The Shifting Tides of Growth and Tech’s New Workforce

How leadership from growing companies like Bench, Shopify, and OMERS Ventures acclimate to an evolving style of work.

The concept of work has evolved through the application of technology, the distribution of wealth, and the shifting tides of a younger-than-ever labour pool. By 2020, close to 50 per cent of the workforce will be made up of millennials whose style of work already boasts a number of nicknames: the “Uber” generation; side-hustlers; the five-to-niners. These nicknames denote a group disenchanted with normal routine—whether it be more financial freedom, richer experiences, or personal growth, they’re hungry and looking for something new.

millennial working laptop

That mentality is leading to a redefinition of the term “career longevity,” with the notion of spending a lifetime at one job falling by the wayside. Hiring managers are left to sift through the rubble of the corporate ladder, struggling to find what it takes to inspire long-term success in their provisional teams. The road ends with companies spending small fortunes on employee perks, all to watch team members walk out the door after two years.

Talking ‘Bout My Generation

Job security was a loaded topic in the past. Now that promise is disappearing beneath the depths of unpaid invoices and the guaranteed pension offered to baby boomers’ after a decades-long career.

There’s a silver lining. As a generation that is often forced to write their own job descriptions, young professionals now hold roles that aggregate skills from several disciplines. The current working climate values short hops around different posts with the incentive of learning as much as possible. A deep resume will better prepare prospective job-seekers for that hybrid engineering/sales and marketing/accounting stint down the line.

Ian Crosby is the co-founder and CEO of Bench, a fast-growing bookkeeping company based in Vancouver. As the head of a company that’s currently hiring for over 100 roles, Crosby understands what the working climate has become, and what it evolved from.

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Bench’s Vancouver office. Photo by Techvibes.

“I’ll call it the old guard attitude: your job was to climb the ladder, pay your dues, and go through noble suffering, and eventually you’ll end up in a place that rewards you for your years of sacrifice,” Crosby explains.

“It’s like people are in a Machiavellian struggle to knock each other off the ladder to climb farther,” says Crosby.

“It’s as if you have to suffer through the first ten years of your career because that’s just what happens,” he says.

That “old-guard attitude” Crosby is referring to still exists, but it has become increasingly transient. It’s on the way out because many companies still refuse to invest in their employees, a term that has come to be known as re-recruiting. This can be achieved through specialized workshops, teaching opportunities, educational perks and any other kind of resource provided by a company to their employees to stimulate learning.

The new-guard is marching in, especially for employers who value culture—and that means the tech world. Continuous growth is treasured so long as an employee is building new skills and working towards a common goal with their colleagues. Oddly enough, this ideology works both ways. On the business side, companies of all sizes can embrace lifelong learning; on the employee side, the promise of growth can guide someone’s decision to either stay in a role for 10-plus years or swap between companies in search of new inspiration.

Sit Down, Stay a While

The push for continuous learning is nuanced: managers identify the goal a team is working towards and allocate resources to reach that goal. They must also convey the impact reaching the goal has on their community or clients.

Jean-Michel Lemieux understands the harmony. As the SVP of engineering at Shopify, one of Canada’s most successful technology companies, he (and Shopify itself) are strong proponents of lifelong learning.

“Everyone at Shopify believes in and understands the problem we’re solving,” says Lemieux. “It sounds simple, but I feel a lot of companies…don’t. We work to share internally how the software we’re building impacts entrepreneurs and the planet.”

Shopify hires both new graduates and tenured professionals. They invest in re-recruiting through company-wide conferences and employee-led workshops, among other initiatives. This runs deeper than simple office perks and exemplifies a trend that several companies beyond Shopify are realizing.

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Shopify Montreal. Photos by Techvibes.

Lemieux is an expert in software engineering and it’s his goal to pass that motivation on. He also realizes his job description changes every six months, so learning is not only a passion—it’s a necessity.

“Some of the recruiting work we’re doing is learning how young the software engineering world really is. After you’re hired, that’s the start of your journey to get better as an engineer,” says Lemieux. “Most companies spend so much on recruiting and zero money on growth. Re-recruiting for us is a strong two-sided commitment—we want people to come in and want to grow, and we pay that back by giving them room to grow.”

Lemieux’s LinkedIn profile reads “Recruiters: I’ll spend the rest of my career at Shopify. Please no job reach-outs.” It’s safe to say that he is onboard with one company and solving all the problems that come their way for the rest of his life. With this kind of mentality, his reaction to high turnover—especially in the tech world—comes as no surprise.

“As an industry, I would like people to think about being able to grow in a company and not have to get promotions or swap companies to learn new skills,” he says. “It’s a good thing to stay at a company. I think the churn rate in Silicon Valley is unsustainable and it’s giving the wrong message around committing to your craft and creating excellence.”

“Companies have failed at actually saying that they care if their employees stay,” says Lemieux.

“I would like to see tech rebalance and recognize commitment to a company’s mission and growth, and making sure their employees actually have those opportunities to grow.”

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Shopify Waterloo. Photo by Techvibes

Giving their employees opportunities to grow is Shopify’s guiding light through a shifting workforce. The Ottawa company has a plan for what the future will bring because as Lemieux says, they “won’t solve commerce’s problems in two years.” The lack of this kind of planning is one of the fundamental flaws with new startups and scaleups, at least in Lemieux’s mind.

“I want to throw a challenge out there,” he says. “I’d love for every CEO to talk to their teams. Maybe not about lifetime goals, but talk about a decade. The people on your team will make good decisions if they know there’s a two-way commitment happening.”

Follow Your Dream(s)

No one denies that learning new skills is important. Three-fifths of people think only a select population will have “stable, long-term employment” in the future, so it’s important to gain experience. What matters is if that principle applies to the entirety of the working world. Jumping from role to role and company to company, learning something new then starting a business and selling it before starting another one—there is nothing inherently wrong with that.

John Ruffolo is the CEO of OMERS Ventures, the venture arm of one of Canada’s largest pension funds. His job is to meet entrepreneurs and gauge if an investment is a right move. So far, Ruffolo and OMERS Ventures has chosen well—they invested in Canadian tech mainstays like Shopify, TouchBistro, Wattpad and Hootsuite. Through this experience with both new and established companies, Ruffolo has seen that new-guard attitude come into play.

“A number of people start to self-select, and you’re seeing that now. I think people don’t view staying for a lifetime at companies as a goal,” says Ruffolo. “A lot of people—and this wasn’t the case 20 or 30 years ago—will say I’ve had a great run, now it’s time to go to another organization to test my abilities.”

“I can’t recall if I have ever had a conversation with anyone in a startup who said ‘this is what I want to do: work for this one company for the rest of my life,’” says Ruffolo.

“It’s not because they’ve had bad experiences. This generation just really values multiple experiences.”

Ruffolo began to notice this trend about five years ago with OneEleven. Opened in 2013 by OMERS Ventures, OneEleven offers services and office space to small technology companies so they can scale and grow without having to sign long-term leases. It was this sense of community, with professionals working towards different goals, that jumped out to Ruffolo.


There a buzzy name for it: cross-pollination. Crosby turned heads in the tech world when last year when he called for more cross-pollination—that is to say, experts lending a hand at one company then heading to another, spreading their talent all around. When he said that, he didn’t even think about the possibility of anyone disagreeing with him.

“It’s so fundamental to the tech industry,” says Crosby. “We’re constantly helping each other out and sharing expertise between companies. That’s the only way any of us will be successful. There’s almost an expectation that’s going to happen.”

Crosby used the tactic to help boost Bench. He hired Geordie Henderson from Hootsuite to be Bench’s new SVP of engineering, along with a number of the company’s engineers. In a year, Henderson helped Bench become almost twice as effective per dollar spent on product and engineering.

Keeping (Start)Up With The Joneses

Bench is a large company with its own headquarters, and cross-pollination helped them reach new highs. But for startups, this tactic can be applied in another fashion: coworking. Companies like WeWork have built massive businesses off cross-pollination, purporting that having flexible office space is great and sharing a building with dozens of other companies and experts is even greater.

This model has led to huge companies moving into coworking spaces to take advantage of the atmosphere. Many WeWork locations act as innovation centres for all kinds of entities—for example, banking giant RBC rents out an entire floor of one WeWork Toronto location, despite the fact that their Royal Bank Plaza (and its 65-plus floors) are just down the street. Hubs like the MaRS Discovery District invite massive companies like CIBC, Facebook and Samsung to take up space in their buildings—all fueled by the idea of cross-pollination.

The MaRS Discovery District, home to hundreds of companies. Photo by Techvibes.

“Now all of a sudden, the large mainstream companies are going into [coworking] spaces, because that’s how they are operating,” says Ruffolo. “Having physical places where people can cross-pollinate like that is becoming more apparent.”

From an investment perspective, cross-pollination is often a huge boon.

“We see it in our portfolio all the time: people who say they’re really good at starting up a company, but when it comes to scaling up, it’s not their strength,” says Ruffolo. “So they leave, come to us and say they want to go another startup in the OMERS portfolio. We’re starting to move our employees across different portfolios depending on where their expertise is.”

Imagine an Ocean’s 11-style team of specialized experts, moving from startup to startup: one person is an amazing CFO; another knows VCs in the Valley; the other knows how to source a top-notch engineering team. They’re the C-level ringers.


Okay, maybe it’s not quite like that, but the overall idea remains the same. People want to help grow several businesses and learn new things along the way. They are not content with sitting behind one desk and staying put for 30 years.

“The successful companies and people are the ones that have the self-awareness to say they may be fantastic at starting up but aren’t the next person, so they help find the next person to take the company to the next level,” says Ruffolo. “It’s hard to do.”

“I call it founderitis. The company is getting successful, and that founder has to evolve, and a lot of them can’t make this transition to something else,” says Ruffolo.

As much good as cross-pollination can bring, it also has its downsides. There are obvious examples of when outside talent has to be brought in, say when a founder without engineering experience needs to build out an entire engineering team. They can learn how to do it themselves over the course of a year, or simply bring in an expert. The risk comes from selecting the right candidate.

“When that person coming along, they aren’t only coming with skills, they’re coming with a culture and attitude,” says Crosby. “If you’re cross-pollinating, make sure you’re doing it with the characteristics you want to spread. It’s possible to bring in some really unintentionally counterproductive ideas and philosophies that make people miserable.”

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Bench in Vancouver. Photo by Techvibes.

That mistake happens often and is one every startup veteran is aware of. Crosby made the right choice when he brought in Henderson from Hootsuite to build out his engineering team, but not everyone has the same story. Ruffolo has seen the good and the bad time and time again through the companies he interacts with.

“Here is the honest challenge,” Ruffolo explains. “When you’re scaling up and you realize you’re on a successful path, the reality is there are folks in the company who have the ability to continue growing, but there’s a number of folks in there who really don’t. And that’s when you start to have to replace or bring in folks above them who have been there and done that to really train them. That creates a lot of stress in the organization.”

The true indicator of success is when a company can make that transition and stay aware when something runs askew. It might not be immediately apparent but the team and skills that bring a startup from no profit to $10 million will not be the same set that brings it to $100 million and beyond.

Whether the company is Google or the dog-walking startup down the block, the focus should always remain on growth. As an employee, a founder, or an investor, the steps someone took to achieve a current position will not be the same ones they need to evolve and make the most out of their life. Whether that means learning from within a company, absorbing new skills from outside sources, or hopping into a completely different role, growth reigns supreme.

But will the culture of work ever return to a place where the most enviable position is one where someone can plant their feet and stay for a lifetime? Use wellbeing as the model.

“You should enjoy your life now,” says Crosby. “Have health and happiness now. It’s not a thing you put off then eventually get after you deem it worthy. Progressing is a part of the nature of learning. Make your life work now because developing your career is part of a joyful lifelong journey.”