Full-Time

Strategic Account Executive

Posted on 4/29/2025

HopSkipDrive

HopSkipDrive

501-1,000 employees

Safe child transportation via vetted drivers

Compensation Overview

$110k - $160k/yr

+ Equity Stock Options

No H1B Sponsorship

Minneapolis, MN, USA

Remote

Candidates must reside in and around the Minneapolis, MN area.

Category
Sales & Account Management (1)
Required Skills
Cold Calling

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Requirements
  • 5+ years of experience in B2B enterprise sales, account management or a related role.
  • 3+ years prospecting by phone or in the field including cold dropping in, cold calling, and other common prospecting techniques.
  • Proven ability to listen, understand, and redirect prospects to the solution we are offering.
  • Experience negotiating B2B contracts with multiple stakeholders and implementing tactics both internally and externally to bring the deal to a close.
  • Proven ability to craft and deliver persuasive, engaging presentations to a range of audiences, including decision makers, influencers, and executive leadership.
  • Experience traveling up to 50% of the time (including overnight), staying organized, dropping in on prospects, presenting or making conversation to move the deal forward.
Responsibilities
  • Seek to identify and understand the transportation challenges and opportunities of net-new prospects, ultimately tailoring proposals that align HopSkipDrive’s offerings and value proposition with client needs.
  • Regularly build the pipeline, negotiate terms, and execute by closing new business.
  • Demonstrate value and earn business through a variety of sales formats including email correspondence, in person, via video call, or phone while using tools like slide decks, demos, and marketing collateral.
  • Ask questions and actively listen to understand our prospective clients goals, motivations, and abilities as well as to determine key stakeholders essential to closing the deal.
  • Collaborate with internal teams including Support, Product, Trust & Safety, and Operations to implement client feedback and optimize our offerings to their needs.
  • Dedicate up to 50% of your time to travel within your assigned territory (including overnight) for invaluable face to face meetings, follow ups, and cold prospecting with prospects within the California and Washington.

HopSkipDrive provides specialized transportation for children, connecting families, schools, and social service agencies with vetted CareDrivers who ensure safe and reliable rides to school, activities, and essential appointments. How it works: CareDrivers set their own hours and undergo extensive background checks and training, with technology and logistics coordinating pickups, routes, and on-time arrivals. The company earns service fees from families and partner institutions, focusing on safety and dependability rather than general ride-hailing. What sets HopSkipDrive apart is its mission-driven model: a focus on child safety, formal partnerships with school districts and counties, and a rigorous driver vetting process that enables scheduled, organized transportation for youth. The goal is to make sure children reach their destinations safely, on time, and with trusted adults supervising the ride while offering flexible earning opportunities for CareDrivers.

Company Size

501-1,000

Company Stage

Series D

Total Funding

$107M

Headquarters

Los Angeles, California

Founded

2014

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Simplify Jobs

Simplify's Take

What believers are saying

  • July 2026 Spanish-language caregiver app broadens adoption across 2,000 districts and partner agencies.
  • May 2026 RouteWise AI passed $100 million district savings, strengthening procurement ROI.
  • March 2026 safety report and in-app ride recording reinforce the safety message buyers demand.

What critics are saying

  • The 2026 data-breach settlement keeps reputational damage alive and renews security scrutiny.
  • School districts can replace HopSkipDrive with in-house routing software and local carriers.
  • A fatal rider-safety incident would trigger district cancellations and existential trust collapse within weeks.

What makes HopSkipDrive unique

  • HopSkipDrive owns a specialized child-transportation niche; general rideshare rivals avoid this liability.
  • RouteWise AI and RideIQ bundle routing, billing, recording, and compliance for districts.
  • Direct CareDriver relationships create auditable trips, unlike subcontracted broker fleets with opaque accountability.

Help us improve and share your feedback! Did you find this helpful?

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Life Insurance

401(k) Retirement Plan

401(k) Company Match

Unlimited Paid Time Off

Company Equity

Stock Options

Health Savings Account/Flexible Spending Account

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

1%

2 year growth

6%
01net
Jul 21st, 2026
HopSkipDrive introduces their Spanish language app for caregivers.

HopSkipDrive introduces their Spanish language app for caregivers. 21 Luglio 2026 New Spanish-language experience across the app, ride notifications, and live support helps districts better serve Spanish-speaking families, with more languages planned for the 2026-2027 school year LOS ANGELES-(BUSINESS WIRE)-HopSkipDrive, the leader in safe, fast, and simple supplemental student transportation, today announced the launch of Spanish-language HopSkipDrive app for caregivers. The app updates automatically for caregivers whose phones are already set to Spanish, with no download or setup required. Now, Spanish-speaking parents and caregivers can navigate the app, track rides in real time, and receive ride notifications, with the option to get help from a Spanish-speaking support agent if they need it. For thousands of families, that means no more guessing what a text means or waiting for someone else to translate a pickup alert. Spanish is the first language HopSkipDrive has added to the app for caregivers beyond English, with additional languages planned for the 2026-2027 school year. The update reaches Spanish-speaking families across HopSkipDrive's national network of more than 14,500 schools and 2,000 school districts, government, and nonprofit partners. This update comes as districts are asked to serve increasingly diverse student populations, often without any increase in staff or budget. Families speak different languages. Transportation solutions should too. That's why HopSkipDrive is investing in language accessibility across the HopSkipDrive app for caregivers. For Spanish-speaking families, this update means: * Real-time ride visibility: Caregivers know the moment their driver is on the way, when their child is picked up, and when they arrive safely, communicated in Spanish. * Fewer missed communications: Direct access to support and updates in their preferred language closes the gap that could mean confusion during the moments that matter most. * A smoother start: HopSkipDrive's Caregiver Great Start program, which already reaches out to new families before their first ride to walk them through the app, is now offered in Spanish as well as English, so Spanish-speaking families are walked through the app in their own language, and front-office staff aren't fielding basic questions on day one either. For districts, the upside is just as clear: fewer calls for support fielded by front-office staff, smoother pickups and dropoffs, and one more reason families trust the transportation their kids depend on - a stronger safety net for the whole district, not just one language group. Accessibility: A Caregiver Experience Built for Every Family HopSkipDrive's Spanish-language rollout is designed to work automatically, without requiring any extra work from district transportation teams. Spanish App Experience: The HopSkipDrive app now automatically detects a Spanish-language device on first launch and displays the full app in Spanish, including ride tracking, notifications, onboarding, and settings, with no setup required. The app simply speaks their language from the first tap. Caregivers can also switch their language preference at any time from the app menu, and the preference is saved to their profile so it persists across devices and app reinstalls. Spanish Ride Notifications: Once a caregiver's language preference is set, push and SMS ride notifications are delivered in Spanish too, from "CareDriver en camino" through drop-off confirmation, giving caregivers timely, clear updates in the language they trust. Spanish-Speaking Phone Support: Caregivers can reach a Spanish-speaking support agent for active rides by calling 844-HOP-SKIP and pressing 8, giving families real help in the moment, in the language they're most comfortable with. "We designed this experience to work from the moment a caregiver opens the app, with no configuration, no extra steps for districts, and no added burden on IT teams," said Corey McMahon, Chief Product & Technology Officer of HopSkipDrive. "For families, it should feel seamless. Spanish language support is the first step toward making that experience accessible to everyone." "When a caregiver can't figure out where their child's ride is because of a language barrier, that's not a usability issue, it's a student-outcome issue," said Joanna McFarland, Co-founder and CEO of HopSkipDrive. "Spanish is our first step toward an app for caregivers that truly serves the diverse communities our district partners rely on us to reach, and it won't be our last." About HopSkipDrive HopSkipDrive is the leader in safe, fast, and simple supplemental student transportation. The company is modernizing the $30 billion school transportation industry through two core solutions: a care-centered transportation marketplace and an industry-leading transportation intelligence platform, RouteWise AI(TM). HopSkipDrive's marketplace supplements school buses and existing transportation options by connecting kids to highly-vetted caregivers on wheels, such as grandparents, babysitters, and nurses in local communities. RouteWise AI helps schools and districts address critical challenges, including budget cuts, bus driver shortages, and reaching climate goals. HopSkipDrive has supported over 14,500 schools across two dozen states, with over 2,000 school districts, government agencies, and nonprofit partners. Millions of rides across 130 million miles have been completed through HopSkipDrive since the company was founded in 2014 by three working mothers.

School Transportation News
Apr 16th, 2026
HopSkipDrive launches "Flexible Invoice Groups" to simplify complex school district billing.

HopSkipDrive launches "Flexible Invoice Groups" to simplify complex school district billing. April 16, 2026 LOS ANGELES, Calif. - HopSkipDrive, the leader in safe, fast, and simple supplemental student transportation, today announced the introduction of Flexible Invoice Groups. This new self-service tool, available directly within the ride management software RideIQ, allowing transportation directors to automate and customize how they group rides - aligning them instantly with specific school budgets, grant funding, or departmental structures. In school transportation,"simple" billing is often a myth. Managing these operations is about more than just a ride; it's about navigating a complex web of budgets, grants, and departmental funding. For large districts, the reality of McKinney-Vento funds, General Ed budgets, and changing Foster Youth placements often means transportation directors end up buried in manual spreadsheets and custom workarounds. Flexible Invoice Groups is designed to simplify these complex needs by putting control back in the hands of districts and eliminating the need for manual workarounds. Every month, the system automatically generates: Custom Budget Alignment: Invoices are automatically pre-sorted into your district's specific "buckets" - such as McKinney-Vento or General Ed. Because riders are mapped to these groups on the backend, your billing arrives already aligned with your funding and departmental structures. | Total Transparency: Every invoice automatically generates a consistent Excel backup with trip-level details. Because STN Media Group maintain a direct relationship with every CareDriver, you get a verified audit trail showing exactly how each student's ride is billed. | Clear Reporting: Access clean, standardized PDFs that are pulled directly from its ride records. Its direct relationship with drivers on its platform means reports are generated directly from its data, not from a middleman's spreadsheet. These PDF reports provide the easy-to-understand documentation that procurement teams often need to share with other departments and district leadership. From a Manual Marathon to Total Accuracy Aligning invoices with internal cost centers used to be a manual marathon, especially for districts juggling multiple funding sources. STN Media Group has transformed that"spreadsheet scramble" into a centralized, automated system, slashing the time spent on reconciliation and freeing your team to focus on what matters most: getting students to school safely and reliably. Unlike unregulated brokers who can subcontract to unknown third-party fleets - leading to "middleman markups" and fragmented data - HopSkipDrive maintains a direct relationship with every CareDriver. This oversight provides the verified audit trail and transparent reporting necessary to protect your district's budget and liability, without the hidden costs. Precision at Scale The strength of Flexible Invoice Groups lies in providing the granular data needed to track every dollar. By enabling admins to create custom groupings and providing a standardized Excel backup for every billing cycle, this feature ensures that your financial reporting stays seamless and manageable, no matter how many rides you're coordinating. At HopSkipDrive, STN Media Group is committed to being a trusted partner in your district's financial health. While Flexible Invoice Groups automates the technical side of billing, it is just one part of its support ecosystem. From Shared Billing that automatically splits costs between districts, to RideIQ reports that provide the documentation needed for Medicaid reimbursements, STN Media Group is giving administrators back their most valuable resource: time. As districts continue to scale their operations, these tools ensure that your billing remains as agile and transparent as you need. About HopSkipDrive HopSkipDrive is the leader in safe, fast, and simple supplemental student transportation. Modernizing the $30 billion school transportation industry through its care-centered transportation marketplace which supplements school buses by connecting kids to highly-vetted caregivers on wheels, such as grandparents, babysitters, and nurses in local communities. HopSkipDrive also offers its industry-leading transportation intelligence platform, RouteWise AI, to address critical challenges, including budget cuts, bus driver shortages, and reaching climate goals. With this technology, HopSkipDrive has supported over 14,500 schools and over 2,000 school districts, government agencies, and nonprofit partners. Since its founding in 2014 by three working mothers, HopSkipDrive has surpassed more than 100 million safe miles driven. This record includes nearly 3 million foster and McKinney-Vento rides and 1.7 million Individualized Education Program (IEP) rides, alongside millions of additional trips for General Education, Career and Technical Education (CTE) programs, and extracurricular activities.

AIJourn
Mar 12th, 2026
HopSkipDrive Elevates Student Safety Standards with Launch of Ride Recording: In-App

HopSkipDrive elevates student safety standards with launch of Ride Recording: In-App. Additional features empower students to track their own rides in real-time for added peace of mind, while ensuring transparency for school districts LOS ANGELES-(BUSINESS WIRE)-HopSkipDrive, the leader in safe, fast, and simple supplemental student transportation, today announced the launch of Ride Recording: In-App. This major safety milestone enhances the company's existing ride recording capabilities, bringing school districts an even more affordable, flexible, and secure recording option than dashcams. This launch joins the new "Track My Ride" web interface designed to increase visibility and transparency. The introduction of Ride Recording: In App represents a significant development in HopSkipDrive's leadership on safety. Available network-wide across all HopSkipDrive markets, 100% of rides this Fall will feature Ride Recording: In-App. This enhances the company's existing dashcam recording solution by utilizing the native camera capabilities of the driver's smartphone. To ensure The AI Journal Ltd. meet the unique needs of every district partner, HopSkipDrive will continue to offer in-ride dashcams for districts that require them. By integrating directly into the device drivers already use for real-time navigation and ride management, Ride Recording: In App enables HopSkipDrive to consistently improve the software while preventing driver intervention or access. To ensure total security and privacy, drivers have zero access to the files, and all footage is automatically wiped from the device after the ride. This software-based innovation also allows the company to scale this feature across all districts effortlessly, meeting interior recording requirements for students of all needs without the high expense or time-consuming process of retrofitting an entire fleet with physical hardware. Captured via a direct system that ensures total security and student privacy while extending visibility and transparency to school districts and HopSkipDrive's Safe Ride Support(R) team, which helps provide human eyes on every ride. In addition to Ride Recording: In-App, HopSkipDrive is proud to announce Track My Ride, which gives riders access to a link to track their journey in real-time. While many riders use the HopSkipDrive app today to see their driver and ride details, the company recognizes that some students rely on wearables, smartwatches, or school- or government-issued devices that do not allow app installs. Track My Ride fosters digital equity by providing secure, masked SMS links that open in a standard web view. This removes the friction of app downloads and eliminates the need for manual staff coordination, creating a simpler, less stressful pickup experience for riders, caregivers, and school staff alike. By providing real-time visibility to every student regardless of their device, HopSkipDrive gives riders the peace of mind they need to feel confident on their way to school while ensuring caregivers no longer need to share access to their account credentials and the caregiver-specific permissions within that app. "At the end of the day, student transportation is built on trust," said Joanna McFarland, Co-founder and CEO of HopSkipDrive. "By introducing Ride Recording: In-App and Track My Ride, we are reinforcing that trust with even greater real-time visibility and a clear record of every journey. We want our partners to have the most reliable safety features available, along with the administrative tools that actually make their jobs easier." About HopSkipDrive HopSkipDrive is a leading technology company partnering with school districts to get kids to school more quickly, safely, and easily than anyone else. The company is modernizing the $30 billion school transportation industry through two core solutions: a care-centered transportation marketplace and an industry-leading transportation intelligence platform, RouteWise AI(TM). HopSkipDrive's marketplace supplements school buses and existing transportation options by connecting kids to highly-vetted caregivers on wheels, such as grandparents, babysitters, and nurses in local communities. RouteWise AI helps schools and districts address critical challenges, including budget cuts, bus driver shortages, and reaching climate goals. HopSkipDrive has supported over 13,500 schools across 21 states, with nearly 1,300 school districts, government agencies, and nonprofit partners. More than five million rides over 95 million miles have been completed through HopSkipDrive since the company was founded in 2014 by three working mothers.

Business Wire
Mar 12th, 2026
HopSkipDrive launches in-app ride recording for student transport safety across all US markets

HopSkipDrive, a student transportation company, has launched Ride Recording: In-App, a software-based safety feature that uses drivers' smartphone cameras to record all rides. The system will be available across all markets this autumn, with 100% of rides featuring the technology. The in-app recording solution enhances HopSkipDrive's existing dashcam capabilities whilst offering a more affordable and flexible alternative. Drivers cannot access recorded footage, which is automatically deleted from devices after rides. The company will continue offering physical dashcams for districts requiring them. HopSkipDrive also introduced Track My Ride, a web-based interface allowing students to track journeys in real-time via SMS links, eliminating app download requirements. Founded in 2014, the company has completed over five million rides across 21 states, serving nearly 1,300 school districts and partners.

Remote Source
Dec 15th, 2025
Alpaca your bags

Alpaca your bags. Inside: Alpaca has team members in almost every time zone, and they're hiring. Plus: Honor and HopSkipDrive, two remote-first companies in the caregiver space, are hiring as well. Really feels like we're in the home stretch for the year now. After this week we're into Christmas and New Years! Still trying to wrap my head around using the date "2026" but I suppose I can save that battle for a few weeks from now. Alpaca, Honor, and HopSkipDrive are featured this week, collectively hiring for almost 60 remote jobs. Best of luck in your search! Companies hiring remotely. * Alpaca builds financial services APIs and bridges the gap between those who can access financial services and those who cannot. * From their Careers page: "Our teams are not just global, we're also 100% remote and have team members in almost every time zone and continent (except Antarctica). By joining Alpaca you'll be part of a multicultural, international organization." * See their job openings here. * Honor is a technology-enabled home care company that partners with local agencies and health systems to provide in-home care for older adults by matching them with professional caregivers and coordinating care through a centralized platform. * From their Careers page: "A remote-first work model lets you work from anywhere in the U.S. or occasionally pop into a satellite office." * See their job openings here. * HopSkipDrive is a transportation platform that provides safe, reliable rides for children and seniors, using vetted caregivers and drivers to support families, schools, and care organizations. * From their Careers page: "we believe strongly that most roles allow for a remote-first approach to work. We support employment across the U.S. and employee flexibility to accommodate personal commitments, which we believe ultimately leads to a more inclusive and diverse workforce." * See their job openings here. 20,000+ remote jobs. Remote-First focus. * Remote Source is the only remote job board with a certified Remote-First filter - these companies aren't about to force you back into an office. * We guarantee no scams because we hand-pick each employer featured on the job board. * All of our company feeds are updated multiple times per day, so you can be the first to apply to your favorite jobs. * With a free account, you can view all jobs on the job board. That's already more than what most remote job boards can say! * For less than $1/week, | Pro users get even more: * Remote-First Company search filter * Leadership Roles search filter * Daily custom email alerts * Unlimited saved jobs * Unlimited saved searches If you're serious about finding a remote job ASAP, or you don't have time to search for new remote jobs every single day, the | Pro plan was built for you. Try it out today: Helpful links. The Remote Source job board has 20,000+ open remote jobs, all from hand-picked, established companies. It's updated daily, and it's completely free to access all jobs, unlike most major remote job boards. PRO users can filter for remote-first companies and Leadership Roles, get unlimited saved jobs and searches, AND get daily email alerts for jobs matching their search criteria. If you'd like to get more updates from us throughout the week, you can find us on Instagram, X, LinkedIn, Facebook, and Threads. I'll ship your choice of a Remote Source Yeti or Stanley mug to the first person who can guess where this was taken

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