Since 2022, Squarespace’s Circle Day has celebrated the Circle community, which is made up of more than 100,000 designers, entrepreneurs, and creators who are passionate about helping clients evolve their businesses online. On September 18, 2024, the community gathered online and in person at Squarespace’s office in New York City to watch fellow members and Squarespace leadership deliver talks about design, content marketing, ecommerce, business, and more. 

The event’s theme, “Power Up,” was on full display during a conversation with Squarespace Founder and CEO, Anthony Casalena, and Paul Gubbay, Chief Product Officer. This highly anticipated follow-up to 2023’s interview with Anthony offered attendees a deep dive into the past, present, and future of Squarespace, as well as answers to their burning questions about the platform.

Unlocking entrepreneurial potential with Squarespace Refresh

Squarespace Refresh 2024 was top of mind during Circle Day, as Paul gave Circle members an early look at platform innovations that herald a new era for entrepreneurs. From evolutions in how customers deploy and manage content and memberships to SOC 2 Type II certification compliance updates to advanced ecommerce features like Client Invoicing, Squarespace Payments, and donation management tools, these entrepreneurial solutions empower you to help take your clients’ ventures to the next level.

“We’ve spent a lot of time trying to answer questions like, when customers visit [squarespace.com], how do they witness the Squarespace platform, sign up for it, see what’s in the manager, and buy it?” Anthony said. “Do the plans available to each customer make sense for their business? Is everything properly integrated with ecommerce? We constantly considered these sorts of ideas while working toward Refresh 2024, ensuring that all of its features work together in the most coherent way.”

Just as important to Anthony and Paul as delivering innovations is refining—or rather, refreshing—existing Squarespace features for design, ecommerce, scheduling, and more. The two remarked how adhering to this approach to Refresh poses a win-win to Squarespace customers, affording you and your clients new platform functionality and tangible speed and responsiveness improvements for features already indispensable to your workflows.

Anthony highlighted how Squarespace teams are careful not to require you engage with new Refresh features that, while useful in many cases, may not match your particular business. For example, if a nonprofit primarily uses its Squarespace website to accept donations, it can hide ecommerce features like product sales or blog monetization from its website management interface to create a more bespoke workflow tailored to its exact needs.

Supporting—never replacing—creativity with AI

From day one, Anthony’s philosophy for Squarespace has been simple: to amplify customers’ creativity by arming them with intuitive tools for crafting stunning, memorable websites and digital brand presences. This belief has guided everything Squarespace has accomplished over the last 20+ years, and now extends to the company’s artificial intelligence (AI) approach.

Anthony noted how Squarespace’s recent AI-powered Design Intelligence features, like one-click Site Themes, AI-generated client documents and descriptions for SEO, videos, and courses “empower you to focus more on high-level creative solutions for people over more granular site design minutia or bug fixes.” He highlighted how Squarespace AI can generate imagery inspired by expert-curated visuals to match the customer’s prompt. The images also blend seamlessly with sitewide color-scheming, foreground text, and other site elements.

“There's a curation aspect to everything we do with AI, based on our years of experience, that makes things faster and easier for customers out the gate, without replacing the creative things they do with the platform,” said Paul. Jumping off that, Anthony remarked that while Squarespace invested in tech innovations like AI and machine learning (ML) from an early stage, Squarespace teams are careful to incorporate such new technologies to benefit customers’ workflows, rather than for the sake of adhering the platform to trends.

Emphasizing customer service every step of the way

In 2023, Squarespace acquired all domain registrations and associated customer accounts from Google Domains. By July 2024, Squarespace completed the migration of roughly 10 million domains to Squarespace Domains, all the while working to ensure incoming customers would enjoy near-feature parity with Google Domains.

Anthony addressed a Circle member’s question regarding the steps Squarespace is taking to address the obstacles some customers have faced when contacting Squarespace Customer Support to resolve their migration-related technical difficulties.

“Squarespace has always been responsible for domains, but never before in this form,” said Anthony. “We now have specialized customer service groups actively tackling migration-related issues such as new forms of fraud and DNS problems.” In addition, Anthony, Paul, other Squarespace leaders, and Squarespace Customer Support perform weekly support ticket reviews to understand and promptly address emerging issues, including outages, queue health, and live chat wait times. Anthony believes these steps will elevate Squarespace Customer Support’s quality beyond pre-migration levels and enable customers to more quickly request and receive platform support.

Continuing ‌community collaboration

Squarespace customers are and always have been at the heart of everything Squarespace does. Anthony notes how Circle member feedback and sentiment will continue to play a key role in shaping the platform’s future. This devotion to community collaboration aligns with another core principle that’s guided Squarespace leadership since the platform’s inception: design is not a luxury. Web designers should feel empowered to harness boundless imagination and creativity to craft incredible, head-turning websites for clients.

When asked what he’s looking to see from the Circle community in the next year, Anthony challenged members to draw bigger clients than ever before to the Squarespace platform. In turn, he promised Squarespace will continue supporting Circle members by delivering valuable new features and updates to build Squarespace sites to a level of quality you may have never thought possible.

Anthony and Paul closed their conversation with a heartfelt appreciation for the Circle community. “You could pick any number of design companies to work with, and at the end of the day, it’s your livelihood. So the fact you continue to invest and believe in Squarespace is really gratifying.”

Want more?

Check out Squarespace Circle, Squarespace’s program for professional designers. Along with exclusive content, discounts, and other perks, Circle brings professionals together from across the globe to exchange advice while connecting with new clients and collaborators.