MSP Summer School 2027: The AI MSP Make the Successful Transition

For a number of years I’ve run an MSP Summer School during January.

For January 2027, I want to tackle what I believe is one of the biggest changes the MSP industry has faced:

The transition to becoming an AI-enabled MSP.

AI isn’t simply another product that MSPs need to understand so they can sell it to customers.

I think the change is much bigger than that.

For the past 20 years, MSPs have helped customers navigate major technology transitions. We’ve moved customers from servers to cloud, perpetual licensing to subscriptions, on-premises infrastructure to Microsoft 365 and traditional security models towards Zero Trust.

This time, the MSP itself needs to make the transition.

That’s what the 2027 MSP Summer School will be about.

The AI MSP: Make the Successful Transition

The plan is to run four live online sessions during January:

Date	Time
Wednesday, 6 January 2027	10:00 am–12:00 pm AEDT
Wednesday, 13 January 2027	10:00 am–12:00 pm AEDT
Wednesday, 20 January 2027	10:00 am–12:00 pm AEDT
Wednesday, 27 January 2027	10:00 am–12:00 pm AEDT

That’s eight hours across four Wednesday mornings, with a week between sessions to take what we discuss, try it inside your MSP and come back with the results.

The program will follow a simple progression:

Understand → Build → Sell → Operate

This won’t be eight hours of AI theory.

The objective is to help you start building the AI-enabled version of your MSP.

Week 1: The AI MSP

What does an MSP need to become?

We’ll begin with the strategic question.

What does AI actually mean for the MSP business model?

We’ll look at areas including:

how AI changes the way an MSP operates
where existing MSP revenue may come under pressure
what customers will increasingly expect from their technology provider
AI-enabled service delivery
Microsoft 365 Copilot, agents and automation
opportunities for new recurring services
moving towards managed business outcomes
Shadow AI, security and governance
assessing your current AI maturity

The objective will be to start creating an AI MSP Transition Map for your business.

Week 2: Build the AI-enabled MSP

Use it yourself before you try to sell it

I strongly believe MSPs need to start using AI internally before attempting to advise customers on their own AI transformation.

We’ll therefore get practical.

We’ll look at opportunities across:

service desk
technical documentation
sales
marketing
proposals
account management
customer reporting
project delivery
security
administration
knowledge management
business process automation

We’ll also explore technologies such as Microsoft 365 Copilot, Copilot Chat, Copilot Studio, agents, Power Automate, Azure AI, RAG, private/local AI and MCP.

One question will feature heavily:

Would I currently pay an employee to do this manually?

If the answer is yes, we should at least investigate whether AI can assist, accelerate or automate some of that work.

The objective will be for each participant to identify at least 10 processes inside the MSP that could potentially be redesigned using AI.

Week 3: Selling AI

How do we turn this into revenue?

Using AI internally is only half of the opportunity.

The next challenge is turning AI knowledge and experience into something customers will actually buy.

I don’t think simply offering “AI consulting” or “prompt engineering” is enough.

We need packaged outcomes.

For example:

AI Readiness Assessment
AI Governance Foundation
Microsoft 365 Copilot Readiness and Deployment
AI Productivity Workshop
Business Process Automation
Custom AI Agents
Managed AI Services

We’ll work through customer discovery, demonstrations, packaging, pricing, ROI and the increasingly common objection:

“We’re already using ChatGPT.”

The goal will be for every MSP to leave this session with the foundations of three AI services that could be taken to customers.

Week 4: Operating the AI MSP

Turn the ideas into action

The final week brings everything together.

We’ll explore areas including:

AI governance
customer data protection
identity and access
Microsoft Purview
DLP
Shadow AI
agent governance
human oversight
AI acceptable-use policies
quality assurance
measuring AI ROI
developing staff skills
internal AI champions
continuous improvement

Most importantly, every MSP should finish January with a:

90-Day AI MSP Transition Plan

That could look something like this.

Days 1–30: Adopt

Start internal AI adoption, establish governance, train staff and identify repeatable use cases.

Days 31–60: Build

Package offerings, create demonstrations, establish pricing and identify pilot customers.

Days 61–90: Sell

Deliver pilots, measure results, capture case studies and start converting successful projects into managed services.

The question at the end of Summer School will be very simple:

What is your MSP going to do differently on Monday morning?

Constant Recording. Constant Iteration.

There’s another idea I want to explore throughout Summer School.

Record → Analyse → Improve → Repeat

Subject to appropriate privacy, consent and governance, MSPs generate enormous amounts of useful information every day:

customer questions
support interactions
meetings
sales conversations
customer objections
procedures
documentation
repetitive tasks
successful prompts
failed approaches
automation opportunities

Historically much of that information disappeared as soon as the conversation or interaction ended.

AI potentially changes that.

Activity can become knowledge.

Knowledge can produce insight.

Insight can drive automation.

Automation can produce better processes.

That leads to a principle I want to explore throughout Summer School:

Constant recording. Constant iteration. Constant improvement.

You’ll be doing, not just watching

I don’t want this to be four webinars where everyone watches presentations for two hours.

Each session will combine:

current AI developments
key concepts
live demonstrations
MSP-specific examples
practical workshops
group discussion
take-home challenges

There will also be work between sessions.

After Week 1

Identify 20 repetitive activities inside your MSP.

After Week 2

Select five and experiment with AI.

After Week 3

Have an AI-focused conversation with three customers.

After Week 4

Choose one AI service to launch.

The goal isn’t simply to attend Summer School.

It’s to start building your AI MSP during Summer School.

What will it cost?

I’m proposing to price Summer School per MSP rather than per person.

That’s deliberate.

I’d much rather an MSP owner bring a technical lead, service manager or salesperson along so that multiple people inside the business understand what needs to change.

Each registration will therefore cover up to three people from the same MSP.

Proposed pricing

Registration	Price + GST	Saving
Standard	A$895	–
Patron member	A$795	A$100
AI Dojo member	A$745	A$150
Patron + AI Dojo member	A$645	A$250

For those who are members of both Patron and AI Dojo, you’ll receive the special combined-member price rather than having to work out multiple overlapping discounts.

Member prices won’t stack with other promotional offers.

I’m also considering an additional post-Summer School implementation clinic for people who are members of both Patron and AI Dojo.

What’s included?

My current plan is for registration to include:

four live two-hour sessions
up to three participants from the same MSP
session recordings
practical worksheets
templates
AI MSP planning resources
AI service development frameworks
exercises to complete inside your MSP
your own 90-Day AI MSP Transition Plan

The emphasis throughout will be firmly on practical outcomes rather than AI theory.

Who is Summer School for?

I’m designing this primarily for:

MSP owners and principals
practice managers
technical leaders
service managers
sales and business development leaders

You certainly don’t need to be an AI expert.

In fact, that’s rather the point.

If you’re asking questions such as:

What does AI actually mean for my MSP?

Where should I start?

How should we use AI internally?

What AI services should I take to customers?

How can we make money from this?

How do we manage the security and governance risks?

How do I stop AI becoming another technology distraction?

then this is exactly the sort of program I’m planning.

Interested? Register your interest now

At this stage I’m asking MSPs to register their interest.

There’s no commitment simply from expressing interest. It will help me gauge demand for the January program and keep interested people informed as the final agenda, registration arrangements and supporting material are confirmed.

Register your interest in MSP Summer School 2027

If you’re considering joining me in January, register your interest now so I can keep you updated as the program takes shape.

The goal

I’m not going to promise that eight hours of Summer School will magically transform an MSP.

I think there’s a much more useful objective.

By the end of January, I want participating MSPs to understand:

Where they are now.

Where AI could take their business.

What they should use internally.

What they could sell to customers.

What they shouldn’t do.

And, most importantly:

What they are going to do next.

Because the basic premise behind Summer School 2027 is straightforward:

MSPs have spent the last 20 years helping customers make successful technology transitions.
Now it’s our turn.