Strategic Account Executive

HopSkipDrive•Chicago, IL

14d•Remote

About The Position

At HopSkipDrive , our goal is to create opportunity for all through mobility. We’re a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through our marketplace, we connect kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts around 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 17 states around the country. We continue to expand at a rapid pace, making the Inc. 5000 list four times, as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date. 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.

Requirements

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.

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.