Design Chats

Inside Design: Squarespace

4 min read
Kristin Hillery
  •  Jan 23, 2017
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Founded on the belief that there should be an all-in-one solution to creating a beautiful online home, Squarespace makes great design accessible to anyone with an idea and a drive to make something—no security patches or webmasters needed.

Over the last 5 years, with design as a priority, they’ve grown from a 60-person company to almost 600. That’s just one of many reasons we’re proud to say they’re part of the InVision community. We sat down with Billy Sweeney, Design Lead, and Danni Fisher, Product Designer, to find out how Squarespace’s design team operates.

How is the Squarespace design team set up?

Danni: Our product design team consists of 7 designers. We’re part of the broader creative team of 20 designers that includes brand marketing, frontsite, platform, and templates.

Our team structure is fairly flat. Designers champion different areas of the product, like CMS, commerce, mobile, domains, circle, and everything in between.

Related: How to design your design team

What makes this team structure effective, and are there things you’ve changed along the way to make it better?

Billy: We’ve changed our structure a fair amount over the years as we’ve grown—we’re always looking for the most effective organization. Our mostly flat structure allows each of us to work on the things we’re passionate about, which gives the team room to shift around as different needs surface. We recently evened out the number of direct reports that each manager has, which helped a lot in putting together an efficient team.

“In a great creative culture, people feel free to share ideas, opinions, and criticisms.”

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Danni: This year, we introduced a product design weekly sync lead by our Director of Product Design, Michael Heilemann. The meeting focuses on what we’re up to and how we’re thinking, rather than just providing progress updates. It’s loosely formatted, lasting 1-2 hours, but each sync starts with high-level company updates and then dives into an opportunity for each designer to share his or her work and thoughts on the creative process.

We aren’t timeboxed and it doesn’t matter what work is presented—the most important aspect is that each team member has the opportunity to share something. At the very least it’s a chance to work on presentation and communication skills.

Collectively, we offer critiques and ideas to help teammates think through a particular problem they may be stuck on. The transparency that comes with sharing our work and thought process is key.

“Our engineers find InVision super valuable because they don’t have to download individual comps.”

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We also started doing weekly 30-minute peer one-on-one hangouts as an opportunity for team members to gain a deeper understanding of another designer’s project and all its nuances. Each project at Squarespace runs deep, and each designer becomes a “specialist” in his or her respective area, so the goal is to share that knowledge. Again, these hangouts are not to find solutions, but for both parties to ask lots and lots of questions.

Billy: As I’m based in Portland, and the rest of the team is in New York. So I find these one-on-ones particularly useful. I’m given the chance to hop on a video call and screen share for about 30 minutes. It’s a nice way to go more in-depth on a project, to understand the stakeholders, to share technical tips and tricks, and to foster community.

What’s the design culture like at Squarespace?

Danni: These days it seems like every hour there’s a new product, site, app, TV series, or piece of writing to check out. Staying current is a huge part of the design culture—forming opinions on the things we’ve tested, asking questions about the things we haven’t.

Related: What exactly is a design culture?

In a great creative culture, people feel free to share ideas, opinions, and criticisms.Twitter Logo Designers usually have some sort of obsession that gives them an angle from which to measure good design. Whether you love typography, woodwork, film, music, or math, it’s that ability to make comparisons that translates into a sense of “good taste” and valued contribution.

In a broader sense, great company culture comes from caring for the product, brand, and the users.Twitter Logo When you’re surrounded by people who share a common goal, communication channels open up, the vibe is positive, and a natural form of camaraderie develops.

Billy: Our leadership team plays a major role in establishing the company culture by way of hiring decisions, communication styles, and opportunities given to employees. Our CEO sits right next to us, in the same kind of chair, at the same custom concrete desk, with the same computer equipment everyone else has. This sends a profound message to the company about equality of ideas, and the fact that he’s not tucked away in a glass office somewhere in a suit speaks volumes to the entire organization.

How does your team communicate with each other? And how do you communicate with people on different teams at your organization?

Danni: The product design team sits in a group, allowing for a lot of in-person communication. We’ve experimented with different seating arrangements to see whether designers should sit together, or if we should be seated next to other colleagues like engineers or product managers with whom we work closely.

Currently, we’re finding it valuable to be closer to other designers. That said, we often move around to sit with other team members depending on our projects’ needs. It’s interesting to see how communication shifts depending on where you’re seated. You hear different jokes, learn about others’ values and priorities. We’ve found it to be a valuable experiment.

“InVision prototypes help our team quickly iron out functionality.”

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Billy: We use G Suite by Google for most of our internal written communications, be it spreadsheets, documents, or slides. There are a variety of chat channels, including one for each team for our daily chatter. But our open-office floor plan is also very conducive to in-person communication. We’re lucky to have an open environment with plenty of different meeting spaces that allow for collaboration but within and across teams.

For the product design team specifically, we’re constantly sharing screenshots and recordings of our work. This continual feedback loop has proven very helpful in building and maintaining an open team culture. This sense of transparency drives home the notion that we’re not competing against one another, but are rather all working towards the collective success of the team. To that end, we often celebrate together, grabbing drinks or dinner after work.

What are the most important values you try to see reflected in your designs?

Billy: Love. Family. Risk-taking. We see our colleagues and customers as family—we’re all in this together and enjoy helping one another. Taking risks keeps us on our toes and motivates us all. Love helps eradicate pain, foster growth, and is downright beautiful.

Danni: It’s important to me that we’ve taken some risks in the design. That what I’m working on isn’t a super obvious solution, it’s had to get buy-in from others.

“Take risks with your designs.”

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How does your team document collaboration?

Danni: Our formal meetings are usually run by one person on the team who keeps a Google Doc and goes through the agenda to make notes of decisions made and what people are working on that week. That document will link out to supporting docs and who is responsible for specific tasks.

In a casual environment, sometimes a quick photo of the whiteboard is enough to document what went on. In any case, we will usually follow up with an email to confirm what was discussed and follow up on any questions.

What’s the most powerful part of your design process?

Danni: We always work really closely with engineering from the beginning, but one of the more powerful moments is when we prepare to release a new feature or product. Engineers and designers will sit together over a couple of days and work out all the final tweaks. We find bugs, we make last-minute changes, we get things signed off. Proximity lets us focus and move quickly.Twitter Logo Those last few days before a release are always pretty exciting.

How do you hand off designs to developers?

Danni: Our engineers have a really keen design sense, which I feel is quite unique to Squarespace. We’re in constant conversation with each other, so there isn’t really a culture of hand-off. We work through problems side-by-side on a daily basis.

We understand that it’s important to develop the relationship between designer and engineer. Everyone has a style, and getting to know each others’ is super valuable.

“Take the time to ask developers how they prefer to collaborate.”

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I take time to observe and ask engineers how they prefer to collaborate. Lots of talking? No talking? Technical jargon? Prototyping on the fly? From there, we find a vibe that works for the two of us. I ask our engineers questions all day to see how they think, both as an engineer but also as a user. It’s important to me that engineers know we can truly talk, and it’s not always about sign-offs and closing tickets.

Can you talk a bit about Squarespace’s branding and overall design?

Billy: Once we shifted our brand imagery to showcase real customers and elevate their stories, it made a big difference. We found that having genuine customer stories as a foundation for our brand messaging is the most honest way for us to communicate our values and value proposition to the world.

Danni: We put a lot of effort into our customer showcases. It’s very cinematic. Comparatively, the design of our platform is intentionally toned down to let the customers’ content and website be the focus.

How do you know when you’ve created a good experience?

Billy: A good experience is an emotional responseTwitter Logo, so we typically know it’s right when it simply feels good.

Danni: It’s generally a good sign when we’re down to just tweaking styles. When you know the functionality is solid, and now you’re just getting caught up in what level of opacity to use on a button.

Squarespace’s office in NYC.

Is business strategy a design discipline?

Billy: Both seek to solve a problem with deep thinking, data, intuition, new ideas, and testing. So, by that measure, design and business strategy are largely the same discipline.

Related: Designers shouldn’t code—they should study business

Danni: Yes, you’re working towards the same goal but with a different output.

How do you use InVision as part of your design process?

Danni: I use InVision to create rough click-through prototypes to share with my team so we can iron out functionality. I love how I can share an InVision link with everyone once, and it’ll keep updating as I make my edits.

Our engineers have found InVision super valuable in that they don’t have to download any individual comps or worry about whether they’re looking at the latest version—just refresh the online prototype.

Once we have the final flow, I’ll share it with our manager to get design-specific feedback and ultimately a final sign-off.

“We use InVision to share concepts, collect feedback, track progress, and get final approval.”

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How has your role as a designer changed since you first started? And where do you see things headed?

Danni: I started in print and packaging design for physical products. Now, in a way, I do the same thing for digital products. Both require a similar type of logic and problem solving, and aim to help a user unpack and successfully use a product.

I see design heading towards helping causes. Designers want to use their skills to help people in their daily lives. Eventually, I think that will align more and more with industries such as education, healthcare, agriculture, and the environment. That area of innovation is really exciting.

Billy: When I first started designing, an identity system was about as holistic as a project would get. Now I’m designing much more complex systems to support all different kinds of functions, sometimes end-to-end, that only deepens my love of holistic design.

As for where design is headed, I think it’s plausible—though unfortunate—that eye candy production will continue to rise, while hard issues remain ignored. As a society, we tend to struggle with helping our neighbor. We so often focus on ourselves. But what if we lived in a world where people voluntarily gave up their excesses to help others in need?

My hope is that the future of design will be part of a massive team effort in which industries work together, collectively building a stronger, more sustainable global culture. I can’t wait for our ever more digitally connected world to become truly connected, for everyone’s benefit.

What are 5 things you know now that you wish you knew when you first started out as a designer?

Danni: Here are mine:

  1. Everyone has to do bread-and-butter work
  2. Give your manager positive feedback
  3. Parents will never really know what you doTwitter Logo
  4. It’s fair to negotiate your contracts
  5. No one’s layer formatting is perfect

“A good experience is an emotional response.”

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  1. It takes a long time to build credibility. You likely won’t land a dream project right out of school. Plan carefully. Curate your book. And do what it takes to pay the bills. Humility pays off.
  2. A collection of 5 really well designed typefaces is far better than a perfectly organized and tagged collection of 5,000 average ones.
  3. Moving faster in the early stages of a project leads to a better final product.Twitter Logo Trying a ton of directions helps to uncover the best idea for you to refine.
  4. Relocating to a new city provides a whole new set of opportunities. It opens your mind, and helps you see in a new way.
  5. It’s strangely difficult to sell someone on good design. I spent a lot of energy trying to convince potential clients they should hire a designer, when I should have sought out the people who were already interested in designing great things.

Photos by Nina Robinson.

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