Role Clarification: This remote role requires frequent, in-person meetings. We are therefore only considering candidates in and around the Milwaukee, WI area.

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.  

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

• In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
• Spearhead Enterprise Growth: Drive the success of HopSkipDrive’s rapidly expanding Enterprise business by achieving ambitious revenue growth targets and delivering impactful results.
• Manage Client Accounts: Retain and expand a portfolio of existing clients by delivering exceptional service, actively identifying upsell and cross-sell opportunities, and building a robust pipeline of new prospects.
• Seek Net-New Opportunities: Proactively identify potential leads, pinpoint key stakeholders within client organizations, and leverage existing networks, to uncover additional opportunities to deliver value with key stakeholders across school districts and government departments .
• Communicate Tailored Value: Leverage a consultative approach to identify transportation challenges and opportunities, crafting tailored solutions that align HopSkipDrive’s offerings and value proposition with client needs. 
• 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.
• Lead Pricing Discussions: Drive pricing negotiations and shape strategic approaches to ensure long-term client alignment and growth in your metro.

Who You Are

You’re passionate about building strong client relationships, driving sales growth, and delivering impactful solutions. With expertise in account management, you confidently support school districts, navigate client challenges, and identify opportunities to expand and retain business. You’re motivated by results, and thrive in dynamic environments where your contributions directly drive t success.  

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

• Strategic Sales Expertise: 2+ years of experience in sales, account management or a related role. Strong background in developing and executing comprehensive account plans, identifying upsell and cross-sell opportunities, and delivering solutions that align with client needs and business goals.
• Proven Relationship Building: Demonstrated success in cultivating strong, trust-based, and empathetic relationships with clients and internal stakeholders in an account management or sales based role.
• Cross-Functional Collaboration: Strong experience working effectively in cross-functional teams, collaborating with multiple departments to achieve shared goals and drive business success.
• Critical Thinking and Problem-Solving: Strong ability to identify challenges, analyze data, and develop creative solutions to address client needs, overcome obstacles, and drive sales performance.
• Organizational Skills: Demonstrated ability to manage multiple client accounts, prioritize tasks effectively, and maintain a well-organized pipeline to meet sales targets in a fast-paced environment.  
• 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.
• Advanced Presentation Skills: Proven ability to craft and deliver persuasive, engaging presentations to a range of audiences, including clients, internal teams, and leadership.

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 committed to fair and equitable compensation practices. The salary range for this role is an $85,000 base with an OTE of $125,000 - $130,000. 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.

Reminder: This remote role requires frequent, in-person meetings. Qualified candidates must be based in or within driving distance of Milwaukee, WI.