Strategic Account Executive

Who We Are

We are a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, we build lasting partnerships with school districts and government agencies, solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.

As a Revenue team, our goal is clear: drive revenue growth, deliver value to our clients, and redefine what’s possible in mobility—while making a meaningful difference for those who need it most. 

As Strategic Account Executives, we provide this value to net-new prospective business partners in particular by telling the HopSkipDrive story, connecting our unique value propositions to their needs, creating urgency, and closing the deal to bring the solutions to reality. We achieve this by challenging the status quo and pushing our prospects to innovate alongside us.

To excel in this role, you will be expected to take ownership of and demonstrate the following key job responsibilities:

• Always be Closing: Effectively negotiate terms, and execute by closing new business. After the initial contract is executed, convert to a paying client, and grow that account during the initial onboarding period.
• Always Build Pipeline: You will be supported by a worldclass SDR team but best performing AEs source around 20-30% of their own pipeline plus multithread all the time.
• Challenge the Status Quo: Lead every conversation with an insight, not a pitch. Whether in person, by phone, or on video — Teach the prospect something they haven’t considered, Tailor the message to their specific situation and role, and Take Control of the process to create urgency and drive the deal forward. 
• Demonstrate Curiosity and Compassion: Ask targeted questions and listen to understand unspoken concerns, political dynamics, and the real decision-making structure across the buying committee. Use those insights to execute, teaching each stakeholder a new perspective on their problem, tailoring the message to their priorities, and taking control of the process to build consensus and create urgency toward a decision.
• Multi-Threaded Stakeholder Engagement: Build and maintain relationships across multiple stakeholders in the buying committee simultaneously — including transportation directors, operations leads, finance, and executive leadership — mapping the full decision-making structure, identifying the economic buyer, and driving organizational alignment toward close. 
• Pipeline Qualification Discipline: Apply MEDDPICC qualification rigor to every deal. Prioritize finding the true economic buyer, the individual with real budget authority, early in the cycle, not at the finish line. Develop internal champions who will advocate for HopSkipDrive when you’re not in the room. Maintain forecast accuracy by consistently assessing all MEDDPICC elements on every active opportunity.
• Partner Cross-Functionally: Collaborate with internal teams including Support, Product, Trust & Safety, and Operations to implement client feedback and optimize our offerings to their needs.
• In-Person Prospect Engagement: Dedicate up to 50% of your time to travel within your assigned territory (including overnight) for invaluable face to face meetings, follow ups, unscheduled cold door knocking at dis