Born and raised in the heart of the Bluegrass, Jesse Caylor returned to his hometown of Lexington, Kentucky in 2018 to purchase Custom LogoWare, a then-small local business specializing in custom apparel and promotional products. Since taking the reins, Jesse has transformed the company into a growing brand that has completed over 3,000 projects, generated nearly $4 million in sales, and donated more than $25,000 to charitable causes. In 2022, Custom LogoWare became proudly certified by the National LGBT Chamber of Commerce (NGLCC).
A proud graduate of Western Kentucky University, Jesse earned his degree in Marketing and Advertising while leading campus life as President of Sigma Nu Fraternity. He was recognized as Sigma Nu Man of the Year and later Alumnus of the Year for his continued support and leadership. His marketing career has taken him coast to coast—from San Francisco’s BiRite Foodservice to the Restaurant Association of Metropolitan Washington in D.C.—before planting roots back home to grow something of his own.
Today, Jesse leads a dedicated team of account executives and designers, ensuring every client receives creative, thoughtful, and responsive service. When he's not working, you can find him at Keeneland in the fall, traveling with friends, or enjoying time with family.