Cloudflare TV

ℹ️ Fireside Chat with Juan Rodriguez Estevez

Presented by Juan Rodriguez, Corey Mahan
Originally aired on 

Welcome to Cloudflare CIO Week 2023!

This CIO Week we’ll demonstrate how Cloudflare is helping CIOs keep data, devices and employees both safe and fast across hybrid and remote environments. We’ll show how Cloudflare accelerates digital transformation and modernizes networking and security towards a Zero Trust model.

In this episode, tune in for a conversation with Cloudflare's CIO Juan Rodriguez, and Corey Mahan.

Tune in all week for more news, announcements, and thought-provoking discussions!

For more, don't miss the Cloudflare CIO Week Hub

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Transcript (Beta)

Hello and welcome back to another episode of Cloudflare TV, the CIO Week Edition. We're super, super excited to have you joining today and I am honored to be joined by our own Cloudflare CIO, Juan Rodrigues, who will talk a little bit more about his path, how he ended up at Cloudflare and his industry insights through our conversation today.

But before we jump into that and I introduce Juan further, I wanted to quickly just give a backdrop on CIO Week why we do this and what the themes for this week are mostly three fold one around how we enable the simplest, fastest path to Zero Trust something I'm sure we'll talk about here in just a minute to how we collaborate with the right partners, making sure that if you want to go far, go together, who and what to work with, and how those Cloudflare Services work better with them.

And then three, lastly, how to organize and streamline your multi-cloud strategy, right?

Cloudflare is the global control plan, that fabric that connects everything together.

So with that out of the way, as I mentioned, joined by Juan, welcome to CRTV.

Thank you, Corey.

Thank you for having me here. It's very, very CIO Week is always very exciting for me.

We call it Internet Search one week, so it's a lot of fun.

And thank you for allowing me to participate on this call for TV chat.


Well, we'll kind of jumping right into it. Speaking of being the CIO at Cloudflare, when did you join Cloudflare Tunnel?

Let's talk a little bit about your journey of how you've arrived as CIO at Cloudflare firstly.

Yeah, so I joined in January 2020, which as we all know, 2020 was an interesting year for everybody.

So I changed companies and I started covering January and I had no idea that I was going to be starting in a new company, right.

Two months before the pandemic.

So I'll talk a little bit about that.

But let me let me tell you a little bit about how I got here.


I am originally from Spain and I grew up in Spain and from I'm one of those blessed people that I think computer science and computers and programing and things like that has always been a little bit of a hobby of mine and in general technology.

In high school, I was one of those that basically was like buried a lot in the in the computer lab that we have that we have in high school.

And what a lot of people don't know is that my other passion is or at the time was potentially, I almost went into the Spanish Navy, you know, basically to be an officer.

So my father was a career officer and that was something that was very drawn to me.

And I remember my father having the chatter, like when I was 17 or 18, you know, trying to figure out what I was going to do.

I was going to the office of school.

I was going to study something in computer science.

I'm like, well, you know how it is.

And maybe you work a lot terribly.

And then the other problem is that you have a big mouth, so you're going to be in trouble a lot.

So you know what I consider going into, you know, studying computer science and stuff.

And that's how I went there and I started my professional career.

I was an intern in Hewlett-Packard and and always and so forth.

So that's the other thing that is very I'm I'm a I'm a software person, right?

So my first job was managing the demo environment that HP had at the time in Spain, the demo lab.

And that's the time where, like highways took us the money.

We have like big, big UNIX machines and we HP had this tremendous facilities and that will make available those servers and those rooms do software companies to come do demos for a competitive ERP.

So CAD systems, so databases and things like that.

And the hope is basically they will come in and for free.

We didn't charge them any money and the hope is that they will come in, and people like demos and all those things, they will be able to buy like basically that software on HP or HP hardware.


And from there I went to one of the partners with HP. From several perspective, the CRP software company asked me if I would join them and I would and I they were getting into the Xbox world and I went to work for them basically at the time doing installations and technical designs and things of that particular episode were in fairly large customers.


Learn a lot about databases and Oracle at the time know for I'm sewing my H a little bit sideways and all those things that today you know many of them don't exist.

And from there I moved to the US in, in 1999. I was working with a for a guy that was here in the in the in Atlanta and he has been moved in and I moved and I became basically I joined the.

The engineering team of the company.

And at the time I was working basically in what is called configuration management.

Basically it's the team that has like today think in modern lingo is like all the CICB pipelines, right?

Almost like dev tools.

And we manage all these build environments and all these Unix platforms.

So when those platforms open, it's a lot of fun.

And then I actually move from there to do more development work.

And in the end we're running some of the development teams in, in the data access layer of the product basically that we're that we're building and we got installed in that company eventually.

The other things I did like product management, I ran technical consulting teams.

Eventually, you know, I got asked to see if I wanted to run basically at that company.

And I would ask my CEO, which is the guy that actually moved me here from Spain to the US.

And I he became our CEO.

And I said, why are you asking me to take over this?

I worked in product management and I'm like, well, I'm tired of hiring people that want to run i.t.

In a software company like this was a bank or a manufacturing company, things like that.

And you know, as you know, the basically last like 9 to 12 months and then I end up getting rid of them because this is not a Bancor think it's very different.

And so, so the first time that I got, as I said, no. And he had another person.

He I think last said basically nine months.

And then he came again and said, I'm not asking you again.

I'm telling you, you're taking over.

And that's how I started basically doing it in software companies is primarily because I knew how to run.

I came more from the engineering and product side of the house, and I had a pretty good knowledge of what those things, which is something special, if you want to call it that way, that's going to say in many industries you don't need it.

Eventually I went to another company called Sage to be the CIO in North America.

I moved to Europe to also be the CIO for also all of Europe and North America together.

And at that time 2013 and 2014. Sage was a very distributed company.

We acquire a lot of companies and we had like a lot of services and we're moving into cloud, a lot of services that run locally.

And I had a team that was centrally managed that was supposed to manage operations basically for all of those services.

And what was I looking for at the time, around 2015 or 2015 was like, I need a wife and wife, that it is essential and in the cloud.

So I don't have to have UAVs in all these countries and, you know, copy configuration.

Is there a way that I can have like almost like a central control plane that I can put in front of all this loyal service?

And it was this little company called Cloudflare that was just starting, right?

I mean, they had like some C and stuff, you know, they were like getting into the cloud, into the waform and other things.

And we started using it like, okay, well, let's get it.

You know, I think that's one of the beauties of being a CIO in a technology company, you can make bets on things that are a little bit more leading edge show, Bleeding Edge and see how they pan out.


And that was one of the best that I think I made on that multiplayer at the time was like relatively small compared with other more established players in the market and I think pan out right.

And we ended up using the heck out of Cloudflare for many things in spades.

And today is still a fairly large customer and eventually around 2019 it was like becoming a public company and, and they were looking for a CIO.

I mean, there was, you know, the interesting things when you become a public company from a systems and technology perspective and things that you need to do for compliance, protecting all that stuff.

And that's how we ended up talking, right?

I knew somebody that had a relative that worked in Cloudflare and I got an introduction and I didn't know exactly what they were looking for.

I don't know if I was going to be a fit or not.

We talk and it's like.

You know, interesting background.

You know, a guy that basically is like a super guy in an Cloudflare is very engineering company, and that's how he ended up basically joining into it.

And it's been like an interesting, obviously journey over the past.

Three years getting onboarded in the pandemic and having to manage through all that and all those things.

But here we are three years later in 2023, and that's how I ended up.

I ended up here a little bit in 5 minutes.

Yeah, no, a fascinating background one.

And I can see the background that you had and the education, the desire that you had play out.

Like you've done the things right, you've had hands on, you've applied them.

And I also love the I think a lot of people actually would probably have a similar version of that story of yeah, I use Cloudflare for WAAF or CDN or Zero Trust and then you'll talk to peers of like, Oh yeah, that's how I'm here because I love the products and use them myself.

And then we wind up on calls exactly like this, which is, which is pretty cool.

One kind of jumping a little bit ahead to you, the background of how you've arrived, you've made it, and we'll talk a little bit about the transformation, let's call it that you had to lead through during the pandemic.

But right now, before we go into what you do and what you've done as CIO, what do you love the most?

So you've gone through that journey.

You've arrived at Cloudflare.

What do you love most about being Cloudflare CIO?

Yeah, so I think this there's a couple of interesting things.

One is more generic and another one is like a little bit more about specifically is like one of the things that I love about ideal business technology teams, in companies, is like if you play well you know and you're affecting what you do you have the fingers in the pie of everything that's going on in the company.

You know if today basically is very difficult to run a company with our systems and technology and automation and things of that nature sky the lifeblood.

So you are in the center of everything, right?

That goes that goes wrong from all the different departments.

Write a chart, product, sales, finance, marketing, a lot of different things.

So that is very exciting, right?

A lot of fun.

You know, a lot of these departments basically, you know, they are especially, but the role of an organization in general, you are successful if by making everybody else successful.

And that's something that is interesting to think about.

So that is very exciting.

Again, if you like to not be bored and have an interest in for all these things basically that everybody else.

So that is in general is something that I find pretty interesting and fascinating about working in this area of business technology.

What is interesting about proliferating itself obviously the company is exciting, right?

I mean, as a software professional, being in a company that where we have a strong mission and that you can feel your impact every day by building a better Internet and especially, you know, the last three years with the pandemic were like, really, the Internet was the superhero sidekick, you know, to humanity.


As I say, it's been it's been pretty, pretty exciting. But to me, you know, the ability to basically.

While I have a basic point of view, but I work a lot with our product teams because their customers, you know, normally I like somebody like me or somebody my team.

So I get to play product manager, I get to try things. I get to be very involved.

In many cases, you know, sometimes it's like because I'm trying things internally and we deploy most of the products that we use internally before.

But also just like from a curiosity perspective, it's like, Hey, can we pick your brain about this?

Will this resonate?

Will this not resonate is something that our customers will be able to take advantage of.

So that is a lot of fun because I get to play a little bit of product manager once in a while.

You know, if the product lets me.

That's awesome.

And I can attest to that on the public record that this is true. You know, we work with one team very closely in the product door to make sure that this meets the needs of our own in real, real life testing, if you will.

It is in a lab somewhere.

This is making sure that we're securing and protecting and accelerating all the connections that we manage.

So super, super here to cool to cool to hear from from your side as well.

One, we've talking a little bit about being the CIO in at Cloudflare, but maybe for taking a step back to as chief information officer, what is it like but not, not necessarily in the day in the life, but what are your major responsibilities?

You kind of talk about having hands in all the pies and making other successful.

What does that look like for you and kind of where your responsibilities lie for those kind of watching them?

Well, yeah, I've heard CIOs, we have a CIO, but I've never really talked to one.

Yeah, so it's a very interesting question because CIO as a job, it's a little bit like another role called the CEO where like depending on the company in the industry can mean different things and have different responsibilities.

So CIO for instance, in non-technology companies. They normally have an area of responsibility that is sometime between like systems and product engineering.


In terms of for instance, in a bank, you know, we are responsible for the online platforms that the customers basically do the banking with and things that they normally have.

Like, you know, a lot of those things, which is like different than normally, for instance, a technology company, a software company like us, that tends to be a little bit more specialized because their product that we sell is actually the software itself.

So it has to be, you know, normally it's like a CTO that is responsible for those things and then a CIO like me that is responsible for internal.

So the way that normally I would explain it is the CIO Cloudflare normally in technology companies is responsible for systems and technology infrastructure that make Cloudflare in this case run as a business, right, versus the product and technologies that make that make Cloudflare the service provider to their customers.

Right? So and that's like so things that make Cloudflare run as a business versus things that basically make a service provider to the customer.

So in, in, in traffic, I have responsibility for everything around business technology.

So endpoints and laptops and phones and all those things that we that we give to employees to be able to work from everywhere, everything that is like basic technology, the seen in offices or wi fi and all those sort of things, collaboration suites, you know, that lets us do these wonderful things like TV with, with Zoom or, you know, or our email environment, collaboration environments and all those things.

And then I'm also responsible for basically all the systems that make, as I said, Cloudflare One, so sales systems, HR systems, finance systems and all the gluon integrations, basically that make data flow between those things.

And then I have an also another area of responsibility.

You know, I have a fairly large engineering team where we build services that normally sit in the middle of the product that we sell and the systems that basically in the business run.

So things like billing, provisioning, entitlements, things like that.

So when customers buy the product, we build them, but we also are able to tell the product, say, hey, you know, Customer X bought this with these characteristics, you know, provision that so they can use it and we're able to recover that.

And then I have like all the services that are run.

So for instance in, in, in Cloudflare One also I have responsibility for trust and safety engineering.

So, you know, all the services that our trust teams uses marketing, engineering, so building the websites and pipelines and marketing systems and a couple of other services like that.

But broadly, that is what I what I have the over the past three years, probably what we miss most focus on.

We've been in an area of very high growth in.

One of the things that I talked about also is the fact that we went public basically in late 2019.


As a public company, and I've always worked in public in public companies. There's many requirements from a systems perspective that have to comply.

I mean, in the US, we have this law called Sarbanes–Oxley.

Financial records and things like that on systems and systems control and change management and all those sort of things.

You have a key, you know, basically a role to play and being compliant with basically with Sarbanes Oxley.

So, a lot of the things that we're trying to put in place over the first month is a lot of things like that around governance, you know, to comply basically with, being a public company.

Then the other thing is it basically has been like all about is scalability, right?

Many things when you're a smaller company, you have like a limited set of customers and employees.

You know, you can deal with more manual processes, but as you grow automation and be able to deal with all those things without having to throw like armies of people at the problem and things like that is very.

So we have done a lot of work in basically building automation, implementing new platforms and systems that lets us expand to new markets and new companies.

And we have invested a Tony in basically automation of things to be able to onboard employees more efficiently or more customers more efficiently and frictionless and say and then just like just provide automation around key business processes.


And we continue to basically in our role to $5 billion to try to take a look at what you know, what that is going to take.

And one of the things that is important to understand with systems and processes is.

You know, if you're implementing something normally three months before you need them, you're going to you're going to lose, right?

Normally, certain systems and platforms and companies, you know, it may take you like one and a half years to years, two to implement them, you know, deal with a change internally, too.

So in many cases you have to start pretty early and be able to see around corners for the actually the company is going to need something.

But your statement of hand, center and hands in all the pies I think is exactly right.

And kind of all the things of flowing through being a lifeblood of systems and services that are used within the company.

I think that's exactly right.

One thing I want to touch on and kind of wrap up the segment with, as you said, kind of looking around the corner is around industry insights or things that you think about the future of the CIO for your CIO is out there.

You know, what do you think that will be the current trends and challenges that you'll be thinking about kind of looking forward for the next few years?

Yeah so right now I mean it teams and security teams in general they are in a little bit of a bind.

Right. I mean the economy backdrop for everybody, right.

Is very challenging right now.

And, you know, this sort of time is normally is shrinking budgets.


And the thing that is that that makes it tricky is as a CIO and as an IBM security team is like.

The certain things that you cannot stop doing, because if not, you mortgage the company right for the future.

Things like security, key investments for things that if you just like reduce everything, basically you're going to be in a world of hurt when we get out of this environment, which we will probably sometime over the next over the next year or so.

So there's this balancing act that it teams today have to do on how to keep basic a lot of those key investments around security innovation.

Some of these projects that I mentioned are like growth and entrepreneurship, but at the same time being able to find efficiencies within the budgets in the companies basically to continue to fund those things.


So this is a time basically where like a lot of consolidation of vendors will happen, try to make a strategic deals with your partners that provide you efficiencies on the short term, but also allow you to continue basically investing for the future and and all those sort of things then.

And that is not easy in many cases.


So, you know, people like me become master negotiators, you know, apart from like basically doing your day to day job.

Final thing that it's going to continue to basically be very important for it teams is how in this hybrid environment that is more of the norm know the new normal post-COVID is how do you continue to provide tools and processes and capabilities.

Basically the teams to be as efficient as they can in this in this hybrid environment, right?

So before companies optimize a little bit for their culture and the culture, normally we're in two camps, right?

Is like you would like either like an in-office culture and if you are an in-office culture and you are remote, you are kind of like a little Tulsa, right?

You are like almost like a second class citizen and vice versa, right?

If you wanted to work in the office and you like a lot of people, but the company culture was remote, that worked great.

So, now we have to optimize for both.

I get a little bit of best of both worlds and that has tooling implications, but also with it means to be able to provide help to business team with their processes and work with HR.

And work with like management and things like that to be able to help how to maximize the use of this, to be able to provide basically most productive results and be able to provide insights on the team areas where they may be able to optimize.

And the third one it goes a little bit like with this hybrid environment is because a lot of that security has moved now basically to the new edge, if you want to call it that way.

It's almost like the employee endpoint and by extension, because we're like most of us working hybrid, that becomes like a house or where that employee is working is how with zero trust tools or activity tools and things like that, we are able to, while providing an excellent experience, be able to properly manage and secure those endpoints that the employees the laptop that was one of the things that is, I mentioned this in a in a tweet that security is also a difficult act.

I mean most of the time if you are improving security, it's going to have some effect, especially when you're messing with devices on friction or employee experience.

So it could be performance, it could be friction, it could be something.

And I think like finding good tooling that lets you have your cake and eat it to improve the experience, make it a more transparent, frictionless, but at the same time being able to improve that the security basically that now extended perimeter is is going to be important.

And this is something that obviously in Cloudflare we're very passionate about and we're investing a lot in all of this to keep our customers, you know, allow our customers to see the people, their employees and the data and their customers as well.

So there's like three things I said, like be able to be a master negotiator and be able to stretch your values as much as possible.

So not to mortgage the future, but creating capacity in the in the short term be able to provide tooling and coupled processes, you know, for teams to be productive in this hybrid environment.

The third one is these investments basically and start if you haven't yet on investing on best in class tooling to secure more of that extend the perimeter without sacrificing employee experience.

In some cases if you and you can improve it so you can have your cake and eat it too.

It's more about those are very much top of mind I think. Awesome super insightful one and I like the fingers in all the pies and have your cake and eat it too.

And we'll have to. We'll get a snack after this.

But those analogies, I like pie.

I like pie.

So I got another perfect go. Those are spot on.

And it's kind of we wrap up here. I want to thank you personally for sharing your journey and how you ended up at Cloudflare and kind of more inside of what a day to day looks like for you as well as the insights and what's what's to come for other CIOs.

So thank you very, very much for joining me today and for the rest of the CIO weeks one week, as we continue with a bunch of exciting announcements for those watching that are curious about what we've announced and are, we'll continue to announce.

Stay tuned at Cloudflare Calls Backslash CIO Dash Week. All the announcement blog posts will be put there as a centralized hub.

You can follow us on all of the social media channels as well, or check out the Cloudflare blog directly for what's latest to come.

We'll conclude now that I just want to thank you again, one for joining you today and we'll have more to come for CIO Week.

Thank you, Corey.

Have a good one. Bye bye.

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