Anatomy of a Leader: The Philosophy and Style Behind the Success of Indochino’s Drew Green [Feature]

Retail industry news delivered directly to you. Subscribe to Retail-Insider.

Leadership. What does it mean, exactly? By definition, it’s the act of guiding and directing a group. However, the skills that are leveraged to do so, and the characteristics that are intrinsic to each individual, vary, as do the outcomes of their unique efforts. To lead effectively, the perfect confluence of these skills and characteristics is required, along with a steely philosophy, confident decisiveness and steadfast commitment toward achieving success. And, although Drew Green, Chief Executive Officer and President of INDOCHINO, possesses the aforementioned set of attributes, he describes leadership as the ability to influence and maintain a buoyant culture while ensuring perpetual progression.

“It’s critical for any great leader to be consistent,” says the seasoned retail executive. “It can sometimes seem egregious to motivate and compliment when things are going well. But a true leader is someone who’s excited even when results aren’t so good. A positive attitude, especially during challenging times, goes a long way toward ensuring the persistence of any organization and helps to preserve a team’s focus. Supporting a positive and productive culture also requires a considerable amount of empathy. Some may think that’s a little misplaced given that we’re talking about business. But I don’t think it’s misplaced at all. A great leader is able to put themselves in the shoes of their team, partners, shareholders, stakeholders and customers, and really understand what they’re going through. And they’ve got to do this while making sure that they don’t get caught in the moment and that they’re always looking forward. I’m constantly questioning the work we’re currently doing to make sure we execute, but I’m also thinking about where I want the company to be 12, 24, 36 and 48 months out, and putting plans in place to ensure that we make the most of our opportunities.”

Passionate innovator

Decorated and honoured with a multitude of acknowledgements throughout his career to this point, including Ernst and Young’s Entrepreneur of the Year and INDOCHINO’s reception of University of Alberta’s Innovation in Retail award and Chain Store Age’s Breakout Retailer of the Year, Green has managed to build an extremely impressive portfolio of achievements and successes that set him apart from many of his industry peers. One of the earlier tech-savvy ecommerce innovators in the country, Green founded Canada’s very first multi-merchant online marketplace SHOP.CA, which was acquired by EMERGE COMMERCE in 2016 – a company that he continues to be a major shareholder and Chairman of. He’s also contributed significantly within leadership roles at the internet advertising company DoubleClick, SHOP.COM and e-marketing application service provider FloNetwork. In addition, driven by a deep-seated passion for entrepreneurial success, he’s an advocate for entrepreneurs across Canada and the founder, chairman, and/or investor in 30 companies that drive innovation and growth within and across multiple industries, including D2C ecommerce, omnichannel retail, insurance, esports, real estate, artificial intelligence, and financial, educational and property technologies.

On its own, the breadth of aforementioned work and contribution is enough to stand Green apart from most and merits the accolades he’s received for his tremendous professional accomplishments. However, when one layers on the fact that he’s also currently leading one of the most successful apparel brands in the world, his status based on his business triumphs elevates to something near iconic. Since he took over as CEO of INDOCHINO in 2015, the company experienced growth in excess of 500 percent, expanded its North American retail network and firmly established itself as the leader in the men’s custom apparel category. And although there are obviously a myriad of factors supporting Green’s uncanny knack of building and fostering the performance of fast-paced, high-growth companies, it’s his vision and unrelenting focus on, and adherence to, his philosophies that yield the greatest return.

“My formula – the way that I work and build a company – revolves around 5 Ps,” he explains. “And it always starts with people. It’s incredibly important to invest significantly in order to ensure that you’ve got the right people all the way through the company to guide and execute on your vision. Another important aspect of the retail offering is obviously product. Considerable attention has got to be paid toward bringing the best product within a category to market. And it’s defined by a number of different things. It’s not just about the end result. It’s about the experience, how quickly the product is received and the quality of the given item. Strong partnerships are also critical to any retailers’ success. You can know the business on your own and build a great team and live in an isolated world. Or, you can open yourself up to partners that you can make better and who make you better. There are often dozens of partners helping to support any great retail operation. Price is a constant factor as well, combined with the quality of the product and the experience that’s offered, in driving real value for the customer. And of course, a retail organization is not successful without generating profit. It’s challenging when you’re juggling so many different aspects of the operation, but you’ve got to maintain focus on the bottom line in order to keep everything else ticking.”

The rise of INDOCHINO


Applying his acumen and retail ideologies to INDOCHINO, Green led the company to 40 percent year-over-year growth between 2015 and 2019 and has been instrumental in positioning the operation for further growth post-pandemic. Providing a means by which men can create one-of-a-kind garments, including suits, shirts, chinos, blazers and overcoats, it has quickly become the leader within the made-to-measure direct-to-consumer space. Allowing customers to select from hundreds of fabrics and an array of lapel, pocket, button, lining and monogram personalization options, INDOCHINO helps men look and feel better, imbuing them with the confidence to express their own personal style. And, it seems, based on the tremendous growth of the company’s physical network, that its made-to-measure, omnichannel experience is going to become even more accessible to customers going forward. Opening on average one showroom per month since May of 2020, and with plans to launch a staggering 16 more by the end of July 2021, INDOCHINO will soon boast more than 80 physical showrooms across the country, building on the 52 locations that existed prior to the pandemic. 

There will also be an announcement in June concerning the launch of a major department store partnership that Green promises will be extremely exciting. He’s proud when speaking of the company’s growth and the incredible success it’s enjoyed, pointing to his team’s undivided focus on the customer as the primary enabler and catalyst of its continued achievements.

“We could talk about the mechanics of the business and everything that goes into it all day,” he admits. “But by maintaining our focus on the customer and continuing to make improvements to our service and offering, we’re making it easier for them to experience custom-fitted menswear. Ordering and designing your own suit is not uncomplicated. And we take great pride in removing a lot of the complexities on the backend and making the experience seamless and fun. So, much of the enhancements that we’ve made during the pandemic, as well as those that we have planned for the near-term, are really focused on making it even easier for the customer to engage and shop with us. And, although we’ve expanded our showroom network, we aren’t simply launching more of what we already offer. We’re continuously working toward improving on what we do and making the INDOCHINO experience a really memorable one for our customers.”

He recognizes one of the industry’s undeniable truths: the fact that without a loyal customer-base, it’s impossible for any brand to grow. It’s not a problem that the Vancouver-based retailer needs to worry about, however, as it enjoys the continued patronage of scores of devoted admirers. There’s no doubting the contribution that the company’s superior service has lent toward engendering such a dedicated community. But, as Green stresses, it’s also its unceasing desire to further develop the INDOCHINO offering that continues to propel the company forward.

“We’re really proud of, and continue to make improvements on, the speed with which we get our garments to customers,” he asserts. “Five years ago, we were operating with about four-to five-week delivery times. We’re able to deliver in two weeks now and will reduce that even further in the future. It’s not been an easy task to reduce delivery times while you’re actively selling, building and delivering millions of one-of-a-kind garments. But we’ve invested a lot of time into making that a core area of our focus, creating an even more seamless and expedient customer experience with the brand.”

Growth amid uncertainty

INDOCHINO Toronto – Photo by Dustin Fuhs

The continued growth and expansion that INDOCHINO’s experienced over the course of the past 14 months or so, during a time of great challenge when the efforts of most operating within the industry have been blighted by the impacts of COVID-19, are truly impressive and a testament to the company’s resilience and agility. Green recognizes the struggles that many retailers have been suffering through, referring to the past year as “one of the most difficult and disruptive moments in retail history”. However, he’s also quick to point out the fact that as a result of his team’s outstanding attitude and inspired performance, INDOCHINO has managed to not only survive the negative ramifications brought about by the pandemic, but to position itself for further growth in a post-pandemic environment.

“I’ve been really fortunate throughout my career,” he admits. “I’ve had the opportunity to work with a lot of great teams and lead a lot of amazing companies. But there has not been a year prior to 2020 that I’ve been prouder to work with a team of this calibre. I’ve always believed that when faced with adversity, to really succeed in anything, you’ve got to be able to take challenges and turn them into opportunities. And my team has really done that during the pandemic. Everyone understands what a massive impact COVID has had on retail. There’s been so much uncertainty and so much unknown. But we stuck together as a team, created focused and clear short-term goals and executed on them really well. As a result, as we start to move beyond the pandemic over the course of the next three to nine months, we’ll be bigger, better and stronger than ever. The enhancements that we’ve made over the course of the past year or so are going to pay dividends for the next decade and have made our opportunity to be a global market leader clearer now than it was prior to COVID.”

Coupling with the expansion of its physical footprint and continued growth in revenue, Green and his team are also paying a considerable amount of attention toward broadening its product offering beyond formalwear, recently introducing new categories that include custom casual pants, casual shirts, shorts and outerwear. It all adds up to what Green describes as “really exciting things” that are happening within the company, building relentlessly on the foundations that have made INDOCHINO such a massive success.

Inspired benefaction

One can’t mistake the confident assuredness with which Green approaches each task and challenge that he’s presented with. However, there’s also a very modest, compassionate and genuine air about him that seems to transcend his skills as a leader of businesses. They are qualities that are reflected in the charitable and philanthropic work that he does to benefit organizations and communities in need. Proudly born and raised in Scarborough, Ontario, Green is an active member of the Board of Directors at The Scarborough Hospital Foundation, which oversees a network of hospitals in one of the most underprivileged and underfunded urban areas in Canada. He plans to significantly redevelop this Canadian district in the decades ahead through an EMERALD CITY vision he’s developed. It’s a project that will require an inordinate amount of work, dedication and commitment in order to improve the city’s condition. But fortunately, they are traits that Green possesses in abundance, thanks to the education and influence of one of his biggest influences.

“Growing up, it was kind of just me and my mom,” he reflects. “A lot of my leadership strengths, as well as the personal qualities that I’ve developed throughout my life, have come from her. She was a teacher and a fantastic leader. I was always inspired by her and the work that she did to help guide young people to greater things. She was always focused on meeting and surpassing the needs of her students and to support their growth and improvement as people. The empathy and consistency with which she conducted herself with others had a profound impact on me and has gone a long way toward helping to form my character and shape the beliefs and philosophies that I live my life by.”

Inventory change

They are beliefs and philosophies that Green says consistently drive him to become better, both as a person as well as within the world of business. For the city of Scarborough and other causes that he’s involved in, it means they have a proven leader of decisive and passionate qualities in their corner, guiding and directing improvements. For INDOCHINO, it means more of the same. The company is constantly exploring ways to enhance the product, fabric assortment, communication with customers and the service it offers. But, as Green points out, there is also much needed improvements to be made with respect to inventory practices and management in order to better serve the customer and reduce the negative impact that the apparel industry has on the planet.

“The industry, and the way it operates, from an inventory perspective, needs to change significantly,” he asserts. “We can’t live in a world five or ten years from now the way we were operating pre-pandemic. The consumer of tomorrow is going to be buying less and buying higher quality and will want more personalized, customized and fitted garments. Sustainability is steadily growing in their minds, so retailers are going to need to think about ways they can create real-time inventory. The old world of buying 10,000 units and discounting them if they don’t sell isn’t going to work the way it used to. As a result, a lot of change is going to be required in the inventory and supply side of retail. And it’s going to be a great thing for the customer and the world, ending up in less waste and more sustainability.”

Continued growth and success

When looking ahead, it seems evident that Green and his team, leveraging the intense focus with which they operate, have positioned INDOCHINO well to capitalize on the opportunities of today as well as preparing the retailer for even further future growth. What the company has been able to achieve in such a short time under Green’s direction is really quite remarkable. And, when considering the complexities of the retail industry and the constant change and evolution that takes place within its confines, the company’s achievements seem even more impressive. But, as its venerable leader points out, understanding the inevitability of these changes helps keep the prominent made-to-wear menswear retailer on its toes as it continues to carve out a special place for itself among its community of customers and the global retail market.

“A business is a living, breathing organism that’s always evolving and transforming. And, combined with the fast-paced nature of the retail industry, it means we have to constantly anticipate these shifts, wherever they happen, and be consistently thinking of ways to make the experience a great one for our employees and customers. For INDOCHINO, we’ve got some really exciting things happening with respect to our product as well as the development of our partnerships. And we’re going to be accelerating our expansion in a really significant way over the next three months. The past year has been an incredibly difficult one. But it has also been the most rewarding of my career so far. The things we’ve done and the way we’ve executed on our vision over the course of the past 14 months or so are cause for real excitement. We’re in the process of building a global market leader and I’m really looking forward to our continued growth over the course of the next decade.”

Article Author

Sean Tarry
Sean Tarry
Sean Tarry is an experienced writer who leverages his unique storytelling abilities to bring retail industry news and analysis to life. With 25 years of learning, including over a decade as Editor-In-Chief of Canadian Retailer magazine, he’s equipped with a deep understanding of the unique world of retail and the issues, trends, and innovators that continue to influence its evolution and shape its landscape.

More From The Author

Out Soon: Retail Insider the magazine, Volume Two Issue One

Canada’s only national retail magazine continues to tackle the industry’s biggest issues as it begins developing its second volume of content.

SAJO: Transforming Traditional Project Delivery Through Holistic and Artistic Approach

Globally renowned Montreal-based design-build company SAJO marks 45 years of innovation and creativity



    • Hello Michael, this is not sponsored. It is the first of a series where we interview retail leaders in Canada. There will be more of these articles in the weeks to come.

  1. Great article. Looking forward to seeing the growth of Indochino for years to come! Drew has done an amazing job.


Please enter your comment!
Please enter your name here

- Advertisement -

Latest Stories

No posts to display

Follow us


all-time Popular