Toronto Tech Week is 4 days away. If you're still waiting to figure out your schedule, the window is closing.

Sunday May 24 at 9:00 AM - TechTO Hackathon
Rootly
Ready to see if you can build a working product using the Backboard.io memory API, ElevenLabs and Codalio tech stack?

Best for: AI builders, devs, designers, founders.

8:30 AM - TiEQuest Summit
U of T Schwartz Reisman Innovation Campus, MPR, 2nd Floor
The specific mechanics of scaling a company in Canada, taught by builders who are shipping product today and investors betting on them.The morning that sets the tone for the week. 

Best for: founders, operators, investors, builders

6 PM - The Growth Table
A dinner for growth-stage founders. The room where you can finally talk to someone who truly gets it. Application only. 

Best for: growth-stage founders

8:30 AM - Boast Funding Stage
U of T Schwartz Reisman Innovation Campus, MPR, 2nd Floor
Most founders aren't raising the wrong amount - they're raising the wrong type at the wrong time. Bootstrap to IPO, dilutive vs. non-dilutive, what's actually on the table at each stage. 

Best for: startup founders, COOs, and CFOs

4:30 PM - Beyond the Trade: A New Era for Canadian Fintech with  Questrade 
Questrade Downtown Office
A rare look inside one of Canada's most established fintech companies on what they're building, how they're scaling, and who they want building it next. 

Best for: senior developers, engineers, product managers and technical leaders

9 AM - The Silicon Valley Playbook for Canadian Founders 
U of T Schwartz Reisman Innovation Campus
What Silicon Valley founders skip that Canadians don't. Hear from a panel of Canadian founders who recently participated in Game On's San Francisco experience, then a panel of US-based VCs (Fika, Pioneer Fund, Maple VC), on whether you're playing the right game.

Best for: founders weighing the U.S. play

1 PM - People First, Product Second: A Consumer Deep Dive with Maveron
U of T Schwartz Reisman Innovation Campus
The exact behavior-shift thesis Maveron used to back a $2.4B consumer exit. 

Best for: consumer founders, operators, and brand founders

4 PM - Beyond the Bubble: An Intimate Chat with Will Hsu and Alex Norman
U of T Schwartz Reisman Innovation Campus
How to use building outside of Silicon Valley as an unfair advantage to reach a $9B IPO. Will Hsu won't speak with anyone else, so this is your one and only chance to get him live. 

Best for: early and growth stage startup founders 

6 PM - TechTO Summer Social - Powered by Wealthsimple
Bobby Bermuda's Sunset Bar, 235 Queens Quay W
600 builders, no stage time, and no pitch decks allowed at the door. We are not going to pitch you on why you should come.

Best for: our tech community!

9 AM - Market Overview: Fintech, co-hosted with Affirm
The Canadian fintech category, mapped by the operators building inside it. Approval-based.

Best for: fintech founders, operators, and builders

1 PM - Market Overview: Insurtech 
The category that's quietly compounding. Where the capital is moving, told by the people moving it. 

Best for: insurtech founders, operators, and builders

6 PM - The Quiet Part Out Loud: A RevOps Dinner
A curated dinner for the people running revenue. Real numbers, no slides, no panels. 

Best for: CRO, COO, Director of Revenue Operations, Chief of Staff, Head of Business Development of companies over $5M in revenue

🎙️ The question Kirk Simpson is bringing to the stage.

Every founder is asking how AI changes everything. Kirk Simpson is asking the opposite.

He built Wave from 2010 to 2019. Crossed $100M in revenue. Sold for $537M - the seventh-largest Canadian tech exit of the last 25 years. The customer was the same one Courtyard AI, his current company, is built for now: a small business owner trying to run something complicated without a finance team, a marketing team, or a customer service team. Different layer of the stack. Same human.

That's the credential. It is not the reason to be in the room.

The reason is the question he's bringing Monday morning, in his own words:

Read that again, slowly.

The entire conversation in tech for the last 18 months has been about what's different. Different distribution. Different headcount math. Different defensibility. Different valuations. Kirk is asking what's still true. The fundamentals that survive a platform shift. The ones that don't.

The framing matters because most of the founders sitting in this room have been told, in a hundred different ways, that the playbook they were running last year is now obsolete. Some of that is true. Most of it isn't. The hard part is knowing which is which while you're inside the company you're trying to build.

Kirk has been on both sides of that question. He built Wave through one of the biggest shifts the software industry has seen - small business software moving from shrink-wrap to SaaS to fully integrated finance - and he kept customers, kept margin, and kept building toward an outcome.

Now he's doing it again at Courtyard, in a market where the customer's discovery layer is moving from Google to ChatGPT, Gemini, and Claude in real time. The thesis is that the people who built durable companies through the last shift have a non-obvious advantage in this one, if they hold onto the things that don't change and let go of the things that do.

Which is exactly what he's coming to talk about. He has answers. He's also been around long enough to know which ones held up and which ones didn't.

And he is not the only reason to be there.

​Janet Bannister, who founded Kijiji and now runs Staircase Ventures, is in the room. ​Mike McCauley, whose Garage Capital portfolio of 200+ companies now sits at $30B+. ​Eva Lau Partner at Two Small Fish Ventures. ​Willson Cross from Borderless AI. ​Nipun Sharma from Appetronix. ​Liza Akhvledziani Carew from Chexy.

Each of them on stage, on the record, for a half-day.

TTW 2026 - THANK YOU ✨

Interested in partnering or collaborating on one of the events above? Reach out to us at [email protected] - we’re always excited to connect with organizations and brands that are a strong fit for our community.

And if you’re a CPG brand with food & beverage products you’d like featured at one of our events, we’d love to explore ways to work together. In-kind partnerships are always welcome. Email here.

📖 ALEX NORMAN RECOMMENDS YOU READ THIS

Bijan Sabet (former General Partner at Spark Capital) wrote something last month that's been making the rounds in founder circles.

The gap between what founders say about their teams and what their equity practices actually reflect, ninety-day exercise windows, shrinking option pools, vesting schedules that trap instead of reward.

PARTNER CONTENT 📌

Sage Vancouver Event - AI in Finance: From Hype to Real Impact (June 4)

AI is everywhere in finance right now. But what’s actually delivering results?

For Tech finance teams, the challenge is even greater. Between complex revenue recognition, evolving subscription models, and pressure to forecast accurately while managing cash flow, finance leaders are navigating increasing complexity every day.

Join us for an exclusive free in-person event in Vancouver on June 4 with Sarah Baldeo, and discover how modern finance teams are using AI to drive real, measurable impact.

Enjoy an evening of networking, curated food and drinks, and practical insights.

🎁 Plus: Enter for a chance to WIN tickets to see Canada at the FIFA World Cup

Eligible for CPD & CPE credits

Explore the product in action.

*this is sponsored content

Members get to our signature events for free. That's what the $249/year gets you - free access to every Together and vertical event, exclusive discounts on all member events, and a private Slack where the conversation keeps going after the event ends.

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