Squarespace anticipates what’s coming next in the industry by banking on their source material: human creativity.
Circle Day 2026: Reshaping Web Design
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“I don’t know how to describe it,” Squarespace President Kevin Doerr admits in his opening keynote at Circle Day 2026, hosted both live from the NYC HQ and online on Wednesday, October 21. “I find it at times exhilarating, other times I find it terrifying.”
I may not have been there in person, but even I could feel the energy in that room from across time zones — a mix of anxiety and anticipation for what’s to come. As part of Squarespace’s inner circle of professional designers, we’ve always had this event to mark on our calendar each year. But perhaps deep inside I knew, in the midst of unprecedented AI advancement, that this one would be different.
This post was sponsored by Squarespace. Squarespace is the first platform where I learned to design websites, and it remains one of my most recommended platforms. Every opinion here is my own.
In some ways the opening keynote was a continuation of last year’s feature rollouts: an expansion of Stack functionalities, the introduction of vertical videos, an option to lock blocks in the Fluid Editor, the ability to autosave drafts and version history, and the addition of SMS campaigns.
This year, I had the honor of presenting a site showcase at Circle Day, where I reimagined one of Squarespace’s current templates using the platform’s newest pro features like stacks and block animations. If you’d like to see it in action, here’s the 20-minute walkthrough.
Product Highlights from Circle Day 2026
Advanced Stacks improvements. Due to popular demand from Circle members, Squarespace has iterated on Stacks by adding background colors (solid, gradient, image), clickable links, and gap controls.
Video aspect ratios. Squarespace designers can finally upload videos in portrait orientation for TikToks, Instagram reels, or YouTube shorts.
Block locking. With the new Lock function for Squarespace blocks, you can now freely edit Fluid Engine sections without having to readjust your layers.
Bye, save button. Say hello to drafts and version history on your Squarespace Editor. Autosave takes care of design documentation in the background.
AI code blocks. Code blocks get an upgrade this year with a rollout of interactive React (JavaScript) and native vibe-coding components.
Squarespace MCP for commerce and websites. The brand new Squarespace MCP (model concept protocol) allows your AI tool of choice to manage your websites on your behalf.
SMS Campaigns:. Users can now orchestrate text campaigns directly on Squarespace, so you can tap into a marketing channel to keep in touch.
However, the major updates this time around have undeniably been the brand’s moves to integrate AI more deeply into the way we build sites. Code blocks will soon be outfitted with interactive React (JavaScript) and vibe-coding components. Squarespace is also eager to connect your websites to your AI assistant of choice through MCPs. And the biggest announcement of all was Forma, Squarespace’s new AI-native software builder which can support complex website and application architecture.
These changes can be a lot to take in. Maybe you can feel it, too — the ground shifting beneath your feet, shaking up web design and development as you once knew it. Seems like we’re all trying to make sense of what this entails for our industry moving forward. Well, here’s my personal take from selected Circle Day sessions that stayed with me:
1. AI sets the new baseline for client expectations
“A client hands over a loose vibe and expects us to build a website around it… now AI has made that expectation universal—just type in plain English.”
—Rose Cawley and Hailey Benton, The future is a vibe
The sky’s the limit with generative AI these days; there’s barely a technical ceiling to what we can create for our clients. But this also raises the floor for client expectations: Others are catching on to how they’re a few prompts away from a vibe-coded site of their own making, either from AI-assisted methods like Squarespace’s Blueprint AI or AI-led initiatives such as Forma.
Of course, there’s more work that goes into conjuring a website than just a few magic words. When we use AI-led tools to build websites, there’s a lot of space for creative freedom here—perhaps too much freedom for the average user. Those who are less tech-savvy would actually benefit from more guardrails as guidance for what is possible and permissible in a standard site.
That said, fully vibe-coded websites still need an expert eye, someone to steer the tool in the right direction and verify what it produces. I even wrote about my sentiments at length in a previous blog post. Large language models are weighted towards the statistical average by design, so you can’t count on them to produce creative risks or novelties. Yet to the untrained eye, they’re “good enough.” The sheer availability of generative AI has turned what was once average into the bare minimum by mere convenience. Anything less than that and business owners won’t see the point in hiring you.
So now it seems deceptively easier to start your own website from a simple idea. Then again, isn’t that what they used to say about Squarespace no-code templates a few years ago?
2. Design is a series of strategic decisions
“AI builds what you tell it. My role is to help determine whether you’re building the right thing in the first place.”
—Nicole Martinez, How a website fits into your client’s bigger marketing plan
In the past, I used to encourage my students by enticing them with the possibility of turning their creative ideas into digital reality. That future has practically arrived on your doorstep thanks to generative AI.
Today I find that web design becomes less an exercise in technical prowess as it is a matter of strategic thinking. Experience is now signified by taste and discernment: In a world where you can build anything, how can you tell what’s worth building at all? Just because you can, doesn’t mean you should.
“After you make enough websites, you make enough things, something kind of happens. You stop asking, ‘How do I make websites?’ and you start asking, ‘How do I want this website to feel?’”
—Puno, Opening keynote
As the expert designer, resist the urge to step in and dwell on the smaller, less significant details that can be automated away; your job now is to step back and evaluate the website holistically as a set of interlocking systems and processes. Here’s where you get to be more intentional about which tool fits which project.
Clients want websites that convert at the end of the day. Easier said than done—that’s why they come to you, to demonstrate how that looks like in practice. Just keep in mind that as you’re steering these new AI tools, you have the choice to either accelerate or hit the brakes. Choose wisely, and don’t just agree to your client’s every whim.
3. Standout sites aren’t built in a day
“Vibe coding can hand you a finished site in day one, but the price is paid at around month three.”
—Rose Cawley and Hailey Benton, The future is a vibe
Vibe coding platforms can produce a finished website in a single day—within a single hour, even. Cheap and convenient in the way that fast fashion clothing is. Unfortunately, cheap and convenient don’t last for very long; both website and garment show signs of breakage in a matter of months.
If a business needs a website right here, right now, then a haphazardly generated one might suffice. Somewhat acceptable when starting out, but the structural integrity of the code could be compromised on the inside. They’re also incurring a larger technical debt in accessibility, security, and maintenance. What do they do when things fall apart? Generate yet another flimsy build?
Ideally, your client would very much prefer a robust website that lasts them years, not months. A few weeks of working with you should be worth the wait. After all, a website that a business won’t outgrow quickly requires a level of care and intentionality that artificial intelligence alone is simply not built to deliver.
4. It’s alright to start small and scrappy
“If you’re launching something and you’re not a little bit embarrassed with what you launched… you probably launched too late… I think launching early and doing small versions of iteration is the best way to launch anything, including your client’s website.”
—Nick Ippolito and Will Myers, Beyond websites
Whether you’re building for one client or many customers, as a web designer you have to be comfortable in taking action even when you don’t know everything yet. Get acclimated to wading the unknown and unfamiliar elements of the project at hand. Trust that you have the ability to figure out the work as you go, as long as have a clear direction in mind.
You’re going to learn so much more about web design and development in the act of doing things. Whenever you’re feeling lost, make sure you listen intently to feedback from real people who stand to benefit from your offerings. Talking to my clients and customers is what has taken Squarestylist to where it is today.
5. Word of mouth takes you further in AIO
“Your website is foundational, but service brands need presence everywhere… Go out there and get found.”
—Tom Smeaton, Why AI recommends some businesses—and ignores others
Apparently, there’s a subtle distinction that matters between the SEO of the past decade and the emergent AIO evolution. It pays to keep in mind that search engines operate on rankings; AI chatbots synthesize recommendations. That means the optics of brand visibility is changing in real time.
Since AI predominantly distills market signals from multiple online sources, it may no longer be enough to simply show up with content in your own corner of the internet. You also need your other past clients and connections to vouch for you loudly and consistently in public reviews, marketplaces, or forums.
Being namedropped in AI responses, then, requires a more holistic marketing and PR approach, where you carefully choose collaborations that play by your strengths and leave an impression in a way that matters.
Everything in our industry is moving so fast right now, and it’s natural to feel a little uncertain about where it’s all heading. Even so, I’m feeling optimistic about Squarespace’s direction and about web design as a whole. What excites me most is getting to say yes to projects that felt impossible just a year ago, like custom tools, interactive features, and ideas I used to set aside because they were out of reach. I hope this era of change opens up even more ways for us to reshape what it means to be a web designer and developer.
What’s one new feature you’re most excited about?