Dennis Charley began working at Lawe Insurance Brokers in 2005 where he is a major shareholder and serves as the Company Secretary to this day. He also holds the prestigious role of Life Member at the Million Dollar Round Table. His career has had him serve as the President of LOJ Managers & General Agents Association from 1982 to 1984 and as the Branch Manager at the Life of Jamaica from 1978 - 1997. 

Dennis Charley is a past student of St. George's College and was involved in athletics, namely football, karate and track and field. He played Manning Cup Football from 1960 - 1962 and was the winner of the Champs Class-1 4x100 Relay Team Winner in 1962. He also holds a 4th Degree Black Belt at the Jamaica Seido Karate Organization from 1985 - 2017 and is an enthusiastic golfer.