Want to Transition Between Teams at Your Company? Here’s How 2 Women Accomplished That

“My unique career path has shown me that I thrive in the unknown,” says Kymbia Ainsworth. “It’s like I get to put together one big puzzle. Yes, the overall goal of success and money is there, but it’s the process. How you approach putting the pieces together makes the journey unique.”

Ainsworth’s own unique journey started in retail. She worked at Anthropologie for about three years, and was able to gain experience in virtual merchandising by executing visual rollouts each season for their flagship store and store openings. 

Eventually, Ainsworth discovered the next piece in her career puzzle: Squarespace. “I joined Squarespace as a customer advisor four years ago,” Ainsworth says. But this was only the first of many steps she’d take at the company. “During the pandemic, I seized the opportunity to take a virtual digital marketing course at Oxford,” shares Ainsworth. “Not too long after I completed the course, there was an opening to join an Advisor team at Squarespace that was answering support questions via Twitter. My Team Lead at the time remembered the course I had taken and thought I’d be interested. I said yes, and that group of Advisors has since evolved into a specialized team of Social Media Specialists.”

Supporting team members on their unique career journeys is a common occurrence at Squarespace. For instance, Ainsworth’s coworker, Teresa Salazar, has also had a one-of-a-kind journey.

Salazar started out in retail, before eventually starting at Apple retail. “Throughout that time, I had the opportunity to experience different roles," she tells us. "I gained experience in sales, visual merchandising, mobile support, training, and created strategy for high-demand product launches that optimized not only the customer experience but the ways employees worked.”

This experience opened her eyes to different career paths, and, after she joined the Squarespace team as a Customer Support Advisor, Salazar knew she would want to move from the customer support team in the future. “I shared my interest in finding an opportunity on the People team with my manager at the time, who was very supportive,” says Salazar. “He and I worked together to find stretch projects or tasks that somewhat overlapped with the kind of work I was interested in.” 

Before Squarespace, Salazar had never fully considered a career in HR. However, the support she received at Squarespace helped her make the switch to an employee engagement lead position. “I feel like everything fell into place at the right time,” she tells us.

We caught up with both Ainsworth and Salazar to learn more about how they transitioned to different roles within Squarespace — as well as their advice for other women looking to make career changes. Here’s what they had to say.

To start, can you tell us a bit about your current position and how long have you been in this role?

Ainsworth: As a social media specialist, I am responsible for both content moderation and customer engagement across social media platforms for the Squarespace and Unfold product. I love that it’s a global team; I’m based in New York and work with teammates in Portland and Dublin. 

Officially, my role started in May 2022, but it’s been over a year of prepping and rolling it out. Since the team is new, I also get to contribute to internal documentation, onboarding, and training new team members. 

Salazar: I’m an employee engagement lead and, in my role, I get to collaborate with different teams to create strategic programs that reinforce the Squarespace culture. It’s a really fun side of HR that’s centered around how to keep employees excited to come to work at Squarespace. We come up with events and programs and are often behind the scenes of large projects providing feedback around how the implementation of some of these things may impact the employee experience. I’ve been in the role for around four years now, and it’s a career that has allowed me to bring some of my creativity to what I do every day. 

You both were previously part of Customer Operations before transitioning to your current roles. How did your time Customer Operations prepare you for some of the challenges that you face now?

Ainsworth: I’m really grateful to have entered Squarespace as a customer advisor. The role required me to become a product expert. Every customer interaction was a mini tutorial I curated on the spot with annotated screenshots and video demos. Being in tune with customer voice, knowing the brand’s tone and voice, and making quick decisions are all essential for the role I am in today. I don’t think I would’ve picked up these skills at the same level if I hadn’t started as a customer advisor first.

Salazar: The customer support role was one of the most challenging roles I’ve ever had. You have to be extremely proficient with the product while also being an expert at coming up with creative solutions for your customers. It challenged me to not only be well versed with the platform, but also taught me how to communicate with people in the most effective way, both verbally and in writing. That opportunity to work in that department is a huge driver to my interest in bringing the best experiences to our employees every day. 

How has Squarespace supported your transition from team to team?

Ainsworth: I’ve been fortunate to have managers who want me to succeed and who are transparent. When transitioning into the new role, it was made clear that: “not everything is laid out. We are building the blocks as we go. If there’s something you don’t know or if you have any ideas, please feel free to contribute.” I felt empowered and valued. That mattered to me more than having everything mapped out. 

Salazar: One of the things that I’ve appreciated most about my time at Squarespace are the amazing managers and leaders I’ve been able to work with. My first manager at Squarespace was extremely supportive of my interest in moving into the People team and gave me a lot of opportunities to work on projects that would allow me to gain new skills to prepare for my next role. My current manager is one of the most kind and honest leaders I’ve ever worked under. Even in my current role, I still feel like it’s a safe space to express other interests I have, and my manager and director are so great at finding ways for me to collaborate with other teams to explore my interests. I feel very lucky!

What advice do you have for women who are hoping to transition between teams at their company and pivot their careers?

Ainsworth: Stay inspired! Whether it’s subscribing to newsletters, taking courses, club sports, or traveling, you never know what experience or activity will help inform your next decision. It’s attractive to see someone who can bring enthusiasm and knowledge outside of just being able to do the job. It’s also easier to spot the right opportunities when you’ve invested time in yourself outside of work.

Salazar: It’s never too late to make the move into a role you’re interested in. Oftentimes, we put so much pressure on ourselves because of factors like financial and job security, the people depending on us, and we get in our own heads that it’s too late to try something different. I’m a firm believer in ensuring that the job I have is something I enjoy because I’ve definitely been in roles where I woke up dreading going to work, and that’s never good. I think it’s never too late to make that move or to take the time to get the training and whatever else you may need to move into a career you’re passionate about. 

What’s the one career move that you’re the most proud of?

Ainsworth: I am most proud of my decision to join Squarespace. Previously, I worked in visual merchandising and management in retail. I’m glad I took the chance and pivoted into tech. My creativity and business acumen have been beneficial at work. I’ve also been fortunate to have great managers who want to see me succeed.

Salazar: I was born and raised on Guam and, if I’m being honest, I think I’m most proud of my decision to move away from home (and most of my family) to find an opportunity in the U.S. It was definitely one of the hardest experiences, but also one of the most rewarding. 

Looking back at your career, what has kept you at Squarespace?

Ainsworth: The people. Employees at Squarespace are just as dynamic as our customers. Even if your career path is uncertain, having great coworkers makes all the difference. I enjoy engaging with my coworkers. They’re smart, creative, and intuitive. 

Also, career development is a two-way street. I love that my manager, who is also a woman, is excited for my development as much as I am. When she holds our one-on-one check-in meetings, I don’t feel like I’m last on her list. I have ownership of setting and leading the agenda when we meet. I’m also a part of BASS (Black at Squarespace), which is an employee resource group at Squarespace. Many women have held leadership roles in this group and are helping to cultivate inclusivity at Squarespace and hosting some amazing events. Examples of women and People of Color have grown since I joined Squarespace four years ago, which has been exciting to see.

Salazar: If you ask anyone this question 9 times out of 10 they’ll say it’s the people. I’ve met some of the most talented and collaborative people while working at Squarespace and have learned so much from my peers during my time here. The talent we have at the company is top notch!

Another huge factor has been the flexibility and the respect for work-life balance. We have a great time off policy, and my leaders have always been understanding and accommodating when unexpected things in life have come up. I’m cared about as a person, and that’s not always the case in corporate companies.