Regional Account Manager

At HopSkipDrive our goal is to create opportunity for all through mobility.

Were a technology company that solves complex transportation challenges where there is a heightened need for safety equity and care. Through our marketplace we connect kids older adults or anyone needing extra support to highly-vetted caregivers on wheels. Through our software we solve the biggest transportation challenges facing schools and school districts around the country.

Founded by three moms as a solution to their own transportation challenges weve now facilitated more than five million rides across over 17 states around the country. We continue to expand at a rapid pace making the Inc. 5000 list four times as well as the Deloitte 500 Fast-Growing Technology list. HopSkipDrive is a Series D company and has raised $100M in funding to date.

Who We Are

We are a driven mission-focused team passionate about transforming transportation through innovation and impact. Rather than just selling a service we build lasting partnerships with school districts and government agencies solving their toughest challenges with our vetted CareDriver marketplace and cutting-edge solutions.

As a Revenue team our goal is clear: drive revenue growth deliver value to our clients and redefine whats possible in mobility while making a meaningful difference for those who need it most.

The Role

The Regional Account Manager (RAM) is responsible for day-to-day account management and long-term account strategy across a Tier 2 book of business. This role owns retention expansion and overall account health while serving as the strategic quarterback for complex districts. With support from Regional Sales Management the RAM sets and executes account strategy and provides recommendations to senior staff for required resources collaborates cross-functionally with Metro Service Managers to drive operational excellence at the account level and plays an active role in identifying product-level gaps and strategies for product penetration by account.

This is a revenue-owning role focused on driving measurable outcomes through strategic account planning Challenger-led selling and cross-functional execution. Success requires strong client communication skills demonstrated commercial acumen high operational rigor and the ability to proactively coordinate and align both internal cross-functional partners and senior external stakeholders.

To excel in this role you will be expected to take ownership of and demonstrate the following key job responsibilities:

• In-Person Client Engagement: Dedicate 2-3 days each week to on-site client visits to foster relationships deepen understanding of client needs and drive meaningful engagement. Additional national travel may be needed and reliable transportation is required.
• Spearhead Enterprise Growth: Drive strategic expansion across HopSkipDrives 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.
• Manage Client Accounts: Deliver exceptional client service build and maintain strong multi-threaded relationships across operational technical and executive stakeholders.
• Seek Net-New Opportunities: Lead multi-department discovery within districts to uncover unmet needs and quantify opportunity. Drive strategic expansion across HopSkipDrives product suite through structured discovery and Challenger methodology.
• Communicate Tailored Value: Communicate confidently with client executives influencing decision-making through data insight and outcome-based recommendations.
• Partner Cross-Functionally: Align Sales Operations Product Finance Trust & Safety and Support around client priorities and optimize our offerings to their needs.
• Lead Pricing Discussions:Lead renewals and expansions including structured negotiations and closing motions
• AI Enabled Operational Excellence: Utilize AI to craft personalized meeting agendas synthesize complex stakeholder needs and draft high-impact follow-up 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 you will minimize administrative overhead dedicating more time to discovery and deepening multi-threaded district relationships.

Who You Are

Required

• 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.

Our Investment In You:

We want you to be an owner in our company and share in executing our vision so every full-time employee has addition we offer flexible vacation medical dental vision and life insurance 401(k) FSA and an opportunity to work for a uniquely positioned VC-backed company in a hugely attractive space with significant upside potential. HopSkipDrive is committed to fair and equitable compensation practices. The salary range for this role is an $ base with an OTE of $130000 - $140000. This position is remote and as such compensation will ultimately be in line with the location in which the position is filled. Final compensation for this role will be determined by several factors such as a candidates relevant work experience skill set certifications and specific work location. The total compensation package for this role also includes equity stock options.

HopSkipDrive is proud to be an equal-opportunity employer. All qualified applicants will receive consideration for employment without regard to race color religion gender gender identity or expression sexual orientation national origin genetics disability age veteran status or any other protected class.

NOTE* This role will be remote but candidates must be based in (Northern CA / Bay Area) . There will be travel required. The role will require 2-3 days on-site client visits every week.