Behind the Scenes on the Do the Woo Site Rebuild

Robbie:
Hello, and welcome to another episode of Do the Woo. I’m Robbie Adair, one of the co-hosts here with Do the Woo, and I’ve got a really cool episode today that we’re going to be sharing with you. I will be co-hosting with BobWP himself. Hey Bob, how are you doing?

BobWP:
I’m doing good. I think people are maybe getting a little tired of hearing my voice. I seem to have been in more episodes lately, so I’m glad to have you here and bring in your lovely voice to kind of balance it out.

Robbie:
Well, thank you, but I don’t have quite the radio voice that you do, so I don’t think people will complain about hearing your voice again, Bob. So, today on this episode, this is a really cool episode, I feel like, because we’re going to talk about the makeover that Do the Woo went through—the website. We’ll talk to Bob here in just a second about how he actually got this kicked off, but the rebuild of the website was done by the Automattic Special Projects team. And so, we have Derek and Katie here from that team. I’ll start with Derek. Derek, hey, tell us how things are going and how long have you been with the Special Projects team?

Derek:
Thanks a lot, Robbie. Yeah, so my name’s Derek. I’ve been with the Special Projects team as a Technical Account Manager for a little over three years now.

Katie:
Awesome. That’s a long time. Hi, thank you for having me here today. I also joined the Special Projects team a little over three years ago. I joined about a month after Derek.

Robbie:
And now, the Special Projects team is really large when I look at the website. If everyone wants to check out the website, it’s specialprojects.automattic.com. So, you guys are a really big team. How many people are on the team now, approximately?

Derek:
It’s right around 30-ish people, I think. Is that right, Katie?

Katie:
I think so. Somewhere around there, yeah. 30.

Robbie:
Cool. And I know that you can’t give away all the secrets of how all Special Projects begin, but we know the story of this special project. So, Bob, tell us what kind of spurred this on. When did you find out you’d be working with the Special Projects team?

BobWP:
Yeah, well, the context behind it is, for about eight months, I had this vision that kept growing. I looked at my existing site, which I’d had for a couple of years. I had it redone, and it was really great for what I was doing when I had it done. But then, as the site grew and I started getting all these ideas—ideas that I did not know how to implement—I first thought, “I want to move to WordPress.com. That should be the home of Do the Woo, and it would be perfect.”

But how was I going to do that? That didn’t seem as simple as it might sound. Then I started thinking about how I’d like to simplify it—not have a page builder on it anymore and go to blocks. The more I thought, the more freaked out I got. Eventually, I decided just to direct message Matt Mullenweg on Slack.

I’ve talked to him before and asked him to be on a podcast show, and he always responds. So, I explained my vision to him. I wasn’t asking for anything, just sharing that I was putting together resources to make it happen. I just wanted to keep him in the loop of my ideas and see if he had any thoughts.

A couple of weeks went by, and then he sent me this simple message: “I got you a team. What’s the best email?” And that was it. Suddenly, I entered Derek’s and Katie’s lives. I’m not sure if they lived to regret it or not!

Robbie:
Well, just a quick question on that. What made you decide or envision going to WordPress.com versus, say, Pressable or any other major WordPress host?

BobWP:
Yeah, I’ve been with a few different hosts before. That was mostly when I was doing things myself, but I was getting to the point where I just wanted things to be simple. I didn’t care about testing plugins, seeing what worked, or doing this and that. I wasn’t interested in dabbling anymore if I didn’t have to.

I’d always had a WordPress.com account to play around in, and it always seemed so much easier as I became less of a power user. I just wanted to be like everyone else—creating content and letting the site run itself.

And this was more personal than anything. I felt that Do the Woo’s home should be on WordPress.com. It just felt right. If I have a podcast that’s dedicated to WooCommerce and WordPress, it should really live on WordPress.com. I knew enough about it to feel confident in that choice.

Robbie:
Awesome. Well, Derek, we’re going to start with you. When did you find out you’d be working on this project, and were you like, “Oh my gosh, there’s not enough coffee in the world for this?”

Derek:
I was really excited, actually. I enjoy being a part of the WordPress community and connecting with other WordPress creators. It’s a chance to feel more in the know about things that are going on.

The chance to work with Do the Woo and Bob was really appealing. As a TAM, or Technical Account Manager, we don’t necessarily get to self-select the projects we work on, but we can raise our hand if something interests us. I saw this one as an opportunity.

I enjoy the Gutenberg and block-building era. Anytime there’s a chance to reimagine a site and rebuild it with blocks, I want to be a part of that. Do the Woo was previously on Beaver Builder. My background in communications and content management also aligned with Bob’s vision for expanding to multiple shows. That made it a great match.

Robbie:
Cool. So, what’s your process for kicking off these projects? I’m assuming you do have a kickoff meeting with Bob to find out his vision for the changes he wanted, correct?

Derek:
Yeah, we have a project life cycle. That’s one way to put it. We start with a kickoff call, where we ask a bunch of discovery questions to capture the client’s goals. This includes thoughts on their audience, design preferences, and aesthetic. It’s a lot like how an agency operates.

We went through that process with Bob, asking all those questions. Then, we delivered a project brief where we outlined everything we’d discussed. It included a detailed timeline, functionality, and features.

Once Bob approved the project brief, we moved into the design phase. After that, it was design, development, and launch. Not to oversimplify, but the key was kicking it off with those discovery questions to fully understand Bob’s goals for the site.

Robbie:
So now, Bob, you yourself built websites back in the day, right? Was it interesting being on the opposite side of the table—being the client this time?

BobWP:
One thing is, it’s also interesting to be able to come up with an idea and say, “Hey, is this possible?” without the restrictions of my own skills holding me back. Before, I’d just tell myself, “No, it’s not possible because I have no idea how to do it.”

Through the process, everything impressed me. I just kept getting more and more excited. I thought, what better life than to have somebody handling all this and not having to worry about it? And I learned some things along the way.

It was absolutely amazing. The further we got into it, I’d share something with Derek, and he’d take it to the team. They’d do their thing, and he’d come back with something that was spot on. It was a very fluid partnership.

Robbie:
Cool. Awesome. Well, I want to dig in on the blocks, Derek, especially since you said you are a fan of Gutenberg blocks. We’ll come back to that. But before that—Katie, tell us, when did you come on board with the project, and what were you brought in to do?

Katie:
I came on about halfway through the project. We were in the development stage when I joined. Typically, we pair up on projects at some point, especially as they get to the more complicated stages of development.

Having multiple project managers on a project allows us to be flexible. If one of us goes out of town or gets pulled into something urgent, the other can step in. This ensures a seamless experience for our partners and keeps projects moving forward.

In this case, I came in to assist Derek, doing QA work and tracking the development progress. I flagged issues in GitHub and helped keep things moving behind the scenes, while Derek continued to lead the project.

Robbie:
Cool. And so how long was the project lifecycle on this particular one, Derek?

Derek:
Oh wow, that’s a great question. Do you remember when we started, Bob?

BobWP:
I believe we started in September of last year. Yeah, last year. I think that was the time we were just going through the basics at the beginning.

Katie:
The kickoff call was on July 5th.

BobWP:
Oh, July 5th! See, I don’t even know what I’m talking about. I think we had the call then, and maybe the project started moving a bit later and got on the schedule in September—or maybe I’m just totally delirious now.

Derek:
That sounds about right. The better part of a year, probably. Especially when you’re migrating from something like a page builder.

One challenge we spent a lot of time cleaning up—and Bob can attest to this—was dealing with weird encoding errors. You had characters replacing apostrophes, commas, quotes, and things like that. The HTML cleanup was particularly challenging for this site.

Most of the other aspects went fairly smoothly, as far as development projects go. Of course, there are always hiccups. But the encoding issue was a sticky point, especially as we got closer to launching.

BobWP:
Yeah, we even did a soft launch where the site went live, but I wasn’t actively promoting it as the new version of Do the Woo.

Robbie:
So, when you’re working with an existing site like this, one that’s getting regular updates—because goodness knows there’s a podcast almost every day—did you write migration scripts to handle the data migration, or was it more of a manual process in this instance?

Derek:
For the more complex migrations, we leaned on our developers to write automated scripts. For example, we did delta migrations right before the launch.

There was a subset of content that needed to be migrated manually to match what was coming over, but we also implemented a content freeze. We told Bob, “This is the date you need to stop publishing podcasts because we’re going to migrate everything, finalize it, and then launch.”

Robbie:
Now, Bob, I know you had a lot of content on the old site. Were you also heavy on users, or was that something new with the rebuilt website?

BobWP:
Yeah, we already had a lot of hosts in place, and they did some amazing work connecting user roles and building profiles.

The profiles for the hosts were particularly great—they connected all the dots. And then, of course, the podcast part of it was another layer of complexity. I think we had a couple of small hiccups and ended up working with Castos since we kept the podcast hosting there. Their team was super helpful in ironing out any issues.

Robbie:
So are you still using Castos in this setup for the new site?

BobWP:
Yes, I’m still using it. Initially, there was talk of hosting the podcast feeds on WordPress.com, but I think it only supported a single feed. Since we had multiple feeds, it sounded like it would be a nightmare.

Derek:
Yeah, WordPress.com has podcasting built in with the core WordPress audio block and RSS feeds, but Bob’s network of podcasts made it clear we needed to stick with Castos.

Sometimes, for projects like this, we scope out a phase two or three to revisit things like migrating episodes to a different host. But for now, Castos works really well, and Bob is happy with it, so there wasn’t a need to change.

Robbie:
Exactly. Castos has a great reputation as one of the top podcast hosting services, so it makes sense.

Katie:
Their support was fantastic, too. As we encountered questions or issues, Bob connected us with their team, and they were really helpful throughout the project.

Robbie:
Fantastic. Now, Derek, you mentioned that WordPress.com supports podcasting out of the box for simpler setups. So, if someone has a smaller podcast, they could actually host it directly on WordPress.com as part of their hosting, right?

Derek:
That’s correct. The Automattic theme team has even released a couple of podcast-style themes that are optimized for this. So, if someone wants to host a podcast and have a website for it, they can do it all through WordPress.com.

Robbie:
Cool! That’s interesting. I might spin up a little test site to try that out.

BobWP:
One of the things I wanted them to touch on is the taxonomies they created. Several were built specifically for hosts, shows, and even for the blog. We did a custom post type for that, and I thought it’d be great to have Derek explain more about it.

Derek:
That does seem backwards a little bit, but yeah, one thing Bob wanted to leverage with WordPress.com was the Jetpack newsletters feature. To use that, you have to work with the default WordPress post type—it doesn’t work with custom post types.

Since podcasts were Bob’s primary content and something he’d be publishing consistently, having users subscribe and get those episodes in their inboxes was a big bonus of moving to WordPress.com.

BobWP:
And then I came along and said, “Oh, I want to add the blog back in.”

Derek:
Right! So, bringing the blog back as a custom post type might seem counterintuitive. But it made sense in Bob’s case.

We wanted to make the podcast side of things more dynamic and interactive. For example, when you visit Do the Woo now and land on an episode, you can see the hosts and guests. You can even click through to view their profiles. This lets users see the network effect of Do the Woo—who’s been on which episodes, who’s hosting what shows, and so on.

Structuring the content this way made it cleaner and more engaging. The blog was moved into its own custom post type to keep things organized.

Robbie:
What was the reason for creating a custom taxonomy for the blog instead of just using categories?

Derek:
The custom taxonomy allowed us to make the podcast content more engaging. For example, we tied each host and guest to episodes dynamically through their profiles. This interaction wouldn’t have been as seamless with just categories.

Keeping the blog separate as a custom post type also helped maintain clarity. WordPress is great for content management, and breaking things into distinct buckets makes it easier to manage over time. It’s the opposite of what most people do, but for Bob’s publishing needs, it made sense.

Robbie:
So you used a block theme for this site, correct? Did you modify an existing block theme, or did you create one from scratch?

Derek:
We used one of the podcast-styled themes from the Automattic Themes team as our foundation. From there, we customized it to fit Do the Woo’s branding, including the colors and custom fonts.

The design at launch has already evolved. Bob has been messaging us recently with ideas for reimagining the homepage, and thanks to blocks and full-site editing, we can easily accommodate those changes.

For example, if you go to the Do the Woo homepage now, you’ll see collections of shows with recent episodes. It’s completely different from how it looked at launch. Full-site editing has made it easy to make these updates and keep iterating.

BobWP:
I kept thinking, when people land on the homepage, they don’t realize how much content is being pushed out. I shared a couple of ideas, and again, magic happened! It came back exactly as I envisioned it.

One thing I’ve loved about working with the team is that I’ve learned a lot. Sometimes I poke around and make small changes. My very first attempt, I thought, “Oh, I’ll just change a permalink,” and I ended up breaking everything. So now, I’m more cautious. For smaller tweaks, I’ll send in a support ticket.

The team is great about sending back videos explaining what they did. They also show me how to make changes myself in the future, which is really helpful.

Robbie:
That’s great. Bob, you’re bound to break something here and there—it’s the mark of a true website owner!

Katie, were you involved in implementing the map feature on the supporters’ page?

Katie:
Yes, I was. We created taxonomies for sponsors, hosts, and guests. These taxonomies are tied to role types and locations, which are displayed on the map.

Derek:
Katie explained it well. Essentially, the profiles for each taxonomy—hosts, guests, and sponsors—have fields for name, social links, and location. These locations are tied into the map using an open-source mapping tool, likely Leaflet.

The map is another way to enhance the dynamic experience of the site. For example, users can see hosts and guests globally and click through to their profiles. It adds another layer of exploration to the Do the Woo community.

Robbie:
So this is a block theme, and I assume you used full-site editing (FSE) for the project, right? Did you run into any challenges with FSE, or did you have to do anything custom to work around limitations?

Derek:
With Bob’s site, there wasn’t much custom functionality required for the header or footer since the design was simple and clean. One challenge we occasionally run into—on other projects, too—is creating a mega menu or a specific mobile menu design. That sometimes requires custom work in the theme JSON files.

But overall, the FSE experience was smooth. It allowed Katie and me to make a lot of adjustments ourselves without needing to involve developers. For example, if Bob wanted changes to an episode page or a sponsor layout, we could handle it directly in the block editor.

I’m a huge advocate for full-site editing. It unlocks so many editing possibilities for us and our clients.

Robbie:
That’s great to hear. Katie, you mentioned earlier that you came on board to assist with managing multiple projects. How many projects do you typically work on at a time?

Katie:
On average, we handle somewhere around 12 to 15 projects at a time.

Robbie:
Wow. That’s a lot to keep track of.

Katie:
It is, but the pace varies. Some of our partners are single-person operations, so they may go quiet for weeks at a time. While we have a timeline in mind, we often adjust to accommodate their schedules.

This means that while we might be managing 15 projects, only two or three may be in particularly busy phases at any given moment. Others will be quieter. It’s manageable because the workload ebbs and flows.

BobWP:
Katie, is there a specific type of project you look for or get excited about?

Katie:
A number of our projects come to us the way yours did—through a connection with Matt. He often sends us projects with unique challenges to solve, or sites that have great potential and just need some improvements to really shine.

Other projects come from existing partners—people we’ve worked with before who return to us with new ideas or ventures.

What’s fun for us is that we get to try out the latest features in WordPress and Automattic products. We “dog food” them, meaning we use them ourselves to test usability, find bugs, and identify areas for improvement. We then surface these issues to other teams at Automattic, which helps improve the tools and products for everyone.

BobWP:
Speaking of the newest things, I had an interesting experience earlier this year. At CloudFest, I met Matthias Pfefferle, the creator of the ActivityPub plugin for the Fediverse. We happened to meet at breakfast, and we started talking. I told him about the work we’d been doing on the site, and that’s when I made the announcement about the site’s relaunch.

Matthias suggested we “Fediverse-up” the site, and I thought, “Why not?” I understood the basic concepts of it but not the finer details. Matthias came on board and helped set it up. I think both Derek and I learned a lot during that process, though Derek may have learned even more than I did.

What were your thoughts on that whole experience, Derek?

Derek:
It was definitely a learning experience! Initially, I was focused on making sure the site achieved Bob’s goals. When Matthias introduced the idea of integrating with the Fediverse, it opened up new possibilities for enhancing the site’s interactivity.

One feature we added was the ActivityPub plugin’s ability to connect author profiles to their Mastodon accounts. For example, if a visitor is on Bob’s author page, the “Follow” block inherits Bob’s Mastodon handle. The same happens for other authors.

Another enhancement was how ActivityPub connects conversations. When a podcast episode is published, it’s shared on Mastodon. If someone comments on that Mastodon post, those comments feed back into the WordPress comment thread for that episode. It’s amazing to see how conversations on Mastodon are no longer siloed—they’re collected back on the site.

When I first saw it in action, it blew my mind. It’s such a powerful way to connect different platforms.

Robbie:
That’s really cool. Okay, I have one last question for Derek or Katie, and then I’ll wrap up with Bob.

For the design process, does your team use Figma? And do you design mobile-first or desktop-first?

Katie:
Yes, we use Figma. We start with desktop designs because they are more complex, but we develop mobile-specific designs as well before moving into development.

Robbie:
I love that! My agency has been designing desktop-first for over 20 years, even though many agencies have shifted to mobile-first. I always felt desktop design allows for more complexity and creativity, especially for sites like Bob’s, which probably has a high percentage of mobile visitors but still benefits from a desktop-first approach.

Katie:
Exactly. Starting with desktop ensures that we can define the full hierarchy and structure of blocks and sections. Once we have that established, we translate it to mobile.

Robbie:
Do you address media queries throughout the project, or do you wait until the end to handle them?

Katie:
That’s more of a development task. During the design phase, we plan what blocks and elements will be used and leave handoff notes for developers. For example, we might note, “This is a query loop block.” But the media queries are implemented during development.

Robbie:
Awesome. Now, Bob, after launching the new site, what differences have you noticed in your day-to-day workflow? Is it faster and easier to maintain the site and publish new podcasts?

BobWP:
Absolutely. The previous page builder worked well for the site and my workflow at the time, but I’ve fallen in love with full-site editing.

Creating content is so much easier now. I’ve streamlined my workflow and have the flexibility to make small tweaks as needed. If I need to create a new page, sometimes I’ll just duplicate an existing one and adjust it.

Another big difference is that I don’t worry as much anymore. I can focus on content and rely on the team for support if something needs fixing. The best part is being able to ask, “Is this possible?” and actually have it happen.

Working with Derek has been especially great. He’s been more than a technical resource—he’s also a sounding board for ideas. Whether it’s about the site or something else, he gives me thoughtful feedback that helps me move forward. It’s been an amazing experience overall.

Robbie:
The new site looks amazing. You and the Automattic Special Projects team did a fantastic job. I don’t even need to check the Wayback Machine—I remember the old site, and this one is a huge improvement.

BobWP:
Thank you! We’ve got more tweaks planned for the homepage, and in January, I’m launching version 4.2 of the site. It’ll coincide with our seventh anniversary, so I’m planning some fun updates.

Robbie:
That’s exciting! Derek and Katie, will we see you at any events next year?

Katie:
I won’t be attending any events personally, but other members of our team will be.

Derek:
We presented at Showcase Day at WordCamp US this past year, and I’m hoping to attend next year’s WordCamp US as well. There’s also a new event called PressConf that I’d love to attend, though I don’t think I’ll make it this year.

Robbie:
I always encourage going beyond WordPress-specific events to broader tech or business conferences. It’s a great way to spread the WordPress and WooCommerce message.

BobWP:
Absolutely. I just want to thank Derek and Katie again. This experience has been incredible, and I’m looking forward to continuing our collaboration.

Robbie:
Derek and Katie, thank you so much for sharing your insights. If listeners want to connect with you, how can they reach you?

Derek:
I have a personal website, derekhanson.blog, and I’m also on LinkedIn.

Katie:
Same here—LinkedIn is the best place to reach me. My profile is katie.mckenna.

Robbie:
Perfect. And for everyone listening, check out the new Do the Woo website. Poke around and try to break it (just kidding, but seriously, test it out). And don’t forget to tune in for the next episode of Do the Woo!