Entrepreneur Of The Year 2021 winner: Judi Hess turbocharged Copperleaf by reinventing its company culture

By focusing on exceptional customer and employee experiences, Hess has built the decision analytics software firm into a global player with clients in 24 countries

When Judi Hess joined Copperleaf Technologies as CEO in 2009, the Vancouver-based decision analytics software firm looked very different than it does now. “I always say it was both the worst and best decision of my life,” Hess recalls with a laugh.

Despite doing her due diligence before taking the job, Hess, who was leaving a role as managing director of Canadian operations for U.S. photography giant Eastman Kodak Co., didn’t fully understand what she was walking into. “When I started, we didn’t have a product that was ready at all. We didn’t have any money to finance the company, and so many challenges to start with. But it was exciting because it was a very small company, and I thought it would be a real challenge.”

Copperleaf was posting some $1 million in annual revenue, and Hess decided that the first thing that needed attention was the company culture. So she gathered all 45 Copperleaf employees and started working on building a more collaborative approach. “We talked about what’s important to make sure that we’ll be successful and we’ll enjoy the journey,” Hess says. “Had meetings and discussions, all-day breakout groups. It took a number of iterations, but after about eight months, we came to the culture we have today.”

To this day, Hess personally spends three hours with each new hire to discuss the culture and how important it is to the company. She describes that culture as delivering exceptional value to clients and providing extraordinary experiences to both customers and fellow employees.

“Knowledge isn’t power, it’s for sharing; that’s how teamwork works,” she says. “We want people to speak up, even if it’s controversial—want people to put the elephant on the table, talk about it, make sure we’re addressing everything.”

Hess has also long been a champion of diversity, something spurred by her own experience navigating the challenging road of being a woman in a tech industry still dominated by men. With some 350 employees and with clients in 24 countries, “we need proper representation, and we’re very committed and focused to making sure we make adjustments to ensure a diverse group,” she says.

To that end, 50 percent of Copperleaf’s board and 45 percent of its leadership team is from underrepresented groups. Hess recently brought in Indigenous and neurodiverse speakers to ensure that staff are educated on related issues. She also put together a Black Lives Matter panel last year.

“It’s really just to give our company an idea of how these things manifest themselves,” Hess says. “And make sure they understand that it’s not just some random events; this is a systemic problem we all need to face.”

The culture that Hess has worked so hard to build was originally threatened by the COVID-19 pandemic. But though Copperleaf slowed its hiring process initially—the firm only brought on what Hess calls critical hires—there were no layoffs.

“When it started, like everyone, I had no idea how it would affect us,” she says. But Hess quickly realized that, at the very least, the business would be able to survive, given that Copperleaf supplies its product to companies that manage critical infrastructure, like the B.C. government and various provinces’ hydroelectric operations.

“They weren’t going to disappear,” she explains. “The biggest impact was that there were some deals that got delayed, and clients didn’t have all of the staff to do the work that they had to get done. But we didn’t suffer as much as I expected we would.”

Copperleaf’s sales more than doubled from 2019 to 2020. Hess isn’t complaining, but she’s still “absolutely convinced” that the company would have done better without the pandemic. That mindset is simply part of her take on culture and her emphasis on always striving for improvement, both individually and as part of an organization.

“With more than 350 people, if every day at the end of the day they all say, What could I do better tomorrow, then how can we not succeed?” she asks. “There are more things that go into it, but we try to be the leader in our market, the best partner to clients and to enjoy the journey.”

10 Questions With Judi Hess

What was your first summer job?

Retail sales clerk in a shoe store.

Is an entrepreneur born or made? 


What is your definition of success?

Creating value and happiness together.

What other career might you have had?


Name one thing that people would be surprised to learn about you.

At university, I asked if I could do a double major in mathematics and theatre arts, but they didn’t offer such a program!

Finish this sentence for us: “Entrepreneurs need a lot more…”


What businessperson do you most admire?

Bill Gates.

What do you do to relax/unwind?

Skiing, biking and yoga.

How would you describe your leadership style?

Collaborative and determined.

Name an item you typically forget to pack on business trips and regret not bringing.

Power cords for the myriad of devices I carry with me.