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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Web Application Penetration Tester
Web Application Penetration Tester Winnipeg, MB (Hybrid), CA +10 more… Aug 30, 2026
Winnipeg, MB (Hybrid), CA +10 more… Aug 30, 2026
Underwriting Quality Assurance Specialist - Commercial Lines
Underwriting Quality Assurance Specialist - Commercial Lines Hybrid - Canada, CA +11 more… Sep 3, 2026
Hybrid - Canada, CA +11 more… Sep 3, 2026
Underwriter II - Commercial Lines, Farm, Ontario
Underwriter II - Commercial Lines, Farm, Ontario North York - Toronto, ON (Hybr, CA +1 more… Aug 28, 2026
North York - Toronto, ON (Hybr, CA +1 more… Aug 28, 2026
Treasury Analyst-Term
Treasury Analyst-Term Winnipeg, MB (Hybrid), CA Sep 3, 2026
Winnipeg, MB (Hybrid), CA Sep 3, 2026
Solution Analyst II
Solution Analyst II Winnipeg, MB (Hybrid), CA +1 more… Aug 28, 2026
Winnipeg, MB (Hybrid), CA +1 more… Aug 28, 2026
Senior Underwriting Training Specialist - Commercial Lines
Senior Underwriting Training Specialist - Commercial Lines Hybrid - Canada, CA +14 more… Aug 29, 2026
Hybrid - Canada, CA +14 more… Aug 29, 2026
Senior Underwriting Specialist, Commercial Mid-Market (Manufacturing & Wholesale) Hybrid - Canada, CA Aug 16, 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
Senior Underwriter - Commercial Lines, Alberta
Senior Underwriter - Commercial Lines, Alberta Calgary, AB (Hybrid), CA +1 more… Aug 12, 2026
Calgary, AB (Hybrid), CA +1 more… Aug 12, 2026
Senior Total Rewards Specialist
Senior Total Rewards Specialist North York - Toronto, ON (Hybr, CA +9 more… Aug 27, 2026
North York - Toronto, ON (Hybr, CA +9 more… Aug 27, 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 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
Senior Organizational Change Management Specialist
Senior Organizational Change Management Specialist Winnipeg, MB (Hybrid), CA +8 more… Sep 2, 2026
Winnipeg, MB (Hybrid), CA +8 more… Sep 2, 2026
Senior Model Risk & Validation Consultant
Senior Model Risk & Validation Consultant North York - Toronto, ON (Hybr, CA +12 more… Aug 22, 2026
North York - Toronto, ON (Hybr, CA +12 more… Aug 22, 2026
Senior Innovation Consultant
Senior Innovation Consultant North York - Toronto, ON (Hybr, CA +1 more… Sep 2, 2026
North York - Toronto, ON (Hybr, CA +1 more… Sep 2, 2026
Senior Financial Analyst
Senior Financial Analyst Winnipeg, MB (Hybrid), CA +3 more… Sep 3, 2026
Winnipeg, MB (Hybrid), CA +3 more… Sep 3, 2026
Senior Field Underwriter, Commercial Mid-Market, Ontario
Senior Field Underwriter, Commercial Mid-Market, Ontario North York - Toronto, ON (Hybr, CA Aug 22, 2026
North York - Toronto, ON (Hybr, CA Aug 22, 2026
Senior Field Underwriter - Commercial, Midmarket, Alberta
Senior Field Underwriter - Commercial, Midmarket, Alberta Edmonton, AB (Hybrid), CA +2 more… Aug 24, 2026
Edmonton, AB (Hybrid), CA +2 more… Aug 24, 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
Senior Claims Adjuster - Auto Physical Damage
Senior Claims Adjuster - Auto Physical Damage North York - Toronto, ON (Hybr, CA +10 more… Aug 17, 2026
North York - Toronto, ON (Hybr, CA +10 more… Aug 17, 2026
Senior Case Manager
Senior Case Manager Hybrid - Canada, CA +10 more… Aug 21, 2026
Hybrid - Canada, CA +10 more… Aug 21, 2026
Senior Business Development Representative - Ontario
Senior Business Development Representative - Ontario North York - Toronto, ON (Hybr, CA +1 more… Aug 12, 2026
North York - Toronto, ON (Hybr, CA +1 more… Aug 12, 2026
Senior Business Development Representative - MB & SK
Senior Business Development Representative - MB & SK Winnipeg, MB, CA, R3C-1P5 Aug 24, 2026
Winnipeg, MB, CA, R3C-1P5 Aug 24, 2026
Senior Bilingual Recovery and Subrogation Claims Adjuster
Senior Bilingual Recovery and Subrogation Claims Adjuster Winnipeg, MB (Hybrid), CA +11 more… Aug 20, 2026
Winnipeg, MB (Hybrid), CA +11 more… Aug 20, 2026
Senior Bilingual Human Resources Business Partner
Senior Bilingual Human Resources Business Partner Montreal, QC (Hybrid), CA +11 more… Aug 12, 2026
Montreal, QC (Hybrid), CA +11 more… Aug 12, 2026