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
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
Intermediate to Senior Underwriter, Commercial Lines, Auto Small Business - Ontario Toronto, ON, CA, M2P-2B7 Sep 15, 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
Lead Executive Claims Analyst
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Winnipeg, MB (Hybrid), CA +9 more… Sep 2, 2026
Learning & Talent Coordinator
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Hybrid - Canada, CA +2 more… Sep 22, 2026
Manager, Operations Excellence-Term
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Manager, Underwriting Operations - Commercial Small Business
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Calgary, AB (Hybrid), CA +4 more… Sep 21, 2026
National Property Claims Adjusters - Multiple Levels (Level 1-3) - Future Opportunities Hybrid - Canada, CA +12 more… Sep 11, 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
Receivables Operations Specialist
Receivables Operations Specialist Winnipeg, MB (Hybrid), CA +10 more… Sep 23, 2026
Winnipeg, MB (Hybrid), CA +10 more… Sep 23, 2026
Receivables Reconciliation Specialist-Term
Receivables Reconciliation Specialist-Term Winnipeg, MB (Hybrid), CA +10 more… Sep 23, 2026
Winnipeg, MB (Hybrid), CA +10 more… Sep 23, 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
Salesforce Lead Developer
Salesforce Lead Developer Winnipeg, MB (Hybrid), CA +12 more… Sep 19, 2026
Winnipeg, MB (Hybrid), CA +12 more… Sep 19, 2026
Segment Specialist, Commercial Mid-Market (Manufacturing and Wholesale) Hybrid - Canada, CA Sep 14, 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 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 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 - Direct to Market (D2M)
Senior Architect - Direct to Market (D2M) Winnipeg, MB (Hybrid), CA +2 more… Sep 11, 2026
Winnipeg, MB (Hybrid), CA +2 more… Sep 11, 2026
Senior Architect - Salesforce
Senior Architect - Salesforce Winnipeg, MB (Hybrid), CA +12 more… Sep 19, 2026
Winnipeg, MB (Hybrid), 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
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
Senior Business Development Representative - MB & SK
Senior Business Development Representative - MB & SK Winnipeg, MB, CA, R3C-1P5 Sep 22, 2026
Winnipeg, MB, CA, R3C-1P5 Sep 22, 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 Business Development Specialist - Experience & Enablement
Senior Business Development Specialist - Experience & Enablement North York - Toronto, ON (Hybr, CA +8 more… Sep 14, 2026
North York - Toronto, ON (Hybr, CA +8 more… Sep 14, 2026