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Sr. Regional Account Manager

HopSkipDriveRemote USASales
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Salary
$90K - $100K USD
Job type
Full-time
Work mode
Remote
Posted
5 Jun 2026
Status
Open · checked 9d ago

About this role

The Sr. Regional Account Manager at HopSkipDrive is a senior, revenue-owning remote position responsible for overseeing a Tier 1 book of business and driving long-term account strategy. This role suits an experienced professional ready to lead account retention, expansion, and overall health for complex school districts across the country.

Role Overview

As a Sr. Regional Account Manager, the professional acts as a strategic quarterback for complex districts with limited oversight. The incumbent takes ownership of strategic account planning, Challenger-led selling, and cross-functional execution to deliver measurable outcomes. The position requires dedicating two to three days each week to on-site client visits regionally, alongside potential national travel and reliable transportation.

Key Responsibilities

Build and execute district-level growth strategies, owning client retention, expansion, and overall performance of named accounts.
Drive strategic expansion across the company product suite through structured discovery and Challenger methodology.
Deliver exceptional client service and foster multi-threaded relationships across operational, technical, and executive stakeholders.
Communicate confidently with client executives, influencing decisions through data, insights, and outcome-based recommendations.
Lead renewals, expansions, structured negotiations, and closing motions.
Partner cross-functionally with Sales, Operations, Product, Finance, Trust & Safety, and Support teams.
Utilize artificial intelligence to craft personalized meeting agendas, synthesize stakeholder needs, summarize Salesforce data, and automate routine reporting.

Requirements

At least 8 years of professional experience 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 and presentation 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.
Comfort operating within ambiguity while maintaining accountability for outcomes.
High operational rigor with the ability to integrate artificial intelligence into daily workflows.

Nice to Have

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

Skills and Tools

Account Management and Consultative Sales
SaaS, marketplace, and logistics environments
Salesforce or equivalent CRM tools
Challenger sales methodology
Executive communication and presentation
Cross-functional leadership and negotiation
AI-enabled workflow execution

Salary and Benefits

Base salary range of $90,000 to $100,000 per year with an On-Target Earnings (OTE) range of $150,000 to $170,000.
Equity stock options for every full-time employee.
Flexible vacation policy.
Medical, dental, vision, and life insurance coverage.
401(k) retirement 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 real-world transportation challenges, the company has facilitated over five million rides across more than 20 states. Recognized frequently on the Inc. 5000 and Deloitte Fast-Growing Technology lists, HopSkipDrive is a Series D company that has raised $100 million and deeply integrates artificial intelligence into daily operations.

How to Apply

Interested candidates should visit the official HopSkipDrive careers page to submit an application for this remote position.

Questions candidates ask

What is the salary range for the Sr. Regional Account Manager role?

The base salary ranges from $90,000 to $100,000 per year, with an On-Target Earnings (OTE) range of $150,000 to $170,000, plus equity stock options.

Is this position remote?

Yes, this is a remote position based in the USA, though it requires regional on-site client visits two to three days each week.

How many years of experience are required for this role?

Candidates must have eight or more years of experience in Account Management, Customer Success, or Consultative Sales within SaaS, marketplace, logistics, or services environments.

What tools and technologies are used in this role?

The role requires advanced CRM discipline and data fluency using Salesforce or an equivalent platform, alongside daily use of artificial intelligence for workflow optimization and reporting.

What benefits are provided by HopSkipDrive?

Benefits include company equity, flexible vacation, medical, dental, vision, and life insurance, a 401(k) plan, and a Flexible Spending Account (FSA).

Ready to apply?

The application is on the official HopSkipDrive careers page.

Apply on company site