Regional Sales Manager

Our client's mission

At HopSkipDrive, the mission is to create opportunity for all through mobility.HopSkipDrive is a technology company addressing complex transportation challenges in contexts where safety, equity, and care are paramount. Through its marketplace, the company connects kids, older adults, and individuals needing extra support with highly vetted caregivers on wheels. In addition, through software and advisory services, HopSkipDrive tackles major transportation issues faced by schools and school districts nationwide.

Founded by three mothers as a response to their own transportation needs, HopSkipDrive has facilitated more than 3.3 million rides and now operates in over 13 states. The company is expanding rapidly, having earned a place on the Inc. 5000 list four times and on the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100 million in funding to date.

About our client

HopSkipDrive is composed of a driven, mission-focused team passionate about transforming transportation through innovation and impact. Rather than simply offering a service, the company builds long-term partnerships with school districts and government agencies, providing value through a vetted CareDriver marketplace and cutting-edge solutions.

About the role

The Revenue team at HopSkipDrive is focused on driving revenue growth, delivering meaningful client value, and redefining what’s possible in mobility, especially for those who need it most.

As part of this team, the Regional Sales Manager will lead a team of Regional Account Managers, responsible for expanding the client base by sharing the HopSkipDrive story, aligning its unique value propositions with client needs, creating urgency, and closing deals to bring transportation solutions to life.

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

• Lead with Empathy & Urgency: Prioritize speed but also empathy, humility, and gratitude in your management approach. No deal is exactly the same, and no one rep has the same strengths that should be fostered. Managers should always have high integrity and resilience, be adaptable, and motivated to drive progress.
• Prioritize In-Person Team and Client Engagement: Dedicate up to 50% of your time to travel with your team members (including multi-day trips) for client meetings, follow-ups, and drop in meetings. This business and industry thrives on personal face-to-face interactions.
• Foster Accountability: Expect – and empower – your team to demonstrate extreme ownership over their goals, quotas, and outcomes of our team.
• Grow Market Share & Influence: The industry is not static, neither are we. You will constantly reflect on, experiment with, and utilize an evolving suite of strategies and tactics to grow our market share and influence within our industry.
• Prioritize Time Management: Demonstrate ever-present organization, efficiency, and focus on what is most important for individuals and the overall team, empowering you and others to juggle multiple projects at once.
• Seek Constant Improvement: Demonstrate curiosity and malleability in your sales approach, strategies, and tactics. We are constantly training and refining our craft to stay ahead of the competition and support overall company and client needs.
• Partner Cross-Functionally: Collaborate with internal teams including Support, Product, Trust & Safety, Legal, and Operations to relay and ultimately implement team and client feedback, optimizing our offerings to their needs.
• Provide Ongoing Performance Management: Create and evaluate team territories, goals, expectations, and priorities. Measure progress, provide coaching, make adjustments, and supply reporting to leadership.
• Be the Voice of the Team: Serve as the leader of the team and representative to leadership – relaying team feedback, key market trends, changes, and opportunities.

Who You Are

You're passionate about scaling and mentoring a world-class sales team that will drive sales growth, and deliver impactful solutions to prospective clients. With personal expertise in pitching, negotiation, and closing, you can confidently coach your team to 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:

• B2B Strategic Sales Experience: 10 years as an individual contributor with a track record of growing your book of business YoY through account management, prospecting, managing a pipeline, pitching, effective negotiation, and closing within a usage-based sales process.
• People Management: 5 years leading sales teams of 5 sales reps or more to meet or exceed targets through repeatable and scalable methods.
• Growth Mindset: You believe that you and your team can always improve, and you are motivated to ask challenging questions and do the research to identify and continuously refine your approach.
• Scaling Teams: Proven experience scaling a sales team through predictable and repeatable methods that we will allow the organization to measure and coach individuals' performance.
• Demonstrated Trust: Commitment to building trust, credibility, and collaboration with both internal and external audiences through clear and effective communication while working in a remote environment.
• Startup Mentality: The ability to problem-solve and coach through change in a fast-paced, deadline-driven environment with minimal direction and high visibility while remaining flexible to change.
• Tech Stack Familiarity: Experience with CRM tools and sales analytics platforms, preferably Salesforce, Seismic, and Outreach along with the G Suite (Docs, Sheets, Slides).

Their Investment in You

HopSkipDrive believes in shared ownership and is committed to ensuring every full-time employee shares in executing the company’s vision—all full-time team members receive equity. In addition to ownership, the company offers flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and the opportunity to work at a uniquely positioned, VC-backed company operating in a high-growth, high-impact space with significant upside potential.

HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA includes a $130,000 base with an OTE (On-Target Earnings) of $200,000. As the role is remote, compensation will ultimately reflect the location in which the position is filled. Final compensation will be based on factors such as the candidate’s relevant work experience, skill set, certifications, and specific work location. The total compensation package for this position also includes equity stock options.

HopSkipDrive is proud to be an equal opportunity employer. All qualified applicants will receive consideration for employment regardless of race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, veteran status, or any other protected class.