The Road Less Traveled — How This Squarespace Designer Succeeded

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Photo Courtesy of Squarespace

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July 14, 2024 at 9:39AM UTC

Annecy Smith, a product designer at Squarespace, says the most appealing aspect of joining the Squarespace team was the opportunity to be part of empowering people with creative ideas to succeed. That and the “incredibly sleek” office space.

She joined the company as a marketing strategist about four years ago before transferring to the product department. While her path was anything but traditional, she tells Fairygodboss that sticking with the same company was key to her success.

“By learning from a variety of Squarespace colleagues for longer, I’ve acquired legacy knowledge that I can use as a resource to better inform my ideas and decisions,” she says. “Second, I’ve naturally developed a sense of loyalty and evangelism for Squarespace, which imbues my work with meaning and makes it more fun. And lastly, I believe my tenure gave me the credibility to make a lateral shift within the company because I had already built trust in my abilities from my previous role.”

Smith also recognizes the significance of Squarespaces’ female leaders in her success. She says that a crucial aspect of development is having other “truly iconic women” she could look up to.

“Both teams I’ve been a part of are led by women—on the marketing team, the chief marketing officer is Kinjil Mather; on the product design team, the VP of product design is Megan Man,” she says. “Many companies talk about female leadership as a theoretical goal, but Squarespace has established it as core to its success.”

Here, she tells Fairygodboss more about how she ended up where she is today and her best career advice for other women on similar career journeys.

Tell us about your career path. How did you get to where you are today?

Nowadays, people always seem surprised when I tell them I have a degree in Economics. But as an 18-year old, I believed that practicality came before passion and I naively assumed that I’d find myself pursuing a career in the elusive world of “finance.” Luckily, after speaking to alumni across the industry and a few internships here and there, I realized this was decidedly not my path.

 I’ve always been artistically-inclined, so I knew I needed more creativity. Still, it wasn’t immediately clear how to translate that creative energy into a career. So I landed on performance marketing, thinking I could apply my analytical background within a creative domain. I enjoyed the work and especially loved my team, but being in an analytical role within a creative environment left me wanting more. I wanted to be a maker— a creator. Then, in a serendipitous meeting where Marketing and Product were presenting projects, a product designer shared how he uses storytelling in his work. I was fascinated.

 I started to research product design and realized that it just might be my dream job. I began getting coffee with members of the product design team to understand their work. They were unfathomably kind and receptive. I learned it wasn’t just about pretty visuals; they worked to solve intricately complex user problems. I was sold.

 Soon after, I enrolled in night/weekend classes at Pratt. I still worked my marketing job during the day. But any free time I had, I threw myself into practicing my craft and studying design thinking. One day, to my surprise, one of the mentors I’d made on the Product Design team encouraged me to apply to an open role. I had the opportunity to interview, and eventually, I had my dream job: a Product Designer at Squarespace.

What projects or programs are you currently working on? What about this type of work most excites you?

As you may have guessed, I’m really enjoying my dream job. I work on the Email Campaigns product, giving Squarespace users the ability to market themselves and/or their business via email marketing. My team and I are currently in what we call the “Discovery Phase.” Although this is a continuous process, we’re almost solely focused on discovery right now, which is a really exciting part of the job.

As a team, we are collecting and synthesizing data and qualitative insights about our users to inform new opportunities that might help us achieve our quarterly goals. It’s rewarding to hear from real users in order to understand their pain points and frustrations, so that I can later design a solution with them in mind. I also enjoy how collaborative this part of the process is: design, product, engineering, research, and content all problem solving together, each representing their respective disciplines, to inform a holistic solution. 

What’s the most memorable piece of career advice you’ve received?

Ask for what you want. This isn’t an adage I was explicitly told, but more so a trend I began to pick up on from the women who I admired early on in my career. I noticed men did this too. In fact, they did this much more often than women, likely due to the societal norms with which we’re all too familiar. But that’s why it was all the more powerful to me when I saw women do this well and confidently walk through the doors it opened for them.

 It’s so important to ask for the project, ask to be in the meeting, ask for additional support, ask for what you need to be successful. It’s always beneficial to have others help, but I believe that you truly are your own best advocate when it comes to your learning and development.

 I asked for meetings with the product designers. I asked about their role. And I eventually asked for an interview. And so, it just goes to show: I wouldn’t be where I am today had I not asked.


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