The many titles of Anna Sainsbury

Anna Sainsbury wanted to take her kids trick-or-treating. That’s why she arrived in Lisbon a day late.

This anecdote makes me feel I've struck gold: the journalistic equivalent of getting a full-sized chocolate bar on Halloween. I knew about Anna Sainsbury the co-founder, the one who boasted that Vancouver had birthed another unicorn when her company, GeoComply, received significant capital in 2021. She’s also the entrepreneur who won awards for momentum and the individual who has helmed one of Vancouver’s most successful companies for over a decade. I hoped to glean, from the inside of a brightly-decorated cubicle in a conference media room, insights into who she was as a person, as a mom, as a daughter. A trick-or-treating agenda seemed a great place to start.

So, Lisbon-based WebSummit — a preeminent global tech conference — had a scheduling conflict. The event kicked off on November 1, a day famous for not being Halloween. And while that proximity kept Sainsbury off the speakers’ roster on opening night, the unicorn founder had a great alibi for her absence.

In case it were a hidden gem, I cautiously asked Sainsbury where her go-to Halloween neighbourhood happened to be. Steveston, she replied, is the area of choice. (My apologies in advance for potentially blowing up that spot.) It’s a generous one, Sainsbury told me. Sometimes they give out three to four chocolate bars per house. But, the real win is its proximity to the airport. “So, if you’re flying out to Lisbon at 10:00 p.m.? It’s a very good commute,” she says with a laugh.

I first connected with Sainsbury for our How to Get a Job story series, which spotlighted how the GeoComply team works on geolocation compliance, fraud prevention and cybersecurity solutions. Those stories are usually standard fare: a quick interview about culture and workplace practices, a good quote on the company’s vibe, and a few links to learn more. But, on this one, a debate erupted in the VTJ Slack about her title. If you find Sainsbury on LinkedIn, you’ll see a laundry list of roles. She is GeoComply’s CEO, chairman, and co-founder — that middle one causing a bit of editorial stickiness for my team.

Chairman she may be, but Sainsbury is — of course — not a man. So, I opportunistically pounced on the jet-lagged tech leader to unpack what I copy/pasted from her LinkedIn profile. But before I could even stammer out my question, Sainsbury replied by saying, “Well, I am a hu-man.” Jet lag be damned, I guess.

“I don't want to be a girlboss. I'm just a boss,” she explained. “If the title right now is chairman, then it's chairman. It doesn't take anything from me. I just feel like ‘chairperson’ isn't as commonly adopted. And chairwoman feels like…I mean, I just call myself a human. And that's just kind of how I see it.” The bigger problem, she says, is not the title’s gender, but its length. “Usually, people are like, ‘Do we call you chairman and CEO, or co-founder, or do I use them all?’ I once had a business card with all of them on there and I was like, ‘Nobody's going to read all this.’”

That chairman — er…human — grew up on Vancouver’s North Shore. She described her parents' style as relaxed, before adding that her upbringing felt flexible. It allowed her to think critically. Sainsbury details that she would question everything in her teenage years: why did she have to go to school, and why did she have to listen to the teacher? Her parents didn’t question her questions, affording her the freedom of that independent thinking. They did, however, nickname her Bossy Boots when she was younger. I don’t think we’ll be seeing that on a business card anytime soon.

What did stick, though, was that mindset. The approach of Sainsbury the teenager, she said, comes out in the adult entrepreneur. It sometimes appears as cockiness, but a better interpretation would be confidence. Running a company means being convinced it will all be okay, even if the math doesn’t look like it will check out. Especially if you continue to hustle.

For Sainsbury, that ethos was picked up through osmosis in the U.K. She lived overseas for 10 years, which she says gave her a huge amount of exposure to people pushing business to the limit. She described living in London was both motivating and eye-opening. “I feel like that experience helped me a tremendous amount,” she reflected.

At this point in our chat, the conversation drifts back to family. As she listed the places where she has lived and worked, Sainsbury shared that she deliberately settled on Vancouver as an amazing place to raise a family. She thought the city was boring in her 20s. But when you're a parent, your needs change.

The focus on family is a natural one. GeoComply is a family business of sorts: a company Sainsbury co-founded with her husband David Briggs over a decade ago. A need for balance, thus, is built into the company, though it’s something Sainsbury says she’s still trying to get the hang of all these years later.

“It takes discipline to be present, which is something I'm always working on,” she pointed out. “I haven't mastered it. I think wherever you go, if you want to be a stressed-out person, you can always choose that, even if you don't have that much going on in actual fact, right? So, I try to be as disciplined as possible.”

Her children, she says, keep her honest. They are vocal. If she has a serious look on her face, it’s a dead giveaway that GeoComply is taking up some mental real estate, and they’ll call her out on it. Sainsbury’s parents had a business of their own, so she understands the balance intimately. She doesn’t know what it’s like to live any other way, she explained. What’s that saying about apples and trees again?

“I think they're really great at advocating for themselves,” she added of her kids. “That's something that we consciously trained in them. It’s so helpful. If someone can actually say what they need, the chances of them getting it is much higher. It's challenging as a parent or as a boss or as a manager to try and read behind the lines for everybody's secret ways of communicating.”

I’m always deeply curious about whether founders want their children to follow in their entrepreneurial footsteps — if they want them to take a bite out of the apples that they’ve dropped at the foot of their family tree. So, I posed this question to Sainsbury. Do you think entrepreneurship is in their future?

“I think so,” she answered. “They have their passion projects, right? And a lot of it is what the younger generation is frequently talking about now: that's saving the world from the drain we are on the environment around us. Or, saving animals from extinction. My kids are definitely in that camp and I love it. Young people are so motivated to change the status quo. We need that.”

Sainsbury subscribes to a familiar refrain — her hope for her children is simply that they find their passion and run with it. That very well could be achieved by working for themselves or starting a company. But it could also find fruition by joining a non-profit, or another ESG-conscious business. At the moment, though, Sainsbury told me that both her children claim they will sell GeoComply, and then turn their attention to saving endangered shark species.

Where sharks are also endangered, says Sainsbury, is in the boardroom. It’s a trend that she calls “cancel culture for hustle”. The reality, as she sees it, is that it’s not possible to change the world if you don't have grit. To go against the current you have to swim so much harder. That's something that she is trying to push in a healthy way at GeoComply — that employees have to anchor in some grit to get somewhere that's different from where they are today.

It’s easy to just think of Vancouver as an outdoor paradise: a workforce waiting to hit the slopes or the beach. Work-life balance is a tricky, well, balance, according to Sainsbury. “Sometimes I think, in the Vancouver tech market, so much of the conversation is about [that],” she explained. “Your employer is totally responsible for enabling that versus it also being a personal mindset. We really want to continuously get ahead and be competitive.”

It was a timely observation. I, too, had boarded a plane from YVR to Lisbon for one of the biggest conferences in the world. Considering the B.C.-based unicorn surge that Sainsbury was part of in 2021, and the Web3 dominance that earmarked 2022, I arrived in Portugal with my chest puffed out in my blue Vancouver Tech Journal t-shirt. Instead, I was greeted largely by indifference to our town. There were a few outliers, but the most notable Vancouver-based calling card wasn’t Dapper Labs or even GeoComply. Instead, it was the mountains of which Sainsbury grew up in the shadows.

Perhaps her sentiment is due to GeoComply’s decade-long overnight success story, which reached its crescendo in the middle of a worldwide pandemic. On March 23, 2021, strategic investments from firms Blackstone Growth and Atairos afforded GeoComply real estate in B.C.’s unicorn country. But, our world in 2022 looked very different — or, dare I say, unprecedented. So Sainsbury was in a peculiar position.

“To hit that status when you're at home with your kids, teaching them grade two or whatever — you imagined this to feel different,” she admitted. “Here I am wearing my yoga pants, sitting on a Zoom call trying to connect with my growing team. We probably went into COVID with 170 people and now [in November of 2022], we'll probably be at 600 by the end of the year. And you haven't gotten to see all these people.”

She’s still very fortunate, Sainsbury admitted. As the co-founder, she has a lot of equity in the organization. Further, she was relieved that Blackstone was willing to have a conversation with GeoComply and take a minority position in the company. In some ways, though, that feels intimidating, because investors still have certain expectations when they come aboard. That was a hard thing to overcome, she told me. She’s also been travelling more — of course to Lisbon, but also to New York, home of a new GeoCompy office. But it’s been a gradual uptick.

“Ultimately, you just have to be comfortable in your own skin and [admit], ‘I guess this is what it’s like,’” she says. “It's a person that's running around like a chicken with their head cut off trying to make everything work and solve problems. As an entrepreneur, you always feel like you're a startup and you've only just gotten everything a little bit sorted. That's the game I play in my head. I'm like, ‘Why don't I just realize that it's always gonna be quite a lot of work?’ Every time, you’ve got to get to the next level.”

As GeoComply worked to complete the deal with Blackstone, Sainsbury started getting nervous — inspiring her to start hypnosis to get more comfortable. She didn’t have a garage story, Sainsbury joked, so she was concerned about how the media would portray GeoComply’s growth. All of a sudden, the company would be thrust into the spotlight.

“That’s another thing that ties back to Blackstone coming in,” Sainsbury said. “I found it a little bit insulting that we got more media coverage after Blackstone, because that wasn't really what made our technology great. They came in because we were doing something great.

“But, actually,” she continued, seemingly thinking out loud, “hopefully, bringing in investors is what gets you media coverage. But I feel like bringing on investors doesn't solve problems. People that join a company do so for all the other things: ‘What are you about? What are you changing? What do you stand for?’ And, so, anyway, now I'm here.”

Here, at that exact moment, was the media cubicle at WebSummit. At the end of our conversation, Sainsbury asked me what I personally and our Vancouver Tech Journal audience at large thought of the work-life balance and hustle topics we covered. I, like the good fence-sitter I am, punted and said I could see both sides.

Now that I've had time to reflect, I think I’m ready to answer. I’ll admit, I do love how laid-back I hear Vancouver is, compared to London or the U.S. I think it suits my vibe a bit more, but I revisited that opinion often over my days in Lisbon, when people I asked about Vancouver tech returned serve with anecdotes about the city’s extravagant outdoor activity options. Sainsbury, it turned out, gave me lots of chew on. It's as if our interview was one of those chocolate bars they give out in Steveston.

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