Season 2 · Episode 3
CloudFest 2026 Goes Business: Why WordPress Agencies Should Pay Attention
In this episode of Within WordPress, we sit down with Carole (CloudFest) and Mark Weisbord (CEO of Greyd) to explain what is changing at CloudFest this year, and why it matters for agencies and WordPress businesses. The headline is the launch of the WordPress Business and Agency Summit on the Monday before the main CloudFest event. We position it as a connector between the CloudFest Hackathon and the main CloudFest conference, and as a deliberate step toward giving agencies and WordPress businesses a more relevant, more pragmatic, more commercially useful program than the traditional “WordPress Day” format. We unpack the difference between WordCamps and CloudFest. WordCamps remain community-first, volunteer-driven, and primarily focused on education and connection inside the WordPress community. CloudFest is a for-profit, cloud and hosting industry conference with a very different scale, structure, and mission, and it can build a dedicated business-focused layer around WordPress without trying to turn WordCamps into something they were never designed to be. This year’s Summit expands the former WP Day into a full-day, two-track program, adds an exhibition area, and targets roughly 800 attendees in a more intimate setting inside a much larger 10,000+ person event. From Mark’s perspective, if we want growth and new partnerships, we need to attract agencies outside the WordPress community, and we need content that connects to direct business impact. That means talks about sales, pricing, go-to-market, agency operations, maintenance revenue, and what it really takes to move from agency work into becoming a product company. We also talk about the CloudFest Hackathon as a uniquely valuable environment for multi-day collaboration and deeper conversations that rarely happen at faster-paced conferences. Carole connects that to a broader goal: cross-CMS collaboration and strengthening the open web, so we do not end up with a future where a handful of platforms dictate where and how people can publish. We close with practical attendance advice, a reality check that the Hackathon is already fully booked, and the key dates for the Summit and the main CloudFest event. 00:00 – Cold open: editing workflow and “wave” marker for cuts00:01 – Welcome and setup: two guests, and why this episode is different00:02 – Carole: WordPress community background and CloudFest involvement00:03 – What CloudFest is: scale, audience, and Europa-Park as the venue00:04 – “Everything is different this year”: why we are doing this episode00:05 – The new WordPress Business and Agency Summit: where it fits in the week00:06 – Mark Weisbord (Greyd): the missing business layer in WordPress events00:07 – From “WP Day” to a bigger Summit: what changes operationally00:08 – Two tracks, full day, and a dedicated exhibition area00:09 – Why this format matters: connecting agencies, partners, and real-world solutions00:11 – WordCamps vs CloudFest: why they serve different purposes00:12 – Sponsor reality: ROI pressure, leads, and reaching agencies outside the bubble00:13 – Content shift: business impact over general tech presentations00:14 – WordCamps still matter, but they are not the vehicle for everything00:16 – Biggest change: bring in agencies outside WordPress, plus an entertainment factor00:18 – CloudFest vibe: opening party, Lords of the Uptime, and the venue experience00:23 – Practical advice: stay multiple nights for Summit welcome + opening party00:25 – Hackathon value: multi-day conversations and real collaboration time00:28 – Hackathon evolution: cross-CMS collaboration and protecting the open web00:33 – Why agencies benefit: broader ecosystem exposure than a WordCamp context00:36 – What the Summit covers: sales, pricing, playbooks, productizing, maintenance00:40 – How Summit pillars extend into t...
About this episode
In this episode of Within WordPress, we sit down with Carole (CloudFest) and Mark Weisbord (CEO of Greyd) to explain what is changing at CloudFest this year, and why it matters for agencies and WordPress businesses. The headline is the launch of the WordPress Business and Agency Summit on the Monday before the main CloudFest event. We position it as a connector between the CloudFest Hackathon and the main CloudFest conference, and as a deliberate step toward giving agencies and WordPress businesses a more relevant, more pragmatic, more commercially useful program than the traditional “WordPress Day” format. We unpack the difference between WordCamps and CloudFest. WordCamps remain community-first, volunteer-driven, and primarily focused on education and connection inside the WordPress community. CloudFest is a for-profit, cloud and hosting industry conference with a very different scale, structure, and mission, and it can build a dedicated business-focused layer around WordPress without trying to turn WordCamps into something they were never designed to be. This year’s Summit expands the former WP Day into a full-day, two-track program, adds an exhibition area, and targets roughly 800 attendees in a more intimate setting inside a much larger 10,000+ person event. From Mark’s perspective, if we want growth and new partnerships, we need to attract agencies outside the WordPress community, and we need content that connects to direct business impact. That means talks about sales, pricing, go-to-market, agency operations, maintenance revenue, and what it really takes to move from agency work into becoming a product company. We also talk about the CloudFest Hackathon as a uniquely valuable environment for multi-day collaboration and deeper conversations that rarely happen at faster-paced conferences. Carole connects that to a broader goal: cross-CMS collaboration and strengthening the open web, so we do not end up with a future where a handful of platforms dictate where and how people can publish. We close with practical attendance advice, a reality check that the Hackathon is already fully booked, and the key dates for the Summit and the main CloudFest event. 00:00 – Cold open: editing workflow and “wave” marker for cuts00:01 – Welcome and setup: two guests, and why this episode is different00:02 – Carole: WordPress community background and CloudFest involvement00:03 – What CloudFest is: scale, audience, and Europa-Park as the venue00:04 – “Everything is different this year”: why we are doing this episode00:05 – The new WordPress Business and Agency Summit: where it fits in the week00:06 – Mark Weisbord (Greyd): the missing business layer in WordPress events00:07 – From “WP Day” to a bigger Summit: what changes operationally00:08 – Two tracks, full day, and a dedicated exhibition area00:09 – Why this format matters: connecting agencies, partners, and real-world solutions00:11 – WordCamps vs CloudFest: why they serve different purposes00:12 – Sponsor reality: ROI pressure, leads, and reaching agencies outside the bubble00:13 – Content shift: business impact over general tech presentations00:14 – WordCamps still matter, but they are not the vehicle for everything00:16 – Biggest change: bring in agencies outside WordPress, plus an entertainment factor00:18 – CloudFest vibe: opening party, Lords of the Uptime, and the venue experience00:23 – Practical advice: stay multiple nights for Summit welcome + opening party00:25 – Hackathon value: multi-day conversations and real collaboration time00:28 – Hackathon evolution: cross-CMS collaboration and protecting the open web00:33 – Why agencies benefit: broader ecosystem exposure than a WordCamp context00:36 – What the Summit covers: sales, pricing, playbooks, productizing, maintenance00:40 – How Summit pillars extend into t...
Transcript
Speaker A Welcome to within WordPress and with us today are not one, but two guests and I'll let them introduce themselves. But I wanted to say this is a special kind of podcast. I've not done a podcast with more than one before, so that's special. But also the narrative, the reason, the why we are here is different. So yeah, let's start with you, Karol. Welcome to the Within WordPress podcast.
Speaker B Hey, thanks for having me, Ramkus.
Speaker A Sure thing. Where can people know you from?
Speaker B I've been around in the WordPress industry for, yeah, I think it's my 10th anniversary this year. So I have been working with different companies within this industry for the past 10 years. I have been traveling the world with WordCamps. I have been organizing WordCamps for, for several years and I think I have been in general just, yeah, an enthusiast about the WordPress community and the industry. But I have also been involved into cloudfest for the past eight years. So.
Speaker A Yeah, yeah. And that is the topic of today, cloudfest. For those who have no idea what cloudfest is other than maybe you've heard the name somewhere somehow, please introduce cloudfest.
Speaker B Cloudfest is the biggest business conference in the cloud and hosting industry and it has been evolved from the former world hosting days into Cloudfest. And in general we're celebrating the 22nd edition this year, so we have been around for quite a while already. So yeah, you would meet more than 10,000 people of the cloud and hosting industries, mostly hosts, CSPs, MSPs, product owners, but also a lot of people involved in the WordPress business world and also hopefully a lot of agencies altogether locked down for three plus days in the biggest amusement park in Europe, which is Europa Park.
Speaker A It is a big park. It is really, really a big park. Yeah, Cloud Fest is. So I've been there a few times and the reason we are having this discussion now is you've asked me to present a do a presentation on the stage and which I happily said yes to. But one of the things you said that triggered me in the very most positive ways is everything is going to be different this year. And you also mentioned somebody who was being very vocal in making sure things were going to be different. He's quite silent currently, but
Speaker B spoiler alert, he's not gonna stay silent for much longer, I can promise you that. Yeah. So we are adding the very first time, the so called WordPress business and agency Summit into the Monday program preceding the main festival which starts on the Tuesday. So this, this new site event is going to be the natural connector between the cloudfest hackathon, which is the open source part of cloudfest, leading into the main business event, cloudfest, which is starting on the Tuesday. And while we were building ideas around what program we would like to offer to our target audiences and new target audiences at Cloud First, I had very interesting conversations with Mark. Mark Weisberg from grade. Yeah. And he gave us some really nice food for thought. But I think I'll let you elaborate more on that.
Speaker C Mark, thank you so much. And Remkos, also, thank you for having me. Yeah, I'm Mark. I'm CEO of Great. And not a regular to the WordPress community. I've been around for the last, I think three to four years. So this is my first visit in the open source community then. So WordCamps and those events, this was pretty new to me because I'm just a regular business guy. And being a big fan of the Hackathon and also of cloudfest and having traveled to some different wordcamps around the world, became clear to me that we have tremendous events all around the world and a huge community. And that's nice. But what we are missing is the business aspect. And as I'm not a front row guy in WordPress, so you don't see me a lot, but I'm very vocal when it's about enterprise, when it's about business, etc. And I was more or less nagging Carol, to talk more about business, have more business presentations and make agencies outside of the WordPress community being part of those events. Because on those word camps you only meet the community. But what we need to meet, we need to meet customers, new partnerships, etc. That is the reason why I'm here today, I guess
Speaker A what would, what, you know, this is going to sound. Up until last year, the Monday basically was called the WordPress Day, if I'm not mistaken, around, sorry, WP Day. Very important. And it started around noon or something.
Speaker B Yeah, correct. So I haven't been involved into the organization myself in the previous years, but I have always been around and it was, it was a smaller scale, although it was already very successful. We had packed rooms, but it was mostly one track half day event starting around noon, 1 1ish. And then there would be like four or five hours of sessions and then the program was over. So this year we're gonna, we're gonna change that a little bit. We're gonna have a full day program which is going to build around two tracks. So there's gonna be much more sessions. But what is also really interesting is there's going to be an exhibition area, like a small exhibition area for anyone who has been at cloudfest knows why it's important I make the difference as a small exhibition area because cloudfest really has a trade fair that I've failed to see anywhere else. Like these just like three floor booths. It's really, really different from what you
Speaker C would see at work.
Speaker B Yeah, I've seen a tiki bar at a, at a third floor once for, for a partner. It was, it was very impressed. So it's going to be a little, it's going to be a smaller scale, but I believe that is going to be very interesting because it also combines the value of the topics that we're going to see on stage with the business aspect of having our partners represent themselves and the solutions they bring to the table to help agencies grow their businesses now and in the future. And also using the new, the newest technologies and in a time where there's like almost daily and constant change going on, I think this is a really great opportunities for everyone involved for the agencies to connect in a more intimate space with each other, learn from each other, but also learn from our partners and also teach our partners what they could maybe do better to cater their needs. And I think that is. So we are expecting around 800 attendees and that is for WordCamp. This would be a rather big size already. But compared to Cloudfest which is a 10,000 plus people event, it is a rather intimate space and targeting a certain type of audience and taking into account their specific needs and cater towards that. And something that I'm really passionate about like, like building these bridges and to say it in, in, in, in in a way that, that really is at the core of what WordPress as a project is democratizing opportunities. I'm very passionate about that. I believe that I can contribute with what I am doing and with the help of people like, like Mark to make that happen to, to have the community and the smaller businesses connecting and creating win win situations.
Speaker A Yeah, I like that. I mean I, I've, before I joined the web world, so to say more than 20 years ago. I've been to large events as well and they were always a little too businessy. Right. So you'd be forced into talks that are just like what am I doing here? I, I know they're sponsors but can we not have something that tailors like to stuff that I need or I'm curious about it instead of, you know, that sort of thing. And it's nice to see that these types of events like so the WordPress has, the ecosystem is, I think, rapidly growing up in understanding that, yes, we are open source and wordcamps are part of that and everything, but we need another layer as well because there's other stuff happening as well. I'm assuming, Mark, that's what triggered you to say, hey, hold on, because I know you've been there at cloudfest last year, was that your first time?
Speaker C That was my first time as a sponsor or in the trade for of cloudfest. We have been part of the hackathon, but this was our first time having a booth at CloudFest. And I mean, when I think about that, I think about trade fairs and then I think about leads, contacts, and I mean, it's always for a small company like Grade, it is expensive to have a booth at an event like this. And furthermore, you need hotels and everything and you need your developers at the event, so they are not developing stuff. So for us, it's a huge investment. I was very motivated to go to cloudfest and the first, the first idea after last year was we want to have more contacts, we want to have more leads. And when I talk to other sponsors, it's every time the same. They under a lot of pressure. They have to sell, they have to get leads. And if you go to the regular events, they told me that you always meet the same people. And that's fun because I meet you guys and that's a wonderful thing. But we need to attract more customers, more business potential, etc. That's the reason for having those events. And for example, when I have a look at Great, then most of our customers are not part of the community and they would never think of going to a WordCamp because that's just not interesting for them or they don't know that this would exist. So I asked myself, if we want to have more agencies, more people outside of the community and make this a business event, what would be interesting?
Speaker B Yeah.
Speaker C And from that on, I thought about a total different approach because at WordCance we. We talk a lot of very general technological things. But as a business event, as talking about a business event, as you describe it, it's more about business impact, and I mean direct business impact. So everything on stage would have to be changed dramatically. I guess so. And I think that the WordPress business and agency Summit this year is one of the first tries to do that.
Speaker A Yeah, I agree. I like what you said with regard to this is how wordcamps work, and that's not what this is. I think it's a Good distinction to make because wordcamps having started a few and organized probably close to 20, there's a particular, like the, the, the goal of that is to have a learning and connecting environment for people in the WordPress community. And whichever way you, you try to make that wiggle a little bit to the left, to the left or to the right, the core is that you are primarily entertaining the WordPress community. And the WordPress community is the builders, the connectors, the developers, the agencies, but also, you know, the, all the layers that are in between. So the product people, the content writers, everybody who has a serious relationship with WordPress in the sense that it's more than just a tool, they log into every day and do their work. That to me is a Word Camp. And there will always be a place for wordcamps. Like that's not up for discussion. There's another discussion that goes in the line of does it make sense for work camps to want to cover all angles? And I'm very happy with cloudflare cloudfest direction now where that answer is actually, well, you know, sure, you can try and do that, but we're over here in a, what's already an industry leading event. Why don't we figure out how to best target Everybody working with WordPress who normally would never consider going to a Word camp. I, I, I really like that because like I said, I think actually I said this before we recorded, so I can't say like I said, but before the recording I mentioned that there's, that there's, there's a, a slow but steady move for everything inside of WordPress to become more professional. Not just on the business side of things, but just because we're at that stage. I guess the influx of AI forcing us to look at the things we can use, the tools that do the things that we found very difficult but now much quicker, all that sort of stuff, it's much closer to grasp. Right. You can lean into it harder and faster. And I really like the positioning with cloudfest is now turning itself into, I'm curious, Mark, what is the biggest suggestion for change that you've done that has been or is being implemented now,
Speaker C yet the agencies are outside of the community in the end because they will drive the change, because everything else is us. There have been a lot of events like Cloudfest who had a kind of WordPress day and what do you do in that case? You create a smaller version of a WordCamp and that doesn't make sense at all. As you said, you need to have the agencies outside of WordPress. Because if you see the whole market, then the community is just a small. It's the tip of the iceberg. And I think there are a lot of people who don't know that. So most of the business is outside of the community and these agencies can help us a lot. And the second thing is if you want to have a successful event today, you need the entertainment factor. And one example was that in Germany we had a lot of very interesting trade fairs like dmex, GUI etc, so everybody was traveling there every year. So that was irregular. And then we had Covid and there was that one festival that, yeah, that could still be on top and that is OMR in Germany. And what was the idea about omr? It was. It is not just. It is not just business, it is not just lectures and meeting, it's also an event. It's. It's having superstars, they are giving concerts or whatsoever, or TV stars, et cetera. So we need an entertainment factor because it has to be interesting. And you have to mention that if you have a, if you have an agency with 20, 25, 30 people, then sending three people to an event for three, four, five days, that is a lot, that's a lot of money. So it has to be worth it. And if it's a mixture of business and entertainment, it has a good chance to attract a lot of people.
Speaker A There is definitely entertainment at Entertainment at Cloud Fest. Are we having a cut all? Are we having the. What is the band name? The Lord of the Whatever?
Speaker B Lots of the Uptime.
Speaker A Lords of the Uptime. Are we having that band again?
Speaker B I mean, is that seriously a question? Of course, of course we do. And you'll see me first row as
Speaker A always for those listening, have absolutely no clue what that band is and who is in that. Can you share a little bit?
Speaker B So basically it is an all stars band of folks from the cloud and hosting industry that are uniting and they are practicing actually very little time to perform just greatly on stage once a year at Cloudfest. So it's basically your only opportunity, unless you know them as friends to see them perform. And it is really a rock metal vibe and a once in a lifetime adventure. When you see all the people like going crazy on stage and in front of the stage and dancing and singing and going all in together. It's the opening event for each cloudfest for the past few years.
Speaker A Yeah, yeah, it is. Do the people listening to this, do they know perhaps the lead singer?
Speaker B The lead singer? I'm not sure they would know, but they would probably know our dear Vito Pelek from uttering. Who is playing. He's. He's on the bass. Is he. He's not on the.
Speaker A Oh, okay.
Speaker B Is he. Please forgive me if you're listening to this and if I, if I, if I, if I got this wrong. But yeah, so I, so my, my personal challenge every year is to take the best possible picture of Vito on stage. And I have a few contenders in the meantime that are challenging me on this. But I, I always.
Speaker A He's a showman with the, with the guitar.
Speaker B Odd bass. Well, it is really guitar.
Speaker A Yeah, yeah, I think, I think what that is at the Monday evening, right?
Speaker B Correct. So that is always the. We call it. Yeah, it's actually the big opening party for cloudfest and then there's a street food festival in the main area of the amusement park.
Speaker A Big favorite of mine.
Speaker B Yeah. And then the concert usually starts around 9ish. 8ish. 9ish. And yeah, it's always a big. It's so much fun. Like in general. It is, it is, it is some experience. It's not your usual conference.
Speaker A No, because I was going to say the start of it. So if we again look at work camps, you, if you are a volunteer, a speaker, an organizer or whatever, you may have the. I don't know what the name of it nowadays is, but let's call it the speaker sponsor social media dinner the night before. And if you think you understand that I'm just going to help you out here. Now, Cloud Fest opening has nothing to do with that inside in terms of size and, and things going on and whatnot. There's a, there's a whole street, like a theme park street, like a whole street that is filled with first of all, people, but lots of food places where you can, I mean, if you leave that place hungry, you've done something really, really wrong. And then in. Inside of some of those buildings there's things happening and you know, it's a lot of fun. It's. It's nice to have these types of. I don't know, it's not a party, but it's, it's certainly a joyous event. Maybe that's the good.
Speaker B I would definitely recommend anyone that is listening to this that would join us for the WordPress business and agency Summit to make sure that they can stay at least two nights. So first of all, we will have the welcoming event to the summit which is happening on the Sunday night. So that is like an exclusive event for all the folks that are going to, that are Going to attend the summit on the Monday in a more intimate space again. And then on the Monday there is the big opening party. And if you stay one night longer, if you stay for the night of Monday as well, there's an opportunity first of all to be part of that party and to connect in a different setting with the folks that you have met during the Monday. And it will give you the opportunity to get the glimpse into the main event if you haven't done that in the previous years already and to find out for yourself, hey, is this something. I may want to stay longer in the next year or even become professionally involved as an exhibitor or. Yeah, there's tons of different possibilities also for partnership, basically everything can be customized. I would definitely tell anyone and I'm doing that for years already. Everyone in the WordPress industry and the community, you should at least once visit Cloud first and find out for yourself if it is your thing or not. But it is so, so valuable to get out of the WordPress bubble from time to time and to just broaden your horizon and then you can decide what you want.
Speaker A Yeah, exactly. I was waiting for you to finish your enthusiastic called people. Why don't you just come? Because it's exactly that. It's a different vibe. It's, it's, there's touches of WordPress because the topic is WordPress, but it's an entirely different vibe even the days before. So I remember Mark, you and I were so last year during the Hackathon, there's moments where you, you know, have lunch and interact with the people at the hackathon, but also around the hackathon, like there's people coming in and early and just saying hi and checking out the projects and I'd love for you to share a little bit more about what the Hackathon is in total later, Carol. But Mark, you and I met there and I think it's interesting to, to highlight how much of a network opportunity just being there in of itself is.
Speaker C Yeah, absolutely. First of all, I think I need to mention that I never take part in a project at the Hackathon, but we are a sponsor and I'm a regular hangaround. And why do I do that? Because it, it is basically the only event where you have two or three days in a row to talk to someone about an idea. Because I mean, you know that you meet somebody at a Word camp, for example, and you talk about something, cooperation, an idea whatsoever. But you might need 24 hours to think about that and then add some different things to it and Hackathon is the only chance to meet that person the next day and tell them, yeah, I heard what you say and I think we should go this or that direction. And that's totally not possible at a Word camp because everybody's so busy and the whole vibe about the hackathon was always about communication for several days. So it is a dialogue and we used that last year and this is also why we do a lot of things together. We had the time to discuss that and that is only possible at Hackathon. It is a wonderful event to recruit. It is a wonderful event to meet, obviously to hang around, incentivize your developers and other people in your company. And this is why I love Hackathon and, and also this year I will hang around, definitely.
Speaker A Yeah, I think that's the, the, I mean a lot of these events that we go to and, and I've seen, I see you both at all the various events we have, right? There's from Press Conf to work camp, Europe, WordCamp US, you name it, and there's value in every single one of them. But I, and I think it's, it's difficult to stress how different this environment is because one of the things I, I like about the hackathon, specifically, it's an open source hackathon. It's not a WordPress hackathon, meaning you sit at the table with people who kind of glance at WordPress and go like, yeah, no, that's not for me. But I hear let me do typo three. Let me do, you know, whatever. Joomla Magento. I don't know, probably not Magento, but you know, all of these other tools that are adjacent to what WordPress does, but brings a whole different crowd, like a different type of mental model, I would even say. And yet it's still part of the open source. Has the hackathon always been that way?