SMBs face unique IT roadmaps that AI can further confound

A few years ago, life provided an exit from the enterprise world where I had spent most of my 25 years leading IT departments, dealing with budgets, strategic planning, and committee and board meetings. I was for many years the IT head of a global professional services and investment management company that specialized in real estate services and engineering until one day I was suddenly out on my own.

While my experience in advanced digital transformation and developing client-centric digital solutions could have led to a leadership position with another global company, I decided instead to steer my course and talents to small and medium businesses (SMBs), which do not typically have internal strategy committees or the financial wherewithal to have an army of external business and technology consultants on retainer. Most SMBs, I discovered in my research, do not plan three years ahead. Instead, technology decisions are made between customer calls, in late-night bursts of improvisation, and often with a quick search or advice from a trusted local IT expert.

The state of SMB IT

Many SMB owners, at least the ones I talked to, are also not familiar with the concept of a “data governance framework,” a “digital transformation strategy,” and other terms that are routinely dropped and discussed at enterprise IT meetings and water cooler chats. I discovered in my research they have a language all their own, although familiar patterns are there. For example:

• Survival mode: Spreadsheets, shared inboxes, duct tape. It works until it doesn’t.
• Growing chaos: The business outgrows the tools. Leaders feel they are losing control.
• Tool overload: Teams pick their own apps. Integration disappears.
• Visibility gap: Risk and accountability rise. Leaders need a single view of reality.
• Looking ahead: The basics are under control. Attention shifts to innovation and speed.

Many, as I discovered, are not too sure who or what is a CIO or that person’s related responsibilities. However, they are concerned with some of the same things that keep enterprise IT leaders up at night: “unmanageable chaos,” wasted time and money, and AI — not the elaborate and expensive initiatives explored by much larger companies, but the kind that would allow them to create less expensive custom applications.

Even without a clearly labelled IT budget, SMBs are already spending real money on technology. Total SMB IT spending will exceed $2 trillion by 2027 and reach $2.34 trillion by 2029, with growth accelerating through the period (Pannala & Lin, 2025). So, the real problem isn’t money. The problem is clarity, or in corporate speech, strategy. Without a clear path forward, that spending goes to the wrong tools or to the right tools in the wrong sequence.

One of the biggest concerns for SMBs in capital acquisitions is integration. Many rank automation as the top priority, yet almost half say connecting new tools to the old ones is one of their hardest tech problems. They are now planning to invest in fixing it and want vendors to ship connectors that actually work. A simple map would make these choices easier and stop the swirl. With a shared map, the same budget works harder, and the business moves faster.

Acknowledging the liabilities of AI

But what about AI? Wouldn’t that fix it? AI is not just another tool. It changes the economics of work, the pace of change, and the risk surface.

First, it lowers the barrier to automation and analysis. Forty percent of US small businesses report using generative AI, nearly double the 2023 level. Top uses are marketing, customer insights, and customer communications. Among AI users, 91% say AI will help future growth, 86% report efficiency gains, and 89% say it makes running the business more enjoyable, according to a report from the US Chamber of Commerce’s Technology Engagement Center.

Second, it pushes the integration problem to the front. AI is only as useful as the data and process plumbing you connect it to. With tool overload, AI is sugar on top of a mess. It helps for a moment, then the mess gets worse. SMBs themselves say the integration tangle is a top blocker and are prioritizing fixes.

Third, it raises the stakes on governance. Models generate content, make suggestions, and even take action. If you do not control inputs, prompts, and outputs, you will ship errors at scale. Many SMBs worry about compliance and are not ready for a patchwork of AI rules. Only about a third of SMBs feel very well prepared to comply with new requirements, and most expect real challenges. So yes, AI helps. It also punishes. In plain terms, AI multiplies whatever you already are.

Filling the leadership void

This made me think about who should make all these decisions? SMB owners, as well as hired leaders of larger SMBs, are already busy individuals wearing multiple hats. Most of the time, IT operations are outsourced to MSPs, and nobody is in charge of the bigger picture. Younger teams are more fluent with digital tools. Forty-five percent of SMEs led by CEOs aged 65 or older lack a clear digitalization process, versus only 11% with CEOs aged 25 to 34.

Younger leaders are much more likely to rely on platforms and to use bottom-up experimentation (Bianchini & Sancho, 2025). But tool fluency is not the same as building a reliable system. The most challenging aspects remain process design, integration, data quality, change management, and risk management. In short, there is a clear need to bring all these together under a cohesive digital adoption plan.

The enterprise has ITIL, COBIT, TOGAF, CMMI, and a gazillion of other frameworks to guide them. The SMBs do not need to copy; they have their own reality and need their own map. The five phases show up everywhere I go. The fix is not more software. It is better sequencing and clearer choices. AI makes the payoff bigger. It also makes the downside of poor choices bigger.

If you are an SMB leader, do not ask which tool to buy next. Ask which phase you are in and what the next right step is. If you are an advisor, stop selling tools and start creating clarity. If you are a vendor, admit that your product does not fix strategy and help your customers build the basics first. Technology should make your business better, not busier. AI can help you get there, fast. Only if you are clear about where “there” is.