It’s no surprise that this year, many companies on Deloitte’s Technology Fast 50—a ranking of Canada’s fastest-growing tech firms—are powered by or building AI tools. Take Tailscale Inc. (No. 21). It’s not an AI company, but AI is a big reason for its explosive growth, which tells us something about how broad use of large language models is affecting the economy.
Tailscale makes secure network and connectivity software for business. Earlier this year, its leaders noticed its already fast-growing revenue soaring even faster. Why? With the surge in AI usage, “the world suddenly needs network connectivity because everyone is playing with AI agents that run on their networks,” says CEO Avery Pennarun. “If you put those agents in the right network environment, you can stop them from doing dangerous things.” Plus, when executives ask AI search engines what software network product to get, “the engines literally tell you, ‘The professionals in this space use Tailscale,’” he says. (It’s true—we checked ChatGPT and Claude).
AI adoption is driving some astonishing growth. Consider Turbopuffer, founded by two ex-Shopify developers. It’s devised an efficient way for AI systems to search for answers to user questions. It’s on Deloitte’s Companies-to-Watch list because it doesn’t have enough years of revenue to qualify for the Fast 50, but with US$100 million in annualized revenue this year, it would qualify for the Enterprise-Industry Leaders, typically bigger than Fast 50 members.
Meet the 2026 Technology Fast 50
This year’s list also features heavy representation from fintechs, developers of legal software, and health- and cleantech providers. As usual, it’s an eclectic mix ranging from Flyscan (No. 8), which can detect leaks in pipelines from the sky, to Panda Hub (No. 11), which has built a marketplace for mobile car detailing, to Taiv (No. 12), whose tech lets bars and other establishments overlay custom ads on their TV screens during commercial breaks.
The Fast 50 “have been shaped by adversity and are resilient,” says Deloitte partner and program co-lead Brendan Cooper. Many were founded before the pandemic and managed to grow even as VCs pulled back following the subsequent spike in interest rates.
And five of the top six companies are led by women. “That’s a refreshing change,” says Deloitte’s tech sector leader Amanda Perran. They include SimplyAsk.ai (No. 5), an AI solution provider with big telecom clients led by Shuli Gortler, and BorderPass (No. 3), which uses AI to automate immigration and employee mobility tasks. CEO Sally Daub’s previous venture, ViXS, made the Fast 50 several times. “I’m hoping to repeat that trend,” she says.
– Sean Silcoff
Jonah Midanik was taken by the “crackling energy” in his Toronto boardroom when a pair of young entrepreneurs came to brainstorm a tech startup. Bukhtar Khan and Yilun Chen had seen how digital platforms could help small businesses enter new markets when Chen worked for Shopify. They wanted Midanik, a partner with venture capital firm Forum Ventures, to back them in applying that same logic to the healthcare space.
As Midanik watched Khan and Chen’s ideas evolve, “their drive leapt off the proverbial page for me.” When the pair zeroed in on autism care, he was sold on offering them financing.
Nearly one in 30 children is diagnosed with autism spectrum disorder, according to the U.S. Center for Disease Control (in Canada, the figure is one in 44). Khan and Chen decided to focus on the U.S. market, where each state mandates insurance coverage for autism care, and the private healthcare model offers a faster path to revenue than in Canada, where autism funding varies by province and is meted out by a notoriously slow public system. Parents told them about their struggles to find support for their children.
Meanwhile, dozens of providers complained about being “overworked and underpaid” by the private equity firms that own most autism clinics, says Khan. But clinicians were too intimidated by the risk and complexities of starting their own practices. Both sides yearned for a solution. “We want to change the system,” says Khan. “To do that, you have to align the incentives for the providers, the patients and those who are ultimately paying for it.”
Khan and co-founder Yilun Chen created Finni Health, an online platform that connects parents of autistic children with registered service providers across the U.S.
In early 2023, the duo launched Finni Health, with Khan as CEO, and Chen as president and CTO. The online platform connects parents of autistic children with registered service providers across the U.S. Since inception, the company’s revenue has skyrocketed by 46,574%. That was no surprise to Midanik. “I knew they were onto something, and we had to get them money,” he says. “We invested three times before they had any revenue.”
Today, Finni Health supports more than 1,000 clinicians, serving nearly 2,900 children in 32 states. The platform’s AI-driven software handles tedious tasks such as billing, scheduling and insurance claims, freeing clinicians to take on more patients in a segment with five times as many cases as clinics can handle.
Khan and Chen hope to bring Finni Health to Ontario next year, where more than 70,000 families are waiting for autism services. Khan hopes the company can help persuade the provinces to boost autism funding. “Autism care creates jobs for clinicians, improves the lives of children, and frees up parents and siblings to reach their own potential, contributing to overall productivity,” he says. “That our government doesn’t understand this equation drives us crazy.”
America first for Canada’s healthcare startups
Many Canadian healthcare tech companies launch south of the border first. Aside from Finni Health, which tops this year’s Fast 50 list, Vancouver-based Total Life (No. 6), a provider of online psychotherapy for seniors, and Hydreight Technologies (No. 31), whose mobile app connects patients with nurses, are currently focused solely on the U.S. market.
The reasons are multifold. Startups have far more opportunities to raise venture capital in the U.S. Plus, the U.S. private healthcare system moves faster, allowing companies to start generating revenue quickly. Aspects of the U.S. system provide further incentives. In the case of Finni, which focuses on autism care, Medicaid or insurers must cover treatments (in Canada, public funding varies province by province). Total Life, meanwhile, was drawn to cross-state consistency. “We’re a longevity platform,” says CEO Neelam Brar. While she’s proud to create jobs in Canada,“healthcare for people over 65 in the U.S. runs on a national standard—you build once and can serve every state. Canada has 13 systems.”
Additionally, dealing with Canada’s public healthcare system is rife with challenges. “You’ll die on the vine going through something like the Ontario Trillium hospital network,” says VC Jonah Midanik of Forum Ventures. “As a proud Canadian, I encourage entrepreneurs to start in the U.S. because it’s their best chance of establishing a viable business—then coming back and fixing things here.”
Recently, several institutions reined in the cash-back rewards on their credit cards. Scotiabank, for example, cut its generous 4% dividend to 1% on rent and tax payments made with its Momentum Visa Infinite+ card. Since such payments are largely possible only through the Chexy platform—a fintech that enables Canadians to use credit cards to pay bills normally not payable by card while earning rewards—you might think Chexy CEO Liza Akhvledziani Carew would be worried.
You’d be wrong.
“The fact that, in three years, we’ve been able to build a company big enough for Scotiabank to have to change a value proposition of one of their main cards means we’re probably doing something right,” Akhvledziani Carew says.
She speaks with the confidence of an entrepreneur riding a steep wave of growth. Second on the Fast 50 with eye-watering three-year revenue growth above 23,000%, Chexy already processes more than $2 billion a year in payments. In March, the company raised $14 million in a round led by a leading Silicon Valley venture capital firm.
Akhvledziani Carew’s goal is to “become the only app that you need to open to transact and manage your money.” A certified financial analyst who previously worked at Deloitte and Square, she launched Chexy in 2023 with CTO Ben Gigone and former chief product officer Abtine Monavvari.
Chexy’s customers are largely millennials with good jobs but still struggling to get ahead. “Trying to squeeze everything out of every payment you make” is part of their financial strategy, says Akhvledziani Carew. For its first 18 months, Chexy focused on enabling users to pay rent with a credit card, earning cash-back or travel rewards while boosting their credit scores. But the platform has been evolving in response to feedback from users, who pay a 1.75% fee per transaction. Early last year, Chexy added a “household wallet” for processing other bills not always payable by credit card, such as gym memberships or car leases, and annual one-offs like taxes or tuition. The company has also been attracting a sizeable SMB clientele, “which was a surprise,” says Akhvledziani Carew. The monthly card payment schedule can improve business owners’ cash flow, and Chexy’s processing fee is a tax-deductible expense.
With Chexy, Akhvledziani Carew’s goal is to “become the only app that you need to open to transact and manage your money.”
The company is using its recent funding to develop more products. In August, for example, it launched a program that rewards users with Air Canada Aeroplan points when they make mortgage payments through Chexy. The offering expands a partnership that began last year when Aeroplan added Chexy to its roster of retail partners alongside brands like Starbucks and Uber. In fact, Air Canada liked the arrangement so much, it became an investor. “There was such a synergy in their offering and the engagement that we are looking to build with our members, we wanted to help bring it to life,” says Scott O’Leary, the airline’s vice-president of loyalty and product.
Chexy has also added two credit card issuers that will offer Chexy-specific rewards—perhaps explaining why Akhvledziani Carew shrugs off Scotiabank’s cash-back cuts. One thing the company isn’t planning—yet—is expansion beyond Canada. “We have this crazy window of opportunity here, and customers are hungry for better solutions,” she says. “It would be a distraction to go after anything else.”
Fintechs transform banking ahead of the Big Six
“We’re way more conservative than Americans in adopting financial technology,” says Liza Akhvledziani Carew, CEO of Chexy (No. 2). To Canadian fintechs, trying to change that mindset represents opportunity. This year’s fastest-growing companies include an array of lateral B2B and B2C thinkers, all vying to one-up the banks with better products, services and platforms.
In the full-service realm, there’s Koho (No. 2 on the Enterprise-Industry Leaders list). Now in its 12th year, Koho is a full-service neobank with more than 2.5 million clients. At least two others, Float (No. 35) and Relay (No. 13), offer banking services specifically for SMBs. Float’s market is companies in Canada, while Relay exclusively serves small businesses in the United States.
Some startups are moving into adjacent services. Nesto (No. 9), for example, runs a consumer mortgage platform that searches the market for the lowest rates, offering advice from commission-free mortgage experts and a 1% cashback. YouSet (No. 17 on the Companies-to-Watch list), meanwhile, operates a digital brokerage comparison site for home and automotive insurance.
Maybe it’s because he’s a lawyer, but decisions matter to Benjamin Alarie. When his company, Blue J, launched an AI-based platform to answer questions from tax professionals in 2023, he monitored the tally of users who clicked “agree” or “disagree” with Blue J’s answers. Disagreement rate is key, Alarie says, because it helps the system improve over time. In its first year, when disagreements topped 1%, Alarie gave his team a challenge: “Let’s dream big and see if by the end of 2024 we can get it below 0.3%.” They hit that, and in 2025 surpassed his next goal of 0.1%.
Blue J’s other vital metrics, meanwhile, have gone rapidly up. It now has more than 6,000 subscriber firms, including three of accounting’s Big Four, and offers tailored versions of its system for the U.S., Canada and the U.K. Since launch, the platform has fielded about 13 million queries about complex tax topics, topping one million per month for the first time in August.
Blue J’s value proposition is clear. “It compresses the time for research and drafting, and liberates tax people to focus on judgment, strategy and client advice,” says Alarie. A law professor at the University of Toronto, Alarie initially took a different approach when he took a leave from his teaching job and, along with two fellow professors and CTO Brett Janssen, launched Blue J in 2015. The idea then was to train machine learning models on case law to predict how courts would rule in future scenarios. “Technically, the models were outstanding,” Alarie says. But they couldn’t answer 95% of the tax research questions that professionals had. When ChatGPT arrived in 2022, the Blue J team built a whole new system from scratch.
Since then, the company has become the market leader, says Allen Miller, a partner at U.S. investment firm Oak HC/FC, which co-led Blue J’s US$122-million financing in 2025. What puts it ahead of legacy legal software vendors and generalist AI models is its focus on tax, exclusive content agreements with leading tax publications, and an interface customized to what tax pros need. Then there’s the self-improving nature of the platform. “It becomes more precise every time it gets another question,” says Miller.
In the year since the funding boost, Blue J’s biggest transformation has been in personnel. Alarie, as CEO, has hired a president, a CFO and a product lead who all have backgrounds in scaling software and AI businesses. They’re needed, says Miller, because Blue J is “still very early in what the product could do.”
The next step on the product roadmap are workflows. This fall, the company began beta-testing a suite of automated tasks a tax professional faces once they have research in hand, such as responses to a notice from the IRS. In time, Blue J plans to offer hundreds of workflows and give its clients tools to build their own. But replacing human expertise with technology isn’t the end goal. As Alarie says: “People still need, still want, somebody to stand behind the tax filings they make.”
AI that replaces humans
Vending machines have been around since the invention of pocket change. Now, Micromart (No. 19) is betting on their power in combination with AI. By putting together AI-juiced, remotely managed pantry, fridge, freezer or hot-food vending units in an office or condo lobby, the company creates a store—minus attendants and cashiers.
Micromart is not alone. Aside from Blue J, which can replace paralegals (and, in time, potentially tax lawyers), several Fast 50 companies offer AI solutions that reduce or remove the need for human labour. For example:
SimplyAsk (No. 5): Its AI platform automates customer service, including emails and back-office processes, reducing the need for staff.
Spellbook (No. 7): Law firms can use its AI tool to automate contract drafting, review and analysis, traditionally the realm of junior lawyers.
Apera AI (No.37): Its AI vision technology gives manufacturing robots human-like sight, reducing the need for technicians to monitor or operate machines.
PAVE (No. 46): Short for professional appraisal and vehicle evaluations, PAVE enables consumers and dealers to conduct car inspections using smartphone photos, reducing the need for mechanics.
