Full-Time
Legal Operations Manager
Posted on 10/3/2025
HopSkipDrive
501-1,000 employees
Safe child transportation via vetted drivers
Compensation Overview
$100k - $125k/yr
New Mexico, USA + 27 more
More locations: Washington, USA | Kansas, USA | Oregon, USA | California, USA | Washington, DC, USA | Texas, USA | Jackson Township, NJ, USA | Florida, USA | Nevada, USA | South Carolina, USA | Georgia, USA | Arizona, USA | Tennessee, USA | Virginia, USA | Minnesota, USA | Colorado, USA | Utah, USA | New York, NY, USA | Maryland, USA | Wisconsin, USA | Massachusetts, USA | North Carolina, USA | Oklahoma, USA | Missouri, USA | Michigan, USA | Illinois, USA | United States
Remote
This role will be fully remote in one of the following states: AZ, CA, CO, DC, FL, GA, IL, IN, KS, MA, MD, MI, MN, MO, NC, NJ, NM, NV, NY, OK, OR, SC, TN, TX, UT, VA, WA, WI.
 Legal & Compliance (2) |
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- 5+ years of experience in a legal operations role, legal or policy support role, project management, or a similar operational function within a legal department or law firm
- Familiarity and proven experience working directly with Revenue and/or Sales and Finance teams to implement and adapt contract best practices
- Exceptional organizational skills and attention to detail, with a strong ability to manage records and maintain accurate information
- Expertise in creating visually appealing and compelling company presentations with Google slides
- Demonstrated experience in streamlining workflows, identifying inefficiencies, and implementing process improvements
- Prior experience exploring opportunities for – and ideally successfully implementing – AI efficiencies into legal workflows and/or contract management
- Proven ability to manage complex work streams and prioritize tasks effectively
- Strong familiarity with legal technology solutions, including contract lifecycle management systems, document management systems, and legal inquiry/ticketing systems
- Excellent data analysis skills and experience in generating reports and dashboards
- Excellent written and verbal communication skills, with the ability to interact effectively with legal professionals, cross-functional teams, and external partners
- Streamline workflows, identifying inefficiencies, and implementing solutions to optimize legal and policy operations
- Manage the workflow and completion of legal requests through internal inquiry system
- Oversee back of house legal and policy operations, including record keeping and contract lifecycle management system
- Produce monthly legal and policy teams data for leadership reporting through analyzing existing metrics and the creation of new metrics to best demonstrate the team’s performance
- Support team functions through legal and policy team project management and support, vendor and outside counsel management, and continuing education facilitation
- Influence improvements through identifying problems, gathering information, and encouraging changes to work behaviors to achieve optimization
- Demonstrate deep curiosity about – and/or experience with – AI in legal workflows, and a willingness to explore the implementation of AI tools as well as drive associated internal adoption
- Maintain and update legal playbooks including contract playbooks
- Prioritize cross functional partnerships and collaboration with teams including Revenue Operations, Finance, Sales on projects including – but not limited to – contract management updates, and building systems to support increased contract volume and contract best practices
- Spearhead change management of tooling, driving adoption of new technology and processes
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
Simplify's Take
What believers are saying
- School bus driver shortage persists, increasing district demand for supplemental transportation services.
- Flexible Invoice Groups automates complex billing across multiple funding sources, reducing administrative burden.
- Ride Recording: In-App and Track My Ride enhance safety positioning, strengthening district contract retention.
What critics are saying
- School district budget cuts reduce supplemental transportation spending as districts prioritize core services.
- Established logistics firms enter market with lower-cost fleet infrastructure, undercutting HopSkipDrive pricing.
- Gig-economy reclassification forces CareDriver employment status change, eliminating flexible cost model advantage.
What makes HopSkipDrive unique
- Direct CareDriver relationships eliminate middleman markups and fragmented data versus unregulated brokers.
- Specialized focus on McKinney-Vento, foster care, and IEP students addresses underserved market segments.
- RouteWise AI platform provides multimodal routing and budget alignment automation for districts.
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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
↑ 1%1 year growth
↑ 2%2 year growth
↑ 5%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.
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.
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
HopSkipDrive elevates safety standards with new CareDriver Education Programs and enhanced certification process. New Initiative Deepens Commitment to Safety Acrossthe Entire CareDriver Lifecycle, from Pre-Certification to On-Platform Education LOS ANGELES, Calif. - HopSkipDrive, a technology company solving complex transportation challenges for more than 13,500 schools, today announced key enhancements to its industry-leading safety program. The company has launched a strengthened educational curriculum for CareDrivers, developed in partnership with child development experts, and will be rolling out a more sophisticated, skills-based CareDriver certification process to offer enhanced support for all students, including those with diverse needs and Individualized Education Programs (IEPs). This dual investment raises the industry bar by shifting from fixed quantitative requirements to a more thoughtful, qualitative assessment of a candidate's caregiving capabilities. As part of the HopSkipDrive 15-point certification process, this skills-based video screening moves beyond fixed requirements to a more meaningful evaluation of a candidate's situational judgment, empathy, and readiness to work with children. Because HopSkipDrive maintains a direct relationship with the CareDriver community, the company is uniquely positioned to implement these higher standards for screening and ongoing education, contributing to its industry-leading safety and compliance record. In parallel, HopSkipDrive has launched new educational modules designed to provide CareDrivers with leading-edge skills to support neurodivergent riders. The curriculum was developed in partnership with Jenifer Eaton, MA, BCBA and Timothy Humphrey, M.S.Ed., BCBA, of Rooted in Play, as well as Steve Nederveld, former Director of Mental Health for Cherry Creek Schools. Eaton and Nederveld also recently joined HopSkipDrive's Safety Advisory Council. The program focuses on understanding sensory sensitivities, de-escalation techniques, and communication strategies. "Safety and trust are the foundation of everything we do, and this evolution of our programs represents a deeper commitment to those values. We know that being a great caregiver starts with prior experience, and is further developed with the resources and education HopSkipDrive provides once CareDrivers are on the platform," said Jen Brandenburger, SVP of Safety at HopSkipDrive. "By pairing a more intelligent, skills-based certification process with expert-led continuing education, we can help ensure CareDrivers are exceptionally prepared to support every child. This holistic approach raises the standard for the entire student transportation industry and reinforces our commitment to being the most trusted partner for schools and families." The new initiative reflects HopSkipDrive's dedication to providing the most empathetic and effective specialized transportation solutions, built upon a foundation that includes trauma-informed care education, Child Abuse and Neglect screenings, and three types of rigorous background checks. "A safe, positive ride to school plays a crucial role in a student's overall success and that begins with a prepared, empathetic adult behind the wheel," said Jenifer Eaton. "HopSkipDrive's commitment to helping CareDrivers better understand trauma-informed practices and the unique needs of neurodivergent students is truly invaluable. By equipping CareDrivers with these insights and strategies, we're building a more compassionate and responsive system, one that ensures every student is supported with the patience, understanding, and respect they deserve." The new education modules are now available to all CareDrivers on the platform, and the enhanced certification process will begin rolling out to new applicants over the coming weeks. About HopSkipDrive HopSkipDrive is a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care. HopSkipDrive 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 13,500 schools across 17 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.
School districts such as Tolleson Union High School District in Arizona have already partnered with HopSkipDrive to optimise their transportation networks.