Board Member Bios

Gary Cain grew up in Knife River Minnesota and Braymer Missouri.  After graduating High School in Braymer, he attended the University of Missouri and received a Bachelor of Science degree with a major in Business Administration with an emphasis in Economics.  Gary is the Redistricting Project Manager for the State of Missouri.  He has also held positions as the Director of Evaluations and the Associate Registrar at Columbia College and as a post award analyst/accountant at the University of Missouri. 

Gary met his wife Melody while they both attended the University of Missouri and have been married for 24 years.  They have 2 daughters.  Claire is a Junior at the University of Missouri and Chloe is a Senior at Rock Bridge High School.  For enjoyment Gary and Melody like to spend time with friends, go to MU football games, attend concerts, and watch our daughter’s soccer games.  In the year of covid we have also been spending a lot of time outside of Columbia exploring wineries and breweries throughout Missouri.

Gary was interested in becoming a director to help provide financial responsibility to the board.  He was also interested in protecting the homeowners by making sure that the covenants are adhered too by the residents and by the board.

Brad Jessee

Brad Jessee has spent most of his professional career in manufacturing and distribution and currently works as a buyer at Environmental Dynamics in Columbia, MO. Brad and his wife Teresa returned to the Columbia area in 2006 after spending 11 years in the Chicago area and moved to Wyndham Ridge in 2014. In their free time they enjoy spending time with friends and exploring all the area has to offer.

Brad joined the board wanting to become a good steward of HOA resources and a greater compliance to the covenants for our community, as well as to promote transparency between the board and homeowners.


Herb Watchinski, Jr

A self-employed business consultant, business agent and management consultant/trainer that spent over 20 years in the Information Technology industry.  A senior executive that managed large diversified international organizations in such area as sales, marketing, ISO quality standards, business development, management leadership development, technology services, operational support, and new product/services development.

Prior to joining IBM was a commissioned Missouri State Trooper serving for the last 5 years as the Graduate Dean of the Law Enforcement Academy and as the State’s Hazardous Materials Officer and the liaison officer to the Missouri General Assembly. He has held a law enforcement commission at the city, state, federal, and international levels.

Holds degrees in Political Science, Criminal Justice Administration, and Public Administration.