Squarespace Circle Day 2026: My takeaways as a brand strategist and website designer.
I've been part of the Squarespace Circle community for almost a decade, and I've watched the platform, the industry and my own business evolve considerably in that time.
As the founder of The Forest, a brand strategy and Squarespace website design studio based in Ireland, I've built my business around a fairly simple belief: a website should do so much more than just look good. It should help a business communicate its value, attract the right customers and ultimately grow.
So when I tuned into Squarespace Circle Day 2026, I was particularly interested in what the latest developments would mean for the way we work, the businesses we support and the future of website design. And there was plenty to take in. From new design capabilities and business integrations to the introduction of Forma, Squarespace's next-generation AI-native creative platform, it was clear that we're entering a very different chapter in website design.
But interestingly, my biggest takeaway wasn't about technology at all. It was that as the tools become more powerful and accessible, the value of human experience, creativity and strategic thinking becomes even more important.
A different kind of Circle Day
I've been lucky enough to attend Circle Day in New York in person on several occasions, (and even opened the event after the CEO's address in 2024 with a talk on the power of email marketing). It's always a highlight of our year here at The Forest.
Teresanne O’Reilly, on stage at Circle Day 2024
There's something special about getting a room full of creative people together who use the same platform but approach their work in completely different ways. As was mentioned in the room at Circle Day 2026, 'give a thousand designers the same tools and you'll get a thousand different results'. That's one of the things I love most about this industry.
This year, because of other commitments we had with The Forest, I wasn't able to make the trip stateside for Circle Day, so instead we joined virtually from Ireland. Puno, from ilovecreatives, brought her usual brilliant energy as MC, and having experienced the atmosphere in New York before, I could immediately imagine how much fun everyone was having in the room.
The online programme also offered some worthwhile sessions specifically for those of us joining remotely. I particularly enjoyed Nicole Martinez's presentation on the role of strategy in website design, along with the human-first approach to creativity and AI explored by Hailey and Rose from The Creatives in New Zealand.
And, as always, it was refreshing to hear my fellow Circle pals like Will Myers, Dave Hawkins of Made by Dave and Becca from Inside the Square speaking candidly about the opportunities and challenges facing designers.
Will Myers, Becca Harpain from Inside the Square and Dave Hawkins of MadeByDave on stage at Squarespace Circle Day 2026
What struck me throughout the day was how much the conversation has shifted. We're no longer simply talking about how to build better websites. We're talking about how websites connect to marketing, sales, customer relationships, business operations and increasingly, AI-powered tools. For those of us running design studios, that's a significant change.
AI can help us build faster. But are we building the right thing?
One of my favourite sessions of the day came from Nicole Martinez, whose approach to website strategy was familiar to us at The Forest. She made a point that I think every website designer and business owner should consider:
The website a client asks for isn't always the solution to the problem they're actually having.
A business owner might come to us because their website feels dated, isn't generating enough enquiries or no longer reflects the quality of their work. Naturally, they assume they need a new website. And sometimes they do. But quite often, the underlying issue is much bigger.
Perhaps they're struggling to explain what makes their business different. Perhaps their services aren't clearly positioned, or they're attracting the wrong customers. Perhaps they have plenty of website traffic but no clear process for turning that interest into enquiries or sales. These are business and marketing challenges, not website design problems. But they are problems we can help them solve, nonetheless.
Before we begin designing a website at The Forest, we spend time understanding the business behind it:
Who are we trying to attract?
What do those people already know about the business?
What might make them hesitate to enquire?
What happens after someone fills in a contact form?
And, importantly, what does the business actually need the website to achieve?
Sometimes, the business owner doesn't immediately know the answers. That's where the value of working with an experienced strategist comes in.
AI can generate a website remarkably fast. It can write copy, suggest layouts, create imagery and increasingly build sophisticated functionality. But it still depends on the direction it's given. If you don't fully understand your positioning, your audience or your customers' needs, how do you know what to ask it to create?
A website can look completely finished while still missing the point.
For me, the real opportunity with AI isn't to remove the thinking from website design. It's to make the building process more efficient so we have more time to focus on the thinking that matters.
The website is only one part of the bigger picture
Another idea that stayed with me was the importance of understanding where a website sits within a business's wider marketing activity. Business owners often expect websites to do an enormous amount of work on their own. But a website doesn't automatically bring its own visitors.
People arrive through search engines, social media, referrals, press coverage, advertising, events and all sorts of other interactions with a brand. And what happens once they arrive matters just as much.
Does the website communicate the business' offerings clearly?
Does it build trust?
Does it answer the questions people have before they're ready to buy?
Is there an obvious next step?
And what happens after someone takes that step?
If a potential customer submits an enquiry and nobody follows up promptly, even the most beautifully designed website can only do so much. This is something I want to continue bringing into our client conversations.
We already approach every website project strategically, and thankfully, Circle Day reinforced the importance of looking beyond the website itself and understanding how it contributes to the business as a whole.
Every website is a marketing decision, and every page should have a reason to exist.
Squarespace is becoming a much bigger business platform
Of course, Circle Day also brought plenty of exciting product announcements.
I've always appreciated Squarespace for the balance it strikes between creative flexibility and ease of use. We build exclusively on Squarespace at The Forest, and one of the biggest reasons is that our clients can confidently manage their websites after launch. They don't need to come back to us every time they want to update a photograph, change a sentence or publish a blog post. That independence is really valuable, particularly for busy business owners (and for those who don't want to get an invoice every time they need to update their site).
So, I was relieved to see there's continued investment in the existing website-building experience alongside the more ambitious tech announcements. The improvements to Stacks, for example, open up additional design possibilities through more control over backgrounds, spacing and clickable elements. The ability to lock blocks while designing is another welcome addition, particularly when working with layered layouts.
And autosave? Hallelujah! As someone who has spent years designing websites and regularly gets into a flow when designing (and sometimes forgetting to click save as I go), I can safely say that's a feature many of us will be very happy to have!
I'm also really interested in the developments around image editing and AI-assisted imagery. Not every client arrives with a library of beautiful professional photographs. Being able to refine imagery and create a more consistent visual style within the platform could be particularly useful for smaller businesses working with limited resources.
Beyond design, the developments around customer profiles, SMS marketing, integrations and APIs point towards something bigger, which is right up our street. Squarespace just proved it is continuing to evolve from a website-building platform into a more connected environment for running a business online. That has interesting implications for our clients, but also for the services we may be able to offer as designers and strategists.
And then there was Forma
One of the biggest announcements of the day was Forma, Squarespace's new AI-native creative environment. Forma represents a different approach to building digital experiences. Rather than working exclusively within the familiar website editor, the idea is to use prompts and a more flexible creative workspace to develop websites, applications, agents and other business tools. It's an exciting prospect.
As someone who works with businesses across different industries, I can immediately see the potential for creating more bespoke functionality without every project requiring a traditional custom development process.
There are also opportunities to improve the way we work internally. If new tools can help us make website updates faster, understand website data more easily or automate repetitive tasks, that frees up time for the strategic and creative work our clients really value. But I'm also approaching Forma with a healthy dose of curiosity.
One of the reasons we've built The Forest around Squarespace 7.1 is the client experience after launch. We want our clients to feel confident managing their websites. We don't want them to be dependent on a designer or developer for every small change. So as we explore Forma, one of my biggest questions will be how that client independence translates into this new environment.
I appreciated that Squarespace CEO Anthony Casalena acknowledged during the event that Forma is still evolving and that aspects of the experience, including client handover, will be refined as us Circle members begin using it. I think that's a sensible approach. New technology doesn't need to be perfect on day one, but it does need to be tested in the context of real businesses and real users. For now, I'm excited to explore what's possible, while remaining mindful that just because we can build something doesn't necessarily mean we should.
The question will always be whether it genuinely improves the experience or outcomes for our clients.
What AI search means for the businesses we work with
Another particularly relevant conversation was around the way AI is changing online discovery. For years, businesses have focused heavily on SEO (search engine optimisation), and understandably so. But we're increasingly moving into a world where people aren't simply searching for businesses online. They're asking AI tools to recommend them, compare them and help make decisions. That creates a different challenge.
Having a website with a few well-optimised service pages may not be enough to communicate the full value of a business anymore. Clear positioning, useful content, specific expertise, real examples and credibility across different online channels are becoming increasingly important.
Your website should be a reliable source of information about your business, but it shouldn't be the only place your business is represented.
Articles, industry directories, relevant press coverage, social media and genuine participation in your professional community all help build a more complete picture of who you are and what you do. This is an area I'm particularly interested in exploring further at The Forest.
We've always placed a strong emphasis on clear messaging and brand positioning, but the evolution of AI search gives businesses another reason to take that work seriously. If you struggle to explain what makes your business different, it's hard to expect a search engine or AI assistant to understand it either.
And while nobody can guarantee how an AI platform will recommend a particular business, we can help clients create clearer, more useful and more credible information about what they offer.
A reminder that launching matters too
One of the more practical conversations from the day was about launching projects before every last detail feels perfect. That's something I struggle with in life in general, never mind in business. But it also reminded me of a client experience that's stayed with me recently.
In February 2025, we built an e-commerce website-in-a-day for a gifting business. The website was ready, the products were receiving a great response at in-person events, and the foundations were there to begin selling online. But the business owner was nervous about taking the leap. They've been open about that hesitation, and despite having a website ready to go, the business has remained unlaunched online. As a result, they've missed important seasonal selling opportunities, including two Christmas gifting periods.
I share that example without judgement, (as I mentioned above, I’ve also held back on launches) because launching a business can feel like an enormous step, particularly when you've invested so much of yourself into it.
But it illustrates something important. A website can't start doing its job until it's live.
And sometimes, the most valuable advice we can give a client isn't about design at all. It's helping them recognise when something is ready, encouraging them to take the next step and reminding them that a website can (and should) continue to evolve after launch. That's another reason I value the human side of this work.
We're not just building websites. We're helping people make strategic decisions about their businesses.
What I'm taking back to The Forest
My original intention in attending Circle Day was to come away with ideas I could actually apply, rather than a list of exciting announcements. And there are a few ideas I'm particularly keen to explore.
First, we'll be testing the new tools.
We'll start by experimenting with the latest Squarespace features on our own websites, including TheForest.ie and TheBrandClarityCoach.com.
We'll also explore opportunities with a small number of existing clients who enjoy trying new technology and are open to experimenting with functionality that could improve their businesses. I think it's important to understand how these tools work in practice before making them part of our standard client offering.
Second, I'll be placing even more emphasis on strategy.
Not every business needs an extensive brand strategy project, and not every business has the budget for one. But every business benefits from strategic thinking.
Sometimes that means a comprehensive review of positioning, audience, messaging and direction. Other times, it's a focused website strategy session that helps us clarify the essentials before we begin designing. The depth of the work may vary, but the principle remains the same. We need to understand what we're trying to achieve before deciding what to build.
Third, we'll be developing a clearer approach to AI search and online visibility.
I want to explore how we can help clients create websites and content that communicate their expertise effectively, both to the people visiting their websites and to the technologies increasingly influencing how those people discover businesses.
And finally, I'll be looking at how these developments can improve our own processes.
As The Forest continues to grow, I'm interested in ways to work more efficiently without compromising the personal attention and quality of thinking that our clients come to us for. If technology can help us spend less time on repetitive tasks and more time solving meaningful business problems, that's a development worth embracing.
The future is exciting. And it's still human.
I finished Circle Day feeling genuinely excited about what lies ahead. The pace of change is extraordinary, and I think we're only beginning to understand what's going to be possible over the next few years. There will undoubtedly be challenges, plenty of experimentation and probably a few things that don't work quite as expected along the way. But that's part of working in a creative, technology-driven industry. We've always had to learn, adapt and evolve.
Christy Price, fellow Squarespace Circle member, engaging in a live Q&A at Circle Day 2026
What hasn't changed is the importance of understanding the people and businesses we're designing for. AI can help us build faster. New platforms can give us more creative freedom. Better integrations can make websites more useful and connected. But none of those things removes the need to ask good questions, understand a business's customers, recognise opportunities and make thoughtful decisions. If anything, I think they make those skills more valuable.
The future of website design isn't simply about what we can build. It's about knowing what is worth building, and why.
And that's what I'll be taking back to The Forest.
Sponsored content disclosure: This article was created in paid partnership with Squarespace. All opinions, observations and reflections are my own, based on my experience attending Squarespace Circle Day 2026.
The Forest is an Ireland-based brand strategy and Squarespace website design studio, led by founder Teresanne O'Reilly. We create refined, strategy-first websites for businesses that want to communicate their value clearly, attract better clients and grow.
Get in touch about our website design and brand strategy services at TheForest.ie.
