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The official CEO.com podcast featuring unfiltered conversations with the leaders shaping our world.
Clint Betts: Joanna, thank you so much for coming on the show. You’re the co-founder and CEO of HopSkipDrive. What is HopSkipDrive?
Joanna McFarland: HopSkipDrive is a student transportation solution. We help school districts supplement traditional yellow school buses to make sure all students have reliable access to school.
Clint Betts: How did you first realize this was a problem that needed solving?
Joanna McFarland: Originally, we were trying to solve a slightly different problem.
Honestly, we felt like terrible working moms.
I was working full-time and have two kids. One of my children wanted to go to karate at three o’clock on a Thursday afternoon, and I had no way to get him there. I didn’t need a nanny and couldn’t afford one. I literally needed someone to help for about 20 minutes a day.
I connected with two other women. Between us, we had eight kids, and we were all struggling with the same challenge. We felt there had to be a better solution.
So we created HopSkipDrive as a rideshare platform specifically designed for children. We built a network of highly vetted drivers we call CareDrivers and created an entire system around trust, safety, and technology.
As we grew, we realized that K–12 transportation is a massive industry. More than $30 billion is spent annually on student transportation in the United States, yet the system hasn’t changed much in decades.
The traditional model relies almost entirely on a 72-passenger school bus as a one-size-fits-all solution. But education has changed, transportation needs have changed, and families have changed.
We believed schools needed multimodal transportation options—buses, vans, and cars working together—to create a more flexible and efficient system.
That’s really what HopSkipDrive has become.
Clint Betts: So in some ways, it’s like Uber for school transportation?
Joanna McFarland: I usually avoid that comparison.
We are licensed similarly to Uber and Lyft as a transportation network company, and we do operate a large network of independent contractors.
But that’s where the similarities end.
From the beginning, we designed the platform around one key difference: the person riding in the vehicle is not the person who booked the ride.
Kids are more vulnerable. They may not have a phone. They may not be able to advocate for themselves.
So we built everything around a simple question: “What would I need to see before putting my own children in a HopSkipDrive ride?”
That starts with the drivers.
All CareDrivers must have caregiving experience. On average, they have about 10 years of caregiving experience. These are people who already work with children and understand how to interact with them safely and responsibly.
We also conduct background checks, fingerprint checks, vehicle inspections, video interviews, and a 15-point screening process that goes beyond typical rideshare requirements.
Then we built what we call Safe Ride Technology.
Every ride is monitored live in real time. Our Safe Ride Support Team watches trips as they happen.
If a driver is running late to pick up a child, that’s not just an inconvenience—it’s potentially a safety issue because that child may be waiting alone.
Parents, caregivers, and schools have complete visibility into every ride. They know who the driver is, where the child is, and exactly what’s happening throughout the trip.
Most school transportation systems still don’t provide that level of visibility.
With HopSkipDrive, they do.
Clint Betts: As a parent, that’s incredible.
I have four kids, and my youngest has special needs. Transportation is a huge issue. We actually had to send him to a school outside our normal district, and they offered bus transportation, but he would have been on the bus for nearly five hours every day.
That just wasn’t workable.
Joanna McFarland: Exactly.
And is a child going to arrive calm, regulated, and ready to learn after spending that much time on a bus? Probably not.
That’s where services like ours can truly change a family’s life.
Clint Betts: At what point did you realize you were really onto something?
Joanna McFarland: One of the first major breakthroughs came through foster care transportation.
Federal law gives foster youth the right to remain at their school even if they’re moved to a new placement.
Think about what those kids experience.
They may be removed from their home late at night, moved to a completely different community, and lose almost every source of stability in their lives.
School may be the one stable thing they still have—their friends, teachers, and support system.
But transportation becomes a huge challenge.
A child might move 45 miles away overnight. A school bus system can’t suddenly reroute itself for that one student.
HopSkipDrive can.
A county employee in Los Angeles who used our service for her own daughter recognized this and introduced us to the child welfare system.
That was when we realized there was a much larger opportunity.
Today, many of the students we serve are among the most vulnerable:
Foster youth
Students experiencing homelessness
Students with special needs
These populations often need transportation solutions that traditional bus systems struggle to provide.
Clint Betts: How many school districts do you serve now?
Joanna McFarland: About 700 school districts across 17 states, and we continue to grow.
Clint Betts: That’s incredible.
What does a typical day look like for you now?
Joanna McFarland: Every day is different.
At any given time, we have tens of thousands of students being transported. We also have about 350 employees.
Early on, I used to joke that I had done every job in the company.
Now I joke that I couldn’t do most of them anymore because the company has evolved so far beyond those early days.
My role today is largely about communication, context, and alignment.
Making sure employees understand priorities.
Making sure clients have what they need.
Making sure CareDrivers have the support they need.
And helping everyone understand how their work contributes to the larger mission.
There’s a lot of context switching.
Clint Betts: How is AI changing the business?
Joanna McFarland: AI is opening up tremendous opportunities.
One of our biggest AI initiatives is RouteWise AI.
RouteWise helps school districts optimize transportation planning.
A district can upload its transportation data, and RouteWise can evaluate hundreds of thousands of possible scenarios within minutes.
For example:
Adjusting school bell times
Reducing transportation costs
Solving driver shortages
Improving route efficiency
Reducing student ride times
We’ve had situations where school boards proposed a schedule change and RouteWise showed it would cost an additional $2 million annually.
Then RouteWise generated several alternative options that achieved the same goal at no additional cost.
That’s incredibly powerful for transportation directors and school administrators.
Internally, we’re also using AI to automate operational work, reduce repetitive tasks, and allow employees to focus on higher-value activities.
For us, AI isn’t about replacing people.
It’s about helping people focus on the work that matters most.
Clint Betts: How have you funded the company?
Joanna McFarland: We’re venture-backed.
We raised money when we were still focused on the consumer market, then raised additional capital when we pivoted toward school districts.
Then COVID hit.
Honestly, the business almost died.
Schools closed, transportation stopped, and our entire business model was disrupted.
We had to make extremely difficult decisions, including laying off more than half the company.
One thing I’m proud of is that as we recovered, we were able to rehire more than a third of those employees.
We always believed schools would eventually reopen.
What we didn’t know was when.
But we knew the transportation challenges we were solving would still exist—and in many ways would become even worse.
That turned out to be true.
Driver shortages intensified.
Student transportation needs increased.
And chronic absenteeism became a major challenge nationwide.
Clint Betts: The statistic that really jumped out at me was that 11% of parents have lost a job opportunity because of transportation challenges.
That’s enormous.
Joanna McFarland: It really is.
Transportation impacts much more than getting from Point A to Point B.
It impacts education.
It impacts workforce participation.
It impacts economic mobility.
For many families, especially single-parent households, transportation can be the difference between opportunity and limitation.
That’s why we believe this work matters.
Clint Betts: It’s remarkable what you’re building.
How do you think about leadership?
Joanna McFarland: We’ve always been a mission-driven company.
Initially, the mission was very personal: helping families like mine.
Over time, we discovered an even larger problem to solve.
Everything starts with access.
Transportation is really about access to opportunity.
That belief drives our culture.
One of our core values is what we call “Feel It.”
We want people to have empathy—for students, families, schools, drivers, and colleagues.
Our other foundational value is “Safety Is Everything.”
Every decision ultimately comes back to those principles.
Clint Betts: We end every interview the same way.
At CEO.com, we believe the chances one gives are just as important as the chances one takes.
Who gave you a chance that helped get you where you are today?
Joanna McFarland: I’ve been fortunate to have many mentors throughout my career.
But what stands out most are the people who trusted me before I was fully ready.
They gave me opportunities that were beyond my experience level.
They put me in situations that were uncomfortable and challenging.
They allowed me to learn, make mistakes, and grow.
Those opportunities shaped my career more than anything else.
Clint Betts: That’s incredible.
Joanna, thank you so much for coming on the show. What an honor to have you.
Joanna McFarland: Thank you so much for having me.