Schedule & Event Details
NYC Schedule
All times are displayed in Eastern Time.
8:30 AM: Check-in opens
9:30 AM: Introduction from Puno of ilovecreatives and ilovecreatives Studio
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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.
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Becca Harpain, Inside The Square
Dave Hawkins, Made by Dave
Will Myers, will-myers.comThree 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.
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Lunch will be provided at Squarespace HQ for all in-person Circle Day attendees.
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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.
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Nick Ippolito, SquareKicker
Will Myers, will-myers.comSquarespace 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.
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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.
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Enjoy refreshments, network, and reflect on the day with fellow Circle partners.
Live Stream Schedule
All times are displayed in Eastern Time.
8:30 AM: Live stream and chat open
9:30 AM: Introduction from Puno of ilovecreatives and ilovecreatives Studio
-
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. -
Nicole Martinez, n/volve collective
Many designers obsess over how a website looks, but fewer think about how it functions in their client's larger marketing plan. In this session, Nicole Martinez shares how to position your website as an active marketing asset that works in tandem with your brand, content strategy, and client journey. Walk away with a new framework for approaching every site build as a marketing strategy decision, not just a design project.
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Tom Smeaton, Squarespace
Service-based businesses—entrepreneurs that sell their time, their expertise, and their services rather than physical goods—are often overlooked in the ecommerce SEO world. Join Squarespace’s SEO Manager, Tom Smeaton, for an overview of a recent study on 1.2 million AI search citations to learn what makes a service-based business model show up in AI search and how you can improve your clients’ SEO and AI search strategy.
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Becca Harpain, Inside The Square
Dave Hawkins, Made by Dave
Will Myers, will-myers.comThree 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.
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Alex Chimilio, Weatherproof® Vintage
Serra Semi, LumensLennon and McCartney, The Eames, The White Stripes, Prada and Simons—creative history is full of partnerships. Behind every successful duo is a balance of shared vision, creative tension, and real structure. Drawing on their own experience as collaborators, Serra Semi and Alex Chimilio offer a candid look at what makes a creative partnership work, from navigating friendship and defining roles to maintaining momentum when the pressure builds.
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Victoria Banuelos, PUESTO
Most designers build their client's site, hand over the login, and move on. But the handoff is one of the most overlooked opportunities in your client relationship. Victoria Banuelos explains how to structure a client training that builds confidence without scope creeping your time, and why teaching (not selling) might be your most effective growth strategy.
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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.
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Michael Fine, Studio Fine
In high-stakes work, design decisions shape more than how something looks; they influence whether people trust it, fund it, or act on it. Michael Fine draws on real projects that helped teams raise millions in funding to break down how brand, messaging, and execution drive credibility and clarity. You'll leave with a clearer sense of how to make and defend design decisions when the stakes are real.
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Hailey Benton and Rose Cawley, The Creatives
Before "vibe coding" had a name, Hailey Benton and Rose Cawley were already living the philosophy—building bold, high-performing websites for real businesses without a developer in sight. In this session, The Creatives co-founders come with a fresh take on the no-code movement, unpacking how to harness these tools without losing your creative edge and how to confidently position no-code as a premium, high-value offering your clients will actually pay for.
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Nick Ippolito, SquareKicker
Will Myers, will-myers.comSquarespace 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.
FAQs
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The in-person Circle Day experience will take place on Wednesday, October 21, inside Squarespace’s New York City headquarters at 8 Clarkson Street.
Check-in will open at 8:30 AM and Circle Day events will begin at 9:30 AM. The final presentation will end at 5:30 PM, immediately followed by a happy hour. Breakfast, lunch, and light snacks will be provided.
The New York City experience is sold out. Register for the online live stream to watch events from Squarespace HQ.
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Circle Day keynote presentations will be live streamed on YouTube on Wednesday, October 21. In addition to the sessions at Squarespace HQ, online attendees can also view online-exclusive sessions and join a real-time chat to connect with other attendees.
The live stream will begin at 9:30 AM and end at 5:30 PM. The live stream link will be shared via email and available on the Squarespace Circle YouTube page.
Register for free to join the Circle Day Live Stream.
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See the full list of speakers presenting at Circle Day 2026.
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Circle Day attendees can enjoy discounted rates near Squarespace HQ at the Arlo SoHo and Hotel Hugo. The discount codes are automatically applied using the links below:
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Our New York City headquarters is located at 8 Clarkson Street between Varick and Hudson Streets.
The entrance to 8 Clarkson is located next to Shake Shack and across from James J. Walker Park.
The closest subway stops are Houston Street (1), West 4th Street (A, C, E, B, D, F, M).
Parking is located nearby at Icon Parking or Minetta Garage.
Squarespace will not provide reimbursement for travel or parking.
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The entrance to Squarespace HQ is on ground level with a ramp to the building's elevators.
Circle Day will take place on the 12th floor, and pre-Circle Day events will take place on the 6th floor. Both floors are accessible via elevator and have ramps throughout to access elevated areas. There will be a dedicated elevator just for Circle Day attendees.
Squarespace employees will be available to answer questions or help you in person at a Q&A desk located on the 12th floor.
Restrooms throughout the building are accessible, with both single-stall and multiple-stall restrooms. Gender diversity is welcome at Squarespace, and guests can use whichever restroom they find most comfortable.
Lunch and snacks will be provided for attendees for Circle Day. Dietary restrictions included with registration will be accommodated.
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Both virtual and in-person attendees can connect with the Squarespace team on YouTube during the event for technical support or other questions.
Recordings of Circle Day events will be available after the conference.
If you need any assistance or accommodation, please email circleday@squarespace.com.
Technical Help
If you experience technical difficulties during the event, complete the form below and our team will help you as soon as possible.