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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Vendor Management Specialist - Claims
Vendor Management Specialist - Claims Hybrid - Canada, CA +5 more… May 26, 2026
Hybrid - Canada, CA +5 more… May 26, 2026
Sustainability Specialist
Sustainability Specialist Winnipeg, MB (Hybrid), CA +8 more… May 20, 2026
Winnipeg, MB (Hybrid), CA +8 more… May 20, 2026
Supervisor, Claims - Subrogation and Recovery
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Calgary, AB (Hybrid), CA +10 more… Jun 2, 2026
Senior Underwriting Training Specialist - Commercial Lines
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Senior Project Manager
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Senior Product Specialist-Personal Lines
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Senior Human Resources Business Partner
Senior Human Resources Business Partner Winnipeg, MB (Hybrid), CA May 11, 2026
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Senior Communications Business Partner
Senior Communications Business Partner North York - Toronto, ON (Hybr, CA May 23, 2026
North York - Toronto, ON (Hybr, CA May 23, 2026
Senior Commercial Auto Underwriter
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Montreal, QC (Hybrid), CA +1 more… May 25, 2026
Senior Architect - Life
Senior Architect - Life Winnipeg, MB (Hybrid), CA +2 more… May 27, 2026
Winnipeg, MB (Hybrid), CA +2 more… May 27, 2026
Senior Architect - Customer & Broker Engagement Technology
Senior Architect - Customer & Broker Engagement Technology Hybrid - Canada, CA +10 more… May 12, 2026
Hybrid - Canada, CA +10 more… May 12, 2026
Senior Application Developer - Guidewire
Senior Application Developer - Guidewire Winnipeg, MB (Hybrid), CA +9 more… May 27, 2026
Winnipeg, MB (Hybrid), CA +9 more… May 27, 2026
Senior Actuarial Consultant - Corporate Actuarial - Forecasting
Senior Actuarial Consultant - Corporate Actuarial - Forecasting North York - Toronto, ON (Hybr, CA +12 more… May 11, 2026
North York - Toronto, ON (Hybr, CA +12 more… May 11, 2026
Senior Actuarial Analyst / Actuarial Consultant - Pricing Excellence
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Montreal, QC (Hybrid), CA +12 more… May 16, 2026
Senior Actuarial Analyst / Actuarial Consultant - Personal Pricing Insights
Senior Actuarial Analyst / Actuarial Consultant - Personal Pricing Insights North York - Toronto, ON (Hybr, CA +13 more… May 30, 2026
North York - Toronto, ON (Hybr, CA +13 more… May 30, 2026
Regional Manager, Individual - Life (External Wholesaler) - Alberta
Regional Manager, Individual - Life (External Wholesaler) - Alberta Calgary, AB (Hybrid), CA +1 more… May 28, 2026
Calgary, AB (Hybrid), CA +1 more… May 28, 2026
Recovery Claims Adjuster - Level 2
Recovery Claims Adjuster - Level 2 Hybrid - Canada, CA +11 more… Jun 2, 2026
Hybrid - Canada, CA +11 more… Jun 2, 2026
Organizational Design Manager
Organizational Design Manager North York - Toronto, ON (Hybr, CA +9 more… May 28, 2026
North York - Toronto, ON (Hybr, CA +9 more… May 28, 2026
National Property Claims Adjuster - Multiple Levels (Level 1-3)
National Property Claims Adjuster - Multiple Levels (Level 1-3) Hybrid - Canada, CA +12 more… Jun 4, 2026
Hybrid - Canada, CA +12 more… Jun 4, 2026
Manager, Machine Learning Operations (MLOps)
Manager, Machine Learning Operations (MLOps) Winnipeg, MB (Hybrid), CA +2 more… May 17, 2026
Winnipeg, MB (Hybrid), CA +2 more… May 17, 2026
Field Underwriter - Commercial, Midmarket - Alberta
Field Underwriter - Commercial, Midmarket - Alberta Edmonton, AB (Hybrid), CA +2 more… May 29, 2026
Edmonton, AB (Hybrid), CA +2 more… May 29, 2026
Field Claims Adjuster - Property
Field Claims Adjuster - Property Remote - Canada, CA +15 more… May 27, 2026
Remote - Canada, CA +15 more… May 27, 2026
Facilities Coordinator
Facilities Coordinator Winnipeg, MB (Onsite), CA Jun 5, 2026
Winnipeg, MB (Onsite), CA Jun 5, 2026
Commercial P&C Underwriter - Small Business
Commercial P&C Underwriter - Small Business Montreal, QC (Hybrid), CA May 28, 2026
Montreal, QC (Hybrid), CA May 28, 2026
Claims Technical Specialist - Alberta Accident Benefits
Claims Technical Specialist - Alberta Accident Benefits Winnipeg, MB (Hybrid), CA +3 more… May 28, 2026
Winnipeg, MB (Hybrid), CA +3 more… May 28, 2026