Sr. 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 over 20states. 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.

How we work

We use AI every day, and not as a productivity add-on. It's woven into how we work at every level. We're rethinking how work gets done, who does what, and what a small team can accomplish. If you've already built AI into how you work, you'll hit the ground running. If you haven't, you'll need to be ready to learn fast and work differently than you have before.

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.

The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 1 book of business. This role owns retention, expansion, and overall account health while serving as the strategic quarterback for complex districts. The Sr. RAM leads account-level strategy with limited oversight and supports Key Accounts in partnership with Regional Sales Managers.

This is a senior, revenue-owning role focused on driving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success requires advanced client communication, strong commercial acumen, operational rigor, and the ability to influence both internal and external stakeholders.

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 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.
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas, synthesize complex stakeholder needs, and draft high-impact follow-up communications. Leverage AI to generate automated summaries of Salesforce (SFDC) data, transforming raw metrics into actionable, insight-led recommendations for executive stakeholders. Employ AI to assist in building recurring account reports, identifying product-level gaps, and creating scalable growth strategies that prioritize client outcomes by automating routine reporting and documentation, you will minimize administrative overhead, dedicating more time to discovery and deepening multi-threaded district relationships.

Who You Are:

Required

• 8+ 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.
• Experience in education, government, or regulated markets highly preferred
• Familiarity with Challenger or similar insight-led sales methodologies highly preferred
• Background in transportation, logistics, or marketplace platforms highly preferred
• High operational rigor and the ability to leverage AI into daily workflows

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 $90,000-100,000 base with an OTE of $150,000 - $170,000. 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.

NOTE* The role will require 2-3 days on-site client visits regionally.