Ceridian CEO David Ossip Has Made Culture His Purpose, and Purpose His Culture

If David Ossip is interviewing a new hire, there’s one question he will always throw in.

“What are your top two interests outside of work?”

That question captures the essence of Ossip and his company, Ceridian. Successfully scaling a company is all about creating a nuanced work-life balance. But what about Ossip’s answer to his own question?

“Well, I have a bike and kids,” he says. “I travel three to five days a week, so when I’m home I want to spend time with my family, and one of the best ways to get around cities is to make sure you have a bike to use.”

That answer—just like the question itself—shows why Ceridian is thriving in the global tech ecosystem right now. Carving out time to spend with loved ones and staying on top of goals (both personal and business-related) are parts of what defines Ossip’s take on culture, and culture is the most important thing to him and his business.

Building and Building and Building

You could say Ossip is an entrepreneur. Or you can look at the sheer number of businesses he has created, scaled and undergone exits with, and figure it out yourself.

Most people would start with Ossip’s company Dayforce being acquired by Ceridian in 2012 for nine figures, one of the larger non-IPO exits in Canadian tech history. Or they might go to his recent record-setting Canadian IPO. But to get a true sense of his work ethic, it takes a bit farther back of a trip than 2012.

Ossip graduated from the University of Toronto with a degree in econometrics and decided he was going to be an accountant. It didn’t go well. Ossip lasted all of 15 minutes at his first job, walking out of the orientation without ever looking back.

He eventually found work at CIBC, but they had nowhere to put him at first. As Ossip sat at his desk, he would check out what his colleagues were working on. The guy seated next to him was working on a task that would take a few months, according to his outline. Ossip leaned over and showed him a shortcut, turning those months of work into days.

“CIBC thought I was this genius,” he laughs. “I wasn’t.”

CIBC moved Ossip to a special project where he could find more time- and money-saving techniques. He found some, but the bank never listened, so Ossip wrote a piece of software on his own. He ended up selling that software to CIBC, which gave him enough money to fund his way through Harvard Business School.

After obtaining his MBA, Ossip took a bit of a different route than most. After a tech-scouting trip to South Africa, Ossip founded Business Machine Interfaces and worked with clients like Toyota and Siemens. It was acquired by the Japan-based Amano in 1997, and Ossip worked with them for a year before leaving.

He wasn’t done yet. After a year spent waiting out a non-compete clause, Ossip founded Workbrain in 1999 and helped it grow to over $100 million in four and a half years, It went public in 2003, then was acquired by Infor Global Solutions in 2007.

If you’re keeping count at home, that’s three acquisitions so far. After another period of a non-compete clause—which seems to be the only real thing that can slow him down—Ossip started Dayforce, which merged into Ceridian in 2012. From there, Ossip took over as CEO, an unorthodox move considering Dayforce was the one being acquired. But that decision has gone pretty well since then, considering Ceridian undertook the largest tech IPO in Canadian history earlier this year, raising $610 million USD.

All of that success—four sold companies, two IPOs, and a place in Canadian tech history—came down to finding the right opportunity and taking advantage of it quickly.

“It took me a very long time to understand that it’s not about doing the hardest thing or being the brightest company on the block,” Ossip says. “It’s about finding a large homogenous market and a large opportunity. If you solve that elegantly and simply, you can build a company of scale.”

Then, once a company can scale successfully, the most important aspect of maintaining a prosperous business becomes culture. Ossip has spent a lot of time thinking about culture—and no, it does not only involve ping pong and free beer on Fridays.

Find Your Purpose

Culture comes in many shapes and sizes, and each company does it a different way. It’s one of those things that is incredibly hard to do right, while also being incredibly easy to mess up. Ossip is focused on doing real work that employees can be proud of, and that starts with making sure that Ceridian’s work is innovative at its core.

“In 2012 when I looked at Ceridian, it was a culture of survival,” he says. “You can’t build a business on that, so we needed to switch to a culture of innovation.”

Some of Ossip’s foundation of good culture came from Harvard Business School. There, he says, students would be split into sections and trained to work hard everyday. After working, that section would organize fun events and bond together, then get back to work the next day.

“Good culture to me is where people aren’t working 50 to 60 hours a week, but instead when they are working they are completely invested and focused on the outcome of what they do.”

That overall goal might change as both the person and the company progresses, and that again is a sign of what Ossip considers impeccable work culture. Staying in tune with what workers want, not just now, but for the future.

“People transition over time, and as you learn more in a company, you become more familiar with what is out there and you change as well,” says Ossip. “You need to know that what people like today is not what they might like tomorrow, so a good manager will tap into that and learn how they grow and why they want to grow.”

That idea of Ceridian connecting with staff manifests itself in different ways. Take this for example. The company recently put in an unlimited paid time off policy—which sounds great at first, until some Ceridian veterans pointed out that they were banking days off to use for early retirement. Those workers—among some of Ceridian’s most-valued—approached executives and found a plan that worked for them as well as new hires. There were no closed-door meetings or ignored opinions, and no one felt scared to address the problems of what on the surface seemed like an amazing perk.

But perks and open doors are useless without purpose. That’s where the guiding principle for Ossip and his company’s culture comes from.

“How do you bring people together in a way where they actually bond with each other and the company? It’s important because, with that, you have purpose,” he says. “But a bigger part of that is coming up with a purpose for your company, so it has value to your organization. Around that, you have values.”

Determining company values might seem easy if you’ve read a hundred or so About Us pages from various startups, but it’s taken Ossip years to craft his vision.

“As agile people, we are prepared to overcome new challenges,” he says. “That’s part of our culture—that you have to be receptive to change and you need to be nimble in a market. Diligence is again part of that culture. It ties into values like optimism, so when we define optimism it begins with careful preparation, which is diligence. That leads to knowledge, which leads to confidence, and that confidence creates success, and success is reason for optimism. So it all comes back around.”

Best Foot Forward

With Ceridian hot off the heels of Canada’s largest technology IPO in history, that optimism is contagious. Ossip addresses the milestone humbly, saying it simply gives the company freedom in how they want to grow. When someone asked him “What does tomorrow look like?” after the bell rang at the stock exchange and the company netted $610 million, Ossip replied, “I’ll be back at the office.”

That kind of attitude mixed with the success of his current and past endeavours has made Ossip a big name in the Canadian tech world—but don’t tell that to him, as he’ll never see himself as a legend in the scene. Still, he’ll take the time to have coffee or hop on a phone call with anyone who wants to chat, because his experience has given him a unique view of the sector, and one that might butt heads with recent “Canada’s having a moment” headlines.

“The Canadian tech scene, well there’s good and bad,” says Ossip. “We have moved forward, but when I look at other countries, some have moved even quicker. It’s like we’re in a bike lane, but others are in the express lane. There’s a lot to do from the infrastructure perspective to compete with other countries, and I don’t think we’re there.”

Scaling instead of selling is not the industry’s biggest problem according to Ossip—even though some experts in the scene have said the “build to sell” mentality hurts the country’s ability to build an international presence.

“Entrepreneurship is a profession. It’s not a one-pony race,” says Ossip. “I think for young entrepreneurs, building something and exiting then restarting is part of a natural evolution, and not just in Canada.”

“The challenge isn’t with entrepreneurs. The challenge here in Canada is that we don’t have the same access to capital, and the way it moves here and its network is very different compared to the U.S. We have to solve that. The investment community here has a bigger bias on value investments. You can grow, but you can’t grow as quickly as competitors.”

Ossip dubs this the “anti-rich” regime and notes that a lot of his peers have left the country to pursue better access to capital in other parts of the world. His method of fixing it is two-fold: educate investors and entrepreneurs; and build more successful tech companies based on knowledge from those who have experience scaling organizations.

Both of those steps are not easy to initiate, let alone follow-through with. But take advice from Ossip, at least for that second step: scaling a company is all about purpose, which breeds culture which then breeds innovation.

Or don’t listen to Ossip—he’s only scaled four companies, experienced two IPOs, and spearheaded two nine-figure business transactions. Your call.