Strategic Account Executive

Role Clarification: This remote role requires frequent and in-person meetings, predominantly in the MidWest service metros. We are therefore only considering candidates located in Chicago, IL MidWest Region.

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.

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

• Communicate Tailored Value: Seek to identify and understand the transportation challenges and opportunities of net-new prospects, ultimately tailoring proposals that align HopSkipDrive’s offerings and value proposition with client needs.
• Always be Closing: Regularly build the pipeline, negotiate terms, and execute by closing new business.
• Practice Adaptable Selling: Demonstrate value and earn business through a variety of sales formats including email correspondence, in person, via video call, or phone while using tools like slide decks, demos, and marketing collateral.
• Demonstrate Curiosity and Compassion: Ask questions and actively listen to understand our prospective clients goals, motivations, and abilities as well as to determine key stakeholders essential to closing the deal.
• 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, and cold prospecting with prospects within the California and Washington.
• Cross-Functional Collaboration: Strong experience working effectively in cross-functional teams, collaborating with multiple departments to achieve shared goals and drive business success.

Who You Are
You're passionate about 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: 5+ years of experience in B2B 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.
• 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: 3+ years prospecting by phone or in the field including cold dropping in, cold calling, and other common prospecting techniques.
• Objection Handling: Proven ability to listen, understand, and redirect prospects to the solution we are offering. Comfortable disagreeing with a prospects point of view and walking them through why they should shift.
• Negotiation and Closing: Experience negotiating B2B contracts with multiple stakeholders and implementing tactics both internally and externally to bring the deal to a close.
• Advanced Presentation Skills: Proven ability to craft and deliver persuasive, engaging presentations to a range of audiences, including decision makers, influencers, and executive leadership.
• Professional Field Sales Skills: Experience traveling up to 50% of the time (including overnight), staying organized, dropping in on prospects, presenting or making conversation to move the deal forward.

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 in Los Angeles, CA 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 and in-person meetings, predominantly in the Midwest service metros. We are therefore only considering candidates located in Chicago, IL MidWest Region.