S2 • E7 – Nov 10, 2021

Inside Marketing Design at Loom

with Senior Director of Brand Design Stewart Scott-Curran

with Senior Director of Brand Designs Stewart Scott-Curran and

When Loom rebranded recently they handled it all internally. In this episode you'll learn about how they tackled this process (and the 2500 logo options they created along the way) as well as more about the ways the brand and product design teams work together to ensure a seamless experience for their users.

Timestamps

0:00 - About Loom

1:50 - Team structure at Loom

7:30 - The benefits of in-house brand design

10:10 - Areas of focus for the brand design team

12:25 - Infusing brand in the product

18:40 - Tools at Loom

20:30 - Metrics of success and testing

26:15 - Building the marketing site

27:40 - The Loom brand

30:10 - The rebrand project

37:15 - How the team collaborates on a project

44:20 - Current challenges

46:40 - "It's only software"

Transcript

Charli: Welcome back to Inside Marketing Design, everyone, and if you're new around here, I'm Charli. I'm the creative director at ConvertKit. And this is a show where I speak to people on brand and marketing design teams in tech to learn about their work. Today on the show I'm speaking with Stewart Scott-Curran, who is the Senior Director of Brand at Loom. Now Loom is a video messaging tool for work, and it's one I use myself to make quick screen recordings, to share feedback or to talk through a design. So my teammates can watch it and respond asynchronously to give me feedback. As a company, Loom is around 160 people now on the team, but Stewart joined at the end of 2019 when the team was just 45 people. So it's grown a lot since then, and he's built out the brand team and shares lots of great insights in this episode about how he structured the team, the rebrand that they did internally last year. That was a very big project, and lots of other super interesting things. Before we get into it, though, you know I have to give a big shout out to our season two sponsor, Webflow. Webflow is a no-code website building tool that I use personally for my own websites, because not only does the designer let me build out the design functionality of a website visually, but they also have hosting plans that let me ship the site and make it live super easily. And this is always why I recommend it for portfolio sites in particular, because who wants to deal with servers and cPanel and annoying stuff like that? We just wanna make a fricking website. Check it out for yourself at InsideMarketingDesign.co/Webflow. 


And now let's get into it and take a look inside marketing design at Loom. Welcome to the show, Stewart, super excited to have you here. As I told you and as I recently just told the listeners in the intro, I use Loom myself and I'm excited to dig in more on the brand side, because I've obviously been using the product for a while. Excited to learn about it.


Stewart: That's awesome. Thank you for recording with us.


Charli: Of course, let's start with getting the lay of the land of the design team at Loom. So I know as the Senior Director of Brand, you lead the brand side of that design team, but I'm curious to hear how that fits with product and who's on your team.


Stewart: Yeah.


Charli: Give us the info.


Stewart: So design weight at Loom, we're probably around 15 or 16 people, I think. Company is around... I don't know. It's hard to keep up. We're growing so fast. Like probably 150, 160 right now. And yeah, that's across product design, brand design, research, a couple of other functions too. So the majority of the designers are on the product design side. I'm a Director of Brand Design, and I have a colleague, a Director of Product Design, and we run design together. So we work very closely. We have shared crits that we do a couple of teams a week. We have like a Monday morning hangout team, which is design way. So we're very much cognizant of the fact that we really wanna continue to have a really solid design culture across both product and brand. On the brand side, there's myself. We have two designers, we have a producer and we have a strategist/creative director.


Charli: Interesting.


Stewart: Yeah.


Charli: Can you tell me more about that brand strategist role and the type of work they do?


Stewart: That's an interesting role because our strategist is called Brooks and this is the third company that I've worked with Brooks at.


Charli: Oh, wow.


Stewart: Which is kind of interesting, and the funny thing about that strategist role is that it's been something slightly different at every company, just based on what the needs are, based on what the structure is, what the organization looks like, the stage that we're at, the type of work that we're doing. I would say for us right now it does like a couple of things. Like one thing is that we all know that companies can tend to be siloed. We're all moving really quickly. Each function is focused on its own goals, its own OKRs or it's own kind of strategic initiatives. And obviously there's a lot of collaboration that has to happen across those teams, but it's very easy for folks just to kind of slowly drift apart. And so the strategist really can be like the glue that keeps a lot of these functions together. And so much as marketing has an idea for a project, the strategist plays a role in helping understand what the goals of that project is, translates those to some prompts, a brief for the brand team. We then start to work together on what that design looks like, what the copy's like, what the possession and the messaging is. And the strategist then really kind of assumes a hybrid like they do about copywriting, they do about creative direction, really just making sure that all of the work that we do, it's gonna speak into our highest level objectives for the brand, our brand promise, our highest level position and strategy, et cetera. So it depends on what stage we're at in the project as to like what role did they play specifically, but that's kind of what they do for us right now. There's a lot of interaction with other teams in the company just making sure that everybody's kind of pointing in the same direction.


Charli: I love that, and the creative producer, can I assume that's someone who is like working through project management and making sure things are on track and what people should be working on when, that sort of thing?


Stewart: Absolutely. Making sure all of the right people are in the room at the right time. Things are on budget. Things are moving along. Keeping people honest as to like what we need to be delivering, any potential milestone for what that project is.


Charli: Yeah, it sounds really like you've got the designers and you can really focus on the work itself because you have these two people on the team who are ensuring everything is aligned at a strategy level with the rest of the company, and in ensuring things are on budget, on time, and planning the work of what to do when. That just must be such a relief for you and the designers to know that, that's taken care of.


Stewart: That's the hope. I think the reality is that there's also a lot of just overlap in terms of what we do. We do, do a lot of collaborative work. We will do a lot of what we would call jam sessions, which is just getting everybody in the team in the room maybe for a whole day. And we'll have various prompts that we'll kind of work on together. And we'll generally like uncover potential solutions together. Like each person can bring in their own perspective and area of expertise. So we try and keep it as overlapped and collaborative as possible. But it's definitely helpful to just know that there's somebody on top of the timeline, the budget. There is somebody making sure that we're not gonna... If there's a piece of copywriting that doesn't quite fit, we know that they're gonna catch that and flag that, and potentially offer some different solutions.


Charli: Yeah, definitely. And I love that you have those jam sessions as well, because that gives everyone a chance to be creative in that way. I know you mentioned to me that this was a conscious decision that Loom has made, right? To bring brand design in-house rather than using contractors, which I believe is what maybe was happening previously. Can you talk a little bit about that? About why you made that decision and what benefits you've seen from approaching it this way?


Stewart: I think like I know I came on to Loom relatively early when there were around 40 people or so, and there was already a brand designer there. We quickly spun up a team of like three or four people. So that's like a pretty heavy investment and an internal brand team relatively early. I think the thinking was really like for Loom, we're in a little bit of a unique position to a lot of companies and so much as we're kind of creating a category as we go. It's not that we're showing up and we're saying, "Okay, we're like company X, but something different."


Charli: The uber for whatever. Yeah.


Stewart: Yeah. We're not really doing that. It's really a case of trying to explain to people that this is a potentially a new way of working, you know? This is something different. This is video messaging for work and that's something slightly different. And so I think investing in that brand team early, really allows us to go deep into figuring out how do we tell that story, how we connect that back to the product that we're building in a really tight and cohesive and structured and collaborative way. We could definitely use agencies to do that work, but we really wanted to have a small team to begin with. Someone who's really understands the space, understands where we want to go can really kind of go deep into the product strategy that we have and then start to bring that to life over time as the company evolves and grows. And we still collaborate with agencies. We still collaborate with contractors and freelancers whenever we need a certain level of expertise, but it's really helpful to have a group of folks who are really deeply embedded and rooted in not just the product or the industry space, but also the culture that we have. We want to try and express that too.


Charli: Yeah, totally, and there's just so much value in having that expertise in-house, right? And having people who understand deeply the product that they're marketing and the brand that they're building it for, and they can apply all those insights into their work, perhaps easier than an external designer would be able to. Yeah, makes a lot of sense.


Stewart: I think so. I think that's the hope anyway.


Charli: Well, let's talk a little bit about the types of projects that you and the brand team work on. What would you say are your areas of focus?


Stewart: It depends and it varies. Obviously I'd say probably like three quarters of the work that we do is marketing type work.


Charli: Yeah.


Stewart: So this will not come really as a surprise to anybody, which is loom.com, the website. Making sure that's expressing what we want it to express, it's performing, you know? It's working for us. The content and the copyrighting that comes with that. The animation work, the visual design, obviously. And then there's the growth marketing side. So we're running campaigns. We have a brand campaign out in the world right now. So those creative direction collaborating with an agency to bring that to life. Then there's like the more tactical sides of that. We're just doing... We're doing ads, we're doing Google ads, we're doing Facebook ads. We have growth campaigns that we work on internally to do that. Sometimes we collaborate with an agency too. So that's kind of it on the marketing side. There's the content as well. We have a blog. We do eBooks, you know? That type of stuff. So there's some work there. And then the rest of it is kind of split between tool creation for the rest of the company. We work on deck templates for sales. We work on sometimes bespoke projects for potential high value customers. And then there's the cultural side too. So we're doing a career site for People Ops. We're organizing a company offsite. So there's kind of like a visual design system around that. We do conferences. So we design conference booths and various types of kind of swag and the stuff that comes with that. I think that probably covers about 98% of what we do. The other 2% just being the random things that pop up now and again. But yeah, it's kind of like marketing/culture. And then obviously, part of that comes with collaborating on product and making sure that we have brand infused into product and vice versa. But that's kind of like... That's less of like what we work on and more just like that's always on and what we do. And we cannot do that by having regular meetings through the week. It's not necessarily like, okay, we have this project now. We're just always trying to try and keep that on.


Charli: Right, like it's a responsibility for your team rather than a project. It's just like you're always responsible for it. Whenever you're giving a critique to product, you're giving suggestions or making sure that the brand visuals and voice is expressed through that too.


Stewart: And uncovering opportunities where the two can mesh better. You know?


Charli: Yeah.


Stewart: And that's not always visual design. Sometimes that's just like a tweak to copyrighting in the product, like something that we've been tooling with on the marketING side. Maybe we wanna bring in some of that tone of voice to the product too. So we try and keep it to a million little things that all add up to hopefully, something bigger, rather than, okay, we have a project now and we wanna bring brand into product, you know? We try and keep it a little bit more natural and organic.


Charli: Yeah, and I feel like maybe that's the way to actually make it happen as well, you know? Because if it was a big project where, I don't know, it's gonna take a while, you got to spend the time planning it, it'd be easy to deprioritize it in comparison to other things, perhaps that marketing needs. But when it's just, like you said, a million little things, you can fit them in easier and just slowly over time you get more and more of the brand in the product.


Stewart: I mean, I've certainly had trouble before at previous companies with brands and product collaboration, just because the timelines are different. Everybody's workload is different, the priorities are different. And whenever we feigned an opportunity to do something in product, maybe they are focused on something else and it becomes this kind of game of tennis where you're just throwing something back and forward over the net and never really land on anything that feels great. So we wanted to try and avoid that. And for us, the way to do that is to just remove the idea of it being a project. It's more just something that we try and bake into the DNA of our design culture, which is just like one of our company values is lead with transparency. And so-


Charli: I love that.


Stewart: So all of our Slack channels are completely open. All of the work in progress just gets posted. Anybody can follow along that wants to see that. We have crit twice a week where we come together. And so hopefully we just have this kind of background noise of sharing work somewhat ambiently, you know? Where folks are able to pick up on things and spin up conversations on where we can potentially collaborate. And that's hopefully something that's happening continuously over time rather than, okay, this quarter we're gonna work on X, you know?


Charli: And I bet that something that you and your, like you said, your colleague who leads the product design, that's something you've led the way on and have focused really heavily on the culture side of things, because that's really where it all starts. Is there a culture of collaborating and sharing work or not? That's super important.


Stewart: We try to be as transparent as we possibly can. We have an async crit channel where folks can just post work in progress, just drop a Loom in there.


Charli: Of course, needs your own product.


Stewart: Yeah, anybody can watch that, give feedback on it. And so those are the opportunities that we try and lean into that the product honestly allows us to do, which is to really broadcast and update as widely as it needs to be without any additional effort on the designer's side. So we try and lean in to that as much as we can. And yeah, it's just about being as transparent as possible, I think.


Charli: I think it really helps as a designer when you can use the product that you're designing for as well, whether that's product design or brand design.


Stewart: Yes.


Charli: I know me as a creator, I use ConvertKit for my own email marketing. And that gives me so much more context over our brand and marketing stuff as well. So I love that you have a culture of using Loom at Loom. That makes total sense to me.


Stewart: Absolutely. I mean, we use it all day long. It's really helpful for not just being able to do the work when you wanna do it and hopefully avoid the hassle of getting everybody in the same room all the time, but it's also a way to just give quick updates. A lot of times I would just pop into a different project channel and just think, "Okay, I wonder where this is at." And I can go through the Slack channel and I can see Loom videos from however far back you wanna go. And so you can jump in and you can educate yourself as to where you're at. I don't have to go bother anybody. Nobody has to dig out a doc for me or jump on a call. I can just like... I can get myself up to speed pretty quickly. And then sometimes that then spurs ideas for, "Oh, they're doing this," you know? Maybe we should think about doing this other thing, you know?


Charli: And the public channels are important there too, because it means that, like you said, you don't have to bother anyone for a doc. No one also has to send you a link to the Loom. Like it's right there in the channel for you to-


Stewart: It's right there. It's embedded. I can see with the table where it's at. I can also see how people have commented to it. I can see the conversation that, that's spun up. And so it's this interest in system of records. Even if I'm not attached to that project, I can kind of bring myself up to speed on it. Like as in when I may want to.


Charli: Nice. While we're talking about tools, what other tools are part of your brand design process at Loom?


Stewart: The normal stuff, Figma, mostly Notion is our doc thing of choice, I guess. What else? Other than that it's really just like Slack and Loom. That's pretty much it.


Charli: Yeah.


Stewart: We don't use email at all. That's not a thing for us, which is kind of nice. Zoom, obviously, when we have to get on a call.


Charli: A real time call.


Stewart: Which certainly has plenty of value, but we wanna try and be as judicious as to when we choose to go synchronous over asynchronous. I think that's it. We keep it pretty, pretty tight. I think we use... I say I think, I should know. We use Asana for project management.


Charli: Both Notion and Figma are also featured in this season of Inside Marketing Design. So anyone listening, if you wanna know about the brand design behind those tools, you can go checkout the-


Stewart: Yeah. I love them both. You know, we just had someone build a Loom plugin for Figma that allows you to...


Charli: Nice.


Stewart: Or FigJam so you can embed the Loom videos in your FigJam hardboards, whatever it's called.


Charli: FigJam file. Yeah whatever it's called. That's awesome.


Stewart: So you can do that now. You can... Asana also. You can embed the Looms straight in there. It's kind of nice to see the integration start to happen across different tools and different companies that we work with too. So yeah, I love Figma and Notion equally.


Charli: And when all the tools talk together, that's really nice.


Stewart: Yeah.


Charli: You mentioned that part of the... Like something you focus on as the brand design team is the website and making sure it's performing. Can you tell me a little more about that? What sort of metrics do you pay attention to on the website? Are you held accountable to certain metrics for the website? I'm super curious about this.


Stewart: You know, it's been such an interesting journey over the last... I mean, I've been at Loom almost two years. And when we last designed the website was about a year ago when we did a rebrand. And at that point it was, "You know what? We're just gonna design this thing. We're just gonna launch it." What we have is so kind of bare bones, there was nothing that we can do to mess up. Do you know what I mean? Like it was... There's no way that we're gonna design something that performs worse than it was there. Not that it was doing badly. It just hadn't been fully... It wasn't being measured, you know? We didn't really know where we were at. And so really then that was about setting that foundation for ourself. Like fast forward 12 months, we're giving our website another fresh coat of paint right now and it's completely different. We have a marketing team now, you know? We have folks that are managing the traffic to the website. We're testing stuff. We're doing AA test and AB tests and ABC tests and whatever, all the colors of the alphabet. We're really focused on making sure that what we do is performing. And to answer your question, yeah, we have all OKRs that we set at a company level. For example, we shipped a brand campaign. There's a web component to that. And we're measuring, like I'm signed up for X number of sign-ups, you know? So that's a very specific metric that we wanna drive from the work that we're doing. And the same will be true for when we launch our new website. We'll be looking for X percent left in traffic or visors or sign ups or sign ups to trial or whatever those metrics may be like. We will absolutely be taking a position as to what we think we wanna aim for. And then we will measure ourselves against that, yeah.


Charli: Yeah, I love that. Web design and looking at the metrics and making improvements is one of my favorite parts of my job, for sure. I love running an AB test and seeing the results. And sometimes they surprise you, you know? And you're like, "Wow, didn't expect that one to win."


Stewart: 100%, didn't expect... Yeah. I mean, love a good test. We really wanna try and be as involved in that work as we can because when I was there. We had a whole team that was dedicated to testing a green button over a red button over a blue button, a big green button, a small blue button. All across the website we would get pages and pages and pages of reports on what's performing 0.01% bare. You know yourself, like you take all the winners and you put them together. You have a disaster of a website, you have something that just doesn't make any sense. And so I do enjoy the process of getting those inputs and then running it through the filter of, okay, what does this actually mean? And how do we wanna interpret this? And that's that for me is a really interesting part of the process.


Charli: And that's a super important part of the process as well, because as designers we still need to use our design intuition and our design training, design thinking, to make decisions based on the data. We can't just follow it blindly, because then, like you said, we end up with a disaster.


Stewart: And I think it's good also to go the other way too, Charli. We don't just have designers who are coming up with shit over their head and, "This is what I wanna do." We wanna make sure that what we're doing, that there's a reason behind it, that there's a rationale to it, and that we're able to measure how effective it is and then of make different decisions should we need to later, and adjust. I mean, ultimately like a brand, especially for a fast moving software company, is never still. It's always in motion, it's always changing. We're always making adjustments. And at some point you'll make larger adjustments than others, but it's never static. It's always changing. It's always moving. It's always... It has a life of its own in some ways. And so making sure that we are cognizant of that as the industry changes, as the product changes, I think is really important.


Charli: Yeah, we can use data and tests to check our own assumptions, you know? Check ourselves and be like we really think this is a good idea, but when we test it, it doesn't do what we expected it to. And so that's a learning we can take, you know? And apply it to future designs.


Stewart: Also the industry landscape changes, the product changes. We find ourselves in a situation now where 121 Zone from our last website design, the product has evolved so much. We've launched so many new features, we've evolved the visual design, we're offering so many different more options for expression and customization that is just not reflected in the website right now. You know? And so the reality is, is that we need to keep pace with the speed with which the product team is shipping new stuff. And that's pretty fast.


Charli: Yeah. This is why we still have jobs. Right? Because everything is always changing and there's always something new to do.


Stewart: Absolutely right, and thank God it is.


Charli: Yeah. Yeah. You can't just design a website once and be like, "I'm done with it."


Stewart: Exactly. Right.


Charli: Speaking of the website, do the designers code that? Does someone on the engineering team code that? How is it built?


Stewart: We have market engineers that we partner with, front-end specialists and that's really good for us. We're in daily collaboration with them as we kind of build our design system. We build page templates, we work on the CM... Whatever it is. We have those folks that we partner with. We're fortunate that we have designers that are pretty comfortable in code. And so sometimes that's prototyping things, whether that's how a type system works responsibly, we will sometimes prototype that stuff ourself. I say ourself, it's not me. I can't code. But we have people who are able to do that. It's what they do. And that kind of works pretty well. And they're also just able to speak the language of code with our engineering team, which is really helpful because it's not just how the thing works, it's how it performs. We wanna do a lot of nice animations on the page. There is obviously like a cost in terms of page loads and all that. And just all of those types of conversations we're just having all the time. But we're pretty fortunate to have a couple of really, really good front-end engineers.


Charli: Nice. That's great. I wanna talk through the Loom brand, because I know that you went through a big rebrand last year, right? I'd love to talk through the process of that, but let's maybe start with you describing the Loom brand. How would you describe it? And then how does that get expressed visually?


Stewart: The Loom brand is hopefully optimistic. It speaks to a new way of working. One that allows you to have a little bit more freedom, a little bit more control over the work that you do, when you do it, how you communicate. It's something that can really, hopefully, save you a lot of time and just allow you to be more efficient in the work that you do. Because the bulk of the work that we do is communication. We wanna be optimistic about that future. And so I think that's the general tone that we try and strike. The promise that we make with the brand is to bring your work to life. And that's not just in terms of you, the creator, speaking to your work in your own voice, your own expressions, your own mannerisms, bringing your work to life is also about fitting and work around your life and not the other way around. And so we try and express both of those sides of it. So yeah, hopefully it's optimistic. It's a nod to how we can do things in a better, more collaborative, more efficient way, I guess.


Charli: And there is a lot, I like that you said, bring your work to life, because I feel like there's a lot of life to the Loom brand as well.


Stewart: I mean, we went through that rebrand process, one part of which was redesigning our logo. We did all of that internally. And even when you look at that, like we call that the Loom beam. Hopefully that's somewhat optimistic. It has the circular shape in the middle and these bars or blocks literally radiating from the center. Even that it's just hopefully like a small way to allude to the fact that you, as the cam bubble on your screen is the creator, the person who brings the creative vision to life, the kinetic energy to your work, and really brings the work that you're doing to life on the screen for other people.


Charli: I love that. I love that meaning behind the logo. Let's talk more about this rebrand because I love hearing that you did it internally. ConvertKit, when we rebranded a couple of years ago, we used an agency because all of us designers on the team were like logo design, not our strength. Let's bring in someone else. How did you decide it was time for a rebrand? How did you know that this was a project that had to be taken on?


Stewart: The company was still pretty early, but it was growing really fast. And we had a website, we had a logo, which didn't really mean that much. We had like a basic color palette and that was about it. We just didn't really have the tools to express the things that we wanted to express with the brand. We just found ourself always looking for other devices, whether that's visual devices, whether that's copy or voice and tone or positioning statements. We just didn't really have them. And so it kind of became clear that not only did we need those tools at our disposal, it was also clear that this type of product, this landscape in terms of asynchronous communication was gonna be a thing, you know? And so we had to start figuring out a way to tell that story and to explain to people what that is, what role we play in that, how it can help them. And we didn't have those. We didn't have those tools at our disposal. So that was really the main driver for one to spin those things up and to really get a sharp point on them, and give us some things that we can then go take to the market and to start to tell stories about Loom and asynchronous communication in general.


Charli: And how long did this process take from the moment of you sort of deciding, okay, we need to do this, we need to rebrand, to, I guess, something shipping.


Stewart: I wanna say it was about eight months. We started it in February last year. We shipped it in October. And by saying shipping it, I mean we had basically a brand book. We had all of the foundational elements there. We hadn't built anything with it yet. We very consciously decided to detach anything that we build with the brand to actually doing the work of defining what the brand is. So as soon as we shipped the rebrand, we started working with it, we started designing our website, for example. We started designing new slide decks, whatever those things are. We didn't wanna be constrained by whatever the canvas was for any specific project. So if we were doing a rebrand within the context of a website design, that would potentially push us in a specific direction, and we wanted to try and avoid that. So we separated those things out. So from the very first meetings, which were kind of talking to the founders, talking to the sales team and the support team about Loom and how people react to it and how we interact with it, to having what we would call like a brand book that we were then able to start building with. It was probably about eight months.


Charli: Maybe it's because I'm not a branding expert, but my general approach to forming a visual brand around something has been to, well, let's just see how it would work on the website and what other things I would need. And I do take that approach. So tell me how the design process went for designing the Loom brand then since that wasn't the approach you took.


Stewart: So it was a few different phases. First phase was like a discovery phase, which was like I say, talking to people, kind of understanding the experience that customers have with Loom. A super interesting data point on that early on was the experience that the sales team have when they're demoing in Loom to a prospect, and that is they take you through the experience. And then they realize that when you click, "stop recording", the link is already generated instantly and it's been working in the background, and that's a magic like aha moment. Because normally when you do that with video, you have to sit back and wait for 10 minutes for it to render.


Charli: And come back later and then you forget about it.


Stewart: So you don't do that and that's this magic moment. So that was like a really interesting early insight that we got around the potential power, the speed of the product, how efficient it is. There's a discovery phase there. Then there is like a synthesis strategy phase where we start to bring some of those concepts and those insights to life. That was through our brand promise work when we landed on Bring Your Work to Life. That was the first creative statement, groundwork, whatever you wanna call it, that we had in place. And then that was then what started to inform the visual design system that then flowed from that. And the visual design system then became how do we wanna represent Loom? What's the visual representation of a Loom? Of the process that you go through as you're using it, as you're sharing it, as a viewer, as a creator? And so there are variously conceptual pieces to it. And so I think that's where we really started to focus for a long time, was like the conceptual space. Like how do we do this and shapes and colors and motion and type. And then the idea being that once you have those things, you can then start to construct them. You can put them together in different ways. One of those ways might be on a website. One of those ways might be in a slide deck. One of those ways might be in motion or animation design. As we went through, we started uncovering those devices. And then at a certain point in time, we felt like we had enough understanding of those to be like, okay, now we're gonna design a logo. That was a specific output, which had its own process and it's own energy and momentum, but it was all driven from the discovery and the strategy and the creative concept and idea that we'd done previously. Actually I started to count how many logo options we'd done and I stopped at around 2,500.


Charli: Oh, I was gonna be like, wow, 25, and then you said 100.


Stewart: 2,500 and I'd stopped because I was nowhere near close.


Charli: Wow.


Stewart: There was just like a lot of potential directions, going wide, going deep, narrowing in, going wide again. I don't know. It was an interesting and fun process.


Charli: Yeah, tell me more about how you and the team worked together on this. You're talking about like coming up with the brand statement and the brand elements and figuring out could this be applied to a website, to a slide deck, whatever. How are you working together on this?


Stewart: We did a lot of what we would call creative jam sessions, which was we would get the team together for a whole day, sometimes two days, and you can't spend all that team on Zoom nor would you want to. We would set some prompts. So we would break it into like really small pieces. Take color, for example. We'd be like, okay, for the next day we're gonna focus on color palettes and how we use them and how we combine colors and what we wanna see with them. We would give the team prompts that we would discuss for an hour, maybe a little bit more. We would just have an open conversation about it. What ideas does this spur in? How do we think? And then we would just go off individually and work on those things. We would come up with some solutions, some options, some directions, sometimes it was maybe just a mood board. Sometimes it was starting to put things together and play with them and see how they felt. Then we would come back together at the end of the day, synthesize those, decide what we liked and what we thought we wanted to take to the next stage. And then the next day we would come up with a different prompt. And we would overtime start to uncover solutions. We would gradually start to narrow in on what was feeling good. And when we had that, we would then do more prompts based on that. And so it was just kind of this gradual process of coming together, discussing things. Nothing's off the table, going off and working on it individually, coming back, talking about it, and then deciding how we want to edit those inputs and what we wanna take to the next stage.


Charli: So it really was a team collaborative experience rather than like a divide and conquer, where it's like, okay, you're gonna figure out colors. You're gonna figure out type. Talk to each other as you go.


Stewart: Exactly.


Charli: Like everyone was working on it.


Stewart: Everybody who was working on everything. And I think what the cool thing about that is, is everybody has slightly different skill sets, comfort levels with tools. Like our strategist, for example, is not a designer. He wouldn't mind me saying that. So he would typically come with words and images that he'd found elsewhere. Our producer would come with references to movies or TV shows or whatever it may be. And so we would bring all of these things together and combine them with some of the tape work or the color work or the illustration work that the designers had done. And it would start to paint this interesting tapestry. And a lot of times we would get to a solution that we felt really good about. It didn't necessarily have a form to it yet. It may just be words, it may just be maybe shapes, maybe not, but maybe reference these to cultural moments or memes. There was a lot of just bringing in a whole different bunch of references to try and illustrate what we were trying to see. And so I think it was cool to have everybody just express themselves in the way that they felt most comfortable. And that's not always just designing something.


Charli: Yeah, yeah. It doesn't always happen with pixels on a page either. I love that because I had totally assumed that the people who were actively working on this was you and the designers. So I loved that the whole brand design team was involved in it and that everyone's opinions and thoughts were taken into account.


Stewart: Absolutely, and you know, at a certain point we were like, okay, we need a type system, and how does that work responsively across the grids and how does that work in product? Okay, let's bring in the product. At a certain point we start to focus in on whatever, in the details and what our areas of expertise are. But that's like more of a... It's almost more like a tactical thing. We all kind of knew what we were doing then. It was really just a case of going and executing that and bring it to life. We'd already done the hard work of trying to figure out what this thing is that we wanna do.


Charli: Is that a general approach that you tend to take to a lot of projects at Loom? Is being more collaborative or like, say for example there's a new landing page that's needed for the marketing site, will that be assigned to one designer and they'll work with marketing on it? Or is it more the team?


Stewart: I mean, we will have a lead designer on it, but we do try as much as we can to collaborate on these things. It depends what it is. Like if it's a bigger project, if it's something which ultimately is like part of a system the other designers are gonna wanna use, we do try and bring people together at certain points to collaborate on those things. Sometimes it's just a tactical thing that needs done, that's built on our system that we already have, in which case somebody can just go work on that and then share their work as they go. So it depends. It's a little bit of both. We have a standup meeting every morning where we're generally just cheering what we've done the day before, what we're gonna do today. And then through that process or sometimes we're like, you know what? We can do with maybe getting the team together for a few hours or a day on this thing. Maybe it just needs move forward faster. Maybe it has implications for work that somebody else is doing. We try and involve everybody as much as we can in those moments.


Charli: What I want everyone to remember as well as the hearing you describe this collaboration process, is that all of this is happening remotely.


Stewart: It's all happening on remotely. It's not that we try and limit our Zoom time necessarily. It's more just like we wanna try and give designers time to focus and get into flow state. The worst thing that can happen is that you have 30-minute meeting, 30-minute free time, 30-minute meeting, and have that all through the day. So we try and have our catch up first thing in the morning. Then we go off and just get our heads down for a while. And if we feel like we need to come back and work on stuff together, we can maybe do that a little bit later in the day. Or we can just schedule that for a time where, okay, you know what? This is gonna be a synchronous time, you know? And we're gonna have like three or four hours together. We're gonna work on this. We're gonna come out with some kind of solution and then we're gonna go off and do our thing. So yeah, it's all happening remotely. And really the remote piece is really us making sure that when we do come together synchronously where as if we're using that time as efficiently as possible. A lot of times we'll send a Loom beforehand, which is the prompt for the meeting, or here's the pre-watch. If it's a design review, we'll record a Loom, here's the work, you know? And when we get together, it's about dissecting the work and getting the feedback that we want, we doing. We're not presenting that in real time. Hopefully everybody's had a chance to look at it, think about it and then come to the meeting with their perspectives. And that hopefully keeps everything a little bit more efficient.


Charli: Yeah, so it's like this mix of asynchronous and synchronous that is leading to this cool collaboration you've got going on. We've talked about a lot of the things that are working well at Loom obviously. What are some of the main obstacles that your team are facing the moment or things you're working through? Or maybe it's just like an area of growth for you where you know it's a place that you want yourself or the team to improve?


Stewart: I think the thing that's always hard is just the speed at which... This is the same at all kinds of companies, the speed at which we grow, the speed at which we're shipping new product, new features. We're doing that fast. We're shipping new stuff every month. The timeline with doing that is slightly different to how the system evolves over time. Sometimes we find ourselves in a situation where... I mean, take this as an example, we've started doing some tools for video creators, which is virtual backgrounds, what you would call canvas templates, which not everybody wants to be full screen if they don't have anything that they're actually showing on their desktop. So we'll give them some templates to use as like a background. We're doing a lot of that. People really love them. We haven't done as much work as we probably want to on our illustration principles and how we actually bring illustration to life within the context of the Loom brand. And so we find ourselves kind of having to think about, okay, how are we gonna approach this current project? And then what do we need to scale this over time? This is the principle that we don't have right now, and that we probably need to figure out because we're gonna do more of this stuff. So sometimes the speed at which product ships can overtake the principles that we have on the brand side. And then we need to take a step back and think about how we may wanna approach that and catch back up to where they are. So sometimes the shipping cadence and product can be slightly overstep with how we think about evolving the brand over time. That's just generally how quickly the company, the teams, the industry landscape moves, is definitely a little bit of a challenge.


Charli: Yeah, totally. And then to end on a super positive note, what is something that you are most proud of?


Stewart: Honestly, just how much fun we have together. You know, I think like the work is cool, but really the thing that gets me up in the morning is the people that I get to work with, the fun that we have. We don't take stuff too seriously, you know? It's only software. Do you know what I mean? Like we're not curing cancer here, we're designing websites. And so we wanna try and keep that in perspective and while, of course, we wanna put this disclaimer in for if the CEO is listening, of course, we wanna build a large company. We want to build value for our customers and ourselves. We definitely wanna do that, but we also wanna have fun doing it, you know? And if you can't enjoy the process with the people that you get to do it with, I'm not sure what the point is. And so I think the thing that I'm most proud of is how much humbleness and lack of ego that we have, not just on the team, at Loom generally. I think people who are genuinely curious, interested in each other, willing to help out, to collaborate, to try new things, to fail to try again, and just have a bit of a laugh doing it. I think that's really important.


Charli: I think that, that shows that's, I mean, related to several things you've said throughout this episode of the bringing the life, right? To your work. That's one way that you bring life to work, is just being real and having fun, having a good time.


Stewart: Absolutely. That's 100%, right. I will never rerecord a Loom. I will always... Like if I mess something up, if the dog's barking in the background, if the doorbell rings, I will leave that stuff in. That is gold, you know? That's the stuff that I really love. And I love even asynchronously been able to get those little insights into what's going on in everybody else's life. And so that's kind of what we strive for, that transparency, that honesty and that kind of openness. That's what makes it fun to show up to work everyday.


Charli: Yeah. Agreed. Well, thanks so much for everything that you've shared about design Loom.


Stewart: You're welcome, Charli.


Charli: I am still reeling from the idea of grading 2,500 logo options, and I'm super grateful to Stewart for sharing so many insights into that redesign process and everything else the brand design team at Loom works on. You will find links to follow Stewart on Twitter and also to check out Loom in the description. And if you want more episodes of this show, they're all on InsideMarketingDesign.co. We are over halfway through season two now. So if you've been enjoying the episodes so far, I would really appreciate it if you'd leave a review on Apple Podcasts to recommend it to other designers. Thanks again to Webflow for sponsoring the season. Thanks to you for listening. And I will see you next time.

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