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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Director, Direct Venture Pricing
Director, Direct Venture Pricing North York - Toronto, ON (Hybr, CA +9 more… Aug 28, 2026
North York - Toronto, ON (Hybr, CA +9 more… Aug 28, 2026
Senior Risk Services Consultant
Senior Risk Services Consultant Montreal, Quebec, CA, H4P-2J4 Aug 28, 2026
Montreal, Quebec, CA, H4P-2J4 Aug 28, 2026
Senior Underwriting Training Specialist - Commercial Lines
Senior Underwriting Training Specialist - Commercial Lines North York - Toronto, ON (Hybr, CA +13 more… Aug 29, 2026
North York - Toronto, ON (Hybr, CA +13 more… Aug 29, 2026
Web Application Penetration Tester
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Winnipeg, MB (Hybrid), CA +10 more… Aug 30, 2026
Senior Field Claims Appraiser - Agricultural Equipment
Senior Field Claims Appraiser - Agricultural Equipment Wawanesa, MB, CA, R0K-2G0 Sep 1, 2026
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Senior Organizational Change Management Specialist
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Lead Executive Claims Analyst
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Winnipeg, MB (Hybrid), CA +9 more… Sep 2, 2026
Senior Product Development Specialist, (Personal Lines)
Senior Product Development Specialist, (Personal Lines) Winnipeg, MB (Hybrid), CA Sep 3, 2026
Winnipeg, MB (Hybrid), CA Sep 3, 2026
(*) Bilingual Farm Underwriting Specialist, Commercial Mid-Market
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Montreal, QC (Hybrid), CA +5 more… Sep 4, 2026
Regional Manager, Individual - Life (External Wholesaler)
Regional Manager, Individual - Life (External Wholesaler) Kingston, ON, CA, K7L 3N6 +1 more… Sep 4, 2026
Kingston, ON, CA, K7L 3N6 +1 more… Sep 4, 2026
Intermediate or Senior P&C Commercial Underwriter (Mid-Market)
Intermediate or Senior P&C Commercial Underwriter (Mid-Market) Montreal, QC (Hybrid), CA +1 more… Sep 5, 2026
Montreal, QC (Hybrid), CA +1 more… Sep 5, 2026
Senior Architect - Data & AI
Senior Architect - Data & AI Winnipeg, MB (Hybrid), CA +10 more… Sep 5, 2026
Winnipeg, MB (Hybrid), CA +10 more… Sep 5, 2026
Claims Adjusters - Auto Physical Damage - All Levels (Future Opportunities)
Claims Adjusters - Auto Physical Damage - All Levels (Future Opportunities) North York - Toronto, ON (Hybr, CA +10 more… Sep 5, 2026
North York - Toronto, ON (Hybr, CA +10 more… Sep 5, 2026
Senior Architect - Contact Center and Conversational AI
Senior Architect - Contact Center and Conversational AI Winnipeg, MB (Hybrid), CA +5 more… Sep 5, 2026
Winnipeg, MB (Hybrid), CA +5 more… Sep 5, 2026
Senior Underwriter - Commercial Lines, Mid-Market, Ontario
Senior Underwriter - Commercial Lines, Mid-Market, Ontario North York - Toronto, ON (Hybr, CA +2 more… Sep 6, 2026
North York - Toronto, ON (Hybr, CA +2 more… Sep 6, 2026
Facilities Coordinator (Projects)
Facilities Coordinator (Projects) Winnipeg, MB (Onsite), CA Sep 9, 2026
Winnipeg, MB (Onsite), CA Sep 9, 2026
Bilingual Underwriting Assistant - Commercial Lines
Bilingual Underwriting Assistant - Commercial Lines Montreal, QC (Hybrid), CA Sep 10, 2026
Montreal, QC (Hybrid), CA Sep 10, 2026
VP, Enabling Functions - Planning & Performance
VP, Enabling Functions - Planning & Performance North York - Toronto, ON (Hybr, CA Sep 10, 2026
North York - Toronto, ON (Hybr, CA Sep 10, 2026
Actuarial Expert - Alberta Auto Pricing
Actuarial Expert - Alberta Auto Pricing Montreal, QC (Hybrid), CA +12 more… Sep 10, 2026
Montreal, QC (Hybrid), CA +12 more… Sep 10, 2026
Farm Underwriter (intermediate to senior level)
Farm Underwriter (intermediate to senior level) Montreal, QC (Hybrid), CA +2 more… Sep 10, 2026
Montreal, QC (Hybrid), CA +2 more… Sep 10, 2026
Senior Bilingual Field Catastrophe Claims Representative
Senior Bilingual Field Catastrophe Claims Representative Remote - Canada, CA +2 more… Sep 10, 2026
Remote - Canada, CA +2 more… Sep 10, 2026
Senior Business Development Representative - Ontario
Senior Business Development Representative - Ontario North York - Toronto, ON (Hybr, CA +1 more… Sep 10, 2026
North York - Toronto, ON (Hybr, CA +1 more… Sep 10, 2026
Catastrophe Claims Representative I
Catastrophe Claims Representative I Calgary, AB (Hybrid), CA +2 more… Sep 11, 2026
Calgary, AB (Hybrid), CA +2 more… Sep 11, 2026
Workplace Safety & Security Coordinator
Workplace Safety & Security Coordinator Winnipeg, MB (Onsite), CA Sep 11, 2026
Winnipeg, MB (Onsite), CA Sep 11, 2026
(*) Commercial National Programs Adjuster - Level 3
(*) Commercial National Programs Adjuster - Level 3 Winnipeg, MB (Hybrid), CA +10 more… Sep 11, 2026
Winnipeg, MB (Hybrid), CA +10 more… Sep 11, 2026