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Meet Cailey Heaps, RBC Canadian Women Entrepreneur Awards Excellence Finalist

Cailey Heaps sits at the helm of one of the most successful real estate brokerages in the country, the Heaps Estrin Real Estate Team. Thanks to her steady leadership, strategic vision, and unwavering commitment to her clients, the Heaps Estrin Team lands in North America’s top 1% of realtors yearly. A master in the art of negotiation, Cailey brings more than 20 years of experience to every transaction she overseesCailey worked in advertising after earning a Bachelor of Commerce with a major in Marketing. She was able to transfer her well-honed advertising skillset, business acumen, and marketing savvy to the residential real estate market when she joined her mother, Heather Heaps’ successful real estate business in the ’90s. Since then, Cailey has become a top producer, gaining significant market share as President, CEO, and Broker of Record of central Toronto’s top real estate team. Cailey is recognized as a trailblazer and an industry-wide thought leader, regularly sharing her insight at media events nationwide. She is a member of the Young Presidents’ Organization (YPO), the American-based worldwide leadership community. Cailey has always been a fervent supporter of numerous charitable organizations.


I knew I wanted to be an entrepreneur when… I was working in other industries and I realized that there are people who are happy doing a job, leaving every day and restarting the next day — they had a “routine” approach to work. I am extremely passionate about what I do, so I could never just step away each day. I constantly think about what I want to do next, how to improve the business, innovate our industry, etc. Also, I don’t know that I would love working for someone else — other than our amazing clients!

Entrepreneurship is made for me because… it satisfies my desire to be a decision-maker and my bias for action. It allows me to collaborate and innovate with my team, to study and learn from others, and to indulge my hunger for human connection.

The impact I hope to make through my work is… ideally, to innovate and change our industry for the better; to breed a community that recognizes the importance of human connection; build a business that works to alleviate the stress that is inevitable in a real estate journey through offering strategic consultancy as opposed to a sales mindset; and support charitable giving.

One of the most important lessons I’ve learned on my entrepreneurial journey is… I feel there are about a million things that I have learned, so it is hard to choose just one. I suppose it would be the importance of who you surround yourself with. It is so important to be surrounded by people who push you to do better, who have diverse backgrounds and experiences, and who are invested in the success of the business and who are willing to stand up for what they believe in.

My proudest accomplishment is… balancing work, family, and friends. Although I am not perfect, I am immensely grateful to have had the time and experiences I have with my family and friends.

The biggest risk I took that paid off was… probably starting the company as it is known today. My Mom was an amazing realtor and I took the foundation of what she had demonstrated and taught me over the years and then grew the business into the Heaps Estrin Team. Our growth since 2010 has been approximately 1800%.

My biggest setback has been… I can’t think of one specific setback — when you are running a business, you come up against barriers and challenges all of the time. I have learned to process these challenges over the years. I try not to react in the moment but rather take the time to approach it from different perspectives. I also meditate a fair amount now!

The best advice I’ve received as an entrepreneur was… while I have been given tremendous advice over the years, I think the most important lesson I have ever been taught was through my parents’ role modelling. They made it very clear that everyone should be treated equally — whether it is the President of a company or the person who cleans the office — they are all important and deserve to be treated with kindness and respect.

I surprise people when I tell them… I like camping and five-star accommodations equally — it’s the in-between I struggle with!

If I had an extra hour in the day, I would use it to… spend time outdoors with my family.

If you googled me, you still wouldn’t know… that I am naturally shy. I was born shy and have taught myself to work through it, but I still feel intimidated walking into a crowd.

The future excites me because… there is so much more to accomplish! I am excited to learn from other industries and leaders, I am keen to continue to change the way that our industry operates, and on a personal level, the last few years have been a time of immense personal change (and growth, I suppose), so I am excited to see what the future holds for myself and my children.


Connect with Cailey on LinkedIn and follow the Heaps Estrin Real Estate Team on Instagram @heapsestrin and @thelobbybyheapsestrin.