Before establishing Milestone in Canada, Al Sibilo's career spanned twenty years and a number of progressive management & leadership roles with two major property & casualty insurance companies.

Most recently Al spent five years as the Western Regional Manager for Canada’s most prominent transportation insurer, overseeing a growing portfolio that spanned the four western provinces, and the multi-disciplined office that marketed, underwrote, settled claims for, and provided safety advice and training services to the clients within that portfolio.
As a transportation insurance & risk management specialist, Al Sibilo is also the team leader for Milestone’s trucking industry practice. He is an active member of the Alberta Motor Transport Association, and its various subgroups:
- AMTA Education Foundation
- Member Services Committee
- Annual Management Conference Committee