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Women Leaders Of Real Estate: Caily Heaps of Heaps Estrin On 5 Things You Need To Succeed In The Real Estate Industry

Invest in the community. Taking a genuine interest in your team, your community and your industry is the only way to motivate change and build connections that lead to success.

As a part of my series about strong women leaders of the Real Estate industry, I had the pleasure of interviewing Cailey Heaps.

Cailey Heaps is a seasoned Managing Director and property professional with over twenty years of experience in residential real estate across the Central Toronto Core. After graduating with a BCOMM, majoring in marketing complemented by a minor in human psychology, Cailey started her career in advertising prior to joining her mother, Heather Heaps in the 90s in her real estate business. Having come from a dynamic and entrepreneurial family, Cailey quickly became a top producer and has since gained significant market share to become the leader of the top real estate team in central Toronto.

The key to her success revolves around her commitment to the client experience and achieving sales results to match. A keen speaker at international conferences and one of the most respected voices in the Toronto property market, Cailey is passionate about exploring new and innovative ideas to improve the real estate industry.

Thank you so much for doing this with us! Can you tell us the “backstory” about what brought you to the Real Estate industry?

The simplest answer is my Mum. When I was 10, we moved from BC to Toronto and she started working. She loved bringing people together, brokering deals unofficially from a park bench. Eventually, that evolved into a successful real estate offering with my mom working as a single agent. I didn’t set-out to follow in her footsteps, but after earning my degree in commerce and a short stint in advertising, I eventually joined my mother’s business as an assistant, accepting her guidance and mentorship. Under her tutelage, and with her core values intact, I worked diligently and turned Heaps Estrin into a bigger business, leveraging my marketing experience along the way.

Can you share with our readers the most interesting or amusing story that occurred to you in your career so far? Can you share the lesson or take away what you took out of that story?

There have been so many! One of the most memorable experiences happened when I first got my license. I met my clients to do a showing and caught teenagers playing hooky from school in a compromising position. To this day, I never start a showing without calling out to see if anyone is home first.

The other thing I learned early on is that being aggressive at the negotiation table serves no one. Everyone at the table has a common goal, so deals brokered through kindness and patience have a better chance of ensuring our clients’ satisfaction and happiness.

Are you working on any exciting new projects now? How do you think that will help people?

I’m really passionate about helping our future leaders. I am currently working on a program that champions diversity in business. The program will focus on partnering kids with industry leaders

from all different professions — everything from marketing and advertising to medicine. They’ll act as a resource for practical guidance and advice, but most importantly, they’ll help them navigate making choices as they prepare to enter adulthood.

What do you think makes your company stand out? Can you share a story?

First, Heaps Estrin runs as a team. Instead of hiring an individual associate, our clients get a team of experts with exceptional experience in the market. It’s not the typical brokerage model where individuals are steered to be uber competitive. Very few real estate agencies work under this model. My team is equally invested in the success of our business. Everyone is committed to working hard and that’s demonstrated beyond day-to-day tasks. We live, work and play in the communities where we live and specialize in and often participate and give back to our neighbours. From ice cream socials to raise money for local causes to the #SilverLiningProject our team organized to raise much needed funds for Community Food Shelters Canada during COVID-19, my team and I are passionate about giving back.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

I hope it doesn’t sound cliche, but my Mum. She was an absolute pro, but was so humble and genuine. It wasn’t money that motivated her — — she was invested in the community and loved helping people. After living in Saint Lucia, the island became a special part of our family’s story. During a visit, she started working with Grow Well — a charity that serves as a drop in centre for children. She was so invested that she volunteered during every trip, she even made it her mission to have guests on the island donate financially to support the charity.

My Mum was also a great example of a woman who could handle anything. Four kids, a thriving real estate practice, countless friendships and volunteering — and she did everything with a positive attitude.

Ok. Thank you for all that. Let’s now jump to the main core of our interview. The Real Estate industry, like the Veterinarian, Nursing and Public Relations fields, is a women-dominated industry. Yet despite this, less than 20 percent of senior positions in Real Estate companies are held by women. In your opinion or experience, what do you think is the cause of this imbalance?

I hesitate to speak on behalf of all markets, but certainly in Toronto, where I live and work, two of the largest real estate firms are owned by the same company, and the leadership team is largely made up of men. While this may not be intentional, it does demonstrate that there is work to be done. Fortunately, Royal LePage has good female representation at the executive level.

In general, real estate is a demanding field that requires a great deal of personal sacrifice, especially in the early stages of your career. Late nights, long hours and weekends are all part of the gig, so like other professional women, balancing work with family obligations without the appropriate amount of support is challenging. That makes climbing the ladder at some of these larger real estate companies challenging.

What 3 things can be done by a) individuals b)companies and/or c) society to support greater gender balance going forward?

Most importantly, leaders need to create a culture that promotes equity and inclusivity. Take the initiative to explicitly share your values and hold your team to the same standard. Denounce harassment of any kind and legitimize policies that promote equity and inclusion in organizational documents. Hold management to account.

This is obviously great in theory and is definitely the bare minimum. In my opinion, what happens next is the most important. Create opportunities for women, promote from within and identify a career path that moves toward leadership.

Finally, mentorship and training. Mentorship is so important. Senior members of teams should be paired with junior or entry-level agents. Invest in training and encourage women in your organization to learn all aspects of real estate by assigning diverse tasks. This helps with growth and development.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

One of the biggest challenges, believe it or not, lack of support from other women. Executive women are often encumbered with daily duties and responsibilities proving their ability that they don’t take the time to mentor or support their junior counterparts.

Can you share 3 things that most excite you about the Real Estate industry?

People, people, people! I love knowing that as a team, we can have a meaningful and tangible impact on our clients’ future — from the place they call home to their finances. We regularly challenge, collaborate and create opportunities to change outcomes.

Can you share 3 things that most concern you about the industry? If you had the ability to implement 3 ways to reform or improve the industry, what would you suggest?

One major issue is the amount of affordable inventory. It would be great to have a model introduced where qualified buyers can rent-to-own, this will keep more people in the city.

Competition in real estate has always been fierce and the number of agents is continuously growing. It would be nice if all agents operated at the same standard of ethical behaviour and work so that there is consistency across the industry.

I believe that eventually the single agent model will fade in favour of a team structure like ours. Given the economies of scale available when you work as a team, the longevity of individual agents will be challenging in the long run.

What advice would you give to other leaders to help their team to thrive?

I’m not an expert, but I do believe there is weight in having and sharing a strategic vision that your team can buy into. It’s also important to be open to honest feedback from your team — it facilitates an environment that is open to collaboration and only makes the organization better in the long run.

Ok, here is the main question of our interview. You are a “Real Estate Insider”. If you had to advise someone about 5 non-intuitive things one should know to succeed in the Real Estate industry, what would you say?

First and foremost, you’ll never go wrong focusing on the client. My Mum and mentor was never financially-motivated and although this is my career and source of income, I approach every situation with what’s best for the client.

Real estate is all about client service so having high emotional intelligence is imperative. The ability to consistently forge positive relationships with clients and peers will result in good opportunities based in trust.

Research! Don’t assume you know everything about the market. It’s important to know the market inside and out and understand the inventory.

Have a plan in place. Plot out what you need to achieve success and the steps that you need to take to get there.

Finally, invest in the community. Taking a genuine interest in your team, your community and your industry is the only way to motivate change and build connections that lead to success.

Because of your position, you are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the greatest amount of people, what would that be? You never know what your idea can trigger. 🙂

I believe we have a long way to go to reach diversity in the workplace. We need to develop more mentorship programs and they need to be more prolific and far reaching. Regardless of racial background, kids don’t understand what opportunities there are in the world. Starting mentorship programs early will hopefully offer youth a better vision of their future and guidance on how to get there.

How can our readers follow you online?

Readers can visit us online at https://heapsestrin.com/ or on Instagram at https://www.instagram.com/heapsestrin/.


Women Leaders Of Real Estate: Caily Heaps of Heaps Estrin On 5 Things You Need To Succeed In The… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.