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How three generations pulled Harry Rosen through the pandemic

Larry and Ian Rosen discuss family communication when it comes to setting strategy for the menswear brand

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If effective communication is integral to maintaining good familial relationships, it might be doubly so if a family founds and builds a business together. It is triply so for the Rosen men, Harry, Larry and Ian, who have succeeded in nurturing an iconic Canadian menswear brand over three generations.

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Three is a good number for the Rosens, as this year, despite a global pandemic, Harry Rosen the brand saw online sales triple, in large part thanks to the founder’s grandson, Ian Rosen, fostering a digital revolution within the fashion house, thereby ushering it into the new world.

He is quick to point out, however, that he would be nowhere without the examples of his grandfather and father.

As a recent study by consultancy KPMG suggests, family-run businesses fared better during the COVID-19 pandemic, potentially because of the inherently common goals of the leadership team.

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“The biggest thing [grandfather] Harry has always emphasized is the importance of visual merchandising and how it signals to the client exactly what business you are in,” said Ian, executive vice-president of digital and strategy at the company.

“For example, if you want to emphasize lifestyle and head-to-toe dressing you would ensure you are bringing together sports jackets, tops, casual bottoms, even shoes into a single area. If you want to tell the client you are in the jeans business … why not build an entire wall showing off the brands, washes and fits?”

He adds that his time spent touring around Toronto’s Harry Rosen locations with his grandfather as a 15-year-old boy is part of his most essential training, as well as his greatest memory. Harry’s philosophy, Ian said, is founded on the idea that there will always be a role for curation and personal, genuine recommendations.

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“Just the same as you will likely read a book or try a show that a friend suggested, he always felt that our team had to be that trusted partner when it came to style,” explained Ian. “To bring this to life, whenever a regular client walks into a Harry Rosen store, he is often met with a curated selection of items in his size and to his taste.”

Ian said his grandfather named this practice a “laydown” and the brand’s clothing advisors have been trained to fulfill it for more than 60 years.

The process of joining a family business is far from straight-forward. … It isn’t the most normal thing to have your dad become your boss.

Ian Rosen, grandson of Harry Rosen founder

From Harry’s generation to his son Larry’s, strategic direction evolved. Larry is a strategic leader, Ian said, which allowed him to standardize and scale some of the practices that Harry used to build loyalty in the early years.

“You can’t scale a concept like our approach to made-to-measure, our client service standards, or our alterations expertise without trusting your leadership team and developing culture that establishes and protects high standards,” explained Ian. “This idea of setting a vision and realizing the outcome with your team is something I know I have picked up from Larry.”

For his part, Larry attests to the ways in which all three generations have blended their practices together for success. He asked to join his father in the family business when he was a young lawyer in the 1980s.

“My father welcomed me into the business in 1985,” recalled Larry, chairman and chief executive of the company. “He mentored me and ensured that I had broad exposure to all aspects of the business. He was very supportive of me and never demanded that I be like him. He always made me feel like I should just be my own type of leader. He is almost 90 today and still is my inspiration.”

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Innovation in the younger generation

Larry encourages originality and innovation in his son, which he sees as being aligned with what Harry taught both of them.

“I really didn’t want him to be another me,” said Larry. “I wanted him to represent his generation. I wanted him to make us a modern digital company and to push us to change in ways that I know I was reluctant to do. He’s done all that in a very inspirational way. He shows remarkable respect for our heritage, our colleagues and our brand. But he also keeps pushing us to modernize and to be the type of company that men his age will gravitate to.”

The ideas Ian put forth, particularly during the pandemic, have translated into state-of-the-art e-commerce and digital outreach. When executive, C-level men shifted to casual wear at the onset of the pandemic, Ian worked to overemphasize that Harry Rosen is in the casual wear business. The digital tools the brand developed made online shopping faster, and he said this was an appropriate extension of a massive digitization the business has undergone since 2018.

“We knew that replicating this experience online could be a secret weapon,” said Ian. “The Clothing Advisor App we’ve developed called Herringbone (named after my favourite fabric pattern), allows our clothing advisors to curate for each and every client. The client simply needs to confirm the selections and check out.”

Online business took off with the app, and the company says it saw three-times growth in e-commerce in 2020, but Ian is direct when it comes to the personal and professional identity shift that comes with being part of a family business.

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“The process of joining a family business is far from straight-forward,” said Ian. “It isn’t the most normal thing to have your dad become your boss.”

He was encouraged to first pursue a career outside of Harry Rosen when he completed his undergraduate program at Ivey Business School. After some time in strategy consulting with Bain and Company and a boutique firm called Secor Group (now owned by KPMG), Ian felt he was established in a unique professional style and point of view. This brought a new perspective to the menswear company when Ian came on board, and also added to the family dynamic.

“When I took the plunge and joined, I feel there was a mutual respect that has continued to grow between Larry and me. I got to see my father in action (he’s not the same guy as around the dinner table!) and he got to appreciate the point of view I brought when it came to digital transformation.”

Shared ambition

Ian said the three generations are suited to each other when it comes to professional interests, which bodes well for strategizing when it comes to the bare bones of the retail game – supply and demand. He notes that they start strategy discussions by establishing a shared ambition – which guides their decisions, especially the tougher ones.

“We generally will spend one to two days discussing all of the implications that come from chasing after that ambition, including how much risk we’ll be taking on, what dependencies there might be, and how much capital will be required,” explained Ian. “During these sessions we often speak at length about what we call one-way doors – if we go forward with this, there is no going back. We never drive forward unless something is near unanimous and we strongly encourage our executive team to challenge the thinking at every turn.”

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In reflecting on the retail business and the Rosen family’s intergenerational success, experts in the industry say the family’s strategy is finely tailored.

“One cannot build a lasting family luxury iconic brand unless one is authentic,” said Diane J. Brisebois, president and chief executive officer of the Retail Council of Canada. “They have been steadfast in building a luxury retail business that has treated both employees and customers as family members. They have been able to maintain a high level of quality in fashion and, while differentiating themselves through their products and personal service, they have stood out because of the passion and respect they share with their team and the communities they serve. That cannot be faked.”

Part of their finely honed strategy comes from never being out of touch with what is happening in each of their stores, the Rosens said. Before the pandemic, Larry and Ian still visited a store each month with Harry, something they aim to continue as public health restrictions due to the pandemic allow.

Focus on inclusivity

Beyond the pandemic, the past few years have brought upheaval and new understanding around racial and gender-based issues, and the family wants to ensure that they are leaders in inclusivity and awareness.

“Whether it was a friend trying to find the right way to come out in the workplace or seeing someone’s choice of language really discourage a female colleague of mine, each and every time I came to the table to listen rather than speak, I walked away much more understanding of the privileged position I am in,” said Ian.

“As the father of now two little girls, this feels all the more real. … My hope is that I can help drive that same level of openness across our entire organization through internal councils and policies [and through] contributions in these areas financially and, of course, vocally. “

He adds, “While I’m proud of the diversity of perspectives and backgrounds we have on our team, I’m confident we can and will do better.”

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