About our client

At HopSkipDrive, the goal is to create opportunity for all through mobility.

HopSkipDrive is a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. Through its marketplace, the company connects kids, older adults, or anyone needing extra support to highly-vetted caregivers on wheels. Through its software and advisory services, it addresses the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges, HopSkipDrive has facilitated more than 3.3 million rides and operates across over 13 states. The company continues to expand at a rapid pace, having made 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.

Who They Are

HopSkipDrive is a driven, mission-focused team, passionate about transforming transportation through innovation and impact. Rather than just selling a service, the company builds lasting partnerships with school districts and government agencies, solving their toughest challenges with a vetted CareDriver marketplace and cutting-edge solutions.

Within the Revenue team, the mission is clear: drive revenue growth, deliver value to clients, and redefine what’s possible in mobility—while making a meaningful difference for those who need it most. As a Sales Manager, this person will lead the team of Regional Account Managers whose goal is to grow the client base by communicating the HopSkipDrive story, aligning unique value propositions with client needs, creating urgency, and closing deals to bring solutions to life.

To excel in this role, the following key job responsibilities are expected:

• Lead with Empathy & Urgency: Prioritize speed, empathy, humility, and gratitude in the management approach. No deal is the same, and no team member has the exact same strengths—those strengths 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 time to travel with team members (including multi-day trips) for client meetings, follow-ups, and drop-in visits. This business thrives on personal face-to-face interactions.
• Foster Accountability: Expect – and empower – the team to demonstrate extreme ownership over goals, quotas, and team outcomes.
• Grow Market Share & Influence: Reflect on, experiment with, and utilize an evolving suite of strategies and tactics to expand market share and influence within the industry.
• Prioritize Time Management: Maintain consistent organization, efficiency, and focus on what is most important for both individuals and the overall team, enabling the management of multiple projects at once.
• Seek Constant Improvement: Exhibit curiosity and flexibility in sales approaches, strategies, and tactics. Continuous training and refinement are key to staying ahead of the competition and meeting company and client needs.
• Partner Cross-Functionally: Collaborate with teams including Support, Product, Trust & Safety, Legal, and Operations to implement feedback from the team and clients, optimizing offerings accordingly.
• Provide Ongoing Performance Management: Create and evaluate territories, goals, expectations, and priorities for the team. Monitor progress, deliver coaching, adjust strategies, and report outcomes to leadership.
• Be the Voice of the Team: Act as the team leader and liaison to leadership, relaying team feedback, market trends, industry changes, and emerging opportunities.

Who They Are Looking For

The ideal candidate is passionate about scaling and mentoring a world-class sales team to drive growth and deliver impactful solutions to prospective clients. With personal expertise in pitching, negotiation, and closing, this professional is equipped to coach their team to communicate HopSkipDrive’s value proposition and convert leads into active paying clients. Results-driven, this individual thrives in dynamic environments where their contributions have a direct impact on success.

With the qualifications and experience listed below, this individual will make a tangible and immediate impact:

• B2B Strategic Sales Experience: 10+ years as an individual contributor with a proven record of growing a book of business year over year through account management, prospecting, pipeline management, pitching, effective negotiation, and closing within a usage-based sales model.
• People Management: 5+ years of experience leading sales teams of five or more representatives, consistently meeting or exceeding targets through repeatable and scalable processes.
• Growth Mindset: A firm belief in the potential for personal and team growth, along with the initiative to ask tough questions and research new ways to refine strategies.
• Scaling Teams: Demonstrated success in growing sales teams using predictable and measurable methods that support performance assessment and coaching.
• Demonstrated Trust: Ability to build trust, credibility, and collaboration with internal and external stakeholders through clear and effective communication in a remote work setting.
• Startup Mentality: Ability to problem-solve and guide others through change in a fast-paced, high-stakes environment with minimal direction and high visibility, all while remaining adaptable.
• Tech Stack Familiarity: Experience with CRM tools and sales analytics platforms, preferably Salesforce, Seismic, and Outreach, as well as G Suite (Docs, Sheets, Slides).

Our Investment In the Candidate

HopSkipDrive wants each team member to be an owner in the company and share in executing its vision, so every full-time employee has equity. The company offers flexible vacation, medical, dental, vision, and life insurance, 401(k), FSA, and the opportunity to work for a uniquely positioned, VC-backed company in a highly attractive space with substantial upside potential.

HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role in Los Angeles, CA is a $130,000 base with an OTE of $200,000. This position is remote and, as such, compensation will ultimately align with the location where the position is filled. Final compensation will be determined by several factors including 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.

This role will be fully remote in one of the following states: AZ, CA, CO, CT, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OH, OK, OR, SC, TN, TX, UT, VA, WA, WI.