TransformIT Show
The New Age of the Digital Leader

Charlie Cole

CEO
TheLine

Could a marketing guy really represent the future of digital leadership? I remember the day that I met Charlie Cole. We were both at an executive networking event and just happened to cross paths.

We had absolutely nothing in common. He was running digital marketing for Lucky Brand Jeans. I was running an IT consulting firm. But for some reason, we hit it off. There was something that told us we shared some common values. I don’t know, maybe I just liked him. But in either case, we’ve stayed in touch over the years and I’ve followed his career with both great interest and fascination as he rapidly transformed himself.

That’s why it was so exciting for me to be able to travel to New York a few weeks ago to interview him for the Transform IT Show.

The Fusion of Business and Technology

I was there to tell the story of his rise from “marketing guy” (as he was when I met him) to high tech CEO of a new startup called The Line. And I think that his story is really the story of our future because he represents what I believe the modern digital leader will look like.

I believe that modern digital leaders are going to be part IT, part business, and it won’t matter which side of the house you started on. As the lines between business and technology blur, we’re going to need to embrace both sides of the equation if we want to get the job done.

As we talked, Charlie shared some great insights with us. The days of IT as an order-taker are over. The divide between the CIO and the CMO is a myth. We need to instead come to solve problems together. These were all truths that were exemplified by Charlie’s own journey.

Understanding Your Role as a Digital Leader

If you’re an IT professional, I think Charlie demonstrated to us what the modern business leader is going to look like: someone who understands technology intrinsically. You’re going to have to speak his language if you hope to survive, because he is embracing technology in all of its forms in his quest to change the game for his company.

And if you’re a business professional, this is what your future will look like. You can’t abdicate your responsibility to understand the intricacies of how technology will impact every facet of your business. The only way for us to thrive will be to do it together. And we can’t do that unless each of us becomes intimately familiar with the whole package.

But perhaps it was his last bit of advice that really told us how to do that.

He challenged us to embrace our own awesomeness and to accept our weaknesses. To spend more of our energy focused on improving our strengths and less on improving what we aren’t good at. It is advice that has the power to change everything about how you approach your career and your life. Those two challenges may seem at odds with one another. Embrace the other side of the equation, but also accept your weaknesses and your strengths. But if you think about it, it’s really a recipe for the balance and humility that we will each need to come to the table open, informed, and comfortable with our own role. And I think that it will be one of the keys to finding your own pathway to success as you strive to become a digital leader.

About The TransformIT Show

Each episode explores the questions:

What does the future hold for IT organizations?
And what will that mean for their future leaders?

Host Charles Araujo interviews business executives, IT leaders, futurists and industry experts to understand how their career and experiences shed light on what the future holds for business and the IT organizations that power them. Most importantly, our guests share their advice for all future leaders about how to survive and thrive in the Digital Era.