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
Senior Brand Marketing Specialist
Senior Brand Marketing Specialist North York - Toronto, ON (Hybr, CA Sep 25, 2026
North York - Toronto, ON (Hybr, CA Sep 25, 2026
Director, Total Rewards
Director, Total Rewards North York - Toronto, ON (Hybr, CA +8 more… Sep 23, 2026
North York - Toronto, ON (Hybr, CA +8 more… Sep 23, 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
VP, Direct Venture Marketing
VP, Direct Venture Marketing North York - Toronto, ON (Hybr, CA +4 more… Sep 17, 2026
North York - Toronto, ON (Hybr, CA +4 more… Sep 17, 2026
Senior Field Underwriter, Commercial Mid-Market, Ontario
Senior Field Underwriter, Commercial Mid-Market, Ontario North York - Toronto, ON (Hybr, CA Sep 20, 2026
North York - Toronto, ON (Hybr, CA Sep 20, 2026
Actuarial Analyst - New Grad
Actuarial Analyst - New Grad North York - Toronto, ON (Hybr, CA +12 more… Sep 16, 2026
North York - Toronto, ON (Hybr, CA +12 more… Sep 16, 2026
Senior Underwriting Training Specialist - Commercial Lines
Senior Underwriting Training Specialist - Commercial Lines North York - Toronto, ON (Hybr, CA +13 more… Sep 27, 2026
North York - Toronto, ON (Hybr, CA +13 more… Sep 27, 2026
Senior Claims Adjuster - Auto Physical Damage
Senior Claims Adjuster - Auto Physical Damage North York - Toronto, ON (Hybr, CA +10 more… Sep 15, 2026
North York - Toronto, ON (Hybr, CA +10 more… Sep 15, 2026
Product Owner-Commercial Lines
Product Owner-Commercial Lines North York - Toronto, ON (Hybr, CA +10 more… Sep 28, 2026
North York - Toronto, ON (Hybr, CA +10 more… Sep 28, 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
Senior Actuarial Analyst - Pricing Modelling
Senior Actuarial Analyst - Pricing Modelling North York - Toronto, ON (Hybr, CA +12 more… Sep 19, 2026
North York - Toronto, ON (Hybr, CA +12 more… Sep 19, 2026
Senior Total Rewards Specialist
Senior Total Rewards Specialist North York - Toronto, ON (Hybr, CA +9 more… Sep 25, 2026
North York - Toronto, ON (Hybr, CA +9 more… Sep 25, 2026
Strategic Claims Counsel, Vendor Strategy & Legal Operations
Strategic Claims Counsel, Vendor Strategy & Legal Operations North York - Toronto, ON (Hybr, CA +4 more… Sep 23, 2026
North York - Toronto, ON (Hybr, CA +4 more… Sep 23, 2026
Actuarial Consultant - Pricing Modelling
Actuarial Consultant - Pricing Modelling North York - Toronto, ON (Hybr, CA +12 more… Sep 19, 2026
North York - Toronto, ON (Hybr, CA +12 more… Sep 19, 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
Field Catastrophe Claims Representative
Field Catastrophe Claims Representative Remote - Canada, CA Sep 18, 2026
Remote - Canada, CA Sep 18, 2026
Intermediate to Senior Underwriter, Commercial Lines, Farm - Ontario Toronto, ON, CA, M2P-2B7 Sep 15, 2026
Intermediate to Senior Underwriter, Commercial Lines, P&C Small Business - Ontario Toronto, ON, CA, M2P-2B7 Sep 15, 2026
Intermediate to Senior Underwriter, Commercial Lines, Auto Small Business - Ontario Toronto, ON, CA, M2P-2B7 Sep 15, 2026
Claims Service Ambassador (Future Opportunities)
Claims Service Ambassador (Future Opportunities) Vancouver, BC (Hybrid), CA +10 more… Sep 13, 2026
Vancouver, BC (Hybrid), CA +10 more… Sep 13, 2026
Senior Field Claims Appraiser - Agricultural Equipment
Senior Field Claims Appraiser - Agricultural Equipment Wawanesa, MB, CA, R0K-2G0 Sep 1, 2026
Wawanesa, MB, CA, R0K-2G0 Sep 1, 2026
Solution Analyst II/Senior
Solution Analyst II/Senior Winnipeg, MB (Hybrid), CA +9 more… Sep 21, 2026
Winnipeg, MB (Hybrid), CA +9 more… Sep 21, 2026
Bilingual Recovery Adjuster
Bilingual Recovery Adjuster Winnipeg, MB (Hybrid), CA +11 more… Sep 18, 2026
Winnipeg, MB (Hybrid), CA +11 more… Sep 18, 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
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