Executive Assistant to the Chief Technology Officer (CTO)

Starr Underwriting; Toronto; On-site; CAD 60,000 - 80,000; Full time

Job summary

Starr Underwriting seeks a proactive and detail-oriented Executive Assistant to support the Chief Technology Officer (CTO). This crucial role involves optimizing schedules, managing communication, and ensuring the CTO's operational effectiveness within a dynamic technological setting. Ideal candidates are self-starters with extensive experience supporting executives, exceptional organizational skills, and proficiency in modern office tools.

Qualifications

• 5+ years of experience as an Executive Assistant for C-level executives.
• Ability to manage multiple priorities without compromising quality.
• Experience with handling confidential information.

Responsibilities

• Manage the CTO's schedule and travel arrangements.
• Draft and manage high-level communications.
• Coordinate internal and external meetings.

Skills

Communication

Organization

Problem Solving

Education

College diploma or equivalent practical experience

Tools

Microsoft Office 365

Job description

We are seeking a highly organized, detail-oriented, and forward-thinkingExecutive Assistantto support ourChief 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-starterwho 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/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.