Meet Charlie Steip, an insurance agent you’ll actually enjoy talking to. 

Charlie is the client service advisor at Highcourt Breckles Group in Collingwood, and his belief that insurance is more than a mere transaction is what sets him apart. 

"Insurance can be so rigid," said Charlie. "I think people appreciate someone who brings a human element to it."

While Charlie has almost two decades of experience in the industry, his commitment to making insurance more accessible and enjoyable stems in part from his personal life as well. 

Charlie identifies as queer, and he said first and foremost, he is a partner and a parent. 

"A big part of my identity is my queerness, and it's something that applies largely to my business philosophy too," he said.

Charlie came out as transgender during COVID, crediting the extra time stuck inside which forced him to sit with his thoughts as the catalyst. While he came out as gay in high school and found he could express a lot of his masculine side through that, looking back, he realized he was putting off the inevitable. 

“I was really good at hiding that aspect of myself from myself,” he said. 

With one child already and another on the way, Charlie understands the importance of a strong support system and strives to align his career with his personal life. As an insurance professional, he also brings a unique perspective to the field, embracing diversity and inclusivity in his work. He understands that each person's situation is unique, and he brings empathy, inclusivity, and sensitivity to every client interaction. 

And his clients love him for it. 

"My main thing is to make it an enjoyable experience. Base it more on relationships," he said. "You are trusting me with some pretty huge stuff, so we should probably get along."

Nevertheless, Charlie's journey to his current role is the result of years of hard work and experience.

Charlie grew up in Oakville, and after graduating high school, his mother said he either needed to apply for post secondary education or get a job and pay rent. His family had always worked in insurance, so he said it was “an easy in” at the time. 

Charlie started his career as a billing clerk at a local insurance company, running the payment remittance machine in the accounting office. “It was mind numbing,” he laughed.


From there, he worked his way to the company’s head office, where he worked as an associate system analyst in the IT department. But something was missing: There was no human element. 

So, in 2016, Charlie decided to try his hand at the sales side of things. He obtained the appropriate licenses and became an insurance agent with Desjardins Group selling home, automobile and business insurance in Oakville. 

In his personal life, Charlie always knew he wanted to escape the suburbs — trading traffic lights for a more active lifestyle. Charlie’s wife had strong ties to the South Georgian Bay area, so in 2017 they moved to Thornbury and Charlie took a job at another Canadian Insurer. He obtained his mutual fund license and started shifting into more of a financial advisor role, but in his heart he knew the financial side wasn’t for him.  

“I am insurance,” Charlie laughed. “I always will be.”

Fortunately for him, so was his colleague, Julia White. So when Julia was approached by Highcourt Breckles Group last year and asked to spearhead a new Collingwood branch, she said yes. 

But only if she could bring Charlie with her. “We were always such a good team,” said Charlie. 

Highcout Breckles is a full-service brokerage based in Markham, which made the transition even more appealing to Charlie. He had started selling business insurance, but found he was hitting walls trying to help his clients. 

Moving to a full-service brokerage would allow him to better serve his community, he said, thanks to its expansive product shelf. 

“There are a lot of unique businesses in Collingwood that don’t fit into a box,” Charlie said. “I wanted to be able to work with all different types of businesses and offer solutions.”

They officially made the transition in July 2022, setting up shop at the Collingwood Foundry while they looked for office space in town. Having lived in Thornbury and worked in the area for the five years prior, Charlie realized he never really had a reason to come into Collingwood before. 

He said becoming a member at the Foundry at the same time was synchronic.  

"Collingwood was brand new to me. And very refreshing, to be honest" he said. "We thought we'd come to the Foundry temporarily and then being here has just opened up so many doors."

And not just in business.

Charlie has always been interested in the paranormal — so much so that he and his wife broke into a haunted house in Hamilton out of curiosity — but it wasn’t until later in life that he became spiritual as well. Signing on at Foundry opened doors and connected him to like-minded individuals, and has contributed so much to his personal growth as well. 

Now that he has almost a full year under his belt at the new firm, Charlie is excited to look forward. 

A big goal of his this year is to work with more unique, aligned and like-minded businesses, including queer-owned businesses, and helping them find the solutions they need. “All the things I am kind of drawn to, those are the people I want to work with,” he said. 

"It's just about doing it differently," he said. "Making it feel more personal."