Lessons on Creative Entrepreneurship from Kelsey Gilbert-Kreiling
Location: Chicago, IL
Started using Squarespace: 2011
Title: President and CEO of Week of the Website
For many designers, web design is a conscious career choice. For others, it arrives quietly, beginning as an outlet for personal expression and evolving into something more. That was the case for Kelsey Gilbert-Kreiling, who began tinkering with HTML and CSS to customize her blog and Tumblr layouts as a teenager. The Circle Platinum Partner and Community Leader later founded Week of the Website, scaling her creative side project into a multi-faceted web design studio.
Now the author of Squarespace from Signup to Launch and creative educator behind Better Than Launched: Advanced Squarespace Tools, Kelsey reflects on the moments that shaped her creative direction, the lessons she’s learned building client websites, and what she believes makes for a successful, strategic web design practice today.
What originally drew you to web design, and how did you get your start in the industry?
Web design crept into my life as a means to an end. Like a lot of millennials, I began learning HTML and CSS in service of blog customizations. It became a natural way to express myself, moving to Tumblr, then eventually creating an online fashion publication while I was in school for fashion design.
I didn’t have the technical chops to build the website on my own, but I designed the homepage and blog pages, asking a former boyfriend to build it for me. I didn’t much enjoy being beholden to someone else to make things for me, so as I progressed through my education, I added graphic design and typography courses to broaden my design studies beyond just clothing.
For a long time, web design was just a way I shared other types of creative work with the world. Years later, when I began working for a hospitality company in a technical role, they asked me if I could build websites for some of their new restaurants, and that’s really where the design side coalesced.
How did the concept of “Week of the Website” begin? What tips do you have for other designers who want to adopt a similar model?
Week of the Website was imagined after a meeting with Jeremy Schwartz, Senior Director, Channel Partner Business at Squarespace in early 2015. My former business partner and I were in town for another client project and visited the Squarespace offices to get to know more of the team. We had been building websites as a part of our agency offering but did not love the process we were following. I asked Jeremy if he was seeing any cool innovation in the area of professional Squarespace design, and he mentioned Benjamin Manley’s Knapsack Creative as a group that was building websites in a day. I remember my reaction being, “Whoa! I do not want to do that!”
After that meeting, we were walking back to our hotel, and I remember telling my partner, “I don’t want to build websites in a day, but we are really good at project management. I think we could do something special in a week.” We spent a good part of that trip thinking about the process and how it could work, and when we returned to Chicago, we tested the Week of the Website process. Though we’re always refining, the sprint methodology and project management approach have stayed largely the same!
My biggest advice to folks looking to create a similar model is to make sure it’s anchored in your strengths. When we created the Week of the Website process, we knew we had the background and foundation to set deadlines, guide clients, and execute beautiful, custom sites that clients could use, edit, and own. A time-based project type might not be a good fit for everyone. There are so many ways to specialize your services, and the only reason we’ve been able to keep doing this for more than a decade is because it’s truly an expression of our team’s innate skills.
How do you align your team in skill, creative vision, and the goals of Week of the Website?
We have really clear values as a company: collaboration, ingenuity, agility, compassion, and excellence. This is truly the lens through which we see everything, from relationships with each other as collaborators and teammates to how we choose and support our clients. Having these values makes it so much easier for us to make decisions and stay aligned as a team.
When we go through the hiring process for designers and project managers, we’re not only looking for people who have these qualities, but also folks who get what we’re trying to do, want to do it, and have the capacity to accomplish the goals we set together. Practically speaking, we have quarterly team meetings where we celebrate our successes and talk candidly about our challenges. Our Slack is always busy with team chatter, whether it’s collaborating on a technical challenge for a client or sharing fun internet things.
What tips do you have for other agency owners looking to refine their project and business management skills?
First, there are a few things about project management that will always be challenging, and I think it’s valuable to understand that from the beginning. It will always be tricky to get clients to give you what you need, and expecting that friction makes that job feel a bit easier. It feels hard, because it is hard.
That said, consistency in communication makes a really big difference. By the time a client has started a project with us, they’ve heard the same information often—in their initial call, in their proposal, in their contract, and during their onboarding call. By making sure everyone involved in the project is on the same page, you avoid all of the understanding-based challenges of the project management role.
Rounding up client content and assets is a common pain point for many designers. How does Week of the Website mitigate this?
We’ve handled this in a lot of different ways over the years, but we come back to the simplest system every time. No matter how many times we’ve tried to institute a dashboard or more complex process, we see the most success with good ol’ shared folders. I stress to our team that our job is to meet the client where they are, and that’s why our projects all have a dedicated project manager to help make it easier for the client and developer. We share content deadlines with the client early and often, remind and coach them, and support them as they onboard for their process.
What design principle is essential for creating the best user experience?
It’s empathy, always. I think our team is particularly good at listening to our clients, asking good questions, and intuiting their needs, while also thinking about how the user will experience what we’re creating. You can’t fake that kind of curiosity, and clients feel it. It’s so easy to forget that design is the act of creating things that people use. Designers who return to that principle will build beautiful, useful digital experiences that last, and I love that.
AI searches are becoming increasingly prevalent. What best practices should web designers employ to ensure their projects are discoverable?
The most important practice with generative search is flexibility. So much is changing, so quickly. The more nimble, mentally, you can stay, the easier it will be to adapt to shifting best practices. With AI search, we see a focus on content that answers a question—FAQ is particularly powerful. Conceptually, I encourage folks to think about what type of inquiry they would make to find their own work. Blogging will continue to be important, and it’s a really special way to share your client’s perspective on issues that may help them stand out. I’d also recommend that folks make sure they have not turned off AI crawling on their Squarespace site; that will definitely make things tougher!
How do you make the most of Circle membership?
In contrast to the reality TV mantra we all know well, I am here to make friends. I have found so much joy in the network of Circle members that I grew to know at Circle Day, and through other forms of connection throughout the year.
We all share this unique piece of our careers, yet work in such different ways. I learn so much from all of them, and every time I have a question or something that I’m stuck on, I know they’re going to be the first people I turn to outside the Week of the Website team.
Key takeaways
The following are key insights from Kelsey’s interview:
Build your services around your team’s core strengths to create sustainable, effective processes
Strong team values and consistent alignment are essential for scaling creative collaboration and delivering quality work
Clear, repeated communication throughout a project is key to managing expectations and avoiding misunderstandings
Simple systems and hands-on support help clients deliver assets on time and ease the pain points of content collection
With the development of AI search, empathy and flexibility are essential to creating user-first designs that remain discoverable and impactful
Read more from Kelsey on the Circle blog:
Watch past events with Kelsey:
Learn how Kelsey pitches to clients:
Want more?
Check out Squarespace Circle, Squarespace’s program for professional designers and web design agencies. Along with exclusive content, discounts, and other perks, Circle brings professionals together from across the globe to exchange advice while connecting with new clients and collaborators.
