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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Workforce Management Analyst
Workforce Management Analyst North York - Toronto, ON (Hybr, CA +3 more… Jul 17, 2026
North York - Toronto, ON (Hybr, CA +3 more… Jul 17, 2026
Underwriter II - Commercial Lines, Small Business, Ontario
Underwriter II - Commercial Lines, Small Business, Ontario North York - Toronto, ON (Hybr, CA +2 more… Jul 18, 2026
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Senior Workforce Management Analyst
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Senior Underwriter - Farm, Ontario
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Senior Underwriter - Commercial Lines, Mid-Market, Ontario
Senior Underwriter - Commercial Lines, Mid-Market, Ontario North York - Toronto, ON (Hybr, CA +2 more… Jul 10, 2026
North York - Toronto, ON (Hybr, CA +2 more… Jul 10, 2026
Senior Underwriter - Commercial Lines, Alberta
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Senior Underwriter - Commercial Lines Auto
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Senior Tax Specialist-Term
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Senior Solution Analyst
Senior Solution Analyst Winnipeg, MB (Hybrid), CA +10 more… Jul 21, 2026
Winnipeg, MB (Hybrid), CA +10 more… Jul 21, 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 Financial Analyst
Senior Financial Analyst Winnipeg, MB (Hybrid), CA +3 more… Jul 7, 2026
Winnipeg, MB (Hybrid), CA +3 more… Jul 7, 2026
Senior Field Underwriter, Commercial Mid-Market, Ontario
Senior Field Underwriter, Commercial Mid-Market, Ontario North York - Toronto, ON (Hybr, CA Jul 24, 2026
North York - Toronto, ON (Hybr, CA Jul 24, 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
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 Business Development Representative - Ontario
Senior Business Development Representative - Ontario North York - Toronto, ON (Hybr, CA +1 more… Jul 14, 2026
North York - Toronto, ON (Hybr, CA +1 more… Jul 14, 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 Bilingual Recovery and Subrogation Claims Adjuster
Senior Bilingual Recovery and Subrogation Claims Adjuster Winnipeg, MB (Hybrid), CA +11 more… Jul 22, 2026
Winnipeg, MB (Hybrid), CA +11 more… Jul 22, 2026
Senior Architect - Salesforce
Senior Architect - Salesforce Winnipeg, MB (Hybrid), CA +12 more… Jul 23, 2026
Winnipeg, MB (Hybrid), CA +12 more… Jul 23, 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
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
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 Actuarial Analyst - Research & Development
Senior Actuarial Analyst - Research & Development North York - Toronto, ON (Hybr, CA +12 more… Jul 23, 2026
North York - Toronto, ON (Hybr, CA +12 more… Jul 23, 2026
Segment Specialist, Commercial Mid-Market (Manufacturing and Wholesale) Hybrid - Canada, CA Jul 18, 2026
Salesforce Lead Developer
Salesforce Lead Developer Winnipeg, MB (Hybrid), CA +12 more… Jul 23, 2026
Winnipeg, MB (Hybrid), CA +12 more… Jul 23, 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