I’m not exactly known for being fast at posting event recaps (or posting anything for that matter). Circle Day happened back in September, and here I am, in November, still processing. So here's the full story — how the event was (spoiler alert: perfectly organized), what I learned, and why it confirmed that Squarespace is exactly where I want to be as a designer.

Conversations at Squarespace HQ

The day before the main event, Community Leaders like me were invited to a smaller session with Anthony Casalena (founder and CEO), Paul Gubbay (Chief Product Officer), and Taylor Lagoy (Associate Community Manager). It was an open conversation about where Squarespace is heading, and it shows how they’re listening to their design community. Later came the welcome party (where I may or may not have had too much fun) with drinks, jazz band, and great company.

It all took place at Squarespace’s headquarters in NY — think bright light, city views, and minimalism. Can't beat that.

Meeting the People Who Changed the Game

A huge highlight for me was meeting Puno and Mindy from ilovecreatives.com — creators of the Squarespace course that started my own journey into web design. Full-circle moment, for sure — but also just plain fun to hang out!

I also finally met Florence — who’s not just a super talented designer but now officially my bff (merci for speaking French with me 🤍). And there were so many others I was thrilled to chat with: Christy Price, Sam Crawford, Will Myers, the team from SquareKicker — truly some of the coolest (and kindest humans) in our field.

Before I dive into what I learned, I have to say this: the entire Circle Day experience was so thoughtfully organized. Every detail made us feel welcomed, seen, and genuinely valued as part of the community. Huge congratulations to the Squarespace team for pulling it off online and IRL.

Key Takeaways from Circle Day

Let’s get to the good stuff. These were the updates from Squarespace Circle Day 2025 that made me gasp (because who wants to read boring stuff):

Squarespace for Pros: More Power, Same Simplicity

This was one of the biggest reveals — a dedicated set of tools for professional creators. Squarespace for Pros adds more flexibility and advanced controls for those of us who want pixel-perfect designs without leaving the intuitive builder we all love behind.

To me, this is where Squarespace continues to shine: they’re actually making professional-grade design more intuitive and accessible. Meaning, we get to spend more time on strategy and less time on development gymnastics and workarounds.

Which brings me to… Stacks. Another big feature that designers will love. It'll let us arrange, align, and distribute blocks in a fixed, structured order. Think of it like arranging your blocks into “shelves”, so everything will stay tidy, even when the screen size changes. (SO. HOT.)

Beacon AI: Support That Works With You

Another big feature was Beacon AI, a built-in assistant designed to help with repetitive or time-consuming tasks.

I respect everyone who prefers not to use AI, but as someone who uses it strategically in my processes, seeing Squarespace invest in this direction felt validating. I use AI to expedite tasks, not replace creativity and skills. It’s a tool, a powerful one — and I’m all for that.

A full list of new and upcoming features can be found at Squarespace Refresh 2025.

Why Circle Day Reinforced My Beliefs

Squarespace’s roadmap feels stronger and clearer than ever. The platform is clearly stepping into territory that belonged to Webflow and Framer — but with a more inclusive and simpler approach. (My beloved, magical word.)

For those of us who build for busy entrepreneurs, and for us busy entrepreneurs, these updates mean faster turnaround, easier edits, and websites that not only look good but work hard behind the scenes (you know that's my jam).

At its core, Circle Day wasn’t about hype or tech demos (although some made the room go “wow” out loud. 😂 It was one of those moments when you look around and think, “You're as excited as me about this. We get excited about websites. That’s awesome.”). It was a reminder of how we thrive when we combine creativity, innovation, and community.

Squarespace has always been about making website creation (and all-in-one business management) accessible without compromising quality, and this year proved they’re still walking that talk. The platform is evolving for those of us who care about strategy as much as aesthetics — and that’s why I’ll keep building here.

The Future of Designing on Squarespace

Between new pro tools, Beacon AI, and a stronger sense of collaboration and community, Squarespace Circle Day 2025 showed that the future of web design is accessible, creative, and so fun.

These updates show how Squarespace is evolving in ways that give designers tools that help us deliver strategic, beautiful, conversion-friendly online business solutions without overcomplicating things.

As a designer, Community Leader, and Squarespace-obsessed, I left New York thinking: if Squarespace is evolving, so should we. See you there next year.