HopSkipDrive
Transportation
Sr.RegionalAccountManager
Neural analysis suggests this role is
optimal for Senior candidates.
“Sr. Regional Account Manager at HopSkipDrive. Skills: Account Management, Revenue Growth, Client Relationships, AI Utilization. Manage day-to-day account management. Develop long-term account strategy”
What You'll Achieve.
Drive revenue growth; Deliver value to clients; Redefine mobility possibilities; Make meaningful difference; Drive measurable outcomes; Minimize administrative overhead
Industry & Context.
Data-driven decision making
2-3 days on-site client visits regionally, Additional national travel, Reliable transportation required
What They're Looking For.
Must Have
8+ years Account Management, 8+ years Customer Success, 8+ years Consultative Sales, Proven ownership of retention, Proven ownership of expansion revenue, Executive communication skills, Executive presentation skills, Demonstrated success managing complex accounts, Demonstrated success managing multi-stakeholder accounts, Advanced CRM discipline, Data fluency, Experience leading cross-functional account execution, Comfort operating in ambiguity, Accountability for outcomes
Nice to Have
Experience in education, Experience in government, Experience in regulated markets, Familiarity with Challenger methodology, Familiarity with insight-led sales, Background in transportation, Background in logistics, Background in marketplace platforms, High operational rigor, Ability to leverage AI into workflows
What You'll Do.
Manage day-to-day account management
Develop long-term account strategy
Own overall account health
Serve as strategic quarterback for districts
Lead account-level strategy
Drive measurable outcomes
Develop strategic account plans
Employ Challenger-led selling
Execute cross-functionally
Communicate with clients
Influence decision-making
Dedicate 2-3 days weekly to client visits
Foster client relationships
Deepen understanding of client needs
Drive meaningful client engagement
Travel nationally as needed
Spearhead enterprise growth
Drive strategic expansion
Conduct structured discovery
Employ Challenger methodology
Build district-level growth strategies
Develop multi-threaded stakeholder plans
Own performance of named accounts
Deliver exceptional client service
Build multi-threaded relationships
Lead multi-department discovery
Communicate tailored value
Influence executive decision-making
Align Sales around client priorities
Align Operations around client priorities
Align Product around client priorities
Align Finance around client priorities
Align Trust & Safety around client priorities
Align Support around client priorities
Optimize offerings to client needs
Conduct structured negotiations
Execute closing motions
Utilize AI for meeting agendas
Utilize AI to synthesize stakeholder needs
Draft high-impact follow-up communications
Leverage AI for Salesforce data summaries
Transform metrics into actionable recommendations
Employ AI for recurring account reports
Identify product-level gaps
Create scalable growth strategies
Automate routine reporting
Automate documentation
How You'll Work.
Team & Collaboration
Cross-functional execution; Internal stakeholders; External stakeholders; Sales; Operations; Product; Finance; Trust & Safety; Support
Communication Scope
Executive communication; Executive presentations; Client communication; Data-driven recommendations
Full Job Description
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 o
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