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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(*) Bilingual Farm Underwriting Specialist, Commercial Mid-Market
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Actuarial Analyst - New Grad
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Actuarial Consultant - Research & Development
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Casualty Claims Adjusters - Multiple Levels (CGL)
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Claims Adjusters Multiple Levels - Farm/Commercial
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Claims Assistant - Accident Benefits
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Claims Service Ambassador (Future Opportunities)
Claims Service Ambassador (Future Opportunities) Winnipeg, MB (Hybrid), CA +11 more… Aug 15, 2026
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Claims Technical Specialist
Claims Technical Specialist Calgary, AB (Hybrid), CA +11 more… Aug 20, 2026
Calgary, AB (Hybrid), CA +11 more… Aug 20, 2026
Commercial National Programs Adjuster - Levels 2 and 3
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Director, Direct Venture Pricing
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Director, Enabling Functions - Planning & Performance
Director, Enabling Functions - Planning & Performance North York - Toronto, ON (Hybr, CA Sep 3, 2026
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Director, Total Rewards
Director, Total Rewards Winnipeg, MB (Hybrid), CA +8 more… Aug 25, 2026
Winnipeg, MB (Hybrid), CA +8 more… Aug 25, 2026
Director, Underwriting Operations, Commercial Mid-Market - West
Director, Underwriting Operations, Commercial Mid-Market - West Calgary, AB (Hybrid), CA +3 more… Sep 3, 2026
Calgary, AB (Hybrid), CA +3 more… Sep 3, 2026
Facilities Coordinator (Projects)
Facilities Coordinator (Projects) Winnipeg, MB (Onsite), CA Aug 11, 2026
Winnipeg, MB (Onsite), CA Aug 11, 2026
Financial Analyst
Financial Analyst Winnipeg, MB (Hybrid), CA +1 more… Aug 12, 2026
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