Leveraging education expertise to shape HopSkipDrive’s RouteWise AI™

HopSkipDrive is committed to revolutionizing the landscape of school transportation by introducing innovative solutions that speak directly to the needs of school transportation teams, districts — and, of course, students. 

Central to our strategy is recruiting team members with substantial backgrounds in the school transportation and education sectors. Through this approach, we aim to ensure the development of our products — especially HopSkipDrive’s RouteWise AI™ — is student-centric and aligned with the nuanced needs and day-to-day realities of districts and school transportation teams.

We are proud to highlight two team members with exemplary expertise in the education space — one who has managed district operations as Chief of Staff, and another who has worked as a Director of Transportation. As the Director of Software & Advisory at HopSkipDrive, Dustin Kress is overseeing the growth of RouteWise AI. Greg Dutton, a Transportation Analyst at HopSkipDrive, builds optimized routing plans for clients across the country. 

In consultation with school transportation leadership, RouteWise AI utilizes artificial intelligence-powered machine learning to create the “first draft” of a district’s routing plan, which can then be reviewed, adjusted, and implemented seamlessly by the routing team.  

Read on to learn more about Greg and Dustin, and how they’re applying their backgrounds to their work at HopSkipDrive.

Navigating transportation challenges through real-life experience

Dustin KressIn addition to the two years he spent working as a teacher, Dustin Kress, HopSkipDrive’s Director of Software & Advisory on the Growth & New Verticals team, has a wealth of relevant knowledge and experience — much of which he gained during his tenure as Chief of Staff to the COO at Denver Public Schools, where he led the operations leadership team including finance, technology, food services, facilities, and transportation. Dustin rolled up his sleeves to collaborate on managing the district’s transportation system during Covid, and has a deep understanding of the increasing obstacles and difficulties involved in getting students to and from school during, and after, the pandemic.

“I worked very closely with Denver Public Schools’ Executive Director of Transportation to redesign the system three times: once for social distancing, a second time for relaxed social distancing with a bus driver shortage, and the third time to revise district-wide bell times in response to the driver shortage,” relays Dustin. “I think I bring an ability to work with and support districts based on my own understanding of the demands that are put on them from the community, from their team, and from district leadership.”

Greg DuttonGreg Dutton brings a uniquely informed perspective to his role as a Transportation Analyst at HopSkipDrive. Having first engaged with HopSkipDrive on the client side during his tenure as the Director of Transportation at Renton School District in Washington State, Greg has a deep understanding of the daily struggles and tough decisions facing school transportation professionals — including issues related to the national school bus driver shortage.

“I started at Renton in 2019, so I was there during the pandemic and post-pandemic when getting school bus drivers really became a problem. Despite being very creative with hiring practices, training, and onboarding new drivers, it was a constant struggle,” Greg reports. “It was really about trying to balance everything from a financial perspective as well as a resource and daily operations perspective. Your main focus is to get everybody to school. And once you’ve gotten them to school, you then spend hours trying to figure out how to get everybody home with the same limited resources.”

Tech-driven solutions for complex routing issues

HopSkipDrive’s RouteWise AI analyzes a school district’s complete transportation landscape — including the student base and available vehicles, as well as district-specific needs and preferences — to deliver customized routing options, scenario plans, and recommendations to meet each district’s unique goals. Routing plans generated by RouteWise AI are designed to match the reality of each district’s on-the-ground experience, and solve for priorities like bus driver shortages, shifting bell times, budgetary constraints, and more. 

Based on their firsthand experience of district and school transportation operations, Greg and Dustin both believe that technology solutions are an absolute necessity in aiding districts with navigating evolving challenges. This is especially true when dealing with traditional routing methods, which can be limited when it comes to adapting to dynamic situations. 

By working to bridge the gap between district strategy and operational feasibility at Denver Public Schools, Dustin realized that districts are not always fully equipped to handle the complicated routing demands that transportation teams are forced to react to on a daily basis. “I brought the political requirements and district strategy angle, and then worked closely with the transportation team to understand what would actually work operationally. Doing so was very time-consuming and manual — a lot of paper and pencil and kind of best guesses, along with uncertainty about what it would actually look like if we activated it,” he explains. “Districts can no longer just roll over last year’s routing like they were able to in the past. They need support so they can step back and rethink in a bigger, different way. And that’s where HopSkipDrive comes in.”

The opportunity to work on improving routing operations using technology at HopSkipDrive was an exciting prospect not only for Dustin but also for Greg. Prior to his role at Renton School District, Greg worked as a Transportation Technician at another school district in Washington — Snoqualmie Valley School District — where he handled routing, dispatch, and occasionally covered as a bus driver.

“With routing, it’s often about not having the right tools available. It’s not something you can do on paper, you can’t do it in your head, and most of the transportation management systems that are on the market today don’t do it to the level of complexity that you really need,” Greg says. “You can make small changes to bump up efficiency but in instances where you have to make a bigger change — like when you have a bus with 90 kids, and that’s too many to fit on the bus — you have to get creative. RouteWise AI offers the chance to do so by allowing for a quantum leap with technology.”

From data to reality: Shaping effective student transportation 

When talking about the tech-forward approach of RouteWise AI, Greg likens it to a giant jigsaw puzzle, “one where you get to design what all the pieces look like. You leverage the algorithms and technology to figure out how to put all of these pieces together and arrange them so they create a cohesive picture — one that makes sense to everyone and is going to actually work in reality.”

While working as Chief of Staff at Denver Public Schools, Dustin reports that he often felt like he was the one bringing extra demands to the transportation team with things like changing bell times or new populations. Because of this, he feels he has an informed perspective on how RouteWise AI can support a transportation team in getting ahead on strategy. 

“We know from our work with our initial RouteWise AI pilot cohort that a flexible approach to transportation that is focused on matching students with the best vehicle combined with the optimized use of buses and drivers can address the driver shortage,” says Dustin. “One district using RouteWise AI was, in fact, able to afford a meaningful raise for their drivers while still operating budget neutral by moving some under-utilized bus stops to sedans. As a supplement to school transportation systems, HopSkipDrive can help to make everything work better for the school transportation teams themselves.”

Seasoned expertise: The backbone of the HopSkipDrive team

Both Greg and Dustin acknowledge the critical link between their prior experiences and their roles at HopSkipDrive, affirming the importance of understanding the intricacies and challenges of school transportation when crafting innovative solutions. “With my background, I don’t need an explanation on how everything works,” claims Greg. “Even though things can operate a little differently on this side, at the end of the day, the core factors are all the same. And it’s great being on a playing field where I know all the rules, and I know how the game works.”

Dustin agrees with this sentiment and also emphasizes the ultimate end goal of all of the work we do at HopSkipDrive: the well-being and satisfaction of clients, Riders, and families. “With RouteWise AI, we’re bringing not only a technology solution but also an understanding of how that impacts all of the people involved in the ecosystem.”

HopSkipDrive is committed to helping districts move beyond day-of decisions made on the fly out of necessity, such as eliminating routes and canceling services. These approaches don’t really work in the long run, and they also have unintended negative impacts on the social and emotional well-being of students. 

“That’s exactly what we don’t want to happen,” says Dustin. “We know there isn’t always an easy solution. But we have an amazing product with HopSkipDrive’s RouteWise AI, and we’re already seeing win-win results where it’s working better for districts. It’s working for the driver shortage, it’s working for students, it’s working by helping to get all students to and from school on time. I’m just so glad to have the opportunity to bring this type of solution to what I know from personal experience is a really challenging space.”

As we continue to build a team equipped with education and school transportation backgrounds, we believe we can make a pivotal shift in addressing the multifaceted challenges faced by schools and districts today. Through our collective experiences, expertise, understanding, and empathy, everyone who is part of the HopSkipDrive team is dedicated to ushering in an era of optimized, technology-driven transportation solutions that prioritize district efficiency and student welfare.

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