Strategic Account Executive

About the Company

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation, connecting kids to highly-vetted caregivers through our marketplace and software solutions for schools and districts.

Responsibilities

• Negotiate terms and close new business, converting contracts into paying clients
• Source 20-30% of own pipeline through proactive prospecting and multithreading
• Lead conversations with insights to challenge the status quo and create urgency
• Build relationships across multiple stakeholders including transportation directors, finance, and executive leadership
• Apply MEDDPICC qualification rigor to all deals and maintain forecast accuracy
• Collaborate cross-functionally with Support, Product, and Operations teams
• Travel up to 50% of the time for in-person meetings and field prospecting
• Maintain meticulous Salesforce discipline and documentation
• Leverage AI tools like Gong, Salesforce Agentforce, and Claude to accelerate productivity

Requirements

• 8+ years of B2B sales experience, including 2+ years in enterprise sales or account management
• 5+ years of prospecting experience via phone or field techniques (cold calling, door knocking)
• Proven track record of negotiating B2B contracts and navigating RFP processes
• Experience communicating with C-suite and government stakeholders (Superintendents, Directors)
• Challenger sales mentality with the ability to lead with insight
• Ability to travel up to 50% (including overnight) for field sales
• Proficiency in leveraging AI-based sales tools

Preferred Qualifications

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