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Sept 28-30, 2026
Loews Royal PacificOrlando, FL

2026 Agenda

Monetizing AI MSP Workshop: The MSP Playbook for Scalable Success

Len DiCostanzo  (CEO, MSP Toolkit)
Chance Weaver  (Vice President of AI Adoption, Pax8)
Location: Coral Sea 2
Date: Monday, September 28
Time: 1:00 pm - 4:00 pm
Pass Type: Summit Pass
Session Type: Workshop
Vault Recording: TBD

The enormous interest in AI is creating new demands for guidance, governance, automation, and ongoing support. Yet many MSPs have not fully established themselves as their clients' trusted AI and automation advisors. That results in missed opportunities for consulting revenue, implementation projects, and recurring managed services. In many cases, clients are experimenting with AI tools, building automations, and making AI decisions with little or no MSP involvement.

In this interactive workshop, Len DiCostanzo, CEO of MSP Toolkit, and Chance Weaver, global VP of AI adoption at Pax8, along with other leading MSP experts and peers, will share a practical framework that MSPs can use to position, sell, and deliver AI and automation services that drive measurable client outcomes and profitable business growth.

Rather than focusing on individual AI tools, this workshop emphasizes building a repeatable client engagement model that helps MSPs transform AI interest into business value, actionable roadmaps, and multiple revenue streams. Attendees will learn how to move beyond informal AI conversations and establish structured, billable services that clients recognize and value. Participants will discover how to identify the right opportunities, facilitate executive-level AI and automation discovery conversations, uncover productivity, process, and governance challenges, and develop an AI and Automation Execution and Investment Plan that aligns technology investments with business objectives.

This interactive, vendor-neutral educational session introduces a proven engagement model designed to help MSPs uncover opportunities across three high-growth service areas: AI productivity tools, AI-powered automation, and AI governance and security. Through real-world examples, audience discussion, and practical guidance, participants will gain insight into how a single AI and automation engagement can lead to consulting revenue, implementation projects, recurring managed services, and deeper strategic client relationships.

This session offers key takeaways for all partners, whether just beginning an AI journey or looking to expand an existing AI practice:

  • Learn how to position your MSP as a trusted AI and automation advisor before clients seek guidance elsewhere
  • Understand how to identify, prioritize, and roadmap AI opportunities across productivity, automation, governance, and security
  • Discover how to convert AI assessments into consulting revenue, implementation projects, and recurring managed services
  • Explore practical delivery models, including building capabilities internally, leveraging strategic partners, or combining both approaches
  • Leave with proven frameworks and actionable ideas to accelerate the growth and profitability of your AI services practice.