**Jesse Friedman:** Welcome to Impressive Hosting, a podcast about the role hosting plays in shaping the open web. I'm your host, Jesse Friedman. On this show, we go deeper than uptime and dashboards. We talk about hosting as infrastructure, about ownership, independence, and what it takes to build ethical, high-end WordPress hosting that actually serves creators, businesses, and the internet itself. Before we dive in, head to impressive.host. That's where you can comment on episodes, ask follow-up questions, and help shape future conversations. You'll also find links to follow, like, and subscribe wherever you listen. And we're back with Sanja Grbic, senior product designer at Automattic, and a friend who I've had the pleasure of working with for almost five years now. Someone who's been absolutely amazing in the work she does around product design. In the last episode, we covered a variety of things, from design systems and pattern libraries to the way hosting companies should think about incorporating innovation into their product design, while making sure customers and users feel comfortable and aren't disrupting the patterns they're used to. We left off getting ready to talk about the second project Sanja was working on over the last two months. It's actually a really cool product and I'm excited to talk about it. But before we dive into that, we wanted to pick up where we left off, which is around the way our organizations are changing, and the way product design roles and development roles are all shifting with AI. So Sanja, I'm gonna throw it back to you. Tell us a little bit about what you're seeing and how you see the world shifting around us with AI.
#### How AI is changing design and engineering roles
**Sanja Grbic:** Right. So as I mentioned in our previous chat, for a designer, being able to code seems to be the most applicable area for AI right now. It's expanding our toolbox. I think designers are all becoming design engineers. It's available to us. We've all evolved. When I say we, I mean designers who've worked in the field for ten years or more. I remember using Photoshop daily, then Sketch, then Figma, and all sorts of things. We adapt and adopt new tools, always. But I feel like AI now has a bigger impact on how we collaborate with each other, how the designer and engineer work together, how the designer, product manager, and engineer work together. It seems like our skills are getting balanced out, where everyone can be a little bit more of a product manager and an engineer, besides their main skill. The strongest skill I bring will always be design, simply because of my experience. My intuition is sharpened. I've seen why things fail and why things work. I will always bring that as my strongest contribution. But with AI, I can definitely do quick business goals research, look into data, create an implementation plan, and then also implement the front end, and maybe even more than that. So the first thing I've noticed is that designers are confidently moving into this design engineer role. On the other hand, I'm not an engineer, so I can't really speak for their experience. But my observation is that the engineers who have collaborative skills, who share their knowledge and include other people, they're the ones who are going to be most valuable. They kind of evolve into enablers in these teams, helping their fellow designer or product manager set up the environment, set up the sandboxes, and plug in to contribute to the code itself. And then in the organizational sense, companies, especially larger organizations, have to do more than just ask people to use AI and move faster. There are actual system changes that have to be in place, and we've seen that with RSM. Automattic has done a fantastic job. Our systems team, or operations team, has set up an infrastructure where I feel confident contributing to production. There are checks in place that enable me to do that. There's documentation that enables me to set up all of the environments, move through those steps confidently, and make it work, which is a big deal.
**Jesse Friedman:** Yeah.
**Sanja Grbic:** And then on top of that, everything else the company is doing around AI literacy, allowances, and AI enablement training.
**Jesse Friedman:** The AI enablement training is one for sure.
**Sanja Grbic:** AI enablement training is huge, right? And it's a huge investment in your own people to keep them in step with the times.
**Jesse Friedman:** Yeah.
**Sanja Grbic:** That's an expression now.
**Jesse Friedman:** It is now.
**Sanja Grbic:** Sure it is. We're innovating in English.
**Jesse Friedman:** I love it. Yeah. For people who are listening and don't know, Automattic has internally designated a few folks to provide training, documentation, and a whole bunch of other things related to AI to empower us to do more and move faster. Em Shreve is someone who works at Automattic out of New York. They work out of the NoHo office and run these training cohorts where Automattic employees are flying in from all over the world to spend two weeks on-site in New York going through this training. You actually went through it yourself last month, right?
**Sanja Grbic:** Yes, exactly. I spent two weeks in New York. Not just the training, but also the tools they develop to enable this and make the most out of all of the documentation we have as a distributed company, through the AI tools. But yeah, the AI enablement course was fantastic. Just sitting in the room, we were maybe around 30 or 40 people, listening to the lectures, discussing how we're all individually using AI, sharing tips, helping each other set things up. Em has done a fantastic job because that's such a difficult thing to teach, enabling people in doing something that changes every day. What we're talking about right now is relevant today, but with AI advances, maybe it won't be relevant in a week. If you're preparing an enablement course, you really have to be flexible, adaptive, and quick on your toes. To change, and also to help different kinds of folks in different roles. Really, kudos to Em and that team.
**Jesse Friedman:** Yeah, I think it's really great. And one of the things that seems to be coming from this is that we may actually be making it available to third parties as well. In the future, it may be something Automattic actually ships as a product. So if you're listening and you want AI training, definitely reach out and ask for it. It's one of those things where Automattic is going to have to make the decision about whether to keep it only available internally or make it available externally, maybe to our partners or others. The more people ask for it, the more they can help shift that idea. But yeah, I think one of the things that's really interesting is that you talked about how these processes in place make you feel more comfortable engineering. Hosting companies and agencies listening can benefit from knowing that Automattic has always had this long-standing tradition of developing in public. Even internally, when we're developing new projects, we all feel comfortable shipping things to GitHub, creating an environment where we allow other people to read and review our work. So even if we're using AI and empowering a product designer like yourself to start engineering, it's not necessarily going to impact millions of customers tomorrow. It's still going to go through transparent workflows. People are going to review the code, test it, and everything else. What's important is that the empowerment part means you've been given the tools and the processes to actually dive into these things, make mistakes even, but with guardrails in place to make sure you're not going too far off track.
**Sanja Grbic:** Yes. Yeah, yeah.
**Jesse Friedman:** Very cool. And you talked about design engineers. You know what's funny? About 16 years ago, the first person I hired at a company here in Rhode Island called Astonish, I was brought on to move a .NET-based CMS over to WordPress, bringing over thousands of sites. Once I had done that, the next step was to design some WordPress themes. That company was set up with designers and developers. The designers would use Photoshop to construct the designs and then hand them to a developer whose job was to slice, you know, break up all the assets. You remember this?
**Sanja Grbic:** Slicing.
**Jesse Friedman:** Yeah, yeah. My first hire was someone named Jeff Golinski, who you obviously know. Jeff has been on the show. He's someone I've known for a long time, and a great guy. He was the first person we hired who was what we considered multidisciplinary. He could design the designs and then actually code the HTML, the CSS. He even got into some JavaScript and things like that. At that time, everyone was really shaken by the idea of hiring a single person to design and develop the themes for WordPress. They did not like the disruption at all. I'm curious, how have you been seeing, both inside Automattic and outside of it, when you talk to your colleagues, friends, and people in this industry, how do designers who have been strict designers for years feel about getting into AI and using it to start vibe coding, developing, or engineering? Is it something people are widely adopting, or is there a bit of a rejection phase happening too?
#### How designers are adapting to AI
**Sanja Grbic:** I think all of the above is true. I've heard different things, and I think people have conflicting feelings about it. Definitely those designers who have always been creative and playful and exploring new things are vibe coding. It's almost like your working style. That's not necessarily better than someone who has a clear definition of what they do, sticks to it, and is good at it. The tools they use might evolve, but they're not expanding their role into other areas. I evolved from a graphic designer to a web designer to a UI designer, a visual designer, a UX and UI designer, and then a product designer. We call it whatever. Now I'm like, should I change my LinkedIn to product engineer? No, it's okay. I'm a product designer. I use all of these tools. I can adapt to whatever. But I still have friends who do UX and that's all they do. They don't even design the components. They just think about flows, or they're service designers. But I think everyone is using AI for something, even if it's just for research, gathering their thoughts, or creating a presentation. I think all of it is the right way of doing it. Each individual knows what they're good at, they know what they enjoy, and my recommendation would be to do what feels good and what makes you do your best work. You won't regret it. My process still changes every day.
#### Building the Woo merchant chat tool
**Sanja Grbic:** The second project I did together with Philippe, our lead on the Jetpack design team, we talked about what we wanted to build and we didn't start in Figma. For me, that was the first time doing that with a fellow designer, not starting with visuals. We started with a plan that was researched with Claude Code, or Claude, using some of our tools developed by Aman and the team, like the context tools where I can easily research what users need on Woo or elsewhere.
**Jesse Friedman:** Yeah, before you continue, I think that's really helpful to people at home. Automattic has always been a company that documents everything. We use something called P2 internally, and because of that, we've always been documenting everything. From projects to partner meetings, you can see who Matt's meeting with and how that meeting went. There's so much information. So now the really amazing thing is that we have AI tools that help us actually digest and metabolize that information in a way we've never been able to before. I just want to give a little context around what you're referring to in terms of Context A8C. It's our homegrown, AI-driven tool set that helps us do internal research on our own documentation and collaborative work.
**Sanja Grbic:** Yes, incredibly helpful.
**Jesse Friedman:** Immensely helpful for starting off a new project.
**Sanja Grbic:** Yeah. So that research was done fast. Of course, behind that, there are years of experience of knowing exactly what would be good for the users, having a sharp product instinct, and all of that. It just speeds things up. It can't really make up for those things. Then I put together a plan and shared it with Philippe. I was like, "What do you think of this?" That was on a Friday evening. On Monday morning I woke up and he had built the whole thing. We're in different time zones. I'm on Pacific Time in San Francisco and he's in Portugal. So when I wake up, it's the end of his Monday, and he was like, "I built it." And then we iterated on the live thing. We still used Figma for fine-tuning visuals, some abstract explorations, like figuring out the splash screen and things like that. We also iterated on the UX. But this was an iOS app and a chat widget on the site. We had such good results within only six days that I was really blown away by what we were able to achieve. AI enabled parts of it, but it wasn't AI that unlocked it. What unlocked it was the RSM, the context of the project, the agency we felt to just move forward with our ideas, and the fact that we are both designers with our process already established. So we were able to move really fast. We both knew what came next.
**Jesse Friedman:** Right. And so you were two designers who aren't engineers who set out to build something. I don't think we've actually described it yet, but the second project was an app that allowed Woo merchants to communicate directly with their end customers to answer questions in a chat-based user interface. That allows the merchant to answer questions in real time and do a variety of other things. That connection between the merchant and the user is the problem you focused on. And you were able to solve it rather quickly.
**Sanja Grbic:** Yes, rather quickly. The customer would be able to land on the site and ask any questions they have quickly. And for the merchant, the experience is contained inside this inbox or message management app. So it's not like, oh, I'm managing my site with so many features. No, this was just one thing you can use on the go. But that wasn't all. You could enable the setting to have AI answer those questions, script the site, look for answers, and for everything that's a straightforward answer, the AI would actually respond rather quickly. But the merchant could jump in at any time or follow up with the customer. It's a really useful set of features. This is not released to our customers yet, but we're working on that.
**Jesse Friedman:** Yeah.
**Sanja Grbic:** It's a proof of concept right now.
**Jesse Friedman:** It's really remarkable that you were able to build that so quickly. I think that leads me to two conversation paths I want to explore. One is that in the first episode, we talked about how with WP Cloud, our hosting partners can leverage different technology to move to fast deployment and start using WP Cloud rather quickly. We always end up having a conversation with them about how they can focus on other aspects and innovate in different areas. What's really remarkable here is that you set out to solve a customer problem and did it rather quickly, specifically around Woo. One thing I want people at home to think about is this: with these tools and the fact that we're empowering people to build more things, it does not have to be your product for you to make improvements on it. So if there's a hosting company listening and they're thinking about a poor experience around WooCommerce, or something they want to unlock, they don't have to make that request to Automattic to build that thing. Because it's open source technology, because it's WordPress plugins, there's so much you can do to empower yourselves to unlock the development of these projects.
**Sanja Grbic:** Because of the open source nature of it.
**Jesse Friedman:** Yes, exactly. So if you're at home thinking, "I wish there was an SMS to merchant tool that didn't cost so much or worked a certain way," now we're at a point where you can just build it. I think the blocker there is that people are thinking to themselves, "Well, we're a hosting company. We don't own and operate WooCommerce. Maybe it'll feel like we're competing with Woo if we build it, or maybe it feels like we're diverging." No, just go build it. Go make the user experience better. Do it out in the open. Do it open source, and that way everybody can benefit. People have the opportunity to take advantage of these things, not just from a user perspective, but from a development perspective. It makes the overall ecosystem better, which lifts all ships. We don't always have to be thinking about competing.
**Sanja Grbic:** Absolutely agree.
#### Rethinking support through async, mobile-first communication
**Jesse Friedman:** And then the other thing that's interesting for hosting companies is that you're touching on something where I think we're going to see a major shift. We've talked on this podcast a lot about support. Support is like a hairy lollipop. It's something you have to provide, but it's always done a certain way through Zendesk or some other tool set, and you're kind of limited to those things. Do you provide phone support? Email support? We have hosting partners at WP Cloud who provide Slack support. There are all these different ways of approaching it. But one thing that really unlocks all of this, and we talked about this in the first episode too, is being where that user is present. So if you're in the panel and there's a chat window, that obviously makes sense. But we're not always considering that the user is now tied to their desk. The minute you start a chat window in that panel UI, there's a level of confidence you don't have that you'll get the answer from the AI bot, so you tend to ask for a human right out of the gate.
**Sanja Grbic:** Mm-hmm.
**Jesse Friedman:** Then you're stuck waiting. One of the things that drives me the most nuts, which I tell every single support staffer I ever interact with, is that I might end up waiting 30 or 40 minutes for them to respond to me. But once they respond, they give me like a 60-second window to respond again before they close the chat window. It's all focused around the speed at which they can resolve a ticket. I think it would be really interesting to explore a different way of thinking about it. Not necessarily how fast you can resolve a ticket, but how well you can provide a good experience, how great the conversation can be. There's a product out there called Bespoke Post. It's a monthly shipping thing with camping tools, hunting things, cooking stuff. I signed up and I've been a customer for five-plus years where they just ship me something every month. But the thing I really love about Bespoke Post is that they just have a phone number for support, and I can put it in my phone as a text message. Any time I need support, I just start talking as if I'm chatting with a friend. And it's not about speed at all. They actually respond rather quickly, but I don't care how long it takes because...
**Sanja Grbic:** Because you're not staring at your phone waiting for it, afraid to break the connection, right?
**Jesse Friedman:** Right, that's exactly it. Because they've changed the dynamic so effectively, I'm no longer thinking, "Oh, now I'm tied to my desk," or "I don't want to start this chat because I have to be somewhere in 20 minutes and I know it won't be over by then." Like yesterday, for whatever reason, the email didn't send to me to approve my box for this month, so I just sent them a quick SMS. I said, "I don't want the thing coming to me this month. Can you reverse the charge?" I did not care to look at my phone again. I didn't open a chat window. I just sent them a quick text message, and then about an hour later the charge was reversed. They gave me a 10% off coupon and sent me an SMS saying, "We're sorry for the inconvenience." It was just such a great experience. I think that's something really lacking in the hosting industry. You have customers who are trying to do really hard, complex things, trying to build something they don't have a lot of experience building. If we can provide support in a way they can digest and actually leverage, in a way that makes them happy, that's going to be hugely advantageous. It also changes the dynamic because then it's not about resolving an email ticket as fast as possible. It's not this back and forth that requires going to your inbox, answering a question, and waiting again. It's just there. You can choose to respond whenever you want. That's the piece that I think is missing from all of this. And what's really interesting about the tool you built is that you create an environment where it's safe to just ask questions. You've removed this speed element that makes it a lot easier for everybody to feel comfortable having a nice conversation rather than a transactional one.
**Sanja Grbic:** Exactly. Yeah. We envision it as a welcoming tool for new leads or new customers who land on the site. They have the opportunity to engage quickly with whatever is on their mind. The merchant can reply immediately if they're available, or follow up over email, or the AI can provide a pretty good answer if the information is somewhere on the site. Yeah, we were just thinking about the experience, and as you say, the experience can always be improved even without new technology. As you can see, even text is better than just sitting and waiting.
**Jesse Friedman:** Yeah, you don't have to reinvent the wheel.
**Sanja Grbic:** Yeah.
#### AI Engineers World's Fair and upcoming talks
**Jesse Friedman:** So right before we wrap up our second episode here, you're in San Francisco now and you're going to be there for an event. The AI Engineers World's Fair, right?
**Sanja Grbic:** Fair, yes.
**Jesse Friedman:** In a couple of weeks. And I'm going to be there too. I'm going to be presenting the Radical Speed Month project I worked on called Arc, which is a real-time sales engine that brings human-made content to the forefront of a landing page and designs a landing page for you in real time using human-made content. When Derek Smart and I set out to build a real-time sales landing page engine, one of the things we really wanted to focus on was this idea that AI should be enabling humans rather than replacing them. That's a philosophy we have internally at Automattic as well. One of the core concepts of this tool became: how do we give back to the salespeople, the content creators, the people building the website? How do we let them focus on what they do best and let the AI handle the work of organizing that information? What we ended up developing was a tool that lets you use WordPress to go into the WP admin to design all the landing pages, blog posts, and evergreen content you want to create. Anytime you create a pattern you like, you just designate it as something the AI can reuse. So when you arrive in this AI window, instead of a little tiny chatbot, it's asking you questions and designing the landing page based on human-made content. But it's really more about lifting up the work made by humans rather than trying to be creative on its own. That's what we're actually going to be presenting. Through the lens of this product, we're presenting this idea that AI should really be helping you as an individual do what you do best, lifting up your talents and skills, and also handling the productivity work by taking away the repetitive stuff. But you proposed a talk as well. I don't know if it's going to happen or not, but if you do get the opportunity to give that talk, what can people expect to hear from you?
**Sanja Grbic:** It will definitely at least be in the online track, so in the next few days it will appear online. And then, if everything works out, I'll hopefully also have the opportunity to present in person. But I will definitely be at the event. I'm super excited about hearing your talk because I think your project was mind-blowing. I'm going to talk a little bit more about the two RSM projects I did, plus a shorter one I did during the AI enablement training. I'm going to tie in this whole story and talk in depth about my different experiences working in different team setups for each of those projects. One was a group of three, one was a group of four mixed with developers on the team, and the third one was two designers. I'll talk about how we're all adapting and what skills are coming to the forefront, now that everyone can do a little bit of product, a little bit of design, and a little bit of engineering. I'm going to share my thoughts on how all of our roles are going to evolve.
**Jesse Friedman:** Very cool. I really look forward to that.
**Sanja Grbic:** Yeah, and how large organizations can have their teams work faster and get to results faster by doing that.
**Jesse Friedman:** That's awesome. So if you can't make it to the event, at the very least your talk will be online. Maybe what we'll do is share it in the show notes, or if it comes out afterwards, we can leave it as a comment on the post when we publish this episode. So keep an eye out for that on impressive.host. And Sanja, thank you so much for joining. It's great to see you. I'm jealous of the view behind you right now. It looks amazing. I'll see you in a couple of weeks and I look forward to that too.
**Sanja Grbic:** Me too. I'll see you very soon. Thank you so much for having me, Jesse. This was a wonderful conversation, as always.
**Jesse Friedman:** Awesome. Thanks. All right, see ya.
**Sanja Grbic:** See you.
**Jesse Friedman:** Thanks for joining us on another episode of Impressive Hosting, where we uncover the core tenets of great WordPress hosting. Do you have a follow-up question for today's guest? A thought or comment on anything we talked about? A future guest suggestion? A hosting horror story? What do you think makes great WordPress hosting? All your comments shape the show. Drop them on impressive.host. We also appreciate you following us on social media and subscribing to the podcast on your favorite platform. Finally, do check out our list of open source projects that need support at impressive.host. Whether it's code, community, or cash, you can make a difference. See you next time.
