A little over a decade ago, Mark Tipton and the late longtime LM columnist Kevin Kehoe put their heads together to create a software solution for the landscape industry. Today, Aspire Software is one of the largest business management systems for contractors across the nation, with hundreds of employees servicing the landscape industry alone.

“And we’re not slowing down or backing off,” Tipton tells LM. “We’re able to hire the talent that has industry experience. Our team has well over 500 years of industry experience, meaning we’ve hired former contractors who are now serving our clients. We’re investing more as we go forward. We haven’t topped out — we haven’t peaked yet.”
Shortly after the release of the June LM150 issue, LM caught up with Tipton to discuss all things Aspire.
Landscape Management: How does it feel to look at the LM150 list and realize that so many of the biggest companies in the industry are your clients?
Mark Tipton: Well over a third of the LM150 list are running on the Aspire platform. It’s very motivating to be able to have an opportunity to play a part in the success that these businesses are having as they continue to grow. Since the beginning, the vision I had for Aspire was really to change the industry, and it’s exciting to see that become a reality as Aspire is adopted by more and more of those leaders that you see on that list and across the industry.
LM: Do you ever go back and reflect on how it all got started? How much has Aspire changed over the years?
MT: You know, it hasn’t changed a ton. If you go back and look at our original plan from 10-plus years ago, it was certainly ambitious. It was big. I’m not sure I really understood what big looked like until we took some of those steps we have to be where we are today. Since the beginning, the vision was we wanted to change the industry. It’s just hard work. But when the (LM150) list comes out, and you step back and you look at the names on the list and the contributions we had and working with so many of the companies on the list and getting a chance to speak with them and hear about the impact we’re making … it certainly just takes you back to those early days, that early vision. And now getting a chance to see some of that happening? It’s certainly gratifying, and it’s fun to be a part of.
LM: How about the industry as a whole — how have you seen it change?
MT: It’s harder and harder to run a business in this industry. Labor costs keep going up at rates that are higher typically than the price increases that you can give to your customers. To really effectively run the business, you need to manage it better. Software has become a more and more important piece of that.
LM: How do you see new technologies like artificial intelligence (AI) changing the industry?
MT: AI is going to have a big impact, and it’s coming in the forms of different things; not just on the software side, but also on the equipment side with autonomous mowers. And there’s going to be integration with the autonomous mowers and the software platforms. We’re working on that today, and we’ll be rolling it out in the next year.
There’s a lot changing (with AI). We’re also seeing the changes go more from just the basic to more specific. From “How do I get my jobs scheduled? How do I invoice my customers?” to taking the next step from that to “How do I really analyze my business? How do I look at my portfolio? Who are my best customers? Who are the customers that I’m not making money on that I either need to raise prices or replace with another customer that I can make money on?”
LM: What excites you about the future of Aspire? What’s next for your company?
MT: We’ve made some significant investments over the last year. I’m excited about investments on our Crew Mobile app that allows customers to work disconnected. Some of our customers work in remote areas, and they need their crews to be connected in the field even when they’re not connected. We were able to do that this year, introducing new levels of security and facial recognition for teams to be able to clock in and clock out. There’s now snow subcontractor management and marketing. One of the values we get from being part of ServiceTitan is we can introduce new products to the ServiceTitan portfolio. We introduced Marketing Pro this year, which is a powerful product to really help you grow your business.
LM: How has the acquisition by ServiceTitan gone within the walls of Aspire?
MT: It’s going fantastic. If you look at where we are today versus where we were three years ago, certainly we’ve grown as a business significantly, but we’ve also made tremendous investments in the platform itself. Our year-over-year investment in just research and development alone is three times, maybe four times what it was pre-ServiceTitan. They’ve really enabled us to make those investments.
LM: Do you have a most memorable day at work, maybe from the early days of getting Aspire off the ground?
MT: There were a lot of days along the way. Some were bittersweet, some just felt big. One in particular I remember was probably in 2015 or 2016. We were still an upstart. We had customers, we were a small business, but we were making inroads, bringing on some nice logos onto our platform, and we had a big hotel room at GIE+EXPO. We were going to have some prospect meetings and hopefully move the ball forward on some deals that we were pursuing. There was one company in particular — I won’t mention their name to protect the innocent — but it was a big deal opportunity for us. We had some good successes along the way, but this was a next-level one. We had the meetings with them there, and even though we didn’t close the deal there, we walked away from that meeting in that hotel room knowing we were going to close the deal and knowing it was a game-changer. Kevin and I and a couple of others of us were there, and just that moment, both during the meeting and once the meeting was over, we were looking at each other going, “OK, this is real, this is really going to happen.” It was going to happen as big as we’d hoped it was.