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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Facilities Operations Support (Building Services)
Facilities Operations Support (Building Services) Winnipeg, MB, CA, R3C-1P5 Jul 16, 2026
Winnipeg, MB, CA, R3C-1P5 Jul 16, 2026
Finance Intern
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Manager, Business Development - Manitoba & Saskatchewan Region Winnipeg, MB (Hybrid), CA Jun 26, 2026
Bilingual Talent Sourcing Partner
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Salesforce Lead Developer
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Senior Architect - Contact Center and Conversational AI
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Senior Architect - Salesforce
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Manager, Machine Learning Operations (MLOps)
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Commercial National Programs Adjuster - Levels 2 and 3
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Manager, Finance Business Partner - Personal Lines
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Senior Financial Analyst
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Winnipeg, MB (Hybrid), CA +3 more… Jul 7, 2026
Intermediate Claims Adjuster - Auto Physical Damage (Future Opportunities)
Intermediate Claims Adjuster - Auto Physical Damage (Future Opportunities) Winnipeg, MB (Hybrid), CA +10 more… Jul 9, 2026
Winnipeg, MB (Hybrid), CA +10 more… Jul 9, 2026
Senior Architect - Direct to Market (D2M)
Senior Architect - Direct to Market (D2M) Winnipeg, MB (Hybrid), CA +2 more… Jul 15, 2026
Winnipeg, MB (Hybrid), CA +2 more… Jul 15, 2026
Underwriting Assistant - Group
Underwriting Assistant - Group Winnipeg, MB (Hybrid), CA Jul 15, 2026
Winnipeg, MB (Hybrid), CA Jul 15, 2026
Senior Business Development Representative - BC Region
Senior Business Development Representative - BC Region Vancouver, BC (Hybrid), CA Jul 11, 2026
Vancouver, BC (Hybrid), CA Jul 11, 2026
Actuarial Analyst to Senior Actuarial Consultant - Commercial Pricing (All Levels) Vancouver, BC (Hybrid), CA +14 more… Jun 25, 2026
Field Claims Adjuster - Property
Field Claims Adjuster - Property Thunder Bay, ON, CA, P7B-5Z6 +5 more… Jun 25, 2026
Thunder Bay, ON, CA, P7B-5Z6 +5 more… Jun 25, 2026
Senior Field Underwriter, Commercial Mid-Market, Ontario
Senior Field Underwriter, Commercial Mid-Market, Ontario North York - Toronto, ON (Hybr, CA Jun 25, 2026
North York - Toronto, ON (Hybr, CA Jun 25, 2026
Organizational Design Manager
Organizational Design Manager North York - Toronto, ON (Hybr, CA +9 more… Jun 26, 2026
North York - Toronto, ON (Hybr, CA +9 more… Jun 26, 2026
Senior Actuarial Consultant - Corporate Actuarial - Forecasting
Senior Actuarial Consultant - Corporate Actuarial - Forecasting North York - Toronto, ON (Hybr, CA +13 more… Jun 29, 2026
North York - Toronto, ON (Hybr, CA +13 more… Jun 29, 2026
Senior Underwriter - Commercial Lines Auto
Senior Underwriter - Commercial Lines Auto North York - Toronto, ON (Hybr, CA +3 more… Jul 7, 2026
North York - Toronto, ON (Hybr, CA +3 more… Jul 7, 2026
Senior Underwriter - Commercial Lines, Ontario
Senior Underwriter - Commercial Lines, Ontario North York - Toronto, ON (Hybr, CA +2 more… Jul 10, 2026
North York - Toronto, ON (Hybr, CA +2 more… Jul 10, 2026
Senior Digital Transformation Specialist (Commercial Lines)
Senior Digital Transformation Specialist (Commercial Lines) North York - Toronto, ON (Hybr, CA +8 more… Jul 10, 2026
North York - Toronto, ON (Hybr, CA +8 more… Jul 10, 2026
Senior Human Resources Business Partner
Senior Human Resources Business Partner North York - Toronto, ON (Hybr, CA +1 more… Jul 14, 2026
North York - Toronto, ON (Hybr, CA +1 more… Jul 14, 2026
Senior Broker Training Specialist
Senior Broker Training Specialist North York - Toronto, ON (Hybr, CA +9 more… Jul 13, 2026
North York - Toronto, ON (Hybr, CA +9 more… Jul 13, 2026