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

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