Originally from Wallaceburg, Ontario, Canada, Brigadier General Whale enrolled in the Canadian Armed Forces in 1986. Achieving Royal Canadian Air Force pilot's wings in 1990, he has accumulated flight qualifications and experience on Kiowa, Twin Huey, Griffon and Apache helicopters delivering tactical aviation mobility, reconnaissance and aerial firepower effects to Joint warfighers. In 2017 he began a transition to space domain force development, readiness and operations.

His staff experience includes Training and Concept Development at Wing level, Defence Academy Chief of Staff, and strategic level positions at National Defence Headquarters including Canadian Forces Transformation Team, Director of Air Strategic Plans, Acting Director General Air Readiness, Special Advisor to the Minister of National Defence and Director General for Space.

Brigadier General Whale's command roles have included US Army Aviation Attack Platoon Leader, Battalion Battle Captain, Squadron Deputy Commanding Officer, Special Operations Aviation Squadron Commanding Officer, Royal Canadian Air Force Wing Commander and Joint Force Space Component Commander. Brigadier General Whale’s current role is Deputy Commanding General – Transformation, Space Operations Headquarters, United States Space Force.