An Inside Look at Circle Day 2023: Build Your Toolkit

A presenter guiding audience members through an interactive workshop

Professional web design can be a fulfilling and rewarding career path. In addition to unleashing creativity and bringing ideas to life through stunning and functional websites, web designers have the opportunity to work with clients from various industries and expose themselves to new ideas, challenges, and experiences. Web design is always changing, keeping professionals engaged with new technologies, trends, and methodologies. 

Squarespace Circle brings the spirit of perpetual learning and skillbuilding to life through our annual Circle Day event. Boasting the theme “Build Your Toolkit,” the hybrid web design conference welcomes more than 100 Circle members in person and more than 1,000 professionals online for a day of networking and discovery on August 24, 2023. Attendees have the opportunity to participate in product deep dives, learn successful entrepreneurship practices, and develop their skills to effectively support a professional web design career on Squarespace. 

 
 

The Circle team has been hard at work planning Circle Day 2023 since the inaugural conference last year. We sat down with Sarah Greisdorf and Sam Zelitch, Circle Community Managers, to learn more about what attendees can expect from this year’s event.


Tell us why you chose “Build Your Toolkit” as the theme of Circle Day 2023. 

Sarah Greisdorf: We chose “Build Your Toolkit” as our theme because we want to gather our Circle members and help them level up their skills so they can better support their clients.

Sam Zelitch: Squarespace isn’t just websites. Most of our Circle members know this. They know that in addition to the website product, there’s ecommerce, Acuity Scheduling, Tock, Squarespace Blueprint AI, and so many other sub products that we are creating. The Circle team has a mission this year to make sure people think about Squarespace as a holistic product that can get their web presence as multifaceted as it needs to be in 2023.


What topics will be covered during the event? 

Sarah: We have a ton of great content coming to Circle Day 2023. Between ways to grow your practice and add new products and services to what you offer, to how you work with and offboard your clients, attendees are really learning how to expand their toolkits.

Sam: We have a lot of fun surprises that we can’t announce just yet, but stay tuned. 


Who is speaking at the event?

Sam: One of the things that makes Circle Day special is that it is truly a community conference. We are providing people access to our team. There are prominent members of the Squarespace staff who will be presenting, but by and large, 80% or more of the content is provided by Squarespace Circle members. This is intentional. We have amazing entrepreneurs, thinkers, and designers within our community. That’s why we do a call for speakers and request content directly from Circle members. We know the best way to make this a good experience for the community is to make it a community conference. 

Sarah: We want our community to hear from people who know this content the best, and those are the people going out and using this product every day. 

 
 


What tools or design methodologies will you highlight during Circle Day 2023?

Sam: Overall, we’ll share how to use Squarespace better. As Squarespace grows our suite of products and starts to reveal more exciting features, we understand how complex the system can become. This is positive because it offers a lot of opportunities for professionals to build their brands and increase their design capabilities, but it can also make it somewhat harder to manage. We want to introduce attendees to experts in Acuity Scheduling, coding, and more. All of these people will be at Circle Day both online and in person, and these are people who can help others increase their skills. Even a one-on-one conversation can yield valuable hacks and tips to building a career on Squarespace.

Sarah: What makes Circle Day unique is that the content is specifically concentrated on using Squarespace as a professional. We are really excited that, for a second time, we have a dedicated space to talk about our product as it can be used in the toolkits of Circle members and other web professionals. 

Sam: We won’t just be focused on Squarespace, either. Some topics people can expect to hear about will focus on the web design community and industry. There will be a variety of sessions, fireside chats, and rapid-fire talks on the web design industry, entrepreneurship, the creator community, client management, social media, pricing, business skills, and more. These are all things that contribute to making Squarespace work for professionals and their clients, and we want to make sure that content easily accessible and all in one place. 


What is the value of attending Circle Day?

Sarah: I see two main benefits. One is that everyone is looking for ways to improve their business, but it's hard to sit down and dedicate time to that. What we have put together, in partnership with our community, is a dedicated way to really supercharge your business and elevate it in one day. No matter what talk you attend, you’ll have learnings that are ultimately going to help your business, inspire something new, and give you creative ideas. It’s worth taking the day to come, invest, and sit down, because it’s going to pay dividends for weeks, months, potentially years to come.

The other is the ability to connect with people who are doing the same thing day to day or are using Squarespace or working with clients in a unique way that could, again, provide really creative, new insights. People who engage with other community members are often most successful with their businesses, because you can’t do anything in a silo. In learning, communicating, and networking with other people, the possibilities of what you’re able to take away exponentially increase.

Sam: Freelancing is a lonely business. It is a challenging business. It can be frustrating. It is so much harder if you decide to do it completely alone. What Circle Day does is show professionals all of these people in one place at one time who are trying to do a better job, and they are there to have fun. It is a fun event. People come away feeling supercharged for the remaining months of the year with friends they’ve made, business contacts that can cheerlead them. The energy you get from Circle Day motivates you to do a better job at your job.

All of the sessions I attended [at Circle Day 2022] were rich with insights and tips. Even a session topic you think you know inside and out can provide aha moments.
— Wayne Pelletier, Circle member and Circle Day 2023 speaker

How will Circle Day 2023 be different from Circle Day 2022?

Sam: We learned a lot from last year. I am so excited that the online experience is going to be such an improvement. There are so many more ways to connect with people–even if you’re not attending in person–and experience all of the fun that’s happening in person. Everything we did right last year, we’ll do it again.

Sarah: I am also excited about the improved online experience and new capabilities available. I look forward to hearing from Squarespace leadership and the executive presence. Lastly, we’ve doubled the hours of the conference by adding an exclusive Member Workshop Day–double the hours, double the fun!

 
 

How will online be different from the in-person experience?

Sam: If you can show up online, even for an hour, and then highlight some of the talks you want to watch later–everything will be recorded and available after–you’ll still get that same positive energy and networking opportunities that other people in person are going to get. You may even get more since the majority of attendees are online. If you can take some of that time to spend on a screen and engage with us, you’ll get a lot of benefit from it. 

Sarah: This year, we added in different types of content to make it possible for you to join and learn something in a short amount of time. We understand the reality of your work. For instance, you may have clients that day, so we added rapid-fire talks so you can learn a lot of information from talented, brilliant people. We also have formalized fireside chats online and in person. So whatever capacity you have to engage with, we are excited to meet you there. 

If [you’re] online, don’t worry about having to take a lot of notes if you think you’ll miss anything. Most sessions are recorded, so try to listen with the intention to pour [learnings] back into you. [Y]ou can always go back to the recording for tips and tricks to implement later.
— Brittani Millington, Circle member and Circle Day 2023 speaker

How can attendees make the most of the experience?

Sam: As an introvert, I can tell you that I get burnt out really quickly at conferences. I have to take breaks, even if I’m in person I have to take breaks and get away from everything and explore the neighborhood and see things. At a recent conference, I left and walked around looking at vintage clothing stores. On my way back, I actually ran into someone that I recognized from the conference, and this person and I just randomly sat down and chatted for two hours. This is now a friend and professional contact. To sum it up, I encourage people to take breaks, get away from the experience a bit, and come back.

Sarah: Meet as many people as possible. With that, be vulnerable and share what is and isn’t going well with your business. When we put on the facade that everything is going well, it’s hard to get the support that is actually available to you from this community-oriented conference. These people are experiencing the same things that you are, so lead with vulnerability and share what you’re going through, and you’ll find solace in community as well as new solutions. You’ll leave feeling enthused.

Be active in the chat streams and networking sessions. It’s a great way to connect through shared experiences. Smash the link to view attendee profiles and learn more about them, what they create, and who they are. There is so much talent and inspiration to find among your fellow attendees.
— Wayne Pelletier

Sam: Everyone who is presenting at Circle Day–all the names you’ll see on the website–all of them are just a private message, on social media or the Circle Forum, away. What you can do ahead of the conference is reach out and say, ‘Hey, I see we’re both going to Circle Day…’ and if they get back to you, that’s a friend and potential business contact you’ve made. That’s joy you’ll have to look forward to going to the conference and meeting up with a new friend.

Sarah: Keep track of who you talk to, follow up, and get another meeting on the calendar. Don’t let Circle Day be the start and end of meeting someone. This is your opportunity to grow your Squarespace network. 

[I]f it’s anything like last year, I’m looking forward to seeing people I meet in the [Circle] Forum in person. We are all over the world, so it’s great to have this space to meet in person [while] learning something new from the sessions that I can incorporate for myself and my business.
— Brittani Millington

What are you most looking forward to?

Sarah: I just adore meeting our community in person. We have folks coming who we’ve only ever spoken to online. In the way Sam described the energy our community gets leaving the conference, I feel the same. We work for a year to put on this conference, and this is such an energizing way to understand what our community needs and how we can better serve them.

Sam: I’m looking forward to transforming the in-person space. We are working with such a fantastic creative team this year that has developed a number of awesome designs to take this office we come into every day and transform it into a wonderland of color and shapes and designs. They’ve also done stuff to develop the online experience so it matches the in-person experience. 

 
 

Want more?

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


Arianna Frederick

Arianna Frederick is a content associate at Squarespace. In addition to managing the Circle blog, she develops top-of-funnel content for creative professionals and Circle members.

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