Strategic Account Executive
Strategic Account Executive responsible for closing new business with school districts and government agencies, managing enterprise sales cycles, and traveling up to 50% for in-person prospecting and meetings.
About the job
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
Skills
Salesforce, MEDDPICC, B2B Sales, Enterprise Sales, Challenger Sales, Rfp Management, Pipeline Management, Territory Planning, Gong, Claude
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