AI Adoption & Enablement Specialist

At Flynn, it's not just a job, it's a career

Before You Read Further

This role is on-site in Mississauga, five days a week. Not hybrid. Not flexible on that point.  

We are saying it first because the job is about getting technology to land with people where they actually work: at desks in our offices, and in our shops and on job sites. That is hard to do from a distance, and we would rather let you know now than three interviews in.

The Job  

Flynn installs and services roofing, glazing and architectural metals across North America. Many of our people do not sit at a desk.  

We are rolling AI out across the business right now. Claude Enterprise, ChatGPT Enterprise and Microsoft Copilot are the tools. An AI Steering Committee and an AI Tools Policy are in place; the rest of the governance is being built as we go.  

This role exists because a rollout is not a license purchase . We need someone whose whole job is getting that capability into people’s hands and genuinely used: a project coordinator, a shop foreman, a service dispatcher opening it on a Tuesday morning because it saves them an hour.  

Most of that is enablement. But not all of it. As the rollout reaches people, the requests start: someone wants a tool for a specific job, a team thinks AI could solve something. You will be the person those land with . You will take them in, work out how each one fits our existing frameworks and the tools we already have, decide what is genuinely worth doing, and then help build the ones that are.  

So, there is real administration here, and real building. What there is not, is a job that stops at "the licenses are assigned." 

You will sit in IT and report directly to our VP of Information Technology. No layers between you and the person who owns this.  

What we offer:

• Funded training and development program  


• Subsidized in-house cafeteria and gym   


• Dental and supplemental medical plan  


• RRSP contributions  


• Employee and Family Assistance Program  


• Free parking and EV Charging facility   


• Family Events and Flynn Fest  


• Sports Sponsorship Program  


• Rogers Preferred Program  


• Perkopolis Retailer Discounts 

What You Will Actually Do  

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  Get the tools into people’s hands . Plan and run the rollout, group by group: who gets access when, what they need to know first, and what has to be true before you move to the next group.  

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  Find the friction first. Sit with a team, map how the work really flows, and find where hours are disappearing. Before you talk about any tool.  

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  Run adoption like a program , not a launch . Pick the use cases, build the enablement, deliver it, and change what did not work.  

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  Build the material people will actually use : short, plain, job-specific. We run Docebo as our LMS and it is yours to use, but a two-minute video that solves one real problem beats a forty-slide deck every time.  

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  Take in the requests and sort them . As people start using these tools, the ideas arrive: some good, some not, some already solved. You will run that intake, understand what is really being asked, check it against what we already have and what our frameworks allow, and decide what is worth building.  

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  Build the ones worth building . Some of what comes in is a workflow that should be automated, or a small solution that should exist. You will help make those real, not just write them up.  

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  Build the measurement . We cannot currently answer "is anyone actually using this?" You will define what we track, get it instrumented, and report it honestly, including when the answer is disappointing.  

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  Work across the business: Estimating, Project Management, Service, Safety, Finance, and the field. This role has no authority over any of them. Influence is the whole job.  

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  Be the honest voice on AI . Every vendor is adding an AI button, and that includes the tools we already run, from Bluebeam and Autodesk to our project management and field applications. Part of this job is working out which of those are worth turning on, which need governance around them first, and which are noise.  

Who We Think Does This Well  

You have run an adoption program inside an organization : you picked an audience, built a way to get them using something, and can tell us what changed as a result.  

You have had hands on an enterprise AI assistant (Claude, ChatGPT or Copilot) not as a personal user but rolling one out to other people.  

You have enabled a mixed audience . Our people are in offices and on job sites: estimators, coordinators and finance staff at desks, and crews, shop staff and service technicians who are not. You will need to reach both, and they do not learn the same way.  

Most people who apply have only ever rolled technology out to office workers. If you have also done it for field crews , plant teams, technicians or trades, lead with it . It is the rarest thing we see on a resume and it is the part of this job that is hardest to fake.  

You drop the jargon without being asked . You will spend as much time explaining something to a site supervisor as to an IT manager. We care more that you can say it plainly than that you know the acronyms, and we will ask you to demonstrate that in the interview, so come ready.  

You have been part of a transformation program and helped shape where it went, not just delivered tickets against someone else’s plan.  

You have a bachelor’s degree in IT or a related field, or the experience to stand in for one, and roughly four to seven years in workplace technology, digital adoption, change enablement or similar.

Nice to Have, Genuinely Not Required  

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  Hands-on with Power Automate . We use it, and some of what you build will land there, but it is a part of this job, not the centre of it  

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  Microsoft 365 platform depth : SharePoint Online, Teams, governance. You will work alongside the team that administers our tenant; you do not need to be that person  

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  Familiarity with construction applications: Bluebeam, Autodesk (Revit, Inventor, Vault) 

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  Any construction, manufacturing or industrial background  

We mean it about these being optional . We looked hard at who succeeds in this kind of role and the tooling turned out to be the most learnable part. If you have run adoption well somewhere else, apply.  

What We Can Tell You Honestly  

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  This is a second seat . You will work alongside someone already doing change management and transformation here, so you will not be starting alone, but you also will not be handed a finished playbook.  

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  The decisions are made; the machinery is not built . The tools are chosen, the committee exists, the policy is written. What does not exist yet is the intake, the material and the measurement. If you want a program to inherit and optimize, this is not it. If you want to build those three things, it is.  



• We are a trades business . The technology is in service of people building physical things. If that sounds like a constraint rather than the interesting part, this is not the role.

$90,000 - $120,000 a year

#LI-AD1

Flynn Group of Companies is the leading trade contractor in North America that works on virtually every aspect of a building’s outer layer, including Roofing, Glazing, Waterproofing, and Architectural Metals. The foundation of our award winning success is having the right people on our team.

Disclosure: We use an AI-powered system to initially screen resumes. However, all applications/resumes are also reviewed by our team of Human Resources and Talent Acquisition Professionals to ensure a fair and thorough evaluation in determining a candidate’s potential fit for a role they applied to.

This posting is for an existing vacancy within the organization.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses and identifying potential inconsistencies or verification signals in application materials based on available information. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.