If enterprise AI is hard, small business AI may be harder

Disclosure: I was paid by Pax8 to moderate a fireside chat with CEO Scott Chasin at the company's Beyond 2026 conference, and some of his comments from that conversation are quoted in this piece. Pax8 had no input into or review of this piece before publication. My editorial guidelines apply the same regardless.

Maybe you’ve seen the Microsoft commercial where a pizza parlor owner is puzzling over whether to bring back the $1 slice. He pulls out his laptop, fires up Excel and with the help of Copilot, generates some nifty charts to show him that he would be a fool not to. The commercial closes with a line around the block as AI has made him a working class hero. 

According to the World Economic Forum, there are approximately 400 million small and medium-sized businesses worldwide. The report states that they account for around 90% of all businesses, 70% of employees and 50% of global GDP. 

With those kinds of numbers, it's easy to think of a small business as having similar needs to their larger counterparts, just on a smaller scale. But just as children are not small adults, neither are small businesses simply small enterprises. They have a very different set of requirements. AI doesn't always turn out like you think it will, and small businesses could be less tolerant of that risk.

In a recent personal example, I asked Claude to copy an existing invoice and create a new one with new numbers, a task any invoicing software should handle easily. Instead, it kept rendering three fillable fields for my banking information in black, even though the example I provided was clearly gray. Three tries later, it still couldn’t get the field color right. Unfortunately, in this case AI didn’t speed up my business, it slowed it down. And I run into these kinds of obstacles on a regular basis.

While SMBs are clearly flirting with AI, survey data suggests they still worry about technical obstacles. That’s why many turn to managed service providers, or MSPs, to act as their outsourced IT team and handle the underlying complexity of running the business.

MSPs are responsible for updating systems and keeping them secure. In the not-too-distant future, they’ll also be expected to build agents for clients, while helping them get more comfortable using AI — or setting things up so they don’t even realize they’re using it.

Filling the trust gap

In the end, the Microsoft commercial is more aspirational than practical for many small businesses. It presents a world where you ask a question and get the perfect answer that pushes your business into new territory. Reality is much messier. A recent Goldman Sachs small business survey found that while 76% of small businesses are already using AI, only 14% have fully integrated it into core operations, half worry about security and data privacy and 73% say they need more training and implementation support.

This tracks with my own experience. The productivity payoff that vendors like Microsoft are pitching is at best theoretical. In practice, I have learned it can be hit-or-miss, and sometimes AI simply makes the process more cumbersome.

If enterprises with all their resources are running into problems making AI work effectively, that level of difficulty is going to be compounded for small businesses. I was recently at the Pax8 Beyond Conference in Salt Lake City. Pax8 is a marketplace MSPs use to buy and resell cloud and AI tools for their small business customers.

The message for the MSP audience was clear across keynotes and the fireside chat I moderated with CEO Scott Chasin: everyone needs to be using AI. Just as you would expect at a conference like this, Chasin was delivering an optimistic vision where SMBs will begin accelerating their use of AI with the help of the MSPs, who will certainly play an important role.

"We're entering this phase where AI is now useful to every business on the planet, and I think that that's a massive opportunity. I think the awakening is starting now, and so I expect as we get into next year the demand is going to come," he told me at the fireside chat. 

That's the bullish view, of course, but as my own experience shows, execution is harder than vendors want us to believe. This is especially true when it comes to SMBs where the technical hurdles tend to be magnified, imprecision and mistakes could be more costly and a lack of ROI even more impactful. 

Then there's the trust issue, which looms even larger. It's going to be a struggle to get SMBs to come along after they get a few bad answers, especially when the owner's name is on the line. The old maxim, 'once burned, twice shy' is going to come into play here.

Chasin acknowledges that trust in these tools has to be earned and the answers you get verified, but he believes if you can harness it, AI can give what he calls the "greatest cognitive shell exoskeleton" that any of us can have. "It is a superpower, but you have to learn how to use it," he said. Perhaps, but that promise still comes with plenty of friction and small business owners have to navigate that ambiguity. 

~Ron