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About the Role

The AVP, Strategic Technology Delivery – Claims is responsible for defining and delivering the strategic technology roadmap for Claims and Customer Interaction (CI), serving as the key link between business strategy and technology execution. This role oversees the development of technology solutions, business cases, and delivery strategies that support digital transformation and operational excellence, driving the end-to-end delivery of complex technology and business transformation initiatives.

Responsibilities

Partner with Claims leadership to align technology initiatives with business strategy, transformation goals, and operational priorities.
Develop and maintain the strategic technology roadmap and portfolio for Claims and Customer Interaction (CI).
Lead the development of business cases, investment proposals, and funding recommendations for large-scale technology initiatives.
Collaborate with Architecture, Data, Cybersecurity, Infrastructure, and Platform teams to define sustainable technology solutions.
Oversee the end-to-end delivery of complex technology and business transformation programs.
Ensure initiatives are delivered on time, within budget, and aligned with expected business outcomes and benefits.
Drive agile delivery practices, continuous improvement, and operational excellence across technology initiatives.
Monitor program performance, risks, dependencies, and delivery health, providing executive-level reporting and governance.
Build and lead high-performing cross-functional teams, fostering a culture of accountability, innovation, and customer-centric delivery.
Lead organizational change and transformation efforts, ensuring stakeholder readiness, adoption, and realization of strategic business outcomes.

Requirements

Bachelor’s or Master’s degree in Computer Science, Information Technology, Engineering, Business Administration, or a related field.
12+ years of progressive leadership experience in technology delivery, program management, application development, or business transformation.
Proven track record leading large-scale strategic programs, portfolios, and enterprise-wide transformation initiatives.
Strong experience operating within Agile, Product, and DevOps environments.
Demonstrated ability to lead and influence cross-functional, matrixed teams across business and technology functions.
Experience developing business cases, securing funding, and presenting recommendations to executive leadership and governance committees.
Strong stakeholder management skills, with the ability to build partnerships across business, technology, and vendor organizations.
Experience managing technology vendors, consulting partners, and strategic supplier relationships.
Strong strategic thinking, execution, and change leadership capabilities.
Insurance industry experience, particularly within Claims, Customer Operations, or Digital Channels, is preferred.
Successful clearance of background checks (including criminal checks and leadership references).

Skills

Agile
Product
DevOps
Stakeholder Management
Strategic Thinking
Execution
Change Leadership

Location

Hybrid

Work Type

Hybrid

Experience Level

12+ years of progressive leadership experience

Education Level

Bachelor’s or Master’s degree in Computer Science, Information Technology, Engineering, Business Administration, or a related field.

Salary/Compensations

$166,500-$216,500

Benefits

Hybrid work schedule for most roles
Company share ownership program
Incentive Program
Pension and savings programs, with company-matched RRSP contributions
Paid volunteer days and company matching on charitable donations
Educational resources, tuition assistance, and paid time off to study for exams
Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
Wellness and recognition programs
Discounts on products and services

About the Company

Definity is the parent company to some of Canada’s most long-standing and innovative insurance brands, including Economical Insurance, Sonnet Insurance, Family Insurance Solutions, and Petline Insurance. Our ambition is to be one of Canada’s leading and most innovative property and casualty insurers. We can’t do that without our people, so we embrace and encourage a culture that’s collaborative, ambitious, rewarding, and empowering.
We offer a flexible, hybrid work experience where employees work from the office and virtually depending on the type of work they are doing and who they are working with. Bring your true self and be a part of our journey. It’s better here.

Equal Opportunity

We encourage you to apply! We know from experience that a candidate doesn’t need 100% of the qualifications listed to bring incredible value to our team. We’re actively seeking diverse backgrounds and perspectives to help us make insurance better. At Definity, inclusion, diversity, and equity aren’t just “nice to have” — they’re essential to our success.
Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please let us know by contacting accessibility@economical.com.
As part of Definity’s commitment to reconciliation, we acknowledge that our work, meetings, and travel take place on the lands now known as Canada, and recognize the enduring presence, wisdom, and stewardship of the First Nations, Métis, and Inuit peoples who have long cared for these lands.