Recap of Len’s AI & Automation Sessions at MSP Summit 2026
April 13-16 | The Venetian | Las Vegas
AI & Automation Workshop: A Blueprint for MSPs and Channel Partners to Drive Client Success
At MSP Summit 2026, I delivered our “AI & Automation Workshop: A Blueprint for MSPs and Channel Partners to Drive Client Success” to a room full of fully engaged attendees. The level of participation and the practical conversations that followed confirmed what many of us are seeing in the market: MSPs and Tech Advisors are ready to move beyond AI hype and deliver tangible value.
A hands-on, practical format. Rather than lecture, we worked through live examples and hands-on activities showing MSPs how to identify automation opportunities, map client processes, and build actionable roadmaps. The focus stayed on practical, low-disruption automation—and on positioning paid roadmap engagements as real consulting work, not pre-sales. Attendees left with frameworks and tools they can put to use immediately to drive client conversations and revenue.
The MSP revenue journey with AI and automation. A major theme was the full revenue arc: from initial discovery and paid roadmap engagements, to implementation projects, and ultimately to managed services and recurring revenue through Digital Assistant as a Service (DaaS). Each stage creates new value for clients and sustainable, scalable revenue for MSPs. The core message: the real margin and growth come from intentionally linking these phases together, not treating them as isolated efforts.
A team effort. Special thanks to Alex Stanton and Ashleigh Beadle for stepping up as facilitators and keeping the session interactive and on track. Although Mitch Morgan and Jayesh Kasim couldn’t join in person, their input shaped the workshop. Nathan Morris from Valenta jumped in with valuable real-world context that helped connect strategy to execution. And thank you to Robert DeMarzo, Jessica Ackerman, and Stephanie Paro from Informa for putting on a great event and making sure the workshop ran without a hitch.
Many participants asked about running similar workshops for their own clients and prospects, and requested follow-up conversations on automation strategy and digital assistant implementation. If that sounds like you, reach out—and stay tuned for the next iteration of the workshop at MSP Summit in Orlando, where we’ll share even more practical examples and use cases.
Speakers & Facilitators
Len DiCostanzo
CEO
MSP Toolkit
Panel: From Discovery to Revenue - Executing AI & Automation at Scale
Our MSP Summit 2026 panel, “From Discovery to Revenue: Executing AI & Automation at Scale,” drew a packed room and strong post-session feedback. The conversation cut through the AI hype and focused on what MSPs actually need to build repeatable revenue from AI and automation—discovery, roadmap, execution, and ongoing managed services. Five takeaways stood out:
Don’t start with AI—start with friction. The strongest opportunities surface when MSPs focus on where work slows down, breaks, or costs too much. Friction-based discovery grounds the conversation in outcomes clients already care about and makes the AI decision feel obvious, not speculative.
AI and automation discovery is real consulting work—and it should be monetized. Too many MSPs still give roadmaps away as pre-sales activity. When framed around outcomes, risk reduction, and ROI, discovery is an executive-grade decision-support engagement. Clients understand the value, and paid discovery filters out tire-kickers.
A roadmap is only valuable if it drives action. The panel agreed: a paid roadmap must include prioritized use cases, financial impact modeling, governance considerations, and a clear execution path. If it doesn’t make the next 90 days obvious, it hasn’t done its job.
Execution friction isn’t about tech—it’s about ownership and change management. Operational readiness, leadership buy-in, and practitioner adoption were the biggest hurdles between “approved plan” and real-world results. MSPs who build change management into delivery see dramatically better outcomes.
The money compounds in recurring services. One-off projects matter, but the strongest revenue came from intentionally chaining roadmaps, implementations, and ongoing managed AI services together—moving MSPs from transactional work to a compounding book of business.
Huge thanks to the panelists who brought real operating experience to the conversation: Jason Rincker (CRO, Stronghold Data), Jayesh Kasim (CEO, Valenta), Anthony Ferrigno (Chief Sales Officer, NexusTek), and Vinod Paul (President, Align Managed Services). The feedback confirmed what many of us already know: MSPs are ready for AI and automation—they just want a clearer, more practical path forward.
Panelists
Len DiCostanzo
CEO
MSP Toolkit
