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Welcome To Digital 2.0:
The Modern Digital Executive Interview Series.
Episode 4 / July 6, 2022
Digital 2.0 Episode 4: Alex Chimon, Digital Technology Leader
In this episode, Alex Chimon, A Digital Technology Leader talks about how companies in existence has digitized and evolving with mixed success.
Digital 2.0 is an interview series dedicated to interviewing the best and brightest senior digital executives around the world that have taken a stance on the importance of Digital within their organizations and are helping everyone understand the role of technology in our everyday lives.
Episode 4 / July 6, 2022
People, Stories, and Integrity: Why They Matter More Than Technology

“Digital transformation” is a catchy phrase. But that doesn’t mean Alex Chimon, a Digital and Technology Leader, has to use it—or like it.

In April, he dashed off a brilliant, 2,500-word missive that explains why. To Alex, using the phrase “digital transformation” is a little like speaking Latin: a dead language from an era that, digitally speaking, might as well have come from the Roman empire.

Companies technologically transformed decades ago. Those that didn’t are fossilized in our memories or long forgotten. Any company that exists in the current market has already transformed. Now, they must evolve—that is, step beyond where they’ve been and into uncharted territory.

But that doesn’t get at the heart of why Alex rejects the phrase. It’s also because companies are preoccupied with “digital transformation,” yet they lack an established purpose.

Alex calls it “technology for technology’s sake.” He means that you can have all the technology in the world, but without vision, leadership, cohesion, and people, you’re chasing specters—and then using the language of antiquities to describe them.

After reading Alex’s article, I wanted to continue the conversation he started. During our 30-minute sit-down, we covered a lot of territory.

Everything from digital evolution and why you should keep an eye on Home Depot and Stitch Fix to what vision means to him and why data will determine who’s around in a decade.

Here’s what Alex had to say.


Before I jump in, I’d like to give Alex a proper introduction.

Alex is a strategic business leader and technologist with 25 years of industry experience. He’s an experienced coach and consultant who has driven revenue, reduced operational costs, and bolstered customer experiences for a slew of organizations.

These include Blue Cross and Blue Shield of Illinois, Montana, New Mexico, Oklahoma, and Texas; Chicago-based start-up Pyroweb; Catalina USA; McDonald’s; HP; and others.

He holds an MBA in international business and operations, an MS in E-Commerce, and a BS in computer science from DePaul University.

Biggest Lessons Learned About Transforming Companies Digitally

“Digital transformation is evolution.” When I asked Alex what he’s learned in nearly three decades of helping companies digitally transform, that was the first thing he said.

The word “transformation” might have been applicable 20 years ago when print companies turned off the presses and went digital. But that’s not what’s happening anymore.

Any company in existence has digitized. Now they’re trying to evolve with mixed success. For some, evolutionary growth becomes stunted because the organization lacks a clear and cohesive purpose.

Organizations shouldn’t ask, “How am I building technology?” says Alex. Instead, they need to figure out why they need to change their business. That means assessing customer engagement, gathering data, and making strategic decisions based on it.

Just as important, it means setting goals and aligning strategy across the organization. If organizations need technology to accomplish their goals, that’s fine with Alex. The trouble is that organizations are building technology without knowing if they need it.

First, “you need to make sure you have a clear message: this is where we’re trying to go; this is why we need to get there; this is how we’re going to do it,” says Alex. Without that, failure is inevitable.

“I’ve seen it happen where leadership declares it’s time to ‘go digital.’ Everyone below is, like, ‘aren’t we already digital?’” It’s up to leadership to clarify what “going digital” means.

Otherwise, you’re going to create a mess of confusion.

What Do Innovation, Transformation, and Modernization Mean to You?

After reading Alex’s article, I figured I knew where Alex stood on organizational innovation, transformation, and modernization, but I asked anyway. I’m glad I did because his answer was insightful.

To innovate, transform, and modernize might mean building new technology. But organizations who get it right don’t abandon what’s right in front of them.

“Innovation isn’t about reinventing the wheel,” says Alex. “Take Uber, for example. They didn’t build new technology; they didn’t have to.” Instead, they simply grabbed onto existing technology and used it in a new way.

That technology might not have been new and flashy, but it was good enough to help Uber chart a net worth of $45.85B in May.

For Alex, being innovative is a two-part exercise. The first is taking the tools you already have and maximizing their efficiency. “If you’ve exhausted the limits of that technology,” says Alex, well, “perhaps it’s time to build something new.” Until then, use what you have.

That’s innovative.

To further illustrate, Alex uses a few examples—mRNA vaccines being one of them. mRNA vaccines have been around for decades, yet before COVID, most people had never heard of them.

The vaccines are fascinating because they teach cells how to make proteins that trigger an immune response inside the human body. When the pandemic hit, researchers speculated that this decades-old technology might potentially work on COVID-19.

So they started testing. And sure enough, it worked.

Alex’s point is that mRNA researchers didn’t start from scratch or build something new. Instead, they looked at what they already had, tested it, refined it, and put it into play. There’s a good lesson there.

Biggest Impact on Digital Innovation for the Next 10 Years

Are your customers engaged? And do you have the data to prove it? For Alex, the answers to those questions may determine who’s around and making the biggest impact in the next 10 years.

To engage customers, you have to get the data right and then use it to personalize your customers’ user experience. Amazon is the most obvious example of a company that uses data to custom-tailor the customer journey.

Doing that is harder for smaller organizations focused on a single niche. Harder, but certainly not impossible. I asked Alex to give me a few examples of smaller companies he’s keeping an eye on. Home Depot was one. Stitch Fix was another.

“I’m a big DIY guy, so I spend a fair amount of time at Home Depot. My wife will confirm that by showing you my growing collection of tools.” But Alex follows the company for another reason: their end-to-end engagement is impeccable.

Companies That Are Surprising

Everything from online browsing and in-store shopping to returning items is streamlined. The company knows what users want because they track browsing habits. They also track purchases, so customers never need a receipt to return an item. As a result, the buyer experience is seamless and fully customized. That’s attractive.

Alex also follows Stitch Fix—partially because he admires their customer-engagement strategy, partly because he has no other choice.

“They have my wife figured out to a tee,” he says. “Stitch Fix tracks her browsing habits, purchases, and feedback.” Based on that, they know what kind of clothes she likes.

“If you need proof that the company knows what it’s doing, come on over and look in our closet. I think organizations can learn a thing or two from this company.”

Digital 2.0 Hot Seat: Real, Hype, or WTF

I closed our conversation with a series of rapid-fire questions covering four of my favorite topics: AI, the Metaverse, crypto, Elon Musk, and remote/hybrid work.

Are they real, hype—or do they just make you scratch your head and say, “WTF?” Here’s what Alex had to say:


“Pay attention to AI. It’s going to drive our customer engagement strategies going forward.”

The Metaverse:

“Great opportunity there, but shortsighted in its current form. I want to say the Metaverse is real, but I’m still saying, ‘WTF?’”


“There’s huge opportunity with crypto, but it’s completely useless until it’s backed monetarily. No one will trust it otherwise.”

Elon Musk:

“Controversial, but obviously brilliant. Whether it be with Twitter, electric vehicles, or space, he sees the bigger picture—and people are still catching up.”

Remote and hybrid work:

“We need it. And if companies reject it, they’re limiting themselves, especially in terms of talent acquisition. There are a lot of brilliant people out there, and remote allows you to tap into that intelligence.”

Thank you, Alex, for such an insightful interview!

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