Sr. Regional Account Manager

About HopSkipDrive:

HopSkipDrive's mission is to create opportunity for all through mobility. We are the leader in safe, fast, and simple supplemental student transportation, connecting children with highly-vetted Caregivers on Wheels through our marketplace software. We solve critical transportation challenges for schools and districts nationwide. Founded by three moms, we have facilitated over five million rides across more than 20 states and have earned recognition on the Inc. 5000 and Deloitte 500 lists. HopSkipDrive is a Series D company with $100M raised to date.

How We Work:

We are an AI-forward company, expecting all team members to leverage AI tools for drafting, analyzing, building, and shipping faster. We provide training and encourage thoughtful AI governance. We are remote-first, mission-driven, and built for individuals who want to do meaningful work with a high-caliber team.

Who We Are:

We are a driven, mission-focused team passionate about transforming transportation through innovation and impact. We build lasting partnerships with school districts and government agencies. As a Revenue team, our goal is to drive revenue growth, deliver client value, and redefine mobility while making a difference for those in need.

The Sr. Regional Account Manager (RAM) is responsible for day-to-day account management and long-term strategy for a Tier 1 book of business. This role owns retention, expansion, and overall account health, 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 senior, revenue-owning role requires advanced client communication, commercial acumen, operational rigor, and the ability to influence internal and external stakeholders.

Key Job Responsibilities:

• In-Person Client Engagement: Dedicate 2-3 days weekly to on-site client visits. Reliable transportation is required, and additional national travel may be necessary.
• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrive’s product suite using structured discovery and Challenger methodology. Build and execute district-level growth strategies, owning retention, expansion, and performance of named accounts.
• Manage Client Accounts: Deliver exceptional client service, building and maintaining 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 opportunities. Drive expansion through structured discovery and Challenger methodology.
• Communicate Tailored Value: Confidently communicate with client executives, influencing decision-making with data, insights, and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales, Operations, Product, Finance, Trust & Safety, and Support around client priorities and optimize offerings.
• Lead Pricing Discussions: Lead renewals and expansions, including structured negotiations and closing motions.
• AI Enabled Operational Excellence: Utilize AI for personalized meeting agendas, synthesizing stakeholder needs, and drafting follow-up communications. Leverage AI for Salesforce (SFDC) data summaries, transforming metrics into actionable, insight-led recommendations. Employ AI to assist in building recurring account reports, identifying product gaps, and creating scalable growth strategies.

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

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:

• Equity ownership in the company.
• Flexible vacation, medical, dental, vision, and life insurance.
• 401(k), FSA.
• Opportunity to work for a uniquely positioned, VC-backed company in a high-growth space.

Compensation:

The salary range for this role is $90,000 - $100,000 base with an On-Target Earnings (OTE) of $150,000 - $170,000. Compensation will be determined by relevant work experience, skill set, certifications, and specific work location. The total compensation package includes equity stock options.

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

Equal Opportunity Employer:

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.