What Canada’s top-ranked woman in business thinks young entrepreneurs need to know

Shannon Rogers may be a super achiever of intense focus these days, but there was a time in her life when she was more like the rest of us—somewhat adrift. After completing degrees in common and civil law at McGill University, she landed at a Toronto law firm. “I absolutely knew I was going down the wrong path and I was trying to figure it out. I believe things happen for a reason, so I was very open. I sort of opened to the universe,” she says. Her goal was to jump to an “interesting” company.

A chance mountainside conversation in 2003 led her to the career change that has since defined her life. In that serendipitous meeting in her hometown of Vancouver, Warren Roy, CEO and founder of Global Relay, talked Rogers into joining his tiny five-year-old firm. She became president and general counsel.

Initially Global Relay’s services were a hard sell—“Back in the day, people were like, ‘Why would I want to save my email?’” Rogers recalls—but a string of corporate scandals changed that. Government regulators soon mandated that all digital communication in certain sectors be on file and retrievable, like all other forms of data, as part of beefed up compliance rules. So if a banker writes something like, “Boy, that Timberwolf was one shitty deal," in an email, a company like Global Relay makes it possible for investigators to sniff out the unethical behaviour. Twenty-two of the top 25 global banks now use the company’s software. The firm has 400 employees in six offices around the world and 20,000 clients in 90 countries. This year’s revenue total should be in the $50 million range.

The rise of social media has been good for business. Global Relay’s clients need to keep updating their systems to track the dozens of ways people can send speak to each other online or over a phone network. “We probably archive about 40 different message feeds right now, but every day we get asked about a new one, not to mention all the changes to existing systems,” says Rogers. “We’re always keeping up with both changing regulations and technology fads.”

Fresh concerns about cybersecurity and data protection have been another driver of growth. But the software isn’t only useful for compliance or fraud investigations, Rogers hastens to add. “It’s also just a super handy business tool, because you can go back to last year to find anything in seconds.”

Because of her role as a leader and key strategizer at the wildly successful company, Rogers has become one of Canada’s most respected executives. This year she took the top spot in the PROFIT/Chatelaine w100 ranking for the third time. She has appeared in one of the top three for the past five years.

We reached her during a trip to Washington, D.C., where she was attending the annual FINRA (Financial Industry Regulatory Authority) conference to discuss the world of work and getting ahead as an entrepreneur.

How would you describe your career so far?

Well, it's been a crazy ride and one that would be considered a nontraditional journey, given that my first professional job was at a law firm in Toronto, and now I'm running a global technology company doing ediscovery and compliance worldwide. But it’s been super exciting and the learning curve never ends.

Also, in my heart, I’m an entrepreneur, so I would have to describe it as an entrepreneurial dream, because me and my team created something from nothing. I am at the FINRA conference now—it’s neat, you fast forward all these years and our services are being used by some of the most powerful companies in the world. You can’t ask for more than that.

You left a stable job at a law firm to join Global Relay as employee number four. How does a person decide when it’s time to make a jump like that?

I think you know in your gut when something seems right. You kind of have this a-ha moment, and you think, “I should take this leap of faith.” And when it seems right, nothing stops you.

So I think people do know, whether they acknowledge it or not. It’s hard to do that, to leave a paying job...

Do you think it’s harder in Canada to make that choice, to start something new?

Yes, Canada is actually a much harder country to start a business in, or to be an entrepreneur in, because frankly the market is so much smaller. I often get asked, “At what point should we start looking towards doing business in the U.S.?” And I always say from Day 1. We would not have survived if we had not gone to the U.S. market. The U.S. really is that land of opportunity and they’ll give you a chance, so long as you do a good job, people will support you. It was only after we got it going, got some recognition in the States, and when we were recognized by the Gartner industry analysts of the world as a leader in what we do, that we got some traction in Canada.

I say, when you’re in a software-as-a-service business, the Internet is your world. The global market is your market. I think these days it’s a lot easier, whatever your business is; you can put up your website and you can get known as a global business if you're doing something interesting.

What was the most interesting job you had before this one?

One of them would definitely be my year off in the India. I took a year in my 20s, the year between grad school and law school, and I did a lot of development work, which included about five months working at Mother Teresa’s helping the poor and destitute. You learn a lot doing something like that, about yourself and about the world.

Even in law school, I spent time at different jobs to make enough money to go back to school the next year. Through most of law school I was a cocktail waitress at a bar in Montreal. I started with a paper route, and I was a fish and chips waitress. I also lived in Zambia for about a year and worked at a Safari camp. It was an entrepreneurial venture, too, getting the camp built and set up. I have a huge passion for the outdoors, so it was awesome, living with the animals.

How do you stay sharp? Do you have a morning routine?

Because I'm running a company that is 24-hour business— it’s email, instant messages, it’s online 24 hours—our job never stops. We’re also focused on the financial sector, so by the time I wake up in the morning, it's already afternoon in London, New York is buzzing, and I have 400 emails in my box. Mornings I literally open my eyes and my workday begins.

So I would say the end of day is where I do the calming things. Anytime I have spare time, I want to be outdoors. I live in Vancouver, so we have these gorgeous mountains and there’s lots of hiking. I have a little 21-foot boat that I like to be out on.

That makes me think about the elusive “work-life” balance that has been the focus of so many recent essays. What’s your response to the debate about whether women can have it all?

I have not done a good job with that, in fact sometimes I'm shocked at how women can say that they have a good balance. But I have surrounded myself with a lot of special people I work with, whom I literally consider family and close friends. We’re all really tight. It's the same group we've grown the company with. Obviously the company is now larger, but the same people who started it are still here.

Otherwise, I’m travelling about six year months of the year, so I try to fit in little side trips to keep learning about the city or country I’m in. For instance, I’m in Washington, so I’m surrounded by some of the most incredible American history. I’ll go the museums and to see the monuments.

That’s how I figured out to do it, but “balance” wouldn't be a term I would use, unfortunately.

What would you say women in entrepreneurial businesses should be doing, or doing differently?

Once you start building a company and if you start having some success, you grow an awareness that you're becoming a leader. You realize that there are a lot of people looking up to you for advice and mentorship, especially in a male-dominated field. The majority of our employees are men, although the women at global relay are absolutely fantastic. You suddenly realize you need to be there as the role model for them and help them on their career path.

Also, on the general business front, what I’ve really started to feel is that people have helped us along the way and as we’re becoming a stable company and earning enough that we’re able to, we really do need to give back to our community.

We have a few ways we do that. Our offices are in Gastown in Vancouver and it used to have this famous bike race, the Gastown Grand Prix, but it shut down for financial reasons. Global Relay sponsored it and brought it back. Once we got into that community and met a lot of the top cyclists in Canada, they got us into a charity we built called Global Relay Bridge the Gap, which helps athletes trying to get into the Olympics. It’s for that time when they should focus full-time on their cycling, but they don’t have the money to do it. That led us to sponsoring Cycle Canada.

We also go out to the universities, and open our doors to business students and computer science students to see what it's like to work in the business, ask us questions. And we put a couple of million dollars into a technology innovation hub in Vancouver, for start-ups, for things I wish we had when we were going through it. We never had anyone to talk to, never mind financing.

That would be my advice: I truly feel you have to think of social responsibility—and mindfulness.