Co-founder Mike Sheldon discusses how the company’s servant leadership model drives a culture of collaborative problem solving, talent development, and customer-centric software solutions.
At Red Rover, pushing the boundaries of K-12 workforce technology is only part of the mission. For Mike Sheldon, co-founder and Chief Technology Officer, creating solutions that make a real difference is equal parts about the craftsmanship of the product and the people who helped build it. With a lifelong passion for building and a practical, problem-solving approach, Mike is dedicated to turning Red Rover’s software into a valuable and indispensable tool for schools nationwide.
In this interview, Sheldon reflects on his journey from childhood entrepreneur to tech innovator and the spirit of collaboration that makes Red Rover’s software a trusted solution among K-12 districts. Sheldon offers a glimpse into the thought and dedication behind Red Rover’s success, from building a talented and driven team to leading by example through servant leadership.
How do you balance your personal life with the creativity and focus it takes to develop software?
I have two boys who take up most of my free time. But when it comes to starting and running a business, my mind is always going on Red Rover — even when it’s not. To unplug, I like to play pick-up basketball, and if I ever get a chance to go skiing, I’ll be out on the mountain.
I’m the oldest of three brothers, and my middle brother is definitely the artist or creative of the family. I love collaborating with him. And similarly, inside Red Rover, I collaborate with David Perini, our head of product. He’s a UX designer and can draw things much faster than I can — he’s naturally gifted in that way. But I can envision things creatively and critique and edit well. Both my brother and I run businesses. That practicality of being able to take an idea and make it into something that someone else wants to use is key to building any business, especially a software business. There’s that back-and-forth creativity that is absolutely part of how I think, work, and hire.
The entrepreneurial spirit runs in your family! Have you always known you wanted to start your own business?
Problem-solving runs in the Sheldon family. All of us are optimizers, and our wives make fun of us for tweaking [things like saving] the extra minute from a drive or a few cents on a gallon of gas. I’ve always had that drive to not only make money but be industrious, and I started at a very young age. When I was five, I was collecting aluminum cans in the neighborhood and trading them for 50 cents or a dollar. It wasn’t about needing to have a lot of stuff; I’ve always been a saver. I got a paper route when we moved to Pennsylvania, and then I started doing software development while I was still in high school as an intern. I’ve just always had that drive, that sense of wanting to understand the whole business and ultimately wanting to have an idea I could run with and create a business [out of].
How do you and the other founders balance each other? In what ways does your role reflect servant leadership?
Certainly, we complement each other. I think I bring to the team a systems-number-minded perspective. On a scale of riskiness, Dani [co-founder and CEO] is on one end, willing to take calculated risks and dream big; Larry [co-founder and CCO] is definitely more conservative, noting that we’ve got a good thing going. I am somewhere in the middle. I like to swing back and forth. I’m like, ‘Yeah, let’s go for it! Here are all the reasons it’s going to be hard, but here are the reasons it could be great, and here’s how we’re going to mitigate it.’
I don’t usually remember that I have that [executive role] in the context of my team. I like solving problems as much as the next engineer at Red Rover. And I like to get into the weeds with whoever is asking the question. I don’t always have the answers. I like to ask questions and bring some of that perspective to the conversation, and hopefully, the smart people around me can kind of lead us to where we need to go.
What inspired the creation of Red Rover?
I knew there were only a few competitors in the field, and both had been developed more than 15 or 20 years ago. Since then, technology has come a really long way. Even before we started Red Rover, part of what I was thinking: ‘What technologies in today’s world make a difference in how somebody might solve a problem? Is it enough to solve the same problem again, or are there technological changes that have happened in those two decades?
So looking at it from that perspective, [and] thinking about everybody having a mobile device and broadband internet, [I’m] looking forward to what’s happening in AI and blockchain, and considering how those factors apply to us. And from a practical standpoint, things have changed in how school districts operate. There’s a sub shortage, [as opposed to] a boom back in the day. So, thinking about how schools leverage technology. Nobody was operating software online in 2000, let alone schools using software, so it’s a huge change. Schools now have technology all over the place. [Our job is to consider] how they’ve adapted and what they’re looking for in a modern solution.
What was missing, in the industry, that Red Rover sought to solve?
[A] big part of that was what our service team does, which is to listen to our customers. Our overall development process is really built around being responsive to customers and what the market is saying, and that really bleeds into our product development. We don’t have product managers or a separate product team; it’s all under my engineering team, which includes UX designers and developers who listen to customers. We try to take what we hear, ask why, develop it into a more robust solution, [so that we can] serve lots of districts across the country.
What is your leadership approach when guiding a team through building complex software, and how do you ensure growth?
A lot of it has to do with the intentional strategy — we have to hire great talent. We talk about being a talent-dense team. And we believe that will continue to attract more talent. People on the development team [embody] that balance of creativity, problem-solving, and execution, [and as a company, we tend to] attract others like that. So leading the team is a lot of back and forth, conversation, and collaboration. Ultimately, it’s about empowering the team because the people we hire are capable of making decisions.
What Red Rover values are reflected in the end product?
Customer empathy is definitely in the software because we’re very responsive to what the customer needs and what jobs they’re trying to accomplish with our software. I also think we’re very transparent in operating the software, [which is] another one of our values. We have a status page that we post to when things go wrong. We’re not hiding behind ambiguities; we try to be very upfront with our customers.
What do you love most about your team?
I love that my team is talented and that they love to own solving problems. They work together so well. You know, even when I’m not paying attention, stuff is still getting done. And they honestly care about what I am up to and if I’m healthy. They ask if I’m stressed out or taking care of myself. Like I said, I may hold the position and the title [CTO, co-founder], but I think of myself as just one member of the team at Red Rover.
What does success mean to you?
Do you remember the Doozers from Fraggle Rock? They are these little green guys who spend their whole lives building — that’s their whole joy in life. There’s an episode where the Fraggles stop eating the Doozer Sticks, and the Doozers don’t know what to do. Success for me is having people consume and use the software that I have helped direct and build, and that’s what [motivates me] and gets me excited: solving new problems, building new software, and having new customers to serve.
And I think my entire team operates similarly. That’s what has made us successful, and I think that is success on its own. And obviously that leads to great financial outcomes and the ability to have more members join the team to solve more problems — it’s kind of a flywheel effect.
