In June 2025 I started googling seaside venues near Palermo.
A small spreadsheet, a very optimistic (!) business plan, and the idea that WooCommerce developers deserved a conference that felt like ours.
A few months later I was sweating through a 42°C venue tour, wondering if I’d survive long enough to actually run it!
I hadn’t organized an international conference before, so most of what happened between that Google search and opening day was figured out as I went, in public, often on the fly…
Then, in April 2026, 101 people showed up in Sicily, and another 107 joined online for Checkout Summit Reloaded a couple of weeks later.
This is what actually happened in year one, the parts I got wrong, and why, despite all of it, I’m doing it again!
The spark
Checkout Summit started in a ChatGPT tab in June 2025, brainstorming on a conference name that wouldn’t get me a cease-and-desist letter.
Honestly, I just wanted to sit in a room with the people I already talked to online about… WooCommerce hooks and filters, business, marketing, content; also, I wanted that room to be in Sicily, close to my place, to reduce burnout potential.
That’s the part I’d tell anyone thinking about running their first conference: you don’t need permission or a fully-formed plan to start. You need one name, a simple website, and the willingness to keep going after it.
Building it in public
From the start, I ran most of the decisions as public polls on Twitter: ticket pricing, format, little details most organizers would decide behind closed doors. It kept the community invested before there was anything to buy, and it meant the event felt co-owned rather than sold to.
I only overrode a poll once. The crowd voted to put the attendee intake form at checkout; I moved it to the Thank You page, the confirmation email, and My Account instead (to me, the Checkout page is not the place to ask someone ten questions about their job title).
Building in public doesn’t mean outsourcing every call… it means showing your work, including the one time you disagreed with it (boy, was I wrong lol).
The venue hunt
Picking the venue took quite a lot of work given my requirements: beach hotel (!), close to the airport, and that had a decent conference room.
I visited the final three candidates in person, but in July 2025 the heat was shocking… my own note from that week was something like “either I die or Checkout Summit happens next year”!
The venue I picked, the Saracen Hotel, almost didn’t get a look. Walking in from the car park, the back of the building looked dated and forgettable—I nearly wrote it off on the spot. Then I walked around to the sea-facing front and understood immediately why this was the one. First impressions from the wrong entrance nearly cost me the right venue!
The hard part: sponsors
Content and tickets, I could kinda plan for. I know almost everyone in the WooCommerce dev space, so honestly I always said to myself that “finding 150 people to fly to Palermo wasn’t hard“.
In fairness I was *almost* right there, if it weren’t for two big 2026 problems:
- Cancelled and re-routed flights due to the Middle East problems, that stopped many people from making it to Sicily or afford a 4 flights detour
- Serious budget cuts from agencies and WordPress companies, that stopped sending people to conferences
With 150 being my attendees goal, I got 101 amazing people to register on day 1 right after the welcome dinner. A couple less, and I would have been disappointed 
Honestly, it was a really good bunch of people, and 101 sounded like the perfect quantity (and quality).
Sponsors were harder. Really, really hard. And those budget cuts came at the worst time for me.
Thankfully, WooCommerce secured the headline sponsorship, two more got booths because it was perfect timing for them as companies, but the rest it was a lot of… “This is amazing, we’ll sponsor!” conversations that dragged for months and then never happened.
I spent a fair amount of the last months trying to find plan Bs, plan Cs, whatever could help me recover some revenue (together with budget cuts). It worked out. Lots of friends, and friends of friends, joined as “Founding Contributors”, and allowed me to keep going:
The numbers
Here’s where it landed: 101 attendees in Palermo, against a target of 150, with 12 speakers across the two days. Short of the goal on headcount, but sponsor and contributors revenue meant the event turned some profit—which, for a first edition with zero track record to point to, I’ll take!
Then came Reloaded: a virtual follow-up 2 weeks later for everyone who wanted to be part of it but couldn’t travel. That brought in 100+ more people, which means year one actually reached over 200 WooCommerce developers and agency owners, split between a hotel terrace in Palermo and wherever everyone was watching from.
What worked, what I’d change
What worked: keeping it small and building it in public. A 150-person cap made the in-person event feel like a room full of people who actually wanted to be there, and not a trade show. And running decisions as public polls meant the community showed up already invested, because they’d helped shape it.
Also, I personally survived and did not burn out. That was, honestly, one of my main goals, and I’m happy to tell you it went well for me too.
What needs to change:
- I’d start sponsor conversations earlier and expect the cycle to take longer than it looks like it should. Big companies move slowly even when they’re interested.
- I’d make sure the talks and audience are fully aligned. The year 1 excitement was sufficient, but only once I define an actual topic this can get better and better.
- I’d make sure I’m not alone organizing all this; a fresh pair (or more) of eyes is always a good thing!
- I’d try to read the post-event survey again, and look for opportunities to grow / improve.
- I’d make sure there are more networking and fun opportunities
- And why not, at least two amazing workshops
- And finally, I’d love to welcome more people, hoping that there are no last minute worldwide geopolitical problems…
Why I’m doing it again in 2027?
Because it worked, even with the parts that didn’t go to plan. A first-time, self-funded, in-person conference drew 200+ people across its live and virtual versions; that’s not something I want to leave on the table.
I want Checkout Summit to be an annual thing, and I’m already thinking about how it pairs with the Business Bloomer Club so the community doesn’t just show up once a year and disappear in between.
So, hello Checkout Summit 2027
If year one taught me anything, it’s that the people who show up early are the ones who make the room worth being in.
So if you were in Palermo, at Reloaded, or just watching from the sidelines last time, this is where you get in before it’s a scramble.
Tickets are on sale now; and here’s who joined so far:
So, yes, I’m doing it again. And hopefully, again and again.