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Barrie & Orillia Small Businesses Can Get Free AI Coaching Through Digital Main Street

August 31, 2026 · AI & Automation

Image generated with AI.

Yes. A free, government-backed advisor program already exists for small businesses in Barrie and Orillia, and it now covers AI adoption directly. Most owners in Simcoe County have never heard of it, because it was built before AI was part of the pitch.

The program is Digital Main Street's Digital Service Squad. It puts a real person, not a chatbot or a course, one-on-one with a business owner to work through digital tools — and AI has just been added as a formal topic inside that assessment. If you run a shop, trade, or clinic in Simcoe County and have been putting off "figuring out AI" because you don't know where to start or who to trust, this is the door that's already open.

What actually changed

Digital Main Street's Digital Assessment — the structured review a squad advisor works through with you — added AI as a new topic at Level 2. That means the free coaching conversation now explicitly includes where AI fits in a small operation, not just website and social basics. The program itself is Canada/Ontario-backed and still active; it isn't a pilot that quietly ended.

Who delivers it locally

Two real, named organizations run this for our area, and both take direct calls:

• Barrie, Simcoe County and Orillia Small Business Enterprise Centre — 705-720-2445.
• South Georgian Bay Small Business Enterprise Centre, covering Collingwood, Wasaga Beach, and the wider Georgian Triangle — 705-446-3355.

Between them, an owner in Barrie, Orillia, Collingwood, or Wasaga Beach has a local, human contact for this — not a national call centre. Coaching runs up to 10 free one-on-one hours per business, delivered by an advisor, not a recorded webinar.

A practical example

Take a small retail shop on a main street in Barrie that answers every product question by phone or DM, one at a time, all day. The owner has heard "you should use AI for that" a dozen times and ignored all of it, because every pitch came from a vendor selling a subscription. A Digital Service Squad advisor sitting down with that owner for an hour is a different conversation: no product to buy, no contract, just someone qualified helping the owner figure out what AI, if anything, actually fits their day. The same holds for a trades business in Orillia buried in quote requests, or a clinic in Collingwood managing appointment reminders by hand — the coaching scope is broad enough to start wherever the owner's actual bottleneck is.

How to use this

1. Call the enterprise centre for your area — Barrie/Orillia at 705-720-2445, South Georgian Bay at 705-446-3355 — and ask specifically for the Digital Main Street Digital Service Squad.
2. Name your bottleneck before the call, not "I need AI." Missed calls, slow quoting, repetitive booking questions — a specific problem gets a specific answer faster than a vague one.
3. Ask what the AI portion of the Digital Assessment covers now. It's new enough that not every advisor conversation starts there unprompted — ask directly.
4. Use your free hours before you buy anything. The coaching is unbiased and unattached to any tool vendor, which is rare in this space — spend it before spending money elsewhere.
5. Treat it as a starting point, not a finish line. The squad will help you find direction; implementing the actual workflow is a separate step, whether that's in-house or with outside help.

The honest caveat

This program has existed for a few years, and older coverage of it leans on launch-year funding numbers that are no longer current — treat those as history, not today's budget. What matters now is simpler and still true: the program is active, it's free, it's local, and AI is now formally inside its scope. That's worth a phone call even if you end up needing more than one hour of coaching to get moving.

If you'd rather start with a second opinion before that call — or after it — that's exactly the conversation we're set up for, and it's free. Book a 30-minute chat, or read the rest of our Simcoe County AI notes.

Sources and references

• Digital Main Street Squad — primary source confirming AI was added as a topic in Level 2 of the Digital Assessment.
• Orillia CDC — Funding aimed at helping local businesses with digital needs — names the local delivery organizations and the up-to-10-hour free coaching structure.
• Digital Main Street Ontario — confirms the program remains active and Canada/Ontario-backed.