It seems every organization is chasing digital transformation. Some companies are succeeding, while some are wallowing a bit, trying to figure out how to do it. Box is a company that is both successfully navigating digital transformation and being a catalyst for digital transformation at other organizations.

In this DevOps Chat we speak with Paul Chapman, CIO of Box, about digital transformation for both Box and other companies, and he gives us his own take on what the environment is like for companies and what they should do to thrive today. Great conversation, enjoy!

As usual, the streaming audio is immediately below, followed by the transcript of our conversation.

Transcript

Alan Shimel: Hey, everyone. It’s Alan Shimel and you’re listening to another DevOps Chat. I’m really happy to have as a guest on today’s DevOps Chat, Mr. Paul Chapman, CIO at Box. Paul, welcome to DevOps Chat.

Paul Chapman: Thanks. Great to be here, Alan.

Shimel: Great to have you here. So Paul, before we jump into a couple of the items we wanted to talk about. I guess in case anyone in our audience maybe is not familiar with Box or yourself, why don’t you just quickly level set your background, Box, and we’ll jump in from there.

Chapman: Sure. Well, maybe I’ll start with just a little background, accelerated bio of sorts. Been in the technology space for quite some time now. I like to joke that although this is the truth, I was a COBALT programmer and an RPG programmer back in the late ’80s. So I’ll fast forward to today and say a lot has gone on in between. I’ve had to reinvent myself many times over to stay relevant. I often tell my team that the pain of change is mandatory. It’s the suffering that’s optional.

So get comfortable with being uncomfortable if you’re in the technology space. It’s never boring. That’s for sure. I’ve done a lot of things in between but thoroughly enjoying my time over here at Box. We’re born in the cloud, grown up digital company. Very forward thinking, innovative. And we’re helping tens of thousands of organizations around the world to help to transform and digitize the workplace.

Shimel: Fantastic. So Paul, you mentioned Box and we talk about unicorns and cloud natives and these kinds of things. Box is certainly a member of the club. And while they themselves, generally, these kinds of companies like box eat their own dog food in terms of what they preach and everything, we almost take for granted the transformative wave that they’ve ushered in. Again, I’m your age or maybe more. I remember the 1984 commercial with the hammer –

[Crosstalk]

Chapman: Mm-hmm. The Apple one, the famous Apple one.

Shimel: The Apple commercial. Sure. The Mac commercial. So in a lot of ways, companies like Box and as their poster child for it have broken through the silos that in the IT world, you and I grew up and kinda held us bound. If you can, give our audience a little bit of – I don’t know if that was intentional that it breaks down silos or it was an unintended consequence but talk to us about how is it helping to break down. How does it usher in what – digital transformation is something everyone talks about. How does it help with that?

Chapman: Yeah. Well, I think when you look at – and I’m gonna sort of just geek out a little bit and share that one of the things that I have – now, we’re starting to see some maturity in what I would call sort of the modern reference architecture for how you run your IT service today or business services today, is that when you look back at sort of the technology that we invested in in the ’90s and in the ’80s, which at the time, was the most modern advanced technology I should say, at the time. Unfortunately, it was architected in such a way that it was very siloed and you ended up sort of building up these sort of monolithic sort of application stacks where you went to sort of the oracles for everything or the SAPs for everything and it was very hard to integrate.

And unfortunately, what happened is is you sacrificed a lot of what I would call best of breed capability and innovation in that model and because that architecture doesn’t, in a sort of step wise, linear way evolve to support today’s way of working – today, we have a new style of employee. One that has grown up digital that’s been educated by consumer experiences that expects a certain set of things when they enter the workplace. You have a new style of workplace. It’s very open and social and collaborative.

You have this new style of IT that’s evolved to support that. And when you look at what’s actually happening, the modern architecture is built around this best of breed ecosystem and there’s innovation going on everywhere. But the innovation is generally organizations are picking the area that they’re gonna be the most innovative in and they maniacally focus on the innovation in that space. So they’re the best at what they do and Box is absolutely the best at managing unstructured content for the enterprise with the best compliance and regulatory and so on. And security and risk and all those things.

And then there are other companies that are the best at messaging and then there are others that are the best at certain types of collaboration. And what we get to do now is to start to bring all these services together because they’re built to interoperate which the architectures of yesteryear weren’t and we get to bring and curate that into the experiences we bring to our employers, partners, suppliers, and customers and therefore, we’re starting to create more automation, more digitization across this best of breed ecosystem. Long winded answer but there’s a lot going on in there today.

Shimel: Oh, absolutely. So let’s pick into a couple of those areas. Number one is lock-in or the – we used to suffer with these large stacks. You were locked in though. Right? I was talking to someone earlier today, a start up who managed Macs for enterprises. Right? And why haven’t we seen that before? Well, maybe there were enough Macs. But we’ve all suffered from lock in in our technologies.

Chapman: Yeah. And we don’t like it. We don’t like the way it makes us feel. We don’t like to feel captive or without choice and really today, freedom of choice is extremely important. And so what I do know, though, and this is something that I’ve certainly come to appreciate is especially if you are, as you think about a much more heavily cloud based footprint, you have the freedom from infrastructure. You have the freedom from direct sort of operational responsibilities that in our past lives, we have significant operational responsibilities managing a lot of technology debt and infrastructure and so on and we had to manage service levels, capacity, performance, backups, failover, all the things that are just really keeping the lights on.

We’re not adding any material value necessarily directly to the businesses. It’s the things, the services that run on top. And so what I’ve seen is is that now as you start to move to a cloud based model which is much more subscription based. The on ramps are a little smaller. The off ramps are a little smaller. The ability to change out services for services that may not be as innovating as fast as others as is a little easier but I think the key thing is this. Every one of those services that you subscribe to, it’s a mutually beneficial outcome. They have to earn your business on an ongoing basis.

Shimel: Yep. On a minute by minute. Not even daily.

Chapman: Because if not, the subscription stops and you move it somewhere else and if they are not maniacally focused on innovating in their space, having highly reliable, scalable services, having services that meet your compliance and regulatory requirements and having services that meet your trust and risk criteria for that particular service, they don’t have a business. And so the beauty of this model or this new emerging model, I should say, is that in the old ways, they’d sell you software and then you sort of … you get locked in and it’s hard to move. Now, we think about it as all the time. It’s about the customer all the time. How are we making our customers get more value from their investment in us and how can we make sure we’re providing reliable services and innovative capabilities that they’re subscribing to to maintain them as a customer. And that’s good for us.

Shimel: Absolutely. So I would even go further, Paul. I’d say the hardware vendors locked you in more than the software guys even did. Right? When you made decisions, whether you were on Solaris or this flavor of Unix or Microsoft or what have you or HP, I mean, HP, and I know you used to be at HP, no disrespect to them, but they were really good at talking about freedom and best of breed while locking you in tighter than a drum. But today, so to me, this all refers to something that I call portability. We have, as consumers, as customers, we have such portability today where we can take our stuff up and go. It’ll run anywhere we want, just about.

Chapman: That’s a great point. Actually, a really good point. And the infrastructure, I was focusing on the services piece but you’re absolutely right. As I mentioned, the freedom from infrastructure in the cloud world is like no offense to the infrastructure providers. It’s just I add more value to my organization when I’m not focused on those things. It’s a give back of time and one of the most precious things we can give anybody is time. And I’m able to use that time to do what I would consider much higher value, contribute at a much higher value to the organization because of that.

Shimel: Absolutely. Paul, I wanna transition to another topic that we spoke of but I think you gave me a great segue here and that is that when we talk about things like transformation and thriving and leveraging what we have, what the technology world has to offer us today, so much of it, frankly, isn’t hardware or even software. The success or failure of organizations is often based on their culture and their people. Right? And some, we live in a gee whiz world where we take things, we were talking off hand about answering the doorbell from China, but organizations can’t really thrive, compete, and transform without that cultural sort of happening. Curious on your thoughts on that.

Chapman: Yeah. Probably … at Box, we talk a lot about the future of work and also, we talk a lot about it’s not about rewriting your software. It’s about rewriting your company. And when we look at companies that … if you look at just some of the statistics, 52 percent of the Fortune 500 have disappeared since the year 2000. And if you do the math, that’s more than one per month. And a lot of people get into this techno-panic thinking it’s technology that’s disrupting these companies but the reality of it is is technology is enabling that disruption but the technology that’s doing this is available to everybody including the incumbents that have built their business models and their operating models on sort of a sort of legacy way of working. And you have – if you look at the companies that are disrupting, it’s because they have a different operating model. They have different business models.

They operate culturally very different and the cultural shifts are really, really hard, especially in organizations that have become very established in their markets because that’s what got them there. And the reality of it is we used to coin this term sort of this frozen middle part of an organization that didn’t necessarily have – doesn’t necessarily have aligned incentives to change. Because it’s like what’s in it for me on the other side of this change? And they say at any given point, a third of an organization, and this changes, varies from company to company but a third or an organization knows where you’re going and how you’re gonna get there. A third doesn’t but they’re willing to learn and invest and figure it out and a third doesn’t, never will, isn’t interesting, da, da, da, da. And that’s resistance.

And the resistance to change has to be resolved. A lot of companies will figure out maybe what they need to do and even why they need to do it but it’s the execution of the how and sometimes, that how is where it really holds people back because they realize that they may not be able to get there with the culture and the people they have. And they switch out leaders and so on and I can share some more in what I’m seeing companies that are able to do this successfully. Most of them, it does take sort of what I would call sort of breaking the company somewhat in order to ______ them.

Shimel: No, no, no. You gotta burn it down. Right? And I don’t wanna burn it down. But there has to be fundamental change. Last question because I know we’re running low on time but how important is leadership? Right? As a CIO, this is kinda your … this is a big part of your role, right? But how important is leadership in making that transformation?

Chapman: It’s absolutely key. You can’t do it without the right leadership mindsets and call it coalesced support. So I’ll give you a recent example that I was talking to a CIO of a very, very large company that had been struggling with, call it, reinventing itself and reestablishing itself in a new modern digital world and was starting to make some, is starting to make some success there. And one of the questions that we often get asked as CIOs is, “What’s your partnership model look like or your engagement model look like with the business and how do you think about change management?” And like I said, I went to school to learn how to do programming and COBALT and RPG. I never went and got a PhD in change management.

[Crosstalk]

Yeah. I’m not an expert at trying to change the mindsets of thousands of people across an organization when at least a third of them, based on our numbers, don’t even want to. Right? I’m jesting a little bit. The CIO is one of the best partners to enable change but isn’t necessarily always in the best position to drive that change across the organization. You have to have leadership alignment and so on and the company I was talking to, I was talking to the CIO and he was asked that question. “What’s your – people are interested because they’re starting to see meaningful change.”

And they asked him about his relationship model with the business and he said, “Here’s what happened. When we got our new CEO, he went to all of the heads of all the different business functions that we have and said, ‘If we are going to transform, if we are going to think like a digital company, if we’re gonna think like a technology company and we’re gonna disrupt, it’s incumbent upon every single one of you business leaders not for IT to come to you and say, ‘Here’s what our model for working with you is.’ It’s what is your model for working with IT? What is your model for working with the CIO?’”

And he said that once that accountability came into the business owners, he said it just greased the runway for the CIO and organization to enable accelerated change across the organization because it wasn’t incumbent upon the CIO then to drive that change. It was to enable the change. And I actually think that that’s something that is key here is we have to rethink the model of how we engage and operate, not just it’s a technology solve.

Shimel: Right. I agree with you. First of all, I wanna apologize for taking up much more time than I think we booked but it was a great conversation. It was kind of fascinating. Maybe we can have you on on another chat at some point or through the other vehicles we use. But look, continued success with Box. We’re customers.

[Crosstalk]

devopsy.kinsta.cloud only for our most important data. But anyway, thanks for being our guest on DevOps Chat today and we’ll speak to you soon.

Chapman: Appreciate it. It’s fun hanging out.

Shimel: All righty. This is Alan Shimel for devopsy.kinsta.cloud. Thanks for listening. This is another DevOps Chat. See you soon everyone. Take care.

— Alan Shimel