A dispatch from the deal room

Osler’s 2024 Deal Points Report: Venture Financings captured the state of the Canadian venture market last year, term by term, and deal by deal.

The data told one story. We asked four Osler partners to tell us the rest.

“The trends and the data points show that Canada is still an amazing place to found a technology company.”

Christian Jacques, Justin Young, André Perey, and Jacob Young help shape the deals that define the market. They work directly with startups and venture funds to structure and close dozens of financings each year. They see what slows a round, what pushes it forward, and what breaks it behind closed doors.

That gives them a uniquely sharp view of what founders are struggling with, what’s changed, and what it actually takes to get a round done in this market.

We spoke to each of them about the signals they’re watching, and what founders should carry with them into 2025.

The terms don’t lie

For André Perey, the biggest signal from the 2024 Deal Points Report wasn’t the volume of deals, it was how they were structured.

According to the report, standard venture terms remained consistent in 2024, including pari passu liquidation preferences,1x liquidation multiples, non-participating preferred shares, non-cumulative dividends, broad-based anti-dilution, and no redemption rights.

“These were not bad terms,” he said. “They’re very typical, consistent market terms. Nothing unusual.”

That stability, he argued, points to a functional, balanced market.

“During COVID, there was so much uncertainty that resulted in a lot of complicated structuring terms that were making their way into deals that by and large we did not see through 2024.”

While some companies that raised in 2021 are still navigating inflated expectations, Perey believes the broader market has corrected. 

“It’s going to take a while for everybody in the tech ecosystem to stop comparing things to 2021,” Perey said. “But don’t be under the impression that companies are not getting funded, because they absolutely are.”

Don’t let a great deal kill your next one

For Justin Young, the key issue he’s flagging for founders is a lingering mismatch between expectations and market realities, especially when it comes to valuation and control.

“I have some good companies that I work with who thought they were hitting a home run back in 2022, but found it difficult to live up to valuation expectations,” he said.

He’s advising founders to not get caught squeezing a perfect deal out of this market or fighting for a marginally higher valuation.

“Obsessing over your cap table can get you a couple points on founder dilution in your seed or Series A,” Justin Young explained. “But it can really affect your capacity to raise in subsequent rounds.”

Justin Young also noted how long it’s taking companies to actually close. “Founders tend to be optimists,” he said. “They’re used to working backwards from a launch date. But fundraising isn’t always that linear. You need to build in more time, not just to get a term sheet, but to actually close.”

He believes that founders thinking about not just the next raise, but the ones after need to focus on “speed and execution” above all else.

AI is now a story of its own

For Christian Jacques, 2024 was a year defined by contrast. 

“We were able to close rounds really fast for great companies,” he said. “But on the opposite side—with grade B or grade C companies—those rounds took almost three times longer than what it used to take.”

That unevenness shows up in the 2024 Deal Points Report, which found median close times increasing across all stages: 64 days at seed, 80 at Series A, and 70 at Series B. It wasn’t that founders weren’t getting funded, it’s that the bar to close was higher.

 AI financings were among the slowest on paper. But on Jacques’ desk, they moved the fastest. “Most of the fast-sale deals I closed in 2024 were mostly all AI companies,” Jacques said. 

The report described AI as a story of its own in 2024. The median post-money valuations for AI companies exceeded the median post-money valuations for all rounds in 2024, and while AI firms represented 18 percent of the number of financings completed in 2024, they represented 26 percent of all capital invested in 2024.

“There was a continuous frenzy with respect to AI,” Jacques added. “It now has its own set of valuations, timelines, and conditions.”

A return to consensus

In 2024, Jacob Young noticed a shift in how financings came together: lead investors weren’t willing to go it alone.

“There’s been a lot more requirement for a full syndication of—if not the entire round size—most of the round size,” Jacob Young said. “it is an incredible thing to witness where a lead investor not only believes in the company and wants to invest, but that they are able to draw a bunch of other investors to the table.”

That trend toward measured, consensus-backed rounds marked a departure from earlier years. “In early 2021, you could get a first closing done quickly and clean up the back end later,” Young explained. “Now the focus is on making sure a number of investors have reached the same conclusions about the company before we close.”

The 2024 Deal Points Report reflected that shift, showing longer median close times across all stages and more deliberate syndication. But Young doesn’t see this as a red flag, but as a return to discipline.

Amid all the noise, Jacob Young’s biggest takeaway from 2024 is that Canadian tech companies can still hold their ground.

“The trends and the data points show that Canada is still an amazing place to found a technology company and to build a business,” he said. “Last year, a lot of voters questioned whether the math still worked for building a business in Canada, but the raw talent of Canadian founders have shown it’s worth it.”

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The 2024 Deal Points Report offers one of the most comprehensive views available into how Canadian financings are really getting done.

For a deeper look at the data behind these dynamics, read Osler’s full 2024 report now.

Feature image courtesy Unsplash. Photo by Romain Dancre. All headshots provided by Osler.