Cloudflare TV

Cloudflare's Creative Corner

Presented by Jess Rosenberg, Jenny Brecheisen
Originally aired on 

The Creative Corner explores the experiences of creative professionals working within the tech industry. From challenges faced to lessons learned, we will join them on their journey as they share their wisdom as creatives in tech.

Creatives in Tech

Transcript (Beta)

Hi everyone, welcome to the Creative Corner. Today I'm excited to be joined by my friends and colleagues at Cloudflare, some designers from the brand design team as well as the product design team.

Welcome Jenny, Drew, Dylan and John. Hey Jess.

Today we will be chatting about career journeys. So how each of us kind of started out as a designer, what our journeys have looked like, how we found ourselves at Cloudflare.

But first I'd love to start with some brief intros from the group and Jenny if you want to kick it off.

Sure, my name is Jenny. I've been at Cloudflare almost three years so I feel like they're all family and I'm on the product design team.

Hello everybody. For those that have watched a number of these segments, I'm Dylan Welter, co-host of the Creative Corner and the Creative Operations Manager for the brand design team.

Hey all, I'm Drew.

I'm a lead designer on the brand design team. I've been at Cloudflare for about two and a half years now.

So like some of the Jenny, it feels like it's like a family at this point.

I'm John Domboyer.

I'm based in Seattle. I'm the design manager on the product design team.

I'm Jess. I lead the brand design team. I've been at Cloudflare for I think like three years and eight months, something like that.

And yes, this definitely feels like family and I love that we're all here doing this together today.

So first question, how did you know you wanted to be a designer? How old were you?

What were some of the cues? Drew, do you want to kick it off? Yeah, yeah. I remember early on, I mean probably 13 or 14, I had like a bootleg version of Photoshop and my initial foray into design was creating avatars for Neopets.

Like I was like on my side hustle, was creating things in Photoshop that like I'd stolen.

I think I was just starting to find the creative spot outlet there and just really developing that through high school and college and ended up majoring in graphic design later in life.

But yeah, that's kind of my initial foray exploration of design and finding the passion for it.

Did you get paid for this work? Not real money.

Not real money, okay. Yeah, right, right. There was a business involved but there was no actual currency.

Lessons were learned there.

Yeah, exactly. Cool. How about you, Jenny? Oh, I feel like I always wanted to be an artist when I was a little kid but like, you know, you never really think you're going to do what you wanted to do as a little youngin.

So I started off like in a totally different trajectory.

Like computers weren't a huge thing in high school.

When I was in high school, like we took typing class and all that.

But when I at one of my jobs, I was doing like presentations and some like event posters and that really got me like super interested in like creating those kind of graphics and layouts and organizing information.

So then I realized, hey, you can go do what you want to do and find a career in this kind of thing.

And I felt like I had a knack for it. So it just evolved from there and ended up using those computers after all.

Awesome. How about you, Dylan? Um, I had a kind of an interesting like on again, off again foray into design.

Similar to Drew, it started with just no real like interest in I want to be a designer or anything, but more so acquiring a less than legal version of Adobe products to create stuff for me and my friends and for the little like hood rat skater crew we had back in middle school and whatnot.

But I knew that I had always been kind of interested in like design principles, just from the fact that like I would always kind of look at software tools and things like that and kind of mentally deconstruct them and do, you know, is this, is this like usability flow right?

Do I feel good using it? And I would always get really frustrated with stuff that was quote unquote janky.

We just wonder like, why, why didn't they put the button there?

Why didn't they do that here?

And I think it was specifically in my like junior business class, I was watching the iPhone announcement, like the reveal of the iPhone.

And that like paradigm shift to this like touch-based, app-based, you know, software focused product just immediately got me spinning and like, how are, how is, how are people going to use that?

How will people interact with that? Because it was, it was just, it was very radical from like, you know, anything I'd ever really used in the past.

And that was kind of what drove me towards the like the usability aspect of design and kind of like really pushed me into looking into, you know, digital design further.

That's kind of the, in my opinion, my like cornerstone moment, if you will.

Cool. John. Yeah, I sort of went through a similar shift to Dylan. So like in high school and in college, like I ran a small computer repair business on the side and did a lot of like setting up networks and building computers for people and stuff like that.

And I, through that experience, I went to a lot of people's homes and I noticed myself like, yeah, I'd be fixing their problem and like uninstalling some virus that got there.

But at the same time, like I was also getting pulled into teaching how software works a lot of times.

And it would be like, hey, how do I set up this printer?

How do I design this kind of thing in like this program that I bought at Staples?

And I was like doing more of that than repairing towards the end.

And I kind of, I think that planted a seed in the back of my mind, like it would be nice if this stuff was just like better the first time around and more intuitive.

And so I kind of put that on the back burner and then like going to college and studying network engineering and did some internships.

And like during one of my internships, I just ran out of stuff to do.

And because I happened to sit next to a UX designer, I started getting involved in like what he was working on and then got pulled into some sort of like service design work with the support team.

And then next thing I knew that was just like what I was doing. And then sort of made the conscious shift to like look for jobs that did that more of that kind of thing than going to data centers and like racking servers.

That sounds so fun.

Yeah. Are you still building computers, John? Yeah, I haven't for a while, but I'm thinking about a fresh one soon.

I had the new graphics cards come out tomorrow.

Exactly. Yeah. Cool.

So for those who are tuning in that might be getting their portfolios together, looking to land design jobs, particularly in tech, what kind of advice or guidance can you give them on anything from preparing their portfolios to prepping for on-site interviews?

Drew, any guidance? Yeah, I think a big part of it is a process as much as important as the end product.

So including that in your portfolio, talking through your thoughts, your initial sketches, how you arrived, the choices you made to get to where you arrived.

I think it's really important to include in a portfolio as well as to prep to speaking points to that on interviews.

I know sometimes you get lost and you got this really bright, shiny, great new thing that you created, but to really talk about how you got there is almost as if not more important.

Yeah. Oh, sorry. I was going to add to that. Your portfolio piece is also a representation of your work too.

Like your portfolio as a whole is a great way to show if you don't have a lot to put in your portfolio if you're new, the way you present it can be a body of work.

Yeah. Kind of touching on that as well. I know when it comes to portfolios, a lot of people really want to showcase the visual aspect of the beauty of the work they did.

But Drew's point about the process and your role in that project and having that write up of how you approach the problem, how you went about solutioning the problem, and then ultimately what the end result is, is in my opinion, just as if not a little bit more valuable because when people are reviewing these applications through Greenhouse or whatnot, they get hundreds if not even more a day.

And just having really striking visuals is fantastic.

But in my opinion, that just puts you on par with everybody else that gets more than five seconds.

And the thing that really differentiates a good designer from a good designer from a good designer is then being able to dive into the work that's already been validated as quality visuals and explore what were their thought processes?

What was their participation in that project?

How did they work collaboratively? How did they solution? That's, in my opinion, what really differentiates two great designers from the one that ultimately gets hired and really needs a lot of focus and can be difficult to do since it's a little bit outside the wheelhouse of the visual nature of the designer's job.

I think something that should have been more intuitive to me earlier in my career, but wasn't, was that you should build a portfolio that fits the job that you want.

I fell into a trap of just listing all the work I did.

And just by a circumstance of the job I was most recently in, it was a very research-heavy portfolio.

And I was actively trying to not get a job where that would be my only responsibility.

So I think it took me some reps to realize, yes, that is a lot of what I've done, but maybe I should talk more about the kind of stuff I want to do more of.

Yeah, that's a really good pointer. I think that's a great tip for folks who might be looking to find their portfolios and organize their projects.

It's more like you're searching for the job you want, maybe even creating a few different types of portfolios if you're not sure.

I've heard folks do that as well.

Are there any ways to try and differentiate yourself on a portfolio website?

It's just so competitive out there and there's so many talented and strong designers applying for jobs.

What are some ideas that can help folks differentiate their websites, maybe inject some personality?

I guess, sorry, Dylan.

I've got a person that stands out that does that. I'm not sure about someone who stands out that does that, but I would just advise from falling into monkey see, monkey do type trends and stay true to your aesthetic and make it a piece of your work that shines.

Don't just follow the latest parallaxing trend or whatever.

I'm not a web developer in any regard, so I don't follow that stuff.

Though you may have all the bells and whistles, you're going to just blend in at that point.

I think on that one too, letting those muscles not get in the way of the function.

You want to make sure people can get to the work and see your work, that it's prominent and you're not getting lost in parallaxing and scrolls and other effects that can detract from the work.

I think just coming at it that way too is making sure the work is accessible and that you really are showing up in the portfolio too.

Nothing's worse than desperately trying to see somebody's work on their portfolio and not being able to navigate to it.

It's buried in this weird brutalist design.

I would also say, don't be afraid to think outside the box. Some of the most memorable portfolios I've ever come across were ones that were just a complete reflection of the individual's personality.

Specifically, it was, I want to say, maybe six years ago at this point, but the agency I was working for was looking for a copywriter and this individual submitted a portfolio that on the main page was this big promo video that he filmed in a B-movie 1980s Arnold Schwarzenegger movie trailer style about writing copy wrongs.

It blew all of us away.

It was just incredibly refreshing that it put him just right at the top of our minds when it came to all the other candidates.

Stuff like that, while it sounds nerve-wracking to do, I think really does stand out.

Yeah, it's memorable.

It's hard, I think, to that point, and sometimes this only works for the most recent work, but when you do have live things out in the wild to point to, show off that too.

Coming up with an idea is one thing, but getting it out the door and all the organizational and other barriers that were potentially in front of shipping that thing, I think people recognize that that is impressive in itself.

I worry sometimes that people will fear the judgment of all the little minor details that got messed up in translation, but I personally have always been impressed that things make their way out there too.

If I'm like, oh, that alignment is off by one pixel versus the mock-up that you had in your portfolio, I'm not going to be bothered by that, but I'll be impressed that it made it out the door and you shipped a thing and it's in public now.

Keep that in mind on my next review, John. For transparency, John's my manager, so he just said I could be a pixel off.

Oh, there you go.

It's on the record now. Just kidding.

Maybe let's pivot back to career paths again. So, we've all had very different career paths and we've all landed at Cloudflare.

Drew, if you could talk a little bit about what your career journey has been prior to Cloudflare and how you landed at the company.

Yeah, one of my first jobs out of college, speaking to portfolios as well, I had graduated, didn't really wasn't sure what I was going to do.

My mother was actually living in Panama at the time, so I was with her kind of helping her move, figuring out what life was, and I was keeping up with my portfolio and making sure I was checking emails consistently, and I got an email come in to say, we'd love for you to come in.

We've seen your portfolio. We have an interview lined up for Wednesday.

This is on Friday. So, booked a flight, acted like I lived in the Bay Area.

I came back here. They said, great. No, we'd love it. Start on Monday.

So, it's totally faking until I make it. Try to find a car, find my things, find a house, just made it work quickly.

So, that one is just making sure if you have a portfolio and you're actively looking to be your company, you're checking it consistently too and getting back quickly.

So, this all came together within a week.

But it was there, and this is a pretty small financial startup that never really got off the ground.

I moved from there into kind of a photo book.

So, it's a three-star photo book startup, a car shift, a car purchasing, bring it to your door startup.

I was there for a while, and then I was at Twitter for a few years on their brand studio and brand strategy teams, and then ended up coming over here to Kotler several years ago.

So, yeah, I ended up, and it's been interesting to see kind of the difference in from a small startup that has no funding, that is struggling to get off the ground, through to Twitter.

Twitter is a little more established than being here at Kotler for the IPO.

Seeing the different life stages of companies has been pretty interesting.

Dylan, how about you?

Yeah, so I got my start in from the agency side because after I left college, you know, design and advertising agencies were what I targeted, I think, primarily because of the desire to work on, you know, a wide breadth of clients and material.

I hadn't at that point really started thinking about, like, what sort of design specialization I kind of wanted to move towards, and I really just wanted to kind of work on everything, really.

And so agency was a great, you know, great learning period for that, being able to work on multiple types of projects, types of design work, types of clients.

But ultimately, kind of, as I got older and I found myself just, like, shifting interest to specific styles of design, specific areas of design, I also found myself wanting to be, you know, more involved and more engaged in material over a longer lifespan.

And that's ultimately what kind of drew me to look for design roles internally.

And that coupled with kind of my idea to work within the tech, software as a service design space is, you know, what led me to my previous company, Zenefits, and then ultimately led me here to Cloudflare.

The whole kind of mission of state is what made me really focus on this company.

I'm kind of a bit of a nerd, and anything to do with the Internet and making the Internet bigger, better, faster is cool in my book.

So that was what kind of got me focused on Cloudflare for my next role.

Cool. Johnny, how about you? I guess when I graduated college with a design degree, my, like, passion and focus, what I really enjoyed most was print and layout and, like, long-form documents.

I don't know if you find a lot of people that say that. But I started out in real estate, and we did a lot of prints, a lot of, like, brochures, one -pagers, and what's that?

A lot of work in QuarkXPress. We actually were in Adobe Suite.

They just got rid of Quark, so, yeah. Yeah, so, and it was a pretty prominent, well, for San Francisco real estate company who had, like, equity in their brand.

So it's a house brand, and then you have, like, 300 independent agents.

So there was a big branding opportunity there to marry, like, independent contractors under this house brand and, you know, elevate their own platform and style.

So I did that and kind of evolved and pushed their brand a little bit.

I made their very first style guide, and the team grew. So I was there, I think I said, I may have said this already, five years.

And so then I made the transfer into tech and got more into digital, of course.

And this company, I led a whole rebrand as the only designer and kind of got my toes wet a little bit in the world of product design at that point, because their product designer was also a co -founder, and he encouraged me a lot there.

And then I was able to join Cloudflare and be on the brand design team, because I always loved branding and keeping things consistent and building that brand equity, but still had interest in evolving my career and ended up being able to make the jump over to the product design team at Cloudflare.

And I've been doing that about a year now, and just evolving the skills that the product designer wears, their tool belt of skills, but also falling heavily on my visual design skills and just the greater base knowledge that I've had of print, of marketing, of just brand design.

So I've had a well-rounded rainbow of experience.

Yeah, I like how you put that. I can't believe it's been a year since you've been on the product design team.

That's crazy. Yeah.

John, how about you? What is your world, your journey looks like up until now?

Yeah. So I kind of mentioned I started into the world of design by taking on design tasks at a non-design internship that I was doing.

That role ended up transitioning into a full-time role after I finished college, and it was still branded as, I think my title was system engineer.

It was kind of like a DevOps role, did a lot of server management and stuff like that.

But after I did that for a little bit, the designer that I was sitting next to was leaving to start a startup of his own, and it was a company around building tools for conducting remote unmoderated user testing, so kind of like

And I kind of did a reverse job offer to him of saying like, hey, I want to change my career, do this thing.

I want to join your company, you can pay me very little. And I got to be the first hire outside of the co-founders for that company, kind of used that as like, it was more of a product management role.

But because I was building a product for designers, I was just constantly talking to other designers and helping build the things that they needed, and through that experience, was able to transition.

Then my next job was an actual UX designer role, and then kind of grew into leading a small design team of about seven designers.

And then I jumped around to some other startups.

And then most recently before this, I spent almost four years working inside the federal government.

So it was like on a team that was about 200 of us, and we sort of were spread out across all parts of government working on different like early stage projects and like government-wide type things.

So I got to help build like a government-wide design system and a single sign-on solution that people can use for whatever apps or products that they're building.

And the end goal of all of this is like, I always hope to like find my way back to something that was like more hard technology or like true, I don't know, like a tech person's tech company, I guess.

And like when I saw that there was a job posting for Cloudflare, like I wasn't actively looking for something, but it was a company that's always been on the top of my mind.

And it was actually, I got introduced to them.

It's kind of funny when that first startup that I left and moved to San Francisco for, we were looking for offices one day and we were looking at an office that Cloudflare was about to move out of when they were, I don't know how big they were, it would have been like 2012.

And so we like walked into the Cloudflare office at wherever they were at that time.

And it was too big for us, like based on how big we were at that time, but our real estate agent was like showing us around.

And like, I kind of always like kept them in the back of my mind since then.

So it took eight years, but after that, I made my way back here. I would love to know what a .gov design system looks like.

Check it out, design system. Oh man. Yeah. Cool.


So this is a question that is a common one in interviews. And that question is, where do you see yourself in five years?

And I'm going to nominate Jenny, or yes, Jenny, to go first.

Well, seeing that I just have been doing product design now for one year, I still see myself doing the same vein of product design stuff.

And I just hope to have, you know, grown in my capabilities and that tool belt and maybe, you know, eventually start mentoring other people on their journey and in a role.

I have a really great passion for design systems as well.

So I'd really like to more flex that muscle and stay in that and maybe make some nice work that I can put up on the Internet for everybody to enjoy.

So yeah, those are some of my five year plan goals.

Cool. Dylan, how about you? You know, similar to Jenny, like, I love design systems.

I love organization. I love process.

I'm always looking at, you know, how best to structure the entirety of the design function.

In the next, you know, five years, I think, ideally, you know, I'd love to be overseeing a, you know, large scale design operation process, you know, company wide, you know, product brand, just finding ways to better merge and facilitate the design function as a whole within the company.

Yeah, it's probably a little ambitious for five years, but yeah.

Drew, how about you? Yeah, I think similar to Jenny, moving into a space of more design leadership and leadership and finding ways to help build other designers and help other people come into the space.

I think it's been interesting with the pandemic that can shift a five year plan pretty quickly.

And so being able to be more involved in what that looks like.

But I think, yeah, definitely trying to find a way to be get to a space where there's more helping bring others up and be in a more stable place to be able to do that too.

I think it'd be great. Yeah, five years feel so far out now.

I mean, this year is almost over. So John, how about you?

Five years? Yeah, I think like the I don't know what my day to day will look like.

But I think the one thing I want to do more and more of is like, getting design more involved with strategic initiatives and like, you know, being sort of the driver behind like, do we even explore building product X, Y, or Z?

And, you know, what is what is technically possible? How does that translate design and thinking at like, a broader level, with regards to that and, and continuing to help lead a team and hopefully grow all of those careers like my, my goal is like, get everyone promoted and get them like, have more opportunities and help them realize their five year goals.

So I mean, that's kind of like the biggest overarching goal is like, did that happen or not?

I love that. Thanks for sharing.

I think we're coming up on time here already that flew by. But thank you all fam for for joining Creative Corner today and love the conversation and hearing about your careers and suggestions.

And we will have to do this again soon, maybe with some more design family members next time.

It'd be great. Thanks, everyone.

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