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27. Behind the Brand with Heroku's Lead Designer

Hosted by Vikram Rana, with guest Charlie Gleason.

Join Heroku’s head of product marketing and developer relations, Vikram Rana, as he chats with Heroku’s head of brand design and front-end developer, Charlie Gleason. From finding inspiration and choosing tools, to navigating morality and ethics, the two delve into how the team at Heroku approaches design, brand, and one another.


Show notes

Design is at the very core of Heroku, influencing every aspect of the brand and the platform.

Join Vikram Rana, product marketing and developer advocacy lead at Heroku, as he chats with Heroku’s head of brand design and front-end developer Charlie Gleason on his role—covering his history and background, what it’s like to work at Heroku, and how he handles being a custodian for a brand he loves.

From tooling, to teamwork, to the ethos of the brand itself, Charlie and Vik dig into what makes good design (and more importantly) what makes design good. They cover topics like ethics, empathy, humility, education, and bringing your authentic self to work.

(Also, one correction—The Cut is based in Perth, not Melbourne. Sorry, Scott.)

Transcript

Vikram: Hello and welcome to Code[ish]. I'm Vikram Rana. I run our product marketing and developer advocacy teams here at Heroku, and I'm delighted today to be able to chat with Charlie Gleason, who is our head of our marketing design. Do you want to introduce yourself a little bit more?

Charlie: Yeah. Eager listeners may remember me from such podcasts as how we do documentation at Heroku, and I'm here today to chat a little bit about how we do design at Heroku. So my background, I originally studied design when I was a lot younger, and then went back and did computer science for a little while. My focus has always been on that kind of space between computer science and design and how that Venn diagram kind of overlaps.

Vikram: That's amazing, and it sounds like you have a few other really interesting adjacent interests, like generative art, open source, and music videos. Those all sound deeply intriguing. Are any of those sort of related in the way of how you think about design?

Charlie: Yeah, absolutely. I was a very unsuccessful musician who had no money, and so I was always really interested in using design to solve problems, and I think that's a really interesting space, and I suppose that's probably what drew me to Heroku initially. When I was studying design, I had to hassle people to help me make things because ultimately I couldn't do it by myself. And other people are busy and have lives and don't necessarily want to spend all their time building things that I had drew. So I got really interested in web development, and then started making stuff on Heroku, deploying stuff on Heroku. And so it's quite surreal that I've ended up part of the team and to look after design and brand. It's amazing. It's quite surreal.

Vikram: Yeah, it's interesting. When you first came to Heroku, you were I think working for an agency in a publishing startup and things of that nature. Can you tell us a little bit more about that evolution of how you went from maybe those types of environments to Heroku?

Charlie: Yeah, so I originally, when I came out of university, studying design in Australia, everyone went to ad agencies. That was kind of what you did after you finished. I learned a lot about how to design to be brief and how to be fast as well, because advertising is very fast paced and very intensely laser focused on a project. And when that project is done, it's done forever and you move on to the next thing. So it's a very different style of working to what I'm used to now. And then from there I went into startups, because I thought I would save the world and solve all the problems. A couple of friends and I co-founded a startup called Good Films, which was trying to bring some of the kind of social to films, watching films or recommending films with your friends. It was an amazing experience.

Charlie: And then through that, I met a bunch of people. Moved to London and then started working for a crowdfunding publishing startup called Unbound, and I was there for about four or five years, which is a long time in tech. I feel like all of the paths I've taken have somehow led me here, and I don't know if it's necessarily been the most straightforward career path because I think that the side of advertising I worked in was maybe less technical than where I've ended up, but I don't know. It's all worked out for the best I think.

Vikram: No, it's really interesting to hear how you followed your interests. Have there been mentors along that journey for you that have really inspired you on this path?

Charlie: Yeah, I think very early on when I came out of university, I wanted to go traveling, so I went overseas, and realized very quickly that I'm not super comfortable with real backpacking hostel style travel, so I decided to try to get a job in London, where I now live. All roads lead back to London. I started working for someone, Scott Sanders, who runs a really amazing agency in Melbourne (note: The Cut is based in Perth) called The Cut. I got off the plane, I had no idea what I was doing. I'd been offered this job as a designer at that agency. He ended up being an incredible mentor and an incredible friend.

Charlie: It's really interesting, the people that really influence you in your career aren't always necessarily the people that you think are going to at the time. I just thought oh, I'll go to London and I'll hang out and I'll do a job and I'll travel on the weekends and all that kind of stuff. And then, the next thing you know, he had a really profound influence on the way I approach design, and design principles generally. I think one of the really interesting things in design is that principles are universal. I think one of the interesting things about my job now is that I look after front-end development for the marketing side of things and also brand design, so a lot of print.

Charlie: But, design is ultimately a trade at its heart. There's core principles that are always valuable to know and understand and to follow and to a degree, if you'd follow them they will always steer you right. So that was a pretty profound part of my growing up as a designer.

Vikram: That's awesome. And it's interesting as you said, a lot of the essence of Heroku is design, in all of our products and experiences. So how did you kind of bridge from all of those core design principles to a more technical sort of environment like Heroku?

Charlie: It was really intimidating starting actually because it's like being such a fan of Heroku personally and having used it personally. I kind of had to unlearn some of my anxiety around joining the team because I think I almost had that on such a pedestal from a design point of view, and especially coming up through my time at startups, it was such a shining art of how you could make design beautiful for a product that is at its core quite fundamentally technical and quite complicated really. I mean, you don't necessarily see that when you use Heroku by design, which is an incredible thing. But yeah, it's definitely attention to detail. It's the focus that people put into every single piece of what they make. And it's a real undercurrent of enthusiasm for design as a medium and for the impact that design can have on making people's lives better. Especially coming out of a window of time like web 2.0 when everything felt hard.

Vikram: In many ways, things are still evolving quickly and are hard. What do you feel is the essence of our kind of designing those in brand? Because I think one of the beautiful things about Heroku is it's very present but it also gets out of the way very quickly. And so even for us as we talk about our brand, it's not always easy to put our finger on what it is in our essence. What would you say it is?

Charlie: It's kind of evolving as well. That's the other thing that was quite intimidating. It's like putting your mark on something that you really like, that you've kind of picked up is intimidating. To me, the core is in the craft of it; clarity and balance, which are kind of wishy washy concepts, but I think when you apply it across the whole product, it becomes much clearer how that manifests even if it's not necessarily that easy to verbalize.

Vikram: Yeah. And it's really interesting too, like a lot of what happens is that ethos that we have gets reflected out to our customers. I've seen our customers essentially look to our brand and our user experience for inspiration for their brand and user experience. So I think it is really, like you say, it's really hard to put your finger on it, but it certainly seems very intentional on your part and the rest of the design team.

Charlie: Yeah, I think the attention to detail is definitely the most, and craft is part of that, right? Even all the way down to the swag, the amount of time and effort and thought that goes into the pieces that we produce, all the way across to the entire other side on the digital side how a button looks when it's focused. I mean there's like every single pixel, every single dot is really considered. And I think that is the ethos of our brand is really putting that energy and effort into making sure that things are beautiful and functional, and that that balance struck in a way that feels hopefully to the end user, to our customers feels effortless on their part, and that they are kind of a part of it. Because ultimately they are right? Design affects people, and design has an influence on people. So we want to make sure that the things that we create and the things we put out are a net positive on the universe, rather than something that's ever stressful or frustrating or confusing.

Vikram: No, that's a super interesting point. Our user success is really our success. So we see ourselves in them and their success. So that's really a great point. And part of that in your role is, I don't know if this is the right word, like stewarding the brand.

Charlie: Sure.

Vikram: Like keeping us true to that mission because there's a lot of pressures to just sway. So, I don't know if steward's the right word or how you think about that, but can you talk about that a little bit?

Charlie: Yeah, I think the best thing, the core focus to me and with stewardship of the Heroku brand is staying true to the roots of it, but also always looking forward to how we can improve the relationship that we have and our customers have with the brand, and how we can take on new influences and new ideas. So I guess it's trying not to be too attached in a way, so that you can have some kind of balance and not feel overly kind of either way down by the past or afraid of the future. For me personally I use Heroku a lot and I always have. So I think that kind of helps in a lot of ways because when you're in a system or in a platform designing for it, like if you're benefiting from that platform, then it's very easy to kind of push that through to how the brand reflects the platform or how the brand reflects the product.

Charlie: So yeah, I think stewardship. Also I have really great mentors in Heroku, the Heroku design team are incredible. My manager is incredible. So that helps a ton with having people that you can reach out to and have conversations with. Because design is always evolving and it's always changing. You don't always have the right answer straight away, right? Sometimes it's hard work. Sometimes it just doesn't come to you or something feels harder than it should be. And that can be frustrating or feel dispiriting. So I think having people around you, a team around you that you can reach out to or like if you're having a day where nothing's kind of aligning, that you have other people that you can kind of draw inspiration from or get direction from. It's really important as well.

Vikram: Yeah, I mean that's a great point. You and I collaborate on a ton of things obviously and I hope that's as rewarding for you as it is for me. I certainly take a lot away from that. I hope you-

Charlie: Yeah, you're the best. Never doubt that.

Vikram: Well, thinking about that from a humility and empathy standpoint and the point you just made about breaking through the solutions to really these difficult design challenges and brand challenges. Can you talk about how you collaborate across all the different pieces of Heroku from product and engineering to marketing, to sales? I think you'd pretty much touch every part of a Heroku. So maybe you could talk about it a little bit.

Charlie: I think our relationship is actually a good example for that because I think you're incredible at what you do. In a way that could be quite intimidating, but I feel like your communication, you always feel like you're on the same level. And I think that humility and empathy exists across Heroku. It doesn't feel hierarchical even though the manager and my manager's managers and all that kind of stuff. There's no one there that I felt like I couldn't reach out to. So to me, collaboration across teams is a cultural thing as much as it is how we approach something like design. Two things that we try and do to kind of keep that alive. I'm remote, I'm based in London. A massively remote organization. So there's a lot of processes that we've put in place to make sure that everyone feels heard and that remote workers and employees, who are also like locally engaged also have the same kind of voice and that there's collaboration and teamwork always.

Charlie: But the two things that we try and focus on from a design point of view are always creating tools that people can use, so self-service so that people feel empowered to get what they need without that being too intimidating or without design feeling like it's a gated thing that you have to kind of be nervous about approaching. And also education. So making sure that people understand the Heroku brand internally and what our ethos is. And we also put out a lot of external stuff like brand.heroku.com, design.heroku.com, that kind of talks about how our teams work and what our brand is and how we collaborate.

Vikram: Yeah, I mean that's one of the really interesting things about what you do is giving us a common language for design in all of our engagements with developers, whether it be on our website or in our product, I know there's a product design team that you're very tight with. That norming of our design principles across all those teams is a challenge. But what are some of the other challenges that you deal with when it comes to design?

Charlie: It's quite a big surface area. I think in terms of my role especially, because it covers print design, branding, front-end development, back-end development at times. There's a lot of surface area. So I think staying up to date is always challenging and deciding what is important to, what trends especially around front-end development are important to implement and what is better to maybe stay on the safer side of. I think finding inspiration and kind of getting to the cracks of the message or the meaning of what you're trying to convey is really important. I think especially when you're representing a brand and a brand that is as beloved as Heroku kind of finding inspiration and feeling confident to push yourself and to push the brand forward.

Charlie: I think tools are also changing a lot, so we tend to be pretty open to trying new tools, especially on the design side. And I think that's a net positive really because it kind of pushes you to try new things and to challenge yourself, rather than being too wedded to one particular way of doing things. And I think a lot of the way that we approach digital design especially, the tools have shifted a lot and the monolithic organizations that created those tools have kind of given way to a mix of smaller startups or different tools that allow you to do different things in a way that didn't necessarily exist, 10 years ago. So I think that's really exciting because that kind of challenge across for space really pushes innovation and it means there's a lot of incredible tools coming out. That always still comes with trying not to jump on bandwagons.

Charlie: And then I think always design is personal. So I think being sure that you are hearing people when they have criticism is really important and not taking opinions personally. Understanding that there are a lot of people and a lot of teams that have a lot of goals and those goals weren't always 100% aligned, so it kind of comes back to that humility and empathy when you communicate with other teams, with other people and other designers inside and outside of work.

Vikram: You think about where design is headed and where front-end developments headed and where development in general is headed. All these things are moving at light speed. So can you dig into a little bit of that? Where are the things that you said don't jump on all the bandwagons, just the right ones, which are some of the right ones in your opinion, how do you find them? How do you know when you're wrong and move on to something else? Both whether it be design, and I know less about design, but web, front-end development.

Charlie: Yeah, definitely. I think the tooling there's so many opportunities at the moment. I think the meteoric rise of React for example, personally I use React a lot. We don't use react in much of our front-end. So a lot of the front-end of Heroku is built with Ember. So we have a team that really gets Ember and they're really deep in that. So I think understanding where your teams are at and making sure that you make decisions that work best for the team is really important. We do a lot of proof of concepts. So Alastair Monk, who is an incredible designer on the Heroku team and an incredible human being generally, he has a ton of really great small proof of concepts that we can try and we see how they go in kind of controlled circumstances, and then if that becomes a part of our tool train, then that sense and if it doesn't, it doesn't.

Charlie: So I think a big part of that is knowing when to sunset something or knowing when you've tried a new front-end tool, just because time has gone into it developing that and using it doesn't mean that you're totally wedded to it, and being able to walk away from things or giving yourself kind of a trap door to try different approaches is really important in creating a space where experimentation doesn't feel risky or dangerous, if that makes sense.

Vikram: That makes total sense. And for the front-end world and especially the JavaScript world, that's always moving. And you said the development community has walked away from so many things, right?

Charlie: Sure. Yeah. Yeah. Which isn't a bad thing. It's kind of interesting. I think that JSPM was one of my favorite projects. But people have largely chosen Webpack. Right? And I still have super fun memories of the JSPM community and working with those people and talking to people and getting excited about what that project meant, because that was the package manager for JavaScript in my mind prior to Webpack. They may have come out around the same time, but certainly my experience is with JSPM. And I think that people take those learnings and they apply them to new projects or they continue to develop that for the subset of their community. There's a lot of room I suppose at the moment for experimentation and to try new things. And I think that's really important not to get too many monolithic tools like allowing space for people to experiment on the front-end and to try new things. And I think that's something that we try and do internally as well.

Vikram: Not to beat the dead horse on this topic, but it's really interesting, the website makes sense. I have less visibility into the tooling for the design side and all the amazing things that you do. We're working on a prototype now for our new pricing page and you introduced Whimsical. What are some of the inspirational tools or new things you're finding on more of the classic design side? To me design tools is things like Adobe, right? Like Illustrator or something like that.

Charlie: Sure. Yeah. And I kind of touched on that with, I love that there's this real push for new tools and for people trying new things and you see some of those learnings and experiments also implemented in the Adobe suite. So it's like everyone comes up together in a way, which I think is really great. Whimsical is a really great wireframing tool we've been using a lot internally. I've recently personally been using Figma for collaboration, which is an incredible design tool that feels really incredibly fast. I think it's built on WASM which I was talking to friend about this the other day and he was like, I have to dig more into the tooling that actually built that app. But it's amazing. Sketch we use a lot internally and then, yeah, for print stuff a lot of the Adobe suite.

Charlie: I just love that there's kind of competition and innovation happening across all of these different things. And you see that with, like Figment recently introduced plugins and now there's this whole new suite of people pushing out really incredible tooling and trying experimental things within a design application that hasn't necessarily been a part of a design application like that in the past in my experience.

Vikram: No, that's fantastic. And both sides of this coin, right? Traditionally it's this value chain around design and front-end web and then back-end development, like when I was a developer like, hey, there was a designer way over here and then there was a JavaScript guy or gal on a front-end sort of role, and then we'd have some sort of like API contract back in the day it was like JQuery or whatever. Or even before that Rhea, tells you how far back it was for me. But I think you almost have a foot in every role except for maybe hardcore back-end development. Can you talk a little bit about, if you're a designer, young designer today and she or he is looking to be successful in this new world. How much like core design, how much web front-end development, how much JavaScript? What's the designer of today and more importantly even the future look like?

Charlie: Yeah, that's a good hard question. I think from a design point of view, those core fundamentals will always steer you right. Good topography and understanding of negative and positive space of grid systems. I mean, those pieces will always be valuable regardless of the medium. But I think for front-end development if you're designing for the web or for digital, for apps, for things like that, having an understanding, you don't need to be able to sit down and be like, I'm going to now go and build this thing. At this point, I think there's so much, coming in now must be incredibly intimidating because there's so many options, that would be very overwhelming. Whereas when I started out, it was like, where you either did Adobe Flash or you didn't like HTML pages. And there just wasn't that much, so you kind of had an opportunities to grow over time with this ocean of change.

Charlie: And I think that ultimately, now having a core understanding of how your design is going to work is incredibly important, and almost more valuable especially when you're starting out and being able to build these things. Right? So for example, there are certain things in CSS that are very easy to do, and there are certain things in CSS that feel like they should be really easy but are ludicrously challenging. And I think, in terms of being a designer that working with a team, especially on the digital front, when you can see those issues coming up as you're working, then you can kind of step around them.

Charlie: And from a development point of view, I mean, Adam Wathan who created Tailwind CSS, which I really love. And he also wrote Refactoring UI. He talks a lot about this being a developer who wanted to better understand design. And then by starting to learn some core design principles, it was easier for him to see moments where he could quickly and simply make things better without having to feel like, oh, I'm a developer so I can't do that. So I think that humility and empathy that I talked about across teams also really applies to the way that, designers, developers, and everyone in between kind of collaborates and works together.

Vikram: One of the things that I'm kind of curious about too is as you think about these new trends and design, you mentioned generative art earlier like GANs or like a fun thing that developers are playing where we're like, hey, can you spot if this is a real cat or a real human face? Do you see that sort of thing starting to intrude in design likeGAN and things like that, generate useful inspiration or actual pieces for design or where's that headed?

Charlie: I mean, I think there's some really incredible stuff that's happening. Airbnb's internal labs did some--Airbnb.design, I believe it's the site for that--they've got some incredible examples of using machine learning to help with design concepts and help with layouts and kind of understanding what you're trying to achieve really quickly and easily. I think in generative art, and especially I know I've talked about them in previous podcasts, but like Glitch are doing really cool stuff in these kinds of small vignettes on the web that are really easy to hook tools together and create new things or to create generative pieces of art or generative kind of output in a way that I think is super exciting.

Charlie: And I just think that space also kind of opens itself up to experimentation. There's something very playful about it. It's very experimental and it feels very exciting. I don't know. Whether or not these tools will end up evolving into something that we use day to day. Like what the future is for machine learning in design, I'm not so confident on. But I do think that the experimentation and exploration is a super exciting space, and I think I'm super keen to see where it all goes really.

Vikram: Yeah, I think the future is going to be really hard to imagine.

Charlie: Yeah.

Vikram: Yeah. So your guess is as good as mine. It's certainly will bear watching. And that side, like you said, those core principles that you cherish about design or really where it sounds like designers should think about. If you had some sort of parting thoughts around this, how do you capture this gestalt what would you say to folks, in terms of style, process, inspirational?

Charlie: Yeah, sure. I kind of briefly said that I think finding your own style, finding what inspires and excites you is really great. I think there's a lot of opportunities out there now to kind of find inspiration, especially stuff like Dribbble and Behance and sites that really have incredible designers on them that are pushing out incredible work really consistently. And that can be a great place to find the kind of stuff that resonates with you. And I think also if you started out trying to recreate things that resonate with you are a good way to learn kind of patterns in design or what seems to match. So that's a good way to kind of get started. I think looking for inspiration. And also meaning, I think at the moment we're at a real crossroads in terms of our relationship with, let's say climate change and with how much we use of the world and our relationship with what our tools are doing to the spaces around us.

Charlie: So I think finding moral and finding meaning in the work that you're doing that resonates with you or that feels in line with your worldview on what you want to achieve, feels really important in a way that I haven't noticed as much prior to now. Kai Brusch who's Australian, he used to create Offscreen magazine, which is a really great magazine. Which actually I think it's coming out again soon. He talks a lot about this. So if that's something that you're interested in, you should definitely check out his work. And also design doesn't happen by a committee. Everyone has an opinion, they're different. So being true to yourself and to the values that you have and the things that you're inspired by, I think is really important, and in a lot of ways is almost the most valuable thing.

Vikram: The hardest thing, I think for any of us in these corporate lives that we lead is bringing our whole selves to work, it's probably a little cliche, right? Like it's kind of a trait these days to say that, but whoever came up with that, I thought it was a brilliant idea. But digging into that a little bit deeper. Right? You clearly have found a way to bring Charlie in a very unique way. So how do you keep that sort of always with you, right? How do you stay that authentic version of yourself?

Charlie: It can be a challenging, because I think finding the parts of you that are the most core to your internal value systems, your moral compass, and then feeling comfortable expressing them, I think that's like a life's work, right? It's like bringing your whole self to work I think is an incredible movement. And I think it's an incredibly powerful message to send out, especially to young people who are joining the workforce. But I think it's always striking a balance between trying to push yourself to understand where other people are coming from, having that again, humility and empathy for other people and how they relate to the world around you. And also to understand what are your kind of core inalienable beliefs. That's the most important thing. It's striking a balance, and trying to view the world with empathy.

Vikram: The interesting thing about all of that too is that the world of the future doesn't look like the world of the past, right? Like we just had a blog on our article from our amazing GM Margaret on Pride and what it means at Heroku and so forth. How is that notion of diversity and where not only design is headed, but the people who do design, what's that going to mean for us in this field? Do you have any parting thoughts on that?

Charlie: Yeah, absolutely. I think the value of diversity is undebatable, the best possible way to get the best possible work is to have a diverse team with diverse voices, and to create space for people to be themselves and be true to themselves. And I think also design certainly is going through a period of self reflection around the environment, around privacy, around security, around diversity. And those conversations are so important and it's so great just to see that happening, right? To see that people are pushing back against the status quo and feeling like they can create communities that understand them and that value them and push for new, unique, interesting, amazing voices to be heard.

Charlie: So I think regardless of industry, I've seen it a lot in design and I think that's probably what I can speak to, but I think, globally that's hopefully a movement that will just continue to grow.

Vikram: I think that's a great way to put an end cap on this because your voice has been an amazing, diverse voice for me personally, you brought a lot of great energy and an infectious enthusiasm to the team. So thank you for that. Any time I get to work with you it's definitely one of the highlights of my day.

Charlie: Thank you.

Vikram: So thank you so much and it's been lovely talking to you.

Charlie: You too. Thank you.

About code[ish]

A podcast brought to you by the developer advocate team at Heroku, exploring code, technology, tools, tips, and the life of the developer.

Hosted by

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Vikram Rana

Senior Director, Product Marketing, Heroku

Vik is inspired by helping developers change the world. In his spare time, you can find him riding his bike and trying to keep up with his 10yo son.

With guests

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Charlie Gleason

Lead Marketing Designer and Front End Developer, Heroku

Charlie is a designer, developer, musician, and creative coding enthusiast. He can usually be found somewhere in London, probably on a bike.

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