St Leonards has a commercial centre that complements the role of Chatswood, Lane Cove and North Sydney as one of the centres for business on the North Shore of Sydney. St Leonards contains one of Sydney's suburban skyscraper clusters, with major offices for many large companies including Toyota Financial Services, IBM, Lenovo, Oporto Chicken & Burgers, Manchester Unity, 3, Savvytel, CIMIC Group, Forum Group, Macquarie Radio Network and Channel 31 TV studio. The NSW Department of Education and Training host their Information Technology Directorate in Herbert Street. Gore Hill Technology Park is the site of current Fox Sports television studios.
St Leonards has developed into somewhat of a home for rugby union with the former headquarters of the Australian Rugby Union located at St Leonards (2007-2018), from neighbouring North Sydney. The Northern Suburbs Rugby Club has its clubhouse in St Leonards, featuring the Cabana Bar and Lounge. It also has a popular Rock Climbing Facility for the climbing community.