Regional Account Manager- Future Opportunity

HopSkipDrive

8d•$130,000 - $140,000•Remote

About The Position

HopSkipDrive is a leader in supplemental student transportation, connecting children with vetted caregivers through a marketplace and solving transportation challenges for schools and districts with their software. Founded by three mothers, the company has facilitated over five million rides and is rapidly growing, having been recognized on the Inc. 5000 and Deloitte 500 lists. HopSkipDrive utilizes AI extensively in its operations and is seeking a driven, mission-focused individual to join their Revenue team. The team's goal is to drive revenue growth, deliver client value, and innovate in mobility while making a positive impact.

Requirements

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

Responsibilities

Manage day-to-day account management and long-term account strategy for a Tier 2 book of business.
Own retention, expansion, and overall account health.
Serve as the strategic quarterback for complex districts.
Set and execute account strategy with support from Regional Sales Management.
Provide recommendations to senior staff for required resources.
Collaborate cross-functionally with Metro Service Managers to drive operational excellence at the account level.
Identify product-level gaps and strategies for product penetration by account.
Drive measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution.
Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement.
Spearhead enterprise growth by driving 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.
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.
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 offerings.
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.