Toronto, ONT, Canada

Be the First to Apply 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.

The Opportunity Senior Manager, Technology Strategy is a highly visible leader responsible for shaping and advancing Technology Solutions' strategic direction. Reporting to the AVP, Technology Strategy & Communications, this role partners with senior leaders to evaluate emerging opportunities,providestrategic insights, and develop recommendations that drive long‑term business value and competitive advantage.

The role plays a key part in the development and evolution of Definity's technology strategy, bringing together market intelligence, industry trends, business priorities, and technology capabilities to inform investment decisions and future direction. Through rigorous analysis, structured problem-solving, and stakeholder engagement, the Senior Manager helps translate strategicobjectivesinto actionable prioritiesand investment decisions.

As a trusted advisor to Technology Solutions leadership, the Senior Manager develops executive communications, strategic narratives, and Board‑level materials that support decision‑making, organizational alignment, and effective communication of technology priorities across the enterprise

What to Expect

Lead the development and ongoing evolution of the Technology Solutions AI strategy, ensuring alignment with enterpriseobjectives, business priorities,and industry trends.





Monitor external market developments, emerging technologies, competitive benchmarks, and AI advancements toidentifyopportunities and risks and provide strategic recommendations to senior leadership

Identify, assess, and recommend AI opportunities across the enterprise, including agentic AI, automation, and technology productivity initiatives

Research, analyze, and synthesize internal and external technology trends to inform strategic direction and investment decisions

Facilitatestrategicworking sessions with a broad range of functional stakeholders

Developstrategic recommendationsandexecutive-ready materials that supportexecutivedecisionsand strategic direction

Support technology quarterly business reviews (QBRs), strategy reviews, and executive forums throughstoryboarding, content development, and executive-ready materials

Lead development of executive communications that support Technology Solutions priorities, strategic initiatives, and organizational objectives

Create compelling presentations,briefingmaterials, speaking notes,reportsand leadership updates for the CTO, ELT, Board of Directors, and other senior stakeholders

Coordinate messaging across Technology Solutions and key partner teams to ensure consistency, alignment, and stakeholder engagement

Supportexecutiveevents, town halls, strategy sessions, offsites, and employee communications that strengthen organizational understanding and adoption of strategic priorities

What you Bring

7+years oftechnologystrategyexperiencefrom atop-tiermanagement consultingfirm

Management consulting experience isrequired

Experience in key technology domains;AI,Cloudand Tech Operations isan asset





Demonstrated ability to influence outcomes and drive alignment across multiple teams and stakeholders without direct authority

Proven ability to learn quickly and gainexpertisein new functional areas

Acute attention to detail and strong commitment to producing excellent work products

Experience in evaluating current opportunitiesand the ability to connect technical concepts to business concepts

Strong businessand technologyacumen, withdemonstratedaptitude for strategic,analytical,and critical thinking

Strong executive presence with the ability tofacilitatediscussions, challenge thinking, and influence decision-making with senior leaders

Expertproficiencyin Microsoft PowerPoint and Excel isrequired

P&C; insurance industry experience is desired but not necessary

Salary Range $106,500-$156,500

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.

This position is being posted to fill an existing vacancy.

We also take potential into consideration. If you don’t have this exact experience, but you know you have what it takes, be sure to give us more insight through your application and cover letter.

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 [email protected].

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.

Background checks This role requires successful clearance of a background check (including criminal checks and leadership references).

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📌 Senior Technology Strategy Manager (6 month Contract) (Toronto)
🏢 Definity Financial
📍 Toronto