Digital 2.0 – The Modern Digital Executive Season 1 Recap



Over the last year, we met with some of the most respected and innovative senior digital executives to discuss technology, digital transformation, and innovation. These conversations turned into an ongoing series we call Digital 2.0: The Modern Executive Interview Series.

We decided to cap off a successful first season by having Prime TSR Associate Principal Matthew Schaub and Associate Principal Geremy Reiner look back on these conversations, share their own thoughts on digital transformation, and answer a few hot seat questions they didn’t expect.

Here’s what Geremy and Matt had to say.

Thoughts about bringing the Digital 2.0 Interview Series to light

When Geremy and Matt first launched Digital 2.0, they had a clear goal: to uncover the secrets of modern digital executives and their approach to innovation and digital transformation. 

And that’s exactly what they did.

Geremy was driven by his curiosity and desire to learn from these executives. He was especially interested in how they were navigating the rapidly changing landscape of the digital world in the post-pandemic era. His open-minded approach led to a really cool, inspiring, and insightful series.

“It was just an open-mindedness and a curiosity that was driving me, and it turned into a really cool inspirational series because we’re finding out that even through the struggles that some folks had in 2020, there’s continual change,” said Geremy.

On the other hand, Matt was excited to learn from and be inspired by these modern digital executives.

He saw the interview series as an opportunity to gain valuable insights and perspectives on the industry. He was eager to see how these leaders were navigating the rapidly changing landscape of the digital world and to learn from their experiences and approaches to innovation and problem-solving.

Every guest asked the same question but went in different directions

But at the same time, he was a little nervous about the interviews. He wasn’t sure why these busy executives would want to talk to him and take time out of their busy day.

“I was nervous. Like, these people, why do they want to spend time talking to me and taking time out of their busy day?” 

In the end, he was still happy that these digital executives were willing to engage in the dialogue and share their insights on digital transformation.

Has your perception of digital transformation changed through Season 1?

Matt’s perception of digital transformation underwent a major shift—thanks to the Digital 2.0 Interview Series. He realized that it’s not just about the technology but also the goals, results, and, most importantly, the people.

On the flip side, Geremy’s perception of digital transformation didn’t really change; instead, it inspired him. 

“Seeing folks out there making those big changes—then being able to sit down and spend an hour or two talking with them about their careers and the journeys they’ve taken over the last decade—is inspiring,” said Geremy.

People, processes, and technology

Geremy and Matt’s interviews with digital executives reveal a key takeaway: People and culture are the real drivers of change, not just fancy tech. 

As Epsagon CTO Ran Ribezaft puts it, “Digital transformation is driven by the people, which drive the culture, which drives processes and methods.”

But still, to Geremy, no matter how important it is to build the right culture and have the right people, technology still plays a huge part in speeding up the digital transformation process. 

“The more they standardized the processes and platforms they were building on, the easier it was to make some of those cultural shifts, enable people to ‘skill up’ on those technology platforms, or find a better way to bring products to market,” said Geremy. 

In other words, build a culture that encourages innovation and progress. Next, have the right people who are ready to embrace and drive that change. Finally, use technology to help streamline and enhance the transformation process. 

Voilà—a winning formula for digital transformation success.

How do you influence people to ride along on the journey?

Matt has a simple solution for influencing people and driving change: build consensus. 

By involving people in the process and engaging with them, you can make them feel like they are a valuable part of the digital transformation effort. 

As Matt puts it, “If you want people to be engaged, you have to give them a seat at the table to shape and influence it.”

By including people in the decision-making process and making them feel like they have a stake in the outcome, you’ll increase the odds of buy-in and success.

Empathy and compassion

“Innovation is great, but having empathy and compassion is the most important thing” – Sameera Rao, Chief Technology Officer at Greenlight. 

This is Geremy’s favorite quote from the Digital 2.0 Interview Series because he can relate to what Sameera said. According to him, empathy and compassion are critical in everything they do, especially when it comes to digital transformation. 

When an organization starts a digital transformation journey, we sometimes forget it’s hard. And having empathy and compassion toward those who may be struggling with changes can make a big difference. 

By showing understanding and care, organizations can create a more supportive and inclusive environment that helps everyone succeed.

Creating a media that connects: How did it boost brand awareness?

Geremy and Matt’s Digital 2.0 Interview Series was a massive hit, and it’s no surprise why. With over 18,000 unique views and 22,000 impressions, this series was the talk of the town. 

According to Geremy, this happens when you get unique voices from people that impact and change things at different organizations and combine that with social media; it’ll spread quickly.

But the real cherry on top? The series wasn’t just a hit with their usual crowd—people and organizations they didn’t even know engaged and watched the interview series. 

As Geremy put it, “The fact that it actually went outside of our sphere, and it started percolating out through other areas, and we started getting engagement from folks that we haven’t traditionally talked to—even other organizations and other change agents are starting to look at this stuff. That was the cool part.” 

And by the end of the season, the series was a hit, and Prime TSR’s brand awareness was through the roof.

What have you learned about the importance of taking a step outside of the norm of the traditional tech way to show awareness and connectivity?

According to Geremy, when they launched the Digital 2.0 Interview Series, people started to see its value. 

And by launching something like this, they were able to let people see their efforts, ideas, and the value they can bring. Not only that, the interview series allowed other executives and organizations to showcase their opinions and make an impact.

“Other people see the importance of it, it’s probably more important than even I suppose,” said Geremy.

Post-pandemic era: What’s next for the tech industry?

As we emerge from the pandemic, we are interested in understanding how technology may continue to shape our lives and workplaces. To gain insights on this topic, we asked Matt and Geremy for their thoughts.

Matt believes that technology will experience a period of slowing down or “mellowing out” in the post-pandemic era. He cites the current economic challenges as a contributing factor to this trend.

Geremy, on the other hand, believes that the impact of technology on different industries will vary. He suggests that some industries have been able to use the pandemic as an opportunity to innovate and become more resilient, while others may be more affected by economic downturns.

Digital 2.0 Hot Seat: Real, Hype, or WTF?

And now, for the grand finale of our chat, hot topics that always get Matt and Geremy’s guests talking: the metaverse, crypto, AI, remote work, and Elon Musk. 

Time for Matt and Geremy to weigh in with their thoughts: Are they real, hype, or WTF?


Matt: “It’s real. We gotta figure it out, though. It’s not just something you drop in. There’s a lot more energy that needs to be put into everything in front of it and everything behind it, but it’s real.”

Geremy: “It is hype right now. Don’t get me wrong. I love AI. I love the concept of it. And we do have more intelligent systems. The concept of AI, though, is independent, and that’s what we should always be guarding against.”



Matt: “WTF. I don’t get it.”

Geremy: “I love the idea of a metaverse. The problem is the WTF comes up.”

“I think AI is gonna have to happen before we even get into a conversation where something like the idea behind the metaverse actually happens.”



Geremy: “For me, it’s still real. Don’t get me wrong. I think the idea of blockchain development is still a great distributed way to manage things. Crypto as a currency, on the other hand: WTF.”



Matt: “Remote work is real. I think it’s made us better. I think we’re better humans as a result of it.”

Geremy: “Let’s make that real. Let’s give the flexibility where it needs to be as well.”



Matt: “Real. I love him. I think he’s great. I get a kick out of him. I enjoy him from an entertainment perspective. He’s an innovator. He’s doing things differently. Whether you like what he’s doing or not, he’s doing things differently.”

Geremy: “Elon is a ton of hype, but that is his personality. I wish he would focus more on the innovation portions of his world and on the motivation of his employees.”

Thank you for the fantastic conversation, Geremy and Matt!

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