Jaymon’s professional tennis career kicked off when he reached the juniors semi-finals at Wimbledon in 1996. 

After retiring from professional tennis, Jaymon turned to coaching. In 2018, he became part of the Australian Davis Cup coaching team. During his time as coach, the team reached the finals in 2022 and 2023, and the semi-finals in 2024. As of October 2025, Jaymon remains part of the Davis Cup coaching team.

Alongside Lleyton Hewitt, Jaymon was the national tennis men’s coach for both the Tokyo 2020 Olympics and Paris 2024 Olympics. In Tokyo, he coached John Peers and Ash Barty to the bronze medal in the mixed doubles. Then, in Paris, the team recorded its best Olympic result in 25 years with Matt Edben and John Peers winning gold in the men’s doubles.