Ep 44: From Noise to Signal: How AI is Shaping the Future of IT with Cloudflare CIO Mike Hamilton

‍Evan: Hi there, and welcome to Enterprise Software Innovators, a show where top tech executives share how they innovate at scale. In each episode, enterprise CIOs share how they've applied exciting new technologies, and what they've learned along the way. I'm Evan Reiser, the CEO and founder of Abnormal Security.

‍Saam: I'm Saam Motamedi, a general partner at Greylock Partners.‍

Evan: Today on the show, we’re bringing you a conversation with Mike Hamilton, Chief Information Officer at Cloudflare. Cloudflare is a cloud connectivity company that helps businesses deliver content and applications everywhere in the world while keeping them secure. More than 20% of all internet traffic flows through Cloudflare’s networks, making them an indispensable part of modern internet infrastructure.

In this conversation, Mike shares his thoughts on how AI helps filter the noise in cybersecurity, the seamless integration of AI in business operations, and the power of AI to automate the mundane.

Well, Mike, first of all, thank you so much for making time to chat with me today. Um, I know we've talked a bunch in the past and, um, you know, we have a lot of similar, I think, upbringings in technology. Um, you've had a really, you know, incredible career. You've worked at some really notable companies. Do you mind maybe giving our audience just a little bit of background on kind of how you got to where you are today?

Mike: Yeah, absolutely. I think it's, it's really fun to think about when my career started, um, which was actually after graduating with a bachelor's degree in molecular biology. And, uh, I'd always been into computers, even though like I didn't have much money growing up. I went to computer camp when I was 12.

And it's, it's probably like really foreign for a listener to think about what the world looked like in 1982 or, you know, 90 something, especially since they've grown up, like my kids have completely grown up with technology around them. But my, I kind of laugh at my own perspective from looking back. So when I look back on how I thought about computers and technology, when I was a kid, I was like, of course, everybody's going to use this.

And of course, everybody's going to be as excited as I am about it. And so when I went to college, I was like, look, you know, I, I'm interested in life sciences. I want to understand how things work from a biology perspective, but I kept in the computer space. And then when I emerged from college, I w I walk into business where it's like, Oh, you understand computers.

Oh, wait, we need to talk to you. And it's almost like, um, I like to describe the earliest stage of technology and business as, uh, introducing something completely foreign to the business. Like there's the business and it's running, but they, they, much like how the conversation on AI goes now, the conversation back then was, we've heard about this thing called a computer.

We should probably get one. We should probably think about how we integrate this into business. And so a lot of my career early on was, was starting there. Like, how does technology work in a business? Like every business knows they need to seize it. But how does it actually work? And it's been exciting to be a part of that growth and development from being in public sector, where I started my career moving into private sector, high growth startups, where like, I, it's just like, I found my calling when I got into my first high growth startup.

It was like. This is what I want to do. I get to be a part of the business. I get to work with business leaders and bring technology to, to make their life better. And so it's, it's been a fascinating journey, but I literally started my career in help desk and in entry level support in the nineties when people didn't even have a computer at home.

You know, and so they're coming to work. That's the only computer they ever touch. It was a very different world compared to now. We want to be able to talk to our computers and have them do things for us. So fun evolution, it's been wild. I'm trying to figure out how to even write it down to tell the story because so much context is missing given the rapid development of it.

But it's, it's been an interesting life to live in the middle of this tremendous evolution. 

Evan: Well, you've had to just say, um, through, through luck and chance and skill, I mean, you've been at some of the most interesting, you know, technology companies, right in, in the enterprise, MuleSoft, Salesforce, Databricks, Cruise, you're now the chief information officer at Cloudflare.

Um, you know, for, for me, Cloudflare is a super common name, right? Probably talk about it once a week. Um, you know, uh, but we'd love to maybe, do you mind sharing a little bit for our customer or for our audience? Like, you know, what is Cloudflare? Who are some of your customers? What do you guys do? Right. For maybe some folks that might not have the full context.

Mike: So Cloudflare is an incredible company from, from a product perspective. I would say it's the easiest way I would describe it. And what compelled me to want to join is that it's the coolest set of Legos you could possibly ever find. We were talking about Lego a moment ago. I've got the Millennium Falcon back here.

You've got yours, but it's, it's an incredible array of developer tools and infrastructure tools that allow anyone to really scale and then be protected. Like, so it's, it's a combination of what I would really refer to as business class internet really is what we've created. We've created an internet that can provide you with the solidarity of a business network, but running globally across the entire planet.

And when I think about an availability zone in Cloudflare terminology, I think about earth is the availability zone because that's what we've designed. We've we're no more than 30 milliseconds away from eyeballs. You know, people who are looking at content and that gives us a unique advantage to, to provide incredible service, but also incredible protection because we see so much about 30 percent of the internet traffic runs through our network.

And so we're able to see things while they're happening or while they're emerging and then give all the benefit of our learnings to our customer. So as we evolve, our customer's benefits evolve as well, because at the end of the day, our customers are either trying to innovate. With something they're delivering to someone else, or they're trying to protect themselves to be able to grow and survive and thrive, in the business that they've created, and Cloudflare gives them all of the pieces to do that extremely well. 

Evan: Um, I love, I love that, uh, that's a business class internet, right? It's a good way to think about it, but also it's always a understatement. I know Cloudflare does so many things, but before we kind of go into, you know, more details about Cloudflare, um, you know, obviously, uh, you know, Cloudflare was a you know, early leaders that, you know, cloud transformation, you know, is now a leader in this AI transformation.

Um, maybe kind of stepping back when you think, you know, you've, in your career, you've seen multiple technology platform, you know, cycles and adoptions. Um, as we're talking about a minute ago, before we start recording AI is at all time hype levels. Um, but there's also some substance there, right? I think a lot of the customers I talk to for my business right there, they're trying to figure out kind of where we are in the hype cycle.

You know, what is, kind of, marketing and what is real. What are your kind of thoughts on that as both, you know, someone that, you know, helps support an organization to deliver AI solutions, but also, you know, you've been a, um, an implementer and deployer of kind of AI technology enterprise for awhile, where do you feel like we are in that hype cycle?

Mike: So, so I, I, I'm going to go back to my original statement around like early businesses thinking we have to get one of these computer things in our company. Right. It was that clear with, you know, with the success that IBM was having back historically, like, Oh my God, we've got to have computers in our company.

It's going to give us some kind of advantage. What that advantage is, is up to how we use the tool. The same sentiment applies for artificial intelligence. Um, if we start with the idea that like asking the question, is artificial intelligence really here to stay? Is it really ready? Because it's, it's actually older than people think it is.

Artificial intelligence as a technology goes back decades, back into the fifties, starting with academic papers. The technology has been there for a long time. The idea has been there for a long time. But the scale of how it gets delivered has been one of the challenges. It's been a limitation. Storage was expensive.

Compute was expensive. Memory was expensive. And we're at this interesting turning point now where we've developed something that can actually support this incredible technology to take off. So that's one piece. Is it going to stay? Definitely. Um, at which point now all, all business owners in all parts of the business are under the pressure of like, god, if I didn't hit my goal and I didn't use artificial intelligence, man, am I in trouble? Like it's just a lose, lose, right? If you didn't use artificial intelligence and you didn't hit your target, somebody is going to be asking you, why weren't you trying to leverage this more? And so I think leaders at the top are under more pressure than they've ever been in their career.

And we've seen that with even the advent of SaaS, like it started to move the decision and the power into the line of business, but then at the cost of the pressure of like, how do we become successful with this technology? In the case of AI, I think it makes it quite a bit different because the artificial intelligence itself is a value add. And so, that like the next thing is that we're ready. It's here. We're ready. Buyers have a lot of pressure to get. Now let's get to the third thing, which is like, where will it be? And the answer is quite frankly, everywhere, which allows me then to talk a little bit more about CloudFlare because, you know, so first of all, it's going to be everywhere, it's going to be in big spaces and little spaces.

We have the open AI sort of perspective of like these massive models that could require a nuclear power plant to run the model in the first place. Right. So that's one, that's one thought, but that's not 

Evan: right. 

Mike: Yeah. And, and, and quite frankly, it's, it's the thought that probably freaks people out the most.

So when people are exhibiting fear about AI, it's like how 9,000 or, you know, something else where it's like, Oh, it has too much control. It's too singular of an entity. And even that's, it's like, it's science fiction for a reason. It makes a great story, but in practical, you know, where the rubber meets the road, that's not exactly what, what the outcome of that massive intelligence is going to be.

It's really more about like having a bigger perspective on humans. Like I think of, of OpenAI strategy of artificial intelligence, almost humans being able to look in a mirror at humanity and say like, what are we, what are we saying about ourselves? What does the mirror tell us about, about what we've written and what we've captured?

And so in a large model, it's kind of interesting philosophically. What does humanity have to say about humanity based on everything humanity's ever written? It's kind of an interesting thing. Uh, especially for the objectivity of a computer. Like I, I laugh that uh, artificial intelligence suggested that someone could get the cheese to stick to the pizza better by using glue, because the artificial intelligence doesn't have the context to know that glue would taste terrible and possibly be a serious risk to someone's health. So terrible idea, right? And it shows some of the gaps in the technology because it's not human. It's, it's really just logic. It's, it's logic and it's sort of weights and the way that weights apply out in a really big model.

But I think it's really interesting to talk about the extremely specific stuff. And this is where I think, you know, in Cloudflare, we've, we've presented artificial intelligence as one of the key bricks that you can develop with. So we have our workers platform, which is serverless and it's global serverless.

So instead of deploying code into an availability zone, that's regional, ours is global. So we're, we're always as close to the eyeballs as we can possibly get. Someone using your application is getting the closest strategy that they can possibly, uh, leverage to deliver an application, especially if something they're trying to create from scratch.

Then add to that, the fact that we have workers AI, which allows someone to deploy models globally, you know, in, in more than half the data centers we have have this model capable capability, they have the GPU capability and the backing incredible. But then we also have the vector database distributed vector database.

So it allows you to keep the database close to the user as well. So that it's an incredible experience. And these novel pieces are foundational for the more specific use cases, because I really think that the longer term and broader value of artificial intelligence is in the small, like the, the niche problems that it solves.

Like, how do we help humans focus more on what they do every day or like on the, on the cognitive stuff that the engagement level is high, right? Like we need high cognitive investment in this thing. And that's where we want humans to be able to pay attention. Artificial intelligence gives us the ability to take away the things that people don't want to do and focus a lot more on, on the things that they can do.

I think adding to that too, there's, there's this, and this is more around how Cloudflare functions as a security company. There's the signal from the noise. So another thing that artificial intelligence is incredibly good at and has been for some time is detecting signal in a way that, that humans would miss because we're just, we're not able to pay attention to that much information at once, but a, but a, an artificial intelligence model can, you can look at all this data and go, look, look here, look here, look here.

Now, sometimes the humans still required in many cases, like what do we do with it? But we would have missed it entirely if it wasn't for the artificial intelligence helping us find it. And the more data we're surrounded in data is the new oil. The more data we're surrounded in, the more this is relevant.

Evan: Yeah, that's, that's good. Now I just, I, I, one thing I heard from, uh, uh, one of your peers at CIO, I talked to, he said, um, you know, we still have to find the needle in the haystack, but the AI has to get rid of like 99 percent of the hay, right. So it's still like work to do, but, um, it's a great, it's a great tool to help find, you know, help find more signal in the noise.

Mike: Well, I think like Einstein said to something like, why did you stop looking at one needle? Like, if I found the first needle, I wouldn't stop looking. And I think artificial intelligence helps us there too. What if there's not one needle? What if the haystack actually has 50 needles in it? Like we, we would stop at one as humans.

The artificial intelligence doesn't care. It's like, look, I found 50. We're like, Oh my God. What does that mean? 

Evan: Exactly. 

How do you think AI is going to transform how businesses run, right? If it's five years in the future. Right. He said, well, every company will be doing X with AI. Like what are a couple of things in that bucket?

Like one, one you're kind of suggesting is, you know, kind of information knowledge management, right? That seems like that's a problem. Every organization has, you're kind of also implying something around. You know, um, engaging with customers, right. The customer support or, you know, through sales, what are some of the things where you're like, Hey, we, we kind of screwed up his ID industry, right.

If we haven't, you know, made major upgrades in these areas with some of these new technologies coming out. 

Mike: Um, I, I think that the area that I want to see worked out the most is around like the integration sort of space and how we get business systems to talk to each other. So I can tell you as an it leader, um, the, the benefit of the SAS world has been that my buyer, my stakeholder inside the business is now.

Able to make some decisions on their own and try to find good product fit for themselves. And that's great. But so often they come back and they're like, okay, I bought this thing. They said something about integrations and then it's like, yeah, there's tooling for that, but like we have to develop it and it takes a lot of time.

And I was just talking to someone earlier today in the AI space that was talking about. How their, their technology can read API specifications and then start to understand, like build a context around them and start to understand how to create automations based on understanding the specs involved. And I do think that that's something that the AI industry has to nail.

Um, and we were having the conversation into, like, I, I, I was poking fun at sort of this demo that I saw, which is like the, uh, the, the automated bot assistant is calling the automated bots customer service rep. And I was like, I think there's a world where they need to be able to signal each other to go like, I'm a machine.

And they're like, Oh, I'm a machine too. And it's, you know, Oh, let's take this conversation to a different level. And I think there's a future state in the, in the, in the world where we have this, uh, Protocol that we established around, uh, how AI is talk to each other to broker transactions like this. Like, how do I change my doctor appointment?

Right. And then what's the offer counter offer sort of, uh, uh, protocol we develop around this, but like, I think there's a, there's a meta conversation, which is like, how do we have the conversation about the conversations? Right. So. As we start to get more intelligence around, what do people need to do?

Then how do we have the conversation around it? Um, that's one of the things that I find fascinating about some of the AI tooling I've seen as well as like, when you're, when you understand what people are asking the AI, like, uh, there, if you were to sit in a room with a bunch of people and like, you're like, okay, what questions do you have?

Right. And they're going to be like, I don't know. Like, like we immediately all go sort of blank page problem, you know, when, when somebody asks a question yet, if you take away the human for a second, you give them a prompt and you just say like, Hey, what do you want to know? People start to get creative and they start to kind of unlock and they're like, Oh, I'm not afraid to tell the robot this.

Cause I don't think the robot's going to judge me. Right. I'm very certain. It's not going to judge me, thankfully. Um, and so then we can start to get these trends around like, Hey, what are people asking for? Like that was one of the benefits I had had in past two companies with glean is what's the most, the most common things people are asking the automation and it starts to uncover.

Gaps in the business where it's like, Hey, we should be doing more over here. Like, Oh my gosh, people don't know how to find this or this data quality is terrible. And it points to things that they're not willing to tell you.

Evan: Yeah. That's actually a really interesting concept, right? You're So to repeat, you're kind of suggesting that, um, you know, people kind of are a little bit, you know, maybe uncalibrated when in terms of like, we're like reasonable expectations for how I should be using technology.

And so there's some questions that maybe they don't know to ask, or they don't know what is reasonable, or maybe they're scared to ask for some performative reason. Right. And so you're, you're kind of stressing like with these new kind of interfaces, right, to collect that feedback, you actually better understand and diagnose and debug and ideally solve different problems across the organization and workforce.

Mike: Totally. I mean, one of the things I love about artificial intelligence, like it, even just an opening chat GPT prompt is being able to have a conversational thread with it. Like, tell me more about this. And in some cases it's about as good as like a seventh grade research assistant. In some cases it's about as good as a college student, but the benefit is that it's consolidating information that I don't have to pick through.

And I'll give you a statement that I've made before. That's, it's kind of funny. Um, a lot of business brings it problems in the following form. Hey, Mike. I need a bicycle, I need it made out of Legos, and I need it by Friday. So, the deadline, the solution, is all built into the same request, right? And, and that's because people present solutions as they understand them.

And so, our job in IT, for example, is to, to know more, to know how to do things at scale, to do things that will keep the company moving forward at scale, and a Lego bicycle is not going to do that. Right. Like, and we know that, but at the same time we have to listen to them and say, like, wait, why, why a bicycle?

Like, what are you trying to accomplish? And I think there is some value in having something to run by a computer first. Right. Like I need to, to find a way to reduce the amount of time it takes to go from us, you know, to sales qualified lead to a sales accepted lead, you know, what, what might be some solutions to do that and have the AI help sort of answer some of these questions so that they don't feel the, the, um, The pressure of talking to an IT person, like IT has developed a bad reputation.

Unfortunately, like I I'm always been more of a people first IT person, but you know, there's every TV show in the world is always like, Oh God, I have to go talk to the IT guy. That's going to be terrible. I'm going to feel stupid. He's going to make me feel stupid, you know? And, and that's not the relationship we need to have the relationship.

IT wants to have with the business. At least if you work for me, um, is like, how do we help you scale? How do we help you hit your targets? Right? Like, how do we, how are we. Enabling you to do your job better. I gave a talk where that's called the wingman talk from my history. And it was like, we're your wingman.

You know, we have our own plane to fly. You have your plane to fly, but I'm here to help you with your mission objectives. That's why I'm here. Right. And I think that's the model that IT needs to follow. Uh, but I think artificial intelligence can help take away some of the fear of like, I don't feel like I know enough to talk to IT.

It's like, well, then just ask a robot for a while and see what it tells you. 

Evan: Yeah. I think you're right. Like a lot of times the, you know, I think it's true with it and also other like, um, you know, it can happen with like legal teams and security teams where you can kind of devolve into this like service relationship versus a true partnership.

And I think that the model you're describing is, um, you know, I, you know, I come from product management. Think about, it's kind of like a customer oriented, like product model, right? It's like, Hey, now you're asking for the bicycle, but like, why do you want the bicycle? Are you trying to get someplace by Friday?

Right. Okay. Right? And it seems like the best IT organizations are, don't just accept the requirements or accept the, you know, stated requirements. They try to really go and learn, Hey, what's the real issue? What do you need? And let us as technology experts help recommend a solution that achieves your objective, right?

Versus, you know, something we think. And so that requires a bit of, you know, customer obsession, customer empathy, kind of just like, I think it was a product orientation mindset or at least a customer orientation mindset. How do you kind of. Like are there traditions or rituals or frameworks you apply to kind of, like, how do you build that into the culture of, you know, the teams you, you lead?

Mike: So I've, I've taken a few approaches to that. Um, I'll start with my favorite book, which is a more beautiful question by Warren Berger, uh, and very appropriate for the topic we're talking about. But the idea of the book is that knowledge is essentially free and readily available. And so, whereas your skill or how you were perceived as valuable to an organization used to be how much you knew, um, Um, but now it's more about like, how, how good is your power of inquiry?

Like, are you able to ask the hard question or the right question for, for what we're trying to get to? Uh, and there's a technique in that book called question storming, which I'm really a big fan of, uh, I'll tell like, I ran a session with a, with two teams one time. They were stuck, they were supposed to do a POC, it was supposed to be done by the end of the quarter.

And, uh, they're both completely still like stalling. And so I attend one of their meetings. And what I see is a bunch of very smart people pontificating about how much they knew about the topic. And so I was like, all right, we're going to do something different. And I present them with a blank whiteboard and some post it notes.

And I'm like, all right, I want you to put a sticky note on the board for any question we would have to be able to answer for this POC to be a success. And they're like, oh crap. Like it, it, it takes them out of this. Like, I have to show you how much I know mode and more of like, wait, you're asking me to tell you what I don't know.

And actually I don't know. And like, Oh, we have to answer this thing. Oh my God. And so like the first step of the exercise was to collect the questions and then group them. And then the second part of the exercise was how would we answer it? Like, which ones are the highest priority to answer? And then the third phase was how do we answer them?

Like, what's the scientific process we could use to answer these questions? And that got the team out of this sort of stuck mode. And I think the same thing works with, with, uh, With our stakeholders as well. Um, I, I, I remember this nervous tick I developed from, uh, starting a new job and going into a session with a stakeholder where the, the product manager on my side was like, so tell me your requirements.

And I was like, Oh God, I really hate that because that's the methodology, not the, their relationship, like requirements are a part of the methodology. That's behind the scenes. That's the part of the magic trick. You don't need people to see. Um, what we need to do is like help them understand what they're trying to accomplish.

And so I took the person aside later and I said, uh, What if my requirements were flour, eggs, milk, baking soda, uh, you know, what would you make? And they're like, well, uh, uh, uh, you know, I guess, I don't know. That's a cake, right? I don't know. It could be muffins, right? Like there's a lot of things this could be.

That's like when you ask someone for requirements, that's a really weird thing to ask them because you're putting their brain in the wrong frame of mind. They're a leader. They have a business to run. They have a, they have an objective to hit. And so the question is wrong. It's broken. What are you trying to accomplish?

What questions do you, do we need to be able to answer? What questions do you need to be able to answer to be successful? That's really the cognitive engagement we're looking for. And it's, to me, it's vital because it's, that's how we build the trust in the relationship. Um, It does us no good to complete 12 month project cycle.

God, why would you have a 12 month project cycle? Let's say a three month project cycle. Doesn't, you know, I completed three month project cycle, but if my stakeholder isn't gloriously satisfied with the work we did together, we failed. It was a complete failure if we didn't do that. And that, that comes down to relationships.

It comes down to understanding their core problem and what they're trying to solve. And you know, it's, it's way more human than it is technical. 

Evan: So Mike, I want to take us, uh, sorry. I feel like we could talk about this for like four hours. 

Mike: Oh, we can totally, this is my thing.

Evan: But I do want to, um, you know, give, give me a little bit of time. I do want to get back a little bit to, um, you know, talking about kind of AI and Cloudflare. I would love to hear just, um, you know, some of the ways that Cloudflare is using AI that you just feel kind of excited about. 

Mike: Yeah. So we use a lot around our business intelligence and we're increasingly wanting to build out the workers, uh, solution internally for applications.

So I think one of the things I love most about our product line is the way that You get a ton of benefit from buying an individual tool if you need that tool, but you get even more benefit from the ecosystem. And so let's talk about like building a custom AI application for an enterprise that includes zero trust, right?

So you can, let's say that your application needs an on prem server, and then it also needs a custom, you know, the custom application front end, and then it also needs like the authentication system, right? So between our zero trust strategy, plus the workers that a, the workers, Platform plus the workers AI, you know, you're able to get high performing applications out of, uh, out of our network in our capabilities, like with all the tools that you need to create this happening.

So now you can have like, you can on ramp the on prem server with an agent. This is like, okay, now this thing's on my zero trust network. Instead of trying to figure out like how to get the network on zero trust, we have many ways you can get your, whether it's putting your whole data center on zero trust, whether it's putting an individual node, you can finally take that machine.

That's sitting in a closet somewhere. And on ramp it into a zero trust environment and turn the firewall rules off that allow somebody to access from the outside. And that's part of our technology stack. So I think like. I get really excited about that. Um, especially from the standpoint of how we use our own product as customer zero.

So we already use it a lot in business intelligence. We're already doing conversational intelligence with it internally, but I want to get to a level also where we're able to, um, serve our own internal population better with our own tooling. Like how do we answer questions? Inside the company and provide people with insights that they need by connecting the data that we have with the resources that we can build, you know, out of the various components.

Um, and it's hard to talk about any more specifics because of the fact that it's individual pieces and capabilities that we have, and those keep getting cooler. But what gets me excited about it is how close it gets to the user. Um, like, I always find it interesting with cellular technology because, The telephone companies are always sort of pitching this thing.

They're like grossly oversubscribed and it's deeply unimpressive when you get a lot of people on a single tower, right? Like if you've ever been to the mountains over here, uh, and, and there's a lot of people in the mountains, like all of a sudden cell services worse than dial up, you know, they talk about a lot of things.

And when, when 5g was launched, they're like services at the edge, you know, this is going to be a game changer. And I'm like, yeah, not really. Like, like the internet, like I defined the edge a little bit differently. And I think Cloudflare is absolutely nailed it. Like. We have the edge within 30 milliseconds of everybody.

We are, we have applications that are practical that you can build tomorrow at that edge that gives you the service. We have a global availability zone, which allows, you know, you to deploy these applications close, but not think about, you know, how many instances of the thing do I have to run to get it out to my, my users?

Um, that's just incredible. And I also think it's incredibly powerful to say that like, whether you're trying to build a business class intranet. Where it's only secure content that only your employees are allowed to see, or whether you're trying to build a customer facing application, you're getting all the same benefits.

Cloudflare has an incredible capability to not only, you know, make these all very responsive, but to protect you as well. We get massive amounts of intelligence on, uh, on what's going on on the internet, what's the latest bot storm, or what's somebody trying to do that's nefarious. We also have. You know, less nefarious, less scary sounding things like traffic optimization.

Um, we use artificial intelligence to decide, like determine how, how, which is the fastest link to use. Is it a backhaul link? Is it another internet link? What's the fastest way to get there? Um, as a network nerd myself, I love that. I think it's fascinating because if you're a network nerd, you're like, Oh, we're adding protocols to do that.

It's like, yeah, but incredibly slowly. I mean, like they only converge every so often, like our Argo technology is actually converging all the time. And it's finding like based on the current flows, where's the best way to send this traffic? It's an incredible technology from a, from a user experience perspective, but isn't user experience what this is about anyway, right?

Like I want, if I'm, if I'm in business and I'm building on the cloud for network, I want my customers to have the best experience possible. If I'm delivering solutions for my employees inside my zero trust boundary, I want them to have the best experience possible. And I think that that's where we just absolutely shine.

Evan: Um, okay. Mike, I have like so many follow up questions for you and Joshua yelled me after the show. Cause I didn't, I didn't, I asked like. 2 percent of the questions I was supposed to, um, we do a little bit of time. So I wanted to skip to like our, our lightning round, right? So at the end of the show, we'd like to do a kind of, uh, a quicker hits section, right?

So looking for the, um, kind of the one tweet to answer these and these questions I know are very hard to answer in one tweet. So just please forgive me. You can, you can take it out on me, you know, after the show. Um, okay. So, so kicking it off, how should companies measure the success of a CIO? 

Mike: I think ultimately it boils down to whether or not there's the stakeholders that work with them at the C level are comfortable and excited to work with them or not, like, do you feel like the CIO listens to you or not?

Are they really helping you achieve your objectives or not? It really boils down to that. You can talk KPIs all day long, but those KPIs are business KPIs. But if you don't want to work with a person, then it's really hard to make that, that relationship span out. And then what you have is misdeveloped organizations, right?

Like if I only worked on my biceps, it might look pretty weird, huge biceps, no other muscles, right? But the businesses start to get out of proportion like that. Cause it's like, Oh, we're strong in marketing, but we're weak in something else. Cause I think it's along with them and not this other group, right?

That's terrible. It can't work that way. Yeah. 

Evan: Especially in enterprise where like you kind of need all It's like kind of like all gears in the watch have to work together if you want to tell accurate time, right? Um, so, so it kind of begs maybe the follow up question. Um, you know, how should CIOs best position themselves to effectively collaborate with the rest of the C suite?

Mike: Well, I think it boils down to beginning with, um, organizational objectives. And so I like to think about the old, the old quote of, uh, how do you carve an elephant out of stone? Well, you, you shave away every part of the stone that doesn't look like an elephant, um, from a business objectives perspective, there's probably only two or three things that a company can focus on at one time that are truly transformational and I think you have to shave away everything that's not those things and, and figure out how you're executing on that first.

How are we executing on the two or three things that are competitive differentiators that are unfair advantages that give us a position to really achieve market, you know, capturing market that we want to capture and everything else is secondary. There's a lot of operational friction we can reduce, but it goes back to the jar and the rock, like you can only fit so many big rocks in a jar.

And then you can start to fit some pebbles in the jar and then you can fit some sand in the jar. But like the big rocks have to be only the things that are transformational that matter to the business for its success and growth. 

Evan: Switching gears to the personal side. Um, love to hear if there's a book you've read, um, that it's had a big impact on you or kind of how you, how you work or how you lead.

Mike: One of my favorites is, uh, leadership is language by L. David Marquette. Um, he starts with the premise that like companies say lots of things like we want you to speak up and we want you to share your opinion and take risks and blah, blah, blah.

And he actually shows through captured transcripts in a lot of cases of things that turned out to be disasters of how everything else that middle managers say beyond that point. Contradicts those principles. Um, so I love his book. He's a really interesting guy and he has the great things, the A, the concrete examples and B, he actually has some techniques for how you can run your meetings to help overcome those, those issues.

Um, another one that I think is appropriate for an AI discussion is Tomorrow Mind, uh, Dr. Seligman's one of the authors of that book. He's the founder of positive psychology. He was tasked to, um, to understand PTSD in, in veterans. Uh, and, and so he studied PTSD for some period of time and he realized that psychology is largely focused on fixing problems as opposed to building resilience.

And so the entire idea of positive psychology came out of how do we build resilience? He started with the question back to asking important questions of why is it that 85, 15 percent are affected with PTSD in military service, but 85 percent aren't. Can we study the 85 percent that aren't and try to understand.

What it is about them that, uh, that, that makes them so resilient. Now, how does that translate into modern business? Well, the world is full of volatility, uncertainty, complexity, and ambiguity. VUCA is the military term for that. We, we were, we're no longer able to sit on the same job for 20 years and expect to retire with a pension.

That's not how the world works anymore. How do we deal in a world of uncertainty? How do we run every day and like, make sure that we're addressing the important things and having resilience to wake up and get excited, even about how we address. Living in a world full of change. So those are, those are key books that have really influenced me a ton.

Evan: What's an upcoming new technology that you're personally most excited about? 

Mike: I mean, it's so hard not to answer that with AI right now. Um, like, no, it, it is, it is kind of everything, but I'll, I'll give you a more specific answer, which is that I'm interested in how AI ends up helping in the little ways, um, and how people interact with it every day.

I think in the same way that we're used to having a cell phone that we carry with us that we don't think twice about anymore, I think that we're gonna have some way that we're interacting with AI every day that we just don't even think about. And I'm, I'm excited to watch that emerge. And I'm excited to see how it helps people, especially like we created this monster of social media and all these other ways that technology can be bad for people.

But I'm, I'm interested in how artificial intelligence will be good for people. 

Evan: What do you think people most underestimate about the opportunity with AI? 

Mike: From an underestimation perspective, I think that it's too, it's thought about too much from a technology perspective and not enough from a humanity perspective.

You know, we have to answer big questions like, how do we, how do we feed the world? Um, how do we, how do we make sure that economic distribution, uh, encourages growth in, in areas where people are living in poverty? Like, I think there are hard questions that AI can point to that can help. Like if it has all the data, but it also develops a bigger perspective that maybe we're just missing some obvious things, some little things that we could change that would affect the whole world in a positive way.

Evan: Okay, last question here, um, what do you believe will be true about technology's future impact on the world that most people would disagree with, or maybe most people consider to be science fiction? 

Mike: I think humans will live longer as a result, and I don't think we're necessarily going to draw the connection.

I think that we will, um, just in the same way that technology, like, and when I say technology, I mean computers. I mean, like, you know, I'm wearing this, uh, these, like, kinesiology tape right now on my foot. Like that's a technology that's improving my quality of life, right? Like there's a lot of little ways that are going to improve our life with artificial intelligence that will extend human life.

I mean, I think we, we have, we won't probably think about the fact that that's what happened, right? But it will be, and it won't get the attribution it deserves. People love the science fiction, like, Oh, yeah, it's the devil, you know, but, uh, it's really not. And I think that's going to be the little ways that we almost don't notice that are going to have this tremendous impact that the technology probably wouldn't even get credit for.

That's not even technology. It's not high tech, it's just the way we live and the way we help humans. 

Evan: Mike, thank you so much for taking time to join with us. Looking forward to chatting with you again soon. 

Mike: Thank you very much. Great. Thanks for having me.

Evan: That was Mike Hamilton, Chief Information Officer at Cloudflare.

‍Saam: Thanks for listening to the Enterprise Software Innovators podcast. I’m Saam Motamedi, a general partner at Greylock Partners.

‍Evan: 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 enterprisesoftware.blog.

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