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Attending Squarespace Circle Day 2023: KSD takeaways

Attending Squarespace Circle 2023, in New York City, was nothing short of incredible.

Breaky with the Squarespace International team, a Member Workshop day, the main event - Squarespace Circle Day 2023, the atmosphere, the learnings, but more importantly, the people!…

In this blog post, I share the amazing experience and takeaways from attending the annual Squarespace Circle event 2023 in person, in New York City!


Although Squarespace Circle Day is only a single day organised by Squarespace themselves, there were also additional “events” put together to support the main day.

Tuesday 22nd August 2023: Happy Hour on the Arlo Rooftop

Organised by Squarespace Experts Jen Maher and Dreyah Bohlen and the Squarekicker Team, the perfect start to the Squarespace Circle Day was the Happy Hour meet-up at the Arlo Hotel rooftop bar. 

Having spoken to many of the attendees online it was such a lovely event, despite my late arrival due to my flight getting into JKF one hour before the scheduled meet up time. 

Was brilliant to meet… The Squarekicker Team (Nick and Hannah Ippolito), Jen Maher, Dreyah Bohlen, Christy Price, Promise Tangeman (from GoLive), Will Myers, Lorena, and so many more “Squarespacers”.

Definitely set the mood for the following days….

Wednesday 23rd August 2023:
Breaky with the Squarespace International team and the Member Workshop day

Breaky with the Squarespace International team

On Wednesday 23rd, the day before the big event, I was invited to join other Squarespace business owners (from all over the globe) to meet the international Squarespace team and have breakfast with them at the Squarespace HQ office.

We got an insider sneak peek into what’s coming soon and managed to share our insights on how we find Squarespace's international efforts in improving the platform.

Was brilliant to speak with the guys behind the scenes that make the CMS so amazing. 

Member Workshop day

The afternoon was spent mingling and meeting so many other Squarespace users where we worked together in a team of 4 to learn first-hand about the new Squarespace Courses product offering.

As a team, we are tasked with allocating each member to a “role” - The client (Wayne Pelletier), the videographer (Jay Muhlin), the marketeer (Kelsey Gilbert-Kreiling), and the website builder (Me).  We then had to create a fictitious course, create the content and film the videos, build a dummy site and then present our offering to the rest of the groups.

Gaining hands-on experience using the new Squarespace Courses feature was brilliant. In a fast-paced environment, where teamwork and collaboration are key, just like in a real-world project with a client, it was so straightforward to be able to create a Course and publish it quickly. Obviously, credit also goes not just our collaboration efforts, but aslo to Squarespace for making the new product super simple, intuitive and smooth.

At the end of the Member Workshop Day was Happy Hour, hosted by Squarespace, again more mingling and meeting amazing people!

An incredible second day making friends, and connections and learning all the good stuff about Squarespace Courses.

Wednesday 24th August 2023: Squarespace Circle Day 2023

The big day! The main event! The theme for this year's event was “Build Your Toolkit” and with so many brilliant workshops, talks and sessions it was difficult to choose which one to attend!

On my list were:

  1. Monetizing Memberships with Squarespace

  2. Empower Your Clients with E-commerce Essentials

  3. Circle Live with Squarespace CEO and Founder, Anthony Casalena

  4. Template Sellers Tell All

  5. Stop Trading Time for Money

  6. Is Social Media Really Worth It? / It's Not Hard to Say Goodbye: Crafting Client Offboarding

  7. On Creativity: A Conversation with Squarespace's Chief Creative Officer, David Lee

All the sessions were brilliant, with everyone at different stages in their Squarespace journey, there is always something to learn. 

My 5 main takeaways from this year’s Squarespace Circle Day:

  1. From Kristine Nells session (Empower Your Clients with E-commerce Essentials), she shared some real gold nuggets.  The main one is to create and share a bespoke CSV file for your e-commerce clients.  It takes hardly any time and really helps to speed up the process

  2. From Wayne Pelletier session (Stop Trading Time for Money), creating lifetime value and create systems to help you create consistency by productising your services 

  3. From the “Template sellers tell all” session, with The Squarekicker Team - Nick and Hannah Ippolito - Monica Kovach (Hold Space Creative) and Promise Tangeman (GoLive):  Don’t overthink starting a template shop - just do it, start with 2 templates, test and refine, make the templates industry-specific and niche your offering

  4. From “Circle Live with Squarespace CEO and Founder, Anthony Casalena”.  Listening, being humble and being able to switch direction are all key attributes of a successful business

  5. The people - Meeting people in real life and being able to build on from online connections is second to none.  Some of the business owners that I’ve learnt from over the years were so giving in their business advice and were actually “so normal” (shout out to Becca from Inside the Square) that it made me realise the Squarespace Circle Community is definitely special.

Squarespace Circle Day 2024

It’s safe to say that Squarespace Circle Day is going to be an event that I plan to attend every year.  There are so many great things to learn and share that the investment in attending it truly worth it.

Will I see you at Squarespace Circle Day 2024? 


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