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HopSkipDrive

Safe child transportation via vetted drivers

Engineering Manager - Platform & DevOps

Full-TimeUpdated on 10/23/2026
$180k - $205k+ Equity stock options
Mid
Remote in USA
RemoteFully remote; candidates must reside and work in one of the listed states.
Engineering ManagementEngineering Leadership

About the job

Requirements
  • Hands-on experience as a Platform or DevOps engineer who has stepped into leadership, managed engineers, and continued to contribute technically.
  • Experience leading a team through on-call operations, incident response, platform growth, and AI/agentic transformation.
  • Deep knowledge of AWS, infrastructure as code using Terraform, Kubernetes, and Postgres, with production experience operating a large web and mobile application surface area.
  • Experience applying coding agents and large language model (LLM) tooling in a software lifecycle, including continuous integration (CI) integration, evaluation, guardrails, and cost control.
  • Experience improving how an engineering organization adopts coding agents and LLM tooling.
  • Knowledge of continuous integration and continuous delivery (CI/CD), regression-suite platform coverage, and approaches for keeping regression suites fast and trusted.
  • Ability to help engineers transition from manual to automated testing.
  • Fluency in delivery and reliability metrics and ability to use them to coach a team rather than rank people.
  • Ability to build alignment through written proposals and decision records in a remote, asynchronous company.
  • Track record of independently adopting generative AI to accelerate personal and team work.
  • Curiosity and willingness to experiment with new tools.
Responsibilities
  • Lead and grow a team of Platform and DevOps engineers; set direction, coach, hire, and remain hands-on for part of the week.
  • Own the AWS platform end-to-end, including infrastructure as code, Kubernetes, continuous integration and continuous delivery, environments, observability, incident response, and cloud costs.
  • Lead the practice of the Agentic Software Development Lifecycle (ASDLC) to ensure AI tools remain safe, aligned, and continuously improving.
  • Enable product teams to make automated verification standard by releasing with embedded tests across web and mobile.
  • Deliver deployment environments and continuous integration pipelines that keep pace with agent-generated changes.
  • Measure and improve system delivery, including baseline time in continuous integration, code review, and quality assurance.
  • Build alignment in writing with product and engineering leaders on the platform roadmap and investment trade-offs.

About the company

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

  • September 2026 CareEngine launch tackles district exception handling during driver shortages.
  • May 2026 free nationwide ride recording lowers district hardware costs and friction.
  • July 2026 Spanish caregiver app expands accessibility across 14,500 schools and 2,000 partners.

What critics are saying

  • The 2023 data breach settled for $1.985 million in 2026, signaling trust exposure.
  • Districts switch away if RouteWise AI and CareEngine fail to cut manual work.
  • A single serious safety incident ends school contracts and crushes the marketplace.

What makes HopSkipDrive unique

  • CareEngine coordinates districts, families, riders, and CareDrivers around exceptions, not fixed routes.
  • HopSkipDrive still owns direct relationships with CareDrivers, preserving safety controls and audit trails.
  • Ride recording, Track My Ride, and Spanish caregiver support deepen trust for schools.

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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

6 month growth

-2%

1 year growth

0%

2 year growth

0%
School Transportation News
Oct 22nd, 2026
What HopSkipDrive's Safety Advisory Council has helped build.

What HopSkipDrive's Safety Advisory Council has helped build. More than a year after forming the council, independent safety experts have helped shape new rider-safety features and real policy progress, with more work underway October 22, 2026 LOS ANGELES, Calif. - HopSkipDrive, the leader in safe, fast, and simple supplemental student transportation, today highlighted the ongoing work of its Safety Advisory Council (SAC), an independent group of experts who advise the company on the safety of riders, drivers, and clients. Since forming in May 2025, the council has met regularly, most recently at a hands-on, workshop-style session in Denver. That session produced a draft safety framework that sharpens HopSkipDrive policies and is moving into product development. The council brings together specialists across child passenger safety, road safety, human trafficking prevention, K-12 mental health, and transportation consulting, alongside members with lived experience as crash survivors. Their guidance shapes work ranging from in-vehicle recording and rider verification to how HopSkipDrive supports students with Individualized Education Programs (IEPs), youth in foster care, and students experiencing homelessness. "HopSkipDrive is built with students' safety at the center of what we do. Safety is the reason we started the company, and having outside experts in the room has already changed how we build," said Joanna McFarland, Co-Founder and CEO of HopSkipDrive."We didn't get to better rider verification, or the policy ground we've gained, without them. Their questions get us there faster than we ever could alone." Over a Year of Concrete Progress Over the past year, HopSkipDrive has moved several council-informed initiatives from concept to practice, including: Ride Recording: In-App, part of CareEngine, captures audio and video on every eligible ride, encrypted and available to districts through RideIQ. CareDrivers never see the footage, and the program runs under a formal consent and retention framework. | A council-informed push to strengthen rider verification beyond the traditional spoken code word, with new ways to confirm the right rider is getting into the right vehicle. | Continued investment in structured rider and IEP data, replacing open-text notes with consistent, actionable detail so CareDrivers can better support each rider's needs. | Policy engagement that helps raise industry-wide screening and accountability standards while preserving specialized safeguards for child transportation, backed by continued monitoring of state and federal legislation that affects how districts get students to school safely. "We're in the room while frameworks are still being drafted, and that gives our feedback more weight than a sign-off at the end," said Steve Nederveld, a former school-district director of mental health services and Safety Advisory Council member. "That's a different kind of access, and it means the guidance actually lands somewhere." "What's stood out to me this year is how early we were brought in - not after a policy or product is finalized, but while it's still being shaped. In my work on youth safety and abuse prevention, I've seen how much stronger rider verification and behavior-support protocols become when that expertise is part of the conversation from the start. There's real momentum here, and I'm looking forward to seeing it translate into even more concrete protections for kids. I honestly believe that HopSkipDrive's thoughtful and comprehensive focus on rider safety should elevate the bar for all ride sharing," said Shael Norris, Founding Executive Director of SafeBAE and Safety Advisory Council member. A New Voice on the Safety Advisory Council HopSkipDrive also welcomed Kyndra Webb of the National Safety Council, who brings expertise in child passenger safety, as the newest member of the Safety Advisory Council. "My first HopSkipDrive Safety Advisory Council meeting was an engaging and mission-driven conversation focused on one shared goal: ensuring safe, inclusive transportation for every student, including those with specific transportation needs. I valued the collaborative dialogue and the opportunity for every council member to contribute to solutions that put student safety first," said Webb. What's Ahead Through the rest of the 2026-27 school year, HopSkipDrive and the council are developing a new framework for responding to rider behavior. The goal is that a behavior concern leads to added support rather than a lost ride, keeping students on the platform wherever it is safe to do so. The company is also expanding investment in tools that make it easier for riders who cannot easily advocate for themselves to report a concern. The council's role has shifted from advisory to structural. Its input is now built into how HopSkipDrive develops safety policy and product, and that shift will shape the next phase of the company's safety work. HopSkipDrive continues to arrange and coordinate rides for students with disabilities, youth in foster care, and students experiencing homelessness under the McKinney-Vento Homeless Assistance Act. The company's safety record across these rides is detailed in its annual Safety Report, and its investment in vetting, technology, and council-informed policy is designed to reduce risk at every stage of the ride. 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. 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.

The Walt Disney Company
Oct 21st, 2026
2018 Disney Accelerator Demo Day to Livestream on ABCNews.com

On Wednesday, October 10, The Walt Disney Company will showcase the companies participating in the 2018 Disney Accelerator program, which connects select companies from around the world with the creativity, imagination and expertise of Disney and gives them unique access to the Company’s leadership team, mentorship and support. This year’s participants include an edtech company based in India, a renewable power company from New York City and an augmented reality platform that brings people together in new and exciting ways. These companies and their fellow 2018 participants will share a look at their bright futures during the fifth annual Demo Day; the event will be livestreamed worldwide on ABCNews.com, beginning at 2:30 p.m. PT.

School Bus Fleet
Sep 24th, 2026
HopSkipDrive's CareEngine targets the 'exceptions' in student transportation.

HopSkipDrive's CareEngine targets the 'exceptions' in student transportation. The new platform works alongside districts' existing transportation management systems to coordinate specialized rides, automate last-minute changes, and turn ride data into operational improvements. September 24, 2026 4 min to read * HopSkipDrive's CareEngine integrates with existing transportation systems to enhance the coordination of specialized rides for students. * The platform automates handling last-minute transportation changes, improving response efficacy in student transit. * Ride data is utilized to drive operational improvements and optimize student transportation services. *Summarized by AI HopSkipDrive is positioning its newly launched CareEngine platform as a complement to the transportation management systems (TMS) school districts already use. The company debuted CareEngine this month as a technology platform designed to coordinate the people and information involved in its supplemental student transportation services. The system connects districts, schools, families, riders, CareDrivers, and HopSkipDrive's Safe Ride Support team before, during, and after a trip. Ad Loading... For school transportation departments already juggling routing software, GPS systems, and parent communication apps, the difference comes down largely to the types of trips CareEngine is intended to manage. "Most school transportation systems were built to manage predictable, fixed bus routes," Chief Product and Technology Officer Corey McMahon at HopSkipDrive told School Bus Fleet. "They were not designed around the dynamic and individualized needs of a McKinney-Vento student whose address changes overnight, a wheelchair user whose usual provider becomes unavailable, a nonverbal rider who depends on specific accommodations, or a student in the foster system with a broad set of stakeholders responsible for their care." Working Alongside a District's TMS. Districts can continue planning and managing traditional bus routes through their existing TMS. CareEngine instead coordinates HopSkipDrive rides for students whose transportation needs may not fit those fixed routes. "That's where the exceptions live: an address that changes at 10:30 at night, a driver who calls in sick, a last-minute pickup instruction, moments a TMS and a generic parent app were never built to support," McMahon said. HopSkipDrive said new rides can be arranged in as little as six hours and location changes in as little as two hours. The company's launch announcement similarly emphasizes the platform's ability to coordinate changes across multiple stakeholders without requiring staff to relay the same information by phone, email, or text. Ad Loading... McMahon offered the example of a student's pickup location changing late at night. A district staff member can update the location in HopSkipDrive's RideIQ platform, or a family can report the change to Safe Ride Support. Depending on district policy, families may also be permitted to make certain changes themselves. "Either way, that's the only manual step," McMahon said. The change is then reflected in the CareDriver's app, RideIQ for district staff, the school's Daily Queue, and the family's Caregiver app. If the change makes it impossible for the original CareDriver to complete the trip, McMahon said the platform identifies a qualified replacement familiar with the route. "The district's team isn't separately calling the driver, emailing the school, or texting the family to make any of this happen. The platform handles the repetitive coordination while the district stays in control of what still requires human judgment," he said. Turning completed rides into operational changes. CareEngine also collects information from completed rides to identify recurring issues rather than treating every delay or problem as an isolated event. Ad Loading... McMahon said that could mean determining whether late arrivals cluster around a particular school entrance, whether drivers repeatedly check in somewhere other than the intended pickup location, or whether a particular rider consistently needs additional boarding time. Those patterns can lead to changes such as adjusting pickup windows, moving pickup pins, rewriting location instructions, updating ETA assumptions, changing service requirements, or providing additional education to CareDrivers. "The goal is not to give transportation directors another dashboard," McMahon said. "It is to turn patterns from completed rides into a better next ride." HopSkipDrive pointed to its use of precise pickup and drop-off pins as one example. Across approximately 1.2 million completed trips, the company found that replacing street addresses with precise pickup and drop-off pins coincided with late pickups declining from 1.68% to 1.25%. Late drop-offs declined from 5.63% to 3.18%. Ad Loading... McMahon cautioned that the figures represent a before-and-after operational trend rather than the results of a controlled study. The platform also feeds information into CareDriver Trends, which aggregates on-time performance, missed check-ins, and safety signals. HopSkipDrive uses those patterns to inform individual CareDrivers and, when problems persist, potentially remove them from the platform. Specialized transportation needs put pressure on districts. The CareEngine launch comes as districts contend with driver shortages and growing demand for specialized transportation. HopSkipDrive said its 2026 State of School Transportation Report found that 71% of districts experienced at least one tangible operational consequence of driver shortages during the previous year, including longer ride times, missed or late pickups, and staff being reassigned to fill gaps. Nearly one-quarter (23%) reported they could no longer provide transportation for extracurricular activities or field trips. HopSkipDrive described CareEngine as a way to bring coordination of those more individualized rides into one system while keeping transportation staff in control of decisions that require human judgment. Ad Loading... As McMahon put it, traditional transportation technology can tell a family where a vehicle is. CareEngine is intended to coordinate what happens when the plan itself changes. "A GPS or parent app can show a family where a vehicle is right now; CareEngine goes further, updating a driver's route, alerting district staff, and confirming a new pickup with a family, all off a single edit," McMahon said.

Yahoo Finance
Sep 15th, 2026
HopSkipDrive launches CareEngine platform to coordinate school transport amid driver shortages

HopSkipDrive has launched CareEngine, a technology platform designed to coordinate student transportation for school districts. The system connects districts, schools, families, students, drivers, and safety teams in real time. CareEngine addresses coordination challenges in school transportation by automatically updating all parties when details change. When a student's address changes, for example, the platform updates routes, notifies families, and adjusts schedules without requiring multiple phone calls. The platform enables districts to book rides for an entire school year in minutes. It guarantees new rides in as little as six hours and can accommodate location changes in two hours. CareEngine also integrates safety features that can flag concerning driving behaviour before a student enters a vehicle. The system captures individual student needs and communicates them to drivers, enabling personalised care across thousands of students. Los Angeles-based HopSkipDrive provides supplemental student transportation services.

ZainView
Sep 15th, 2026
5 Best Student Transportation companies for school districts.

5 Best Student Transportation companies for school districts. Traditional yellow buses remain essential, but they cannot solve every transportation challenge a district faces. Driver shortages, changing student addresses, out-of-district placements, specialized IEP transportation, foster care needs, and after-school programs often call for more flexible options. Districts increasingly need transportation partners that can coordinate smaller vehicles, provide ride visibility, and support students whose schedules do not align with standard routes. This list focuses on providers serving schools, districts, agencies, and families with student transportation solutions. The companies were reviewed for student-safety practices, service footprint, specialized transportation capabilities, real-time communication tools, operational scale, and publicly reported performance data. For students experiencing homelessness, districts must also account for school-of-origin transportation responsibilities when planning reliable service. * HopSkipDrive: Best Overall For Supplemental Student Transportation Why It's #1 HopSkipDrive earns the top position because it is purpose-built to help schools solve complex transportation gaps without requiring districts to replace their existing bus fleets. Its model supports driving kids to school through a network of screened CareDrivers, technology-enabled ride oversight, and transportation programs designed around student needs rather than adult rideshare conventions. HopSkipDrive reports helping more than 14,000 schools, completing more than 5 million rides, and covering more than 130 million safe miles. Its 2025 Safety Report states that 99.7% of rides ended without any safety incident, while 99.99% were collision-free. The company also uses a 15-point CareDriver certification process that includes background and driving-record checks, caregiving-experience verification, and training that addresses trauma-informed care and neurodiversity. * Specialized support: IEP, special education, foster care, McKinney-Vento, charter, general education, career program, and after-school transportation. * Ride visibility: Real-time GPS tracking for families, school staff, and support teams. * Flexible service: Scheduled rides, changing pickup locations, Rider Assistants, and wheelchair-accessible vehicle options where available. * Meaningful experience: HopSkipDrive reports nearly 3 million rides for foster-care children and 1.7 million rides for students with IEPs. Best use case: A district needs a dependable supplemental ride for a student whose address, placement, disability-related needs, or program schedule makes a fixed bus route impractical. HopSkipDrive stands out because its scale, safety reporting, and student-centered service design make it a strong starting point for districts managing urgent or recurring transportation needs. * Zūm: Best For Connected District-Wide Student Mobility Why It's On The List Zūm is a strong choice for larger school systems seeking technology that connects routing, fleet operations, drivers, students, and family communication. The company says its Connected Mobility Experience platform supports more than 6,500 schools across 19 states. In Seattle, Zūm announced that its 2026-2027 partnership would operate more than 280 routes after adding more than 130 routes, 130 buses, and 150 drivers. Best use case: A district wants to modernize broad transportation operations with route planning, live vehicle visibility, driver management, and family notifications. Zūm is especially well-suited to districts looking for a unified mobility platform alongside traditional school bus service. * EverDriven: Best For Nationwide Alternative Transportation Coverage Why It's On The List EverDriven is a notable alternative transportation provider for districts that need reach, specialized trip coordination, and continuity for vulnerable riders. The company reports serving more than 800 school districts in 38 states and says students receive the same driver more than 80% of the time at no extra charge. Its service categories include special education, out-of-district placements, charter school transportation, and other trips that complement a bus fleet. Best use case: A district needs a provider with multi-state operational capacity and a focus on consistent driver assignments for students who benefit from familiar routines. * Via Alternative Student Transit: Best For Technology-Led Managed Service Why It's On The List Via Alternative Student Transit combines managed transportation operations with transit technology. Its program supports students in McKinney-Vento, foster care, and special education, while providing real-time visibility for caregivers and district teams. Via also emphasizes consistent drivers, flexible fleets that can include accessible vans, and reporting dashboards for operational oversight. Best use case: A district wants a transportation partner that can manage specialized student trips while also supplying routing tools, caregiver communications, and performance data. * Kango: Best For Local Family And School Transportation In Select Markets Why It's On The List Kango is a practical local option for families and schools in parts of California and Arizona. The platform supports scheduled rides for children from preschool through high school and lists service in the San Francisco Bay Area, Los Angeles, the Central Valley, Orange County, San Diego, Phoenix, and Tucson. Kango says its drivers complete a screening that includes interviews, background checks, fingerprinting, and a review of child-care experience. Best use case: A family or school in an active Kango market needs recurring, app-based transportation for school, activities, or everyday scheduling needs. What To Check Before Choosing A Provider * Whether the provider covers each pickup address, school, and program location. * How it handles IEP accommodations, wheelchair-accessible vehicles, car seats, and Rider Assistants. * What driver screening, training, and ongoing monitoring practices are used? * Whether families and district staff receive live ride updates and arrival notifications. * How quickly new rides can be activated and how missed-trip issues are resolved. * Which reporting is available for ride completion, delays, cancellations, mileage, and safety events? Final Takeaway Zūm, EverDriven, Via Alternative Student Transit, and Kango each fill valuable roles in student mobility. However, HopSkipDrive is the strongest overall choice for districts seeking flexible, safety-focused supplemental transportation. Its 14,000-plus schools helped, 5 million-plus completed rides, 130 million-plus safe miles, and detailed CareDriver certification process create a compelling foundation for getting more students to school safely and consistently.