Executive Assistant to Chief Technology Officer; CTO

Toronto, ONT, Canada

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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.

We are seeking a highly organized, detail-oriented, and forward-thinking

Executive Assistant to support our Chief Technology Officer (CTO). This is a pivotal role that goes beyond traditional administrative support. You will serve as astrategic partner, trusted advisor, and operational anchor, enabling the CTO to focus on driving innovation, technical strategy, and global leadership.

The ideal candidate is aself-starter who thrives in a fast-paced, high-growth environment. You are not only comfortable with technology, you embrace it. You bring a creative, solutions-oriented mindset, exceptional communication skills, and a deep understanding of how to support and anticipate the needs of senior executives and their stakeholders.

Key Responsibilities:

• Own and optimize the CTO’s complex calendar. With an understanding of key goals and deliverables, prioritize meetings, resolve conflicts, and proactively anticipate scheduling needs across a diverse stakeholder group including C-suite and external partners.
• Plan and manage intricate domestic and international travel itineraries, including flights, accommodations, ground transportation, and visas. Prepare accurate and timely expense reports with a high degree of precision.
• Serve as a key liaison and gatekeeper actively triaging incoming communications. Draft, review, and manage high-level communications, ensuring clarity, professionalism, and alignment with the CTO’s voice and priorities.
• Lead the planning and execution of internal and external meetings, off-sites, technical summits, and strategic events. Coordinate logistics, prepare briefing materials, and ensure seamless follow-up.
• Maintain highly organized digital and physical filing systems, ensuring critical documents, research, and data are easily accessible and secure. Track key deliverables, deadlines, and documents to ensure the CTO is always prepared and informed.
• Handle a wide range of highly sensitive and confidential information with unwavering discretion, integrity, and professionalism, including intellectual property, strategic plans, personnel matters, and pre-release technologies.
• Build and maintain strong working relationships across the organization and external partners, representing the CTO’s office with warmth, professionalism, and a deep understanding of stakeholder needs.
• Bring a creative lens to challenges. Whether it’s streamlining a process or improving a communication flow, you’re always looking for ways to enhance efficiency and impact.
• Think several steps ahead. Proactively identify opportunities, flag potential issues and propose solutions such as pre-booking necessary resourcing and monitoring upcoming deadlines.
• Other general administrative duties as needed

Qualifications:

• 5+ years of demonstrable experience as an Executive Assistant supporting C-level executives, preferably within a fast-paced technology, organization.
• A college diploma or equivalent practical experience.
• Exceptional organizational skills, meticulous attention to detail, and the ability to manage multiple priorities simultaneously without compromising quality.
• Strong written and verbal communication skills.
• Proficient with modern office suites (e.g., Microsoft Office 365 – particularly Calendar, Docs/Word, Sheets/Excel, Slides/Power Point
• Proven track record of handling highly confidential information with the utmost integrity and professionalism.
• A self-starter who…