✨Team Highlight: let’s meet Kaitlin Chidley!

Kaitlin joins Bear as part of our new sales team, bringing deep expertise and enthusiasm that inspires us all.

October 7, 2021

In addition to hiring, training, coaching, and managing sales teams at a whole range of companies, Kaitlin is always ready to hit the front lines herself. She’s proving her chops in no time, while keeping compassion front of mind. She’s already lighting up the phones, so we were lucky to get a few minutes of her busy schedule for a chat.


Welcome to the team! What are you most excited about as you start at Bear?


Wow… there’s just so much excitement around joining the Bear team! First off: the actual people who make up the DNA of the company. The team might be small right now, but they are oh-so-very mighty, passionate, and hungry. Our fearless leader and CEO, Sam Vlessing, has lived and breathed the challenges of our online merchants. His vision for Bear and the team he hired to give it legs — we’re going to do big things. I can’t wait to get our story out into the world and start to truly help others knock their ecommerce strategies out of the park.


What drew you to pursue sales as a career?


I love the art of conversation and psychology that goes into selling. Everyone has different perspectives, our industry will continue to evolve, and new obstacles will always arise. Sales is constant learning and I love that.


What are your “words to live by” professionally?


Everyone is human. This might sound silly, but in a world where technology and automation is exploding, we can’t forget that we are complex beings driven by emotion. If you have humility and compassion for what others in our world today are experiencing, I think you’ll enjoy your days more by doing so.


What’s your ecommerce marketplace of choice?


Wayfair. I love buying furniture through Wayfair. I know that they have my back no matter what as a consumer. I’ve been a fairly regular customer since 2018 and don’t have any plans to return to shopping in-store for my furnishings. 


What’s your favourite piece of furniture?


A burnt orange papasan chair that I purchased from my pals at Wayfair… it’s my cozy reading nook.


What’s your go-to downtime activity?


Reading, kayaking, camping, yoga, baking, wandering around Toronto in search of coffee and treats…




We’re sold! Welcome to the team!

✌🏼🐻

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