Job Description
Date: Mar 25, 2026
Location: Winnipeg, MB (Hybrid), CA
North York - Toronto, ON (Hybr, CA
Montreal, QC (Hybrid), CA
Edmonton, AB (Hybrid), CA
Moncton, NB (Hybrid), CA
Dartmouth, NS (Hybrid), CA
Vancouver, BC (Hybrid), CA
Ottawa, ON (Hybrid), CA
Calgary, AB (Hybrid), CA
Kitchener, ON (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 9805
Employment Type: Existing Role
Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is English.
Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan.
The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $140,000 - $180,000. Candidates with salary expectations outside of the range are still encouraged to apply.
About Us
At Wawanesa, we offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS.
The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,300 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit wawanesa.com.
We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.
Job Overview
The Manager, Portfolio Delivery, leads a team of project professionals to deliver large strategic change through the development and continuous improvement of project management capabilities across the enterprise. This role ensures consistent, high-quality delivery of strategic initiatives by embedding best practices, driving strategic alignment, and enabling benefits realization. The Manager plays a key role in maturing the EPMO’s delivery model and fostering a culture of accountability, transparency, and continuous learning.
Job Responsibilities
Lead the Project Management Centre of Excellence by enhancing practices, standards, and tools with a continuous improvement mindset in alignment with enterprise strategy.
Lead a team of Project Managers, providing coaching, performance feedback, and professional development to build delivery excellence.
Collaborate with Portfolio Planning to ensure alignment between intake, prioritization, and execution processes.
Support the development and implementation of value architecture, including KPIs and success measures, to track benefits realization.
Conduct regular health checks and audits to ensure conformance to project management standards and identify opportunities for improvement.
Lead project management training and coaching initiatives across the organization to build enterprise-wide capability.
Drive project readiness including all necessary resources and processes in preparation for project launch.
Partner with Enterprise Portfolio Change to integrate change strategies into project delivery.
Contribute to strategic planning cycles by providing insights on delivery capacity, resource planning, and capability readiness.
Represent the Project Management Centre of Excellence PM COE in governance forums and contribute to the development of governance materials.
Advanced proficiency in BI tools (e.g., Tableau, Power BI), data analysis software (e.g., SQL, Python), and Excel.
Ensure consistent application of project management methodologies (e.g., PMI, Agile, SAFe) and tools (e.g., JIRA, Confluence, SharePoint).
Leads Scientific Research & Experimental Development program.
Perform other duties as assigned.
Qualifications
Bachelor’s degree in business administration, computer science, information systems, or a related field; equivalent experience considered.
Formal program/project management training from a recognized college/university.
Project Management certification and or Agile certification desired, PMP (Project Management Professional), PgMP (Program Management Professional) , ACP (Agile Certified Practitioner), CSM (Certified Scrum Master).
10+ years of progressive experience in project/program management, including leadership roles within a PMO or EPMO.
Proven experience leading and coaching high-performing project teams.
Deep knowledge of project management and agile delivery methodologies; PMP and/or Certified Scrum Master preferred.
Advanced proficiency in BI tools (e.g., Tableau, Power BI), data analysis software (e.g., SQL, Python), and Excel.
Strong understanding of portfolio management, benefits realization, and strategic execution frameworks.
Demonstrated ability to influence across business and communicate effectively with senior leadership.
Demonstrated knowledge of Canada Revenue Agency’s Scientific Research & Experimental Development program.
Knowledge of the Property & Casualty Insurance industry is considered an asset.
Insurance Professional designation is considered an asset (CIP, GIE, FCIP).
Understanding and formal training in the SAFe framework considered an asset.
Certification in Change Management is considered an asset. (CCMP, PROSCI).
Diversity Equity, Inclusion & Belonging
At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.
We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas.
We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to [email protected].
All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.
Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.
Location: Winnipeg, MB (Hybrid), CA
North York - Toronto, ON (Hybr, CA
Montreal, QC (Hybrid), CA
Edmonton, AB (Hybrid), CA
Moncton, NB (Hybrid), CA
Dartmouth, NS (Hybrid), CA
Vancouver, BC (Hybrid), CA
Ottawa, ON (Hybrid), CA
Calgary, AB (Hybrid), CA
Kitchener, ON (Hybrid), CA
Company: Wawanesa Insurance
Job ID: 9805
Employment Type: Existing Role
Working Business Language: English. This role is considered a head-office role and will be required to communicate with internal stakeholders across Canada where the primary business language utilized is English.
Salary: At Wawanesa, salary is only one component of a holistic, comprehensive and competitive offering that we provide to our employees. In addition to salary, full-time and part-time permanent employees are eligible for an annual bonus plan, leave of absence top-up programs and provided with generous vacation time, personal days, premium free benefits and pension plan.
The salary offered for this role is determined with consideration to various factors, including but not limited to: your work location, local labour market conditions, external market salary data, internal pay equity and the knowledge, skills, experience and anticipated proficiency in the role. The salary offered is estimated to be within the following range: $140,000 - $180,000. Candidates with salary expectations outside of the range are still encouraged to apply.
About Us
At Wawanesa, we offer a hybrid work environment that offers flexibility to our employees in balancing in-office (2 days per week OR 15 hours per week in a Wawanesa office) and remote work. You may work from any of the following locations: Winnipeg, MB; Vancouver, BC; Calgary, AB; Edmonton, AB; Toronto (North York), ON; Kitchener, ON; Ottawa, ON; Montreal, QC; Moncton, NB; Dartmouth; NS.
The Wawanesa Mutual Insurance Company (“Wawanesa Mutual”), founded in 1896, is one of Canada’s largest mutual insurers, with over $3.5 billion in annual revenue and assets of $10 billion (CAD). Wawanesa Mutual, with its National Headquarters in Winnipeg, is the parent company of Wawanesa Life, which provides life insurance products and services throughout Canada, and Western Financial Group, which distributes personal and business insurance across Canada. Wawanesa proudly serves more than 1.7 million members in Canada, and we are home to more than 3,300 employees distributed across the Canadian regions and communities where we operate. We give back to organizations that strengthen communities, donating more than $3.5 million annually to charitable organizations, including over $2 million annually in support of people on the front lines of climate change. We are also proud to be recognized as one of Manitoba’s Top Employers. To learn more visit wawanesa.com.
We are currently looking for dedicated, driven, and enthusiastic individuals who thrive in an environment that welcomes change and are looking for an opportunity for diverse experience and advancement on a growing team.
Job Overview
The Manager, Portfolio Delivery, leads a team of project professionals to deliver large strategic change through the development and continuous improvement of project management capabilities across the enterprise. This role ensures consistent, high-quality delivery of strategic initiatives by embedding best practices, driving strategic alignment, and enabling benefits realization. The Manager plays a key role in maturing the EPMO’s delivery model and fostering a culture of accountability, transparency, and continuous learning.
Job Responsibilities
Lead the Project Management Centre of Excellence by enhancing practices, standards, and tools with a continuous improvement mindset in alignment with enterprise strategy.
Lead a team of Project Managers, providing coaching, performance feedback, and professional development to build delivery excellence.
Collaborate with Portfolio Planning to ensure alignment between intake, prioritization, and execution processes.
Support the development and implementation of value architecture, including KPIs and success measures, to track benefits realization.
Conduct regular health checks and audits to ensure conformance to project management standards and identify opportunities for improvement.
Lead project management training and coaching initiatives across the organization to build enterprise-wide capability.
Drive project readiness including all necessary resources and processes in preparation for project launch.
Partner with Enterprise Portfolio Change to integrate change strategies into project delivery.
Contribute to strategic planning cycles by providing insights on delivery capacity, resource planning, and capability readiness.
Represent the Project Management Centre of Excellence PM COE in governance forums and contribute to the development of governance materials.
Advanced proficiency in BI tools (e.g., Tableau, Power BI), data analysis software (e.g., SQL, Python), and Excel.
Ensure consistent application of project management methodologies (e.g., PMI, Agile, SAFe) and tools (e.g., JIRA, Confluence, SharePoint).
Leads Scientific Research & Experimental Development program.
Perform other duties as assigned.
Qualifications
Bachelor’s degree in business administration, computer science, information systems, or a related field; equivalent experience considered.
Formal program/project management training from a recognized college/university.
Project Management certification and or Agile certification desired, PMP (Project Management Professional), PgMP (Program Management Professional) , ACP (Agile Certified Practitioner), CSM (Certified Scrum Master).
10+ years of progressive experience in project/program management, including leadership roles within a PMO or EPMO.
Proven experience leading and coaching high-performing project teams.
Deep knowledge of project management and agile delivery methodologies; PMP and/or Certified Scrum Master preferred.
Advanced proficiency in BI tools (e.g., Tableau, Power BI), data analysis software (e.g., SQL, Python), and Excel.
Strong understanding of portfolio management, benefits realization, and strategic execution frameworks.
Demonstrated ability to influence across business and communicate effectively with senior leadership.
Demonstrated knowledge of Canada Revenue Agency’s Scientific Research & Experimental Development program.
Knowledge of the Property & Casualty Insurance industry is considered an asset.
Insurance Professional designation is considered an asset (CIP, GIE, FCIP).
Understanding and formal training in the SAFe framework considered an asset.
Certification in Change Management is considered an asset. (CCMP, PROSCI).
Diversity Equity, Inclusion & Belonging
At Wawanesa, we are committed to Diversity, Equity, Inclusion and Belonging (DEIB) and believe that our strength lies in the diversity of our people – this is supported by having a representative workforce.
We welcome applications from all qualified candidates, including racialized persons, women, Indigenous Peoples, persons with disabilities, members of the 2SLGBTQIA+ community, gender-diverse and neurodiverse individuals, and anyone who can contribute to the further diversification of thought and ideas.
We aim to ensure our recruitment process is accessible to all candidates. If you require accommodations during any stage of the recruitment process, please reach out in confidence to [email protected].
All Wawanesa job applicants are subject to Wawanesa's Privacy Policy.
Please note that the recruitment process for this position may involve the use of AI tools to screen, assess, or select applicants. All final decisions are taken or reviewed by human recruiters and human hiring leaders in compliance with all applicable legislation.
💡 Quick Summary
Seeking a career-building opportunity? The Manager, Portfolio Delivery position is now open for candidates interested in the Finance sector. This role in Winnipeg 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 Finance is a plus.
