Senior Technology Strategy Manager (12 month Contract)

Kibbi Technologies Inc.; Toronto; Hybrid; CAD 107,000 - 157,000; Full time

Job summary

Definity is a leading Canadian P&C insurer known for its innovative insurance brands and flexible hybrid work model. The Senior Manager, Technology Strategy partners with senior leaders to evaluate opportunities, translate strategy into priorities, and drive long-term value across Technology Solutions.

In this role you will develop executive communications, financial and strategic narratives, and material for Board discussions, while overseeing AI strategy alignment with enterprise objectives

Qualifications

• 7+ years of technology strategy experience from a top-tier management consulting firm.
• Management consulting experience is required.
• Expert proficiency in Microsoft PowerPoint and Excel is required.

Responsibilities

• Lead development and evolution of the Technology Solutions AI strategy.
• Monitor external market developments, AI advancements, and industry trends to inform leadership.
• Identify and recommend AI opportunities across the enterprise, including agentic AI and automation.
• Develop executive-ready materials and strategic narratives for the CTO and Board of Directors.
• Coordinate messaging across Technology Solutions and partner teams to ensure alignment.
• Support executive events, strategy sessions, and town halls to strengthen understanding of priorities.

Skills

Technology strategy

Management consulting

Executive presence

Strategic thinking

Analytical thinking

Stakeholder influence

AI

Cloud

Tools

Microsoft PowerPoint

Microsoft Excel

Job description

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, provide strategic 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 strategic objectives into actionable priorities and 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 enterprise objectives, business priorities, and industry trends.
• Monitor external market developments, emerging technologies, competitive benchmarks, and AI advancements to identify opportunities 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.
• Facilitate strategic working sessions with a broad range of functional stakeholders.
• Develop strategic recommendations and executive-ready materials that support executive decisions and strategic direction.
• Support technology quarterly business reviews (QBRs), strategy reviews, and executive forums through storyboarding, content development, and executive-ready materials.
• Lead development of executive communications that support Technology Solutions priorities, strategic initiatives, and organizational objectives.
• Create compelling presentations, briefing materials, speaking notes, reports and 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.
• Support executive events, town halls, strategy sessions, offsites, and employee communications that strengthen organizational understanding and adoption of strategic priorities.

What you Bring

• 7+ years of technology strategy experience from a top-tier management consulting firm.
• Management consulting experience is required.
• Experience in key technology domains; AI, Cloud and Tech Operations is an asset.
• Demonstrated ability to influence outcomes and drive alignment across multiple teams and stakeholders without direct authority.
• Proven ability to learn quickly and gain expertise in new functional areas.
• Acute attention to detail and strong commitment to producing excellent work products.
• Experience in evaluating new opportunities and the ability to connect technical concepts to business concepts.
• Strong business and technology acumen, with demonstrated aptitude for strategic, analytical, and critical thinking.
• Strong executive presence with the ability to facilitate discussions, challenge thinking, and influence decision-making with senior leaders.
• Expert proficiency in Microsoft PowerPoint and Excel is required.
• 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.

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 [e-mail].

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).

#LI-Hybrid