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Drew and Jayne Woolcott

Drew Woolcott, founder of the Hamilton/Burlington, Ontario-based Woolcott Team, has not always worked in real estate. In the late 1980s and early 1990s, he ran a swimming pool service company, which he grew to a significant scale.

In the off-season, he would renovate and resell houses, compelled by an innate love of all things real estate. Woolcott was looking for a way to transcend the seasonality of the service business and seeking more blue-sky opportunities.

Drew and Jayne Woolcott lead the 40-person Woolcott Team in Ontario, Canada selling more than 6,248 homes and more than $2.7 billion (Canadian dollars) in sales since 1993.

Eventually, in 1993, he began a full-time career in real estate at RE/MAX.

“My father was in real estate, so I had some insight into his perspective,” Woolcott said. “I earned my real estate license eyes wide open and began my real estate practice with high hopes.”

Realizing that he could not be successful without the proper systems and support, he recruited his wife, Jayne, to develop an innovative team system. Together, they built a model that distinguishes the sales agents between listing and buying agents and includes a full roster of administrators, marketing and management — all with specialist roles.

Woolcotts Feel eXp’s Cloud-based Model Very Forward-thinking

Today, the 40-person Woolcott Team is one of the most productive brokerages in Ontario, having sold more than 6,248 homes and completed more than $2.7 billion (Canadian dollars) in sales. Recent sales range from a luxury three-story brownstone townhome in the waterfront city of Burlington, to a bungalow overlooking farmers’ fields in rural Flamborough, to a mid-century Hamilton home designed by Toronto architect Jerome Markson, which sold for $2 million (Canadian dollars).  

The Woolcotts did not hear about eXp Realty until early 2021, when their team was working with real estate coach Mary-Anne Gillespie. 

“She knew we were unsettled and she mentioned eXp Realty,” Woolcott said. “We were referred to Patrick Ashby, who was instrumental in the conversation, kind of a maven of eXp. We loved the simplicity and leanness of the model.”

The Woolcotts were impressed by eXp’s slideshow presentations and demonstration of eXp World, the company’s cloud-based campus that offers live training, real-time support and international collaboration. 

“We thought that going forward, it is obvious that having a cloud-based operation is more conducive to doing business in pandemic times,” Woolcott said. “It seems like the pandemic has expedited what might have been coming down the pike. Rather than sit by the wayside and watch everything change, we decided to join eXp and get ahead of the curve.” 

eXp’s Agent-centric Business Model Sealed the Deal

What ultimately convinced them to join eXp, though, was the company’s agent-centric business model.

“There’s a lot in it for the agents, I think,” Woolcott said. “It’s a little less expensive for them to operate in the way that eXp is set up. There are other opportunities for income, like the stock option plans and opportunities for revenue share.

eXp is a technology company, essentially. It is not burdened by all the expenses of massive brick-and-mortar operations. It is lean, which means it’s competitive.”

Read why revenue-sharing is better than profit-sharing

After joining eXp in April 2021, they expect to expand opportunities for their existing team members, attract more agents, better serve their existing clientele and cover more territories. 

Through eXp World, the Woolcott Team looks forward to attending meetings, weekly classes and conferences.

 eXp’s commitment to learning, the acquisition of SUCCESS Enterprises and partnerships with real estate thought leaders, Woolcott said, “I think those are excellent affiliations and that was part of our reason to move forward. eXp seems to be attracting innovators in the industry and that’s where we need to be in order to be competitive.”

Learn more about Drew Woolcott:

Years in real estate: 28 years  

Gross sales and transactions in 2020: 500 closed on $385,173,952 (Canadian dollars) gross sales

Brokerage history:

  • eXp Realty (April 2021-current)
  • RE/MAX (1993-March 2021)

Main territory: Ontario (Burlington, Waterdown, Hamilton, Ancaster, Dundas, Flamborough)

Main focus: Residential resale, investment properties, first-time buyers, move-ups and downsizers 

Number of people on team: 28 licensed agents, seven administrative staff members, two home stagers and three inside sales agents 

Accolades, accomplishments & awards: 

  • RE/MAX Circle of Legends, Lifetime Achievement, Hall of Fame, Diamond Club and Top Ten Teams in Canada 
  • No. 1 RE/MAX team for residential real estate transactions in Ontario

What makes eXp special to you? 

“Multiple sources of revenue streams, streamlined corp, heavy technology investment.”

Best tip to share with other agents:

Play the long game at all times and be persistent.”

What would people in Ontario say about the Woolcott Team brand?

“I think it’s what we hear from the public, that we’re hardworking, detail-oriented and above all else, honest and thorough.”

What does the eXp brand mean to you?

“Essentially, it means technology. We’re excited about the move. We’re looking forward to growing and thriving under the eXp umbrella.”

9 Fun Things About Drew Woolcott

What is your idea of perfect happiness?
Applying myself to a worthwhile cause, aiding others in doing the same and watching the reward of the application pay off.

Who is the person you most admire?
My father, who bore tremendous adversity and grew.

One thing you can’t live without?
A dream.

One trait that has led to your success?
Persistence — I stay the course.

Pet peeve?
People who will not do what it takes to become what they are capable of becoming

Little known fact about yourself?
I love to be alone, but never am.

Song you never tire of?

Any Bob Dylan song, but “Sarah” in particular.

Favorite meal?
Saturday night steak.

Your epitaph will say:
He was a good man.


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These figures are not a guarantee, representation or projection of earnings or profits you can or should expect. They also do not include expenses incurred by Agents in operating their businesses. eXp Realty makes no guarantee of financial success. Success with eXp Realty results only from successful sales efforts, which require hard work, diligence, skill, persistence, competence, and leadership. Your success will depend upon how well you exercise these qualities.

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