In the Spotlight: A conversation with Jenna Kaye

Jenna Kaye has journeyed from a promising career in securities law to the forefront of entrepreneurship, founding multiple companies in finance, crypto, and social impact. As founder and CEO of the disruptive financial institution Odyssey Trust, she is redefining what’s possible in a highly traditional industry. In a recent conversation with BLG’s Calgary Regional Managing Partner, Melinda Park, Jenna shared insights into the values that fuel her drive, her vision for a more inclusive business world, and the power of mentorship in building a career of impact.

The entrepreneurial leap: Resilience, perseverance and a lean mindset

Melinda Park (MP): You’ve made a significant transition from a successful law career to founding a disruptive financial institution. What personal values or experiences gave you the courage to take that leap?

Jenna Kaye (JK): A big part of being an entrepreneur comes down to two skills I find essential: resilience and perseverance. I developed these playing high-level sports long before I became a lawyer. You learn quickly as an athlete that to be at the top, you have to be resilient when you face problems. It’s the same in business. We face new challenges every day, and resilience helps you start from a place of, “Okay, I know we can get past this.”

Perseverance is the other side of that coin. In sports, you’re down 10 points with two minutes left, and you have to figure out a way back into the game. It’s no different in business. You have to learn how to persevere through challenging times. When we first started, people said, “Why are you starting a transfer agent? The IPO market’s dead.” Two years later, that market had a massive boom, and we handled most of the IPOs because they were in emerging industries. You’ve got to get yourself to first base to get to second. You have to take the risk.

That perseverance has been essential as we’ve grown. We expanded into the U.S. a few years ago, and it’s been a whole new challenge, but also really fun to learn. That part of the business has scaled significantly, and I now spend time almost every week in the U.S. driving our growth there.

I’ve also been lucky to be surrounded by people who’ve said, “Why not you?” I think women, in particular, need to be stronger at taking that shot, even when you think you’re only 80% of the way there. Once you’re in the game, everything changes.

MP: In those early days, you were wearing every hat in the company, from finding investors to obtaining regulatory approval. What daily habits or frameworks helped you stay disciplined?

JK: One thing that has served us really well is that we have been lean since the outset, and we’re still lean today. When I used to travel to Vancouver to open our office there, I stayed at a hostel because we were so budget-conscious. We wanted to show we could be profitable. While other tech companies were focused on expenses and pouring capital into the business, we were always asking, “How do we protect capital? How do we show we’re making money?” That mindset is integral to Odyssey.

Plus, I’ve always held onto that mental framework of, “Why not me? Why not us?” When we were becoming a federally regulated institution, people said we had no business doing it: we were small, from Alberta, and female-led. The regulators themselves noted they’d never had a female applicant for a federal financial institution before. That just made me want to do it more.

Driving change for women in business

MP: Through your work with organizations like Axis Connects, you are actively working to increase diversity in leadership. What progress have you seen, and where do we still need to see change?

JK: Axis has been incredible. The community of women who feel passionate about this has grown exponentially, and it’s been amazing to see men just as equally jump right in and want to be a part of it. The female representation on boards in Alberta has jumped from 12 per cent to 27 per cent since we started. It’s not to say we’re the only reason, but we certainly have something to do with it. The conversation is just more easily had now.

As for what needs to change, I think as a country, we need a much stronger daycare and parental leave support system. Ten-dollar-a-day daycare is amazing, but we don’t treat daycare providers the same way we do kindergarten teachers, and I don’t understand the logic behind that. In Alberta specifically, one of the things that really hurts us is that kindergarten is only two and a half hours a day. What are you supposed to do in any career?

There’s also a lot we could do on fertility. Women in demanding careers, particularly in legal practice, are often having children later. I was pretty open about doing IVF with all my daughters, and it should be free. Your workplace and your government should want you to have the financial resources to do that.

The power of mentorship and leading by example

MP: Who from your time at BLG had the most meaningful impact on you?

JK: It would definitely be Jon Doll. I never had a great mentor until Jon mentored me when I was an associate. He took me under his wing, and it was an invaluable learning experience. It’s a great example of how strong the influence of having men championing women’s careers can be. He continues to be involved with my business today as the corporate secretary for Odyssey. He just gets the end goal and helps us find a way there.

MP: How has that experience shaped your own mentorship style?

JK: The best way to lead people is to be honest with them about what they’re trying to achieve and how you can support it. You also need to let people sink or swim sometimes and show you what they can do. And finally, you need to encourage the behaviors you want to see. One of our core values at Odyssey is GSD, or Getting Stuff Done. We value people taking initiative, and we tell them, “Ask for mentorship, ask for support, and don’t be afraid to put your hand up.”

MP: When have you felt the proudest in your career?

JK: I’m inherently not someone who takes a lot of time to feel proud about things, which is the downfall of most women. But the times I do feel really proud are when I see my team coming together and see how happy everyone is to be at Odyssey. I think about my daughters going to work in an environment like this and how supported they would be.

Sometimes I’ll secretly overhear someone talking about Odyssey, and it’s the best feeling. To hear a 24-year-old on our shareholder services team say, “I used to be intimidated at work, and I came to Odyssey and I just love my boss and the opportunities we get here. I can’t even believe this place exists.” When I hear that, I think, “That’s it. This is all I was meant to do.”