How do I move up to roving umpire, chair umpire or referee levels?

Advanced clinics are by prerequisite. Tennis Canada's officiating clinics page lists these (no clinics were scheduled when checked):

• Roving Umpire 1: at least 10 full days at Provincial, National and/or ITF non-professional events in the past 12 months, satisfactory evaluations, and regular work as a roving umpire.
• Roving Umpire 2: at least 20 full days in the past 12 months (at least 10 at National or ITF non-professional level), satisfactory evaluations, regular roving work. Roving Umpire 2 officials train, mentor and coach less experienced officials.
• Introduction to Chair Umpiring: certification as Roving Umpire 1, regular work in that role and sound knowledge of the rules and procedures; Tennis Canada Officiating decides who is considered. After the in-class modules you must work at least three matches as chair umpire at provincial or national level.
• Chair Umpire 1: certification as a Novice Chair Umpire, at least 10 matches at Provincial, National and/or ITF non-professional events in the past 12 months, satisfactory evaluations and regular chair work.
• Referee 1: certification as Roving Umpire 2, in-depth knowledge of the rules, procedures and Code of Conduct, and invitation at the discretion of the Tennis Canada Officiating Department.
• Referee 2: at least two full tournaments as Referee at Provincial events and/or Assistant Referee at National or ITF non-professional events in the past 12 months (at least one at National or ITF non-professional level), satisfactory evaluations and regular work as a referee.

Certified officials also need to meet Tennis Canada's Officiating Recertification Requirements document, available to certified officials.