Westley previously worked at
Rushden & Diamonds,
Ipswich Town,
Charlton Athletic,
Luton Town and
Derby County. At these clubs he was responsible for developing young players, who included
Matthew Upson,
Kieron Dyer,
Richard Wright,
Titus Bramble and
Kevin Lisbie. At Derby, he oversaw the development of young stars such as
Tom Huddlestone,
Lee Holmes,
Giles Barnes,
Lewin Nyatanga and
Miles Addison. Westley took the helm at
Luton Town in July 1995 after the departure of
David Pleat. He saw out the
1994–95 football season with
Luton Town finishing 16th in Division 1. The following season did not get off to a good start and Westley was sacked after a 0–4 defeat at
Portsmouth. Westley was made
caretaker manager of Derby County in January 2006 following the departure of
Phil Brown. He lost his first game in charge 1–0 at home to
Sheffield United and despite not managing a win in four further outings, was made manager until the end of the season. His first victory was a 1–0 home win over
Plymouth Argyle just two days later. Despite achieving his objective of keeping the club in the
Championship by the end of the season he was not offered the job of permanent manager, instead being replaced by
Billy Davies. He joined
Birmingham City as director of their
youth academy in 2006. In his first season, he led the under-18 side to the quarter-final of the
FA Youth Cup, and two years later they reached the semi-final of the same competition. After completing a report to the club's board of directors, which contained recommendations needed to "push [the Academy] to the next level", Westley left the club by mutual consent in February 2011. In July 2014 Westley became academy director at West Ham United, replacing long-term incumbent,
Tony Carr. ==Performance by club==