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
Reset
Facilities Coordinator (Projects)
Facilities Coordinator (Projects) Winnipeg, MB (Onsite), CA Oct 8, 2026
Winnipeg, MB (Onsite), CA Oct 8, 2026
Workplace Safety & Security Coordinator
Workplace Safety & Security Coordinator Winnipeg, MB (Onsite), CA Oct 10, 2026
Winnipeg, MB (Onsite), CA Oct 10, 2026
Salesforce Lead Developer
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Winnipeg, MB (Hybrid), CA +12 more… Oct 18, 2026
Machine Learning Operations Engineer/Senior
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Winnipeg, MB (Hybrid), CA +5 more… Oct 28, 2026
Supervisor, Claims - Large Loss
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Winnipeg, MB (Hybrid), CA +11 more… Oct 26, 2026
Senior Strategic Sourcing Specialist
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Product Specialist - Individual Insurance
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Senior Product Specialist - Personal Lines
Senior Product Specialist - Personal Lines Winnipeg, MB (Hybrid), CA +10 more… Nov 4, 2026
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Bilingual Claims Adjusters - Farm/Commercial
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Associate Product Owner
Associate Product Owner Winnipeg, MB (Hybrid), CA +11 more… Oct 28, 2026
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Application Developer II - Digital Platforms
Application Developer II - Digital Platforms Winnipeg, MB (Hybrid), CA +8 more… Oct 17, 2026
Winnipeg, MB (Hybrid), CA +8 more… Oct 17, 2026
Compliance, Risk & Controls Advisor - Personal Lines
Compliance, Risk & Controls Advisor - Personal Lines Winnipeg, MB (Hybrid), CA +9 more… Oct 21, 2026
Winnipeg, MB (Hybrid), CA +9 more… Oct 21, 2026
Reinsurance Specialist
Reinsurance Specialist Winnipeg, MB (Hybrid), CA +10 more… Nov 5, 2026
Winnipeg, MB (Hybrid), CA +10 more… Nov 5, 2026
Intermediate to Senior Underwriter, Commercial Lines, Auto Small Business - Ontario Toronto, ON, CA, M2P-2B7 Oct 14, 2026
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Intermediate to Senior Underwriter, Commercial Lines, P&C Small Business - Ontario Toronto, ON, CA, M2P-2B7 Oct 14, 2026
Actuarial Expert - Alberta Auto Pricing
Actuarial Expert - Alberta Auto Pricing Toronto, ON (Hybrid), CA +13 more… Oct 9, 2026
Toronto, ON (Hybrid), CA +13 more… Oct 9, 2026
Senior Bilingual Field Catastrophe Claims Representative
Senior Bilingual Field Catastrophe Claims Representative Remote - Canada, CA +2 more… Oct 9, 2026
Remote - Canada, CA +2 more… Oct 9, 2026
Field Catastrophe Claims Representative
Field Catastrophe Claims Representative Remote - Canada, CA Oct 17, 2026
Remote - Canada, CA Oct 17, 2026
Director, Total Rewards
Director, Total Rewards North York - Toronto, ON (Hybr, CA +8 more… Oct 22, 2026
North York - Toronto, ON (Hybr, CA +8 more… Oct 22, 2026
Senior Business Development Representative - Ontario
Senior Business Development Representative - Ontario North York - Toronto, ON (Hybr, CA +1 more… Oct 9, 2026
North York - Toronto, ON (Hybr, CA +1 more… Oct 9, 2026
Actuarial Consultant - Pricing Modelling
Actuarial Consultant - Pricing Modelling North York - Toronto, ON (Hybr, CA +12 more… Oct 18, 2026
North York - Toronto, ON (Hybr, CA +12 more… Oct 18, 2026
Senior Actuarial Analyst - Pricing Modelling
Senior Actuarial Analyst - Pricing Modelling North York - Toronto, ON (Hybr, CA +12 more… Oct 18, 2026
North York - Toronto, ON (Hybr, CA +12 more… Oct 18, 2026
Senior Actuarial Analyst - Corporate Actuarial - Reserving (All Levels)
Senior Actuarial Analyst - Corporate Actuarial - Reserving (All Levels) North York - Toronto, ON (Hybr, CA +11 more… Nov 4, 2026
North York - Toronto, ON (Hybr, CA +11 more… Nov 4, 2026
Regional Manager, Individual - Life (External Wholesaler)
Regional Manager, Individual - Life (External Wholesaler) North York - Toronto, ON (Hybr, CA Oct 21, 2026
North York - Toronto, ON (Hybr, CA Oct 21, 2026