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Regional Account Manager- Future Opportunity

HopSkipDriveRemote USA Sales
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Salary
$85K - $90K USD
Job type
Full-time
Work mode
Remote
Posted
4 Jun 2026
Status
Open · checked 7d ago

About this role

Role Overview

The Regional Account Manager at HopSkipDrive is a remote, revenue-owning position responsible for managing a Tier 2 book of business across assigned regions in the United States. This opportunity suits an experienced professional with a background in consultative sales or account management who can drive retention, expansion, and client satisfaction within school districts.

Key Responsibilities

Dedicate two to three days every week to on-site client visits to build relationships, understand client needs, and drive engagement, alongside any necessary national travel using reliable transportation.
Drive strategic expansion across the product suite through structured discovery and Challenger methodology, creating multi-threaded stakeholder plans.
Deliver exceptional service while maintaining strong, multi-threaded relationships across operational, technical, and executive client stakeholders.
Lead multi-department discovery within districts to uncover unmet needs and quantify new revenue opportunities.
Communicate confidently with client executives to influence decision-making using data, insights, and outcome-based recommendations.
Align internal teams including Sales, Operations, Product, Finance, Trust and Safety, and Support around client priorities.
Lead renewals and expansions, managing structured negotiations and closing motions.
Utilize artificial intelligence to craft personalized meeting agendas, synthesize stakeholder needs, draft follow-up communications, and summarize Salesforce data for executive insights.

Requirements

Five or more years of professional experience working in Account Management, Customer Success, or Consultative Sales within SaaS, marketplace, logistics, or services sectors.
Proven track record of owning retention and expansion revenue.
Strong executive communication, presentation, and negotiation skills.
Demonstrated success in managing complex, multi-stakeholder accounts.
Advanced CRM discipline and data fluency, specifically with Salesforce or equivalent tools.
Experience leading cross-functional account execution while operating comfortably in ambiguous environments.
High operational rigor with the ability to integrate artificial intelligence into daily workflows.

Nice to Have

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

Skills and Tools

Account Management
Consultative Sales
SaaS and Marketplace Platforms
Salesforce CRM
Challenger Methodology
Executive Communication
Cross-Functional Leadership
Artificial Intelligence Workflows

Salary and Benefits

Base salary ranging from $85,000 to $90,000 per year, with a total on-target earnings range of $130,000 to $140,000.
Equity stock options for full-time employees to share in company growth.
Comprehensive medical, dental, vision, and life insurance coverage.
Flexible vacation policy.
Participation in a 401(k) plan and Flexible Spending Account (FSA).

About the Company

HopSkipDrive is a leader in safe, fast, and simple supplemental student transportation, connecting children with vetted caregivers through an innovative marketplace and software. Founded by three moms to solve transportation challenges, the company has facilitated over five million rides across more than 20 states and has raised $100 million as a Series D backed organization. The team leverages artificial intelligence at every level to rethink how work gets accomplished and builds lasting partnerships with school districts and government agencies.

How to Apply

Please visit the official HopSkipDrive careers page to submit your application for the Regional Account Manager position.

Questions candidates ask

What is the location of the Regional Account Manager role?

This position is remote within the USA, but it requires spending two to three days each week on-site for regional client visits.

What is the salary range for this job?

The base salary ranges from $85,000 to $90,000 per year, with an OTE range of $130,000 to $140,000, plus equity stock options.

How many years of experience are required?

Candidates must have five or more years of experience in Account Management, Customer Success, or Consultative Sales.

What tools and technologies are used daily?

The role requires advanced CRM discipline, specifically using Salesforce or equivalent platforms, alongside daily integration of artificial intelligence workflows.

What benefits are provided by HopSkipDrive?

Full-time employees receive equity stock options, flexible vacation, medical, dental, vision, life insurance, 401(k), and FSA benefits.

Ready to apply?

The application is on the official HopSkipDrive careers page.

Apply on company site