In this special compilation episode of Innovation and the Digital Enterprise, Patrick Emmons highlights key insights on digital transformation from top tech leaders. Featuring perspectives from Andrei Girenkov, Christopher Paquette, Ann Yeung, Sandee Kastrul, Deepak Kaimal, Jeff Miller, Christina Garcia, Tanya Hannah, Dan Kirsche, Dom Scandinaro, Subramanian Kunchithapatham, and Gene Kim. The episode delves into leading transformative tech teams, balancing disruption and protection, the role of AI, the need to stay nimble, and the foundational significance of human connection and communication in achieving successful digital transformation.

• (00:00) Welcome to Innovation and the Digital Enterprise
• (02:17) Andrei Girenkov Understanding the Scope of Digital Transformation
• (03:17) Christopher Paquette on Balancing Protection and Disruption
• (04:00) Ann Yeung on The Role of Corporate Functions
• (04:52) Sandee Kastrul on Diversity and Innovation
• (05:22) Deepak Kaimal Leveraging Gen AI for Business Solutions
• (07:01) Jeff Miller on  Navigating Technological Change
• (07:21) Christina Garcia on Empowering Teams
• (07:59) Tanya Hannah on Keeping Nimble
• (08:28) Dan Kirsche on Org Structure and Accountability
• (09:17) Dom Scandinaro on Growth, and Agility
• (10:10) Subramanian Kunchithapatham on the Challenges of Digitization
• (10:53) Gene Kim on Connecting People Through Norms, Rituals, and Processes

Andrei Girenkov is Chief Technology Officer at CSC Service Works. Christopher Paquette is Chief Transformation Officer at Personify Health. Ann Yeung is VP of Engineering at GEICO. Sandee Kastrul is President and co-founder of i.c.stars. Deepak Kaimal is Chief Technology Officer at COMPLY. Jeff Miller is Chief Product Officer at Coates Group. Christina Garcia is SVP of Engineering at Echo Global Logistics. Tanya Hannah is Chief Information Officer at OneTen. Dan Kirsche is Chief Technology Officer at Chamberlain Group. Dom Scandinaro is Chief Technology Officer at Cameo. Subramanian Kunchithapatham is Vice President - BI Solutions at Morgan Stanley. Gene Kim is an author, researcher, and founder of Tripwire, Inc.

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Podcast episode production by Dante32.

Patrick Emmons:

Welcome back to Innovation and the Digital Enterprise, the podcast where we explore what it takes to build and lead transformative tech teams. I'm your host, Patrick Emmonds. Today we're doing something a little different. A special compilation episode focused on one of the most recurring and thought provoking themes across our interviews: digital transformation.

We've pulled together insights from some of our most impactful guests, each offering a unique take on how real change happens in organizations. You'll hear from people like Andrei Girenkov on why transformation has to include people in the process. Christopher Paquette on balancing disruption with protection. Ann Yeung will be talking about why attention to internal operations is essential, and my good friend Sandee Kastrul reminds us that innovative change comes from bold, unconventional thinking. Then we will hear from Deepak Kaimal on how gen AI can be a powerful transformation tool. Jeff Miller is going to share his thoughts on the underrated skill of listening, the foundation, in my opinion, of good leadership.

Then Christina Garcia on the importance of empowering your team to lead change from within. Tanya Hannah is going to talk about staying nimble. Dan Kirsche shares the challenges and opportunities within an actual org structure. Dom Scandinaro discusses how the size of your team changes the shape of transformation. Subramanian Kunchithapatham points out that technology often moves faster than training and why you can't afford to leave your team behind. And wrapping it up, Gene Kim is going to share his thoughts on the powerful reminder that communication, human connection, the human touch, is the foundation of true transformation. It's going to be a great little journey. I'm glad you're joining us. Let's dive in.

Andrei Girenkov:

A lot of what we do is sometimes called digital transformation, and it's often led by technology executives. But if you look at what's actually involved in the success of digital transformation, it's changing people's job descriptions. It's changing operating models, it's changing revenue models. It's a lot of enterprise change management for getting people to behave in a very different way, and it's all empowered by a technology that's a necessary block, but it's not an efficient block.

It's only, you know, maybe 50% of the work, maybe even less. So the more you can pick yourself up from your technology chair and kind of get out there into the maybe a little bit uncomfortable business zone, the better position you will be to speak effectively to your business leaders, lead change to achieve digital transformation, and do that in a way that hopefully goes out beyond your blinders and into the broader industry network around you.

Christopher Paquette:

I always go back to the why behind it. Asking why would we digitally transform, leads you to what is digital transformation? And I think the why I always talk about, has two parts. One is protecting the core of what the business is and how you create value and then disrupting; disrupting the ecosystem, creating new products, creating new services, new revenue models, new routes to market. And between those two, protect and disrupt, you really kind of have the waterfront covered for value creation. So it's about protecting and disrupting to create value for customers.

Ann Yeung:

When companies are going through a lot of transformation, the corporate functions are actually hit the hardest because there is a lot of people and process changes that need to happen. And the underlying tech that needs to enable it goes through a big change and being the backbone of any company, these corporate functions going through a digital transformation are extremely important in order to enable the success of other functions. So I feel like sometimes you don't feel like it's as sexy because corporate functions don't drive revenue, right? because they're not revenue producing. But then if not done right, the efficiency of the company and how we can operate gets impacted, especially during digital transformation and change.

Sandee Kastrul:

I really believe that diversity is the primary driver of invention, and all the greatest innovations are coming from people who are thinking or looking at things differently. We know that the next big idea is coming from someone who's not thinking about today's or yesterday's way of doing things or thinking about how to disrupt things, how to make things better, how to reinvent, how to challenge what's wrong.

Deepak Kaimal:

So to be able to map that back to businesses, it is not so much about saying, okay, where can I use gen AI in my business? Which is the wrong question to ask. The question to ask is, what is a problem in my business that I couldn't solve before? And the solution doesn't have to be gen AI, but in many cases there are unsolvable problems like data cleansing, data mapping, stuff like that, where you now can do it extremely reliably and extremely rapidly, and at the level of quality is just amazing. So I've seen a lot of organizations that will hire people or label on their technical skill like any label, right? “I’ve got 15 years experience in Java, or I've got 20 years experience in dot net.”

But what I've seen, in my experience over the last 25 years, is that the ones who are successful are the ones who are able to navigate that change. It is important to be strong in that technology, but it is also important to know that it doesn't stay static. It is people who are able to navigate that change shift from one platform to the other, have the curiosity to understand how the new platforms are being developed, and to be able to take it on and build on top of it.

What you need are people who understand the business, who understand how technology works, and to be able to explore and map how these technologies can be leveraged to drive your own business to navigate change. Sometimes to ride the wave, almost look for those opportunities where change is driving growth.

Jeff Miller:

Sometimes it's just good to listen and understand, right? And I think as a good life lesson as you go through, it's just like you got good ideas, but really understanding the local context is really important and really to kind of help shape and understand how you actually drive change through the organization.

Christina Garcia:

You control what you control. And if new information comes in, we adapt, we adjust, right? And we change scope, we change our plan, we make alternatives, we adjust the plan. So I think the biggest thing for me right now is helping the engineers feel truly empowered to take control of what they can control.

We can set a date based on what we know and what is in our control. And when new information comes up or a situation changes, like we adjust, we have new information and we make better decisions. I think it was Maya Angelou that said that you make the best decision you have with the information you have. When you learn more, you do better.

Tanya Hannah:

That's where innovation, transformation and growth really occurs, and what we're seeing today, you have to be nimble. Our organizations need agility, scalability, and the only way you can do it is if you can really anticipate what's going to happen. Make sure that your teams and your organizations are there and the technology is behind it.

Dan Kirsche:

For me, it always ties back to org structure. So I focus on that first. And I have, throughout my career, I've kind of fine tuned it. It's not very different, I think, than most other companies, what they implement. You know, other tech companies kind of follow this practice as well. It's really standard agile.

I think that there's some really key principles that are necessary, and the reason why I focus so much on this is the need to drive ownership. Ownership and accountability is like first principle. You have to have that, to do anything else and drive any other sort of change within the organization, whether it be architecture, like other collaborative efforts, that sort of thing. You have to have accountability, ownership, especially in super complex projects.

Dom Scandinaro:

I think one thing that you just have to learn firsthand, which seems really obvious in retrospect, is just that the same processes and procedures that you have for one team of engineers with a team of three engineers at the whole company, won't work when you have ten teams of engineers with a hundred engineers at the whole company.

It isn't immediately obvious when you're in the thick of it, that if things are going super well and you're hiring and hiring and building more and more teams, that you actually need to change anything, right? Because things are going well, people are deploying code, more customers are coming, revenues increasing. You don't always just take a step back and think about what efficiencies are we missing out on by not adjusting our processes or, you know, kind of the opposite: what problems are we causing by maybe moving too fast?

Subramanian Kunchithapatham:

It is not easy to digitize all these things, digitizing assets, processes, and interactions. Technologically you need to move fast and digitize this thing. That's one challenge. The second challenge, I would put it as you need to do it at a much faster pace. And when you have to do it at a much faster pace than all the existing processes and your associates and your employees are trained on the existing processes. Once you're digitized, there are going to be changes. Then you need to train all your associates to be familiar with how, what is the new mode of operations.

Gene Kim:

The difference maker is really in this kind of layer three wiring, right? So layer one is the object in front of us. It could be the patient, it could be the code, it could be the binary running and production. Layer two is the tools and technology. So that could be the MRI machine, the cat scanner, the IDE that we're editing our code in. It could be the Kubernetes platform.

But the difference maker all in layer three is, how do we connect our teams and people together, norms, rituals, processes, the software architecture we work within that dictate. Who talks to who about what and when and how. Right? And on the one extreme, everyone has what they need when they need it in the right format, and they can get it easily.

In the worst case, no one has what they need, right? And so even small efforts require superhero effort, massive coordination, costs, escalations, cajoling, politicking, right? Even to get small things done, right? And everyone's stuck. And so I just found that kind of really dividing what the spectrum performance looks like and isolating it to layer three organizational wiring just to be so illuminating. It was by far the most intellectually challenging thing I've ever worked on, but it's one of the most rewarding.

And one more thing I think whenever you study transformations, when an organization goes from good to great, whether that's in DevOps or Agile or like the new me joint venture in Fremont, California, what almost always happens is that layer one and layer two nothing changes. Same people, same equipment, same floor space, right? Same capital equipment. The only thing that changes is layer three, right? And so, you know, when we say it's the difference maker, it just really says that leaders are truly responsible for that layer three wiring. That preordain how to what extent people can do what they need to do easily and well.