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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Senior Architect
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Winnipeg, MB (Hybrid), CA +9 more… Mar 12, 2026
Senior Risk & Controls Testing Specialist
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Manager, Advanced Analytics
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Senior Organizational Change Management Specialist
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Legal Counsel
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Machine Learning Engineer
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Winnipeg, MB (Hybrid), CA +10 more… Mar 26, 2026
Senior Architect - Technology
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Claims Technical Specialist - Alberta Accident Benefits
Claims Technical Specialist - Alberta Accident Benefits Winnipeg, MB (Hybrid), CA +3 more… Mar 31, 2026
Winnipeg, MB (Hybrid), CA +3 more… Mar 31, 2026
Claims Administrator
Claims Administrator Winnipeg, MB (Hybrid), CA Apr 2, 2026
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VP, Personal Lines, National Underwriting
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Winnipeg, MB (Hybrid), CA +4 more… Apr 2, 2026
Software Engineer
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Winnipeg, MB (Hybrid), CA Mar 31, 2026
Manager, Business Intelligence
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Senior Strategic Sourcing Specialist - Technical
Senior Strategic Sourcing Specialist - Technical Winnipeg, MB (Hybrid), CA +4 more… Apr 4, 2026
Winnipeg, MB (Hybrid), CA +4 more… Apr 4, 2026
Employee Listening Manager
Employee Listening Manager Winnipeg, MB (Hybrid), CA +9 more… Apr 4, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 4, 2026
Field Underwriter - Commercial, Midmarket
Field Underwriter - Commercial, Midmarket Ottawa, ON (Hybrid), CA +2 more… Mar 31, 2026
Ottawa, ON (Hybrid), CA +2 more… Mar 31, 2026
Manager, Reinsurance
Manager, Reinsurance North York - Toronto, ON (Hybr, CA +12 more… Mar 10, 2026
North York - Toronto, ON (Hybr, CA +12 more… Mar 10, 2026
Senior Business Development Representative
Senior Business Development Representative North York - Toronto, ON (Hybr, CA +1 more… Mar 15, 2026
North York - Toronto, ON (Hybr, CA +1 more… Mar 15, 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
Manager, Actuarial - Rating Quality
Manager, Actuarial - Rating Quality North York - Toronto, ON (Hybr, CA +14 more… Mar 23, 2026
North York - Toronto, ON (Hybr, CA +14 more… Mar 23, 2026
Actuarial Expert, Life Risk and ALM
Actuarial Expert, Life Risk and ALM North York - Toronto, ON (Hybr, CA +13 more… Mar 17, 2026
North York - Toronto, ON (Hybr, CA +13 more… Mar 17, 2026
Actuarial Consultant / Senior Actuarial Consultant - Commercial Auto Pricing
Actuarial Consultant / Senior Actuarial Consultant - Commercial Auto Pricing North York - Toronto, ON (Hybr, CA +12 more… Mar 25, 2026
North York - Toronto, ON (Hybr, CA +12 more… Mar 25, 2026