Here is a question worth sitting with. In your business, whose actual job is it to decide what technology you should do next year? Not who fixes things, and not who signs the cheque. Who owns the decision.
In most businesses between about fifteen and two hundred people, the honest answer is nobody. There is an IT provider who executes, an owner or CFO who approves spending, and a handful of capable people who each know their own systems well. What there is not is a person whose responsibility is the whole picture. And because the function is unfilled rather than unnecessary, the decisions get made anyway, just not deliberately.
What an absence of ownership looks like
The symptoms are specific enough to check yourself against. Nobody can state what the business spends on software and services in total, because it accumulated across departments and cards. Two or three systems do overlapping jobs, each bought by whoever needed it most urgently. A renewal arrives and the realistic options are pay it or scramble, because nobody looked at it until the notice came. A vendor demo lands and there is no technical person in the room who can tell a real capability from a well-rehearsed screen. And somebody brings an AI idea to a meeting and the discussion has nowhere to go, because there is no agreed basis for deciding what is worth funding.
None of that is an execution problem, which is why hiring a better IT provider does not fix it. Support answers the question you asked. Leadership tells you which questions you should be asking, and that is a different job.
Why this got urgent rather than merely advisable
Businesses managed without this function for years, and mostly got away with it, because technology decisions used to be slow and forgiving. You chose a server, an accounting package, a phone system, and lived with the choice for five years. Being a year late cost you a little efficiency and nothing else.
AI removed the forgiveness in both directions. On the upside, work that occupied a person for three hours a day can now be automated in a fortnight, which means a competitor who does it while you are still discussing it has a real and compounding cost advantage. On the downside, staff adopt tools nobody approved and confidential material leaves the business through a browser tab, creating exposure out of people trying to work well. Both of those need somebody with authority and judgment. Neither is a support ticket, and neither waits for a quarterly meeting that keeps getting rescheduled.
The full-time hire is usually the wrong answer
The obvious response is to hire a CTO, and for most businesses this size it does not add up. A senior technology executive in the Toronto market commands a senior executive package, and the honest truth is that a hundred-person business does not have a full week of genuine CTO work in it. What it has is perhaps two or three days a month of decisions that badly need somebody senior, and the rest is execution that other people should be doing.
Which is why fractional works here. Not as a discount version of the role, but as the right size of it. The work is a monthly leadership meeting where technology has a standing place rather than appearing only when broken, a quarterly review that re-ranks priorities against what actually changed, presence in vendor conversations, and availability for the decisions that will not keep. A written roadmap with costs and reasons attached, so choices can be argued with rather than absorbed.
The one thing that matters more than the number of days is continuity. The value of this role is accumulated context: knowing why the last migration went the way it did, which vendor overpromised, what the board already rejected. That resets to zero every time the person changes, which is why a rotating account team cannot do it and a named individual can.
If you recognised your business in the symptoms above, the useful first step is not buying anything. It is establishing what you currently spend, what you are exposed to, and the three things worth doing first. That document tends to change how a leadership team talks about technology, mostly because it is the first time all of it has been on one page. More on how we do that.