Stiff played for Yorkshire at all levels, including the Academy, before Kent won the race to sign him when he penned a three-year deal with the county in December 2003.
He was handed his Kent debut at the start of the 2004 season, appearing in the opening County Championship game against Gloucestershire at Bristol.
The tall pace bowler toured Australia with England Under-17s in 2001 and with the Under-19 two years later, when he took five wickets in the first innings of the third Test in Sydney.
He was also part of the England squad for the Under-19 World Cup in Bangladesh in 2004.
He played one first-class game for Kent in 2005, in which he took two wickets, but did not feature in any of their totesport league campaign.
He left Kent at the end of 2006 and joined Leicestershire, but was released after a solitary season at Grace Road.
After a stint playing Yorkshire league cricket, Stiff was given a fourth chance on a short-term contract with Somerset for 2009.
He is due to stay until the end of May, and his position will be reviewed at the end of April.