Executive Assistant to the Chief Technology Officer (CTO)

Definity Financial; Toronto; On-site; CAD 70,000 - 90,000; Full time

Job summary

A leading financial services firm in Toronto is seeking a highly organized Executive Assistant to support the CTO. The ideal candidate will have over 5 years of experience in a fast-paced environment, exceptional communication skills, and a strong ability to manage multiple priorities. This role involves managing the CTO's calendar, travel arrangements, and high-level communications, while maintaining confidentiality and supporting strategic initiatives.

Qualifications

• 5+ years of experience as an Executive Assistant supporting C-level executives.
• Must handle confidential information professionally.
• Ability to manage multiple priorities without compromising quality.

Responsibilities

• Manage the CTO’s complex calendar and prioritize meetings.
• Plan and manage travel itineraries and prepare expense reports.
• Draft and manage high-level communications on behalf of the CTO.
• Organize meetings, events, and follow-ups efficiently.

Skills

Organizational skills

Verbal communication

Written communication

Proficient with MS Office 365

Discretion

Education

College diploma or equivalent

Tools

Microsoft Office 365

Job description

Overview

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 a strategic partner, trusted advisor, and operational anchor, enabling the CTO to focus on driving innovation, technical strategy, and global leadership.

The ideal candidate is a self-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:

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/PowerPoint).
• Proven track record of handling highly confidential information with the utmost integrity and professionalism.
• A self-starter who takes initiative, anticipates needs, identifies problems, and proposes solutions with minimal oversight.
• Ability to thrive in a dynamic, rapidly evolving environment, adapting to changing priorities and tight deadlines with a positive attitude.
• Strong ability to build rapport, influence without authority, and collaborate effectively with diverse personalities and work styles.