Len's Reflections from ITEXPO #TECHSUPERSHOW
I am just back from ITEXPO #TECHSUPERSHOW and still thinking about the Coaching Café conversations.
(And the view from my room!)
What struck me wasn’t how different the businesses were — it was how similar the challenges sounded across the 20+ MSPs, vendors, consultants, and AI startups I met with.
The Themes That Kept Coming Up
AI and Automation: Where Do We Start?
AI and automation is clearly a priority — but most teams are stuck at “where do we start?”
Coaching tip: Don’t start with tools. Start with one manual process you already measure and look to apply an ai powered automation solution to that first.
Turning Expertise into Repeatable Revenue
A lot of very capable operators are struggling to turn expertise into repeatable revenue.
Coaching tip: If your best people are required for every sale, you don’t have a service — you have heroics.
From Product + Training to Outcomes + Enablement
The channel is shifting from product + training to outcomes + enablement.
Coaching tip: If your partner motion doesn’t help someone close a deal faster, it’s not enablement.
MSPs as Platforms, Not Just Providers
MSPs are evolving beyond service delivery into platforms that manage risk, decisions, and results.
Coaching tip: The more value you create upstream (assessment, prioritization, governance), the less price pressure you feel downstream.
What People Were Really Looking For
And maybe most important…
People weren’t looking for pitches — they were looking for clarity.
What to focus on.
What to ignore.
What actually works right now.
That’s why the Coaching Café format works. Real conversations. Real context. Real pattern recognition.
A Special Thank You
A special shout out to Valenta and Jayesh Kasim for sponsoring my coaching sessions and hosting a few meals to talk about AI powered automation and Digital Assistant as a Service (DaaS). Let me know if you want to hear more.
Thanks to ITExpo, Channelwise and the Coaching Café team for creating the space – and to everyone who sat down and shared what’s actually happening in their business.
If we talked at IT Expo, great meeting you.
If we didn’t, the conversation is always open.
Len DiCostanzo
CEO of MSP Toolkit