About HopSkipDrive
What is HopSkipDrive?
HopSkipDrive is a transportation technology company whose stated mission is to "create opportunity for all through mobility". It describes itself as "a technology company that solves complex transportation challenges where there is a heightened need for safety, equity, and care", working on two fronts: a marketplace that connects "kids, older adults, or anyone needing extra support to highly vetted caregivers on wheels", and software, including its RouteWise AI routing product, sold to school districts. Founded "by three moms as a solution to their own transportation challenges", HopSkipDrive supports "over 10,000 schools across the country, as well as nonprofits and government agencies", plus families booking directly. It is a Series D company that has "raised $100M in funding to date".
Where will I work?
Remote-first, within the United States. HopSkipDrive's "headquarters is located in Los Angeles' Little Tokyo district", a space dispersed teams "gather here periodically for moments of collaboration and connection". But the published position is clear: "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." Live job ads bear this out - a recent engineering leadership posting states the role "will be fully remote in one of the following states" and then lists 27 of them. Employees cluster in informal "hubs" of five or more people in cities such as Denver, New York City, Houston and Nashville.
What is the HopSkipDrive team like?
Between 350 and 500 people, organised around six published values: "Safety Is Everything", "Feel It", "Customer First", "Make Tomorrow Better", "Move Fast, Stay Nimble" and "Win Together" - the last defined as fostering "healthy debate" and diverse perspectives while "remembering there's no room for jerks". The company is candid about how much AI has changed the work: "We use AI every day, and not as a productivity add-on. It's woven into how we work at every level." That extends to hiring, where take-home assessments explicitly encourage AI tools. Interviewing runs to five stages for salaried roles and three for hourly ones, including a consolidated panel interview with two to four future teammates.
Work-Life Balance
Time off is published as "Flexible Time Off" - that is the company's own wording, and its job ads say "flexible vacation" - alongside "11 Annual Paid Holidays", a company-wide "Week Closure at End of Year", and "Sick Time Off for You and Family". The remote-first setup is framed around personal commitments rather than desk time, and connection is deliberately engineered: quarterly team events remote and in person, a social committee, Slack communities, remote seasonal parties, and a hub programme funding in-person gatherings where five or more employees live nearby. HopSkipDrive does not publish a four-day week, a 32-hour week or any compressed-hours schedule.
Perks and Benefits
- Medical, dental and vision cover, plus a health spending account and FSAs
- Mental health resources and an employee assistance programme
- Short- and long-term disability insurance, plus life insurance
- Paid parental leave
- Company ownership: job ads state "every full-time employee has equity"
- 401K plan
- Professional development and learning stipend
- Home internet reimbursement for remote work
- Flexible Time Off plus 11 annual paid holidays and an end-of-year week closure