What I learned and a real look behind the scenes.

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. But that’s kind of how I like it. I’d rather share the full story — what actually mattered, what I learned, and why it confirmed that Squarespace is exactly where I want to be as a designer.

So grab your favorite snack (mine’s pizza, ofc 🍕), and let’s chat about what went down at Squarespace Circle Day 2025 — straight from New York City.

Conversations at Squarespace HQ

The event took place at Squarespace’s headquarters in the West Village — a space that’s as design-forward as you’d expect, but still felt surprisingly down-to-earth. Think bright light, thoughtful details, and people who actually make websites for a living — not just talk about them.

More than 200 designers showed up in person, with thousands joining online. Before the main event, Community Leaders like me were invited to a smaller session with the leadership team, including Anthony Casalena (founder) and Paul Gubbay (Chief Product Officer). It was open conversation about where Squarespace is heading and how they’re listening to their design community.

Later came the welcome party, where I may or may not have had too much fun. But that's a huge (if I'm being honest, the main) reason why I transitioned from lawyer to designer. Creative work doesn’t have to be serious all the time.

I met designers I’ve followed for years, made new friends, and confirmed that the web design world is full of genuinely kind, talented people.

Meeting the People Who Started It All (For Me & Many More)

A huge highlight for me was meeting Puno and Mindy from ilovecreatives.com — the duo behind the Squarespace course that started my own journey into web design. I told them how their program gave me the confidence (and the push) to build my first client site. Full-circle moment, for sure — but also just plain fun to hang out and laugh together in real life.

I also finally met Florence — who’s not just a talented designer but now officially my bff (merci for speaking French with me, Florence 💛). 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.

Key Takeaways from Circle Day

Let’s get right to it. These were the updates from Squarespace Circle Day 2025 that made me gasp (because who wants to read boring corporate 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 shines: they’re actually making professional-grade design more accessible. When we're overwhelmed and just want our website to work, this kind of upgrade matter. 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 adding invisible shelves to your layout, so everything stays 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 AI 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.

Squarespace’s roadmap feels stronger and clearer than ever. Between these key takeaways and Final Touch (another game-changer for layout control), the platform is clearly stepping into territory that once 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).

Why Circle Day Reinforced My Beliefs

If I had to describe the overall vibe of Circle Day, it would be collaborative. There’s something special about being in a room full of people who just get you.

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 now all-in-one business management) approachable 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.

I came home from New York proud of my community and inspired by what’s next.

The Future of Designing on Squarespace

Between new pro tools, smarter AI, and a stronger sense of collaboration, Squarespace Circle Day 2025 showed that the future of web design is accessible, creative, and yes — still fun.

The updates announced show Squarespace is evolving in ways that give designers real freedom and real power. The platform is offering tools that help us deliver strategic, organized, conversion-friendly websites without overcomplicating things.

As a designer, community leader, and proud Squarespace nerd, I left New York thinking: if Squarespace is evolving, so should we.