How to Navigate a Career Pivot, According to a Senior Director Who Did

Leila Gilbert, Senior Director of Product Management at UKG, first tapped into the technologies that ultimately pivoted her career path when she transitioned from in-store customer service roles at a New England grocer to a position at the head office in the Labor and Operations department. 

“That role was my first experience seeing how technology can positively impact both operations and employees,” she says. “This experience played a key role in helping me successfully transition to a software vendor environment.”

Gilbert learned a lot by bouncing between software upgrade support for retail stores and handling retail operations, traveling extensively for work. She ultimately transitioned from retail services to the product side for several reasons: a curiosity to explore a new facet of business and a better work-life balance as a single mom with two active, athletic kids. 

She has worked in product management ever since. At UKG, she is currently involved in the development of a brand-new product solution, which, she says, comes with its challenges—she enjoys helping the team navigate around the obstacles and find paths to success. 

Here, she shares how she made the switch and the support UKG offered her along the way.

How did you make this switch, and how did UKG support you?

During my time in Services, I regularly advocated for customer needs and partnered with Product and Engineering teams to create solutions. This helped me build strong relationships within the Product organization.

As I began considering a change, I knew I wanted to stay with the company but wasn’t sure where I fit. I spoke with one of the leaders about potential opportunities in Product. He was incredibly supportive and connected me with a few other leaders. Thanks to the support of both my service manager and the new Product leader, the transition was smooth.

How have you benefited from the skills and experiences gained through your career pivot?

One of the most important things I bring to my current role is empathy. I’ve been in the shoes of our customers, and I haven’t forgotten what that feels like.

Another key skill I’ve developed is negotiation. Whether it’s securing support from another team or helping someone else advance their goals, negotiation plays a role in my day-to-day work. Having been a user of the software I now help design has given me a unique and valuable perspective. 

What do you find most rewarding and most challenging about your work?

The most rewarding part of my work is seeing our customers succeed using our software. On the other hand, one of the most challenging aspects is making business and product prioritization decisions. It’s a balancing act—and one where data plays a critical role. 

What’s your favorite thing about working at UKG?

Without question, my favorite thing about working at UKG is the people. I genuinely enjoy working with such a well-rounded and talented group at UKG, as well as with our customers. I also find it deeply rewarding to build solutions that help businesses thrive.  

Looking back, what’s been your most valuable career lesson?

One of the most valuable career lessons I’ve learned was not to second-guess my instincts. In the past, especially when stepping into new roles, I’ve doubted myself or held back. Over time, I learned to trust my gut and lean into my initial reactions; they’re often right.  

What advice would you give to women considering a career pivot?

Talk about it. Share what you’re thinking with colleagues and friends. Opening up and asking for input was one of the best decisions I made. People are often more willing to support your journey than you might expect. The key is to be clear and intentional about your goals. Once you are, new opportunities start to surface. 

 Interested in joining the UKG team? They’re hiring! Click the link below to browse opportunities. 

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