HopSkipDrive Innovation, Technology & Agility

What’s your professional or academic background? How did you break into the tech industry?
I started my career as an eighth-grade math teacher, teaching at a magnet school for English learners, where I quickly developed an appreciation for effective student transportation: Buses were critical for my students’ commute to school.

My classroom experience sparked a desire to contribute to systemic change within the K-12 education system. After a period of growth as a management consultant, I returned to Denver Public Schools to lead district strategic planning and voter initiatives.
As Denver Public Schools’ first operations chief of staff, I managed complex districtwide initiatives, including a significant bell time change to facilitate later high school start times. This experience highlighted the impact of data on effective student transportation, prompting me to seek opportunities in the edtech space.

With this background, I joined HopSkipDrive to lead the development and scaling of RouteWise AI, the first transportation intelligence platform. RouteWise AI empowers districts with strategic insights into current operations and optimized transportation plans that solve districts’ critical challenges such as budget cuts and driver shortages.

How did you learn how to use AI, and how do you apply it to your work?
My journey in AI has been self-taught and greatly influenced by my peers.

With our RouteWise AI model, we utilize a machine learning algorithm that evaluates millions of calculations and thousands of scenarios to create optimal transportation plans. This has been a valuable experience alongside our engineers and product managers, as we continually adapt to new constraints and district needs. In addition, I listen to podcasts such as AI Explained and subscribe to various newsletters like The Information. I also discuss new features and innovative uses of AI with my team and I stay up to date with the latest developments through HopSkipDrive’s AI Ambassadors program, which empowers employees to become leaders by connecting them with a network of experts and creating space for their innovations.

AI provides me with tools that drive tangible benefits, such as using AppScripts to integrate new data sets, employing a research assistant to streamline insights from our sales meetings and utilizing a custom tool to draft new marketing materials and reports on sales prospects.

What do you consider the greatest benefit of leveraging AI? How has it positively impacted the work you produce as a whole or your career?
The greatest benefit of leveraging AI in student transportation is its ability to unlock previously unthinkable analyses and optimizations that directly benefit students and school districts. It’s about moving beyond simply identifying problems and truly finding comprehensive solutions.
At HopSkipDrive, we see this impact firsthand. Our proprietary AI and machine learning technology doesn’t just rearrange a district’s existing vehicle assets; it analyzes the entire transportation landscape to deliver optimized transportation plans and always-on insights into current operations. This has impacted the work we produce and, by extension, the operational efficiency and budgetary health of school districts.

For example, with a district partner in West Virginia, RouteWise AI has evaluated over 400 different scenarios, allowing for effectively balancing competing variables in transportation such as bell times, student commutes and budget needs. Previously this work would have required months of manual calculation. By using AI, we can provide solutions in hours. I am excited to expand this offering, as it saves school districts money and enhances student access to education.

Tell us about your tech stack. What tools do you use to gather and organize data, and which tools do you rely on most in your daily work?

Using technology and leveraging our tooling empowers me and my colleagues to best serve our customers. As an organization, HopSkipDrive recognizes that investment in technology and tools is ultimately an investment in its employees and our customers.

On a daily basis, I use Salesforce as my CRM tool and my primary source for information on accounts, ride adoption, renewals and the sales pipeline. I also rely on Tableau dashboards for real-time analytics to identify trends. Beyond these foundational tools, we’re always exploring and implementing new technologies for uses like meeting summaries and AI-powered workflows to enhance our collaboration and efficiency. This commitment to a tech-forward environment helps us track performance effectively, respond proactively and ensure that every client conversation is informed by data. It’s an approach that supports both our team and our customers.

How has data helped you close a deal?

Data is a critical tool for understanding what a prospective client needs and helping explain how we can solve their challenges. I share relevant data with school districts, nonprofits and government agencies as tangible demonstrations of how a partnership with HopSkipDrive will bring safe, reliable rides to students. During a recent renewal conversation with a larger school district, I used data to showcase our reliability and consistency by pulling reports that showed our on-time performance for rides to and from school. This tangible data served as real-life examples of our consistency and reliability, giving the client added confidence in our service and associated commitment to helping them solve important problems they navigate daily. 

As a result, it shifted the conversation from a general discussion to a value-focused one. This ultimately helped the client to better understand the value that HopSkipDrive provides, encouraging them to continue our partnership and even increase utilization of the unique value we provide: support in optimizing budgets, improving access to transportation by creating safer rides for more students.

How does sales and customer data enhance HopSkipDrive’s sales org? What data do you find most important in the sales process?

Sales and customer data are essential for maintaining and enriching our partnerships. Data that demonstrates value, such as on-time performance, which measures the percentage of rides that arrive at school or appointments on schedule, helps build trust. Adoption, forecast and projection data are equally important because they reveal untapped opportunities for expansion into markets where our services could create more access to transportation. Because our Customer First value is so important, we also analyze data to understand each client’s evolving transportation needs. This allows us to proactively engage with them, identify new opportunities to support their goals and direct our efforts where they will make the greatest impact for the client. By utilizing both value metrics and forward-looking data, we can ensure we’re delivering the best possible service and fostering long-term, successful partnerships.

What practices does your team employ to foster innovation, and how have these practices led to more creative, out-of-the-box thinking?

At HopSkipDrive, I am part of the RideIQ team, which develops a platform for school district partners to manage transportation for their students. Our team culture fosters innovation, allowing me to try new things, take risks and swiftly adjust when something doesn’t go as planned. It gives me the freedom to experiment and iterate without fear.

I’ve felt encouraged to explore new ideas and take ownership when I spot opportunities for improvement. Innovation is also openly celebrated. We highlight wins in Bonusly, our employee recognition tool, as well as dedicate time for shoutouts in our engineering all-hands. Additionally, we hold weekly internal events, such as Dev Gym, which is a meeting where we learn, explore and brainstorm about processes for the engineering team. Once a year, we also hold a companywide hackathon, which is a great space for us to learn from one another and build on each other’s creativity. There’s a contagious energy that comes from watching your teammates succeed and creating a supportive environment where we all push each other to excel. Curiosity is encouraged, and our efforts are valued, even when things don’t pan out.

How has a focus on innovation increased the quality of your team’s work?

I believe that passionate people build better products. When you know your ideas are supported, you naturally care more about how they’re executed. That pride in ownership shows in the final result. Because of that, we’re not afraid to hold off on releasing something if it needs more polish. We regularly check in with each other about what’s working and what’s not, and we’re not afraid to trim features that feel clunky or forced. That level of honesty helps us deliver better experiences, not just more features.

We are also quick to adapt to new tools. For example, we recently overhauled our internal component library to learn from, and model patterns used by, leading startups. We use modern web development frameworks like React and Rails and keep up with advancements and new features. As a result, we now have smoother workflows and more scalable code.

How has a focus on innovation bolstered your team’s culture?

One of my favorite aspects of this job is the culture. Everyone is curious, supportive and excited to build cool things together. There’s no ego or rigid hierarchy — just a shared commitment to HopSkipDrive’s mission to create opportunity for all through mobility. We focus on solving transportation challenges that require safety, equity and care by providing educators with supplemental student transportation from high-vetted caregivers and industry-leading routing software that help our kids get to and from school safely, reliably and on time.

Trust runs deep within the team. When someone has a new idea, the response is almost always, “Sounds great, go for it!” That kind of support encourages initiative and makes it easy to believe in each other’s strengths. Collaboration is easy because everyone’s voice is heard. Bouncing ideas off teammates has taught me a lot, making even tough challenges manageable. Innovation doesn’t feel like pressure — it feels natural.