Manny Rivelo, CEO of ConnectWise – Interview Series

Manny Rivelo, CEO of ConnectWise, is a seasoned executive with over 30 years of experience leading and scaling global organizations in technology, cybersecurity, and enterprise software. Known for his strategic vision and operational expertise, he previously served as CEO of Forcepoint, where he drove transformation and growth in the cybersecurity sector. Rivelo has also held senior leadership roles at Cisco Systems, F5 Networks, and Arista Networks, honing his skills in strategy, product development, sales, marketing, and international expansion.

ConnectWise is a software company founded in 1982 and based in Tampa, Florida. It provides a unified platform for managed service providers (MSPs) and IT teams, offering solutions for automation, remote monitoring, cybersecurity, data protection, and more. Alongside its software, ConnectWise supports a global community of IT professionals through its IT Nation network, helping providers operate more efficiently and scale their businesses.

You’ve led major business transformations across multiple companies. What are the key ingredients for driving innovation at scale, especially in AI-heavy industries?

Driving innovation at scale, especially in AI-heavy industries, requires a clear vision, strong platform foundation, and deep understanding of where technology is headed. Currently, we’re seeing an intensified focus on AI, hyperautomation, and advanced cybersecurity as the core pillars reshaping the way MSPs and TSPs operate. To truly scale innovation, it’s critical to invest in technologies that automate routine tasks, enhance security, and integrate seamlessly into existing ecosystems.

At ConnectWise, we’re leaning into this with purpose, which is why we’re focused on making investments in the Asio Platform. Asio is an advanced, AI-powered platform designed to help MSPs streamline their operations, reduce costs, and fuel product innovation. It serves as the foundation of our ecosystem, providing the tools and capabilities that enable MSPs to automate processes, optimize workflows, and scale their businesses. Asio’s recent innovations have already begun to shape a more efficient, AI-powered MSP ecosystem. By focusing on tools that reduce complexity and increase intelligence across the stack, we’re helping our partners thrive in a market that demands agility, security, and efficiency. Innovation at scale comes down to building with intent, listening closely to your ecosystem’s needs, and making bold, strategic investments that future-proof your product and your partners. 

You’ve described hyperautomation and agentic AI as key to transforming IT services. Can you share specific ways ConnectWise is applying these technologies to help Managed Service Providers (MSPs) operate more efficiently?

The evolution of hyperautomation is a huge opportunity for MSPs because it enables them to deliver more scalable, efficient services to clients by automating complex processes across their IT and business operations. With ConnectWise RPA, MSPs gain a powerful, end-to-end hyperautomation solution designed to simplify operations, harnessing gen AI for intelligent workflows that seamlessly integrate into existing IT environments. Built on the ConnectWise Asio Platform, ConnectWise’s RPA solution leverages AI to automate tasks, like onboarding new clients and routing tickets, integrates with other systems, and creates fully customized workflows. For example, TechMD reported a 5–10% increase in operational efficiency after consolidating operations into a single platform powered by ConnectWise RMM™, PSA™, RPA™, and Sidekick™ — all within the Asio™ Platform — eliminating multiple logins and streamlining workflows.

Beyond RPA, ConnectWise integrates AI capabilities, such as machine learning (ML), for functionalities such as automated ticket categorization and resolution suggestions. At the core of it all is the ConnectWise Asio Platform, a centralized automation hub that unifies ConnectWise products, Microsoft solutions, and API-connected third-party apps. Built-in security features and enhancements like Security 360 have further strengthened the security posture of partners like TechMD. This empowers MSPs with a streamlined, intelligent automation engine that eliminates the need for disparate tools and simplifies complex processes. 

How does ConnectWise Sidekick leverage generative AI to reduce repetitive tasks and support decision-making for Managed Service Providers (MSPs)?

As the industry’s first purpose-built AI companion for IT solution providers (TSPs) and MSPs, ConnectWise Sidekick delivers real-time insights by intelligently analyzing data, enabling users to make smarter decisions, streamline workflows, and automate routine tasks. Acting as a trusted digital assistant, Sidekick helps users navigate complex scenarios with confidence, offering contextual, actionable recommendations when they’re needed most. By offloading time-consuming, repetitive work, ConnectWise Sidekick empowers businesses to focus on what truly matters: driving strategic growth and delivering exceptional value to their clients. 

What makes the Asio platform’s unified data layer a game-changer for AI-powered tools used by Managed Service Providers (MSPs)?

The Asio platform’s unified data layer consolidates and manages data from different sources within the platform, playing a crucial role in the effectiveness and efficiency of an MSP’s operations. With access to relevant, real-time data in a single location, MSPs gain insights into their clients’ IT operations, enabling them to make informed decisions, prioritize tasks, optimize resource allocation, and proactively address issues.

Asio’s unified data layer plays a critical role not just in connecting tools but in empowering MSPs to operate with full context. With all systems feeding into a single, consistent data model, Asio can deliver more accurate insights, smarter automation, and faster anomaly detection, helping MSPs work more proactively, not reactively. For example, when a device shows signs of performance degradation, Asio automatically initiates diagnostics, notifies the technician, and begins remediation steps, without requiring manual intervention. These capabilities enhance operational efficiency, reduce the risk of human error, and enable MSPs to deliver services with greater speed and precision.

Ultimately, a centralized data layer is one of the most powerful assets in an MSP platform. By leveraging this foundation, MSPs can optimize operations, elevate service quality, and deliver actionable insights that drive meaningful value for their clients.

How do you envision agentic AI evolving the way IT services are delivered, particularly in the Managed Service Provider (MSP) space?\

Agentic AI is set to revolutionize how IT services are delivered, especially in the MSP space, by automating tasks and decision-making. These AI agents are growing increasingly powerful and are already capable of IT processes, such as handling routine network monitoring, automatically identifying and responding to issues before they become critical, and more. As the workforce becomes more comfortable with AI, adoption is accelerating, and the barriers to using AI are dropping. This shift will transform how MSPs operate, allowing them to work smarter and more efficiently.

However, the rise of agentic AI also introduces new risks, particularly when it comes to cybersecurity. Cybercriminals are already leveraging AI to create more sophisticated attacks, and to stay ahead, MSPs must use AI to defend their systems. While AI can help identify and mitigate threats faster than humans, its rapid adoption raises concerns about unintended consequences. The key will be balancing the power of AI with strong oversight to ensure it serves as a secure, reliable tool for MSPs while minimizing risks. 

What advice would you offer other executives trying to modernize their organizations through AI, especially when working with legacy systems? 

When modernizing an organization with AI, my advice is to move strategically, not just quickly. This starts with knowing the considerations before integrating AI into your business. Start by identifying high-impact areas where AI can automate routine tasks or enhance decision-making, but make sure you’re building on a solid foundation of data security, accuracy, and compliance.

Legacy systems don’t have to be a barrier; they can be part of the transformation if you focus on integration, not replacement. Look for AI solutions that complement existing infrastructure and bring value without forcing a complete overhaul.

Data privacy and security must also be top priorities. Ensure guardrails are in place to prevent sensitive information from leaking into AI models. Accuracy is another critical factor; AI is only as good as the data it’s trained on, and mistakes can damage credibility. Don’t overlook compliance requirements, either; these vary by industry and location.

As the former CEO of Forcepoint, you’ve had a front-row seat to the evolving cybersecurity threat landscape. How is AI changing both the attack and defense sides of cybersecurity?

AI is transforming both sides of the cybersecurity battlefield. On the attack side, threat actors are leveraging AI to launch more sophisticated, faster, and harder-to-detect attacks, including phishing, deepfakes, and automated vulnerability discovery. With generative AI in play, Gartner predicts that by 2027, 17% of cyberattacks and data leaks will involve AI.

On the defense side, AI is becoming a powerful ally, helping security teams detect vulnerabilities, automate responses, and proactively assess vulnerabilities. However, as AI becomes more embedded in business operations, it also becomes a new attack surface that must be protected. AI is raising the stakes on both ends, making it essential for security strategies to evolve just as quickly. 

How is ConnectWise using AI to help Managed Service Providers (MSPs) strengthen their cybersecurity posture?

ConnectWise Security360 is a next-generation cybersecurity solution powered by AI and designed specifically for MSPs. Focused on attack surface management (ASM), it simplifies the oversight of complex security stacks, enabling MSPs to strengthen client defenses with greater precision and ease.

Security360 provides a comprehensive, 360-degree view of the entire security landscape, allowing MSPs to assess risks, prioritize vulnerabilities, and automate threat responses. By aggregating data from multiple security tools, the platform delivers a real-time snapshot of each client’s security posture. AI-driven analysis powers features like MSP security scoring and automated identification of high-risk clients, helping MSPs take targeted action where it matters most. Security360 also offers deep visibility into client environments, highlighting critical details such as outdated agents, active threats, and patch compliance, giving MSPs the insights they need to stay ahead of evolving threats.

Additionally, ConnectWise Sidekick for Security, an AI-powered digital assistant, takes cybersecurity support to the next level by automating critical tasks and delivering real-time insights. From managing tickets and assessing security posture to streamlining threat response, Sidekick for Security helps MSPs work smarter and faster. Using natural language prompts, MSP owners and technicians can instantly query the assistant to gain a clear view of their own or their clients’ security environments, pinpointing high-priority risks and determining the next best actions with confidence.

What is the IT Nation community and how does it influence the direction of AI development and feature design at ConnectWise?

Community has always been at the heart of ConnectWise and the MSP ecosystem, and we believe that when MSPs have the right resources, connections, and support, their potential for success grows. That’s why IT Nation exists: ConnectWise’s global community of tech pros—mostly MSPs and IT providers—who come together to connect, collaborate, and level up their businesses and careers. It’s a place where members tap into events, peer groups, and other resources that help them grow, solve challenges, and stay ahead of the curve.

Through events like IT Nation Connect and IT Nation Secure and regular feedback loops built into product development, ConnectWise actively listens to its community’s real-world needs, challenges, and aspirations. That direct input shapes how AI features like ConnectWise Sidekick, Security360, and RPA tools are built, keeping them useful, impactful, and always evolving with the real-world demands of TSPs and MSPs.

Overall, the IT Nation community acts as both a sounding board and innovation partner, ensuring ConnectWise’s AI capabilities are not only cutting-edge but also highly practical, relevant, and aligned with the evolving needs of TSPs and MSPs.

How do you see the role of IT professionals within Managed Service Provider (MSP) companies evolving as AI becomes more embedded in everyday operations?

As AI becomes more deeply embedded in MSP operations, the role of IT professionals is shifting from task execution to strategic leadership. At ConnectWise, we see automation and tools like Sidekick enabling technicians to offload repetitive tasks, like ticket triage or patching, so they can focus on higher-value work such as designing workflows, driving client outcomes, and proactively managing cybersecurity.

This evolution means IT pros will need new skills in areas like automation design, data interpretation, and AI integration. Our mission is to help MSPs not just keep up but lead by giving them the tools, training, and insights to operate more efficiently and become trusted advisors in their clients’ digital transformation journeys.

 What excites you most about the future of AI in IT and business operations—and what challenges do you think are still ahead?

We’re in the middle of a major innovation wave, with AI and automation transforming how we work. At ConnectWise, we’re helping MSPs tap into that potential to boost efficiency, security, and profitability. However, as AI advances, so do the threats; cybercriminals are using AI, too. That’s why we’re focused on secure implementation, smart automation, and ongoing education. The upfront investment is real, but so are the long-term gains: better security, stronger operations, and real business growth.

Thank you for the great interview, readers who wish to learn more should visit ConnectWise.