You started SAAS NORTH with 400 attendees from 200 companies, watching what was happening in the US and betting Canada needed its own version. What did you get wrong in that first year that you had to fix fast, and what’s the one thing from that original format that’s survived unchanged to today’s 2,000+ person event?
David Tyldesley: Honestly, nothing went wrong… …(that attendees would have known about!) Wait, we did have important and expensive physical signage that was sent by train (for some strange reason) and it never arrived on site for our first event. Many thousands of dollars and more importantly, no signs.
We found a local company to reprint almost everything in 12 hours. It was a miracle. Oh yah, and then there were the 10 or so speakers that had flights cancelled due to a snowstorm and we created on-the-spot impromptu roundtables to replace the sessions!
Honestly though, SAAS NORTH AI, the first edition, still stands out as one of the best conferences I’ve ever run.
The event has grown alongside and had to keep pace with some very different eras of Canadian tech: the SaaS boom, the 2022 downturn, and now the AI wave. How do you decide when a shift is real enough to reorient the conference around, versus just noise you should let pass?
David Tyldesley: You’re missing a BIG one – COVID! We ran one of the first large-scale virtual conferences in Canada (we had no idea what we were doing), and then as restrictions lifted, we had the largest in-person conference in the country since lockdown (900+ people in person in November of 2021).
But to answer your question – it’s all about listening to the customer – every one of our 11 editions so far (including the upcoming) is shaped by a steering committee of SaaS and Ai entrepreneurs and investors.
Rebranding toward AI and launching DEPLOY as a dedicated defence and dual-use tech summit is a notable pivot; dual-use wasn’t exactly a comfortable category for Canadian startup culture even a few years ago. What changed, either in the market or in your own thinking, that made this the moment to build that stage?
David Tyldesley: Two things changed at once, the market and me. For years “defence” was almost a dirty word in Canadian startup circles, foundersthought it was off-brand or off-limits and I certainly wasn’t a priority.
That’s flipped fast: between the geopolitics, Canada actually committing to spend on defence, and the fact that so much of what founders already build (AI, autonomy, cyber, logistics) is inherently dual-use, it went from taboo to urgent.
On my own side, I also felt that the fact we were already in Ottawa was like a secret weapon (pardon the pun). So we ran a focus group with folks from ACDC, Cove/NATO DIANA, Anvil and BDC, and the message was unanimous: Canada needs a founders’ room that tells the truth about dual-use and defence.
That’s DEPLOY. We want to normalize discussions around defence and dual-use opportunities. Frankly, if a chunk of the room leaves saying “this isn’t for me,” we’ve done our job.
DEPLOY is explicitly for founders and investors navigating dual-use opportunities. What are you hearing from that audience right now is the appetite coming more from founders looking for a new customer base, or investors looking for a new thesis?
David Tyldesley: Honestly both, but they’re coming through different doors. Founders are the louder voice right now, a lot of them already have a product that’s quietly dual-use and are realizing defence and government could be a serious new customer base; they just don’t know how the buying actually works or whether they’d be any good at it.
Their question is practical: “is this my market, and what would it take?” What I love is DEPLOY puts both in one room and forces an honest conversation. If I had to call it: founder curiosity and ambition is filling the room, but investor conviction will decide how big this gets.
After more than a decade running the event, you’re in a fairly unique position: you’ve watched thousands of Canadian founders and investors up close, year over year. What’s the biggest change you’ve seen in how Canadian founders talk about ambition building for Canada versus building to compete globally between that first 400-person event and now?
David Tyldesley: The ceiling is gone. In the early days a lot of founders talked about being the best in Canada, “win the domestic market first” was the default and going global was a scary someday, there was a real quiet-Canadian modesty to it.
Now the best founders assume global from day one. They benchmark against the top companies in the world, not the top in Toronto or Vancouver, and they talk about category leadership and real outcomes without flinching.
Part of that is the wins we can now point to, Canadian companies that scaled and sold for real money – and that pumps more money back into the startup ecosystem and back into funds. The shift from “build for Canada” to “built here, competing globally” is the single biggest change, and it’s been fun to watch.
To attend SAAS North – November 4 – 5, 2026 – Rogers Centre, Ottawa
