Logins: The Last 4 of Your SSN
Sam Rhea hosts a casual fireside chat with special guests (to be announced) to learn how their careers got started — and where their newfound access took them.
Hello and good morning. My name is Sam Rhea and you're watching Logins. Logins is a section on Cloudflare TV where we talk to members of the Cloudflare team about their career journeys starting with the first time they had to log into a system.
And I'm so excited about the two guests that we have today.
This is our first segment that we've done in a more EMEA friendly time zone.
And we have two team members from our London office on today.
Jen Langdon, Director of Engineering, as well as Matt Bullock, Team Lead for the Solutions Engineering Group.
And both you can see in Jen's background are part of the London office, some space that we all miss, I think a lot.
But we're really excited to get together here and see one another.
And also, I'm selfishly so excited to get to learn about their career journeys.
Hope you are too. So thank you for tuning in. We always go alphabetically to start here.
So we're going to begin with Jen. Jen, good morning. How are you? Good morning, Sam.
Great to be here. Thanks for inviting me. Thank you for being here.
Well, just to kick things off, I'd love if you could introduce yourself to our audience and what you do at Cloudflare.
Absolutely. So hello, everybody.
I'm Jennifer Langdon. I'm Engineering Director based at the London office, as Sam just said.
I'm responsible for several teams within Cloudflare's security portfolio, including the firewall, which is responsible for expanding the toolbox we provide to our customers to protect their applications, and also the WAF, our web application firewall.
Including in that also is actually our managed EFL platform, the frontline platform, which is responsible for routing, validating, securing, processing the 40 million requests of HTTP requests that hit the Cloudflare edge.
I've already learned something. I think this might be the first time someone's told me what EFL stands for.
This is fantastic.
Well, that's really great. So many parts of those systems are so integral to everything that we do here at Cloudflare.
Kind of, though, to start at the very beginning, all the way to leading those systems, what was your first job?
What was the first thing that you were working on?
So just to take you back a little bit, I think I had a bit of an unusual path into sort of computer science.
I remember as an 18-year-old going to the careers office and saying, I don't know what I want to do.
They said, what do you like? I said, I like building things.
I like problems. I like maths. And they suggested teaching or law, which are both great professions, but didn't sit quite well with me.
So I chose economics. And I think that in my first year, I needed a job to help me get by.
And I got this account administration role at this very small software house.
And that's how I fell into engineering.
And so I did a bit of accounting for a while with them. But they took me under their wing.
And by my second year of my university, I was working 35 hours a week there, learning programming and doing my degree.
And did that encourage you to change the course of your degree, or did you stay in economics but kept learning there?
Exactly. It seemed like a great situation, to be honest.
And I was midway through by the time I'd realized that I'd made the wrong choice.
But equally, as I said, I like numerics, I like numbers. And so I was kind of getting the best of both worlds, albeit slightly frantically.
Yeah, that sounds really busy, really stressful.
And I think one thing that can make a lot of jobs stressful is, we have to work this into the segment, the login that you have to systems, because that really implies someone's put trust into you, right?
You're giving the keys to something that you're responsible for. I imagine working in that role, you had the keys to a lot of important things.
Was that exciting, intimidating, scary?
I think if I'm honest, initially, it was exciting and motivating.
The things that I probably didn't realize and be honest about is that I was, you know, 19 years old.
And as the accounts assistant and a junior member of the very junior member of the engineering team, I suddenly found myself with bank access, logins to systems in a way that I've never had them before.
And the thing about this company was, it was a fairly small startup, it was doing very, very well.
But I didn't realize until much later that me having access into my Lotus Notes email, which is what it was that actually gave me the same access as, you know, the lead architect on all of the applications.
And, you know, it wasn't until I made some mistakes, I really was able to understand that.
And was that what made it less intimidating over time, like learning from the mistakes, understanding the complexities of it?
I think learning from mistakes, certainly.
But I think like, I think one of the things that made it less scary and intimidating for me was probably twofold.
I think, firstly, as I progressed through my career, whilst you need any type of key to deal with a use case that's pertinent to you, right, it's almost just as important to understand what else you can do with it, what actions you could inadvertently take with that access and what are the risks.
Just so I began to understand the negative repercussions and be mindful of that.
And sometimes I found it pretty scary to feel like I could put my hand up and say, you know, I need to understand this, I don't quite understand this.
And after I got over that hurdle, and wanting to understand what else this key could do, whatever that key is, it became a lot less scary because I was engaging more mature processes and teams around security and operations.
And for me, that was really key.
Yeah. And after you, so you graduated with an economics degree, you'd spent all this time in a software house.
What did you do after graduation?
What path did you start on then? The day after graduation, I joined that same software house as a as a junior developer that invested a lot in me.
And I felt like I absolutely wanted to do the same.
And, you know, that's kind of how I got into software engineering.
And, you know, you mentioned them investing in you and you starting when you're a junior engineer, 19 years old.
And now you lead a very large engineering organization.
What what did people do to kind of help you grow when you were a junior engineer that you take into your leadership role now?
I think I think one of the key things is, I was really fortunate and some of the people that I had managed me, it's it's it wasn't I'm in my age on a bit now.
But, you know, back in my first two roles, I was in the organization, let alone in the team.
But I've been very lucky with the mentors that I had. And I think humility, I think, in terms of what it is that you're doing and understanding the risks.
And I think having everybody on a level playing field and making sure that you're learning, not knowing that you're, you know, really learning from your mistakes and you're bringing that inherent culture, I think, into the team is probably one of the most pertinent things I learned.
To kind of speak back to the piece about the keys and the risks and repercussions of those.
One thing I know that helps me sleep better at night is second factor authentication, something that I'm looking at the hard key on my laptop right now.
And when I see it, I'm a little more at ease knowing that those levels of security protections kind of exist in this ecosystem and continue to get better.
Do you remember adding two factor auth to a login workflow for the first time?
I remember when I had to do it with SMS for my Gmail account.
I had no idea what was going on.
Do you have a similar experience adding it for the first time? I kind of do.
Yeah. I mean, I think it would have been maybe 2013, I'm guessing here, when I joined a technology startup that was kind of using Google Suite.
And I hadn't even added it on my personal phone yet.
And I remember thinking this idea of verifying two distinct pieces of evidence makes so much sense.
I also recall quite a lot of interesting pushback.
It felt like it was perhaps an overhead or slightly wary. Its significance for that took a while to take place.
But then it's just become, I agree with you, it definitely helps me sleep a little better.
And it's pertinent just not to my professional life, but across my personal life and that of my children, frankly.
Yeah. So started with that software house, leaving school, was at a startup.
When did you arrive at Cloudflare? So I arrived at Cloudflare, I started actually in April 2019.
I was on a sabbatical. So I was CEO of a previous company, and I hadn't really taken a career break since I was 19.
So in January 2019, I said, I'm going to take a sabbatical.
And then all of a sudden, I was introduced to John Graham-Cumming.
And I remember having a conversation that actually was with my wife and saying, it's OK, I'm on sabbatical.
My 12-month sabbatical lasted four months before joining Cloudflare.
So in terms of why was that?
I mean, I think there are three very key things, right? Firstly, the people. The more people that I spoke to at Cloudflare, I realized what an incredible team it was and how motivating it is to work with smart people, people who are smarter than me.
And secondly, I think the mission that people talk about an awful lot.
To build something better for all is an incredibly motivating proposition. And lastly, but by no means least, I think the reason I did that was because the vast array of difficult but super interesting problems we get to solve on this mission.
I get to ask that question, what brought people to Cloudflare, each week on this segment.
And it's pretty fantastic. The themes, very similar. The people, what we're doing and the nature of what we're doing.
One thing we do a lot, of course, is also dog food.
Dog food, what we build and the things that we're creating that are going to solve problems for our customers.
One of those things that we're building and continue to build is a product we call Cloudflare Access, something that helps as a VPN replacement and to secure authentication to resources.
Do you remember using Cloudflare Access or any of the dog fooding phases for the first time?
And what was that experience like, trying something out inside of Cloudflare that we were building at Cloudflare?
Yeah. I mean, I think dog fooding, to be clear, I wasn't there for the Access launch, but the dog fooding, I wasn't participating in that.
But dog fooding is an intrinsic part of what Cloudflare does.
And that has been, that's really quite enlightening when you come and you realize the scale that we actually do it at.
And again, we talk about kind of resting a little better at night and having our safe bathroom place and understanding what this looks like when we roll it out and the effect it's going to have on our network.
And dog fooding, we do it, you know, our standard release process use exactly that.
So it's a day-to -day thing. It's certainly not product -based, but yeah, to your point, it helps me rest a little easier.
And one kind of last topic of questions before we move over to Matt Bullock there.
What advice would you give to that earlier self, just starting school, working in that software engineering company?
What would you tell that version of you? I think I'd say two things, probably.
I think the first is there is so much, there is so much pressure when you begin to learn something new.
And I think Matthew spoke about this actually in my very own orientation.
There is so much pressure to feel that you know things and not put your hand up and be sort of vulnerable.
And I think if I could go back and I'd like to think this stays with me today, not knowing the answers and actually sort of putting your hand up and just being, and leaning on colleagues and being, being very honest and humble about that stuff.
I wish I'd felt comfortable doing that earlier as opposed to me feeling like I had to sort of prove myself in situations where I wouldn't, I would like to have done it differently.
And I think probably the second point to that, Sam, is just what I raised earlier, which is when it comes to security, whether it be about systems, people, it doesn't really matter.
It's about understanding not just what you and therefore how it can affect our people and our organization and just understanding the unknowns.
As I've got older, I worry much more about the unknowns.
Yeah. That's good advice for any of us.
I think at any phase, especially I find it challenging at all phases of my career to when you're learning something new to realize to have that vulnerability about saying, I don't know what's going on.
And if you're able to do that, you're able to do that second piece of advice you have better, I think.
Yeah, that's exactly right.
Focusing on the security and systems and the people. That's exactly right.
Well, wonderful. I've really enjoyed getting to hear from you and thank you for your time being here on this program.
You are welcome to stick around and listen to Matt answer the questions.
You don't have to, it's not a requirement. It's not going to be as interesting, I'm sure.
My turn. But Jim, thank you so much for participating today.
Sam, thank you so much. It's been a real pleasure. Wonderful.
Matt, are you ready? I think I'm ready. Yeah, let's go. I've already seen that the top of the show has already gone first.
So yeah, formality. This is where the viewers just drop off, I think.
We get to learn if you're ready or not. That's for sure.
Let's see if you can tackle the first task. Who are you and what do you do at Cloudflare?
So I'm Matt Bullock and I'm a Solutions Engineer Team Lead.
So what a Solutions Engineer or an SE does is, Jen's department built these awesome products where Sam, you've designed or put together an idea of what a product looks like or should look like.
Jen's team has built it. I'm the one that will go to the customers that hopefully will end up buying that product or pitching it to how it will make their lives easier, how it would integrate and sort of talking through the technical steps of how they would implement Cloudflare.
So I'm on the sales side of the org. Connecting the engineering and product to the customers.
I'd say the Google Translate, because obviously engineers and product, there's this perception that they don't talk to customers or customers.
And it's we're the middle person that's sort of on the customer's footing and then on the engineers as well to say, we're building this.
What do you think? And then being that middle person. Well, it's a tremendously, I'm so grateful that role exists.
Just because what you're, especially the Solutions Engineers, are able to uncover from what customers need and are trying to solve.
That is so helpful to what we're doing on this side of the house.
Long before you were doing that translation, what was your first job? I seem to remember an email when I asked you to be on this program about something exciting to share.
Where did you begin? My first job while at uni was bartending, working behind the bar.
But my first one, I graduated in 2008 and there was obviously a big financial crisis around this.
There was no real jobs. There was no sort of hiring from university.
It was super competitive. So I had a friend and it was like that sold and exported commercial vehicles, so trucks or lorries abroad.
So they would buy secondhand trucks from Horlius and sell them over. Yeah.
Into Africa, into Kenya, South Africa. And I would do originally on for the marketing side and do all the email and sort of communications and then did all the advert placements on the website.
So that's my first sort of role. And what did you study?
Did you study marketing in school? And that's what led you to that role?
It was business studies. So yeah, business sort of core. I had no idea coming out of my A-levels what I wanted to do.
I know I enjoyed business at school. So I was like, OK, I'll do this at university.
I wanted to go to university. Might be the first in my family to do it.
But yeah, so business was the one way I was like, oh, it can be applied to a lot of different things.
So that's where my focus sort of went.
And what took you from exports and trucks into software? What what happened after that?
So there was sort of, unfortunately, as I said, I joined the team and there was some redundancies in that small company that made me sort of do more than marketing.
So I was the IT support guy. I had access to the server that was on the side that had all the sort of backups and was doing things like that.
And I was doing email marketing. And I met a girl 10 years ago and sort of who I live with now.
But she lived in Essex and sort of I wanted to get down to London.
So and this is sort of interesting in the journey, because that first company, which was an email company, the person that interviewed me there 10 years ago, well, I think seven years ago was Nella Collins, who I'll talk more about later.
But Nella is the CSM team lead in London at Cloudflare. And so that may give you an idea of my journey into Cloudflare.
But yeah, it's sort of I moved to a technology company in London to do email marketing.
Wow. One thing that's really fascinating about both these conversations is the journeys to Cloudflare started with a job, either right after school or while you were in school, that kind of took you into a new field.
And that's I just love hearing that.
It speaks to, I think, some of the ways that people's careers go in unexpected directions.
When you were given those new responsibilities that started you on this journey, like you mentioned, you had access to the server and the IT systems.
What was that like being new to the field and new in the workplace? It was sort of because it was the first part of the small company was fine.
There was the Internet was really bad.
It was rural. So I was always on the sort of route to sort of restarting it, configuring it, where just and it was just playing around with things and talking to.
There was remote IT support, a company, and I was talking to them and they were the ones that always sort of interface with me to go on the server and do this.
So I was learning things about Microsoft Exchange and all these random sort of products and just getting.
I've always been interested in tech.
You know, I've always took things apart. My dad used to go mad at me that he would buy something, a toy, and then an hour later be in pieces because I want to know how it works.
And I've always had that curiosity and sort of getting access to these this server that had all this sort of information, not just getting to play with it and learning things as I went.
And so, yeah, that was my inquisitive nature.
And what what kind of both made that less intimidating, but also gave you more comfort doing that as you progress in your career?
I think so. That was yeah.
Having the people, the sort of the IT help us at the end to sort of talk through and also knowing that the company was quite small was like fine.
And I, oh, if I do something, there's going to be someone else I can ring up and get to get to sort of recover it.
I think when I moved down to London, my first role where I was sending him out, I then moved to the infrastructure side.
And I started playing with Linux for the first time and getting root admin and to be like mail.
The MTAs that sent out the email.
That was probably the scariest moment. And that was like I remember there was a naming convention that I failed, which was like I added a space at the start of the file config.
And when the script ran, basically this script just like errored and took down the whole email sort of MTAs.
And I was like, everyone was just like my everything just sort of rocked up.
And it was like, oh, how do I move white space?
It was just your head. That was a baptism of fire. But that's sort of the progression to the keys and like, oh, this is nerve wracking.
And so making that first mistake like that was when it opened up like, wow, I could just take a whole business offline by doing something really stupid.
And that probably slowed me up a bit when I went to that stage.
That is probably the most scariest thing I do remember that day.
Yeah, I bet you remember that day. One thing that you've both mentioned about kind of growing in your comfort using these systems and also the appreciation for the sensitivity of it is making a mistake that you can learn from.
I think that realization that, oh, if I don't treat this carefully, if I don't fully understand what I'm doing, I can kind of cause an issue.
One thing you've also brought up a bit is knowing that you had someone who you could call to get help with.
Has that brought that empathy that someone could have with you as you were learning?
Has that influenced your SE journey a lot?
You have a similar role sometimes. I totally think so. I mean, I've been really lucky with my sort of mentors.
So Nella, who I've mentioned, has been a big advocate throughout my career.
So when I started, I was a CSM at Cloudflare.
CSM is a customer success manager. Their role in the sales team is if you are an enterprise customer, they do your day to day sort of account responsibilities, make sure you're happy if there is any issues, trying to find the right people to find the resources to help with that.
When I joined, there was three solution engineers.
It's James Ball, Michael Tramonte, James Crocker. So all of these are now leads throughout the world.
But there wasn't many SEs around. Their time was finite and they always remember like those three sort of just giving me things to do.
And it was subtle coaching that I didn't realize. So it's like, oh, can you can you build this or what would you do here?
And I was like, oh, it's this isn't this.
And it slowly progressed me into a role where I felt more comfortable with the technology side.
I don't think I could have come directly in as a solutions engineer.
But those three and the tasks they gave me and the challenges that I enjoyed is I think the reason it sort of pushed me to then ask Nella, my boss as a CSM to go, I'd like to be an SE sort of moving into that trajectory.
And a little earlier in that trajectory, how did you find yourself at Cloudflare?
Like what what eventually brought you there?
So I know I mentioned that a lot, but she was at Cloudflare.
So I've been at Cloudflare for coming four years in September.
She's been here for four years now. So when the EMEA set up their whole London office, it wasn't a nice office like what Jen has in her background.
It was one floor called Lamington Street.
So there was 10 people in the whole sales team in EMEA.
We're now well over a hundred. So Nella was like, hey, I think I know you're looking.
I've this customer success role is available in London. Are you interested?
I was like, yeah. And sort of put my CV together. There is I'm not going to I don't want to allude to too much, but Michael Tremonti remembers interviewing me and how nervous I was.
I don't interview well at all, which is people that know me inside Cloudflare will think that's surprising.
But I do get sort of nervous.
But yeah, I remember those days going through the process and joining Cloudflare to CSM.
So, yeah, again, thankful for Nella. But seven years ago, moved me to London.
But then four years ago, sort of enabled me to come to Cloudflare.
Yeah, we're glad you're here and for participating on an interview program.
You do interview well. You're doing a great job so far. Yeah, I mean, it's fine.
I think so. I'm sorry to say, but when I saw because we have to do a lot of recruiting, all of this, I think probably in interviews a lot.
I try and make my first initial calls like to be just a chat and sort of comforting.
So learning from that and sort of being more confident.
And again, having people to ask and trust to Cloudflare helps you sort of get more confident in what you do.
Just that willingness to learn, but then more importantly, to have people around willing to teach.
That's so valuable. You have been at Cloudflare long enough that I think you can probably speak to some of the evolution of our own products that we've been building and using for some of these same challenges, the types of logins and security challenges.
Do you remember when we began rolling out Cloudflare Access?
I do remember because we we had these sort of our standard products at CDN, WAF, DDoS and then sort of Access became this shiny new tab.
But I think before that it was moving our products to this Cloudflare Access.
So the first real like using it and what it sort of meant was I used to get home and get pinged from San Francisco on a Jira ticket or you have a look at this.
Can you do a comment? Which meant laptop out VPN? Look at a comment, type a few lines, shut my laptop down.
With Access, I could literally on the train home on my phone, click authenticate in, type my comment, done.
And that was like the eye opener for me of what this could achieve.
And that is one of my again, obviously, when you do pre-sales, using these little stories and how it impacted me, that's what I sort of refer to.
And that is my first vivid memory of using Cloudflare Access.
I think the best way we can speak to these products is when we can speak to them as our own customers so that those stories, the good and the bad.
The things that get an opportunity to tell customers when, why we made decisions because we were solving something frustrating that we didn't expect.
And those are really powerful.
One question I do have for you about that interaction with customers.
When you're speaking to them about kind of how we secure what we do at Cloudflare, what challenges do you hear from customers about what they're trying to secure?
What are the problems that persist for them? I think so. Back before the pandemic, everyone was very behind their VPN.
Oh, my VPN works. I'm used to it.
Access. And I think when this pandemic happened, everyone was just thrown at home and people realized VPNs could not scale.
The customers that I've seen in this is just how easy it is.
And we did multiple calls throughout the pandemic of like 30 minute onboardings.
And we had customers set up and enabled. So when we're going into this, my sort of demo is I spin up a website using Argo Tunnel, which is another product that we have, and just lock it down with Access and then go to them.
Now you can't. You have to authenticate. And those 15 minute demos of how quickly people can onboard the web apps is sort of the eye opener.
There is no slide deck.
There is no pitching or conversation that does that amount of justice in that sort of time.
So it's speed. And when they see that and what they can do, people then move away from the, oh, I need a VPN.
I can, oh, I can actually just build this and secure my JIRA apps, or I can mimic what Cloudflare have done because I'm running this.
And they start small. And then the next thing they're doing SSH, then they're doing mutual TLS, then they're doing all these extra things.
It's trying to, it's just getting that little push to make that first jump because they're used to something and it works.
And when it doesn't work, that's when all the panic sort of kicks in, which is, but it's the little, get them onboard first, get them a little, spoon feed them a little bit.
And then they sort of just, like with all of our products, just start consuming and start building out.
And just to, I guess, kind of remove some of the mystery about moving to a new model to get to see it in action, you kind of can reduce some of that, the potential confusion for what this migration would look like.
Well, Jen, Matt, thank you so much for being on this today.
I've really enjoyed getting to learn from your journeys.
Thank you for your time. Thanks very much. Thank you. Have a great rest of your Thursdays.
Me too. Bye bye.