If you’re reading this, you probably couldn’t make it to Palermo by now. But I do want to say this clearly: if Checkout Summit 2026 works, there will be a year two. And if sponsorships and contributors remain stable, there will be many more years after that.
That’s the first important point. This isn’t a one-off experiment anymore. It’s something I want to keep building, slowly, but consistently.
Right now, I’m writing this on the pre-event day. I’m setting things up, picking up attendees from the airport, and making sure my family is checked into the hotel so we can all settle in before the welcome dinner. It’s a bit chaotic, but the good kind.
Sponsors have been incredibly generous this year. Without them, I would have likely ended up in the red. I would have loved to sell more tickets and more sponsorship slots, but travel in 2026 is still… uneven. That said, having around 101 people in Palermo already feels like a win. A real one.
Why Checkout Summit exists
Checkout Summit exists because I felt we weren’t talking enough about WooCommerce in a focused, honest way. Yes, we need to talk about Woo more openly.
Honestly, “everything is fine” doesn’t exist. I wanted to hear about the practical, sometimes uncomfortable way that developers, agencies, and founders actually experience every day.
What’s working. What’s breaking. What’s too complex. What’s still surprisingly powerful. And what we should stop pretending is fine.
There’s a strange gap right now: WooCommerce is still everywhere, still powering a huge chunk of stores, still evolving—but the conversation around it often feels either too shallow or too fragmented.
That gap is exactly where events like Checkout Summit sit.
Today feels different
Today, as everything comes together, it feels different from when this idea started. There’s less hype and more reality.
People are not coming here to be sold a vision. They’re coming because they want clarity. They want to hear what others are actually doing with WooCommerce, how they’re solving problems, how they’re adapting (to AI?), and where they think things are going next.
That’s also why I’m happy this is not a massive conference. It doesn’t need to be.
A room of 100+ people who actually build and work with WooCommerce is more useful than a thousand passive attendees.
Speakers and what I expect
You can see the full list of speakers here: https://checkoutsummit.com/speakers/. What I expect from this lineup is not perfection or polished keynote energy.
I expect patterns, disagreements, and someone to say something that quietly shifts how someone else thinks about development, conversion, or even business strategy.
And personally, I’m hoping for three things:
- A connection between people who wouldn’t normally meet.
- A new idea I can’t stop thinking about on the way back home.
- A bit of sun and calm between sessions, because Palermo is not the worst place to relax.
And, if I’m honest, the motivation to say yes to a second edition!
Why this matters right now
There’s a tendency in tech to assume that everything important is already known, just redistributed in slightly different formats.
That’s not true here.
WooCommerce is still evolving. The ecosystem is still changing. And the gap between what people think is happening and what is actually happening in real stores is still quite wide.
That’s where conversations matter more than content.
The only real CTA
If you’re still on the fence, this is probably the last moment where it still makes sense to decide. There are still tickets for {Reloaded}, and they are intentionally kept accessible.
Not because the event is “cheap,” but because I want the people who are actually building, breaking, fixing, and scaling WooCommerce stores to be in the room.
This is one of the few places where you’ll get a concentrated view of where WooCommerce is heading, what people are investing in, and what is quietly being phased out.
If that matters to you, you already know what to do.
