This SVP’s ‘Powerful Combination’ for Success: Humility, Empathy, Avoiding Self Limiting and More

Sponsored by Prudential Financial

Jess Gillespie

Photo courtesy of Prudential Financial.

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May 22, 2024 at 6:12AM UTC

Jess Gillespie, senior vice president and head of distribution for Prudential Group Insurance at Prudential Financial, leads a national team that helps mid-sized and large employers across the country bring their employees the financial wellness education, solutions and tools they need to achieve better financial outcomes.

Gillespie’s been with the company since 2006, in her current role for three years, and also serves on the Women Empowered business resource group board of directors. 

“My day-to-day is never the same, and that’s why I absolutely love my job,” she tells Fairygodboss. “I not only have the great fortune to lead and work with an incredible distribution organization, but  also sit on the Strategic Leadership Team (SLT) for the Prudential Group Insurance U.S. Business Division.”

Her days are a blend of development and execution on strategic deliverables, collaborating with the organization and partners across the company to execute on the needs and expectations of the markets Prudential Financial serves and meaningfully focuses on the company’s diversity, equity, and inclusion work.

“Having the ability to interact with our customers, brokers and consultants on a regular basis is truly rewarding,” she says. “It keeps me focused on ensuring we place our customers’ needs and experiences at the core of everything we do. And, Prudential’s focus on DE&I allows us to create an environment that supports employees regardless of race, gender, age, or background.”

 Here, we caught up with her to learn more about what her role looks like, her tips for working from home as well as the best advice she’s received throughout her career.

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

To never self-limit. Unfortunately, as women, we have a tendency to want to be “totally prepared” and ready for that next step before we take it. A former boss literally rolled his eyes at me and told me that I was shortchanging myself when I was contemplating not taking a bigger role that felt like a stretch in a number of ways — personally and professionally. He didn’t do this in a condescending way at all, and it was at that moment that I realized I was the one putting boundaries on myself that were self-limiting.

I decided, after a fairly robust conversation with my boss, that I was going to put myself out there, I was going to take more risks and I wouldn’t apologize for not knowing every nuance of the job.

Humility, empathy, being a continuous learner, hard work and perseverance are the recipe to success in my view. These traits, coupled with the willingness to take risks and not self-limit, can be a pretty powerful combination. This doesn’t mean you won’t fail at times, but it means you will be able to get back up stronger and go after it again.

How does Prudential help support work-life balance?

I came to Prudential for one main reason — the culture. I previously worked in an environment where I, unfortunately, did not see a path forward for advancing my career and raising a family — two things I wanted to achieve and certainly hoped didn’t have to be mutually exclusive.

I feel incredibly thankful to Prudential for the support they provide employees. I was able to enter the organization with a limited scope of responsibility and create departments and meaningful work outputs that had not previously existed, all while growing into the position I currently hold. I have been able to balance my work responsibilities and raise two children who are the center of my world. 

Photo courtesy of Prudential Financial.

 Prudential’s flexibility to work remotely (even before the pandemic), parental leave policies, business resource groups and many other wonderful programs, help employees achieve the balance needed to grow personally and professionally. I would be lying if there weren't days or weeks where the balance of all of life’s responsibilities just feel plain hard. But, at the end of the day, I know I am surrounded by a company that cares about their employees as human beings and does the right thing for their people.  

Outside of your work, how do you “check out” and focus on your personal life? And how does your company support you in doing this?

As a bit of a Type A personality, I have to remind myself that “checking out” needs to happen. While the pandemic brought an incredible amount of challenges, it had silver linings for me, too. Not having to travel allowed me to get a more disciplined routine around “checking out.” I got back into exercising on a more regular basis, going out for hikes on the weekend and getting back to the ski slopes during the winter months.

And now that the pandemic is easing, I am back to many of the things I love to do like attending concerts, shows, eating out and traveling for pleasure. Prudential provides a generous paid time off program in addition to giving employees time to give back through volunteer hours. Being able to take time to serve my community with my children is always incredibly rewarding.

Switching gears to remote working, could you describe Prudential’s hybrid/remote work policies? How do these policies positively impact employees?

Prudential is excelling in this space. The company has put the safety of their employees and families at the center of all decisions since the pandemic began. The ability to work remote, and ease back into the office, has given employees peace of mind. Most roles in the company have been deemed either fully remote or hybrid, with few roles requiring the need to be onsite at a physical location five days a week. This flexibility gives employees the option to work from different locations, as well as achieve greater work-life balance by not having to commute into the office each workday.

Photo courtesy of Prudential Financial.

How do you manage to avoid burnout while working in a hybrid/remote environment?

You have to force yourself to walk away, to get outside for those 30 minutes, or whatever you need to re-center and re-balance. It is hard to be your best self personally or professionally if you are not taking care of your own well-being.

The pandemic has taken a disproportionate toll on women in the workplace, which is incredibly unfortunate. I know I personally felt the strain of working a demanding job, being the parent who was working at home along with two children who were also remote learning and dealing with aging parents — one who became incredibly ill and hospitalized after contracting COVID-19. It can be really hard, but you have to step away. And if you feel as if you can’t, or it becomes too overwhelming, you need to ask for help and know that it is not a sign of weakness but rather strength and care for your own mental well-being.

Overall, what are your top 1-5 tips for excelling in a hybrid/remote job?

  1. Be reachable and communicative. In the new world of hybrid work, we need to rethink how we communicate with our teams. Being reachable and utilizing multiple forms of communication — video, phone, text chats, etc. will be key.

  2. Invest in team building. Team building is even more important in a hybrid or remote work model, where it’s not always possible to stop by someone’s desk. That’s why it’s critical to encourage employees to collaborate in order to foster innovation in large and small forums. And, where possible, scheduling team-building activities outside of work will be very important. 

  3. Establish a consistent schedule. In a hybrid or remote workplace, you need to think of ways to maximize your performance and determine which activities are best accomplished at home versus the office. If fully remote, dedicating time to creating a consistent schedule, particularly around engagement, will be critical.

  4. Create healthy boundaries. If you are working from home, it is not realistic to expect that you will be sitting at your desk for eight straight hours. Instead, take regular breaks throughout the day. Set a regular start and end time to your day and discuss boundaries around evenings and weekends. Establishing these boundaries will make you more productive and prevent you from burning out.

  5. Focus on outcomes. Work is not measured purely in hours. Instead, focus on outcomes. Promote transparency around how people use their time and flexibility in how work gets done. This reinforces that team member participation is judged by contribution rather than location.

Looking ahead, what do you see as the future of work?

I see the future of work holding more autonomy, flexibility, and fulfillment for workers. Companies with strong ethical and social standards, fair pay and work-life balance will be those that attract and retain the best talent. And, the skills employees need will continue to evolve, providing companies with yet another opportunity to grow, develop and upskill their workforce.

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