CEO Perspective on the State of the Mid-Market (Q1) | Stratford Group

April 15, 2026

RE: What CEOs Should Really Be Paying Attention to Right Now

Dear Reader, 

Over the past few months, I’ve had dozens of conversations with CEOs, executives, and association leaders across the Canadian mid-market. Different sectors, different challenges, but I keep hearing versions of the same thing.

Growth has cooled somewhat, profitability is under pressure, and a lot of leadership teams probably feel like they are in a holding pattern, waiting to see what happens next.

To me, it's not a collapse; most aren't pulling back entirely. It's more of a recalibration while taking a step back to reassess risk, timing, and where to invest. That's understandable.

What I've found interesting, though, is where a lot of those conversations go next. Given the headlines, many turn to geopolitics. Tariffs, global conflicts, shifting trade relationships, and policy uncertainty—particularly south of the border. It's dominating the news cycle and shaping how many leaders think about the future.

These issues are real, and they do influence our markets.

But if I’m being candid, I think many leaders are over-rotating on things they can’t control, and underestimating something that’s already reshaping their business in real time: artificial intelligence.

The Structural Shift Many Leaders Are Underestimating

Over the past decade we've seen waves of new technologies (cloud computing, blockchain, automation, etc.), each with its own promise. Most arrived gradually and were adopted over time.

AI feels fundamentally different.

In many ways, it resembles the arrival of computing itself, but compressed into just a few years. The pace of improvement is rapid, and the implications extend well beyond efficiency.

We’re already seeing teams compress what used to take weeks into days, drafting client deliverables, analyzing data, preparing materials. Not perfectly, but fast enough to change expectations. Organizations adopting AI today aren't just becoming slightly more efficient. They are learning faster, improving faster, and increasingly launching new capabilities faster than their competitors.

Those advantages compound over time.

The companies that start experimenting now aren’t just getting early wins, they’re building muscle. That experience translates into better processes, new offerings, and operational improvements that widen the gap between early adopters and those that wait. Eventually, that gap becomes very difficult to close. The risk isn’t getting AI wrong. It’s waiting long enough that it doesn’t matter.

The Attention Problem CEOs Are Facing

One pattern that keeps coming up in conversations I'm having is how leadership attention is being allocated.

A lot of CEOs are spending significant time tracking macro developments like trade policy, elections, global conflicts, economic forecasts. And to be clear, those things matter. But there's very little you can do about most of them. 

AI is different. It’s accessible. It's immediate. It's something organizations can act on today. And yet many are still treating it as something to explore later, or delegating responsibility entirely to their IT departments. That's not a strategy.

AI isn’t an IT project. And it’s not something you delegate and check back on in six months. While technology underpins it, it changes how work actually happens, how decisions get made, how quickly teams move, how organizations respond to customers.

In that sense, AI is less about technology adoption and more about business transformation.

Why the Mid-Market Is Actually Well Positioned

There’s a tendency to assume mid-market organizations are at a disadvantage with something like AI. Not as many resources as large enterprises. Not as nimble as startups. But many are better positioned than they think.

Most already have:

• • • Established customer relationships,
    • Proven offerings,
    • Operational depth,
    • Leadership that can still influence change directly

Large organizations often struggle to move quickly. Startups can move fast, but they’re still figuring out product-market fit and stability. Mid-market companies sit in between and that’s a good place to be right now.

In a lot of cases, they’re close enough to their operations to make meaningful changes quickly, while still having the scale for those changes to matter.

The Leadership Imperative

If there's one point I'd push on, it's this: AI adoption cannot be something leaders observe from a distance. Leaders need to engage with it personally.

I’m not suggesting CEOs need to become technical. But I do think you need to get your hands on it. If you’re not using tools like ChatGPT, Claude, Gemini, or Copilot yourself, you’re missing context that’s quickly becoming part of strategic leadership, and you're already behind the curve.

Leaders set the tone. When CEOs lean into change and demonstrate curiosity about new capabilities, their teams tend to follow. When leaders hesitate, organizations often stall.

Many organizations are also starting to identify AI champions within their teams, people who are already experimenting and helping others understand where it can improve processes or create new opportunities. Combined with leadership engagement, this can accelerate learning across the organization.

A Final Thought for Mid-Market Leaders

One thing that has not changed in the mid-market is the importance of relationships. During periods of uncertainty and change, the trust you've built with your customers becomes even more valuable.

Organizations that stay close to their customers—meeting them face-to-face when possible, understanding their evolving needs, and clearly communicating what differentiates them—will always have an advantage.

I think AI will change how work gets done but it won't replace that need to understand your customer. The organizations that succeed will still be the ones that combine both.

One Question Every CEO Should Ask Right Now

If there is one question I believe every mid-market leader should be asking themselves today, it is this:

What am I personally doing about AI right now?

This is not something that can wait for the next strategic plan or the next budget cycle. T

Some organizations are already moving. Others are still waiting. Over the next few years, that difference is going to matter.

This is a conversation we’re having with clients every week right now; what practical adoption actually looks like, where organizations are getting stuck, and where we’re starting to see real traction.

If this topic resonates with you, I encourage you to explore some of our related pieces and to continue the conversation with us.

Jim

Jim Roche
CEO, Stratford Group