He made his international debut in the 2002 PSA World Tour for Zimbabwe. He also went on to represent Zimbabwe at the 2002 Commonwealth Games and competed in the Men's singles and Men's doubles squash events. He later moved to South Africa and competed for South Africa in international level including the 2007 Men's World Team Squash Championships, 2008 Men's British Open Squash Championship and 2009 Men's World Team Squash Championships as a part of 2009 PSA World Tour. Jesse retired from professional squash career in 2010 and started his coaching career soon after his retirement. He is currently residing in England and has been running a Squash Academy called Jengelbrecht.