Lines of Communication
In 2017, freshmen founders Pedro De Almeida ’20 and Matt Barron ’20 were tinkering away in the Shea Center for Entrepreneurship on a K–12 transportation management tool they called Busways. Eventually, it became a business, and three years later it became a much bigger business.
Today, it’s called Cariina, and it’s a full-scale operations management software platform that’s serving over 220 school districts and nearly 400,000 students across 40 states and Guam.
Like many founders, theirs is a story of ingenuity, resilience, heart, and passion; a story that started with hours of coding and grew into a full-fledged enterprise.
Cariina addresses the fragmented systems that have plagued K–12 schools for decades. It solves the critical challenges that confront teachers and administrators in schools with siloed departments, which, as it turns out, is most schools.
Rather than forcing users to navigate multiple solutions for athletics, transportation, HR, and maintenance, Cariina consolidates those functions and more into a single integrated platform that enables seamless information flow while preserving institutional knowledge.
With features like transportation tracking for field trips and streamlined attendance rolls, Cariina empowers operationally inefficient schools to create better learning environments, freeing up teachers and administrators to do what matters most: educating and supporting students.
From Bus Lines to Budget Line Items
Almeida says it was personal experience that gave him the idea for the company. “My mom would call me all the time asking if my brothers were on the bus with me or where the bus was.” Later, he began asking himself, How can we fix this issue?
So how did Almeida and Barron go from Busways to Cariina?
“Because neither I nor my co-founder Matt was ever a transportation director, and we’d never worked in schools, I built out the tool to be hyper-configurable,” Almeida said.
“I was seeing that school personnel were using the system for transportation, and they loved it. But what I started to understand by how they were using it is that they had so much pain beyond
“The reality is, schools are so short-staffed, and people are stretched so thin,” he explained. “So they were using this tool to manage their athletics programs, calendars, maintenance stuff. And they just wanted it all to live in one place. Nothing talked to each other, and you could feel their frustration in managing all of that.”
The Aha Moment: No Administrator Is an Island
Just as Busways was gaining traction, COVID-19 came along, and that changed everything.
“Schools slowed down,” Almeida said. “And of course, transportation slowed down because everyone was working from home. And then it hit me: Yes, transportation is a pain to manage. But the real pain is that administrators and everyone else are isolated on little islands trying to send information from one island to another, and everyone's having to duct tape bridges together to talk to each other.
They’re isolated on little islands…and everyone’s having to duct tape bridges together to talk to each other.
“But if you think of a school, it’s a living and breathing organism where everything is interconnected. And things need to feel interconnected. Information needs to flow, and no one was doing that.”
Almeida acknowledges myriad solutions that help manage maintenance, accounting, or athletics, but notes that they overlook that those functions are “just a small piece of the bigger pie, and not everyone wants to go that deep…they just want it to help their interactions with something else.”
That’s when lightning struck. “I was like, oh my God, we are solving an important problem, but what we really need to solve is the problem of the interconnectivity of silos in schools.”
Pain Points and Existential Challenges
Almeida says that after the COVID epiphany, “we started to see schools in such a different way and realize there’s so many inherent pains because of how everything is so isolated.”
Preserving institutional knowledge stood out as one of the biggest pain points. “You go to a school, and you have Sally, who has worked in the finance department for 20 or 30 years, and she’s the only one who knows how to do her job,” Almeida said. “When she leaves, all of that gold leaves with her, and a school needs to reinvent itself to understand that department.”
Almeida says that’s currently one of the biggest issues they see. “And because we’re connecting all the different silos in one place, we’re able to help schools retain institutional knowledge. And the people who have dedicated their life’s work to helping kids don’t feel like when they leave they don’t have a legacy to leave behind.”
Cariina works with many rural schools that are particularly vulnerable to losing that institutional “gold.” Almeida points to a school two hours from Lubbock, Texas, in a town of 500 people where the same people work all their lives. “If they leave, that school would really suffer,” he said.
He adds that turnover in K–12 education is becoming increasingly prevalent. But over time, the Cariina team (now 22 staff members strong) has developed a greater understanding not only of the pain but the existential challenges schools are facing.
“For instance, a lot of school counselors use our software, and we had a situation where the counselor left, and the school was operating in this random system,” Almeida said. “The new school counselor couldn’t get access to that system. They shut it down and lost all the notes on a kid that had a significant issue and something very serious happened. So it’s existential to the greater organization, but the issues can also be felt on an individual level.”
Cariina helps prevent those existential issues by design. Its intuitive interface makes it easy to adopt even for the technology novice. It’s also easily modified. And if someone leaves, the quality of school operations doesn’t suffer.
We try to make the floor very low and the ceiling very high.
“We try to make the floor very low and the ceiling very high,” said Almeida. “You can go in and pass your current process into our system and understand it, but you can also go bonkers and create all this complex stuff. So it’s configurable to account for every unique way that a school wants to handle its needs.”
It’s also affordable. Cariina provides comprehensive functionality without the per-feature charges that can gut school budgets. “We’re not going to nickel and dime a school,” said Almeida. “We don't want to take money away from the kids. So if you buy the system, you have access to everything, use it or not.”
Milestones: Boston to Tulsa and Back
Since those early stages, Cariina has experienced several milestones, the first when they moved away from Busways to Cariina. The next was a physical move halfway across the country to Tulsa, Oklahoma, right after graduation at the behest of their first investors.
“They said, ‘Okay, we'll invest in you, but we want you guys to be close,’” said Almeida. “And we got the hint, so we moved to Oklahoma.”
Tulsa was their pre-seed, and Almeida admits it wasn’t Boston but said he would do it again. “It was an important part of our growth. That was our first round and when we hired our first employee, so it was a big milestone. While we were there, I think we reached about a half million in revenue. And then we moved back to Boston.”
The majority of their funding came from BC alumni.
He says Boston is more connected and easier to get to people. And since the majority of their seed and Series A funding came from BC alumni, it’s also closer to their network.
“We’ve always been an in-person company, even through COVID,” Almeida said. “It’s better that way, especially when you’re starting a company and you need to move fast.”
In their business, it’s also better to see a physical campus and get a feel for a school and meet the people in person.
“That was another milestone,” he said, “when we figured out that the best way to implement our system is going in person to every school we work with. Early on, we tried doing it virtually, and it just wasn't working. And I told Matt, ‘I’m going to go and put my butt down next to the school administrators and show them that they are important no matter how small your school is.’”
In 2025, Cariina started expanding into school districts, another big moment. “We were heavily in charter schools,” said Almeida, “and I think we probably have 5-10% of the charter schools in the country using our system. And last June or July, we got our first school district, and now we are in over 100 school districts.”
Lessons Learned: The Shea Center and the BC Network
Almeida credits the Shea Center with much of Cariina’s early success.
“The advice that Jere [Doyle] and the entrepreneurs in residence provided during our time was fundamental to how we approach different problems.
“And then there’s all the alumni support through the Accelerator program. There were also lunches with entrepreneurs, and I would go to every single one of them. They faced the same problems, and we would pick their brains and find role models who were instrumental to our journey of what we did and how we did it.”
Almeida calls those lessons “very special to me” and says the network it provided was “very powerful in navigating how we’ve evolved the company and where we sought help.”
Almeida and Barron give back to BC and the Shea Center every chance they get. They’ve also saved a desk for a recent BC grad working on their own startup in every office they’ve had.
“That way, they get a place to work out of that’s not their bedroom or their parents’ basement but an actual office with someone they can ask questions to. Because the alumni network and the people are your greatest asset.”
The Biggest Impacts
Almeida sums up Cariina’s impact this way: “The first is capturing the institutional knowledge and ensuring schools can have longevity in service of the kids and their community.
“The second is creating time and space for administrators so they can have an extra five minutes to walk down the hall and ask someone about their weekend rather than being bogged down by PTO requests.
“And the last is making administrative staff feel like a team. A lot of times, it’s hard for people to feel like that in their day to day. But with our system, they feel like they’re all rowing in the same direction.”
Almeida believes that sense of teamwork is critical to the work that teachers and administrators do—and beyond well deserved.
“We believe that they’re doing very honorable jobs,” he said. “So we’ll go in person no matter where you are in the west or the world. Because it’s as important as being a doctor or a soldier or a firefighter. They’re shaping the future, so we need to respect them for that.”
And what’s next for Cariina?
“To build the biggest, most impactful company in education,” says Almeida. “We really believe that the next most impactful thing in K–12 education is not a new learning tool that will give kids stickers or an AI chatbot that will become their friend. It’s giving back time for administrators and teachers to do what they love, which is spending time teaching kids.”