Sr. Regional Account Manager

HopSkipDrive

2d•$90,000 - $170,000•Remote

About The Position

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 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. How we work We're an AI-forward company, and we expect every person on our team to be too. We use AI tools to do our best work — drafting, analyzing, building, and shipping faster than we could without them — and we invest in training, share what works, and govern AI use thoughtfully. We don't expect you to be an expert when you start. We do expect you to be curious, willing to learn, and ready to use the best tools available to move our mission forward. We're remote-first, mission-driven, and built for people who want to do work that matters with people who hold a high bar. 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.

Requirements

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.
High operational rigor and the ability to leverage AI into daily workflows.

Nice To Haves

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

Responsibilities

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.
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.
Deliver exceptional client service, build and maintain strong, multi-threaded relationships across operational, technical, and executive stakeholders.
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 confidently with client executives, influencing decision-making through data, insight, and outcome-based recommendations.
Align Sales, Operations, Product, Finance, Trust & Safety and Support around client priorities and optimize our offerings to their needs.
Lead renewals and expansions, including structured negotiations and closing motions.
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.