The Servant Leader: A Conversation with ConnectWise CEO Manny Rivelo

Running a company in the tech world has never been for the faint of heart and is especially challenging at the nexus of IT management and security. That certainly has not deterred new ConnectWise CEO Manny Rivelo, a man who clearly likes a challenge. With a little over 100 days at the helm of ConnectWise, Rivelo presented a compelling vision for how office technology resellers and MSPs can deliver value in an increasingly complex tech ecosystem.

Rivelo had already been introduced to a large slice of ConnectWise’s MSP partners at their big IT Nation Connect event in November in Orlando. My chance to meet Rivelo finally came at the Executive Connection Summit in January in Scottsdale. In true ECS fashion, my interactions ranged from a formal sit-down interview, to watching Rivelo present from the stage and ultimately to an informal cigar and bourbon reception. Needless to say, we covered some ground. 

Culture and community: A unique ecosystem

Right off the bat, I wanted to know what made the biggest impression for Rivelo as he stepped into his new role at ConnectWise. There were two things. The first, he said, which struck him immediately, centered around how great the culture is at ConnectWise. 

The second became clear to him at IT Nation Connect. Rivelo expressed genuine enthusiasm for the entrepreneurial spirit that defines MSPs and office technology resellers, saying “This is a community that will provide input and feedback. They will show up and they’ll tell you what’s broken, what’s working, what’s not. There are very few industries where people come together and are willing to share how they’ve been successful. This community does that — it’s different. Try to get this is at a banking convention.”

This openness and willingness to share best practices is a hallmark of the dealer community, and it’s clear that Rivelo sees it as a key strength. He emphasized the importance of ConnectWise supporting and engaging with this community, recognizing that their success is intrinsically tied together. And it’s not just talk. ConnectWise is doubling down on initiatives like peer groups, partner conferences, and resource-sharing platforms to create opportunities for collaboration and mutual growth. 

The MSP landscape: Opportunity amid complexity 

The role of MSPs is changing rapidly as businesses rely more heavily on technology, automation, and AI to drive their operations. Rivelo was quick to acknowledge the pressures and possibilities of this evolution, which is both an inflection point and a massive opportunity. For ConnectWise, enabling MSPs to seize this opportunity means delivering solutions that reduce complexity while enhancing capabilities. 

When I asked Rivelo about the biggest challenges facing MSPs and office technology resellers, he identified several key areas:

• Talent shortage: “So many resellers are moving into this IT space, and IT tech labor is at negative unemployment.”

• Talent optimization: “How do I get more productivity from the people I have? How do I enable more creative, higher-level work from our team and automate and deploy AI for some of the lower value work?” 

• Security stack development: “What does my security stack look like? What should I offer my customers to provide comprehensive security while maximizing ROI?”

• Driving ideal customer profile (ICP) engagement “What is my ideal customer profile that I’m going to support? How do I engage with them and deliver value as a trusted advisor? What technology should I be bringing?”

These challenges also present opportunities for innovation and growth, which ConnectWise is actively addressing through its platform development and community initiatives.

The platform vision: Unifying the MSP tech stack

At the heart of Rivelo’s strategy for ConnectWise is the development of a unified platform for MSPs. He explained the rationale behind this ambitious project:

“When I look at the big markets that are out there, there’s an opportunity to build the first unified MSP platform. Our partners, whether they are an office technology dealer or an MSP, are supporting IT needs for an end customer who needs proper and efficient protection. They are working with an average of about 25 products, but it can range anywhere from a couple dozen solutions to 80, as they try to put a stack together as best as they possibly can.”

The goal is to consolidate this fragmented landscape into a cohesive, efficient platform. Rivelo likened it to the evolution of Microsoft Excel, which became a platform that revolutionized productivity software.

Rivelo used an interesting metaphor to describe the current state of ConnectWise’s platform development.

“We’ve been working underneath the water for a while, building the data stores, building the common services, all those critical elements. The value is when you get above the water. The value is when you get the user application.”

He indicated that 2025 would be an exciting year for ConnectWise, with several platform features set to be unveiled at upcoming events like IT Nation Secure in June and IT Nation Connect later in the year.

AI and automation: The game-changers

Rivelo is particularly excited about the potential of AI and automation to transform MSP operations. AI in particular is enabling predictive insights that help MSPs resolve issues before they become problems. ConnectWise’s platform integrates advanced tools — like AI-driven threat detection and robotic process automation (RPA) for vulnerability patching — with the kind of support MSPs need to stay competitive. These innovations promise to improve efficiency and allow MSPs to support more end users with the same resources.

The company plans to continue investing heavily in R&D, with a focus on enhancing its platform’s capabilities in cybersecurity, AI,
and automation.

Prioritization is key

There can be a danger in trying to do too much — it can invite paralysis. Rivelo is focusing his team on delivering their key initiatives, starting with the singular most important item on the list and moving down from there. Rivelo believes the team can accomplish more, faster by deploying this method. He wants the focus to extend across the entire value chain of the organization. 

A servant leader

As our conversation drew to a close, I asked Rivelo about his management style. His response revealed much about the values that drive him as a leader:

“I’m a servant leader. I always push the cost of improvement, and I am incredibly curious. It doesn’t matter whether the results are good, flat or down. I want to understand why. And the reason I want to know why is because I believe that if I can understand why, I’m able to accelerate it in a positive manner.”

This curiosity and drive for continuous improvement permeate Rivelo’s approach to leadership. He emphasizes the importance of surrounding himself with highly skilled team members and leveraging the wisdom gained from decades
of experience in various industries.

The future is bright

Manny Rivelo’s vision for ConnectWise is both ambitious and grounded in a deep understanding of the tech world. By focusing on platform development, community engagement, and leveraging cutting-edge technologies like AI and automation, ConnectWise is positioning itself to lead the next wave of innovation in the MSP space while bringing the entire MSP community along for the ride. It’s going to be quite a journey — one that will reward those who are ready to innovate, collaborate, and grow.  

Patricia Ames is president and senior analyst for BPO Media, which publishes The Imaging Channel and Workflow magazines. As a market analyst and industry consultant, Ames has worked for prominent consulting firms including KPMG and has more than 15 years experience in the imaging industry covering technology and business sectors. Ames has lived and worked in the United States, Southeast Asia and Europe and enjoys being a part of a global industry and community.