The Designer Retreat is a focused, intensive weekend of business mentorship and peer-to-peer group coaching. Led by some of the top minds in the Squarespace community, The Designer Retreat goes beyond a digital course to bring personal insight into your specific business needs. SPACE IS LIMITED TO ONLY 24 ATTENDEES. Attendees will submit their unique business challenges to our expert panel and learn how they would respond.

The Designer Retreat is crafted towards seasoned web professionals looking to make a shift in their design business or advance their careers. This isn’t a fast track towards increased revenue, but rather a transparent and holistic approach towards business coaching that brings decades of real-world success into your unique business challenges.

A lot!

This event is different than others you may have attended. Rather than providing a one-way presentation or solicitation, our goal is to actively engage with business owners. We will provide a pre-event questionnaire for you to provide background into your business, share current pain points, and submit your own business challenges to the speaker panel. Then at the event, our panel will be prepared to provide insight into your specific, real-time challenges. We’ll then workshop our business needs with speaker-led small groups and Q&A.

Additionally, our goal is to share from experience, so there will specific instruction on the strategies used by each speaker to grow their revenue and position themselves as the expert for their audience.

This isn’t about insider secrets or formulas for growth, but about sharing the tools, knowledge, and processes that have made each speaker confident and profitable.

Though the content as a whole will focus on thought processes, pricing models, design techniques, and client management, we’ll be looking at all of these through a lens that is unique to Squarespace designers.

The Designer Retreat will kick off at 6pm March 23, 2026, and end at 9pm on March 24.

Ticket prices are $1995 per person or 3 installments of $699. Ticket spots are intentionally capped to keep the experience personal and hands-on.

4 meals are included with your ticket: the kickoff dinner, continental breakfast and lunch at The Rutledge Room, and a reception dinner to cap off the event. Prior to the event, we will send out a meal checklist to accommodate any dietary restrictions.

In order to keep the event as accessible as possible, we opted to not increase the cost by including lodging. This gives attendees the freedom to choose the best lodging for their needs.

Absolutely!

Most pro Squarespace designers charge between $3k-$15k for new websites. This means that after securing only one new client or project from a lesson learned at this event, the event has paid for itself. Our speaker panel brings decades (some multiple decades) of marketing and design experience with full pipelines and a desire to help others succeed.

Plus, you’ll have the added benefit of being with other like-minded individuals to level up your skills, understand new initiatives, and be better equipped to grow your business.

We love digital courses! And many of our speakers have successful digital course offerings. You may have taken a course or two! But after talking with other designers in the industry, we felt there was a deep, unmet need for intimate, individualized coaching that can only come from an in-person event. Rather than structure the event for hundreds, 24 attendees allows time for successful breakout sessions, as well as tailored advice and insight into your specific business from our speaker panel.

Charleston is a walkable city, though a taxi may be needed and/or required depending on where you stay. Most short rides in the city are usually $7-$15. There are a number of hotels and boutique inns throughout Charleston and close to our home-base, The Rutledge Room, including several within a 10 minute walk along King Street. In order to keep the overall cost down, lodging is not included to allow each attendee the freedom to choose what will best fit their individual need and budget.

Options within walking distance to The Rutledge Room (207 Rutledge Ave):

• The Ashley (4 min walk) use code “welcome5” for 5% off your stay

• Hyatt Place on King Street (11 min walk)

• Hyatt House on King Street (11 min walk)

• Curated Vacation Properties (multiple homes, great for groups) use code “welcome5” for 5% off your stay