HopSkipDrive Company Culture & Values

How would you describe your company’s approach to remote-first work? What have been the greatest successes thus far and what obstacles have you overcome in building a remote team?

Our remote-first model is built on flexibility and trust. We believe the best talent is everywhere, so we hire nationally to bring diverse perspectives to our work. We’re headquartered in Los Angeles and support employees in over 30 states. This broad reach is key to our success: it ensures our internal team is as geographically and demographically diverse as the population of schools, riders and caregivers we serve, as well as the community of CareDrivers who work with us. We offer a hybrid option for Los Angeles-based employees and many teams host annual in-person gatherings to strengthen connections, but our baseline is remote.

How does your team stay connected in a remote-first office? Are there specific tools you rely on to communicate and collaborate together?

Slack is the central hub for all our team communication, both for collaborative work and informal conversation. We have a variety of popular channels that go beyond project tasks, like #hopskipdogs, #hopskipparenting and #hopskipfoodies, as well as niche groups such as #hopskiplego and #hopskipspooky. This variety helps people genuinely connect on a personal level.

To ensure employees can meet colleagues outside of their immediate teams, we use Donut, a tool that randomly pairs people for casual virtual coffee chats. We also use a tool for peer recognition, which is a simple and public way to celebrate great work across the organization. For video calls and team meetings, we primarily use Google Meet or Zoom.

How does your company build culture in a remote-first office? What specific rituals or initiatives does your team use to create a more inclusive, engaged environment?

We build a strong remote-first culture through a combination of company-wide traditions and team-level initiatives. Our primary company tradition is the bi-weekly all hands we call Town Hall, which ensures everyone stays connected to organizational updates. A favorite segment is “Shoutouts & Gratitude,” where team members can publicly thank a coworker and share something they’re personally grateful for outside of work. We also encourage colleagues to give voluntary presentations (similar to Show & Tell) to share their hobbies, memorable experiences or community involvement.

To foster local connections, we run a “hub program” that gives any metro area with at least five employees a dedicated Slack channel and a quarterly budget for local events like dinners or bowling. 

We also prioritize inclusivity by celebrating cultural holidays with themed virtual events, such as a Diwali escape room or Black History Month trivia. To cap off the year, we host annual virtual holiday parties, featuring hands-on classes.

How does HopSkipDrive help team members recharge during the holiday season?

Our company prioritizes our team members’ well-being, especially during the holiday season. To help everyone recharge, we close between Christmas and New Year’s, giving all employees a well-deserved break to rest and spend time with loved ones.

Additionally, we’ve hosted wellness workshops focused on managing burnout, equipping our team with tools to maintain balance. During the holidays, we also embrace the festive spirit with thoughtful company gifts and vibrant interest groups on Slack. For example, our crafting Slack channel group organizes holiday ornaments exchanges, fostering a sense of community and fun. These initiatives reflect our commitment to creating a supportive and joyful environment for our team.

Why is this support important from a work-life balance perspective?

This support is vital from a work-life balance perspective because it ensures that team members have dedicated time to step away from work, recharge, and focus on personal well-being during a season that can be both joyful and demanding. Closing the office between Christmas and New Year’s guarantees everyone can rest and spend meaningful time with loved ones without work pressures. Hosting wellness workshops on managing burnout gives employees practical strategies to maintain balance during the holidays and throughout the year.

Holiday initiatives like company gifts and engaging Slack group events, such as the baking group’s cookie exchange, foster connections and create moments of joy beyond work responsibilities. These efforts help cultivate a culture where employees feel personally and professionally supported, reinforcing the importance of balance and overall well-being. In the long run, this kind of support encourages sustainable engagement, productivity and happiness and assures a promising future for both the individual and the organization.

What kind of feedback has your team received regarding this support during the holiday season? How has it positively impacted employees?

We’ve received overwhelmingly positive feedback from employees about “HopSkipHoliday.” Many have shared that a synchronized break ensures no work piles up in their absence, significantly reducing stress. Employees have also expressed appreciation for the opportunity to be more present during the holidays, which allows them to fully enjoy time with loved ones, including more space to travel to those who live far away. These sentiments highlight how HopSkipHoliday supports work-life harmony, a key value we hold dear, and encourages meaningful contributions outside the workplace.