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
Manager, Portfolio Delivery
Manager, Portfolio Delivery Winnipeg, MB (Hybrid), CA +9 more… Mar 25, 2026
Winnipeg, MB (Hybrid), CA +9 more… Mar 25, 2026
Legal Counsel
Legal Counsel Winnipeg, MB (Hybrid), CA Mar 25, 2026
Winnipeg, MB (Hybrid), CA Mar 25, 2026
Claims Technical Specialist - Alberta Accident Benefits
Claims Technical Specialist - Alberta Accident Benefits Winnipeg, MB (Hybrid), CA +3 more… Mar 31, 2026
Winnipeg, MB (Hybrid), CA +3 more… Mar 31, 2026
VP, Personal Lines, National Underwriting
VP, Personal Lines, National Underwriting Winnipeg, MB (Hybrid), CA +4 more… Apr 2, 2026
Winnipeg, MB (Hybrid), CA +4 more… Apr 2, 2026
Senior Organizational Change Management Specialist
Senior Organizational Change Management Specialist Winnipeg, MB (Hybrid), CA +9 more… Apr 8, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 8, 2026
Senior Risk & Controls Testing Specialist
Senior Risk & Controls Testing Specialist Winnipeg, MB (Hybrid), CA +9 more… Apr 14, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 14, 2026
Manager, Enterprise Treasury
Manager, Enterprise Treasury Winnipeg, MB (Hybrid), CA Apr 13, 2026
Winnipeg, MB (Hybrid), CA Apr 13, 2026
Senior Architect - Technology
Senior Architect - Technology Winnipeg, MB (Hybrid), CA +9 more… Apr 15, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 15, 2026
Senior Data Analyst
Senior Data Analyst Winnipeg, MB (Hybrid), CA +4 more… Apr 15, 2026
Winnipeg, MB (Hybrid), CA +4 more… Apr 15, 2026
Manager, Advanced Analytics
Manager, Advanced Analytics Winnipeg, MB (Hybrid), CA +2 more… Apr 18, 2026
Winnipeg, MB (Hybrid), CA +2 more… Apr 18, 2026
Senior Process Analyst
Senior Process Analyst Winnipeg, MB (Hybrid), CA +9 more… Apr 21, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 21, 2026
Remittance Specialist- 12 month Term Position
Remittance Specialist- 12 month Term Position Winnipeg, MB (Hybrid), CA Apr 20, 2026
Winnipeg, MB (Hybrid), CA Apr 20, 2026
Senior Executive Claims Analyst
Senior Executive Claims Analyst Winnipeg, MB (Hybrid), CA +9 more… Apr 7, 2026
Winnipeg, MB (Hybrid), CA +9 more… Apr 7, 2026
Senior Business Development Representative - Saskatchewan & Manitoba
Senior Business Development Representative - Saskatchewan & Manitoba Winnipeg, MB (Hybrid), CA +2 more… Apr 22, 2026
Winnipeg, MB (Hybrid), CA +2 more… Apr 22, 2026
Field Underwriter - Commercial, Midmarket
Field Underwriter - Commercial, Midmarket Ottawa, ON (Hybrid), CA +2 more… Mar 31, 2026
Ottawa, ON (Hybrid), CA +2 more… Mar 31, 2026
Facilities Operations Support - 6 month term
Facilities Operations Support - 6 month term North York-Toronto, ON (Onsite, CA Apr 20, 2026
North York-Toronto, ON (Onsite, CA Apr 20, 2026
Actuarial Consultant / Senior Actuarial Consultant - Commercial Auto Pricing
Actuarial Consultant / Senior Actuarial Consultant - Commercial Auto Pricing North York - Toronto, ON (Hybr, CA +12 more… Mar 25, 2026
North York - Toronto, ON (Hybr, CA +12 more… Mar 25, 2026
Organizational Design Manager
Organizational Design Manager North York - Toronto, ON (Hybr, CA +9 more… Mar 31, 2026
North York - Toronto, ON (Hybr, CA +9 more… Mar 31, 2026
Senior Human Resources Business Partner
Senior Human Resources Business Partner North York - Toronto, ON (Hybr, CA +2 more… Mar 25, 2026
North York - Toronto, ON (Hybr, CA +2 more… Mar 25, 2026
Claims Adjuster Level 3 - Accident Benefits
Claims Adjuster Level 3 - Accident Benefits North York - Toronto, ON (Hybr, CA +2 more… Apr 7, 2026
North York - Toronto, ON (Hybr, CA +2 more… Apr 7, 2026
(*) Senior Actuarial Consultant / Actuarial Consultant - Personal Auto
(*) Senior Actuarial Consultant / Actuarial Consultant - Personal Auto North York - Toronto, ON (Hybr, CA +14 more… Apr 14, 2026
North York - Toronto, ON (Hybr, CA +14 more… Apr 14, 2026
Claims Adjuster 3 - Casualty
Claims Adjuster 3 - Casualty North York - Toronto, ON (Hybr, CA +2 more… Apr 9, 2026
North York - Toronto, ON (Hybr, CA +2 more… Apr 9, 2026
Senior Business Development Representative
Senior Business Development Representative North York - Toronto, ON (Hybr, CA +1 more… Apr 13, 2026
North York - Toronto, ON (Hybr, CA +1 more… Apr 13, 2026
Director, Regional Business Development - Ontario
Director, Regional Business Development - Ontario North York - Toronto, ON (Hybr, CA +2 more… Apr 8, 2026
North York - Toronto, ON (Hybr, CA +2 more… Apr 8, 2026
Director, Compliance, Risk and Controls - Personal Lines
Director, Compliance, Risk and Controls - Personal Lines North York - Toronto, ON (Hybr, CA +9 more… Mar 27, 2026
North York - Toronto, ON (Hybr, CA +9 more… Mar 27, 2026