Ready.Set.Midmarket!: How Midmarket's 'Active' Yet 'Informal' AI Adoption Tendency Is Stalling Projects

Midmarket IT teams are struggling to deploy AI projects. As a result, some business target goals are stalling.

In this episode of Ready.Set.Midmarket!, Steve Leslie, CEO of Quadbridge -- a Montreal-based IT solutions provider and managed service provider (MSP) -- discusses the company's recent research on AI adoption in midmarket organizations.

One key finding: AI adoption is "active" in the midmarket but is "informal" -- meaning, AI projects are often launched without strategic alignment, executive sponsorship, and data governance.

Leslie weighs in on how midmarket teams can navigate cultural pushback and employee fears surrounding AI, and offers practical actions for CIOs to prepare their organizations for AI scaling success.

Topics covered:

Understanding the landscape of AI adoption in midmarket companies

The four pillars of a successful AI strategy

Recognize common pitfalls and how to avoid costly mistakes in scaling AI projects

Find out the importance of shifting from technology-focused to strategy-driven leadership

The full episode can be watched on YouTube and heard on Spotify and Apple Podcasts.

Previous RSM! episodes are here.

Transcript

Samara Lynn (00:04)

Hi there and welcome to Ready.Set.Midmarket!, the premier podcast for midmarket IT executives. I'm Samara Lynn, Senior Editor of MES Computing. Now I'm usually joined by my co-host Adam Denison. He is the Vice President of Mid-Sized Enterprise Services at the channel company, MES Computing's parent company. Adam's traveling on business currently and we look forward to seeing him on the next episode. But today we are so excited to welcome Steve Leslie. He is the CEO of Quad Bridge. Welcome Steve.

Steve Leslie (00:33)

Samara, it's a pleasure to be with you today and thanks for having us.

Samara Lynn (00:36)

thank you. And now Quadbridge just released a research paper on the state of AI adoption in the midmarket. you know, Steve, I figured we'd just jump right into it. First of all, just tell us a bit about Quadbridge for, you know, some of the folks who may not know and the reasons for developing this report.

Steve Leslie (00:54)

Yeah, so Quadbridge is a US and Canadian solution provider with a focus on helping midmarket companies implement AI at scale. connected to the report, we do a lot of research with our customer base in the midmarket space. And there's probably two touch points. We do a deep dive research, but then we produce this white paper as a result of some things we saw in our deep dive research, and we wanted to go a little further. So we ended up...working with ⁓ a group of two groups actually in two ideation sessions to create the white paper.

Samara Lynn (01:27)

What do you think were some of the three big findings from the data?

Steve Leslie (01:32)

Yeah, it's really interesting because when we did our client research, this really elevated to the top at the end of 2025 compared to previous years. And I'm talking about modernization and AI adoption. So yeah, there's probably three things to your point. There's an adoption in midmarket, there's this natural grassroots, employees want to adopt the tools, and that's very common in midmarket.

You know, the second swim lane is, you know, the head of IT wants to implement these tools and experiment with these tools. The third swim lane, is a bit rare, and it only showed up in about 10 % of our cases, is where it was driven from the top strategically. So we can talk about that as we get into the discussion today.

Samara Lynn (02:24)

I think another concept that kind of struck me with the report was this idea that in the midmarket AI adoption is active but informal. I think that's a great phrase. Yeah, do you understand that?

Steve Leslie (02:35)

Yes. Yeah.

Yeah, yeah, no.

It's very true. You know, it's interesting. I know you do predominantly work in the midmarket space and I'm sure you see this. If you look at a midmarket firm compared to an enterprise firm, the IT organization tends to be, you know, it's relatively small and midmarket's a big span of, you know, 10 million in revenue up to a billion. So, you know, these teams tend to be relatively small. So,

The informal comes from, usually somebody on the team wants to start to experiment or an employee wants to use a tool and that's how it gets introduced to IT. The other side of it is the board or the CEO says, hey, you gotta start to experiment with these tools, we wanna deploy AI. So that's where you get sort of that informal to active, because that's where we usually cross the bridge to ⁓ things stalling a little bit. Active deployment usually is, okay, they've seen some promise in some of the experimentation with the generative tools. Maybe they've deployed an agent or two, and all of the sudden they cross, I'll call it the chasm, to we want to scale agents now.

Samara Lynn (03:29)

Uh-huh.

Right.

Steve Leslie (03:50)

And that's where I would say we get into an interesting dynamic in midmarket where they have to cross the bridge to, what's our strategy for automation in the company?

Samara Lynn (03:57)

Gotcha, so what you're seeing in the report, that's coming from your own, from surveying your own customer base, which I'm largely guessing are mid-size organizations. that, okay, so this all reflects what you're seeing out there as you're servicing these companies and these organizations. Gotcha.

Steve Leslie (04:16)

Yes.

Yes, exactly. you know, one of the things I will mention, Samara, is we just came off of our QBITS event last week where we host about 150 midmarket customers and we do this annually. And in that, and this is an interesting dynamic relative to our conversation today around AI adoption and midmarket. The big priority for midmarket leaders in IT in terms of wanting to come to an event like this is not the technology, it's the leadership and the strategy skills. So it's fascinating at this event and we saw this emerge about three years ago and I think it's related to the dynamic with midmarket leadership teams in IT specifically. They're leaned on quite heavily to drive the strategy in the areas of AI adoption.

And they're sitting at the table and the expectation of IT leaders in midmarket more and more, especially as it pertains to something as powerful as automation technologies and AI is okay. You need to build a strategy company-wide to execute this. So one of the things that's fascinating about this is that

It's really viewed differently than a technology strategy. It's, how can you help us develop the organizational strategy to drive the adoption so we can drive automation across the company?

Samara Lynn (05:54)

And do you find also with your customers, you know, dealing with IT senior leaders,

Is there some difficulty pivoting from thinking like, you know, a technical person and as opposed to a business person?

Steve Leslie (06:10)

That is the number one thing they tell us prior to the event. We develop the agenda of the event based on their feedback. So we ask them, do you want to focus on? And leadership and strategy for the last three years have been one and two. So they want to learn how to sell their ideas, to gain agreement. They want to learn how to map the IT strategy to the organizational strategy. And when they're getting into conversations about AI adoption, because it is so impactful ⁓ organization-wide, that they need to develop those skills. And if I sort of go in just real quick, like the skills they need to develop specifically, they want to develop is, okay, how do I develop a strategy that I can go in front of, you know, into the boardroom and talk about? The second thing is, you know, how do I... ⁓

Samara Lynn (06:59)

Right.

Steve Leslie (07:03)

How do I gain agreement on the priorities of phasing in AI at scale and driving automation in the organization? And the third, I will put it in the category of just pure leadership skills, soft skills. How do I lead my team through change in a world where we're moving very fast and we're adopting a very exciting set of tools and technologies?

Samara Lynn (07:29)

You know, and I think that's what's so interesting to me about the quad bridge research was, and I want to go back to four pillars and you touched on them, the intent data foundation, guardrails, and leadership and culture. With that said, know, midmarket teams, have limited staff, limited resources.

If they want to nail one of those pillars first, which one should they prioritize before launching an AI project?

Steve Leslie (07:57)

Data governance and security that's the number one thing and your point on limited budgets is very, very true. We actually, do a lot of work on that about, you know, what's the capital requirements for these types of projects. And as you know, they can range like, you know, these can be investments of a half a million to $3 million, depending upon the size and depending upon, you know, the phases of the project and how far you want to go.

Samara Lynn (08:09)

Right.

Right.

Steve Leslie (08:25)

but it's a big investment. But the data, data governance and data security, number one. The other elements are very important though that we spoke.

Samara Lynn (08:35)

What's one action a CIO can take today, tomorrow, next week to avoid that? Right here.

Steve Leslie (08:41)

Yeah, so I would say when they've done their experimentation, they've done their pilots, they see a couple of wins. The costly mistake is before they go to scale, they don't engage organizational leadership on what the overall strategy is. And the big thing that we're seeing is if you don't have that in place, if you're not communicating these changes to all employees in the right way, and driving the engagement and driving the adoption, there is cultural pushback you're gonna receive. And I know that your team is aware of the pushback. There's a lot of fear around some of these tools and it has to be positioned appropriately that this is about making everybody's role easier, adopting these tools to make them you know, more productive, able to serve their internal clients and external clients a lot better. But that's probably the big thing is before you move to scale, make sure you engage at the strategy layer and make sure the cultural element is managed very, very well so that you can drive the change in the organization to adoption.

Samara Lynn (09:44)

Well, see, this is a great conversation. And I think I got a copy of that report. I guess we could share the link if folks want to take a look at it. Okay, great. We also have the...

Steve Leslie (09:51)

100%. Yeah, we can send

Samara Lynn (09:54)

Great, it's got some really great information for midmarket senior IT leadership. I suggest taking a look at it and we'll also have it on our MES computing site. Steve, this was a great conversation and so timely and so relevant. And I just, want to thank you so much for your time. So, I mean, just really great information. Thank you.

Steve Leslie (10:12)

Well, thank you for your time as well. And thank you for all the work you do. You're doing all the great work in our space and we love it. We love your support. Obviously, the pieces that you're writing and this podcast in particular is a great resource for all of our customers.

Samara Lynn (10:28)

Thanks Steve. I'll share that with the team. Thank you. Take care

Steve Leslie (10:31)

Thank you.