In an industry defined by rapid change and constant innovation, one thing has always kept the IT channel grounded: the MSP community. Few people understand that better than Gary Pica, chief community officer at Kaseya.
From peer groups to digital forums, Pica has helped shape how MSPs connect, learn, and grow together. He founded TruMethods LLC, which Kaseya acquired through its IT Glue business unit in 2021. The deal brought Pica’s TruPeer peer group program and overall framework into Kaseya’s fold. This propelled Pica’s vision of community-driven MSP success into a broader scale.
Pica sat down with ChannelPro at the recent DattoCon 2025 conference in Miami. There, he shared how Kaseya is expanding its community initiatives, why collaboration is the channel’s secret weapon, the “monumental” influence of AI, and more.
ChannelPro: What Does ‘Community’ Mean for Kaseya and the Channel?
Pica: Community is such an important thing for this industry, especially in the decades that I’ve been doing this. In times of change, we really lean on each other. At Kaseya, that community takes a lot of forms. Part of it is the peer groups that I run with Dan Tomaszewski; we have 1,000 members across three continents. Part of it is our events and our local gatherings. Part of it is our industry team that we send out to be part of the broader community. And part of it is our digital community.
My vision for Kaseya’s community is to greatly expand it going forward. That means releasing an all-new digital community where people can connect and access resources at scale. We can now offer at scale the things we do with enablement, like our MDF dollars or sales and marketing training. In addition to peer programs, which only some companies can join, we want to help every MSP that wants to be part of something. My job is to make sure that’s the direction we go.
Gary Pica is a well-respected leader and collaborator in the MSP community.
ChannelPro: What Does That New Digital Community Include?
Pica: Software companies have digital communities, forums and online spaces for customers to connect. We have those for each of our products, but the next step is connecting them into one broader Kaseya community. That way, people can get questions answered by Kaseya staff and product owners, but also connect with other users. Owners can connect with owners. We can share industry news, provide free technical and sales training, marketing help, and resources to help them run a better business. It lets us connect and share on a much larger scale.
ChannelPro: So, Like Reddit, but Less Mean?
Pica: Yeah, and it’s not anonymous. Everyone’s honest about who they are, and they’re here for the right reasons: to help. If people have a problem, it’s okay to bring that too. It’s a great way to get attention from us. We monitor it through a team devoted to making sure that wherever issues come up, we can deal with them.
ChannelPro: Is This Driven by Customers or by Kaseya Leadership?
Pica: The best communities are the ones that the community owns. The goal is to build it in a way where advocates and customers play a big role so they feel like it’s their community. What they have in common is that they use Kaseya’s stack, and we’re the ones investing in it, nurturing it, and providing the resources.
ChannelPro: You Mentioned Events Earlier. How Do Events Tie into Your Community Strategy?
Pica: Events are a big part of it. You can see what we do here at DattoCon, where we can share our message and vision directly. Also, under Tomaszewski, our team goes to 200 non-Kaseya-branded events around the world each year. That team’s purpose is to bring the Kaseya message out to the marketplace. We don’t just want the community to come to us; we go to the community.
Building an engaged community has always been a key goal for Pica.
ChannelPro: Speaking of Going Out to the Community, What’s Your Take on the Hottest Topic, AI and Its Impact Across the Channel?
Pica: Every industry event you go to right now is about AI. It’s something both vendors and MSPs have to address, but it’s also affecting every one of their customers. Whatever industry they’re in, they’re trying to figure out their AI strategy. We’ve been through big transitions before, but this one is monumental.
Kaseya’s in a strong position because we have the most scale, data, and products. That matters when it comes to delivering AI solutions that actually work for MSPs. MSPs don’t really want AI; they want the results of it. They want fewer tickets, faster resolution, and more secure, productive clients. Our job is to take as much of that burden off of MSPs so they can focus on building new services and helping their customers harness AI, too.
ChannelPro: Beyond AI, What Other Areas Should MSPs Pay Attention To?
Pica: Compliance and security are evolving fast. The regulatory environment keeps changing by state, by country, by province — and security threats are shifting constantly. I’m on a cybersecurity podcast for MSPs, and every month, there’s something new. The bad actors adapt faster than the protectors, especially with AI. It’s easier for them to use it to attack than it is for us to adapt it for defense.
ChannelPro: Are the SMB Clients More Aware of Those Risks Now?
Pica: Definitely more than before. They can’t turn on the evening news without hearing about a cyberattack. They’ve made investments, but still not enough. I used to tell my MSP clients, “It won’t be enough until the bad guys stop,” and they’re not going to stop. When MSPs tell me their customers don’t value security, I tell them that is their own fault because they haven’t explained the risk properly.
Gary Pica
ChannelPro: How Should MSPs Approach AI Adoption Within Their Own Businesses?
Pica: We’re encouraging MSPs to start by implementing it internally, using AI in their own technology and operations. Start with help desk tickets, then expand it to finance, sales, marketing, and then all areas of the business. That’s what their customers will need to do. MSPs have to get there first, or someone else will take their clients there. It needs to become part of your culture. You can’t sell something that your own business hasn’t embraced.
ChannelPro: What Excites You Most About the MSP Community Today?
Pica: The people. When I started in this business, I thought my job was to teach others how to run a better MSP. But I quickly learned that it’s really about people. I’m helping them unlock their potential and helping their teams do the same. The great part is that when there’s change like now, that’s when opportunity is greatest. That’s why I’ve stuck around this industry.
ChannelPro: Why Is the IT Channel So Uniquely Collaborative Compared to Other Industries?
Pica: It’s been that way since the beginning. Other industries don’t have what we have: big vendors who create events, build communities, and bring people together. You need space to gather, and that’s what those vendors provide. That’s how this all started when we went from IT providers to MSPs. We had things to figure out, so we did it together. Thirty years later, that spirit is still here, and I love it.
Anjali Fluker is senior channel editor for The ChannelPro Network, where she covers news, trends, and best practices for the MSP community. She specializes in telling the stories that matter to IT providers serving the SMB market. When she’s not reporting on the latest in managed services, she’s connecting with channel pros at industry events across the country.
Images: Anjali Fluker/ChannelPro
