ESI Interviews

Ep 25: How AI Fuels the Future of Work with Cisco VP of Business Strategy Paul Chapman

Guest Michael Keithley
Paul Chapman
June 28, 2023
Listen to this episode on your favorite platform
Apple Podcast Icon - Radio Webflow TemplateSpotify Icon- Radio Webflow TemplateGoogle Podcast Icon - Radio Webflow TemplateApple Podcast Icon - Radio Webflow TemplateApple Podcast Icon - Radio Webflow Template
Ep 25: How AI Fuels the Future of Work with Cisco VP of Business Strategy Paul Chapman
ESI Interviews
June 28, 2023

Ep 25: How AI Fuels the Future of Work with Cisco VP of Business Strategy Paul Chapman

On the 25th episode of Enterprise Software Innovators, Paul Chapman, VP of Business Strategy at Cisco, joins the show to discuss his perspective on AI, how technology will transform the future of work, and hard-fought lessons on innovation that have stuck with him throughout his career.

On the 25th episode of Enterprise Software Innovators, hosts Evan Reiser (Abnormal Security) and Saam Motamedi (Greylock Partners) talk with Paul Chapman, VP of Business Strategy at Cisco. Cisco is a leading global networking equipment, software, and services provider. In this conversation, Paul shares his perspective on AI, how technology will transform the future of work, and hard-fought lessons on innovation that have stuck with him throughout his career.

Quick hits from Paul:

On productivity tools granting back time: “You know what a billionaire can't buy? One second of time. If we can give people back the gift of time through this shift to hyper-productivity, I think we're gonna see a huge fundamental paradigm shift in how we operate.”

On the future of office buildings: “I spend a lot of time talking to customers about the digitalization of real estate, smart buildings, and smart building technology. The amount of sensors and intelligence we can now get from buildings in terms of how they're being used, helps us make smart decisions around how we think about sustainability.”

On the expectations of CIOs: “CIOs are expected to be disruptive and failure is the currency of risk. I think all too often the CIO behaves in a very conservative way, but that's not how they're measured and what's expected of them. They're expected to be disruptive.”

Recent Book Recommendation: So Smart But…by Allen N. Weiner

Episode Transcript

Evan Reiser: Hi there, and welcome to Enterprise Software Innovators, a show where top technology executives share how they innovate at scale. In each episode, Enterprise leaders share how they're driving digital transformation and what they've learned along the way. I'm Evan Reiser, the CEO and Founder of Abnormal Security.

Saam Motamedi: And I'm Saam Motamedi, a General Partner at Greylock Partners.

Evan Reiser: Today on the show, we're bringing you a conversation with Paul Chapman, VP of Business Strategy at Cisco. Paul has previously been a CIO at several defining companies, including HP Enterprise and Box. He has decades of experience leading teams, both as an IT executive and as an advisor to enterprise technology companies. In this conversation, Paul shares his perspective on AI, how technology will transform the future of work, and hard fought lessons on innovation that have stuck with him throughout his career. Well, maybe I'll start, Paul, can you share a little about your role today at Cisco? Cisco's obviously known across the world for a long time for innovation use technology. We'd love to hear any examples of ways that you've got technology being deployed by Cisco to kind of affect your customers that people might not fully appreciate or understand.

Paul Chapman: Really good question. Today, I'm in a role where I bring that outside-in , CIO view into Cisco, to spend time with our customers, to establish Cisco as a thought leader. I predominantly focus in and around the world of security and collaboration. And as we all know, the world has changed in the last three years and the way that we think about the workplace and workspaces and the way we think about sustainability and employee wellbeing and health and smart buildings, and there's a lot of things that go into how we collaborate and how we work today. So I get to spend a lot of time with customers that are from all over the world, from all different industries, talking about our insights and perspectives as we, Cisco, are going through a transformation to a new way of working, we're figuring a lot of things out, and also listening to customers and bringing their insights and perspectives back into Cisco to help us shape the direction that we take our portfolio of enabling technology forward.

 Saam Motamedi: Paul, as we think about the last several years, obviously one of the biggest kinds of sources of dynamism is the COVID 19 pandemic and now kind of coming out of it and how that's impacted the way we work. I'm curious about your perspective on how forward thinking technology companies today are utilizing technology to make the office a magnet and get people kind of back into the office.

Paul Chapman: I think there's two parts to that. I think it's a great way to think of the office as a magnet, not a mandate, right? And sometimes I use the term, “re-earn the commute”. We don't want to be going to the spaces that were designed yesteryear, where people get in a car, commute for two hours, sit in a cube, do some work, drive home for two hours, right? I think we've all learned that there are much, much better ways to work. I think as individuals, depending on your role, of course, if you don't have a role that's location dependent, we've all been afforded a lot more flexibility in how we choose to work. Work is more of a state of mind than it is a location. And what we're finding now is that if we are going to re-earn the commute and people do want to get back together, it's not about people not wanting to come into an office space, they do, but it has to have purpose. Space has to be designed for purpose, has to be designed for collaboration, for ideation, for training, for heads down work, for heads up work, heads together work. We use these terms to talk about how we bring people together, to rebuild social capital, to have those in-between moments and so on. It's very important that we design a space that's attractive to employees, but the reason I say it's two parts, we also have to think about the remote or distributed participant and the experience that they have. And what I would say is that there's a tremendous amount of innovation and investment that's going into the science behind collaboration: the intelligence around audio and video, the intelligence around things like translations, transcriptions, the ability to create more immersive and engaging experiences. But I think that we're really thinking deeply about sustainability, employee well-being, employee health, and the overall experience that our employees get, no matter where they work.

Saam Motamedi: Has there been anything surprising that you've learned as you've gone down this path? This is a conversation happening in every leadership team across America and particularly in technology teams, and you've begun down this path. I love the framing of magnet, not mandate, and I'm curious, are there ideas you have or things you've learned that would surprise people listening and might be interesting experiments for others to try?

Paul Chapman: Well, there's a little bit of anthropology, right? It's sort of like Jane Goodall, what goes on in the wild, right? Because each organization does have its own nuances. We see differentiation geographically and generationally, right? Depending on the nature of the work that happens in a particular geographic region or area, you'll see a different pattern in how employees are showing up. So there's a little bit of, this is why mandates don't seem to be working, because it forces everybody into a sort of a specific structure. That doesn't work for everybody, right? I was actually talking to a company just a couple of weeks ago, they have a mandate of everybody coming in on Tuesdays and Thursdays, while their studies are actually showing them that they actually have more people coming in on Mondays than they do on Tuesdays and Thursdays, which is kind of ironic because it tells you that the mandate isn't working, but they're probably achieving the goal that they've set out to achieve anyway because they have more people coming in on Mondays. You have to be thinking about studying your organization as well. Young in career, young in career have a thirst, Gen Z have a thirst for coming into an office space. They need visibility, they want to be able to join dots, they want to get exposed to leaders and so on and so forth.

Saam Motamedi: Taking a step back, I think one of the reasons why both Evan and I were so excited to have you on is, I think many people when they think of digital transformation and the role that CIOs play in that innovation, they think of non-technology native companies learning how to use technology. What's really interesting about your career is you've led these efforts at technology native companies, and so think back to some of those experiences when you were in the CIO seat, maybe at Box or HP Enterprise, were there a couple key moments that people from the outside would look at as a technology driven organization, you were able to drive some kind of paradigm shift or change an approach on how technology was used inside the business?

 Paul Chapman: It's a great question because this is one of the reasons why I ultimately have worked for companies where I'm a technology leader at a technology company, because one of the things you do get to do is you get to be that customer zero. The reality of it is that you need to be your first and best referenceable customer. One of the advantages of that is, if you're somebody like me who likes to spend time with customers, I'm a staunch customer advocate, right? I'm a security advocate, but I'm also a staunch customer advocate. You get to spend time getting close to customers, and then in doing so, you get to bring that feedback back into your own organization to help shape the product. We did this at VMware, we did this at HP, we did this at Box.

Evan Reiser: I'm so fascinated by your experience at Box. Are there any anecdotes or stories of the kind of innovative things you deployed there that the average customer of Box might find surprising about how you guys worked on the inside?

Paul Chapman: The way that we went about innovating. I think one of the things, and I'll call it more of a principle than anything that we thought about, was how do you take the work out of work? How do you create as frictionless free an experience for your employees so they can do their best work? And I always used to say, look, if it takes a human being less than half a second to think about it, we can digitize it. Now, that isn't always exactly true, but in theory, that's sort of the mantra that we were operating under. So I think something that might be interesting inside sort of the thinking inside the organization was, that's what we were looking for all the time. I'll give you one simple example. Two-factor authentication. Okay? So people do this all the time, they forget their passwords and the process of resetting their password, like AD password. Now remember at Box, we were working with some of the world's most risk averse companies and agencies, so we had very, very tight parameters around how security was controlled. You enter your password incorrectly three times, you're locked out. The problem is that when you go to reset your password, you have to typically enter an IT help desk ticket, or you have to go into some portal, or you have to do something to request the change. What we did is we took just one simple step, we automated the two-factor authentication such that if we picked up that somebody had logged themselves out, we would send them a push to say, did you lock yourself out? Do you want us to reset your AD password? And we do that automatically. That one simple example saved hundreds and hundreds and hundreds of hours every year, hundreds of hours, every single year, one small sort of digital automated step in resetting AD passwords. And there are many, many more like that.

Saam Motamedi: Certainly Evan and I believe that we're in the early innings of the AI wave, and it feels like a wave that's going to be as impactful as some of the largest prior technology waves. Maybe to start, you were obviously there early and driving some of these prior shifts, whether it's VMware and Cloud Computing Infrastructure, Box is one of the first major Cloud SaaS applications, for those of us who weren't in the trenches driving those prior technology waves, what are some of the lessons that you take from those waves that you think could play out again or not in this AI wave?

Paul Chapman: Yeah, I think if you look at some of the AI conversations that have been happening in the last few months, it's been nothing but, right? It's what we can hear in this too. I actually think we're actually in the early stages now of fundamentally a shift, and I think that we can no longer operate at human scale and we're shifting to operating at what you would call machine scale. I think about this in terms of hyper productivity, right? Which AI is part of, and I think that what we're seeing is, if you think about streaming architecture and you think about the ability to respond and act real time on data that comes to us, it's coming to us now in a real time streaming way such that we as human beings can't react and respond fast enough. It takes machines. You have to build more intelligence into what you're ingesting. We cannot keep up as human beings. We've reached the physical capacity of human beings in terms of speed, right? You know what a billionaire can't buy? One second of time. If we can give people back the gift of time through this shift to hyper productivity, I think we're gonna see a huge fundamental paradigm shift in how we operate.

Saam Motamedi: Paul, let's fast forward five years, right? The three of us show up to our respective offices, how are we gonna be working? What will that hyper productivity with AI look like? What do you think some of the applications or experiences will be?

Paul Chapman: It'll be interesting. Somebody said to me, how do you describe technology, right? And I used to use this term, well, I think technology is anything that was invented after you were born. So we're asking ourselves questions about things that were invented while we were born. I would actually think that the interesting question would be to ask somebody in 20 years who is not born today, right? You know, it's like my youngest daughter, you ask her a question and she immediately just says, hey Siri, da da da, or ChatGPT, I introduced her to ChatGPT recently. You're naturally gonna gravitate towards these different types of user experiences, right? Not user experiences, the way we operate, the way we think, we will naturally gravitate to the chat interface. We will naturally gravitate towards, if I have to stop and think about it for more than half a second, why can it not be automated? I spend a lot of time talking to customers about the digitalization of real estate, smart buildings, smart building technology, the amount of sensors and the amount of intelligence that we can now get from buildings in terms of how they're being used, making smart decisions around how we think about sustainability, power of ethernet, how we think about occupancy, how we think about how space is being used, how we adjust thermal temperature based upon the number of people in a room. All these things now are programmable into buildings. In the future, it's not going to be an event, it's just something that we're going to do.

Evan Reiser: I'd love to hear any specific anecdotes you have about-, because you've talked to a lot of customers, right? And you get a lot more visibility into what's happening in enterprise than me or Saam or probably anyone else listening to this podcast, right? And I think that people are just kind of tormenting on AI because it's like, hey, it sounds a little bit futuristic, there's a lot of snake oil out there, but there's actually some real examples, right? We've heard many on this show about where people are actually getting results.

Paul Chapman: You're right. It's almost becoming boundless, right? Where we see them, right? So here's an example: through intelligence now, we can proactively recognize or understand the quality of service somebody is getting in their home office experience when they're on a video call. We can automatically diagnose, we can automatically troubleshoot, we can automatically adjust the quality of service in terms of dampening the video down, increasing audio, whatever it might take to create the optimal experience. It doesn't require human beings, it doesn't require somebody to have a horrible experience and go raise a service ticket after the event, whatever it might be, right? We're able to take things now like a high definition video that cannot be sent over a low latency, low bandwidth network, we're able to use neural networks to say, okay, let's take this downgraded video and with artificial intelligence, we can actually replace the pixels that are missing and actually regenerate a higher quality video than the original one was recorded in. These are all things that are being built into how we work today.

Evan Reiser: At the end of these sessions, we like to do a bit of a lightning round just to capture the one tweet responses. Maybe, Saam, you wanna kick it off with the first lightning round question?

Saam Motamedi: Yeah, absolutely. Paul, you've been a CIO at several amazing companies. How do you think companies should measure the success of a CIO?

Paul Chapman: Well, Sentiment Analysis is always a good one, but it's very hard when you're a CIO. Sometimes people refer to it as, “career over”. But I'll tell you, I think that CIOs are expected to be disruptive and failure is the currency of risk. I think all too often the CIO behaves in a very conservative way, but that's not how they're measured and what's expected of them, they're expected to be disruptive.

 Evan Reiser: What's one piece of advice you wish someone gave you when you were stepping into your first CIO job?

Paul Chapman: I think that you need to listen to be wrong versus listening to be right. I think it's all too often that you come in with the answers or you think you have the answers and I would say the most important thing is you need to be listening to be wrong. Be careful of techno panic as well. And trust me, if you always do what you always did, you will always get what you always got. So avoid that. “The pain of change is mandatory, it's the suffering that's optional,” is the other thing I like to tell people.

Saam Motamedi: Maybe speaking about other functions on the leadership team, how should CIOs position themselves to best collaborate with the rest of the C-suite?

Paul Chapman: So I think that this is one that's been talked about for a long time, right? And I think it's actually relatively straightforward. Don't talk about technology. There's a given that you know the domain and you know how to curate the right outcomes with technology. You need to be talking about business outcomes, business challenges, bringing outside-in perspectives, outside-in views, bring your network of intelligence into the organization and have those business led conversations. And I also think that any CIO, especially in technology companies, should be getting close to customers, getting closer to revenue, being a friend of sales, because you don't get rewarded for being an operator.

Evan Reiser: This is maybe a little bit more on the personal side, but what is something you think will be true of technology's impact in the world that most people today think is science fiction?

Paul Chapman: Well, where I think we have the biggest opportunity is in how we think about the environment, the planet, sustainability, and every company having sustainability goals that are tracked and measured. The SEC is now scrutinizing companies around their publicly stated goals when it comes to sustainability and driving to net neutrality and so on. I think that that to me is where technology can really, really help and AI can help make decisions now., important decisions now that are going to benefit us in 10 years, 15 years, 20 years, and do so with a high degree of certainty that that's going to be the outcome. Today we're afraid of what we can't see and don't know, so we're cautious on decision making. But we need to make faster decisions today about how we're going to impact the environment for years to come and I think technology and AI can help us get there.

Evan Reiser: Paul, thank you so much for sharing your thoughts. Really great chatting with you as always, and looking forward to talking again soon.

Paul Chapman: You bet, thank you.

Saam Motamedi: Thanks for joining us, Paul.

Evan Reiser: That was Paul Chapman, VP of Business Strategy at Cisco.

Saam Motamedi: Thanks for listening to the Enterprise Software Innovators podcast. I'm Saam Motamedi, a General Partner at Greylock Partners.

Evan Reiser: And I'm Evan Reiser, the CEO and Founder of Abnormal Security. Please be sure to subscribe so you never miss an episode. You can find more great lessons from technology leaders and other enterprise software experts at

Saam Motamedi: This show is produced by Luke Reiser and Josh Meer. See you next time.