How Did I Become a Director? I Took Risks, Found My Focus, and Joined a Supportive Company

Sponsored by GlossGenius

Taylor Armstrong

A photo of Taylor Armstrong,. Courtesy of GlossGenius.

Profile Picture
Fairygodboss
May 28, 2024 at 12:50PM UTC

Sometimes, the best moves in your career journey start with taking a risk. That’s certainly true for Taylor Armstrong, who made the big decision to leave a startup company she helped build on the East Coast to take a job on a support team in San Francisco — selling all her things and driving across the country to make it happen. 

“It was a risk that took me out of my comfort zone and, at the time, felt like a step back,” recalls Armstrong. However, this ended up being the career move that she’s proudest of. “It was a step back to take a step up, and it created so much opportunity and growth in my career,” Armstrong tells us. “It was a decision that got me to where I am today, and I wouldn't change that decision for the world.”

Today, Armstrong is the Director of Customer Experience Operations at GlossGenius, a company that empowers small business owners to be more successful by offering a range of business management tools including booking and scheduling, marketing, analytics, payment processing, and much more.

Although she’s only been in this role for a year now, Armstrong shares that she’s already seen tremendous growth. “This role started as an opportunity to focus on operations but quickly grew to include much more organizational strategy and management — and I couldn’t be happier,” she tells us. “I head up our Customer Success, Technical Support, and Customer Support/Operations teams.”

In the interview below, Armstrong shares some of the best advice and lessons she’s learned during her impressive career journey.

What’s been your most valuable career mistake?

Spreading myself too thin and trying to get my foot in the door in too many different areas  when I was just starting out in my career.  Early on, I was put in a unique position with a lot of opportunity, and I wasn’t sure which path I wanted to take. When it came down to it, I was indecisive and wanted to maintain as much opportunity as possible versus focusing and excelling in one area. For that reason, when I decided to make a move, other and more focused individuals landed the open roles. 

Longterm, I was fortunate that those roles didn’t pan out. Because of my hard work, a peer referred me to my next role, which was an absolutely amazing experience. That said, from this experience, I learned to be more decisive on my career path and to commit and stay focused. Picking one option and potentially missing out on alternative opportunities is ultimately always going to be better than spreading yourself too thin.

What’s something at work that you’re especially good at?

Not to toot my own horn, but one thing I’m incredibly proud of and what brings me great joy has always been helping folks develop their careers. Whether it's helping someone figure out where they want to be or how to get there, it’s why I love my job. I love strategy and applying it to operations or our customer experience — but I especially love it when I can apply it to building a successful career path that helps the company and a member of my team achieve their goals.

What about outside of work? 

I like to think I’m pretty skilled on the slopes. I’ve been skiing since my grandpa taught me when I was four years old. Just like helping folks build their careers, it’s easy to be good at something you love doing!

What are you trying to improve on? 

I’m always looking to improve my technical skills! We have an incredible Data and Engineering team at GlossGenius who supports us in so many ways, but I’m excited to level up here. I love exploring datasets to better understand a problem. I’ve come a long way in this area over the years, but I know there is so much more to learn. I’m so fortunate to be at a company with peers who not only support me in these efforts everyday but are happy to help me succeed here. 

Managing people — especially if you’re new to it — is not easy. How has GlossGenius helped set you up for success? How is this kind of support reflective of the overall culture at GlossGenius? 

I’ve been managing teams for over eight years now, every person is different and there is always something new to learn. At GlossGenius, we have an incredible People team who have  set up some amazing processes. For example, we have a monthly managers meeting where different techniques and strategies are shared, and it also serves as a space for managers to discuss challenges, successes, and to support one another. I love being able to connect with and learn from so many talented colleagues. I think these efforts speak to our culture and our mission to make others successful. 



Fairygodboss is proud to partner with GlossGenius. Find a job there today!

Why women love us:

  • Daily articles on career topics
  • Jobs at companies dedicated to hiring more women
  • Advice and support from an authentic community
  • Events that help you level up in your career
  • Free membership, always