Jessica Bass Bolander – 20 Under 40

Lockton Dunning Benefits
39 | Education: Westminster College

As vice president at Lockton Dunning Benefits, Jessica Bass Bolander has spent the last two years helping clients navigate the COVID-19 pandemic.

Lockton Dunning Benefits specializes in the design, implementation, communication, and year-round service of medical, dental, life, disability, and other employer-sponsored benefit programs.

“​​The last 24 months have been extremely challenging for businesses in our community. At Lockton Dunning, we helped clients deploy return-to-work strategies that kept their businesses open and, more importantly, their employees safe,” Bass Bolander said. “Now we’re helping clients modify their employee benefit perks and rewards programs to compete in a post-pandemic labor market.”

Her company is also involved with the corporate work-study program of Cristo Rey Dallas College Prep, a Catholic college preparatory school for students from low to moderate-income households.

“I’ve had the privilege of mentoring a young man who would like to study engineering and be the first in his home to attend college,” Bass Bolander said. “It has been an incredible honor to meet with the students in our Lockton Dunning/Cristo Rey work-study program, and I know these students will become future leaders of our community.”

The mother of two co-chaired the Armstrong Bradfield Preschool Association Home Tour in 2019 and will chair the Bradfield auction next year. 

Toughest business/personal challenge?

Going back to work after my kids were born. I remember giving myself pep talks on the way to work, reminding myself that I’m a better mom and wife because I have my career. It was brutal leaving small babies at home and dragging a breast pump to every client meeting or work trip, but fortunately, I had the most amazing support system.

Where do you see yourself and/or your career 10 years from now?

Learning and growing and hopefully inspiring the next generation of female leaders to stay in the workforce. As an example, it’s been amazing to work with my clients on enhancing their parental leave policies to give working parents more time off post-baby. I’m excited about where the future is going for working parents and believe our business community is stronger when women thrive in the workplace.

Fun fact that someone wouldn’t know about you?

I can play the French horn. My parents made us play an instrument, and now I’m making my kids find their own musical interests. My 7-year-old takes DJ Lessons with DJ Soulja, and he is now learning to play the piano.

What was your first job and what did you learn from it?

My first job was bussing tables at local a restaurant in San Antonio. Working in the restaurant industry taught me invaluable lessons about customer service and teamwork. These are skills that have made me a better consultant and colleague in my current role at Lockton Dunning. Our firm has a motto “We Live Service” and it’s a virtue we all live by with our clients and colleagues.

Which leadership skills were the most challenging for you to develop and why?

Delegating! I’m a perfectionist and it’s hard for me to let go of certain parts of my job. Luckily when you work with some of the smartest people in your industry it’s easier to let go. 

If you could buy a book (or rent a movie) for your neighbor, what would it be and why?

Start with Why by Simon Sinek – I read this for a leadership development class and I believe the core message about coming from a place of curiosity rather than assumption can be applied to everyday life.

What is your favorite local store?

I love to support locally owned female businesses – Canary, Ellis-Hill, Empire Bakery, and Hip Hip Hooray are my local favorites. 

How do you motivate others?

Be honest and vulnerable – I’ve found that the most inspiring mentors are the ones who speak from the heart.  If you own your mistakes or insecurities, you can open up an honest dialogue about growth and development.

What would you tell an 18-year-old you?

Not everyone will like you and that’s OK. Early in my career, I spent so much time worrying about office politics and I was nervous that I might say the wrong thing in an email. I’ve had wonderful mentors throughout my career who reminded me to be confident and authentic.

Fun fact that someone wouldn’t know about you?

I can play the French Horn. My parents made us play an instrument and now I’m making my kids find their own musical interests. My 7-year-old takes DJ Lessons with DJ Soulja and he is now learning to play the Piano.

What’s on your bucket list?

The Great Wall of China

Rachel Snyder

Rachel Snyder, deputy editor at People Newspapers, joined the staff in 2019, returning to her native Dallas-Fort Worth after starting her career at community newspapers in Oklahoma. One of her stories won first place in its category in the Oklahoma Press Association’s Better Newspaper Contest in 2018. She’s a fan of puns and community journalism, not necessarily in that order. You can reach her at [email protected]

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