Regional Account Manager

About HopSkipDrive

At HopSkipDrive, our mission is to create opportunity for all through mobility. We're the leader in safe, fast, and simple supplemental student transportation. Through our marketplace, we connect kids to highly-vetted caregivers on wheels. Through our software, we solve the biggest transportation challenges facing schools and school districts across 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 20 states. We continue to grow rapidly — earning a spot on the Inc. 5000 list numerous times and the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M to date.

The Role

• 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 strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology. Build and execute district-level growth strategies, including multi-threaded stakeholder plans while owning retention, expansion, and overall performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrive’s product suite through structured discovery and Challenger methodology.
• Communicate Tailored Value: Communicate confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions.

Who You Are

• Required:
• - 5+ years of experience in Account Management, Customer Success, or Consultative Sales in SaaS, marketplace, logistics, or services environments.
• - Proven ownership of retention and expansion revenue.
• - Strong executive communication and presentation skills.
• - Demonstrated success managing complex, multi-stakeholder accounts.
• - Advanced CRM discipline and data fluency (Salesforce or equivalent).
• - Experience leading cross-functional account execution.
• - Comfort operating in ambiguity with accountability for outcomes.
• Preferred:
• - Experience in education, government, or regulated markets.
• - Familiarity with Challenger or similar insight-led sales methodologies.
• - Background in transportation, logistics, or marketplace platforms.

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.
• 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 $85,000-90,000 base with an OTE of $130,000 - $140,000. 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.

Qualifications

• Required:
• - Bachelor's degree or equivalent experience.
• - Proven track record of success in Account Management, Customer Success, or Consultative Sales roles.
• - Strong interpersonal and communication skills.
• - Ability to manage multiple projects and prioritize tasks effectively.
• - Experience working with Salesforce or similar CRM systems.
• - Ability to travel as needed.

Skills

• Required:
• - Excellent client relationship management skills.
• - Strong negotiation and problem-solving abilities.
• - Ability to work independently and as part of a team.
• - Proficiency in Microsoft Office Suite.
• - Strong analytical and data-driven skills.
• - Ability to communicate effectively with executive-level stakeholders.
• Preferred:
• - Experience in education, government, or regulated markets.
• - Familiarity with Challenger or similar insight-led sales methodologies.
• - Background in transportation, logistics, or marketplace platforms.