Strategic Account Executive

About HopSkipDrive

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 20states. 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.

How we work

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.

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 district offices and transportation facilities, and cold prospecting with prospects within your assigned region or territory. 
• Operational Excellence & CRM Discipline: Maintain meticulous Salesforce discipline as a foundational element of your sales strategy. Ensure all interactions, pipeline stages, and MEDDPICC criteria are consistently documented.
• Manage Your Territory: 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.
• Leverage AI Tools: 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.

Who You Are
You excel at establishing new relationships, driving sales growth, and delivering impactful solutions to prospective clients. With expertise in pitching, negotiation, and closing, you can confidently sell the value propositions of HopSkipDrive to prospective clients and convert them into active paying clients. You’re motivated by results, and thrive in dynamic environments where our contributions directly drive to success.

With the required qualifications and necessary experience listed below, your impact will be tangible and immediate:

• Strategic Sales Expertise: 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. 
• Goal-Driven Focus: Track record of consistently exceeding targets and achieving measurable results, with a sharp focus on delivering outcomes that align with company objectives.
• Hunting and Prospecting: 5+ years prospecting by phone or in the field including cold dropping in, cold calling, and other common prospecting techniques.
• Negotiation and Closing: 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.
• Executive-Level Communication: 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.
• Challenger Mentality: 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.
• Professional Field Sales Skills: 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.
• AI Fluency & Tool Track Record: 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)

Our Investment In You

We want you to be an owner in our company and share in executing our vision, so every full-time employee has equity. In addition, we offer flexible vacation, medical, dental, vision and life insurance, 401(k), FSA, and an opportunity to work for a uniquely positioned, VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is also proud to operate as a drug-free workplace. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is $95,000 base with an OTE of $160,000. This position is remote and, as such, compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal-opportunity employer.  All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.

Role Clarification: This remote role requires frequent travel and in-person meetings.