The Skydiving Problem: Why Mid-Market Companies Are Sleepwalking Through the AI Revolution
There's an old joke about two skydivers, an instructor and a student, in free-fall. As the ground rushes up, the student grows increasingly frantic. "When are you going to pull the chute?!" he screams. The instructor looks down calmly and says, "Why bother? We can just jump from here."
That joke isn't just funny. For a lot of mid-market company owners and presidents, it's a business strategy.
The Adoption Gap Nobody's Talking About
The AI story being told in the business press has two heroes and one missing character.
The heroes are the big enterprises, your JPMorgans and IBMs, who are deploying AI at scale with dedicated teams, multi-year roadmaps, and nine-figure budgets. The other hero is the scrappy startup, born AI-native, embedding it from day one.
The missing character is the mid-market company: the $10M to $500M business that is the backbone of the Canadian and North American economy.
McKinsey's research tells the story clearly. While 88% of companies now report using AI in at least one business function, the picture underneath that number is uneven. Large enterprises lead in creating dedicated AI teams, rolling out training programs, and building governance frameworks. Many mid-market companies, by contrast, have only limited proof-of-concept or pilot programs: individual employees using AI tools on their own, without a coherent organizational strategy behind them. Two-thirds of companies overall are still in the testing phase, without a clear plan for what comes next.
So why is the mid-market stuck? Three reasons, and they're all very human.
Reason One: It All Lands on the CEO's Desk
Ask any mid-market CEO what their biggest problem is. Bandwidth. Time. Capacity. There simply aren't enough hours in the day, and there isn't a deep enough bench to delegate to.
This isn't an impression – it’s documented. Gartner research found that three-quarters of organizations report their managers are overwhelmed by the expansion of their responsibilities. In a large enterprise, you can hire a Chief AI Officer, stand up a transformation team, and insulate the CEO from the day-to-day of execution. In a mid-market company, that initiative lands on the president's desk right next to the Q3 revenue shortfall, the HR problem that blew up last week, and the customer who's threatening to walk.
Inflation has been the top concern of mid-market CEOs for three consecutive years running. Interest rates are second. AI strategy competes with a very crowded agenda, and unlike a revenue problem, it doesn't feel urgent. Until it is.
The result: AI gets acknowledged at the leadership retreat, added to next quarter's agenda, and quietly deprioritized when real work shows up.
Reason Two: The Complacency Trap: "Things Are Going Well"
The second reason is harder to admit, because it masquerades as good management. Sales are up. Margins are healthy. The team is humming. Why introduce disruption into a winning formula?
This mindset has a name in organizational psychology: the success trap. And it's particularly acute in Canada.
The Globe and Mail has documented it bluntly: only 12% of Canadian firms have integrated AI into their production or services, placing Canada among the lowest in AI adoption in the OECD. Sheldon Fernandez, an AI strategist and former CEO of DarwinAI (acquired by Apple in 2024), described Canadian corporate clients as simply "very risk averse," noting it was far easier to engage companies in the U.S., Europe, and Asia in experimental AI projects than Canadian ones.
It goes deeper than individual companies. Surveys consistently find that about two in three Canadians believe their society is not inclined to take risks and has a fear-of-failure mindset. The Business Development Bank of Canada (BDC) found in 2024 that entrepreneurs are often "waiting for more concrete proof AI will help their business before investing", hesitating to be first movers.
Which brings us back to the skydiving joke. The instructor and student aren't in denial. They can see the ground. They're just comfortable enough that changing course feels unnecessary – right up until the moment it isn't.
The ground is getting closer.
Reason Three: "Strategy" Feels Like Navel-Gazing
Here's something that rarely gets said out loud: mid-market leaders are allergic to strategy work, and for good reasons.
They're operators. They're tacticians. They got where they are by getting things done: closing deals, fixing problems, moving fast. The idea of pulling their leadership team into a room for two days to talk about AI strategy sounds, to them, like a luxury they cannot afford. Time spent on frameworks is time not spent making money.
This isn't a character flaw. It's a feature. The same bias toward action that makes mid-market companies nimble and profitable is the same bias that makes them slow to do the reflective work that strategy requires.
But here's the irony: the companies that skip the strategy conversation don't avoid making AI decisions. They just make them badly, inconsistently, expensively, and without alignment. Which leads us to why this matters right now.
In the next blog we’ll talk about why moving slowly – “being Canadian-style conservative” – will (not can, but WILL) hurt you in the long run (watch this space!). But in the meantime, you can get started. Because you are not your ordinary, fearful, conservative entrepreneur. You move quickly, and this 2 minute video will get you started.
https://www.youtube.com/watch?v=AkKSQd7ehIY
*Sources: McKinsey State of AI 2025; Gartner CEO Survey 2025; Gartner HR Leader Survey 2024; Gartner Cybersecurity Leader Survey 2025; Capstone Partners Middle Market Business Owners Survey 2025; Business Development Bank of Canada 2024; Globe and Mail, August 2025; World Economic Forum, January 2026.*