Charlie Cole

Charlie Cole, global chief e-commerce officer at Samsonite, is a keen observer who approaches leadership, new technology and corporate culture by taking time to listen and learn. Cole also practices humility, but is not one to hold back on sharing his perspective. As a result, Cole is seen as a valued leader in the market.

As part of an ongoing series of executive interviews, Tim Boerkoel, founder of global executive search and consulting firm The Brownestone Group, talks with Cole about leadership, his mentors and lessons learned on his career path.

Tim Boerkoel: Charlie, much like the digital space that you focus on, your skill set and career have grown at an impressive pace. What do you attribute to your success as an online retail expert and business leader?

Charlie Cole: Diversity in a career is often underrated — at least that has been my experience. From zero revenue/idea start-ups, private equity, agency side [to] client-side, big corporations like Samsonite — I’ve been a part of them all. That level of exposure to various ways of thinking, different challenges and diverse organizational structures and cultures has created a unique perspective that most folks don’t get. It’s a ubiquitous belief that we all learn from life experiences, and much like someone who has lived in many countries has a more complex world view, the same is true in business.

The skill set of digital is ever-evolving, but the tactical acumen needed to be successful is in some ways the easy part. Digital is such a cross-functional topic within companies that having the tactical acumen isn’t enough — you must know how to navigate an organization and push transformational efforts while maintaining the cultural values and key product focuses that drive any brand.

T.B.: What do you see as the major technological shifts that retailers must embrace in order to be future-proof? How do you equip a business to get there?

C.C.: It is shocking how little has been accomplished with artificial intelligence. It’s talked about, studied, written about; but in retail, we are still at square one in so many ways, and true adoption is few and far between. There are certain things a human just isn’t as equipped to accomplish versus a computer, and identifying those areas is step one — a scary concept for some people.

When you strip off the veneer of the exercise, the reality is you’re identifying potentially irrelevant or replaceable jobs. And to equip a business to get there, technology and automation need to be embraced and encouraged, while insulating from people’s natural fears.

One of the other limitations for AI and technology, in general, is good old-fashioned naiveté. When we don’t understand something, we push it aside — especially with the hubris that comes from years of senior management positions. For an organization to embrace technology for the absolute best interest of the company, we all must be curious and willing to change, and that curiosity must start from the absolute top.

T.B.: A lot of futurization efforts are obviously framed around Amazon. What are your thoughts on that?

C.C.: Amazon has taught the e-commerce and retail industry so much about what adopting technology can do for your business. People have raved about how Amazon recommendations are exactly what they are looking for, the ease of checkout is fantastic, the return policy is easy and the customer service is fantastic. This all came from another topic that is seemingly so obvious but was rarely seen as an outward-facing value until Amazon came along and made it gospel: customer centricity.

However, I don’t think Amazon can say they are striving to be the most customer-centric company on Earth anymore. Once Amazon made the decision to move beyond a marketplace and evolve into the third-largest advertiser on the Internet, that claim became objectively harder to make. Instead, products are now shown by whoever is the highest bidder on their growing, extremely profitable advertising platform. The grid pages are dominated by Amazon private-label brands, and other brands, particularly on the contemporary and luxury side, are rarely seen due to fears of how their brand will be represented.

All of this leads digital leaders to ask ourselves three questions: 1.) How can we use technology to make our consumer’s buying journey better than what they are expecting? 2.) What levels of customer service is the customer expecting, and how can we exceed that? 3.) How much is too much as it pertains to not violating the promises we’ve made to our customers?

Amazon wrote the playbook that we’re all trying to catch up to as retailers as it pertains to the first two questions, but they are ultimately a cautionary tale because of their failure on the third question.

T.B.: You have played a key role at a diverse set of brands, ranging from entrepreneurial businesses to very large companies. Are there some key learnings or opportunities from different types of companies that you believe are important to embrace regardless of stage?

C.C.: Yes — learn from each other. Don’t dismiss brands that have been around for a long time and are publicly traded as “old and slow,” and don’t dismiss start-up brands as “young and delusional” — both sides can learn an incredible amount from each other. I would love it if every company I ever worked at embraced the speed of the start-up with the operational wherewithal of a company that has had to make a dollar of profit. It’s shocking to me how much both sides are entrenched and scoffing at the other, when that very same arrogance is what ultimately causes failure.

You know that moment where you taught your dad how to use Uber or when you realized your mom was right all along about relationships? That metaphorical unlock is what all companies should be looking for from the other side.

T.B.: Do you have a leadership mantra that you brought to Samsonite? How does it resonate across regions and brands?

C.C.: Honestly, I think Samsonite’s leadership style has influenced mine more than the other way around. This is the biggest job I’ve ever had based on a lot of definitions: organizational size, revenue, number of brands, number of countries. And as I’ve suggested before, I preach the need to learn from each other, and so it would have been a bit hypocritical and narcissistic to assume I could or should reinvent a 110-year-old company. And to be really honest, I’ve made that mistake in past lives. It’s important to learn more about a company that you’re entering as the new person, then decide where your personal style and beliefs can add to the culture. In other words, don’t expect a paradigm shift “because I said so.”

The leadership styles that I feel I’ve added to the digital team, and are certainly part of my general management style, include: always bring data to the conversation; transparency is expected and will be reciprocated; communication is important — and asynchronous communication (Slack, e-mail, etc.) is essential for any team; accountability in the form of key product indicators always; be willing to fail and learn from mistakes; don’t guess, for in digital you can usually design a test that is far more empirical.

These weren’t new ideas to Samsonite in particular, but our digital organization has embraced these values while focusing on the larger Samsonite organization as the priority — a winning combination.

T.B.: What advice do you give to aspiring leaders? What advice do you give to peers, or even superiors?

C.C.: Learn…from each other, from your competitors, from brands that aren’t even in your space. Pay attention to what they’re doing and be willing to change. Constant learning leading to constant evolution leading to appropriate change, I think, is the only way to lead in our rapidly evolving landscape.

Also, I believe the concept of diversity in a workforce is so underrated — and perhaps misunderstood. I am a huge proponent of equality of all kinds, but I also think the key part of why it’s so important and better for a company is missed. Diversity in people means diversity in thought. The last thing a team needs is 10 people who think the exact same way.

By embracing diversity in demographic, socioeconomic, geographic and other areas, you create a team that will challenge you and generate new ideas as opposed to an echo chamber of “yes” people.

T.B.: Finally, who are your personal and professional influencers and mentors? How did they shape your approach to building and inspiring your teams?

C.C.: Another way my diverse career has positively influenced me is the people I’ve met along the way, particularly mentors. Tarang Amin, whom I worked with at Reckitt Benckiser/Schiff Nutrition and who is now the chief executive officer at E.l.f., taught me more about how to manage and build a team than anyone. Giving freedom to his peers to drive through their particular areas of expertise, as well has having very clear levels of measurement and accountability, are things I attempt to emulate.

One of my first conversations with Tarang went something like, “Look Charlie, you know nothing about CPG and I know nothing about e-commerce…let’s learn from each other.” That self-awareness, forthrightness and vulnerability is seldomly encountered, particularly when you talk about someone with the level of success Tarang has had and continues to have.

Jerome Griffith, our ceo at Tumi and now a board member at Samsonite following the acquisition, is another council I hold in high regard. A similar anecdote from Jerome focused on accountability — people owning up to mistakes and learning from them rather than preaching infallibility and dodging blame. His candor in communication can be very direct at times, but once you slow down and listen, you understand there is huge value in always knowing the truth instead of some politicized version of it.

And Kyle Gendreau, our ceo at Samsonite, may be the most thoughtful leader I’ve ever worked with. There have been so many times that I have blurted out something and immediately thought, “I probably shouldn’t have said that out loud,” but Kyle wants to hear it, even if we disagree. I hope to facilitate that level of trust and openness in every company I work for…the term “family” is overused when people talk about their corporate teams, but in our case, that frank level of discourse is certainly a very familial characteristic.