Under Gillian Stein’s leadership, Henry’s has transformed from a traditional electronics retailer into one that encourages and builds on its customers’ creativity and passion.

And her journey to the role as company CEO was a natural progression in her career as she eventually took over the family business.

Henry’s was founded by her great grandfather in 1909.

“Growing up in the business I would have spent my PA days and weekends and special events things like that, I would have spent lots of time helping out in the store. But I would say the biggest part was the conversation around the dinner table. Every night we would have talked about what was going on in the business, what kinds of deals were going on. Even when I was little my dad (Andrew) was always talking about the deals that he was making. He loved a good deal,” said Stein.

“And whether it was understanding what was going on with customers, with products, with the bank, all of those pieces would be something we would talk about at dinner.”

Stein was born and raised in Toronto. She did a Bachelor of Commerce at McGill University then a Masters in International Development at the University of Sussex in England.

Stein is a strong believer in education. She’s also taken Project Management at York University, the Graduate School of Business Executive Program at Stanford University and the YPO Presidents Program at Harvard Business School.

“I love learning,” she said.

“I don’t know where that came from. I’ve just always been somebody who likes learning and I’m curious and I like to ask a lot of questions. And I love the executive programs, that style of learning, because it’s all case studies and you get to dive deep into a company and analyze it. But it’s also that I’m sitting around the table with a bunch of other CEO’s. So we all get to dive in together and I get to hear what they think of a company and we put our minds together and come up with something and the professor usually comes and blows our minds with something totally different. It’s fun.”

When she first started at university, Stein was in accounting and quickly made the switch to marketing because she realized she was far more of a creative mind.

“And then I actually augmented it after taking the business piece, I went and did international development. I had a real interest in corporate social responsibility. To me, it was about blending these two worlds of business and how do you make business sort of come back to the family values and growing up in the family business that the business can have a really positive influence on the communities that you live in. So how do you make business a force for good and that’s where that international development piece came in.”

Stein spent the first part of her career working in corporate social responsibility.

“When I first graduated from undergrad I worked in the business. I worked in accounting. I worked in marketing. And I spent some time at the front cash which is good to learn what that experience is like. It’s important,” she said. 

“But when I graduated from doing my Masters I actually worked at the UN (United Nations) in the Division for the Advancement of Women. I worked on gender Issues.”

Growing up surrounded by so many incredibly talented photographers, she never considered herself a photographer but she had a love and appreciation for the art.

“I did enjoy it and I dabbled in it in high school. In university, I had a dark room. I absolutely was into it and enjoyed it but I’m nowhere close to the level of experts that I’ve been surrounded by growing up,” she said. 

Retail is hard and growing up watching her father, seeing the level of stress that he had, scared Stein. It wasn’t something that made a young person want to follow in those footsteps. At that point in time, her father was working incredibly long hours, six days a week. The only reason he didn’t work seven was because stores were mandated to be closed on Sundays. 

“And my dad had a heart attack when he was really young. He was 47 when he had a heart attack. And so to me retail was not something I wanted to get into when I was younger. That wasn’t the path that I thought for myself. I always had a ton of respect and passion and admiration for the business but it wasn’t something I wanted for myself,” said Stein.

What changed?

“I changed and the business changed. I think it was important that I forged my own path and so I built my own career, particularly spending time, the last role I had before I joined the company I worked in ESG investing long  before anybody knew what ESG meant,” she said. “What was amazing was coming up with ways in which you could actually objectively rate a company’s ESG performance. It was fascinating and I spent a lot of time looking at different cross sections of companies.

“But the thing I kept coming back to was that it was the values that I had were the values that the family business had. So a combination of the experience in ESG investing along with doing a lot of work in project management at that point I felt Henry’s was in a position where I could bring value. That was really important for me. If I was going to work in the company I wanted to make sure that I was adding value and if there was a role and I wasn’t there just because of my last name.

“For me it was recognizing that I could actually work in a company that espoused the values that I felt so strongly about and I could bring my experience in project management and did a lot of work in strategic initiatives when I first came back. So it was a combination of both the business changing and myself growing into the roles.”

As a people-first leader, it’s important to Stein that her role extends well past driving the bottom line. Corporate social responsibility and employee well-being are critically important to her.

“I am a very collaborative leader. Something I feel very strongly about is vulnerable leadership and really making sure that I bring my whole self to work every day and people see me as a human that’s approachable, that they can relate to,” added Stein. “I feel very strongly that you need to be able to put your ego at the door, check it at the door, and you can surround yourself with people who are smarter than you.

“To me it’s about hiring and finding experts in their respective fields and listening to them. My job is to bring those people together to solve problems but I’m not the one that’s going to be the smartest person who is going to be able to say this is what we need to do and why.”

When it comes to a family business, there are more emotional dynamics going on than a ‘regular’ business. Stein said it’s important to be able to set boundaries.

“We get together every Friday night with my extended family for dinner and it’s important on those nights that we don’t talk about business or at least don’t only talk about business. It’s hard not to talk about it at all but it is important because we all need to have some boundaries. I’m not going to suggest that when you’re a CEO you can just shut off work but we all need to have a little bit of work life balance especially when your kids are around. It’s great for the kids to hear about business and to learn but you also need to make sure that you can talk about other things. Boundaries are important,” she said. 

“And being able at times to take the emotions out of it. In some way the emotion is helpful because it allows you to think longer term, your legacy is important. So sometimes it will help your decision making but at other times you have to be able to put that aside and say no this is a business and I’m going to treat this like an asset and take that emotional tugging out of it.”

Stein is an advocate for mental health and has been recognized for her work to reduce the stigma associated with mental health in the business community. In 2022, she was a recipient of the Top 25 Women of Influence award. She has been open and public about her bipolar disorder.

“The stigma is still so very real, particularly in the business community. People don’t talk about it. Statistically we know it’s impossible that I’m the only CEO with a mental health diagnosis. We know that’s impossible. Yet I’m the only one who has been public about it,” she said. “And so we need to set an example for people where they can feel psychologically safe at work . . . We want our employees, we want everybody to be as engaged and feeling as well as possible so that they can contribute and be productive.

“But somebody needs to set that example and that modeling in leadership is really important. I felt that was an opportunity that I had because of the position I was in and if I didn’t take it then shame on me.”

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