Cloudflare TV

Logins: The Last 4 of Your SSN

Presented by Sam Rhea, Juan Rodriguez, Alissa Starzak
Originally aired on 

Sam Rhea hosts a casual fireside chat with Cloudflare's Juan Rodriguez and Alissa Starzak to learn how their careers got started — and where their newfound access took them.


Transcript (Beta)

Welcome everyone. Welcome to Logins. Logins is a show on Cloudflare TV where we have guests on to tell us about the start to their career journeys.

And this is really fun because these are the types of conversations that were not for Cloudflare TV I would really want to have.

This is really exciting for me as a guest of this show as well to get to hear from people that I really respect and really admire and they're really wonderful team members here at Cloudflare.

And today just like last week we have two really exciting guests from the Cloudflare team.

If you remember last week we had Emily Hancock and Carrie Linder who shared their journeys.

Emily from the DMV to being responsible for data and security at Cloudflare and Carrie her journey combining computer science and psychology and research into design here at Cloudflare.

And today I'm so excited for the two guests we have on.

Alissa Starzak, head of public policy at Cloudflare and Juan Rodriguez our CIO.

And this is before the show started airing we were already enjoying conversation so I know the next 30 minutes are going to be really fun as we continue that.

We split these segments up into 15 minutes each but there will be time for questions at the end.

If you have them please feel free to add. And I believe there should be an email thread at the bottom of your screen where you can post these.

So typically we start alphabetically by first name. Alissa you all right going first?

Of course of course happy to go first. Wonderful well thank you so much for being on today.

I did a little intro but could you introduce yourself in your own words for our audience?

Sure so I'm Alissa Starzak, head of public policy at Cloudflare.

I've been at Cloudflare for about two years and before that I was in government for a long time for about 12 years and was in private practice as a lawyer before that.

So I have been around for a long time as you will find out when you get into the more detailed questions.

I'm excited to learn about that journey that brought you here to Cloudflare then.

I guess maybe starting at the beginning what was your first job?

What began this career? So I don't know if it began my career but I spent as when I was in high school I was actually I worked in a store a retail store and at one point was sort of the main person working in the store with the keys to the store which was a big deal at the time.

So you know 16 year old and with the keys to a closed store is a little dangerous but my first job.

And you kind of answered the next question where kind of a goofy one here on logins but asking about what was the first thing you had access to.

Maybe kind of extending on that though what was the first thing you remember having access to that was intimidating?

Like the first login system or you know maybe it was the keys to the store that's a big responsibility.

At 16 the keys to the store is a big responsibility.

I think actually though I would say intimidating. I think over the course of your career things get increasingly if you think back on them they look increasingly intimidating.

So when I entered government the notion of getting access to classified information for the first time I was in the national security world was a big deal.

So really intimidating trying to think about it and they they sort of drill into you the concerns that you have about getting access to classified information.

So definitely intimidating at the time. What over time what that made that less intimidating?

So I think there's an ability to step back and think about what you're trying to do and just do your job.

And that's what that's what access is about eventually right.

You know you're getting access for a reason. It's not just there's sort of the initial thrill of getting access to something that other people may not have access to.

But the reality is that you're getting access to it to do a job and eventually you realize the focus is really on the job and you're getting access to it.

It's not it's not the access that is as important as the job that you do on the back end.

And I guess to elaborate a bit on that job that you were doing what took you to a place where you you were trusted with that type of material.

How did you arrive there with that level of responsibility?

So I started out of law school as a lawyer at a firm.

And then I was really looking to do something with a bigger mission.

I wanted to do something in government. I was working for a bunch of partners who done things in government and I believed in a government mission.

And so I really was trying to think about how I can do things as a lawyer in government.

So I ended up and I was interested in foreign policy. So I ended up going into government in the national security world.

And because that was really where my interests were.

And it sort of moved from there. So I had a bunch of different jobs in both the executive branch and in Congress.

Ended up as general counsel of the army at the at the end of my government tenure.

But spent a long time before that in all sorts of jobs that required access.

Which was just interesting.

Again you're doing it you have access for a reason. So it was a very interesting set of jobs.

That is a really interesting set of jobs. And you know I'd love to learn a little bit more about after kind of such a fascinating journey like that.

How did you arrive over at Cloudflare? So I was leaving government in 2017.

And I was really looking for something that brought similar that had similar feeling to it I guess would be the best way of putting it.

So I wanted something a place with a mission.

It was really important to me. I really believed in that you can do something with the job that you're brought.

And I was looking for something where the work was not dull.

Where you were sort of constantly challenged.

And those were really so what I was trying to think about what jobs I wanted to go into.

Those are the things that really mattered to me. And so I started looking around.

And I started talking to some people at Cloudflare. And the public policy issues at Cloudflare are phenomenal.

We have just so many sort of interesting challenging questions.

And there is this deep sense of mission in the company about what we're trying to do and how we get there.

And it's this both of those combined were really why I joined.

And I have not been disappointed a single day.

It was definitely the right decision. Well we're thrilled to have you. And I'm sure every day is like you mentioned not only not disappointing but really interesting.

Could you is there an average day for your role at Cloudflare or is it just new each day.

You know it's pretty new each day which actually makes that the average day.

So if it's not you know we deal with so many issues. So we deal with things that are externally facing.

So that might be things like new legislation or or people's comments about what's happening in the world.

And then there's an internal component of it which is how does this apply to us.

So as we roll out new policies based on what's happening in the world how do we think about what's happening in the world and how we apply them to our policies our internal policies.

And then we my team also runs the corporate social responsibility program.

So we run Project Galileo and the Athenian project and Cloudflare for campaigns.

So it's then thinking about those projects and ways that we can actually expand the things that we do and the good that we do in broader ways.

And we can help we can help those communities help those entities that really can really value our services and can benefit from our services.

And those are such wonderful programs.

Are there any recent stories or organizations that have been using those that really stand out to you.

And I know all of us probably have a favorite project that we've seen from your team do where we're all kind of honored to be part of Cloudflare.

Is there one like that for you lately. You know we've we've been watching a lot of the different organizations that it's it's been it's been such an interesting time in so many ways.

So we have the pandemic and all the organizations that we can help through the pandemic.

So we've had all these amazing organizations pop up during the pandemic to do good.

So whether it's distributing masks whether it's providing information there's a whole slew of organizations that fit into that space.

And then the reality of what's happening in the U.S. right now we have advocacy organizations.

And so we have a lot of advocacy organizations on Project Galileo that are doing amazing things right now in the organization space and really challenging people and thinking about ways that we can make a difference.

And so it's it's it's an amazing experience to feel like you can help those organizations do something that they are where they really are making a difference every single day.

Yeah. And with kind of within that from from the start of being part of that store all the way to running this public policy division and making that difference what advice would you give to the earlier self that had those keys to that store.

My advice would really be to go back to where I started which is that you have to think about why you're given access.

So the questions of access really are about how do you how do you improve what you're getting because you're getting it for a reason.

So if somebody is entrusting you with responsibility do something good with that responsibility.

Do think about what your your obligations are and your responsibilities are and think about the positive things that you can take from it.

And I love the fact that your dog is in the back. Yes please please.

He's not a guest today.

That's that's not the next session. That's the next session. Yeah no but so for me it really is that the advice I would give is that you have to keep your eye on how you do good right.

You have to keep your eye on on how you do your job effectively and take the access and the responsibility that's been given to you and run with it in a good way that makes people proud in the back end and makes yourself proud in the back end.

And I think that's that really is that's been consistent through across my career and it's something I really believe in.


One last question I do have for you and this is probably a good segue into the next guest because it's about dogfooding the internal tools we use here at Cloudflare.

Dogfooding is really important to us and you know the way that we build products which in many of our customers is products like Access which help secure these types of logins that we're talking about.

What do you remember the first time dogfooding the Cloudflare Access product?

What was that experience like?

What could we be doing better with it? You know I think that the funny thing for me about that is because I'm not a technical person necessarily, the glitches that I experience or the things that don't work well they don't stand out to me as much.

So I end up thinking about like hey what does this mean? What do we think about?

What are the policy implications of Access? How do we think about Access controls?

What are the legal responsibilities? So I end up with a whole different set of questions I think than an engineer or it's a different world of how you think about a product.

And I still remember the sort of idea of Access going through that laundry list of okay what should we worry about because there's always something to worry about.

Yeah well I'm glad that we have people like you experts in that field thinking about cases like that that we absolutely should keep as priorities.

Wonderful well Alyssa thank you so much for kind of walking us through that journey and telling your story.

I really appreciate your time being here on this program and so thank you so much for being a guest today.

Well thank you for having me on.

Yeah and Juan up next the CIO of Cloudflare, the person who really owns a lot of the dogfooding of the tools that we're building here.

Juan thank you for being on the program.

How are you doing? I'm all right Sam thank you for having me.

How are you? I'm wonderful. Just for the rest of our viewers I have the privilege of getting to kind of work with your team and you and what you do here at Cloudflare but could you describe what your role is like to our audience?

Yeah so my official title is the Chief Information Officer for Cloudflare and CIOs can mean different things depending a little bit of the business that you're on.

So I have accountability for basically systems and internal corporate infrastructure.

I'm also Cloudflare's first customer you know as you said you know from a dogfooding perspective so I get to work with a lot of the product teams and things like that as well and see how we can you know drive internal adoption with tools and then provide feedback that may be helpful for our external customers as well.

So yeah it's a little bit in a nutshell my job. And there's a lot of responsibility in that job but what was the first job that Juan had?

Where did you start that journey that led you here to CIO at Cloudflare? So I'm originally from Spain.

I've been living in the U.S. for about 21 years but in Spain it's not typical when you're like in high school or things like that you know to actually work.

You know normally you know it's one of the things that I like a lot about the U.S.

culture that you know that the kids you know in high school they get jobs in this stuff because it's something that wasn't happening in Spain when I was growing up.

So my first job if you want to call it that way well I was getting paid so I guess it's a job.

I got an internship internship in Hewlett-Packard in Spain while I was still in high school.

It was one of these programs where like you're like part-time in university and actually part-time inside of inside Hewlett-Packard for a couple of years or something like that and I was studying computer science at the time and I lacked out getting a job in being the administrator of Hewlett -Packard Spain's demo center.

So I it was like I was like a kid in a candy store. I mean you had access to all the latest hardware when hardware really meant something you know it was like millions and millions of of dollars of computers and you know we the job basically at the time we worked with software companies and the model was we would we had a beautiful space that had like you know all these machines and things like that that we order and software companies will come and they will install their their their software in our hardware and they will bring customers you know into our demo center to basically do demos of their software running and completely instead of the our hardware and the idea was that you know hopefully they will like that and it will perform so well that they basically they will buy their applications you know with our with with our hardware.

So I was responsible for setting up a lot of those hardware, maintaining the facility, working with the software companies on on on installing the the software and preparing basically for like a successful demo and also one of the things that we did we did benchmarking also so you know I will learn I enjoyed a lot of nights with a lot of the people that actually know what they're doing at the time doing benchmarks and just like hanging out and watching all these very smart engineers like Peter Packard tweaking hardware and things like that to run Oracle databases super super fast on a liquid system so that was my first job.

That is a very cool first job.

I was a storefront cashier, mine is a lot similar to Alyssa's and that for first job that's sounds really fascinating and I assume then that was the first job where you had to log into a system but not just a system sounds like all of the systems.

Is that right? Yeah so I remember so my first actual logging into I had my first computer was a Sinclair ZX Spectrum 48 at home that was my first computer but the actual first computer that I remember logging into something was it was in a little bit of flash from the past in micro vaxes 3100s and we had them in a university but also my father was in the navy and very close to our house was the navy observatory where like you know we had a big they had some of these micro vaxes and I will go over there once in a while to hang out and connect you know with some of the officers over there they let me connect and run certain things in the network and stuff like that so that was really the first time that I remember having a logging to a computer that wasn't you know my spectrum at home and then obviously you know in university also we had access to mostly sun solaris boxes and these vaxes and then in HP it was like all these workstations and servers with HP UX yes and of all these systems and that's a lot of options here what was the first one that you had access to that kind of scared you that you like oh someone's trusted me with the keys to this so the thing that always was you know nervous to me a little bit like what Alisa said is like we will we will bring you know to do basically benchmarking and things like that actual production databases and things like that you know customer data and you were like setting up things and you basically you know when when you were trying to configure things and things like that you know you're like I was you know in my in my 20s right and you're like they're playing with a multi-million dollar computer and trying to set things up.

So that was you know until until you you get a little bit more comfortable with with things that was that was always a little bit nerve-wracking you know for me at the at the beginning later on you know I I got to work with with actually a little bit later in my career with like customer life production systems they used to run big manufacturing plants and that was a whole a lot of cattle and fish when you're working with real customer systems and customer sites.

Yeah absolutely that trust that those customers put in you to kind of treat that with with the level of diligence that it needs what what kind of made that less scary over time like as you grew in your career like what not just the access to the systems but also the trust that these people were placing in you what what kind of helped you grow there?

I think that you know what what is one of the things that I learned I think always over time is that it's very important never to lose respect with what you're dealing with right.

You may have comfort you know working with or you may have knowledge and you may have done many things before you know when you're like you know working with with real time basically systems that are running whether it's like you know as I said I used to do a lot of ERPs in manufacturing plants but what made it more comfortable is as I said you know not losing respect and having a little bit of a checklist of things that you always do every time that you're approaching one of these things right whether it's like making sure that you have backups making sure that you always have like a point in time where like you can recover to things and you may make a mistake at some point in time right you know you try not to but you know sometimes as we know upgrades go wrong or so having like a checklist basically and being disciplined about you know making sure that not letting you well I've done these many times before so therefore I'm going to get a little bit you know more loosey-goosey or or relax about you know my processes and procedures instead of doing that basically sticking to your discipline and being as I said respectful about the task at hand I think that that is what makes things a little bit more comfortable when you're dealing with that type of data.

Yeah and you know what both of you in very different fields classified information and one with your experience deploying these production systems for customers where something goes wrong it's I'm sure very the terrible day I think you've both really spoken to a common theme about the that trust that someone's put into you and how the response has to be that diligence and that respect.

Correct I mean it's very very it's very important I said like you know being being very I think as you know at least this is something that is that's important like remember you know why you have access to that yeah and also you know and making sure that uh that you're following as I said your your uh training and and being disciplined about things you're you're you're being entrusted with something that many employees in this case when you're working with customers you know they're not right I mean not many people have good access to uh uh operations that are running like a whole company right so right that is uh uh is something not to be taken lightly and so say you know having respect for uh for what you're doing and and as I said you know making sure that you're being disciplined about the things that you need to do to make sure that you you know deliver successfully at the end of that project.

Yeah like like Alyssa said remember you're there to do your job that the job that's why you have permission for those systems um speaking of doing that job and the one that you do now how did you go from that journey all the way to here uh as CIO of Cloudflare can you tell us a bit more about that?

So I uh I uh in my previous company I was a Cloudflare customer since uh relatively early I think we're starting using Cloudflare probably about like 2013 2014 and I've always worked in software right and technology companies is is my thing I love that I love uh I'm a I'm a product person uh and a technology product person you know I don't know I always say that I don't know if I could do what I do in some other industry but that's really my thing so when this opportunity came around uh you know I I uh and having like an admiration for for Cloudflare you know since as I said between uh I started being a customer in 2013 and 2020 and following the the journey I thought that it was something that you know there could be uh uh I would love the the opportunity to to help um Alyssa said something also that resonated with me right I'm a highly principled person and some of this interaction of the problems that Cloudflare work with in terms of legal technology data in in the the the huge impact that has in um you know at the scale that that we do things what's something that that also resonated with me very much so you know when I started talking with people about it will be something here I and and looking a little bit deeper than just is this more just talk or things on blogs or is this really how things work internally so I was very happy that it was you know how and then get a you know be offered the job so I'm very very excited to be here we're excited to have you here um like you said you're you're Cloudflare's first customer in many ways and so that that really um uh is powerful when we're trying to test out the things that we're building in the same way that the things we're building um Alyssa has and her team has this expertise around um with uh the privacy and the sensitivity of what we're doing and the trust that people put in us um one thing we rely a lot on your team is the expertise in deploying something like what we're building here at Cloudflare so love to maybe hear a bit more kind of what your experience is like dogfooding the things that we are building as a IT organization yeah so I mean one of the things that is very important to me and I I truly believe in you know dogfooding and being Cloudflare's first customer I always think that you know if it's not good enough for us it's probably not going to be good enough for our customers right so I think it's very very important that you know during that phase of development and I I work with a lot with with with your teams and and for Cloudflare for teams and access you know we're a heavy uh access customer the other thing that is also very important to me um is uh colleague experience right an employee experience I I I think that one of the things that that uh that uh the thing is very magical it's like when you can deploy technology that not only basically meets the objectives in terms of security functionality but it provides an amazing uh employee um uh experience in terms of ease of access you know low friction uh good performance and things I always I always one of the things that I always say it doesn't matter how functional something it is if it's not fast and if it's not always on you know people are just not going to use it or just going to you know find ways to basically do things around it so uh it's been a a lot of fun you know to just like tweak and provide you know feedback on things like access being able to ourselves you know put a lot of services behind access you know and work with your team and other organizations you know inside of Cloudflare to make sure that uh we can speak to to pretty much any any prospect or any customer out there that may be maybe using maybe contemplating you know using some of our products and say yep this is how we use it this is how how we're deploying it here's some of the things that we have behind it and then as I said you know continue to to work with with the product teams and people like your product managers you know to to uh provide uh invaluable feedback on on something that may be may be uh helpful for our customers down the road.

Yeah and we're grateful to have it um one thing uh we hope you you feel is that you aren't going to hurt our feelings um the feedback you give is the feedback that we'd rather hear from you before customers trust us with that experience so thank you for participating in that um kind of back to um the days in in that lab and in that demo lab what advice would you give to that earlier self um all the way through this journey now to being CIO at Cloudflare?

Yeah so I you know when I look back I think I've been uh you know fortunate primarily that I am doing something that I absolutely love uh you know it's it's uh computers computer science uh technology something that is was a hobby for me you know since I was very young and as I said you know I I told you even like you know that job of of being uh you know that first year about having access to all that stuff was like uh a kid in a candy store it was like basically you know you're doing something that that is almost not a job so I will you know that I I the advice that I always give people is like focus on the thing that it makes you happy and if you can make something that makes you incredibly happy also like a job that you know that uh that uh uh that and a passion that you can continue to develop you're going to be successful at it right I think that you know the chances when you're working on something that you have a passion for that you're doing it well and uh it's something that has a meaning to you and you believe that you're making a difference so I think that you know sometimes it's easy to try to focus too much on like how you you know go up the corporate ladder or anything my experience has been like if you focus on basically knocking up problems on the things that you love a lot of those things basically follow so that's my advice you know that I will give the your my younger selves that continue to focus basically on the things that you love the things that you like to do focus on solving problems in that area and you will continue to grow wonderful advice well I'm so grateful to as like I said at the beginning just get to be a guest uh to your stories as well like our audience so thank you so much for spending the time telling these stories I love uh how um how many things are in parallel between your answers about the trust that people put into um the members who are doing their jobs with these systems that you have access to and also the journeys that led you here to be part of the Cloudflare team I'm really uh fortunate to get to be part of that team with you so thank you for your time here I'm gonna I think we're out of time I know we promised we would um check for any questions uh I think we're okay there so I'm gonna turn it back over to um the Cloudflare for tv Cloudflare tv green room to uh put the next show on but thank you all so much again for your time thank you Sam thanks have a great day you