Garrett M. Webster, Sr.

It has been said that “good is the enemy of great”. Maximizing and enhancing systems is this leader’s super-power. Garrett M. Webster, Sr. continually asks the question, “How can we do it better?”

Garrett is a native of Hartford, Connecticut, but considers Kansas City his home for three decades. His leadership opens doors for students and families to access quality education and sets the stage to prepare for college, career and life. Garrett is the former Director of Admissions for Kansas City Public Schools (KCPS), a transition agent for college and career and a respected community connector. He revolutionized the KCPS enrollment process by transforming the paper system to an online enrollment system. This system enhancement streamlined enrollment for families and increased applications by 260%. Garrett’s efforts have strengthened the community’s trust in the public-school system.

I am excited to join the Youth Guidance team and partner with the Hickman Mills School District to serve our youth and our community.

Garrett’s career began in corporate with Norwest Bank as a mortgage review specialist during the height of the refinancing boom. His attention to detail allowed him to transition to join the real estate team at Sprint. Garrett’s charisma and natural ability to connect with people allowed him to excel. These skills earned him positions in companies as a Director of Marketing, Vice President of Marketing and eventually sparked his entrepreneurial spirit, launching a successful marketing company and real estate investment company.

It was not enough for Garrett’s real passion is empowering youth. This passion stems from his experiences as a teen. In the beginning of his career, Garrett served as an in-school tutor and teacher. He later created and served in a college advisor role in a Kansas City charter school. He went on to continue serving students as the Assistant Director of Admissions for Brown Mackie College. He soon realized that students needed his help before their college start. So Garrett took his talents to the YMCA to serve as the Young Achievers Director. There he served students from 54 schools (grades 7-12) in six different counties across Missouri and Kansas. Garrett is credited with helping hundreds of students tap into their inner strength, gain exposure to college and careers  — garnering more than $4 million in college scholarships.

Garrett holds a bachelor’s degree in Business Operations from DeVry University. He was appointed to the Kansas City Mayor’s Youth Commission in 2015. He earned the Pace Setter award for fund development in 2014, 2015, and 2016. He also earned the Eagle award for leading in fund development in 2015 and 2016. Garrett has a passion for people, purpose and process. Currently, he serves on the Development and Marketing committee for the American Jazz Museum. He also serves on the Board of Directors for the Citadel Homeowners Association. In his spare time, he enjoys a relaxing round of golf or a day at Kauffman stadium watching his Royals with the family. Garrett is husband and father of two amazing children.