Born in Bristol before moving to the village of Corfe Mullen in Dorset, Webley had been educated at King's College, a boarding school in Taunton, Somerset.
In 2001, Webley was selected to represent the Somerset Cricket Board in the 2001 Cheltenham & Gloucester Trophy and as a result he made his debut in List A cricket against Wales Minor Counties, following this up the next season with his second List A appearance, which was to be the last of his career, against Cornwall in the 1st round of the 2003 Cheltenham & Gloucester Trophy which was held in 2002.
Two matches later he scored a maiden century against Northamptonshire, making a cautious 104 before being dismissed by Monty Panesar.
[1] As a result, he made his debut for first XI in that seasons County Championship against Durham at the Riverside Ground.
In a fairly unsuccessful debut, he was dismissed for 6 in Somerset's first-innings by Vince Wells and for a duck in their second by Shoaib Akhtar.