Kelsey Gilbert-Kreiling on Building Collaborative Design Agencies
In this episode of Looks Good From Here we sit down for an inspiring conversation with Kelsey Gilbert-Kreiling, co-founder of Week at the Website and author of "Squarespace from Sign Up to Launch." Watch the video or continue reading below.
Building a successful web design business takes more than technical skills—it requires strategic thinking, team building, and the courage to evolve beyond client work. Kelsey Gilbert-Kreiling, co-founder of Week of the Website and one of Inc. Magazine's Female Founders 500, has spent over a decade mastering this balance while creating a thriving agency that serves clients across industries.
Starting a Web Design Business Without a Traditional Path
Kelsey's path to web design started in an unexpected place: fashion design school. While studying at what she describes as "Project Runway School," she launched an online fashion publication, teaching herself to build websites out of necessity rather than formal training.
"I started an online fashion publication and was kind of bouncing between New York and Chicago covering different fashion events because I just liked it," Kelsey explains. "No one told me I couldn't."
This creative foundation proved valuable when she transitioned from fashion to food journalism, eventually building websites for a hospitality group. Her first site? Built on Tumblr because of budget constraints. But when she needed more design functionality, she discovered Squarespace—and everything changed.
The turning point came when a friend from another restaurant group needed website help. Kelsey and her future business partner, Mallerie, decided to pitch the project "just for practice." They won the job, received their first check before opening a bank account, and suddenly found themselves running an agency.
"We had a check before we had a bank account," Kelsey recalls. "It was one of those like, 'Oh, well, we really caught the car on that one, didn't we?' I guess we're in business."
Building a Sustainable Web Design Agency
Week of the Website has grown significantly since that first accidental project, now operating with a team of developers, project managers, and fractional leadership support. The company offers one-week, two-week, and four-week website projects, maintaining their signature quick turnaround while delivering high-quality results.
Kelsey emphasizes that scaling requires intentional choices about where you spend your time. "There's no business to take on work for nonprofits you feel passionately about. There's no job for our devs. There's no work for our PMs if I don't keep pushing on those things that are like less directly connected to the client experience," she explains.
For designers considering the leap from freelance to agency, Kelsey offers honest advice: "If you want to build a business, it's just a different thing than working for yourself. And I mean that from the turning point of having employees and having people that work with you."
The transition means accepting that your role will shift from hands-on design work to business development, team management, and strategic planning. It's a bittersweet realization, but one that creates space for growth.
Creating a Positive Company Culture for Remote Teams
One of Week of the Website's most notable achievements isn't visible in their portfolio—it's the culture they've built. Inc. Magazine recognized them as "wellness warriors" for their approach to team wellbeing, something Kelsey considers more meaningful than any project accolade.
"If I do nothing else in this world, that's the thing I feel like I'm the most proud of for our company," Kelsey shares. "I continue to be in awe of the people that we work with."
This culture stems from honest communication and flexibility. When team members need to attend their child's school event or handle personal matters, the answer is yes. When business is slow, Kelsey communicates openly with her team so they understand the situation.
"We've tried the hardest to develop a culture of honesty," she explains. "When we go through slower times, we want to communicate that to our team so that they feel like we understand that they are people working a job for a reason."
For designers building teams, this approach creates a two-way street of trust. When you're transparent with your team, they'll be honest about project challenges, client issues, and workload concerns—feedback that becomes essential as you step away from day-to-day client work.
Managing Work-Life Balance as a Design Business Owner
The balance between working in your business versus working on your business becomes increasingly critical as you scale. Kelsey discovered this the hard way after having her son, when she realized she couldn't maintain the intense pace of their five-day projects while managing new parenting responsibilities.
"When I came back, I realized I can't do the cadence of our five-day projects. I'm pumping. I don't have a nanny yet. It's not going to work," she recalls. The company had to completely restructure their model—a challenging transition that ultimately led to bringing on additional designers and team members.
One strategy that's helped Kelsey maintain boundaries is implementing structured meeting schedules based on the Entrepreneurial Operating System from the book "Traction".
"Every Tuesday I show up knowing that I'm going to have three meetings back to back to back and I know exactly what's going to happen in those meetings," she explains. "I think that's the other thing for creatives that become entrepreneurs—embracing the moments where structure frees you."
“I think that’s the other thing for creatives that become entrepreneurs—embracing the moments where structure frees you”
Writing a Book on Squarespace While Running an Agency
As if running a growing agency weren't enough, Kelsey also wrote "Squarespace: From Sign-Up to Launch"—a comprehensive guide for building websites on the platform. The opportunity came through an unexpected LinkedIn message from a technical publisher.
"I definitely thought it was spam 100%," Kelsey admits. "But it did enough to catch my attention that I did some research and looked around and I was like, 'Oh, no. This is like a legitimate technical publisher.'"
Her operations manager gave her crucial advice: if she was going to write a book, do it while her son was still young. "He's still kind of in that potatoey phase," Kelsey jokes, "and she was like, 'He's going to need you so much more when he's a toddler.'"
To keep the book relevant despite Squarespace's constant evolution, Kelsey focused on concepts rather than specific button locations. "I wanted it to feel like even if where the buttons are change, you can still read this book two years later conceptually and understand what you're talking about."
The book includes insights from multiple members of the Squarespace community, making it a collaborative resource rather than just one person's perspective.
The Power of the Squarespace Design Community
Throughout the conversation, Kelsey repeatedly emphasized how unique the Squarespace community is compared to other website builder platforms. When asked about her biggest competitors, her response was telling: "I don't really have an answer to that question because everyone here is a puzzle piece. It all fits together."
Rather than fighting over clients, Kelsey explains that designers in the Squarespace community serve distinct groups and cheer each other on. This collaborative spirit extends to how designers share knowledge, celebrate each other's wins, and support one another through challenges—creating an environment where everyone's success contributes to the whole..
For designers new to Squarespace, this community offers an invaluable resource. Whether you're troubleshooting a technical challenge or looking for business advice, the Squarespace community consistently shows up to help.
Leveraging Tools to Scale Your Squarespace Design Business
As Kelsey's business has grown, the right tools have become essential for efficiency and creative expression. This is where solutions like the SquareKicker Extension come into play—enabling designers to push beyond Squarespace's native limitations without requiring custom code.
The SquareKicker Template Store has also created new opportunities for designers. "We had these amazing conversations and it was all about, 'We need something to help with the highs and lows of client work. We really want to create templates, but Squarespace doesn't really have a way of doing that,'" Kelsey explains.
By creating templates with advanced design features, designers can showcase their creativity without client restrictions while also generating additional revenue streams. These templates help other designers work more efficiently, creating a cycle of support within the community.
Key Takeaways for Scaling Your Design Business
Kelsey's journey from accidental entrepreneur to Inc. Magazine-recognized founder offers several crucial lessons:
Start before you're ready. Sometimes the best opportunities come from saying yes to practice pitches or projects slightly outside your comfort zone.
Embrace structure as freedom. While creatives often resist rigid schedules, strategic structure actually creates space for creativity and growth.
Prioritize team culture from day one. Building a business where people feel valued and supported isn't just nice—it's essential for long-term success and quality work.
Know when to step back from client work. As your business grows, your most valuable contribution shifts from doing the work to creating opportunities for your team.
Leverage your community. The Squarespace design community offers genuine support, knowledge sharing, and collaborative opportunities that benefit everyone.
Connect with Kelsey
Website: Week of the Website
Instagram: @weekofthewebsite
YouTube: @weekofthewebsite
Take Your Squarespace Designs Further
Whether you're just starting your web design business or ready to scale to the next level, the tools you use can make all the difference. The SquareKicker Extension empowers you to create truly custom Squarespace websites without writing code, giving you the creative freedom to deliver exceptional results for your clients.
With features like horizontal scrolling, sticky sections, scrolling effects, and advanced hover animations, you can push beyond Squarespace's native limitations and build websites that stand out. Plus, the SquareKicker Template Store offers premium templates created by professional designers—perfect for streamlining your workflow or generating additional income.
Ready to elevate your Squarespace design business? Start your 14-day free trial of SquareKicker today—no credit card required. Discover how the right tools can help you work smarter, deliver better results, and build the design business you've always envisioned.
