A product of the MRF Pace Foundation under the mentorship of Dennis Lillee, Kenny got selected into the Indian ODI cricket team after an exception haul of 10 wickets in an Irani Trophy match for Rest of India against Karnataka in the 1999/2000 domestic season. He was later picked for the Australian tour where he picked 5 wickets in the first-class game prior to the first Test. He joined the Indian Cricket League during its inception in 2007 and was one of the stand-out performers for the Chennai Superstars. He was the head coach of the USA cricket team during the ICC Division 3 tournament held at Bermuda and is the current USA under 19 coach. Kenny heads the operations of the academy and is the chief coach of TCA.