Strategic Account Executive

HopSkipDrive

8h•Remote

About The Position

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across the country. Founded by three moms as a solution to their own transportation challenges, we've now facilitated more than five million rides across over over 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date. We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. 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.

Requirements

8+ years of B2B sales experience, including 2+ years in enterprise sales, account management, or a related role.
Strong background in developing and executing comprehensive tactics to get in the door, pitch the solution, negotiate, and then close.
Experience selling into K-12 school districts, government agencies, or public sector organizations is a plus.
Track record of consistently exceeding targets and achieving measurable results, with a sharp focus on delivering outcomes that align with company objectives.
5+ years prospecting by phone or in the field including cold dropping in, cold calling, and other common prospecting techniques.
Experience negotiating B2B contracts with multiple stakeholders and implementing tactics both internally and externally to bring the deal to a close including experience navigating strategy for RFPs before and after the proposal.
Proven experience communicating with Superintendents, Directors, and C-suite stakeholders (or similar titles) with authority and precision. Adapts messaging to executive audiences — translating operational detail into the business and mission outcomes they care about — and leads high-level presentations that influence client strategy and drive significant outcomes.
Proven Challenger sales experience and mentality. Leads with insight, tailors the message to each persona, and takes control of the sales process to constructively challenge buyer assumptions and create urgency. Naturally reframes problems rather than validating them.
Comfortable traveling up to 50% (including overnight), practiced in cold door knocking, and disciplined enough to manage a high-volume field schedule and keep momentum across the territory.
Proven experience leveraging AI-based or AI-enhanced sales tools to optimize the sales cycle (e.g., automated meeting recaps, prospecting research, and pipeline management)

Responsibilities

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.
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.
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.
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.
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.
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.
Collaborate with internal teams including Support, Product, Trust & Safety, and Operations to implement client feedback and optimize our offerings to their needs.
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 district offices and transportation facilities, and cold prospecting with prospects within your assigned region or territory.
Maintain meticulous Salesforce discipline as a foundational element of your sales strategy. Ensure all interactions, pipeline stages, and MEDDPICC criteria are consistently documented.
Build and execute a territory plan that prioritizes accounts by opportunity size, strategic fit, and probability. Know your whitespace, manage coverage proactively, and consistently generate the pipeline needed to hit your number.
Use AI-powered tools — including Gong, Salesforce Agentforce, Claude and others to research prospects, prepare for calls, surface deal risk signals, and accelerate your productivity. We expect our AEs to be active and creative users of available AI, not passive ones.