Meet Wendy Bennison, the O.G. of the North American Apparel Industry

With decades of experience building some of Canada's biggest brands under her belt, the CEO tells us about dealing with down days and remembering to stay a student.

Photos by Maxine Munson

Oakville, Ontario-born Wendy Bennison has worked for some of the biggest retail brands in Canada. Her humble beginnings were within in-store management which quickly led to more senior positions. As she’s continued along her career path, she’s steered household names such as Mark’s, Roots and Kit and Ace in the right direction. And she’s not slowing down any time soon, having landed (yet another) CEO role at underwear brand SAXX. It’s a story of growth, a passion for leading teams and smart strategy that best describes this savvy businesswoman.

GIRLS ARE AWESOME: Hi, Wendy. We know that your retail back ground is diverse, but how did it come about that you went from cashmere (at Kit and Ace) to underwear?!

Wendy Bennison: It’s very much about the places I have found myself in. More than anything, I’ve always been passionate about the product that I’m representing and the customer it serves. With SAXX, it’s a very cool, fairly young, Canadian-born, in fact, Vancouver-born brand. SAXX makes technical performance underwear that solves ‘comfort issues’ for guys. Some customers have even described this underwear as life changing!

You first started out in retail management. Was it always a goal to reach your current position?

It was never a goal to reach the position that I have now; I was never on a path to strive to become one particular thing. I’d say it’s good luck combined with hard work and great teachers around me; those steps linked together have me doing what I do today.

One of the things I’ve learned quite recently is the value of setting goals. For the first time 18 months ago, I went through a course that encouraged me to sit down and map out my personal, health, career and life objectives for the next 10 years. I had never actually written them down on paper before!

From your experience, what was the toughest obstacle in making the transition from a retail manager to a more senior position in the industry?

One of the obstacles I faced was transitioning from being on the same team as my peers to suddenly managing them—having my colleagues become my direct reports. I think there’s that automatic thought from others that you have all the answers and you feel the need to be smarter than you were yesterday, but you’re just the same person taking on new responsibilities.

A piece of advice that I think is important to take in is knowing that leaving a role behind and stepping into a new one means you are starting a brand-new job. Even if you’re with the same company, think of it as a new company. Because if you show up with the same mindset you had for your previous role, you won’t succeed in the new one.

Your career highs have been long-standing, but what about the lows? Have you ever faced situations where you’ve lacked confidence about your ability to fulfil the expectations required?

(Laughs) Well, that’s happened to me about a million times! I don’t go into any situation, particularly ones that I have never tackled before, without asking myself if I’m making all the right decisions. I think a healthy amount of self-doubt drives you to work a little harder, be a little smarter.

I seriously don’t think there has ever been a role throughout my entire career where I didn’t look at myself in the mirror and say, ‘’Jeez, do you really have this one, are you ready for it?’’ And I think the fact that you ask yourself that question means you never lose that little shred of self-doubt which keeps you sharp.

Being in a demanding role, what’s your coping mechanism if you have a bad day at work?

I take a big breath, stop for a moment, sometimes walk around the block to clear my head or make myself a strong cup of tea! We’re all human beings and some days emotions do ride higher than others.

Yes, as a leader people do look to me as an example, but there are days when you feel the pressure, too. It’s OK to show your human side.

Have you ever felt your gender influence your career, particularly in the early stages when things were more male-dominated?

It’s not really something I have ever thought about, yet I know that statistically-speaking it is a factor. I work well with both men and women and I can be very truthful in saying that I’ve never been in the space of thinking, ‘Wow, I’m a woman so it might be harder to get to where I want to go.’

What’s been the pleasant discovery for me after developing into more senior roles is finding out how much having a female leader in an organization means to other women in the business. Women in particular have told me how much they appreciate having a role model – their words not mine – and someone to talk to, someone who is experienced. Raising a family and having a career, it’s been something that women have shared with me as being important to them. And I take that very seriously. I’m really proud and very conscious of that.

Ultimately, I have never found my gender in any way to be a barrier. In fact, I would argue in some cases that it has opened doors for me. I think fundamentally it is about how you show up and the energy you’re prepared to put in.

With two daughters, was it a juggling act to keep the work-life balance?

I am not someone who has gotten from point A to point B in my life by being a workaholic. I’ve raised a family and have two amazing daughters who are both in their twenties, now at the beginning of their own careers.

My family kept me grounded and I’m extremely family-oriented. I’ve always felt that you don’t have a work life and a home life: you have one life. I’ve spent a lot of time working hard and there have been moments along the way when I have been a little out of balance. Probably in both directions. When you’re working and you have kids, they get sick and you have to run home and care for them. That’s just life!

When you’re off boss lady mode, what does down time look like?

My down time is really chill, often spent with my daughters. Sometimes it’s just hanging out on the couch watching a movie together or having great dinners, travelling to great places. Family time is my favourite way of clocking out when I am not working. And being here in Vancouver, I take advantage of my surroundings. I just love being outdoors, breathing in the fresh air and leaving my car parked all weekend long, walking around this beautiful city, even when it’s raining!

Ever thought of creating your own clothing brand?

What’s interesting is that this has never once crossed my mind! I’ve always been so engaged in the work that I do. For whatever reason, the next opportunity kept coming to me with challenges that were so exciting that I never stopped to think about not saying yes to them.

I’ve been very lucky, though. Mark’s, Roots, Kit and Ace and SAXX were in their beginnings and all founder-led businesses, so every single one of the businesses I have worked with has an entrepreneurial culture within.

As a veteran who’s been in the game for over 20 years, what is key to ‘making it’?

Do more listening and less talking. It’s incredibly valuable to just pay attention and listen. And when I say listen, truly listen to what’s being said. I’m not just talking about people who work for you, I’m talking about generally, in the space around you. If you can come into a room as a student, if you can start everyday listening for what you can learn that day, I think it positions you for all kinds of great success.

Thanks, Wendy.