Senior Technology Strategy Manager (6 month Contract)

Definity Insurance Company•Toronto, ON

6d•CA$106,500 - CA$156,500•Hybrid

About The Position

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.

Requirements

7+ years of technology strategy experience from a top-tier management consulting firm.
Management consulting experience is required.
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.

Nice To Haves

Experience in key technology domains; AI, Cloud and Tech Operations is an asset.
P&C insurance industry experience is desired but not necessary.

Responsibilities

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.