What I Learned About Design at Squarespace

3 Lessons from two years at a startup in New York.

As I began to clear out my desk that last week at Squarespace and thought about saying goodbye to my colleagues, I realized I felt the same way I did my last week at college, knowing the end of my time on campus was drawing to a close. It was just as difficult to mentally prepare for my move back to California as it was to pack up my dorm room for New York two years earlier.

I began my tenure at Squarespace as an intern through the NYC Turing Fellows program, after which I was hired full time as a Design Engineer and then made my way over to a Product Design position a few months after that. The company was at around 60 people when I started, but it had ballooned to almost 200 by the time I left. It was an invaluable experience for me, and now that I have had time to reflect on it, I can finally put into words the lessons I came away with after my time there.

1) Your Culture is Your Product

If you were to get to know the personalities of the people at Squarespace and how they interact with one another, none of the choices made in the product would surprise you. It is a direct extension of Squarespace’s culture, from the arresting imagery to the stark settings interface.

Although I discovered it during my time there, this concept is not a new one. Zappos’ CEO Tony Hsieh has written before about how your culture is your brand because company values shine through at every touchpoint with a brand, from conversations with employees to the little cat that drops items into your shopping cart. Company culture informs decision-making and execution, translating to the thousands of small decisions that make up a product.

I also saw first hand at Squarespace how the source of a company’s culture is its “ruling body’s” personality and values. If you are a friend of CEO and Founder Anthony Casalena, you will have a good idea of what his employees care about in the workplace. Squarespace’s culture is a direct extension of his ideals, and it manifests itself in every aspect of the company’s product. Look to the values of your company’s leadership, and you will begin to understand what the company is likely or unlikely to be able to accomplish. Plans aligned with the culture—notice I didn’t say mission statement—will succeed, and those that do not will be poorly executed and doomed to fail.

If you can’t think of an example of how this is true in your company, take a look at how Google’s design language did not evolve until new CEO Larry Page mandated that it should. Google is a perfect example of how a company’s products and brand are a result of its culture, and how that culture is a result of its leadership.

During the very last all-hands meeting I attended at Squarespace, Anthony spoke to us about how he and the leadership team got together to distill the company’s values and presented 8 that would eventually end up on this page. He stressed that the list was an attempt to put into words what we already believed in as a whole, not what they would like us to believe in, or thought sounded good for the company. Indeed every value in that list described how we worked and what we cared about, so there were no surprises.

2) You Are What You Eat

Or rather, in the case of a creative, what you consume. To quote Gavin Ambrose and Paul Harris again:

“[Designers] are cultural scavengers and the appropriation of elements are accidentally or unexpectedly found in their work. [sic]”

I was continually amazed by the examples of good art, photography, and design work that the other designers collected and shared, and my exposure to it made me better at my craft. I believe it is important for every creative to seek out and immerse themselves in great work. Tellingly, the custom at Squarespace was to surround yourself with beautiful, functional tools—digital and physical alike. It was very easy to tell whether a design had reached the right level of finish because it would suddenly claim its place on the USM desk, among the anodized MacBooks and beautiful Phaidon hardcovers on the bookshelves.

Try it. If you are a designer, ask yourself: how does this piece of my work measure up to the other work I love? Did I put in the same amount of care and attention to detail?

3) The User’s Experience is Your Brand

At Squarespace we cared about each individual user having a good end-to-end experience with the product more than the abstract idea of an aggregate, generally positive user experience. How does a single user experience Squarespace, starting from exploring the homepage and continuing all the way through to signing up, creating a site, maintaining it, and interacting with customer care? Using that perspective, the focus when designing and building version 6 was first to make sure that a creative with a portfolio would love the system. This (relatively small) group was a good first choice because it was one of the hardest to design for, and the notion was that solving their needs meant that we would meet those of other, less demanding users in a beautiful way more easily as the system continued to evolve. It was only after providing that group with an experience we were proud of that we moved on to focus on certain kinds of small businesses, like restaurants, etc.. It is a strategy that allows for better design through focus, and more often than not, doing less better leads to more universal appeal.

Anthony was fond of referring to a customer’s Squarespace site as their online clothing, and Squarespace’s brand as more akin to a luxury fashion brand than that of the typical technology company. This ended up being an apt metaphor because high-end brands look at creating product experiences in the same way. You might imagine your average tech company leaving an element a few pixels out of alignment or releasing a feature with missing details just to “get it out there.” Can you imagine Prada or Louis Vuitton allowing a handbag with crooked detailing or releasing an unfinished pair of shoes? A user’s concern is about whether a product meets their needs and delights them, not whether it mostly meets most people’s needs.

Putting it Into Practice

These three lessons also highlight how important it is to choose your company carefully as a designer. Choosing a company that doesn’t just pay design and user experience lip service will make the difference between work you can be proud of, and losing steam trying to execute or painting capybaras. Evaluating a company through the lens of these lessons can show you what it would be like to work there as a creative. 1) What is the culture like and what do the higher-ups care about? 2) What sorts of digital and physical tools and objects are the designers surrounded by? 3) How does a user feel about using the product for the first time? These are the questions I would think about when evaluating working at a new company.

I am thankful to Squarespace for giving me the opportunity to learn these lessons so early in my career as I know I will take them with me for the rest of it. So long, Squarespace, and thanks for all the fish*.

*Confused? Then you’ve forgotten Douglas Adam’s Hitchhiker’s Guide to the Galaxy.

This post was originally published on http://uxdiogenes.com.
P.S. You can follow me on Twitter @uxdiogenes.