Digital Transformation & Innovation

The Wawanesa Digital Transformation and Exploration team explores the art of the possible on a mission to transform and optimize business performance. We do this through teams in three functional areas: Digital Strategy and Innovation (which we call Exploration), Digital Transformation, and Operational Excellence (OpEx). 

The Digital Strategy and Exploration team works directly in-and-on innovation that creates value for Wawanesa, our customers and brokers. They research far reaching trends and technologies to build strategy, and help solve complex business problems using a systematic approach that translates high-level ideas into executable plans and prototypes.

The Digital Transformation team partners with internal stakeholders to deliver value throughout the lifecycle of our ecosystem of digital products. They emphasize data-driven decision-making, change management, and business acumen to challenge the status quo and continuously improve the digital experience for our customers, employees, and brokers.  

The Operational Excellence team serves as a center of excellence for all Wawanesa companies (Mutual, Life and General) enabling the organization to maximize value for our customers, optimize business processes through evidence based problem-solving, harness new ideas from the front-line experience and drive a culture of continuous improvement.

Together, we aspire to use digital services to uplift the Wawanesa experience in a way that clearly demonstrates we are here for our employees, brokers, and policyholders when and where they need us.

The following are some of the jobs in Digital Transformation and Innovation: 

  • Digital Transformation Specialist
  • Manager, Operations Excellence
  • Lead Process Analyst
  • Exploration Practice Lead
  • Digital Transformation Training & Communications Specialist

Research & Innovation

The Wawanesa Digital Transformation and Exploration team explores the art of the possible on a mission to transform and optimize business performance. We do this through teams in three functional areas: Digital Strategy and Innovation (which we call Exploration), Digital Transformation, and Operational Excellence (OpEx). 

The Digital Strategy and Exploration team works directly in-and-on innovation that creates value for Wawanesa, our customers and brokers. They research far reaching trends and technologies to build strategy, and help solve complex business problems using a systematic approach that translates high-level ideas into executable plans and prototypes.

The Digital Transformation team partners with internal stakeholders to deliver value throughout the lifecycle of our ecosystem of digital products. They emphasize data-driven decision-making, change management, and business acumen to challenge the status quo and continuously improve the digital experience for our customers, employees, and brokers.  

The Operational Excellence team serves as a center of excellence for all Wawanesa companies (Mutual, Life and General) enabling the organization to maximize value for our customers, optimize business processes through evidence based problem-solving, harness new ideas from the front-line experience and drive a culture of continuous improvement.

Together, we aspire to use digital services to uplift the Wawanesa experience in a way that clearly demonstrates we are here for our employees, brokers, and policyholders when and where they need us.

The following are some of the jobs in Digital Transformation and Innovation: 

  • Digital Transformation Specialist
  • Manager, Operations Excellence
  • Lead Process Analyst
  • Exploration Practice Lead
  • Digital Transformation Training & Communications Specialist
Title Location Date
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Manager, Reinsurance
Manager, Reinsurance North York - Toronto, ON (Hybr, CA +12 more… Mar 10, 2026
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National Property Claims Adjuster - Multiple Levels (Level 1-2)
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Organizational Design Manager
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Property Claims Adjuster (Bilingual)
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Property Field Claims Appraiser (bilingual)
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Regional Manager, Group
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Regional Manager, Individual - Life (External Wholesaler)
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Senior Actuarial Analyst - Research & Development
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Senior Actuarial Consultant - Rating Quality
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Senior Actuarial Consultant - Research & Development
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Senior Architect
Senior Architect Winnipeg, MB (Hybrid), CA +9 more… Mar 12, 2026
Winnipeg, MB (Hybrid), CA +9 more… Mar 12, 2026
Senior Architect - Technology
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Winnipeg, MB (Hybrid), CA +9 more… Mar 17, 2026
Senior Business Development Representative
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Senior Commercial Auto Underwriter
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Senior Commercial Underwriter - P&C
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Senior External Relations Specialist
Senior External Relations Specialist Winnipeg, MB (Hybrid), CA Mar 24, 2026
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Senior Human Resources Business Partner
Senior Human Resources Business Partner North York - Toronto, ON (Hybr, CA +2 more… Mar 25, 2026
North York - Toronto, ON (Hybr, CA +2 more… Mar 25, 2026
Senior Organizational Change Management Specialist
Senior Organizational Change Management Specialist Winnipeg, MB (Hybrid), CA +9 more… Mar 10, 2026
Winnipeg, MB (Hybrid), CA +9 more… Mar 10, 2026
Senior Reporting Analyst
Senior Reporting Analyst Hybrid - Canada, CA Mar 18, 2026
Hybrid - Canada, CA Mar 18, 2026
Senior Risk & Controls Testing Specialist
Senior Risk & Controls Testing Specialist Winnipeg, MB (Hybrid), CA +9 more… Mar 16, 2026
Winnipeg, MB (Hybrid), CA +9 more… Mar 16, 2026
Senior Solution Analyst
Senior Solution Analyst Winnipeg, MB (Hybrid), CA +1 more… Mar 24, 2026
Winnipeg, MB (Hybrid), CA +1 more… Mar 24, 2026
Senior Strategic Sourcing Specialist - Technical
Senior Strategic Sourcing Specialist - Technical Winnipeg, MB (Hybrid), CA +4 more… Mar 6, 2026
Winnipeg, MB (Hybrid), CA +4 more… Mar 6, 2026
Training and Communications Coordinator - Underwriting Personal Lines
Training and Communications Coordinator - Underwriting Personal Lines Winnipeg, MB (Hybrid), CA +9 more… Mar 3, 2026
Winnipeg, MB (Hybrid), CA +9 more… Mar 3, 2026
Underwriter II - Personal Lines
Underwriter II - Personal Lines Montreal, QC (Hybrid), CA +1 more… Mar 25, 2026
Montreal, QC (Hybrid), CA +1 more… Mar 25, 2026
Underwriting Technical Specialist - Personal Lines
Underwriting Technical Specialist - Personal Lines North York - Toronto, ON (Hybr, CA +4 more… Mar 20, 2026
North York - Toronto, ON (Hybr, CA +4 more… Mar 20, 2026