S2 • E2 – Oct 05, 2021

Inside Marketing Design at Help Scout

with Lead Brand Designer Matt Plays

with Lead Brand Designers Matt Plays and

with Lead Brand Designer Matt Plays and

Content is a priority to Help Scout, as is great imagery and design to accompany that content. In this episode you'll get the lowdown from Matt on the design process behind Help Scout's latest publication, In The Works, as well as insights into the team structure, processes and priorities that allow the team to produce high-quality work.


1:30 - About Sendible & today's guest

3:10 - David's role & responsibilities as Brand Marketing Manager

5:40 - What David works on day-to-day

9:00 - The Sendible marketing website

13:00 - Marketing at Sendible

15:00 - Sendible brand & messaging

18:50 - The web design & testing process

26:10 - Tools & software

27:25 - Why David does his own photography

29:15 - Measuring success & data

31:10 - Project management

32:45 - Designing social media images

35:55 - Design system & staying aligned with product

37:50 - Challenges David is facing at the moment

39:40 - Planning work in 2 week sprints

42:35 - The impact of marketing design at Sendible


Charli: Welcome back to Inside Marketing Design. I'm your host, Charli Marie, I'm the Creative Director at ConvertKit. And on this show, I'm giving you an in-depth look at the marketing and brand design processes and principle, and projects at various different tech companies. And today I'm speaking with Matt Plays who is the Lead Brand Designer at Help Scout. Help Scout is an all-in-one customer service software platform. And it's a company whose sense of design I've admired for a really long time. So obviously I was very excited to talk to Matt and get the behind the scenes info on how the design process works at Help Scout. There are a little over a hundred people on the globally distributed Help Scout team at the moment, and Matt's been a part of it for almost three years. 

We had a really great conversation about the high quality bar the team have set for design and imagery, and how they reconcile that with the volume of output needed by a busy marketing team. We also dug in on Matt's latest design project, the new publication, In the Works, by Help Scout. And we got very nerdy and very detailed in some places about components, and systems, and stuff like that. So, if you like that sort of thing, I think you're really going to enjoy this episode. 

Before we get into it though, I wanna say a huge thank you to Webflow for sponsoring this season of Inside Marketing Design. Webflow is a tool that allows designers like us to build production ready experiences without coding. It's got a really powerful CMS built in that lets you work with content without dealing with any database management and annoying things like that. And that's just one of the many reasons why it's a great option for marketing teams. I use Webflow to build the Inside Marketing Design site and I always highly recommend it to every designer for their personal website or portfolio, and really to any designer needing an easier way to bring their designs to life on their own. So you can check it out at insidemarketingdesign.co/webflow. Now, let's get into it and hear from Matt about marketing design at Help Scout. 

Welcome to Inside Marketing Design, Matt, really excited to have you here because I have been a fan of Help Scout's marketing design for many years. I think I already told you this, but it's one of the websites that I visit when I need inspiration or if I'm like, okay, how do I structure this content on a page? Let me see how a Help Scout does it. And I like to reference it. So I'm excited to be digging in today on this with you.

Matt: Well, it's a mutual feeling with you, Charli, so it's thanks for having me. I'm stoked to be here.

Charli: Cool. Let's just jump right in then. And first talk about the design team structure so that we get a sense of who's working on all this cool design stuff. So tell us a little bit, what does the design org look like at Help Scout? What team are you on? Who do you report to? Give us a lowdown.

Matt: Totally. So, it's funny. We are like a big design team when we think about product and brand. For product, we have a director of product design and four product designers. On brand, we have a director of brand, three brand designers, three front-end developers, a contract illustrator and freelance where necessary. So we come together and keep in touch as a design team at large, but at the same time, we're a pretty cross-functional brand now that actually sits within marketing. So most of our projects, if not, the majority of our projects come through marketing, we also obviously overlap with product when brand finds its way into product as well. So it's kind of cool to sit at that intersection of both and stay in touch with, you know, both teams and feel kind of allegiance to both teams. So, it's cool.

Charli: And you report to the director of brand and then the director of brand then, does it come into sort of like a wider growth org or a design VP or something?

Matt: Currently, director of brand reports into marketing, I believe, into the VP of marketing.

Charli: Yep, cool. So yeah, it's really this brand and marketing collaboration and combination that you've got going on there, which is cool. All right. And you are now recently promoted to lead brand designer, which is really exciting. Can you tell us a little bit about the responsibilities that you have as part of your role? What are you responsible for?

Matt: Really psyched to be a lead brand designer here. It's like a, it's still an individual contributor role. So my main contributions are still to do brand projects and web design for the company, which is what I know, where I offer the most value to the company. So I like being here. I think the additional things that I'll focus on is creating tooling and processes and, you know, systems that other designers can leverage to keep our work feeling cohesive, and kind of elevate and create equity in the work that we're creating. Besides that, I think it's also just focusing on, on the environment and the processes that make work more efficient and more enjoyable for everybody.

Charli: Cool. That's exciting to be in that lead role and, you know, be contributing in those ways. I love it. So you mentioned brand projects and web designs as the main things that you work on. What about the wider brand design team? Is there other projects that come into it that other designers on the team work on?

Matt: Totally. Yeah. Our team is actually full of a bunch of really T-shaped individuals. I feel like everybody can do just about anything, but we all have, we go deep in certain areas. So we have a couple of folks on the team who are really good at illustration or/and could be 3D editorial illustration and art directing others who if we have to outsource, I think those individuals can do that really, really well. We've got people who are good at UI and layout, and we've got people like, where I go deep, I think is in brand typography, photography, and color and things like that. So it's cool to see that we all have, there is a spectrum of capabilities there, and I feel like that helps us serve all the different areas that our team needs to deliver.

Charli: Yeah. It makes you like a well-rounded team as well. You know, so there's always someone to specialize in what's ever needed. You mentioned that you feel like a really good intersection between product and brand as well, and that you collaborate when needed, because you're part of this wider design team. What are some of the ways that you do end up working with the product team and how do you facilitate that connection for collaboration?

Matt: One really cool instance of us collaborating in recent times is we're actually working on a major feature release at the moment. We had to brief our product marketers and we kind of were feeling as though we needed to gain a little bit more understanding on the brand design side for us to create our deliverables. So we actually linked up with the product designer who created the feature, and had her join one of our meetings to kind of give us a presentation and just to give us a general understanding of what's the “too long didn't read” of this feature. So, 'cause that just really helps us if we have our comprehension at that level, then we can distill it and we can make it easy to see at a glance. I think without that bridge, it makes our job really hard. So, I think we're probably gonna lean in and do more of that. I think it was super successful and just really created clarity for our whole team. I guess it is a little bit of a spontaneous thing. And we kind of encourage that type of pair designing and things that, as needed, we can kind of create those spaces, create those conversations. So that way we just make sure the right people are in the room to create understanding and collaborate where necessary. So I think a lot of it is informal like that. The one formal thing that we do right now with the greater design team is we do a monthly fika just to make sure there's kind of this cross pollination of ideas, but really a fika is usually a fun, social time. And I think everything else happens just as needed on an organic basis, which is pretty great.

Charli: Right. So there's not regular, serious critique times where someone's presenting. It's more like, when you notice you need feedback from each other, you'll meet and do it. Is a fika, as I know it is like a, is it a Swedish thing, that is like an afternoon tea or something? Or is it an acronym for something that I'm not understanding?

Matt: No, a fika is, as I understand, it is like a Swedish coffee date or pastry date, and the idea is, is to usually not talk about work. I mean, sometimes you find your way there, but at Help Scout, we have even a Slack tool that will pair you with a random Help Scouter to suggest that you have a fika and get to know folks, take the time, especially because we are remote-first organization, so to take the time and do some of that water cooler talk, and be social, you know, get to the person behind the work. So it's a really, really cool thing that we do.

Charli: I like that. And that is so important. I agree. I don't think we can do our best design work when we don't have all the context. So like you said, wanting to better understand the feature that was being developed and that you were, I assume, was creating a landing page or like marketing materials for, and also the people working on them, right? Like those interpersonal relationships are so important, especially in our remote setting, you've got to work extra hard to build them up.

Matt: A hundred percent. We also do a couple other cool things that I think help us passively check in on what other folks are working. One thing a lot of the design team does, we maintain these design daily paper docs, that way you kind of just record what we're up to and there we can leave, like, something that we're proud of, a screenshot of something that we like, a link to Figma, a link to a prototype or a Loom video. A lot of folks, again, since we are remote-first, recording a Loom video to just, even just share what you're working on or more formally, present a whole phase of a project. I like to share that and I know other designers do, and I'll watch others to kind of stay in touch with them, even though I haven't chatted with them in months, I feel like I know what folks are up to, that energizes us and it's just a cool way to like passively check in on people who might be in different time zones, on different teams. And you just get to stay in touch in that cool way.

Charli: I love that you do that. That's a really great way to asynchronously critique or stay in touch. And side note, spoiler alert, Loom is also gonna be featured in an episode in this season of Inside Marketing Design. So, everyone stay tuned for that. Cool. You also mentioned, so one side of it was connection with product. There's also the connection that you have with the marketing team. What are the main ways that Help Scout markets its product?

Matt: For the most part, the things that our team ends up working on for product marketing is either feature pages, core feature pages on the site, or potentially a specific landing page for a campaign for a feature launch. We also do blog content and things that are product specific things that find their way onto the blog, like release notes. So our team oftentimes will help kind of bridge the gap between product and brand by bringing those and formatting the screens for the blog, and simplifying that, kind of abstracting it, and making sure that it reads well in that context. So that's kind of some of our main deliverables when bringing kind of the product to market.

Charli: I love that you called out the, like simplifying product screenshots and making like, there is so much work that can go into a good product screenshot, right. It's more than just take the screenshot, paste the image. There's so much more to it than that. 

Matt: Right. It's art, not science for sure.

Charli: Exactly. And like sometimes a little bit of like, you know, fakey fake and changes going on just to make things easier to see. Content I know has always been huge for Help Scout, right. I think I probably heard of the Help Scout blog before I even knew what the Help Scout product was for example. Talk to me a little bit about that and especially the way that you all invest in imagery and design for content. Because for me, that's part of my job where I'm like, oh God, okay. Making an image for a blog post is not my favorite thing to do, would rather avoid it if possible. In fact, I hire freelancers to do it most of the time, but how do you all approach that? And talk to me about your illustration approach.

Matt: I think a lot of this has happened well before I joined the company and I kind of came in and joined largely because this, you know, atmosphere existed at the company. At Help Scout, brand is seen as a differentiator. So we have permission to invest in things like that, which is really, really cool. So we've already had a high bar for editorial visuals on the blog when I joined, and we hired people accordingly who can either deliver on that themselves or can outsource and art direct other people as well. I think we see it as an opportunity to extend the concept of the piece, and kind of bring that to life in a visual way. And ultimately, now that we've kind of invested in this route, we kind of make sure that we can kind of uphold the standard that we've set for things. And we also find ways where possible to create systems that make us more efficient. So we definitely do try to prioritize certain posts that warrant a freelance illustrator versus something that's done in-house, using a house style, or something that's a little bit lighter lift and systematic. So there is this cool spectrum in this like editorial content space. And we just have permission to kind of invest in it and make sure that it's, you know, at a reasonable bar across the board, it's really, really cool. And I think the organization has our back to do it.

Charli: Yeah, that's great to hear. And I think it comes through, right, in the Help Scout brand. How do you decide which pieces get the, you know, the freelance treatment versus the in-house treatment? Is it ones that are around certain like cornerstone topics or that are expected to reach more people? I don't know. What's your thinking there?

Matt: I feel like that's a conversation usually for the editorial lead of the content outlet and the art director who's on the case. I do think there is this idea of like, what is a utility post and serves more of a certain purpose, and what we do expect to have some reach. And so I do think there's a scale that can be tipped in either direction to decide how much effort goes in. There is sort of a tiering treatment and system. So that's a little bit outside of my realm. I get to see it from afar, but I do know we have that degree of sophistication. Folks do it in a way that sort of gives us the right amount of effort and the right amount of ROI for the effort that goes in.

Charli: Yeah, 'cause that's so important too. This is the reality, that you can't make everything the special favorite child, or whatever you want to call it. You got to play favorites at times and you've got to like, I don't know, treat some things as more important than others 'cause otherwise you'll burn yourself out trying to complete everything to like the ultimate high standard.

Matt: Right. If everything's volume 10, nothing's volume 10.

Charli: That is a great point. And nothing can be volume 11 either because you're putting all your effort into everything being volume 10.

Matt: Right. Yep.

Charli: Well, okay. Now that we're speaking about content and about the importance of it for Help Scout, can we dig in a little bit into In the Works, which is a recent project that you shipped and it is beautiful. This is one of those designs that just like, quite honestly, Matt, it made me jealous. I was like, man, I wanna be doing stuff as cool as this. This looks amazing. Like it really pushes me to, you know, up my design skills as well. So I appreciate seeing work like this. Give us the lowdown on what it is and talk about where it started, why Help Scout wanted to do it.

Matt: It was a huge project and it was a huge gift to me as a designer to have sort of this blank slate, and our whole team as well, this whole blank slate opportunity. There's so much legacy that you have with an existing brand, to start a new is a real gift and you get to try some cool things. But I think the reason we got this going, again, speaks to the fact that the organization, from top to bottom, really cares about good, genuine content, and wants to invest in it, and knows that creating it and creating something that resonates with builders, and makers, and people with this kind of grounded entrepreneurial spirit, those are the kinds of people that like our software. So we want to make content for them, and we want, you know, to resonate with them. So I think it's this, it's creating that space where all of that can happen because I do think that ends up being like the intersection of a really cool Venn diagram.

Charli: Totally. So you had a blank slate, you said, for the brand of this, was it totally blank? Did you get a brief from anyone of what this site should look like, what the brand should be for In the Works? How much detail?

Matt: Yeah. Nothing's ever totally blank. 'Cause we do, I mean, again, we're a remote company, so documentation's paramount. So we do have our brand values documented fairly well. And we do actually have an approach for microbrands that aims to make sure that we keep our brand values intact. We might sort of bend and like focus on one of them more than another, and lean towards a certain audience or persona more than another value. But I do think we ultimately try to keep that in mind as our like North Star, or set of North Stars, and make sure we never violate them with anything that we do. And I think that ends up making things that feel like great offshoots at the Help Scout brand, but never something that feels totally different or alien. So I think that's, that kind of just, the fact that we have those principles and have something to kind of compare ourselves against, just keeps us in the right zone of like brand to microbrand. We stay adjacent, we never feel different.

Charli: I love that. How much can you share with us about what those values are and what the guidelines are, you said for microbrands? Definitely keen to hear more about that.

Matt: Yeah. I don't know how much the microbrand documentation is public, but you know, our brand values are on style.helpscout.com. So, you know, we're human and organic, trustworthy, helpful and things like that. And that was actually one of the first projects that me in my season of being here at Help Scout, our team worked on was kind of documenting our brand values and some of the other voice and tone, and brand asset things that you see on style.helpscout, but that has informed so much of the rest of the work that we've done as we've grown since that day in a really, really cool way. So it's cool to have that foundation to build everything else on top of.

Charli: And it does help to have some constraints, right. 'Cause I don't know about you, but a complete blank slate is a little bit, I get overwhelmed by it. Let's just say that.

Matt: Absolutely. Having that reference point gives us a way to show, like how, what if we pivot by a few degrees from that? Like what does that look like? What does that look like when, through the lens of this new audience or persona that we're looking to resonate with? Like how how can we bend it? And I think at least having that reference point keeps us from just creating something random.

Charli: Yeah, totally. That's a really good point, but I guess something like trustworthy can mean something different to different audiences. So that's interesting what you said, of like, you know, you think about the audience and what that brand value means to them, and try and reflect that in the design.

Matt: Yep. Yeah, it does. It helps us have that additional layer. And I do think we, one of the first things that we did, we did some discovery early on, but we did hire an editorial lead for In the Works. And she had a vision, some of the first exercises that we did were in regards to brand values of In the Works and then also down the line to naming exercises. And that was team-wide. So if you were a writer, producer, designer, engineer, you were in that call participating in that meeting. And I think that really helped us also set this foundation for the values of the brand and how that might manifest visually. And then later, like actually naming this thing first or whilst creating the brand direction, really helps because you start to see, does that match, does that feel right? And I think that's a huge part of the process. So when we got into doing our brand direction, we did kind of four rounds of it. We were probably playing with only three or four names and creating a visual directions with those names. And I believe, maybe a few alternates in there, but I believe we have our visual direction and the name in one of those like first four directions that found its way and was refined all the way to what you see now.

Charli: That's cool. You were onto a winner right from the start.

Matt: Close. It had a little bit of dust to work through, but.

Charli: To brush off the corners. Yeah. I like that you had a meeting with the whole team to talk about this too. 'Cause that again just shows me the value that Help Scout places on this project, right? Like if it's worthwhile enough for the wider team to be talking about it, that means it's important, and it's not something just like, the brand teams do an off in the corner over here and working on by themselves.

Matt: Right. Yeah. We had a Slack group and a regular weekly, and sometimes twice a week meeting with this core team, and they were all considered stakeholders of this project. So anything that we came to the table with, from a design perspective was viewed by this whole team. I think that ended up, they were true partners throughout the process. So I think that's yielded up a finer result that everyone's really psyched on. And I think everybody has a little piece of too. So. That's super cool.

Charli: That's cool. I was just going to ask you, well, who were the stakeholders in the project? So there we go. You just answered that question for me. Let's move on then to the end of the design process of In the Works, you've got a finished design, how do you bring it to life? Who codes it and what does that process look like?

Matt: Again, we had this opportunity blank slate. We get to try a few different things in this project. One thing that we did in In the Works that I think is cool and we'll certainly do again, is we brought devs in much sooner in the ideation phase. We actually had a few sessions where we were just bringing in reference material together and we even had a board in Figma where we called them moonshots. And we just put a bunch of sticky notes. And I really enjoy like when you have a blank slate to try to create opportunities for things you want to say, sneak something cool into the project, because I think that's where the fun is and that stuff creates the light in the end result. So we actually created moonshots and developers and designers were all creating them. And I think probably 80 to 90% of those were implemented on the site. I don't know that they would have been if we didn't kind of conceive of them together, those are the kinds of things that nobody asks you to do. Like this selected state or that we want the audio player to be persistent throughout the experience, when we're talking about podcasts and listening posts, those are things that we thought would be really cool that might not come through in a brief, that might not come through as a requirement, but I think add up to something cool in the end. So it was really cool that we got to do that. And then throughout the process, I think we, again, since the developers were just as much a stakeholder as the VP of marketing, they would see every step of the way as we built out components in Figma and much of this with the overlap, they were building while we were designing. And eventually we reviewed things, kind of component by component, you know, chipped away at that list, which at times, my hopper of PRs to review was huge at times, dev's hopper of things to build was huge, but we kind of worked through it and in a few phases of like design and building, we got it done.

Charli: And you you've mentioned some plurals in here when you talk about devs and we working on it, who was actually involved in designing and developing? How many people were working on those parts of it?

Matt: Yeah. So for like the website design, I would say there were about three designers working on web design itself. And we have three developers as well. We had, our team, when we started the project in March, had one developer, and we lucked out and hired two other front-end developers who were amazing, who joined halfway through this project and really helped us carry it through to the end. Our first front-end developer actually went on parental leave and the handoff was literally on the same day, they never saw each other in the office. So it was a really cool opportunity to, you know, onboard them and start like, with a really, really cool project that, you know, we lucked out, that they really enjoyed the process, and it kind of held us designers to a really high standard to make sure too that we were doing all the documentation that we could to make sure that that was as seamless as possible. But it was really, really cool. And the fact that we have three developers on the end of it, at the end of it is really cool.

Charli: Yes. I'm very jealous about that. That's for sure. How do you decide between the designers, who works on what? That's something I'm really curious about. When you're all working on this one project, how did you split it up?

Matt: Yeah, that's a great one. And it's something that I feel like I have to anticipate some of the things that might go wrong in this process and what might make, you know, at the tail end of it, when we're building this, like what might make that more complicated than it needs to be? So, we front-loaded this project with a lot of design system work. So as soon as we got our brand direction approved, we started creating a design system and library in Figma. Another really useful tool, it's kind of a totally in the weeds thing. So I hope the audience is ready for it.

Charli: We're ready for in the weeds. This is the point of the show. Go for it.

Matt: One really cool component that I worked on was just this spacing unit component. So I wanted to standardize our spacing throughout the project. So that way we could just stay consistent and not have to juggle values mentally or have them documented. We were actually using a component. And so the component has so many wild variants. I found this old blog post by a studio called The Scenery and they were somewhere out in the Midwest, and they talked about using the Fibonacci sequence for their spacing units. So it would be the two proceeding units equal the next. So if one is 10, the next is 20, but the following one is 30. The following one is 50, you know? And so on. What that ends up doing is it creates like meaningful gaps between them. And I found that makes decision making easier, one spacing unit when you're talking 160 versus 100, one is right, one is wrong. Those are big differences. You can easily tell, like what is the appropriate thing to do? So we did that as our base for sort of a desktop viewport. And we actually then multiply that by a ratio. This is where I kind of added to that idea. On mobile, we halved that. So those units were halved, and on extra large screens, those were multiplied by a factor of like 1.25. And what that enabled us to do is, is basically we had these checkpoints where pixel values are super round and we can create comps for them. But ultimately we created a set of variables that developers used in code as CSS variables that we were able to just really reference semantically. So we could say like, this is a medium, like this grid has medium gaps. The padding of this section is large. Like, and we got to be really, really consistent with that. It was a lot of front-end work, but I think what that ended up doing was it gave us all the same pieces to work with. So we're creating components with auto layout, zero spacing, and we're literally using these spacers in our auto layouts. There's a toggle if you want to toggle them on for visibility, or off, you can do that as well, which is kind of cool, but that enabled us all to stay in sync. And then it made delegating components really, really easy to do. So once all of that foundation was set, I felt like it was easy to say, "Hey, like take this whole page or take this whole section and component, and work on it in isolation." And it's going to, because it's referencing type styles from the system, and spacing units, it's going to look like it came from the same desk.

Charli: And it's going to fit in, even if you're not doing it, designing it in the context of the other stuff. 'Cause you're all pulling from the same language. Yeah.

Matt: Yep. And you know, if things needed to change, they could change globally because they certainly did. We'd be wrong about a ton of things, but then you could change something and it would affect, it wouldn't create outliers, it would actually keep things more consistent. And so we lucked out by putting in that little bit of extra work upfront, and I think that enabled us to spread the wealth, 'cause there was so much work to go around and we couldn't have done it without the whole team working on it. And I think everybody enjoyed that part of it. It was cool.

Charli: Yeah. It's fun too as an in-house designer to take a break from the main brand for a little bit and go work on a sub-brand like this, a new design system, I love that you got the opportunity to do that. And also, it is very clear from hearing you talk about it, why the design ended up so good because of all his attention to the details, right. So I hope that's the takeaway for anyone listening. I know I certainly don't think in systems for my spacing, and so maybe that's what I got to work on if I want my designs to look as good as In the Works. You know?

Matt: I think it's the fact that we had this blank slate that we could do it. It's the fact that we've wanted it for so long, but it's hard to implement, you know, so it's cool to just seize that opportunity. I am a hundred percent sure you could do it.

Charli: Thank you, thank you.

Matt: And there's also a total dark side of that coin where you do too much of that. You do have to like take the step back and look to be sure that, just because it's a system doesn't guarantee that it looks good. So you do have to like take it with that grain of salt. I think having that self-awareness also helps audit whether the decisions you're making are good or not.

Charli: True. Do you think you'll be wanting to take some of these learnings and ways you approached In the Works over to the main Help Scout brand now that you've had that experience?

Matt: I would love to, and we've already begun talking about the things that we'd like to take over. I think some of the variables that we created that work across viewports really lessened the amount of review that would need to go into each component, because, ultimately, when those variables work out of the box, it's really nice that we don't need to look at type sizes as much on small screens or the spacing. The spacing doesn't become too much on a small screen because that variable already considers it, and already tends to it. So we would love to bring some of that back because as we get back into Help Scout projects, some of those things don't exist, and we're already feeling we would love for those things to exist. So, I do think, you know, we have sort of another moonshot to kind of bring some of the good stuff back for sure.

Charli: Cool. And maybe that's like part of your role now, you know, as lead brand designer too, to be working on those things.

Matt: Totally. Yeah. And having, so Mark, our first front-end developer did just come back from paternity, and we're super psyched to have him back. And we're now beginning to kind of divvy up the new documentation that we want to do, the things that we want to bring back. And I think now we have the sort of the time to implement and consider what's worth prioritizing. So it'd be really cool.

Charli: That's awesome. So now that In the Works is out there and launched, I really want to talk about success metrics and how you measure the success of a project. What sort of metrics you're responsible for as a designer, and maybe we can use In the Works as an example, you shipped it, what was success for In the Works? What sort of things were you looking for? You don't have to share numbers if you don't want, we just want to hear what sort of things, what metrics you're paying attention to. What are you measuring?

Matt: So when we get a brief for a project, every brief comes in with an ARPA, which kind of identifies who's responsible or accountable, responsible, a participant and an advisor. It's a fun acronym that kind of creates those roles and responsibilities for a project. And we also identify like kind of the metrics and the goalposts that we're looking for. For In the Works and any project that we do, we usually have, it usually funnels up to an OKR. So In the Works is the one that spans several quarters. So, kind of creation of the brand and the art direction rolled up into one quarter's OKR. And then the creation of like issue one and the website, kind of rolled up into the second quarter's OKR. Within that, we have other, you know, goalposts and metrics that the team is after, but we have, you know, design is a participant in that process. So for every brief that we get, we have an ARPA which kind of assigns roles and responsibilities for the project. And I think design is usually in that participant and responsible level. So we do what we can to deliver on the strategy, to achieve those goals as best we can. For In the Works, we were focusing quite a bit, I mean, quite a bit on brand affinity, and awareness, and viewership as well as subscriptions. So those are the things that we're really keen on getting people, you know, on the site, subscribing to get updates and continuing to make that process easy for our content team to kind of keep that train rolling. That's kind of how we roll into it. So I feel like we are never directly responsible for those metrics, but we feel a hundred percent indirectly responsible, and like as huge partners in that process. And that informs so much of our work.

Charli: Right. So it's like you personally, as a designer or/and the others aren't, you know, held accountable to these affinity awareness signup goals, but you're responsible for helping, I assume it's marketing and like the content team were the ones accountable for it. You are responsible for helping make that happen.

Matt: Absolutely. Yep.

Charli: And the affinity and awareness you talked about, this is something that we try to measure as well, and it's so hard to measure. And is sign-ups one of the way you measure that or is there other ways you measure affinity and awareness?

Matt: That's a good question. I know, subscriptions definitely are a cool way to measure that. We do have folks who are tracking engagement across other channels and social and things like that. Some of it does seem to be anecdotal as well. Like, we are okay with doing some things as this brand play. We know that it is a long-term investment to invest a lot of effort into creating such a thing. And we know that this will, you know, building it will, and creating good content, will kind of attract the right folks to the editorial outlet. So I'm sure there's plenty else that I'm leaving out, but those are the things that I do know. And I do know that some of it is just because we do value brand so much here, so it's kind of an investment we have permission to kind of make.

Charli: Yeah. I love that. I think that's a good approach to it because sometimes we can get a bit too bogged down in the numbers, and in doing things just for the numbers, and some things are more anecdotal, you know, things like, just people enjoying what you do and shouting it on a social media or something like that. So, yeah. That's good to hear about. You mentioned before that this was a project that took two quarters to work on. How much of your time during those two quarters was spent focused on this project versus other things?

Matt: This was our team's priority for those two quarters, of which was a total luxury and a total gift to us. It was also a fairly accelerated project to do in just two quarters. But we were given, you know, permission to focus mostly on this. If I had to guess a number it would be, you know, in the 80 to 90% range of our time was spent doing that. And other things, keeping the lights on tasks would happen in tandem, but we did want to make this a huge investment for our team. And we've kind of crafted a team around In the Works. You know, we've hired an editorial lead, who's hired writers, who's hired producers to create podcast and visual content. So we definitely focused a lot of our time on that. And we'll split it in quarters to come. Now that we've created this outlet that is a little, it is built on CMS. So it is more self-serve now than ever. Obviously, that took a lot of work and it took a lot of forethought to get it here, but ultimately it's going to be a lot more of a maintenance property and something that content and marketing can maintain themselves, which would be really, really cool.

Charli: Yeah. Let's talk a little bit about iteration, I guess, 'cause that's a big part of our jobs as in-house designers, you know, so perhaps more on the main Help Scout site, how do you iterate on that? Do you look at the conversion rate of the site and is someone coming up with ideas of like what to change to improve there? How does that sort of thing work?

Matt: Yeah. We're entering a really cool season where testing is becoming more prominent. Historically, we've done a lot. A lot of our work would be done on a page by page basis. So we'd focus on the entire page and the performance of an entire page. We're starting to get a little bit more granular where we're actually testing things on a much more micro-level. And we're actually just about to kind of work on a project where we start thinking about and testing from like strategy to design and development, on like sections, on components, on really individual things. So that way we can kind of dial things in a little bit more incrementally. 'Cause doing things on the full page level, A; you're not getting to isolation as well as you could. You can't really isolate which change is affecting the metric positively or negatively. And B; the turnaround time in the feedback loop is much slower. It takes longer to do that. So we think, and we're pretty energized that like taking a more micro view is going to help us be a little bit more iterative and a little bit quicker to knowing what's working.

Charli: I love that approach. And as you do this, as you ship test, is it, do you have someone on your team whose role it is to work on data and like feed that data back to you so that you get an idea of how your design is performing?

Matt: Yeah. We definitely have folks who kind of have their fingers on the pulse of how things are working. We have folks on growth marketing, in marketing operations, in SEO, who all kind of come together and sort of create this little cross-functional pod to, you know, propose tests and then kind of deliver that to design, to partner on how that test might come to life. And then we build that as well together. So it is so collaborative. We also like, solicit testing ideas pretty widely as well. I think a lot of it comes from that team, that pod that I described, but also, we solicit from the marketing organization or beyond, you can submit something in Slack with a certain command that'll actually migrate it to a board that'll kind of track, you know, kind of our backlog of testing ideas. So, it's really cool. And it's something we're eager to dig into. And I think it's going to be a big part of this next season artwork.

Charli: Yeah. And it sounds like it really aligns too with you wanting to improve the design system that you have in Figma, to make things more efficient if you're just focusing on components at a time, that makes a lot of sense.

Matt: Well, it's, I find that we create a lot more outliers and bespoke pages when that's the way those projects come in. Whereas when we start to think about things on a component basis, I'm compelled to think about how will this work here and elsewhere? And I think that reframe is gonna really help us gain efficiency down the line because when the page comes in, you have like, that feels like the deliverables. You might create a weird variant here because that's what served this or that. It's useful I think to start to think about like, how can this be flexible and how can this serve other pages? And how can we use this down the line? When you know changes are innate and will have to happen, it's actually easier to account for them. Whereas I think earlier the other approach, I think, takes a static batch of content and makes it look good. When you know that there's going to be flexibility, there's going to be testing and changes, you bake that into the idea, it becomes a more useful component.

Charli: I love that. That is really good, like advice and like a reason to think about things that way for sure. Let's end now by talking about what you're most proud of. It could be a project. It could be a certain impact you've had at Help Scout. It could be In the Works that we've just been talking about, but let us know what you're most proud of in your time at Help Scout.

Matt: Yeah. In the Works is certainly up there. I feel like it's at the intersection of all of our team's strengths. We didn't talk as much about visual and editorial art for In the Works, but that was another component where I saw our team kind of rally and find ways to create volume posts, solicit art from like editorial illustrators externally and art direct those people, and create kind of a new shifted kind of tone of what our editorial illustration looks like. That, plus what we got to do with dev and design, and kind of up our processes there, was huge, and I feel like it made that project really stand out for me. But otherwise I think back to some of the things that we've done, some of just like the cultural pages that we've done, the about page, the careers page, those are kind of a companion piece. Those were really enjoyable to do. And I really got a kick out of doing our DEI dashboard, which was another cool interactive project at Help Scout and a cool way to show, you know, how much this brand cares about diversity and inclusion. We're willing to be transparent when we know we have a ton of room to grow in that area, but we're gonna share that data, show how we've been tracking and kind of document like where we'd like to go, because we just know that diverse teams perform better and having more perspectives in the room just gives us a better chance of solving ideas, and making sure that we're solving ideas that work for all people of different backgrounds. So it's really, really cool. So I really love that project. And that was another one that I think our team got to dig in and try some moonshots that really kind of made a better end result. It was cool.

Charli: I love that. Well, thanks for all the detail and all of the, in the weeds that you shared with us, Matt, this has been fascinating for me and I'm sure for our audience as well. And I definitely feel inspired to go and try some moonshots now. So thanks for everything that you shared.

Matt: Thank you. I appreciate it for sure.

Charli: Wow. So I know we got really into the weeds in some parts of this episode, but I hope you enjoyed hearing those details from Matt as much as I did. I honestly often end up making changes to my process or trying new things, or at least just like seeing something in a different light as a result of these interviews. And I hope I'm not the only one. So I would love to hear about your takeaways. Please feel free to leave a comment on the YouTube video or tag me on social media with your thoughts. I am @charliprangley on both Twitter and Instagram. Something that really stuck out to me in hearing Matt talk about In the Works and all of the resources, and the thoughtful consideration that went into that project is that, when we allow time to explore and to try different paths as part of the design process, really great things can happen. And I hope that getting insights into Help Scout's process and like the team that was involved with that can give you some ammo to push for the time you need on your next project to make something truly wonderful, because it is worth taking the time for that. If you enjoyed this episode, please, firstly, share it with your design friends. I'd very much appreciate that. And secondly, head on over to Apple Podcasts and leave us a rating and review, really helps us get the show out there. Thanks again to Webflow for sponsoring this season and supporting the show. You can try out Webflow's site builder for free at insidemarketingdesign.co/webflow. And as an example of a site built in Webflow, you could head to the Inside Marketing Design site where you can find all the other episodes of this show as well as links to Help Scout and to Matt as well. Thanks for listening, everyone. And I will see you next time.

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