Executive Assistant to the Chief Technology Officer Job at Randstad (Toronto)

Executive Assistant to the Chief Technology Officer

Randstad

Location:
Canada , Toronto

Category:
Office Administration

Contract Type:
Employment contract

Salary:

58000.00 - 100000.00 CAD / Year

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Job Description:

Randstad Staffing is currently looking for experienced Executive Assistants to join one of our top insurance clients in Toronto to support their Chief Technology Officer (CTO). We are seeking a highly organized, detail-oriented, and forward-thinking Executive Assistant. In this role, 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.

Job Responsibility:

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

Requirements:

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

What we offer:

Full time, Permanent role
Company share ownership program
Pension and savings programs, with company-matched RRSP contributions
Paid volunteer days and company matching on charitable donations
Educational resources, tuition assistance, and paid time off to study for exams
Focus on inclusion with employee groups, support for gender affirmation surgery, access to BIPOC counsellors, access to programs for working parents
Wellness and recognition programs
Discounts on products and services

Additional Information:

Job Posted:
January 20, 2026

Expiration:
March 08, 2026

Employment Type:

Fulltime

Work Type:

Hybrid work

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