Regional Account Manager

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

8d•$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 ensuring client retention, driving account expansion, and maintaining overall account health. The RAM will act as the strategic lead for complex districts, working with Regional Sales Management to set and execute account strategies. They will also provide recommendations for necessary resources to senior staff, collaborate with Metro Service Managers for operational excellence, and identify product gaps and penetration strategies. This is a revenue-generating position focused on achieving measurable outcomes through strategic account planning, Challenger-led selling, and cross-functional execution. Success hinges on strong client communication, commercial acumen, operational rigor, and the ability to align internal teams 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.
Reliable transportation is required.
Candidates must be based in the Great Lakes Region (PA, MI, IL, WI).

Nice To Haves

Experience in education, government, or regulated markets.
Familiarity with Challenger or similar insight-led sales methodologies.
Background in transportation, logistics, or marketplace platforms.

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.
Own retention, expansion, and overall performance of named accounts.
Deliver exceptional client service and build/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.