Jessica Williams was born and raised in Oshkosh, Wisconsin. Her parents, Paul “Coot” Williams, a retired firefighter from Appleton and now the Owner and CEO of Coots Lures, and Kathy Williams, a former Food Service Director for the Unified Catholic Schools in Oshkosh, raised Jessica and her younger brother, Aaron Williams, with strong values around community, family, and service. Aaron is married to Jordan, and together they have a little boy named Ashton—one of four godchildren Jessica is proud to have. They are currently expecting a baby girl in September. Aaron manages social media for Coots Lures, in addition to running his own business, Watch Williams Media LLC, where he oversees social media strategies for a range of clients.
Growing up, Jessica and Aaron were heavily involved in sports, volunteer work, campus ministry, 4-H, choir, band, clubs, traveling, and hosting foreign exchange students and community get-togethers. Their parents' five-acre hobby farm was the setting for broom hockey, Halloween parties, Thanksgiving feasts, pool days, and Hawaiian-themed celebrations. These experiences helped shape Jessica’s love for themed events and her outgoing personality, sparking her passion for connecting with people from all walks of life.
Jessica is a 2006 graduate of Oshkosh Lourdes Academy and earned a Bachelor of Arts (BA) in Professional Communications from Alverno College in Milwaukee in 2009. During her time at Alverno, she served in a variety of leadership roles, including Community Advisor, Secretary Assistant for Academic Affairs, Peer Advisor, Admissions Ambassador, and Program Manager for Alumnae in Training. In these positions, she organized educational and social events, including the Miss Alverno Pageant, Powder Puff Football, and Homecoming marketing efforts, all while honing her skills in public speaking, event planning, and community engagement.
Her early career experiences included internships as a Summer Event Coordinator at the Leach Amphitheater (via the Oshkosh Convention and Visitors Bureau), where she coordinated a city-wide family event featuring The Chinese Acrobats and a circus band with no budget or team. She also interned in fundraising at Appleton’s Children’s Hospital and worked as a Photographer Assistant and Campus Ministry Assistant, serving as a retreat counselor for the 30-Day Famine.
After graduation, Jessica began working at the Wisconsin Challenge Academy in Fort McCoy as an Admissions Counselor, mentoring at-risk youth in a structured quasi-military environment. Inspired by the connection she formed with the Cadets, Jessica enlisted in the Army Reserves on October 5, 2011.
As a Non-Commissioned Officer (NCO) in the U.S. Army Reserves, Jessica served in Human Resources, Postal Operations, and as a Career Counselor. Rising to the rank of Staff Sergeant (SSG), she managed 50–100 Soldiers monthly, maintaining records, improving Soldier readiness, and boosting morale. She also served in leadership and support roles such as Family Readiness Group Representative, Color Guard member, Military Ball MC, Suicide Prevention Leader, and was named 2015 Best Warrior Runner-Up. She also pursued her MBA and MPA while volunteering for causes like Juvenile Diabetes, Multiple Sclerosis, and Leukemia and Lymphoma.
Following her time at the Challenge Academy and active military service, Jessica worked in veteran employment and education through various state programs. She was the Job Connection Education Program (JCEP) Manager for the National Guard’s WERC Program and later promoted to serve as Statewide Veterans Field Representative for the Wisconsin Department of Veterans Affairs. There, she championed veteran employment, post-secondary education, and entrepreneurship, co-leading the Mission Wisconsin: It’s More You! campaign, and reviewing non-profit and entrepreneurship grants.
Jessica has also taught English abroad in Fukuoka, Japan through USA Summer Camp, coordinated training with the Wisconsin Department of Workforce Development, served as a Business Representative for Oshkosh Defense, Executive Project Manager for Bug Tussel Wireless, Medical Assistant II during COVID for UW-Oshkosh, and an Apprenticeship Navigator for Wisconsin’s Bureau of Apprenticeship Standards.
Her adventurous spirit has taken her to all 50 U.S. states and 15 countries, with highlights like surfing in New Zealand, dancing at a Mardi Gras ball in Alabama, sleeping in unique hostels, and dining in Hobbiton. She enjoys hosting themed parties—Murder Mystery, Glitz & Glam, Christmas Around the World, Packers, Game Nights—and continues to give back to the community by volunteering, helping veterans with resumes, promoting local businesses, and hosting traveling nurses in her home.
When asked how all of this led to founding Whimsical Celebrations, Jessica answers:
“That’s easy—every job I had, I was the one coordinating, planning, and executing this or that event. Now, I get to help elevate life’s special moments as a woman veteran small business owner in Wisconsin.”
