Presented by the Squarespace team

Preview new tools for professional designers and developers with Squarespace’s Product teams. During this opening presentation, Squarespace team members will share the newest releases and what we’re working on to streamline your business and help you and your clients stand out online.

Attend one of several intimate discussions led by designers and business experts from across the Circle community: 

• Designing for Impact: Building Nonprofit Websites That Work with Kaitlin Aguilar of Tenfold Creative Co. 

  • Designing for nonprofits comes with unique challenges: limited resources, complex messaging, and high expectations. This roundtable explores how to translate a nonprofit’s mission into clear, effective websites that drive engagement and donations. Come ready to share insights and strategies for purpose-driven work.

• Human by Design: Staying Original and Trusting Your Creative Instincts in the Age of AI with Clarissa Burton of Clarissa’s Creative Consulting

  • In a digital landscape increasingly shaped by AI, web designers face the challenge of staying original while navigating an influx of automated tools and trends. This conversation explores how to reclaim your creative voice, trust your design instincts, and avoid the trap of “template thinking” that makes brands feel interchangeable. Discuss how to use AI as a supportive tool without letting it replace the human insight and intuition that set your work apart.

• Close More Deals: Strategies to Overcome Objections and Increase Revenue with Stephen Palacino of Page1 Branding

  • Every client has objections during the sales process—but the key is not the objection itself, it’s how you categorize it. Is it broad and universal, or is it feelings based and personal? This roundtable focuses on spotting the difference so you can turn objections into sales.

• Brand Therapy: Identity and Clarity for the Business You’re Building with Asia David of Die Free Studios

  • Built around the Brand Therapy methodology, this roundtable explores what to do when your business no longer reflects your vision. You’ll dig into the identity, clarity, and strategic shifts required to take your business further.

• The Peanut Butter to Your Jelly: Pairing The Words That Put Your Designs to Work with Taylor de la Fuente of Bigmouth Copy

  • Great design grabs attention, but words close the deal. This roundtable unpacks why copy and design are two halves of the same experience—and how that changes the way you work. You’ll discover practical strategies for writing copy that guides visitor behavior and turns beautiful websites into ones that convert. 

• Zen and the Art of Logging Off: How to Take a Break From Your Business and Come Back Stronger with Becca Harpain of Inside The Square

  • This roundtable takes an honest look at what actually happens when you truly step back from your business: what breaks, what doesn’t, and how AI can make it possible to return with more clarity and less chaos. Share your own stories, fears, and goals for building a sustainable work life that holds up across every season.

• Mind the Gap: Connecting What You Say to What You Do with Heather Qader of The Qader Group

  • In a world of radical transparency, the distance between your marketing and your operations is where trust erodes. This roundtable takes a close look at the alignment between brand identity, public reputation, and operational reality—moving beyond logos and taglines to examine where your daily actions might be undermining your biggest ambitions.

• The Ceiling Is Internal: Why Your Business Can’t Outgrow the Self That Built It with Omari Harebin of SQSP Themes

  • Most designers assume their next breakthrough depends on better tactics, clearer positioning, or stronger marketing. The real limit is usually internal—self-trust, authority, visibility, pricing capacity, the ability to hold a larger identity. This conversation helps you recognize the internal ceiling you keep mistaking for an external problem, and why naming it is the work.

Becca Harpain, Inside The Square
Dave Hawkins, Made by Dave
Will Myers, will-myers.com

Three web professionals, three distinct approaches, and one honest conversation about what AI actually looks like in a working Squarespace practice. The session moves through real workflow territory: building proposals, auditing sites, writing custom code that respects native logic and responsive breakpoints, and talking to clients about AI without losing their trust. It builds around clear themes with enough room for the energy to stay natural. Think of it as the kind of Circle partner dialogue that usually happens off-stage.

Lunch will be provided at Squarespace HQ for all in-person Circle Day attendees.

Learn how design and technology leaders view the role of human creativity in an era of automation in a conversation with Squarespace’s Founder and CEO, Anthony Casalena.

Attend one of several intimate discussions led by designers and business experts from across the Circle community: 

• Designing for Impact: Building Nonprofit Websites That Work with Kaitlin Aguilar of Tenfold Creative Co. 

  • Designing for nonprofits comes with unique challenges: limited resources, complex messaging, and high expectations. This roundtable explores how to translate a nonprofit’s mission into clear, effective websites that drive engagement and donations. Come ready to share insights and strategies for purpose-driven work.

• Human by Design: Staying Original and Trusting Your Creative Instincts in the Age of AI with Clarissa Burton of Clarissa’s Creative Consulting

  • In a digital landscape increasingly shaped by AI, web designers face the challenge of staying original while navigating an influx of automated tools and trends. This conversation explores how to reclaim your creative voice, trust your design instincts, and avoid the trap of “template thinking” that makes brands feel interchangeable. Discuss how to use AI as a supportive tool without letting it replace the human insight and intuition that set your work apart.

• Close More Deals: Strategies to Overcome Objections and Increase Revenue with Stephen Palacino of Page1 Branding

  • Every client has objections during the sales process—but the key is not the objection itself, it’s how you categorize it. Is it broad and universal, or is it feelings based and personal? This roundtable focuses on spotting the difference so you can turn objections into sales.

• Brand Therapy: Identity and Clarity for the Business You’re Building with Asia David of Die Free Studios

  • Built around the Brand Therapy methodology, this roundtable explores what to do when your business no longer reflects your vision. You’ll dig into the identity, clarity, and strategic shifts required to take your business further.

• The Peanut Butter to Your Jelly: Pairing The Words That Put Your Designs to Work with Taylor de la Fuente of Bigmouth Copy

  • Great design grabs attention, but words close the deal. This roundtable unpacks why copy and design are two halves of the same experience—and how that changes the way you work. You’ll discover practical strategies for writing copy that guides visitor behavior and turns beautiful websites into ones that convert. 

• Zen and the Art of Logging Off: How to Take a Break From Your Business and Come Back Stronger with Becca Harpain of Inside The Square

  • This roundtable takes an honest look at what actually happens when you truly step back from your business: what breaks, what doesn’t, and how AI can make it possible to return with more clarity and less chaos. Share your own stories, fears, and goals for building a sustainable work life that holds up across every season.

• Mind the Gap: Connecting What You Say to What You Do with Heather Qader of The Qader Group

  • In a world of radical transparency, the distance between your marketing and your operations is where trust erodes. This roundtable takes a close look at the alignment between brand identity, public reputation, and operational reality—moving beyond logos and taglines to examine where your daily actions might be undermining your biggest ambitions.

• The Ceiling Is Internal: Why Your Business Can’t Outgrow the Self That Built It with Omari Harebin of SQSP Themes

  • Most designers assume their next breakthrough depends on better tactics, clearer positioning, or stronger marketing. The real limit is usually internal—self-trust, authority, visibility, pricing capacity, the ability to hold a larger identity. This conversation helps you recognize the internal ceiling you keep mistaking for an external problem, and why naming it is the work.

Nick Ippolito, SquareKicker
Will Myers, will-myers.com

Squarespace is entering a new phase. With expanding APIs and the rapid acceleration of AI-assisted development, the barrier to building products, plugins, extensions, and digital tools is lower than it’s ever been; and more people in the ecosystem will start building. The risk isn't that they won't build. It's that they'll build the wrong things. In this session, Nick Ippolito and Will Myers focus on the process behind product creation: identifying meaningful problems within the Squarespace ecosystem; determining whether an idea is worth pursuing, approaching validation before overbuilding, and understanding what it actually means to run a product business, not just launch one.

Andy J. Pizza, Author-Illustrator and Host of Creative Pep Talk

Learn how you can assert the value of your creativity to maintain your confidence in a rapidly-evolving industry with author-illustrator and host of the podcast Creative Pep Talk, Andy J. Pizza.

Enjoy refreshments, network, and reflect on the day with fellow Circle partners.