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Fearlessness Led Kathy Gregory to the Top of Canadian Fin Tech

Kathy Gregory started Paradigm Quest in 2004, and has been at its helm ever since, growing the small start-up to become one of the leading financial tech and business processing companies in Canada. A natural leader and a passionate advocate for women’s professional advancement, the message Kathy exudes is clear: a woman can do anything when she knows her strengths, and is willing to use them fearlessly.



By Teresa Harris



Kathy Gregory is a woman of face value. There are no pretenses — what you see is what you get.

“Integrity is non-negotiable,” she states. “Nobody ever thinks, ‘Kathy has a hidden agenda,’ because whatever agenda I have, I’m just going to say it.”

Yet while she beams confidence and clarity in who she is and what her vision is today, she acknowledges confidence in yourself is a journey, not a destination.

In the early years of Paradigm Quest, the first business process outsourcing company dedicated to mortgages in Canada, Kathy describes the tension she experienced that many fledgling entrepreneurs face as they balance authenticity with business growth: deciding what deals to pursue, and when to walk away from a bad fit.


“Integrity is non-negotiable.”


Since she founded the company 13 years ago, Paradigm Quest has been selective when it comes to taking on new business, sometimes turning clients away when the organization or its key team members were misaligned with either Paradigm’s strengths or culture.

“It’s hard to say no, but I’ve realized through experience that you can’t be everything to all people,” Kathy explains. “Don’t try to be somebody you’re not, because everybody can see through it. Your best bet is to simply be the best at what you do and leave it at that.”

The strategy has worked. Paradigm is now a multi-million dollar company that employs over 300 people, positioned as the domain experts in the mortgage marketplace. As an end-to-end or à la carte solution, Paradigm Quest is focused on bringing the right technology and the right people to organizations who want to service residential mortgages and loans across Canada. “We’re no longer the little engine that could,” Kathy says, with apparent pride in her company, team, and herself. “I’d like to leave that legacy — I want people to say, ‘Wow, she lead a team and built something amazing and disruptive, in a predominantly male-dominated industry.’”

Kathy recognizes that the financial industry continues to deal with repeated instances of gender inequality. Yet, she admits to having never felt it first-hand during her career ascension. “I never went into a room and thought or noticed, ‘I’m the only female.’” In fact, the stark reality of just how outnumbered women are in the financial world didn’t set in until she became a business owner herself.

“People would say to me, ‘We finally have a female CEO in this industry,’” she remembers. “When I finally noticed, it made me realize what an injustice I’d been doing to myself and others by not paying attention.”


“When I finally noticed, it made me realize what an injustice I’d been doing to myself and others by not paying attention.”


And she feels the injustice goes beyond recognizing the opportunities she missed to help course-correct gender inequity. “The people you’re trying to please — your clients — are diverse. It’s good business sense to then have a team that mirrors that.” Which is why Paradigm’s executive leadership team is made up of over 50% women, a definitive practice Kathy began early on — and continues to stand behind.

“There’s a gender inequality issue in this country that shouldn’t be ignored,” she states. “And yet, when you’re starting out, you shouldn’t be thinking about that every day. You shouldn’t be giving others the chance to think about it either — you should be honing your skills and becoming the best at the job.”

As the owner and chief decision maker of a company that manages $26 billion dollars in its portfolio, Kathy is not only a vocal advocate for women’s C-suite advancement, she is also generous in admitting that by valuing skill above ego and all else, she has managed to surround herself with the best brains in the business.

“I have five or 6 people, men and women, whom I go to in the organization every time a problem or crisis comes up. They all bring such different perspectives, and together the problem gets solved.” By structuring her business in such a way that allows for change to occur and for Paradigm leaders to involve people right across the organization to be engaged — enabling nimble problem solving in response — Kathy actually looks forward to unexpected shifts, and encourages others to as well.

It’s one of the key messages she offers to the many up-and-coming women she mentors, along with ensuring that fear takes a back seat. That said, she hesitates to diminish the value in healthy fear: “You should be afraid of what can go wrong,” she advises. “There’s advantages to being cautious and reproachful, but in a lot of cases it just limits our ability as women to become what and who we want to become.”

So how does she recommend women overcome their hesitation?

“Ask yourself: ‘If I try this, and I fail, is anyone going to die?’” And if the answer is no — jump.



Success is difficult to achieve on one’s own; it takes a village. The secret is surrounding ourselves with excellent people who aren’t afraid to defy convention and who get excited about bold innovations and creative problem solving. At Paradigm, our four major principles have stood the test of time and the uncertainty of change. We consistently put the Paradigm Team first. We are performance driven. We over deliver on service excellence. We constantly challenge conventional thinking. To make an indelible mark, we live these principles. We think differently and act disruptively.