Russell completed his schooling at St Ignatius College (Riverview) in November of 1983 and a few weeks later commenced his insurance career as a junior with Phoenix Prudential working in claims & underwriting and then to Royal & Sun Alliance (RSA) in 1986 when RSA purchased the Phoenix Prudential business.

After a break from the insurance industry for nearly a decade to serve in the NSW Police Force he re-joined alongside his brother Alex at Chegwyn Insurance Broking Services (CIBS) in 1998 beginning as a junior broker. In 1999 CIBS purchased the business of Bruce Craig Australia and became known as Chegwyn Craig Australia (CCA) . In 2001 CCA was purchased by Finn Foster and Associates where Russell took on the role of Account Manager until he departed to establish his own insurance brokerage under the name of Chegwyn Insurance Brokers (CIB) as Managing Director which began trading in Wetherill Park in February of 2005.

The CIB business grew steadily and in 2013 an offer was made by AEI to purchase the business and for Russell to buy equity and become a shareholder and director. In 2022 Russell remains a director and equity shareholder in AEI Insurance Broking Group and his current role is overseeing the day to day operations of the Oran Park branch of AEI as well as providing assistance to the operations of other branches.

When not at work Russell has a passion for playing golf and spending time gardening as well as being a lifetime supporter of the Manly Sea Eagles rugby league football club.