Dudley qualified as a member of the Institute of Chartered Accountants in England and Wales in 1975. In 1977, he emigrated to Bermuda to join Arthur Morris with particular responsibility for the service of international clients.

Dudley's 30+ years in public practice have afforded a wide range of experience in providing specialist services, including appointments as director and trustee, to a diverse portfolio of major clients.

Along with Arthur Morris, Dudley is also a partner in a practice in the Turks and Caicos Islands and his current professional and charitable activities include:
• Past member of the Council of the Institute of Chartered Accountants of Bermuda (ICAB).
• Member of the Society of Trust and Estate Practitioners.
• Fellow of the Institute of Directors.
• Member and a past president of Hamilton Lions Club.
• Chairman of Windreach Bermuda.