Fintech CEO Dianne Cupples: “It’s All About What You Do for Other People”
“Whether it’s in the role of leadership, or a business helping a customer to be successful, it’s all about what we do for other people.”
Dianne Cupples is the CEO of fintech company Portfolio+, acquired by Vencora in 2019, an operating group of Constellation Software Inc. Portfolio+ provides software and services through their open core banking solution to support Canadian financial institutions such as banks, trust companies, credit unions, alternative lenders, and BaaS providers. Dianne has been a TEC Canada member since 2020.
Dianne’s ethos is one of service. She doesn’t need, or even particularly like the spotlight; although, she certainly deserves it.
Fintech CEO Dianne Cupples: “It’s All About What You Do for Other People”
“Whether it’s in the role of leadership, or a business helping a customer to be successful, it’s all about what we do for other people.”
Dianne Cupples is the CEO of fintech company Portfolio+, acquired by Vencora in 2019, an operating group of Constellation Software Inc. Portfolio+ provides software and services through their open core banking solution to support Canadian financial institutions such as banks, trust companies, credit unions, alternative lenders, and BaaS providers. Dianne has been a TEC Canada member since 2020.
Dianne’s ethos is one of service. She doesn’t need, or even particularly like the spotlight; although, she certainly deserves it.
Humble Beginnings
Dianne began her career working in her local credit union in a small community north of Toronto. Starting as a teller, she got to serve the people she knew and saw on a regular basis. This provided her with hands-on banking experience, exposed her to a variety of financial products, and allowed her to see the difference they could make in people’s lives. Her dedication to people and ambition to see them succeed led her to hold various roles within the credit union culminating with the Branch Manager position before departing on her next endeavour.
After a brief stint as a financial consultant, she joined Portfolio+ in the early 2000s as a Financial Application Specialist. Again, starting in this role supporting customers, she developed a strong knowledge of the technology side of banking, which complimented her previous work experience with the processes and products in the financial marketplace. The Portfolio+ product and service offering supports financial institutions, which in turn supports the financial health of Canadians.
Next Steps: Portfolio+ and Women in Leadership
Working her way toward her current position as CEO, oftentimes when networking in the industry, she would find herself as one of the few women in the room. She recalls that she had to be comfortable in her own skin, putting herself out there, and being respected for what she brought to the table. Her composed and modest demeanour shines through when she states, “I don’t view that as a challenge, it was just a learning experience.” What brings her joy now is seeing more women working in fintech and in the financial services industry. You can see this in the team at Portfolio+ where 45% of the leadership team and 50% of the organization as a whole identify as women.
When asked what advice Dianne would give to women who are currently entering or moving up in their companies, she says, “don’t be afraid to ask clarifying questions, because sometimes a statement may not be intended the way you hear it.” Secondly, “I think everyone should find a coach or a mentor, someone that is in their corner, that they can bounce ideas off.”
“It shouldn’t matter how you identify. The question should be, can you lead? To lead you’re putting other people ahead of yourself because it’s not about you; it’s about them. It’s about what you leave behind.”
Finding TEC
During the COVID-19 pandemic, Portfolio+ and Dianne were going through several changes and challenges. Aside from going from working in the office to being 100% remote, Dianne had also recently started her new position leading, and Portfolio+ was transitioning from founder-led to being part of a public company. She was approached on LinkedIn about a TEC CEO Group which had an opening, so she decided to give it a try.
What she realized was that she was feeling isolated as a recently promoted leader because she couldn’t bounce ideas off the people she used to; the people who used to be her peers were now her direct reports. She recalls the adage that it does feel lonely at the top.
One of the greatest impacts TEC has had on her business came when her Chair, Brian Brennan, used his network to connect her to a resource to support her in the communication of the business’s strategic vision. His connection helped her develop an approach to communicate her vision to the Portfolio+ team in a way that resonated.
“Using storytelling, I paint a picture of the future I envision but do not tell them how to achieve it. The team then has the opportunity to roll up their sleeves and get creative to make it happen. I would never have thought of it in that way, and it’s been a key piece of our strategy sessions and messaging through the organization.”
Throughout the years of being a part of this TEC CEO group, the other members have offered many nuggets of information and concepts that she has taken back to her role and her leadership style.
“I started with TEC because of the pandemic. But I’ve stayed because of that one day a month, plus the meetings with Brian, to keep myself thinking outside of the business. Leaders spend a lot of time in the business, and we must force ourselves to look beyond.”
The Future with TEC
True to her character, Dianne credits Portfolio+’s success to her team and to the people she feels privileged enough to serve.
“The thing you realize is that the biggest asset we have is each other, and what we can do together, that is where the magic happens. Our IP is an asset, don’t get me wrong, but that IP wouldn’t exist without our founders, the people who have built it, and the people that continue to maintain and evolve it. In the end, everything comes back to people.”
Dianne and Portfolio+ are proud to continue to serve Canadians through their customers and partners by solutioning products which help them grow their wealth, as they have done for the past 35 years. This includes items such as their reverse mortgage product and their mission to leverage technology trends in alignment with changing regulations as they continue to come forward.
For more information on Dianne Cupples’ work and the products Portfolio+ offers, visit the Portfolio+ website. If you’d like to discover your eligibility for a TEC Canada group, fill out the form below and we’ll be in touch!
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