Jessica Underwood.

Founder & Visionary

Jessica founded Chief of Staff KC—a staffing solutions company for the modern office—in 2011. Chief of Staff focuses on placing quality candidates in today’s office cultures. The company has carved out a focus on developing a personable and approachable appeal to Kansas City’s top talent and the companies who value their people.

A Kansas City native, Jessie began her career at, and quickly joined the ranks of a top sales performer, while experiencing firsthand the new job market from its highest growth segment—online search and recruitment.

Linked In Profile

“Chief of Staff is an excellent staffing agency and provided me with immediate opportunities for employment. Tiffany has been great to work with, and she always responded—immediately—to both my concerns and questions via phone call or e-mail. I’d highly recommend any job seeker to meet with Chief of Staff!”

– Leanne H., Scheduler


Armed with a great sense of business and an earned understanding of the trends in recruitment, Jessica became an entrepreneur where she has continued to push new concepts for the job market into business operations. Chief of Staff has been named one of Kansas City’s fastest growing companies in 2015 and 2017, and Thinking Biggers Top 25 under 25 businesses in 2019.

Jessie attended high school at St. Teresa’s Academy and graduated with her Advertising degree from Marquette University. In recent years, she graduated from HEMP (Helzberg Entrepreneurial Mentorship Program) and currently serves as School Board President at St. Elizabeth Catholic School. Jessie and her husband Chris, have 6 children.

First Job:

Cashier at Eckerd Pharmacy

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Favorite workday lunch spot:

The Mixx