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
Product Innovation Strategist
Product Innovation Strategist North York - Toronto, ON (Hybr, CA +9 more… Aug 7, 2026
North York - Toronto, ON (Hybr, CA +9 more… Aug 7, 2026
Organizational Design Manager
Organizational Design Manager North York - Toronto, ON (Hybr, CA +9 more… Jul 25, 2026
North York - Toronto, ON (Hybr, CA +9 more… Jul 25, 2026
National Property Claims Adjusters - Multiple Levels (Level 1-3) - Future Opportunities Hybrid - Canada, CA +12 more… Aug 13, 2026
Manufacturing and Wholesale Underwriter Specialist, Commercial Mid-Market Hybrid - Canada, CA Jul 18, 2026
Manager, Underwriting Operations, Commercial Mid-Market - Ontario Toronto, ON, CA, M2P-2B7 Aug 6, 2026
Manager, Actuarial Pricing - National Initiatives
Manager, Actuarial Pricing - National Initiatives North York - Toronto, ON (Hybr, CA +12 more… Jul 23, 2026
North York - Toronto, ON (Hybr, CA +12 more… Jul 23, 2026
Life Insurance Specialist - (Internal Wholesaler)
Life Insurance Specialist - (Internal Wholesaler) North York - Toronto, ON (Hybr, CA +2 more… Aug 12, 2026
North York - Toronto, ON (Hybr, CA +2 more… Aug 12, 2026
Lead Executive Claims Analyst
Lead Executive Claims Analyst Winnipeg, MB (Hybrid), CA +9 more… Aug 4, 2026
Winnipeg, MB (Hybrid), CA +9 more… Aug 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… Aug 7, 2026
Montreal, QC (Hybrid), CA +1 more… Aug 7, 2026
Intermediate Claims Adjuster - Auto Physical Damage (Future Opportunities)
Intermediate Claims Adjuster - Auto Physical Damage (Future Opportunities) Winnipeg, MB (Hybrid), CA +10 more… Aug 7, 2026
Winnipeg, MB (Hybrid), CA +10 more… Aug 7, 2026
Group Underwriting Consultant
Group Underwriting Consultant Kitchener, ON (Hybrid), CA +1 more… Jul 23, 2026
Kitchener, ON (Hybrid), CA +1 more… Jul 23, 2026
Financial Analyst
Financial Analyst Winnipeg, MB (Hybrid), CA +1 more… Aug 12, 2026
Winnipeg, MB (Hybrid), CA +1 more… Aug 12, 2026
Facilities Operations Support (Building Services)
Facilities Operations Support (Building Services) Winnipeg, MB, CA, R3C-1P5 Aug 14, 2026
Winnipeg, MB, CA, R3C-1P5 Aug 14, 2026
Facilities Coordinator (Projects)
Facilities Coordinator (Projects) Winnipeg, MB (Onsite), CA Aug 11, 2026
Winnipeg, MB (Onsite), CA Aug 11, 2026
Director, Underwriting Operations, Commercial Mid-Market - West
Director, Underwriting Operations, Commercial Mid-Market - West Calgary, AB (Hybrid), CA +3 more… Aug 5, 2026
Calgary, AB (Hybrid), CA +3 more… Aug 5, 2026
Director, Corporate Actuarial
Director, Corporate Actuarial North York - Toronto, ON (Hybr, CA +11 more… Aug 12, 2026
North York - Toronto, ON (Hybr, CA +11 more… Aug 12, 2026
Commercial National Programs Adjuster - Levels 2 and 3
Commercial National Programs Adjuster - Levels 2 and 3 Winnipeg, MB (Hybrid), CA +10 more… Aug 13, 2026
Winnipeg, MB (Hybrid), CA +10 more… Aug 13, 2026
Claims Service Ambassador (Future Opportunities)
Claims Service Ambassador (Future Opportunities) Winnipeg, MB (Hybrid), CA +11 more… Jul 17, 2026
Winnipeg, MB (Hybrid), CA +11 more… Jul 17, 2026
Claims Adjusters Multiple Levels - Farm/Commercial
Claims Adjusters Multiple Levels - Farm/Commercial Winnipeg, MB (Hybrid), CA +12 more… Jul 28, 2026
Winnipeg, MB (Hybrid), CA +12 more… Jul 28, 2026
Claims Adjuster - Inside Large Loss Level 3
Claims Adjuster - Inside Large Loss Level 3 Calgary, AB (Hybrid), CA +11 more… Jul 29, 2026
Calgary, AB (Hybrid), CA +11 more… Jul 29, 2026
Catastrophe Risk Specialist
Catastrophe Risk Specialist Hybrid - Canada, CA +8 more… Jul 23, 2026
Hybrid - Canada, CA +8 more… Jul 23, 2026
Casualty Claims Adjusters - Multiple Levels (CGL)
Casualty Claims Adjusters - Multiple Levels (CGL) Winnipeg, MB (Hybrid), CA +10 more… Aug 11, 2026
Winnipeg, MB (Hybrid), CA +10 more… Aug 11, 2026
Bilingual Talent Sourcing Partner
Bilingual Talent Sourcing Partner Winnipeg, MB (Hybrid), CA +9 more… Aug 7, 2026
Winnipeg, MB (Hybrid), CA +9 more… Aug 7, 2026
Bilingual Claims Service Ambassador (Future Opportunities)
Bilingual Claims Service Ambassador (Future Opportunities) Montreal, QC (Hybrid), CA +7 more… Jul 29, 2026
Montreal, QC (Hybrid), CA +7 more… Jul 29, 2026
Bilingual Claims Quality Assurance Analyst
Bilingual Claims Quality Assurance Analyst Montreal, QC (Hybrid), CA +11 more… Aug 14, 2026
Montreal, QC (Hybrid), CA +11 more… Aug 14, 2026