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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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
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
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
Senior Digital Transformation Specialist North York - Toronto, ON (Hybr, CA +8 more… Jul 10, 2026
North York - Toronto, ON (Hybr, CA +8 more… Jul 10, 2026
Group Benefits Service Associate
Group Benefits Service Associate Kitchener, ON (Hybrid), CA +1 more… Jul 10, 2026
Kitchener, ON (Hybrid), CA +1 more… Jul 10, 2026
Bilingual Talent Sourcing Partner
Bilingual Talent Sourcing Partner Winnipeg, MB (Hybrid), CA +9 more… Jul 9, 2026
Winnipeg, MB (Hybrid), CA +9 more… Jul 9, 2026
Senior Architect - Contact Center and Conversational AI
Senior Architect - Contact Center and Conversational AI Winnipeg, MB (Hybrid), CA +5 more… Jul 9, 2026
Winnipeg, MB (Hybrid), CA +5 more… Jul 9, 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
Product Innovation Strategist
Product Innovation Strategist Hybrid - Canada, CA Jul 9, 2026
Hybrid - Canada, CA Jul 9, 2026
Regional Manager, Individual - Life (External Wholesaler)
Regional Manager, Individual - Life (External Wholesaler) Kingston, ON, CA, K7L 3N6 +2 more… Jul 8, 2026
Kingston, ON, CA, K7L 3N6 +2 more… Jul 8, 2026
Finance Intern
Finance Intern Winnipeg, MB (Onsite), CA Jul 8, 2026
Winnipeg, MB (Onsite), CA Jul 8, 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 Financial Analyst
Senior Financial Analyst Winnipeg, MB (Hybrid), CA +3 more… Jul 7, 2026
Winnipeg, MB (Hybrid), CA +3 more… Jul 7, 2026
Bilingual Underwriting Assistant - Commercial Lines
Bilingual Underwriting Assistant - Commercial Lines Montreal, QC (Hybrid), CA Jul 4, 2026
Montreal, QC (Hybrid), CA Jul 4, 2026
Bilingual Claims Service Ambassador (Future Opportunities)
Bilingual Claims Service Ambassador (Future Opportunities) Montreal, QC (Hybrid), CA +7 more… Jun 30, 2026
Montreal, QC (Hybrid), CA +7 more… Jun 30, 2026
Claims Adjuster - Inside Large Loss Level 3
Claims Adjuster - Inside Large Loss Level 3 Calgary, AB (Hybrid), CA +11 more… Jun 30, 2026
Calgary, AB (Hybrid), CA +11 more… Jun 30, 2026
Bilingual Broker Billing Specialist
Bilingual Broker Billing Specialist Calgary, AB (Hybrid), CA +2 more… Jun 30, 2026
Calgary, AB (Hybrid), CA +2 more… Jun 30, 2026
Web Application Penetration Tester
Web Application Penetration Tester Winnipeg, MB (Hybrid), CA +10 more… Jun 30, 2026
Winnipeg, MB (Hybrid), CA +10 more… Jun 30, 2026
Facilities Coordinator
Facilities Coordinator Kitchener, ON (Onsite), CA Jun 30, 2026
Kitchener, ON (Onsite), CA Jun 30, 2026
Strategic Broker Relationship Manager - West
Strategic Broker Relationship Manager - West Hybrid - Canada, CA +4 more… Jun 30, 2026
Hybrid - Canada, CA +4 more… Jun 30, 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
Vendor Management Specialist - Claims
Vendor Management Specialist - Claims Hybrid - Canada, CA +5 more… Jun 27, 2026
Hybrid - Canada, CA +5 more… Jun 27, 2026
Senior Field Underwriter - Commercial, Midmarket, Alberta
Senior Field Underwriter - Commercial, Midmarket, Alberta Edmonton, AB (Hybrid), CA +2 more… Jun 27, 2026
Edmonton, AB (Hybrid), CA +2 more… Jun 27, 2026
Commercial P&C Underwriter - Small Business
Commercial P&C Underwriter - Small Business Montreal, QC (Hybrid), CA Jun 26, 2026
Montreal, QC (Hybrid), CA Jun 26, 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