesforce discipline documenting all interactions, pipeline stages, and MEDDPICC criteria
• Build and execute territory plans prioritizing accounts by opportunity size, strategic fit, and probability
• Leverage AI tools including Gong, Salesforce Agentforce, and Claude for prospect research, call preparation, and deal risk analysis

Requirements

• 8+ years of B2B sales experience including 2+ years in enterprise sales, account management, or related role
• 5+ years prospecting by phone or in the field including cold calling and cold door knocking
• Experience negotiating B2B contracts with multiple stakeholders and navigating RFPs
• Proven experience communicating with Superintendents, Directors, and C-suite stakeholders
• Challenger sales experience and mentality; leads with insight and takes control of the sales process
• Comfortable traveling up to 50% (including overnight) for field sales activities
• Track record of consistently exceeding targets and achieving measurable results

Nice-to-Haves

• Experience selling into K-12 school districts, government agencies, or public sector organizations