Job Overview
Location
Remote USA San Francisco Bay
Job Type
Full-time
Category
Sales
Date Posted
May 6, 2026
Full Job Description
đź“‹ Description
- • The Regional Account Manager (RAM) at HopSkipDrive is a revenue-owning role responsible for day-to-day account management and long-term strategy across a Tier 2 book of business, driving retention, expansion, and overall account health while serving as the strategic quarterback for complex school districts and government agencies.
- • Day to day, the RAM will dedicate 2-3 days per week to in-person client visits to build relationships and understand needs, lead enterprise growth using Challenger methodology, manage multi-threaded stakeholder relationships, seek net-new opportunities through discovery, communicate tailored value to executives, partner cross-functionally with Sales, Operations, Product, Finance, Trust & Safety, and Support teams, lead pricing discussions in renewals and expansions, and leverage AI tools to automate reporting, synthesize stakeholder needs, and generate actionable insights from Salesforce data.
- • HopSkipDrive is a mission-driven technology company solving transportation challenges for vulnerable populations through a vetted caregiver marketplace and software solutions for schools. Founded by three moms, the company has facilitated over five million rides across 17 states, is a Series D company with $100M in funding, and has been recognized on the Inc. 5000 and Deloitte 500 lists. The Revenue team focuses on driving growth, delivering value, and redefining mobility through innovation and impact.
- • In this role, the RAM will develop deep expertise in strategic account planning, Challenger-led selling, and cross-functional execution; strengthen executive communication and presentation skills; gain experience operating in complex, regulated markets like education and government; master AI-enabled workflows to increase operational efficiency; and own measurable outcomes in retention, expansion, and revenue growth while contributing to a mission that creates opportunity through mobility.
🎯 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
- • 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 ability to leverage AI into daily workflows
- • Experience in education, government, or regulated markets
- • Familiarity with Challenger or similar insight-led sales methodologies
🏖️ Benefits
- • Equity stock options for all full-time employees
- • Flexible vacation policy
- • Medical, dental, vision, and life insurance
- • 401(k) and FSA plans
- • Opportunity to work for a VC-backed company with significant upside potential in a high-growth market
- • Commitment to fair and equitable compensation practices
Skills & Technologies
See exactly how your profile matches this role — strengths, skill gaps, and what to do about them.
About HopSkipDrive Inc.
California-based safe youth transportation company providing scheduled rides for children aged 6-17 through a technology platform that matches families, schools and government agencies with fully vetted and monitored CareDrivers using their own cars. Services include home-to-school, school-to-activities and foster care mobility solutions, supported by real-time tracking, strict safety protocols and compliance expertise for school districts and child welfare organizations nationwide.
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