Regional Account Manager

HopSkipDrive•Remote USA WI, MN, IL, MI, PA, MI

10d•$85,000 - $90,000•Remote

About The Position

HopSkipDrive is seeking a Regional Account Manager (RAM) to manage day-to-day account operations and develop long-term strategies for a Tier 2 book of business. This role is crucial for client retention, expansion, and overall account health, acting as a strategic lead for complex districts. The RAM will set and execute account strategies, recommend necessary resources to senior staff, collaborate with Metro Service Managers for operational excellence, and identify product gaps and penetration strategies. This revenue-focused position emphasizes strategic account planning, Challenger-led selling, and cross-functional execution, requiring strong client communication, commercial acumen, operational rigor, and the ability to align internal and external stakeholders.

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 for travel.

Responsibilities

Dedicate 2-3 days each week to on-site client visits to foster relationships, deepen understanding of client needs, and drive meaningful engagement.
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.
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.