Don’t Shout AI
Not, at least, if you want admission to ConnectWise’s PitchIT program, which gives companies with concrete answers to specific MSP use cases a shot at $150,000 in prizes.
Squash is one of many vendors touting AI-based managed services functionality these days. Sandeep Uppaluri, the company’s co-founder and CEO, is the first to admit that sorting through them all is hard work for MSPs.
“Every vendor claims to have AI solutions,” he says. “There are just a lot of different things coming at them in different ways.”
Sean Lardo feels their pain. Every spring for the past several years, he’s led a committee at ConnectWise tasked with deciding who gets into the company’s annual PitchIT program, a 16-week startup incubator that hands out $150,000 worth of prizes to the three best graduates.
“It was very challenging this year,” says Lardo (pictured), ConnectWise’s vice president of IT Nation Communities. And not just because the applicant pool was unusually deep (over 65 companies competing for what turned out to be 25 slots).
“These companies are claiming AI in everything,” Lardo says, adding that it didn’t impress the judges. “You shouting AI doesn’t mean you have anything. It’s about what you’re doing with it. What’s the actual use case?”
The use cases Lardo and his fellow evaluators prioritized reflect their read on what MSPs most want and/or need right now. “If you look across the board for this class, everybody represents some segment or fraction of the business that’s a necessity or will be more of a necessity moving forward,” Lardo says.
Some of those necessities relate directly to AI itself. Class-members Synthreo and Aportio, for example, make AI-powered service desk automation software while Lemhi, which you met here recently, helps MSPs sell customer-facing AI services. Kipling Secure’s solution, meanwhile, aims to help users mitigate the risks those AI services can pose.
“AI cybersecurity is big because AI hacking is a real thing now,” Lardo says. “It’s happening faster, more often, and it’s really hard.”
Other contestants, including Handover, TechAlign, and MSP Report Card, help with more traditional tasks like conducting quarterly business reviews, something too few MSPs do at all, according to Lardo, and fewer still do properly.
“They don’t use them for what they should be, which is an actual growth tool, a sales enablement tool,” he says.
Lardo advises MSPs struggling to evaluate the many young vendors vying for their business to ask the same questions he and his team did when vetting would-be PitchIT contestants. Does the leadership team have experience in managed services? What do people say about the company online? How long has it been around?
“You have to look at their credibility,” Lardo says. “We don’t expect ten years of business, but we do expect to see a couple of years of them doing things.”
ConnectWise will name this year’s three finalists in September. Two months later, a panel of judges from outside the company will crown the winner at the vendor’s IT Nation Connect event in Orlando. Which contender grabs their eye most will offer an interesting glimpse at what a winning recipe for success with MSPs looks like in the age of AI.
Speaking of AI-era startups…
The founder and CEO of one, Cyft, joined us on the most recent episode of MSP Chat, the podcast I co-host, for a thoughtful look at the present and future of AI-powered productivity for MSPs. Give it a watch here and check out all of our other interesting guests here.





