Diana Dyer, Financial Services Company Founder

FLARE #HowIMadeIt celebrates 100+ talented, ambitious and driven Canadian women with cool jobs. Want what Diana has? Here’s how she did it

Diana Dyer headshot wearing blue shirt

Diana Dyer; Toronto; 


Let’s say we’ve just met at a cocktail party. How would you describe, in a nutshell, what you do?

I help young professionals make educated, informed and bold financial decisions. I am an independent financial advisor and founder of . I am also co-founder of a new fintech (financial technology) company that will help empower young professionals and millennials to take their financial futures into their own hands.

Where did you go to school and what did you study?

I attended the University of Toronto where I specialized in political science.

What was your first paying gig out of school? (In your field, or not.)

Right out of school, I had to take on a few jobs at the same time. During the day, I worked as an account executive at a small financial services company, and worked weekends and evenings in a restaurant.

What was your BIG break? How did you land it?

My big break was actually my first financial services job as an account executive. I had always juggled part time jobs throughout school, but struggled to find easy, accessible resources to help me plan my finances—there was nothing available for young people. This stuck with me for years, so when I learned that a local financial services firm was hiring, I convinced them to take a chance on me. That job taught me everything I needed to know about the financial services industry and inspired me to eventually start my own company.

Describe the moment in which you first realized, I think this is actually going to work out?

When I was 26, I was ranked as one of the top 30 independent financial advisors in Canada. At the time, I was the youngest person to have ever received the award, and it proved I had the experience and tenacity to compete in an industry typically dominated by older men. That’s when I knew it was all going to work.

What would you say has been your biggest failure or shortcoming, career-wise, to date? How did you bounce back?

When I first set up Triumph, I thought I had to project a very serious, conservative image usually associated with the financial services industry. I quickly learned this wasn’t helping me connect with the young professionals I wanted to work with, and wasn’t helping build business. I took some time to rethink my vision and remember what had inspired me to get into the industry in the first place. Since then, I have focused on running a company that truly reflects my personality—whether it’s through our client service or in the way we connect with consumers on social media.

Name one piece of career advice you always give.

No one in life is going to hand you anything worth having. If you see something you want, you have to go get it yourself. Become an expert in your field, make sure you have an amazing mentor (or a few), and surround yourself with people you can constantly learn from. Most importantly, stay focused on your core competencies. Stay true to what you know.

What’s the worst career advice you’ve ever gotten?

There is so much bad advice out there. At the end of the day, anyone who says  you can be successful and NOT give 100 percent to what you are trying to accomplish, almost every day, is giving you bad advice.

Did you deal with barriers in your field because you are a woman? If so, what were they?

Finance is still very much an old boys club, and as a young professional working in the sector, you need a thick skin to survive. I have often felt that, regardless of my performance, my male colleagues underestimate me and my experience. By leading Triumph Capital, I hope to show other young women that it is possible to eliminate traditional stereotypes in industries like finance. We need to raise our voices more, take up space at the head of the boardroom table and proudly flex our skills and know-how, across any industry.

Are you making a fair income for your work? Why or why not? Do you have a side hustle for extra cash? If so, what is it?

I do make a fair income, but it has been hard work to get it! A lot of what I earn now goes back into my second fintech business, a digital platform focused on delivering financial literacy into the hands of young professionals.

What’s the worst stereotype you’ve heard about millennials at work?

We hear a lot about millennials being unfocused, unenthusiastic, and entitled. However, through my own experiences, I have learned that millennials are more entrepreneurial (facing a tough economy, they are evolving to survive and to be able to do what they want/love), ambitious, driven by purpose (they want to do something they care about and that hopefully makes a positive impact on the world), are more engaged with their cities and communities, and are changing the way we do business.

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