Job Description
Senior Project Manager – Digital Migration (Client Rollout)
A great opportunity in the insurance industry to lead a large digital rollout impacting thousands of clients. Play a key role in planning, coordination, and delivery while working with multiple teams in a dynamic and collaborative environment.
What is in it for you:
Hourly salary of $110-120, based on experience.
Incorporated Business Rate: $128-138 per hour.
Full-time position: 37.50 hours per week.
The mandate is planned for an 18-month duration.
The role is hybrid and requires 1 day per week in-office in Toronto.
Responsibilities:
Lead the end-to-end planning, coordination, and execution of a large-scale digital client rollout impacting approximately 17,000 users.
Develop and manage a comprehensive migration strategy, including roadmap, sequencing, readiness criteria, and decision checkpoints.
Oversee execution by coordinating cross-functional teams across technology, operations, client experience, communications, and external partners.
Establish governance frameworks, including standardized tools, playbooks, and escalation paths.
Manage integrated project plans, including Gantt charts, dependency tracking, milestones, and RAID logs with proactive mitigation strategies.
Deliver clear, concise executive reporting on progress, risks, and key decisions.
Align rollout activities with change management and communication strategies to support adoption and readiness.
Ensure compliance with quality, security, accessibility, and regulatory standards.
Identify and mitigate risks affecting client experience, including data integrity and process transitions.
Drive continuous improvement through post-migration reviews and lessons learned.
What you will need to succeed:
Bachelor’s degree in business, technology, or a related field.
PMP, PMI, or SAFe certification is considered an asset.
8 years of experience leading large-scale transformation, migration, or implementation initiatives.
Proven expertise in program planning, Gantt scheduling, RAID management, and executive-level reporting.
Demonstrated ability to lead both business and technology-driven initiatives.
Experience working in regulated environments such as insurance or financial services.
Strong leadership skills with experience managing cross-functional and matrixed teams.
Excellent communication and stakeholder management skills with the ability to influence at all organizational levels.
Strong analytical thinking and problem-solving capabilities in complex project environments.
Ability to adapt quickly, manage competing priorities, and operate effectively in changing conditions.
Familiarity with digital platform or portal migrations and client experience best practices.
Knowledge of change management principles and adoption strategies.
Why Recruit Action?
Recruit Action (agency permit: AP-2504511) provides recruitment services through quality support and a personalized approach. As part of the screening process, some applications may be reviewed using artificial intelligence tools. Only candidates who meet the hiring criteria will be contacted.
# MFCJP0001XXXXXX
Job Types: Full-time, Fixed term contract
Contract length: 18 months
Pay: $110.00-$138.00 per hour
Benefits:
Work from home
Application question(s):
This position is hybrid and requires 1 day per week in-office in Toronto. Are you comfortable with this requirement?
Do you have a Bachelor’s degree in a business or technical field? If yes, please specify.
Education:
Bachelor's Degree (required)
Experience:
Regulated environments (financial services or insurance): 2 years (preferred)
Digital platform/Portal migrations (benefits/disability): 2 years (preferred)
Change management and adoption: 2 years (preferred)
Operating within or establishing a PMO model: 2 years (preferred)
Leading large-scale transformation initiatives: 8 years (required)
Program planning, scheduling, and reporting: 5 years (required)
Leading agile delivery: 5 years (required)
Delivering tech and business projects: 5 years (required)
Licence/Certification:
SAFe certification (preferred)
PMP or PMI certification (preferred)
Work Location: Hybrid remote in Toronto, ON M4W 1E6
A great opportunity in the insurance industry to lead a large digital rollout impacting thousands of clients. Play a key role in planning, coordination, and delivery while working with multiple teams in a dynamic and collaborative environment.
What is in it for you:
Hourly salary of $110-120, based on experience.
Incorporated Business Rate: $128-138 per hour.
Full-time position: 37.50 hours per week.
The mandate is planned for an 18-month duration.
The role is hybrid and requires 1 day per week in-office in Toronto.
Responsibilities:
Lead the end-to-end planning, coordination, and execution of a large-scale digital client rollout impacting approximately 17,000 users.
Develop and manage a comprehensive migration strategy, including roadmap, sequencing, readiness criteria, and decision checkpoints.
Oversee execution by coordinating cross-functional teams across technology, operations, client experience, communications, and external partners.
Establish governance frameworks, including standardized tools, playbooks, and escalation paths.
Manage integrated project plans, including Gantt charts, dependency tracking, milestones, and RAID logs with proactive mitigation strategies.
Deliver clear, concise executive reporting on progress, risks, and key decisions.
Align rollout activities with change management and communication strategies to support adoption and readiness.
Ensure compliance with quality, security, accessibility, and regulatory standards.
Identify and mitigate risks affecting client experience, including data integrity and process transitions.
Drive continuous improvement through post-migration reviews and lessons learned.
What you will need to succeed:
Bachelor’s degree in business, technology, or a related field.
PMP, PMI, or SAFe certification is considered an asset.
8 years of experience leading large-scale transformation, migration, or implementation initiatives.
Proven expertise in program planning, Gantt scheduling, RAID management, and executive-level reporting.
Demonstrated ability to lead both business and technology-driven initiatives.
Experience working in regulated environments such as insurance or financial services.
Strong leadership skills with experience managing cross-functional and matrixed teams.
Excellent communication and stakeholder management skills with the ability to influence at all organizational levels.
Strong analytical thinking and problem-solving capabilities in complex project environments.
Ability to adapt quickly, manage competing priorities, and operate effectively in changing conditions.
Familiarity with digital platform or portal migrations and client experience best practices.
Knowledge of change management principles and adoption strategies.
Why Recruit Action?
Recruit Action (agency permit: AP-2504511) provides recruitment services through quality support and a personalized approach. As part of the screening process, some applications may be reviewed using artificial intelligence tools. Only candidates who meet the hiring criteria will be contacted.
# MFCJP0001XXXXXX
Job Types: Full-time, Fixed term contract
Contract length: 18 months
Pay: $110.00-$138.00 per hour
Benefits:
Work from home
Application question(s):
This position is hybrid and requires 1 day per week in-office in Toronto. Are you comfortable with this requirement?
Do you have a Bachelor’s degree in a business or technical field? If yes, please specify.
Education:
Bachelor's Degree (required)
Experience:
Regulated environments (financial services or insurance): 2 years (preferred)
Digital platform/Portal migrations (benefits/disability): 2 years (preferred)
Change management and adoption: 2 years (preferred)
Operating within or establishing a PMO model: 2 years (preferred)
Leading large-scale transformation initiatives: 8 years (required)
Program planning, scheduling, and reporting: 5 years (required)
Leading agile delivery: 5 years (required)
Delivering tech and business projects: 5 years (required)
Licence/Certification:
SAFe certification (preferred)
PMP or PMI certification (preferred)
Work Location: Hybrid remote in Toronto, ON M4W 1E6
💡 Quick Summary
Seeking a career-building opportunity? The Senior Project Manager – Digital Migration (Client Rollout) position is now open for candidates interested in the Operations Executive Jobs sector. This role in Toronto offers a professional environment and growth potential.
Requirement Snapshot: Candidates should possess basic communication skills, a proactive attitude, and the ability to work in a team. Experience in Operations Executive Jobs is a plus.