Blog by Ben Greenberg, VP of Corporate Development at IT Solutions 

If you’re considering M&A initiatives or navigating the challenges of growing your MSP, we invite you to connect with Ben (Ben.Greenberg@itsolutions-inc.com). 

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If you’ve been through an M&A process, you know the standard diligence workstreams like financials, operations, legal, customer dynamics, and cultural fit. These have been the backbone of deal evaluation for years. 

Over the last 6 months, AI has stopped just becoming a discussion topic and has quickly become a primary diligence workstream. This matters for sellers. Understanding what buyers are probing for, and why, can meaningfully impact deal valuation and overall business strategy. 

Why AI Is Now a Primary Diligence Focus

Investors see AI as a defining factor for MSPs over the next several years. MSPs that have properly invested in and adopted AI, both internally and from a go-to-market perspective, are best positioned to thrive in the long term. 

That same logic works in reverse. An MSP that hasn’t thoughtfully invested in AI signals a business that may struggle to keep pace as client expectations evolve and the businesses around them mature. 

Put simply, investors increasingly view AI as an opportunity for MSPs, but a risk if not approached early with a sound strategy and real investment. 

Questions Sellers Should Be Prepared to Answer

When buyers evaluate your AI strategy, they’re looking for signs of real commitment and, ideally, demonstrated results. Here are the areas where they’ll dig deepest: 

1. How do you envision your organizational structure 12 months from now — and who is leading your AI initiatives?

Buyers want to see accountability. Is there someone with authority driving the AI roadmap? The absence of a clear owner signals that either AI isn’t a priority or there’s no plan. You don’t need a Chief AI Officer, but you do need someone who owns the strategy. An executive sponsor is a great place to start. 

2. What is your AI and automation budget?

Whether in tooling, development, training, or headcount, investors will want to see that you’ve thought through the investment required to deploy AI in your organization. If it’s not budgeted, the roadmap is harder to take seriously. Be ready to speak to what you’ve committed to and what you’re planning. 

3. What are the demonstrated results to date?

Buyers will look for specifics: some examples include time saved on tickets, faster onboarding, improved GM, or revenue from AI offerings. As you implement both AI and automation tools, document the return on investment (ROI). If you’re early in the journey, that’s ok, most are. Credible roadmaps beat exaggerated claims. 

4. How are you developing a go-to-market approach around AI?

As SMB clients turn to their MSPs for AI guidance, buyers want to know if you are positioned to capture that demand. Who’s having AI conversations with clients? What’s the offering(s)? Is there a repeatable and scalable process? If an MSP is not prepared to fulfill its client’s AI demands, the client will surely look elsewhere, which is where the risk lies. In many MSPs, this will be a new, dedicated role, as the traditional vCIO or vCISO is not equipped for it. 

5. What are your tools and development strategy around AI?

Are you leveraging platforms with embedded AI? Building custom workflows? Internal resources or contractors? Buyers aren’t expecting everyone to be at the same stage, but they are expecting a strategy and pathway to positive ROI. 

 

The Bottom Line

AI diligence isn’t a passing trend; it’s becoming a major factor in how buyers value MSPs. The businesses that can demonstrate a clear, credible, and results-oriented approach to AI will command attention and higher value in a crowded market.  

You don’t need to have it all figured out. But at this stage, you do need a plan, at a minimum. 

If you’re considering an exit and want to understand how your AI strategy, or the absence of one, might impact your valuation, I’m happy to have that conversation. 

Blog by Ben Greenberg, VP of Corporate Development at IT Solutions
If you’re considering exiting your business or are navigating the challenges of growing your MSP, we invite you to connect with Ben.

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As someone who’s witnessed countless MSP owners navigate the M&A process, I’ve noticed sellers often overlook critical questions to help understand if a buyer may be the right partner for them. Here are five questions I suggest every MSP seller should ask a prospective buyer, and why the answers matter.

 
 

1. What Is Your Long-Term Vision for the Business?

Too often, sellers get caught up in the numbers and overlook the bigger picture. This question is a litmus test for the buyer’s depth of understanding and commitment to building value. A buyer who can clearly articulate plans for organic growth, investments in people and systems, and an appreciation for company culture is far more likely to be a good steward of your business.

If the answer feels vague or purely financial, it’s a red flag. Look for signs that the buyer understands the road ahead: Will they invest in developing talent? Are they planning to expand service offerings or geographic reach? Do they value innovation in an ever-changing MSP world? This question also provides insight into cultural alignment, which can make or break a successful integration.

 
 

2. What Is the Timeline for the M&A Process, and How Successful Have You Been at Sticking to It?

Ask the buyer to outline their typical M&A process, including major milestones, due diligence phases, and closing dates. More importantly, ask them how often they’ve actually met these timelines in previous deals.

If a buyer routinely misses deadlines or glosses over the details, sellers should proceed with caution. Delays can cost you money, create uncertainty for staff and clients, and signal deeper issues with the buyer’s organizational abilities. A qualified Buyer will have clear processes and a proven track record of executing as promised and within 60 days post Letter of Intent (LOI).

 
 

3. What Do Your Post-Close Communication and Integration Plans Look Like?

Successful deals don’t end at closing; they begin there. Sellers should press buyers for a comprehensive communication and integration strategy that starts well before the ink dries. Ask about a dedicated integration team and ensure a focus on both client and employee success.

Furthermore, ask the buyer how they plan to inform and engage your employees and clients post-close. Are they proactive in addressing concerns? The best integration plans are transparent and empathetic—focused not only on operational efficiency but also on cultural cohesion and retention.

 
 

4. How Will the Deal Be Funded and Structured?

The structure of your deal has direct implications on risk, complexity, and your ultimate payout. Sellers should insist on clarity regarding funding sources (cash, debt, equity, seller notes) and deal structure (asset or stock purchase, earnouts, holdbacks, etc.).

Complex funding mechanisms or uncertain sources create risk. The best deals minimize risk and maximize simplicity. It’s always best to review with an experienced M&A attorney prior to signing a Letter of Intent (LOI).

 
 

5. What Is Your Track Record?

Finally, history is often the best predictor of future behavior. Ask the buyer to describe their track record from several angles:

• Deal Completion: How often have they closed deals on the terms initially proposed under the LOI?
• Employee Retention: What are their development opportunities and how do they foster a positive culture post-acquisition?
• Client Retention: How do clients fare after the deal, and what type of support do they receive?
• Seller Satisfaction: How do sellers feel after selling to the prospective buyer? Ask for references to meet with, prior to signing an LOI

By asking these five questions, sellers can better assess a buyer’s intentions, capabilities, and suitability. Remember, the right buyer will welcome your questions and provide honest, thoughtful answers. When sellers and buyers start from honest conversations, it opens the door to partnerships that go beyond the deal and deliver lasting value.

 

 

Unlocking growth through M&A presents unique opportunities and challenges. Whether you’re planning your next acquisition or considering selling your business, we’re here to help your MSP thrive.