Eight years ago I was sitting at home with the remains of a crumbling start-up scattered around my apartment in Saskatoon, Saskatchewan.
Video cameras. Swag. Lanyards. T-shirts. Banners. Business cards.
My phone buzzed. It was one of our co-founders, Jackie Cook. She said there was an entrepreneurship event downtown and someone wanted us to film it (we were a pseudo-media company covering local events, kind of like MTV-meets-local-news).
I did not want to go.
It was -30 degrees outside. I was burned out. The company was dissolving.
And yet…sigh. Why not? What else was I going to do but sit around feeling like crap?
I suited up, grabbed the press passes we’d Photoshopped and printed ourselves, and met our camera guy downtown.
To be honest, I don’t remember the event itself. What I do remember is meeting someone with a big, boisterous personality and an even bigger, more boisterous laugh. Brendan King. It turns out he was one of the panelists, a CEO of a local start-up called Vendetta or Vandesta or Vendazzle or something like that.
We got talking and Brendan invited me and my team to Demo Day, a weekly event at his company where people shared their personal projects, drank beer, and played foosball.
This was the invitation that changed everything.
If life were a pinball machine, that singular meeting was the accidental paddle flick that shot me straight into the bonus area where the lights start flashing and the music speeds up and the points quadruple—I just didn’t know it yet.
That Friday, my team and I went to VendAsta (which still rocked that camel case back then) and pitched our company to the 30ish employees who worked there. Brendan’s entrepreneurial spidey senses must’ve been tingling, because as soon as we sat down he casually mentioned that they were looking for a new marketing director. Before I knew it, I was having lunch at Red Pepper with him, their CMO Jeff Tomlin, and a Polish grizzly bear named Allan Wolinski.
I somehow managed to convince them to hire me, despite accidentally calling their reputation management product a CRM (a mistake which, in hindsight, was less of a slip-up and more of a prophecy) and started the job soon after.
When I told my co-founders I was leaving our “media company” for Vendasta, they were cool with it. Our business was dead anyway. The only question Jackie had, which she must’ve asked at least a dozen times, was: “What does Vendasta do?” You could tell that she didn’t quite understand the white-label thing, which, again, is hilarious in hindsight as she would not only go on to become Vendasta’s Chief Operating Officer years later but also my boss. That’s not for a while, though. For now, it’s still 2012.
The song I sang on my first Friday in front of the whole company was LMFAO’s “Party Rock Anthem” (a tradition I can’t say I’ll miss).
After that, I was part of the club. A club that included incredible social events, wicked smaht leadership, an evolving product, a loyal customer base, and an expensive order of biker jackets that we don’t need to discuss here.
That first year at Vendasta I learned more about marketing than I’d learned in four years of business school. Jeff and I doubled the marketing team as we became one of the fastest-growing tech companies in North America. Conferences were a blast. Everyone attended our social events. The sales team tripled and a new CRO from Rosetown ruffled some feathers before winning us over. Brendan even convinced me to try my hand at being a product owner, which now ranks as his worst decision ever. Life at a start-up was thrilling! Fast-paced! Personally and professionally rewarding!
And then my friends started moving to Toronto.
I got FOMO.
I made the difficult decision to leave Vendasta and move to Ontario to flex my artistic muscles. I lived with two opera singers, taught night classes at the U of T, and wrote children’s books. Spoiler: it was not a lucrative lifestyle. Just when my bank account was looking its bleakest, my phone rang.
“Hey Devon,” a voice said. “It’s Jeff Tomlin from Vendasta. Any chance you might consider coming back?”
I think I played it cool, but I was beyond relieved—not just because of the moths in my wallet but also because I’d missed Vendasta.
I went back remotely and took up a new post as head of demand gen. From there, we broke records left, right, and center. We tripled the marketing org, we started our own conference, we won countless SaaS awards for revenue growth, and, as of last year, we set a record for the most venture capital raised by a tech company in Saskatchewan.
I cannot be more impressed with the executive team and prouder of the entire organization. They are solving incredibly difficult challenges every day and doing so from somewhere that most people don’t even know exists.
That’s what makes saying this next goodbye so tough.
As of yesterday, I’ve moved on to a new challenge as VP of Marketing for another incredible SaaS company: Docebo. This next team is a force of nature—a group of razor-sharp minds, creative dynamos, and craft assassins—and I can’t wait to bring the same data-driven mindset to their marketing org that I’ve established at Vendasta. In less than a week, I can already tell they’ve got a world-class revenue org and the best platform in the industry, hands down. Transforming the learning space is going to be fun.
While I’m sad to leave one company for another, I’m energized by what’s ahead and confident that both businesses will win. And who knows? Maybe one day Vendasta will even be able to succinctly explain what they do (shots fired).
In all seriousness, thank you for the incredible ride, Vendasta. And thanks to Brendan and Jeff who made a bet on me a long time ago. I wouldn’t have made it this far without you.
Lastly, not that this story needs a moral but I’ll give it one anyway. Put yourself out there. If I hadn’t forced myself out of my apartment on a -30 degree night 8 years ago and gone to that networking event, none of this would’ve happened. In my experience, you make your own luck—and I was certainly lucky to be part of such a great team for so long.
Keep conquering local, Vendasta. I’ll be watching as Docebo dominates learning.