Cloudflare TV

ℹ️ CIO Week: Fireside Chat with Juan Rodriguez

Presented by Annika Garbers, Juan Rodriguez
Originally aired on 

In this special CIO Week session, join Cloudflare Product Manager Annika Garbers for a fireside chat with Juan Rodriguez, Cloudflare's Chief Information Officer.

As CIO of Cloudflare, Juan is responsible for safeguarding large swaths of Cloudflare's team, while ensuring they can continue to innovate and deliver best-in-class products to Cloudflare's customers. Tune in to learn about Cloudflare's IT journey, and how we've built Cloudflare One to serve our own needs — and those of our customers.

Visit the CIO Week Hub for every announcement and CFTV episode — check back all week for more!

CIO Week

Transcript (Beta)

Hello everyone. Welcome to Cloudflare TV and welcome to CIO Week. My name is Anika.

I'm on the product team here at Cloudflare and I'm so excited to be kicking off Cloudflare last innovation week of the year, which we're spending highlighting new products and features of the Cloudflare One platform that are going to help CIOs build their next generation networks on us.

And I'm super excited for this segment to be joined by a featured guest for this week, our amazing CIO here at Cloudflare One.

Juan, thanks so much for joining me.

Do you mind introducing yourself to the audience?

Tell us a little bit about who you are, what you do at Cloudflare.


Thank you for having me, Anika. This is very, very exciting.

I was thinking on Sunday that, you know, how how amazing it is to basically be working in a team and in a place like Cloudflare Workers, like helping shape the future of a lot of the products and services that people that have jobs in the mine, like mine are going to be using in the future to modernize their company.

So, yes, my name is Juan Rodriguez, I'm Cloudflare's CIO.

And CIOs or Chief Information Officers in different companies mean different things, depending on the industry you can have like a different roles or a scope of responsibilities and things like that.

So in Cloudflare, specifically, I am responsible in general for everything that has to do with Cloudflare's infrastructure and systems that help Cloudflare run as a business.

So all the corporate systems, accounting, payroll, our CRM, our HR systems, all sorts of things like that, then all the corporate infrastructure networks in offices, endpoints, laptops, collaboration, tooling like Zoom or our email system and everything else that we use basically to collaborate as a team.

And everything that also has to do with providing services that bridge the products that we sell to customers and our internal infrastructures of services like billing entitlements, things like our marketing engineering team that builds the, the house build the platform that powers the website, Trust and Safety Engineering helps provide a safe and secure services for customers.

So a whole bunch of things like that.

And then also, as I always say, I'm like, Cloudflare's number one customer as well.

What I mean by number of customers, like I'm normally the guy that tends to kick the tires and everything that that we that we launch for customers.

So, yeah, that's in a nutshell what my role is like.

That's awesome.

Yeah, I think it's fantastic. Also from the product perspective, to be able to work with you and your team so closely, to really have like, not even customer one, customer zero, right?

Like a lot of the time the ideas for the things that we're building here come out of your team where you're like, We're frustrated by this or we're having this challenge.

What can we build to make this easier? And I think that's a really great just sort of impetus for a lot of the innovation that happens on the product side.

So that's awesome.

So you're a CIO at Cloudflare now, what did you do before Cloudflare?

Like, how does one become a CIO? What's the sort of journey that led you here?


So I have what I would say a little bit of an unconventional path into into being a CIO, even like being an I.T.


So I don't consider myself an I.T. person.

When people ask me, I was like, I'm a software executive. I've worked in software companies all my career.

And I started basically having as an intern in Hewlett-Packard many years ago.

And I used to help manage the demo center that we had in HP Spain.

That's where I came from.

And in there we provided hardware was very expensive.

It was all these big expensive UNIX boxes.

HP provided all this in the demo center and then software companies came to install ERP system.

So CAD systems, all sorts of software into this these platforms to do demos for customers.

And the hope was they like the demo, basically they'll buy the software in running in HP Hardware, right and all of this stuff.

And from there I actually got hired by one of the partners that is the software.

They did ERP systems and I was an installation engineer.

I used to basically work with customers deploying the ERP that is going to have, designing basically the technical infrastructure to run the ERP, do a lot of database installations, optimizations, performance tuning, things like that.

And from there I actually moved to working in the product engineering team.

I used to run for a time, an engineering team that basically did data access many things like Oracle and SQL Server and Sybase and a whole bunch of different platforms.

I also ran what we called Configuration Management. And from there I actually did a little bit of stint on product management for, for a while, for a few years.

And I also ran, for a period of time, basically in our company as well, their technical consulting services team, right?

All those folks that actually want to install products on our customers.

And eventually, I think when I was in product management, the CEO of the company, this guy that's a good friend of mine, he came one time to ask me and says, I would really like you to take over the IT department.

And I'm like, What are you talking about?

I'm in product management, having too much fun building products.

I don't want to do that.


What's going on? So I said no the first time, and he's like, but you know, he said, 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.

Very command and control.

And I need somebody basically I know small business runs and run it like basically a technology company.

So I said no, he hired a person who didn't last too long.

I think it was like nine or ten months.

And then ten months later he came again.

He said, Juan, I'm not asking you, I'm telling you, you're taking over.

And that's how I started, basically my journey on running I.T.

in a software company.

And I then left after a couple of years to, you know, to take over a larger team here in North America.

In another software company called Sage, I was the CIO for North America, and I did that for a while.

I moved to Europe also to run it in Europe, and eventually I ended up going back to the organization to actually run all the SRE teams and a lot of services instead of, say, all the cloud services.

Everything that we did like with services that we're running in public cloud, all the teams that manage all that and then a number of also engineering teams that provided a lot of glue for products, things like, you know, some of the things that I mentioned, things like identity, entitlement and things of that.

And I was a Cloudflare customer at the time.

I started being a customer around 2014, 2016, and eventually I ended up, you know, having a talk with the team here.

And Cloudflare I ended up joining around January of 2020.

And I think that one of the things that help me learn here is, you know, Cloudflare is a very engineering driven organization.

And having somebody basically in a role like mine instead of a software engineering team I think is very helpful when you understand very well how those engineering teams basically like to work.

You know, you cannot tell, like software engineers know because they're going to say they're going to do it anyway.

So, you know, you've got to work in much more collaboration and, and, and fashion And yeah, So I ended up here as the first CIO, having to set up a whole function and it's been almost three years and it's been a ton of fun so far.

So that's a little bit of my journey in about 3 minutes.

That's awesome.

Yeah. I was curious to learn a little bit more about that too, that aspect of so much of your background being in product and engineering and software.

I mean, I think a thing that's maybe unique about your job versus other CIOs is that you have engineering organizations that report directly to you, and in some ways those kind of feed the activities that are happening in it.

But could you talk a little bit more about that?

Like how does your background in software in general and working at Cloudflare, obviously is a software company, inform the way that you think about IT systems and how we can support engineers and then also the rest of the organization too and sort of new ways.


So I think that in IT, over time, especially in a technology company.

But I think across the across, in general, across the whole IT industry, it's been more necessary basically to have actually IT engineering teams that are building also services and products basically make it more like the company is the customer that they're using.

So in the past you may have like a monolithic old system that basically will run your whole enterprise, soup to nuts.


And you will have basically, you know, running in a mainframe or running in a big system with a big database on run of the functions.

Nowadays, you know, normally you get IT architectures that are much more best of breed, right?

Where you have many different systems that are glued together.

So some kind of enterprise service bias or integration and to do that and basically run that stuff successfully when you have like a lot of highly distributed sort of systems landscape, you need to build software for that.

You need to understand a lot about like basically data integration, data patterns.

So in most companies that is, from an IT perspective, very necessary.

You cannot just like in many cases, just run things or buy things out of the street and help them they run.


The other thing that I'll say, what happens is, you know, in a company like Cloudflare, where they were like very engineering driven, many things that we do split around our software, our control plane and things, the things that we build, And it's not something that comes with with that connector to some building system or some deployment system or provisioning system.

So you need to build all that glue and all those services that come together.

So in fact, one of the things that I that I did is I created this a function called enterprise engineering.

And what we did basically is like they were like a number of services that were run within the main engineering organization and things that were like spread out around the company.

And we brought them together inside of the dysfunction.

So I think that in general, if you are in an IT team that doesn't have any kind of software engineering capabilities, you're going to be heavily limited in the amount of change or the amount of innovation that you're going to be doing as a CIO or as a professional.

So I think it's like one of those things.

I mean, a technology company is much more prevalent, but I think everywhere.

So that I think that is something that just becomes table stakes.

Yeah, absolutely.

That makes a ton of sense.

So we talked about this a little bit at the beginning, but you being customer zero for Cloudflare Solutions, I wonder if you could maybe peel back the curtain a little bit for our audience and talk more about what that experience has been like.

Like what are some examples of rolling out products that maybe started as Cloudflare built for Cloudflare.

And now we productize to help other CIOs solve problems.

But initially you were sort of that first customer kicking the tires.



And so many of the products that and you obviously know this because we work in product management, many of the products that we sell, they started as something that we developed internally to solve an annoyance or a problem that we have.


So a very typical example is what we did with what is called for access that now we call for teams we had we have engineers in many, many places around the world and accessing whether it is like zero confluence or all these things that we use basically to develop software over VPN was extremely clunky, nobody liked it, everybody hated it and performance was bad.

So internally, because we have like this incredible edge network and services we provide is like, what about if we could come up with something that was much more high performance than a traditional VPN that you're like connecting through a concentrator that may be far away from the user know we could do something, develop something in the Cloudflare edge much closer to the to the end user that would provide much better performance, but also a much better experience.

Right, in terms of connectivity and things like that for our engineers.

And that's how we started really.

It was a problem that we had internally, something that was like very annoying and, and we developed Cloudflare access and then we deployed in We started using it internally.

We launch it, we productize it for customers and internally.

Sometimes one of the things that I always say, we're not exactly a company like our typical customer.

As I said, we tend to be a little bit more on the bleeding edge of things than our typical customer, right?

So the things that sometimes we have to do in these products, they have like advanced capabilities that from a business point of view, a market point of view.

You know, they may still, they may be a little bit like, as I said, on the bleeding edge of things.

So that's an example.

You know, another one that we deployed also internally as Customer Zero is being our workplan or a client and all the computers and how that has helped us develop a much better product for our customers.

So we have tested Browser Isolation, help us to perform as we traveled.

We use like a lot of Mac computers, which is not the typical thing that a lot of our customers use.

But it helps us with the feedback that I provide or our teams provide everything what we call dog food and ride find bugs or find issues or just tuning things so our customers don't don't find them when they start deploying.

And that tends to be a significant advantage between my team and Joe's, our CSO, team.

We also provide the customer zero capability that you just mentioned, but we also help a lot of the teams internally with features, like what wouldn't it be great if we could do this right, you know, to help with deployment of this or manageability or, you know, things that are scale, right when a customer.

So that's one of the things that I enjoy the most because of my background as a software professional that even when managing or taking care of the IT corner, I'm still able, I feel that I am part of the software development process, you know, influencing basically direction of the product or capabilities and then hopefully always always test their right first.

So it's a lot of fun.

Yeah, absolutely.

And I have perspective on this personally as an employee that used to have to use the VPN and now I don't anymore.

Everything's through access.

But I'm curious about just like, how has it been going?

So you started at Cloudflare.

You know, it's been almost two years.

We've done sort of these rollouts of these products to help really transform fundamentally the way that people get work done here.

Can you just talk about like how that's changed the game for your team and what kinds of things is your team thinking about and working on now that maybe they didn't have the time or capacity to before because of managing the VPN and complaints and frustration around that?

Yeah, I think that what probably I mean, I started right before the pandemic, right.

And you know, I spenT 11 years in my previous company.

I never thought that I was going to basically have to board an entire new company, you know, take over like a whole department in the middle of a pandemic, you know, having to do this remotely.

I think what the past two years, what it has done is accelerate tremendously the pace at what we have to deploy a lot of these solutions.

So Cloudflare was primarily, you know, very much an office culture, right?

We didn't have a lot of remote employees.

We had some, but not that many.

And we were centered around basically, you know, hubs, right?

Whether it was San Francisco, Austin or London or Lisbon or Singapore, those are probably the main ones that we have.

And then suddenly and we still use like a very much a zero trust architecture.

So if you're like in a Cloudflare office, I always say, you know, people chuckle about it as well.

From an access perspective, it's almost like a glorified Starbucks, you know, probably a little bit more robust networking.

But, you know, we don't have a trusted network inside of an office that give you access and resources.

You still have to go basically through Cloudflare for Teams and everything else.

So but what happened basically with this, you know, with the pandemic, we're having to send everybody to work from home while all that infrastructure that we have basically to to work remotely like with access and teams became very handy.

We didn't have a problem that many companies had around having to add capacity to their VPN, suddenly having to support all these users.

What it did is basically that our quote unquote edge, from an endpoint security perspective became the employees' homes and many things that normally when you're working primarily in the office we have to worry about because we have firewalls in the offices and there was like protections in we suddenly having to take control basically a much more management of that endpoint through teams or and become much more critical.

So Joe, myself and our teams, we had to basically work with the with our product teams to help us with a lot of more capabilities that we needed to be able to deploy those teams, agents and employees, in employees and endpoints to be able to better manage whether it was like DNS access security, URL filtering for things like, for instance, heartbeats.

From an authentication perspective, it's something that we also needed to accelerate tremendously to be able to provide a much stronger security posture from, you know, from people working from home, primarily in this type of environment.

So that's one of the things that I think that in many cases, those are things that we had on the list, on the roadmap, things to do, you know, from an IT organization or a security organization and as a product team.

But as I said, you know, the pandemic just basically went and said, you know, hold my beer and just compress up basically from like a year and a half to a six.


You think you have two years to do this? Actually you have.

I don't think so. Figure it out.

Yeah. So...

So that's probably one of the big differences that we've had to do with our Internet, and then other things like, to help facilitate for our teams, you know, better capability.

So working remotely through collaboration tools in remote whiteboards be able to do much more things, you know, asynchronous or remote fashion that what you will be able to do if you're in the office with a whiteboard and things of that.

You know, over the next probably year and two years, you know, the things that then we're focusing on is since this is sort of the new normal, clearly, you know, it's become pretty apparent that hybrid is is we're going to be, what I think the vast majority in the industry is.

How do you facilitate in this construct of some people working in an office or visiting offices in a period of time and and also people working from home is facilitate teams being able to visit offices, you know, booking this things for for, for what we call on site off sites.

You know, that's basically what we see our offices become in places where teams get together, you know, on a occasion to do work.

I'll be able to facilitate that process for our companies in a in a for our employees in a in a fairly seamless manner.


So we're right now in the middle of looking at software, things that we may have to build ourselves, or partner with some company, so how can we provide infrastructure to the employees to be able to do things like that?

As I said, you know, in a way that feels very, very Cloudflare.

And we also are looking at things like that are a little bit more also innovative, right, where we're launching, we're building some software for we don't believe we want to be able to support our communities around our offices and how we can provide almost like a virtual car to our employees that they're able to use for lunch, lunch around in cafes and lunch places around offices.

And they get a benefit out of that instead of having to build a cafeteria, for instance, in a central office.

So we want to make sure that we're supporting.

So these are some of the things that right now are from a more strategic point of view, you know, occupying my time on, as I said, you know, what is that employee experience that we're providing across the board in this new hybrid construct for for our employees?

Yeah, I think there's a lot to be really, really excited about, right?

I mean, obviously, all of this is really challenging and you're figuring out just how to navigate totally unknown territory with these new forms of work.

But I think the opportunity for new kinds of collaboration, for more diverse and inclusive workplaces, because we can, it's more easy to hear from people that have diverse perspectives because we can chip in with people from around the world like there's so much possibility here.

And that's super exciting.

I'm curious like if you have a couple of other maybe initiatives in mind or just like themes in general or things you think maybe other CEOs are thinking about, like what gets you really excited when you wake up in the morning to do your job?

And what are you thinking about sort of long term?

That's cool for Cloudflare and you see as opportunities for us to embrace new ways of working.


So these things that I mentioned around the hybrid workplace and how people do work in that efficiently, in that, in that construct, is something that is very exciting to me.

And the thing that is very interesting about it is like, I'm originally from Spain, is that while from a company perspective, you want to provide an environment that in certain principles, if you want to call it that way, you know, certain things are very much a cultural and local aspect to certain things, right?

So how, you know, sort of interactions or some of these maybe like for instance in Europe in certain countries is different.

You know, for instance, when we've been in North America.

So how do you, when you're thinking about putting these things that I mentioned in place around hybrid workplace and collaboration frameworks of booking and things of that.

But apart from just like the technical parts of things, how do you also take into account some of the things that you mentioned around, you know, looking at that basically diversity lens and diversity of locations, diversity of cultures, diversity of backgrounds, how do you apply that lens also?

So what you're building feels inclusive.

You know, it's not like, oh, wow, you know, this is clearly something built by Americans for Americans.

But here in country X, you know, this doesn't make any sense.


So I think that is something that is very, very interesting.

The other part is, it continues to be, it's like how we can provide a series of tooling and frameworks basically for teams.

And that's going to be a little bit different depending on the on the on the team.

Is that where regardless of where they're working, whether they're working today in an office where they're working in a, from home, or a mix of both and teams.

The team may have like a little bit of a different construct.

Some people maybe come in to the office two or three days a week.

Some of the people, you know, maybe are fully remote.

How do you provide basically tooling and glue that they can still basically feel like a cohesive team, almost like if it were like all just sitting one by another.

And I think that there is still a lot of innovation that to come out of this area.

I think that we're still scratching the surface a little bit with some of the tooling that we have today, you know, whether it is the typical collaboration platforms that you can do.

But I think that thinking more from a from a use case perspective, you know, how product management may work or engineering teams, sales teams, you know, so it's going to be a little probably a little bit different and associated with the specific workflows, how we can build, you know, certain software and services basically to facilitate them having that experience like it that we're all working to together.

And the thing that is exciting about Cloudflare is like, this is one if you can think of a place where building some of these things will be happening, will be will be possible, will be in a place like my Cloudflare And I'm actually looking very much forward to, to build in some of the, some of that stuff here with the with the rest of the team.


I love that there's so much to be excited about long term and also super near term.

If you are watching this, today is just the beginning. There's going to be so many exciting announcements coming up through the rest of this week, announcements for one, and people like Juan in the world to help build next generation networks on top of Cloudflare one.

Thank you so much for making the time for this.

Thank you for all of your work and collaboration with the product team.

I really, really, really enjoy having the opportunity to work for you, work with you, you.

So yeah. Happy Juan week.

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