Catching Up With... Kelsey Gilbert-Kreiling


August 22, 2023


Floor Banga


Agency co-founder, podcast host, and author Kelsey Gilbert-Kreiling chats to us about finding small acts of creativity to unblock your creative spirit, working with celebrity clients, and her latest work: publishing a book and a course.

Hey Kelsey! Can you start by telling us a little bit more about yourself?

Sure! I live in Chicago, I’m a co-founder and mom (of 2yo son Jasper 💙). Nine years ago I co-founded a web design agency called Week of the Website with my very close friend and business partner Mallory Ulaszek. We build websites on Squarespace for creatives, small businesses, and innovative non-profit organizations. And we do it all on Squarespace, with about 15 team members!

How would you describe your aesthetic in three words?

Bright, friendly, and playful!

...and in emojis?

✨ 💜 🦐

What’s the secret of getting things done, making an impression, and running a business with your close friend?

So, we basically broke all the rules of ‘you shouldn’t do this or that with your business partner’ (short of a romantic relationship), like traveling together, being roommates, and hanging out with each other's families. To succeed, it's important to really commit to our cofounder relationship like any other long-term partnership. This means investing time, talking out issues, and understanding there will be ups and downs, but also making time to do non-work things to balance the intense decision-making days!

We broke all the rules of what you should or shouldn't do

This partnership started when I was doing a lot of different things for a hospitality group, including building websites for their new restaurants. We then realized that specifically in that industry, clients show up with negative two weeks on their planning. They needed a website like two weeks ago. And the foundations of Week of the Website are really built around those constraints: a little bit of time, and not an unlimited budget. And, using Squarespace has let us do that!

Clients showed up needing a website, like, two weeks ago

The success lies in two things:

1. Always have a project manager to keep things on track, so the designer and developer are separated from that, to have more creative space.

2. Create predictability, once you get it down to a system, you do not need to rely on people making decisions about whether we should or shouldn’t let this client slide, or about due dates, and so on. It's very predictable and that predictability helps everybody stay on track.

So your golden advice is to let the creatives focus on the creative parts?

So they don’t have to focus on the too damn boring stuff (laughs)..?

I do think having that separation can be really helpful. I hear from a lot of people: ‘How do you keep projects on track?’ and ‘How do you get people to turn things in on time?’

And the answer is always that we have someone on our team whose complete job it is to make sure that happens. Of course, most early-stage designers don't have that opportunity straight away. You see that designers and copywriters partner all the time. I think there should be more creative project management partnerships in early-stage creative careers because it would help clients and (beginning) creative teams be more successful.

There should be more creative project management partnerships in early-stage creative careers

You've worked with really big names such as writers Jessica Knoll and Jenny Han, and also chef Rick Martinez. How did those collaborations come to be

There's this interesting waterfall effect where you do enough projects and then find yourself in the right place at the right time. For example, Jenny Han contacted us through the Squarespace experts platform. I am a big book person, and when this happened, I was like: ‘Oh my God, do you all know who this is?!’

This was before her movies and TV shows, and this year we redesigned her website as her career evolved. This is my favorite thing, as people evolve, their needs change as well, and Squarespace is perfect for this, as it’s so flexible.

So which projects are you most proud of?

I'm at a point now where I don't get to build websites very much anymore. I don’t have the consistency in my schedule since I’m a mom, so I'll be honest the projects I'm the most excited about are things that my team has built!

It’s a big change to go from someone who is the lead creative to now doing the business development. But, it's most special to me to see things that start as a conversation with me, grow into full projects.

One of my favorites is by one of our designers, Alex Lucke, who's really phenomenal. She built a website for Taja Dockendorf, who owns a branding agency. That project was very cool because it's one thing to work with a client that's not at all related to creative work, but when you have another creative who has their own very established design practice come to you to work with them, that's very special.

Another favorite is the website of Rick Martínez, I love that it's just so warm, bright, and fun:

How do you stay inspired?

Something I have had to actively work at is the busier you get, the harder it is to find space for inspiration. Currently, I feel the most inspired around childlike things. For example, one day I really want to write children's books. So most inspiration comes from ideas for stories and I find the most joy in those moments of creation in my day, whether it's making up a new song or drawing something for my son.

I also have this funny routine, where I make little animals out of the wax of Babybel cheeses that I surprise my office manager with because otherwise, I'm running from sales call to strategy call to standup.

And I think that's the hard part of maturing as a creative when you decide to grow into the agency model. The thing that got you into it, your creativity, your design, your aesthetic, etc. becomes less the focus of your day than it is building and growing your company. And that's sometimes tough, so I think it’s important to keep inspired through simple things where there’s nothing at stake.

The thing that got you into it, your creativity, becomes less the focus, so it's important to keep inspired through simple things

Which creatives inspire you?

I love Jillian Barthold’s work- it’s soulful, bright, whimsical, fun, and meaningful. We went to university together and visiting her studio a few years ago in Portland is such a bright memory for me. Her Book Club illustrations make my heart smile.

Katie Meuser is an abstract artist in Chicago and I love her use of floral and colors. I actually used part of my book advance to buy a piece of hers to commemorate this moment in my life and it felt like a very special link in the creative ecosystem.

In my lifetime, I’ve done more work to the music of Ólafur Arnolds than any other artist. His work is otherworldly- my husband and I have visited Iceland quite a bit and were married there in 2017. Putting on his music helps me tap into the color and feeling of this very special place.

I’ve always loved and admired what Roanne Adams has created at Roandco- no one builds a brand like they do.

So, you’ve recently launched a book and course! What’s your key to learning new things as an adult?

When you begin learning something, there's so much you don't know yet. So you are feeling a lot of friction and the sense of being challenged. However, we’ve been taught that when it feels like there is tension or friction, that means that something’s wrong.

But when you're learning something new, that's not true. Those moments of ‘I don't get it’ or ‘Where is that? I don't understand?’. That's part of the learning process. So I really emphasize in the course that you can't mess this up. It's your website! It's just the internet. It's just pixels. It's fine!

It's just pixels, it's just the internet, it's fine!

What’s the magic element that people will learn from your course?

I think the fact that I do not focus heavily on the use of code and my approach is to really teach people to use the Squarespace platform to the best of its ability before reaching for some of those out-of-the-box tools.

My course is basically a designer's insight on how we use the tool for building for our clients and serves as a compliment to other people's work. Rather than competition, it’s a compliment. And I love that about it.


Want to learn how to master Squarespace like Kelsey? Her course is now available and you can try the first lesson for free!

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August 22, 2023


Floor Banga


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