AI Certification for MSPs Debuts as ConnectWise and Kaseya Make Major Strategic Moves

[00:00:02] It's Tuesday, June 3, 2025 and I'm Dave, so four things to know today. ConnectWise unveils its unified MSP platform and ISO-powered PSA to streamline operations. Kaseya times a surprise CEO appointment to challenge that spotlight. Breach Secure Now launches the first AI certification program for MSPs. And BC Investment Model Shift is AI Rollup's target services businesses. You'll want to stick around for that one.

[00:00:29] This is the Business of Tech. ConnectWise is hosting their IT Nation Secure event and launched the latest version of their security information and event management solution designed specifically for managed service providers. Key features include unified log management, automated alert triage and customizable dashboards which aim to boost productivity and reduce incident response times for providers managing diverse client environments.

[00:00:55] ConnectWise also has announced the launch of its new professional services automation solution powered by ASIO, along with the introduction of ConnectWise Pro, a unified platform packaging offering for managed service providers. The PSA powered by ASIO introduces a modernized experience for service desk and operations teams featuring a common interface, shared data across tools and embedded automation capabilities.

[00:01:21] ConnectWise Pro offers an all-in-one package that simplifies operations by bundling critical tools into a single contract, allowing partners to choose between different pricing models based on how they charge clients. ConnectWise, in partnership with Microsoft and PAX 8, has launched ConnectWise Endpoint Management and Security from Microsoft 365.

[00:01:41] This new solution combines Microsoft 365 Business Premium, which includes productivity and security features, with ConnectWise's Remote Monitoring and Management Pro, and managed detection and response from Microsoft Defender. The solution will be available through the PAX 8 marketplace, simplifying procurement and billing processes. Why do we care?

[00:02:02] ConnectWise's announcements at IT Nation Secure 2025 show its doubling down on platform consolidation, modernizing core tooling with ASIO, and leaning into strategic partnerships, including Microsoft and PAX 8, to deepen its role as a backbone provider for MSP operations. By launching ConnectWise Pro, the company is bundling PSA, RMM, and MDR into a single offer with flexible billing. This isn't new in the industry, but the move is about catching up and keeping up.

[00:02:30] The new ASIO-powered PSA is positioned as a modern experience, shared data layers, automation, and UI parity across modules. That's long overdue, and notably was soft-launched back in November. ConnectWise is attempting to reassert itself as the central nervous system of the MSP, not just a collection of tools. For partners, the question is less about feature parity and more about operational efficiency, vendor trust, and long-term platform viability. Your key action?

[00:02:59] Evaluate whether ConnectWise's Unify's platform pitch reduces administrative drag for your teams without giving up the flexibility your clients' demands. If the answer is yes, this could be worth the reinvestment. If not, don't be afraid to maintain or deepen your stack diversity. This episode is supported by FlexPoint. Managing cash flow can be tough for managed service providers.

[00:03:24] FlexPoint's working capital solution is designed to bridge the gap between invoicing and payment, giving providers access to funds when they need them. With quick approvals and flexible terms, it helps cover expenses, invested growth, and maintain financial stability. Keep your operations running smoothly with FlexPoint. Visit getflexpoint.com slash MSP dash radio to learn more.

[00:03:49] Select, heard it on the business of tech or MSP radio, you'll get 10% off. I love the audacious timing of this during ConnectWise's event. Kaseya has appointed Rania Sukar, a former executive from Google and Intuit, as its new CEO, effective June 3, 2025. Sukar, who holds multiple degrees from Harvard, brings over a decade of experience in developing innovative technology solutions aimed at small businesses.

[00:04:17] In her new role, Sukar emphasizes a commitment to enhancing customer experience and accelerating innovation, stating that artificial intelligence and automation will be pivotal in improving profitability for their customers. Industry leaders have expressed optimism about Sukar's leadership, noting her background in software and her fresh perspective as she steps into this position.

[00:04:37] Michael Goldstein, CEO of Lan Infotech, highlighted Sukar's experience in the software-as-a-service market, particularly her work at Intuit and Google, as instrumental in navigating the future landscape of technology solutions for managed service providers. Why do we care? Why do we care? You don't appoint a new CEO on a Tuesday by accident, especially not during your biggest competitor's flagship event.

[00:05:01] Kaseya naming Rania Sukar as CEO on the exact day of ConnectWise's IT Nation Secure is a deliberate and strategic move, meant to shape headlines and own part of the narrative. You'll note I'm covering it. Nobody starts a C-suite job on a Tuesday. This announcement was timed to the hour, designed to disrupt the news cycle around ConnectWise's product launches and executive keynotes. Sukar almost certainly started weeks ago.

[00:05:25] But the reveal was choreographed to compete with attention during ConnectWise's moment in the spotlight. Now, Sukar's background, Google, Intuit, multiple Harvard degrees, is not the typical private equity install. She's a product and growth leader with a strong small business focus, not just a PE-friendly operator. Her work at Intuit, notably on QuickBooks Capital, focused on small business automation and growth tools. That's highly relevant to MSPs navigating S&B environments.

[00:05:53] Her emphasis on AI aligns with both Kaseya's marketing narrative and broader industry pressures for margin improvement. It also hints that we'll see acceleration in baked-in intelligence in their product line. From MSPs, the real question is whether she can back up the narrative with operational improvements that matter. Fewer support headaches, smarter automation, and genuine ease of use. Keep an eye on product cadence and partner experience over the next 6 to 12 months.

[00:06:20] That's where we'll see if this is just another headline or a turning point. Breach Secure Now has launched the industry's first generative AI certification program, specifically designed for managed service providers. Early adopters like Stack Cybersecurity have already recognized the value of such training, indicating that proper AI strategy is essential for both leveraging opportunities and mitigating risks.

[00:06:44] The certification provides MSPs with training on AI fundamentals and best practices for cybersecurity, equipping them to confidently guide their clients through the complexity of AI adoption. Radware has expanded its threat intelligence services with two new offerings, the Telegram Claimed Attacks Report and the TLS Fingerprint Reputation Feed.

[00:07:04] The Telegram Claimed Attacks Report aggregates claims made by hacker groups on the messaging platform Telegram, offering insights into potential threats targeting specific industries. Key features include timely updates every 15 minutes and user-friendly dashboards. Meanwhile, the TLS Fingerprint Reputation Feed identifies and blocks malicious TLS fingerprints, enhancing protection against cyber threats with minimal operational effort.

[00:07:29] And NinjaOne has successfully completed its acquisition of DropSuite, a cloud backup and data protection firm, in a deal valued at $270 million. The acquisition aims to enhance NinjaOne's capabilities in protecting data, ensuring business continuity, and simplifying compliance for its customers. Founded in 2011, DropSuite specializes in backup solutions for critical workloads and targets managed service providers. Why do we care? I'm going to focus on what?

[00:07:56] Breach Secure Now's new generative AI certification program may not sound like breaking news, but it should be. It's the first structured attempt to give providers a formal framework for guiding clients on AI usage, security, and policy. AI is already inside SMBs, often unmanaged. This isn't about deploying AI, it's about helping clients govern the tools they're already using. MSPs need to lead, not react. Waiting for vendors to define AI best practices means missing the moment.

[00:08:25] This certification positions providers to lead AI policy conversations, just like they did with cloud migration a decade ago. There's early mover advantage here. Being first to market with a structured, MSP-specific AI certification could cement Breach Secure Now as the default AI training partner, unless competitors catch up quickly.

[00:08:48] This is a strategic shift in the way investing is being done, I wanted to note, as it's got some implications, and the story has appeared in three different versions you'll cover now in my feed. Venture capital's series progression is stalling at the seed stage, according to new data released by Carta. In the first quarter of 2024, 46% of all seed deals were classified as bridge rounds, marking the highest rate for any stage that Carta has tracked.

[00:09:14] The decline in traditional funding rounds is attributed to market volatility, which is prompting startups to delay new priced rounds until they have a clearer valuation expectation. Notably, the number of series A deals fell by 79% from the first quarter of 2022 to the first quarter of 2025.

[00:09:34] This stagnation at the seed stage could impact return on investment expectations for later stages, particularly affecting limited partners who invest in series A or series B-focused funds. TechCrunch reporting solo investor Elad Gill, an early investor in AI, is now focusing on a new investment strategy that leverages AI to transform traditional businesses through what are known as roll-ups.

[00:09:59] Gill aims to acquire established service-oriented companies, such as law firms, and enhance their operations using AI to significantly improve profit margins. Over the past three years, Gill has already supported two companies pursuing this model, one of which is Enam Company, valued at over $300 million. He notes that while roll-ups utilizing technology have been attempted in the past, they often lack genuine technological integration.

[00:10:25] Gill believes that advancements in artificial intelligence could radically alter the cost structures of these businesses, allowing for increased cash flow and more aggressive acquisition strategies. He remains optimistic about the evolving landscape of AI and its potential to reshape various industries, particularly in sectors like legal and healthcare. And Koshla Adventures is exploring a new investment strategy by acquiring mature businesses and enhancing them with artificial intelligence.

[00:10:52] This approach, similar to private equity roll-ups, has already attracted attention from other firms like General Catalyst, which has invested in seven such companies, including Long Lake, which focuses on managing homeowners associations. Samir Kool, a general partner at Koshla Ventures, indicated that while they are cautious, the firm sees potential in marrying established companies with new technology to benefit both parties.

[00:11:15] This strategy may help artificial intelligence startups gain immediate access to large, established clients, addressing the challenges many face in securing customers. Koshla Ventures aims to conduct a few deals to evaluate the returns on this investment model before potentially expanding its efforts. Why do we care? There's a quiet but foundational shift happening in how capital flows into technology and services businesses, and is not the usual VC narrative.

[00:11:42] The stalling of venture capital progression at the seed stage and the emergence of AI-powered roll-up strategies signal a re-ordering of where the perceived value lies. And for IT services firms, this could reshape competition, valuation, and even exit strategies. Cardi's data is stark. Nearly half of all seed deals are now bridge rounds, and Series A deals are down 79% since Q1 of 2022. The classic startup progression, seed, Series A, B, exit, is no longer reliable.

[00:12:13] Valuation uncertainty and exit environment pessimism have made growth stage capital scarce and expensive. What a lot of guild, Koshla Ventures, and others are doing isn't new in structure. It's a classic private equity roll-up. What is new is the core thesis, using AI to radically shift operating margins, not just drive revenue through scale. Traditional roll-ups lead on financial engineering and operational discipline. These new AI roll-ups focus on cost transformation through tech integration,

[00:12:40] especially in people-heavy industries like legal, healthcare, or managed services. It's not about digitizing workflows. It's about replacing workflows entirely using AI. This is a strategic alignment of capital and capability. Investors are signaling they no longer want to wait years for seed stage AI startups to mature. Instead, they're buying profitable businesses now and applying AI to them immediately. For IT services firms, this is both a warning and an opportunity.

[00:13:08] If you're not already considering how AI reshapes your margins, service delivery, and scalability, you're leaving value on the table. Meanwhile, someone else may be preparing to extract it. Today's episode is supported by Huntress. Most cybersecurity solutions are built for massive enterprises with big budgets. Not Huntress. They're the fully managed cybersecurity platform built for all businesses, not just the 1%.

[00:13:36] Huntress purposely builds security solutions like EDR, ITDR, SIM, and security awareness training to equip their team of elite threat hunters to handle the heavy lifting of security for you. When threat actors strike, Huntress's 24x7 Global Sock shuts them down before they're even on anyone else's radar. But they do more than just chase alerts. They lead the charge in industry research and knowledge, bringing expert protection and peace of mind.

[00:14:04] That's why users on G2 rate their EDR number one for growing businesses. To see how their expert threat hunting team gets the job done, visit Huntress.com slash MSB Radio. Thanks for listening. Today's National Egg Day and National Chocolate Macaroon Day. Not the other macaroons, mind you. Just the chocolate ones. You wait your turn, pistachio.

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