Kelly Emery co-founded and sold Ratesupermarket.ca, then started Troop

Kelly Emery has entrepreneurship in her DNA, being the third generation in her family to start a business, and, like many next-gens now, her forte is in the digital realm, compared to the manual work her father’s and grandfather’s businesses entailed.

Her latest startup, Troop, is a tech platform that helps companies with their corporate donations to local charities, allowing employees and even customers to choose where donations go. Companies receive a curated list of vetted needs in the community and pick the one that resonates with them most.

Emery had previously co-founded and exited Ratesupermarket.ca, a rate comparison site for personal finance services, now rebranded to Ratesdotca with majority shareholder Ontario Teachers’ Pension Plan Board.

Here she shares how her parents and mentors taught her not only how to be a great businessperson, but also how to find strength in being a woman, rather than the female version of a male leader.

You are a third-generation entrepreneur. How did your grandfather start out?

“My grandfather, Peter Emery was an electrician. In the early 1960’s he started a heating and air conditioning company in Midland, Ont. My dad, Robert Emery, was the youngest of nine children. Along with his four brothers he would spend evenings after school and summers helping his father wire houses and cottages along Georgian Bay and install heaters and air conditioning units.

In 1971, at the age of 19, my father decided to pursue his own license in HVAC and headed to Chicago for the nine-month trade program.

After graduating, he left the family business and got a job with a larger heating and AC company in Waterloo, Ont. In 1976 he married my mom, Jane Charlebois, and together they worked towards building their savings so Dad could set out on his own.

In 1982, with three children at home and an economy reeling with 18-per-cent interest rates, Dad and his business partner, Bill Cronin, took the leap and went out on their own, starting Cronin Emery Mechanical with $20,000 in savings between the two of them.

They started in a basement, moved to a barn and then into an office of their own.

Over the next 20 years, they built a solid business with 45 employees, known for its knowledgeable and respectful sales team, fast and professional installation team, and amazing customer service.

In 1999, Cronin-Emery was one of the top dealerships in Ontario and was acquired by [Texas-based] Lennox International as they expanded vertically into regional markets.”

How did your dad’s experience shape your own work ethic?

“I saw my dad working hard every day of his life – up at 5 a.m., home at 7 p.m., and repeat.

This definitely influenced my work ethic, but Dad also showed me that business isn’t just about working hard, it’s also about building the type of company that people want to work for.

My dad and his partner built more than a group of employees. They didn’t just care about their team’s work, they cared about their lives. They supported their team through divorce, alcoholism, homelessness, illness and even the death of a team member. They built a community and a business that operated like a family.

After five years of working at Cronin-Emery, an employee would receive a gold ring engraved with the C-E logo – the family crest. For every five years of service after that, a diamond would be added to one corner of the ring. This ring was worn as a symbol of pride for what the business stood for: community, professionalism, and respect for others.

When I first started on my entrepreneurial journey in 2008, it was almost a decade after Dad sold his business. That Christmas, my dad had his own ring changed into a necklace and gave it to me as a gift. It was his way of saying, ‘Don’t just build a company, build a community, build a family.’

Dad showed me that employees are the most important part of building a business. And the necklace reminds me of that every day.”

What was it like growing up in a family business environment?

“Dad’s work took center stage, but he always tried to involve us and he used his business as an opportunity to give us ‘real-world experience.’

My older sister and I did the office cleaning and secretarial work, my brother was out on a truck by the age of 14, and my younger sisters took over grass cutting and lawn maintenance for the office building.

I remember the Christmas parties, the curling bonspiels, the baseball tournaments, the fishing weekends, the pool parties and many other family gatherings with the entire Cronin-Emery team, and their families, throughout the years. The business was completely intertwined into everyday life.”

When did you feel your own entrepreneurial interests start to take shape, and how did your family support you in your earlier years?

“Just as my father was influenced by watching his father build a business, so, too, was I.
I always knew I wanted to start my own business. I wanted to build a company just like Dad, but I didn’t have a business idea.

I went to business school at Wilfrid Laurier University and thought I’d figure it out there.

After graduating, I wanted to travel and take some time to explore the world. My parents were incredibly supportive of this idea. They just wanted me to look for a job that would help me start to discover the bigger problem I would work towards solving.

At all points in my career, my parents never pushed me in any one direction. They encouraged me to explore and find my own path and enthusiastically supported each stage along that journey.

I moved to London, England, in 2003 and spent 6 years traveling across Europe and working at a private bank. It wasn’t until my partner and I started discussing our move back to Canada that the timing to start a business became more clear.

Together, we co-founded RateSupermarket.ca in 2008, the first personal finance marketplace in Canada, after seeing the success of a similar business in the U.K. Over the next five years, we grew the business and our family of employees to a team of 30 people.

In 2013, RateSupermarket.ca was acquired by our competitor, Kanetix Ltd.

I stayed on at Kanetix and started a new division for the company, a digital consulting practice. I was a member of the exec team when Kanetix was acquired by Ontario Teachers’ Pension Plan in 2018 and is now rebranded to Ratesdotca.

Then, I had the opportunity to explore further, to discover where my passions would take me next. That led me straight to the topic of TechForGood – [a movement aimed at] how we leverage technology to solve more important and meaningful problems in the world.

After a year of research I started my next venture, Troop, a tech solution to unleash generosity in communities and help businesses engage employees in local giving initiatives.

It’s hard to miss the connection between what I witnessed my father building as a child and what I now hold dearly as a core value: community. It is this value that I help other small- to mid-sized business owners share with their employees and customers.”

How did the educational choices you made affect your business trajectory?

“I chose Wilfrid Laurier University because their co-op program was one of the best in Canada and I wanted to get real-world experience as quickly as possible. I also wanted international experience and they offered academic exchanges and even international co-op placements.

In university, I took advantage of all the opportunities and did an academic exchange in Budapest, Hungary, and two co-op placements in Auckland, New Zealand.

In New Zealand I met my partner, Kelvin Mangaroo, also a business grad with a love for entrepreneurship. After graduating in 2003, Kelvin and I headed to London, England, where we could get jobs and continue our love for traveling.”

What supports did you find valuable in building your businesses?

“In growing my business now and any business in the past, I have leaned on monitors, advisors, accelerators, and more recently other female founders who can relate to the unique challenges faced when building a business as an underrepresented founder.

A founder’s journey is filled with hard questions, tough choices, lots of bumps, or complete [mess-ups] and self-doubt. My advisors and mentors, formal and informal, help me navigate and encourage me to continue.

I wouldn’t be where I am today without the support of a wide and varying group of mentors – from supportive bosses to industry experts, thought leaders and my parents.

I have always tried to tap into the knowledge and expertise of those around me. But the most profound impact that mentors have had on my life has come in the form of helping me unlock the confidence within me to embrace my own leadership style, and not just replicate the way I saw my father, my partner or other male business leaders act.

When we build up women, we give them permission to be themselves, instead of the female version of a male leader.”

Did you feel pressure to succeed, coming from a successful family business background?

“The pressure to succeed came more from within than from my family.

Earlier on in my career the pressure was much more of a challenge, but I knew that if I wanted to achieve great things that I needed confidence, resiliency, and time. The thing about confidence and resilience is that you can only build these qualities by going through tough situations that require you to be confident and resilient.

It was that mind-set that forced me to embrace ‘out of my comfort zone’ situations. I am now grateful for these moments, and I know that for every hard experience I overcame, I was one step closer to becoming more confident and more resilient. It’s really hard to not ride the rollercoaster of ups and downs. Today, my kids and partner give me the perspective I need to stay up and not take myself or my work so seriously.

I also set aside time early in the morning to meditate. This is the time when I free my mind of everything work related and just get present, or I try to. I often come out of meditation with more clarity, focus and energy.”

Do you have any advice for young people who want to start their own venture, whether from a business family background or not?

“Remember, this is your life, not your parents’. Make the decision that is best for you. Then, if you still want to do it, go for it. Embrace all that you have to offer and realize that no one else can do it, dream it, convey it, sell it, or create it in the same way that only you can.

Don’t fear failure. With every failure you are one step closer to success.

I would also encourage you to put the systems in place that will give you the greatest chance of success. The author of Atomic Habits, James Clear, says “You do not rise to the level of your goals. You fall to the level of your systems.” For me, this includes things like my daily meditation practice and regular touch points with advisors who hold me accountable.

The biggest career challenge I have faced has been fundraising for my latest startup.

Going into my pre-seed round, I wasn’t aware of just how bad the odds were of securing external funding from the angel and VC community. I had an MVP [minimum viable product], early signs of product-market fit and an exit under my belt.

I didn’t think raising would be easy, but I also didn’t expect it to be so hard. The reality is that less than 2 per cent of funding goes to women-led startups. If you’re a BIPOC founder, the odds are even worse.

So far, I’ve closed $400,000 in funding and, although it hasn’t been easy, I’ve grown in so many ways as a result of it. Which is often the case with roadblocks – they just force us to get creative, adapt and build the will to move forward.”

Responses have been lightly edited for clarity and length.

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