toronto
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Jason Field built the school he wanted to attend
Before BrainStation, Jason Field wanted enough digital knowledge to lead a team. Building a place to learn became a career of its own.
Matt McInnis and the expensive art of learning by doing
A Blue Jays ticket experiment helped him get into IBM. A classroom problem helped him leave Microsoft. The Typist founder keeps finding reasons to build something.
Typist makes the office a practice room.
Inside a simulated office, the humble business letter becomes a test of judgment. Typist turns keyboarding and document production into skills students can practice, measure, and use.
Riyaz Somani and the Expensive Art of Doing Less
From Cirba’s server analytics to Kubex’s Kubernetes and GPU optimization, Riyaz Somani has stayed with one problem: getting more useful work from the computing power companies already pay for.
Rowan Saunders’s long bet on getting bigger
A summer job led Rowan Saunders into insurance. Decades later, the Definity CEO has taken a mutual insurer to the stock market and completed a C$3.3 billion acquisition. The next test is making the pieces work together.
Josh Wong’s Unfinished Business With the Grid
Josh Wong sold his first grid software company to GE, then returned to the same demanding customers with ThinkLabs AI. His career is a study in what happens when an engineer finds a problem he cannot leave alone.
Shawn Rusich knows what happens before the party
From Paris fashion offices to Toronto food launches and a Los Angeles expansion, the SUGO Communications founder has built a career around getting people into the room. Keeping the business running takes another kind of attention.
Dmytro Piskaryov’s second set of instructions
He helped build Netpeak from the inside, moving from PHP development to the CEO’s chair. Now, in Toronto’s nonprofit sector, Dmytro Piskaryov is putting his experience with systems and people to a different use.
Daniel Shimmerman Knows the Org Chart Is Only Half the Story
Varicent's co-founder built a business around the mechanics of selling. His career since IBM's acquisition - and a podcast about parenting across generations - reveals a lasting interest in the people behind the process.
Art Mandalas and the afterlife of a club flyer
Before Community Agency made campaigns for an NBA team, Art Mandalas was making flyers for Toronto nightlife. His work has grown into new rooms, new disciplines and new technologies, with the city still close at hand.
Kevin Strain went east. His ambitions grew.
Five years in Asia changed how Kevin Strain thought about leadership. Now Sun Life’s president and CEO is applying those lessons to a business whose reach extends well beyond its Canadian roots.
Paul Cosgrove and the work between the promises
Before leading Assurant Canada, Paul Cosgrove spent 25 years inside the business. His career runs through the less glamorous work of insurance: claims, client relationships, implementation and the people who make a promise hold.
Joe Kindness and the idea that outgrew the kitchen table
Before AgencyAnalytics served 7,000 agencies, Joe Kindness and Blake Acheson considered turning website visitors into fish. The business they built instead would ask rather more of its founders than knowing how to code.
Shawn DeSantis’s very big bet on staying local
He spent a decade bringing Canadian brokerages together while keeping their local identities. Now Shawn DeSantis is putting one name above the door - and asking the relationships underneath it to do the heavy lifting.
Alex Vasylyk and the People Who Stay
From Ternopil to Toronto, Alex Vasylyk built a career across borders. At StartupSoft, the enduring question is how to make people on the other side of a screen feel like part of the same company.
Kevin Bache and the Distance Between Code and Pyrotechnics
A game-building hackathon, an international pitch trip and a Super Bowl commercial: Kevin Bache’s route to co-leading Phoenix runs through the places where software meets an audience.
Gavin Thompson and the business of keeping things moving
Before Phoenix raised CA$50 million, Gavin Thompson had spent years building software for other companies. An overnight delivery fix offers a useful glimpse of the founder he became.
Tal Hayek’s Second Act Starts With an Unfinished Plan.
He built AcuityAds, renamed it illumin, and handed over the controls. Back as CEO in 2026, Tal Hayek is testing a stubborn idea: advertising should be as easy to follow as the plan on the wall.
Alexandr Dudarev and the price of half an hour
The Insurance Supermarket founder built a business around getting people to an insurance conversation sooner. His career traces the promise, the revisions and the responsibilities of making an old transaction move faster.
Todd Godin Built the Business. Then He Changed What It Made.
From three people in a Markham townhouse to an automated production floor, Todd Godin spent decades turning retail ideas into things people could touch. His next challenge was handing the company on.
Ernie Crawford and the unfinished business of the printed page
He chose computers over the family hotel tradition, then built a company around the documents everyone else takes for granted. Three decades later, Ernie Crawford is still finding work hidden inside an ordinary envelope.
Michael Serbinis and the advantage of starting over
He helped build Kobo into a rival to Amazon, then went back to the beginning at League. Michael Serbinis’s career is a study in choosing difficult problems - and finding people willing to solve them together.
Ellis Jacob and the business of getting people out of the house
He came to Canada for a wedding, built Galaxy around overlooked cinema towns, and spent 23 years leading Cineplex. Ellis Jacob’s career turns on a question that still matters: what makes an evening worth going out for?
Mike Murchison and the art of answering
Before building Ada, Mike Murchison and his co-founder joined seven customer service teams. The experience still shapes how he builds software, leads people and thinks about AI.
Bryn Jones and the business hiding inside a bad idea
A struggling collaboration app gave Bryn Jones an unexpected education in selling software. The useful part became PartnerStack - and, eleven years later, a new chapter with AppDirect.
Mandle Cheung and the price of a second beginning
He built ComputerTalk from a basement room. Decades later, Mandle Cheung hired an orchestra to learn Mahler - and discovered that a second beginning could make rather more noise than the first.
Marc Altshuller and the unfinished business of Varicent
He helped build Varicent, stayed when IBM bought it, then helped buy it back. Marc Altshuller’s second act follows a question that has occupied much of his career: how do you turn business data into better decisions?
Top Hat found the classroom’s missing reply.
A lecture can reach hundreds of students and still miss what they understand. Top Hat built a business around getting an answer back.
Richard Nelson sold the house. Then he rebuilt the roofing business.
A third-generation roofer, known as Richy, traded a Toronto roofing career for a software startup. The work that followed has been an extended lesson in what contractors will actually use.
Morris Shawn and the business of staying in touch
He started with airport phone rentals. Three decades later, Roadpost’s founder and chairman is helping steer a business built around a small, stubbornly human need: getting a message through.