I just got back from PressConf 2026 in Tempe, Arizona: four days of unusually candid conversations about the business of WordPress. Not unusually candid for a conference. Unusually candid, full stop.
This wasn’t a gathering of people celebrating what’s working. It was a room of operators, founders, and builders being honest with each other about what isn’t, and more importantly, about what they’re doing about it. I left with pages of notes and a few convictions I didn’t walk in with. Here are the ones worth sharing.
1. WooCommerce needs to stop fighting the wrong battle
One of the sharpest talks of the event came from Bryce Adams, Founder of Metorik, who has spent a decade working with WooCommerce stores at every scale, from a hundred orders a day to tens of thousands. His diagnosis was blunt: WooCommerce has been trying to compete with Shopify for years, and that fight was lost before it started.
The numbers make the case. Shopify processed $292 billion in GMV in 2024, growing 24% year over year. WooCommerce’s estimated annual GMV sits somewhere between $30–35 billion. Those aren’t remotely comparable figures, and trying to position them as a contest misses the point entirely. What Bryce argued, and what resonated across the room, is that WooCommerce isn’t losing because it’s inferior. It’s losing the narrative because it hasn’t owned one.
The real story is this: tens of billions of dollars a year flow through WooCommerce stores. Merchants doing seven and eight figures quietly run their businesses on the platform with no drama, no migration plans, no ceiling in sight. Stores the general public would recognize are on WooCommerce and nobody talks about it. Meanwhile, Shopify has built an entire content machine around merchant success stories. Bryce’s point was simple and worth repeating: the ecosystem fills the gaps Automattic won’t. Every shortcoming in the platform is an opportunity for someone in the room to build a business.
That framing (shortcomings as a business model) ran through more than one conversation across the week.
2. WordPress has a reputation problem, not a product problem
Anthony Ferrara, Principal of design agency Oxy, gave what might have been the most provocative talk of the conference. His title: The WordPress Identity Crisis. His argument: WordPress is its own worst enemy, and the problem is positioning, not product.
He comes at this from the sales floor. On a typical week, he’s on four calls trying to convince enterprise CMOs that WordPress is the right platform for them. If the decision-maker is under 35, saying the letters “WP” can stop a conversation cold. They see it as legacy. Something their predecessors used. He described it as trying to sell a house that’s on fire while being genuinely excited about it. The bones are extraordinary, but the brand is giving off smoke.
The data adds context. WordPress powered roughly 43% of the entire web as of early 2025, but that share has begun its first meaningful decline in over 20 years, sitting at approximately 42.5% in early 2026. More telling is the “None” category in CMS tracking data (sites built without any CMS at all) which is growing for the first time in years, sitting around 28.6% of all websites. The threat to WordPress isn’t Webflow or Framer or EmDash. It’s the growing number of builders who have stopped asking which CMS to use.
Anthony’s prescription was pointed: stop democratizing mediocrity, start setting standards. Don’t sell accessible-for-all, sell built for the best. The platform deserves it. The community, in his view, just hasn’t decided to own that story yet.
3. Agencies need to stop selling WordPress and start selling outcomes
Justin Livesay, CEO of Fueled (recently merged with 10up), brought a genuinely outsider perspective: a long engineering career, time running Tony Robbins’ live event technology globally, and then landing in the WordPress agency world through a merger with 10up. His talk was titled WordPress: An Outside Looking In, and the plainness of his observation was its strength.
His core argument: WordPress agencies consistently lose enterprise deals not because the product is wrong, but because of how they present it. Buyers don’t walk into a purchase knowing they need a WordPress partner. They walk in knowing they have a specific problem: a loyalty program that needs to scale, content operations that have outgrown one team’s capacity, a digital experience that needs to integrate with a dozen other systems. The agency that shows up talking about WordPress loses to the agency that shows up talking about the problem.
He pointed to Salesforce as the contrast. At Dreamforce, which drew 45,000 attendees in 2024 from 140 countries, you cannot walk three feet without encountering a customer success story. Every session, every booth, every keynote moment is organized around businesses that solved real problems using the platform. You leave feeling like you’re missing out if you’re not a customer. Justin’s observation was that he left WordCamp feeling well-supported as a builder, but with no idea whether anyone was actually paying for any of this. Customer centricity was almost entirely absent.
The shift he’s pushing at Fueled: don’t run campaigns asking if someone needs a WordPress partner. Run campaigns about the outcomes you can deliver: loyalty, content operations, digital governance. Let WordPress be the undisclosed mechanism behind them. This isn’t a new insight in the enterprise software world. Research consistently shows that enterprise buyers in 2025 and 2026 are demanding measurable, quantifiable outcomes, not platform features. Agencies that lead with the platform are selling to the wrong decision-maker. The ones that lead with the problem get upstream in the buying process entirely.
He also made a point that stuck: agencies are the best storytellers in the WordPress ecosystem, because they’re the ones actually solving the problems. Nobody else is. Not Automattic, which doesn’t do the implementation work, and not hosting companies, which typically don’t own the strategy. If the WordPress ecosystem is going to close the customer-centricity gap with Salesforce or Adobe, agencies are the ones who have to do it, collectively, by telling more and better stories about what they’ve actually built.
4. The hosting industry is starting to hold itself accountable
Not every conversation at PressConf was about WordPress’s identity or AI’s disruption of the plugin economy. One of the more grounded sessions came from a panel on hosting industry trust, featuring David Snead, Co-Founder of the i2 Coalition, Chris Ghazarian, COO and General Counsel of DreamHost, and Jared Sine, Chief Strategy and Legal Officer of GoDaddy, moderated by Rae Morey, Publisher and Editor-in-Chief of The Repository.
The subject was the Secure Hosting Alliance, a working group within the i2 Coalition that has built a certification program for hosting providers built around four pillars: transparency, infrastructure accountability, abuse protocols, and government request handling. On the surface that sounds procedural. In practice, it addresses something agencies deal with constantly but rarely discuss openly: how much do you actually know about the host you’re recommending to a client?
David Snead put the transparency pillar plainly: certified hosts are required to show customers their contract before they sign. As a lawyer, he noted, you’d think that would be table stakes. It isn’t. The SHA has already rejected two applicants, one for refusing to display contracts upfront, another for having no monitored abuse contact. These aren’t edge cases. They’re industry norms that the certification is trying to raise.
Chris Ghazarian grounded the conversation in something more tangible. DreamHost was one of the founding members of the SHA, and their commitment to data privacy wasn’t abstract. In 2017 the DOJ issued subpoenas targeting visitor data from a website hosted on DreamHost related to inauguration protests. DreamHost fought it publicly and won, even as other hosts quietly complied. His point: when you recommend a host to a client, you’re also recommending how that host will handle their data if it’s ever requested by law enforcement. Most agencies have never thought about that.
Jared Sine, whose company GoDaddy is currently going through the SHA certification process, made the case for why independent third-party standards matter at all. Self-assessed standards are too easy to maneuver around. Having an external body that can actually revoke a trust seal, and has the teeth to do it, is what gives the certification meaning. As he put it, it’s not a rubber stamp, and that’s exactly the point.
For agencies recommending hosting to clients, the SHA’s public principles are worth bookmarking even if the host you’re recommending isn’t yet certified. The criteria are openly published and give you a concrete framework for evaluating any provider: Do they show contracts before signing? Do they have a monitored abuse contact? Do they have a documented process for handling government data requests? If the answer to any of those is no, that’s worth knowing before you stake your reputation on a recommendation.
5. The infrastructure and strategy gap is real, and we’re doing something about it
Several conversations across the week circled the same structural problem: enterprise digital environments are increasingly complex, rebuilds are enormously expensive and chronically recurring, and the teams responsible for them are typically managing a fragmented set of vendor relationships with no one accountable for the whole. Hosting owns uptime. Agencies own delivery. Internal IT owns everything else. Nobody owns the platform end to end. That gap is where platforms quietly go to die.
Gartner’s 2024 infrastructure research puts a number on it: nearly 40% of enterprise IT budgets go toward maintaining technical debt rather than building new capability. Not solving it. Funding it. Repeatedly.
This was the backdrop for conversations Lasse Hall, Servebolt’s CEO, and Karim Marucchi, CEO of Crowd Favorite, had been building toward for some time, and which we announced formally at PressConf this week: The Evergreen Platform.
As Lasse framed it in our announcement: “Saying yes to infrastructure only solves half the problem.” Servebolt’s entire stack, owned hardware through CDN, no PHP worker limits, sub-100ms response times globally, gives enterprise environments the infrastructure flexibility most hosting providers refuse to offer. But the gap that causes rebuild cycles isn’t usually the infrastructure. It’s the absence of continuous governance sitting above it.
That’s what Crowd Favorite brings. Karim’s team has seventeen years of enterprise work with organizations like Nvidia, Disney, and Providence Healthcare, in environments that have never fit a standard hosting plan and never will. As the Crowd Favorite announcement put it: “Nobody owns the gap between hosting and strategy. Until now.”
The Evergreen Platform closes that gap under a single contract. Servebolt owns the underlying stack. Crowd Favorite owns architecture, roadmap, codebase health, and security hardening at the application layer. One team responsible for everything built on top. The entry point is Expert-Led Migrations: fixed scope, known cost, risk contained at every stage. From there, the platform stays current by design rather than by crisis. Quarterly State of the Estate reporting. Technical debt paid down as an operational habit. When your team is ready for AI workflows or new integrations, the architecture is already prepared.
If you’re a CTO managing a complex multi-site environment, or an agency tired of the finger-pointing that happens when infrastructure and strategy live in separate rooms, this is built for you. Full details from both sides: Crowd Favorite’s announcement and Servebolt’s announcement.
6. Stop being a WordPress plugin. Start being a product.
Matt Cromwell, Founder of Roots & Fruit, gave what was probably the most structurally ambitious talk of the conference: a full reframe of what it means to be a WordPress product company in 2026 and beyond.
He opened with the industrial revolution. Before mechanized bread slicing, people cut bread by hand. The machine didn’t destroy the baker. It changed the nature of the baker’s job, raised output expectations, and eventually made the old way unthinkable. AI, he argued, is the same inflection point for the WordPress plugin economy. The question isn’t whether the shift is happening. It’s whether you’re the farmer with hand tools or the landowner buying the tractor.
His diagnosis was direct: utility plugins, the small single-feature tools that solve one narrow problem inside a larger stack, are the most exposed. They’re the easiest to replicate with a prompt, the easiest to skip when a merchant is simplifying, and the hardest to defend when a SaaS alternative comes in with a cleaner story. Katie Keith, Founder and CEO of Barn2 Plugins, brought the data to back this up: new plugin sales have been declining for two years, driven partly by reduced Google organic traffic and partly by a shift in how people discover tools. Notably, Katie left PressConf with a clear-eyed plan to address it, actively exploring expansion into Shopify and new product directions to get back to growth.
Matt’s prescription: stop thinking of yourself as a company that sells WordPress plugins, and start thinking of yourself as a company that solves a specific customer problem. The platform is incidental. The pain point is the product. He plans to build his next product around the problem of email for businesses, not a WordPress plugin, not a WooCommerce extension, but a solution to a problem that may or may not involve WordPress at all. The distribution, he argued, now has to be earned rather than inherited. Organic search and the freemium model on WordPress.org are no longer sufficient. The most important person you can hire on a product team today isn’t a developer. It’s a marketer.
7. Build a business that doesn’t depend on anyone fixing anything
If there was a through-line across the week, it wasn’t anxiety. It was a particular kind of agency: the refusal to wait.
Bryce Adams put it plainly in his WooCommerce talk: the gaps in the platform are the business model. Every problem Automattic hasn’t solved is a reason for someone in this room to exist. Barn2 Plugins, Metorik, Atarim, Kestrel: the businesses that have built real, durable revenue in this ecosystem did it by solving problems the platform left open, not by waiting for the platform to close them.
Vito Peleg of Atarim extended the point into agency operations with his session on the agentic web agency: the idea that AI is going to allow agencies to manage orders of magnitude more client relationships than a traditional team structure permits. The constraint shifts from headcount to systems. The agencies that are building those systems now will have a structural advantage that compounds.
Katie Keith’s talk was the most personal version of this. She ran through a decade of decision-making that consistently prioritized resilience and adaptability over scale for its own sake. Delegate early, design around your life, don’t let any single dependency become existential. The business she built survived a co-founder departure, a child’s medical crisis, a move across Europe, and a prolonged SEO headwind, because she had designed it to survive disruption, not avoid it.
The developers on the plugin economics panel, moderated by Rae Morey of The Repository with panelists Matt Medeiros and Eric Karkovack of The WP Minute, spent considerable time on the market share question: what does WordPress at 20% look like? Nobody found that prospect catastrophic. The consensus, expressed well by Matt Medeiros, was that a smaller, more focused WordPress community focused entirely on outcomes for real businesses might actually be healthier than a platform trying to be everything to everyone.
Closing thought
PressConf doesn’t feel like most tech conferences. There are no product launches staged for press. Nobody is performing optimism. The conversations are real because the people in the room have real businesses at stake.
What I took away is that the WordPress ecosystem is going through something genuinely difficult: leadership uncertainty, AI disruption, a reputation gap it hasn’t figured out how to close. And simultaneously doing what it has always done: building businesses in the gaps, telling the truth to each other, and showing up.
The ecosystem was built by people who decided not to wait for permission. It’ll be extended the same way.
See you at PressConf 2027.
(Image credit: PressConf.events)
