Executive Assistant to the Chief Technology Officer (CTO)

Definity; Toronto; Hybrid; CAD 60,000 - 90,000; Full time

Job summary

A leading insurance company is seeking an Executive Assistant to support their CTO in Toronto. This role emphasizes organizational skills, strategic partnership, and exceptional communication in a fast-paced environment. The ideal candidate will manage calendars, travel, and correspondence, ensuring seamless executive support.

Benefits

Hybrid work schedule

Company share ownership program

Pension and savings plans

Paid volunteer days

Educational resources and tuition support

Inclusive environment programs

Wellness and recognition programs

Product and service discounts

Qualifications

• 5+ years supporting C-level executives.
• Experience in a fast-paced technology environment.
• Ability to manage multiple priorities.

Responsibilities

• Manage and optimize the CTO’s complex calendar.
• Plan and coordinate travel arrangements.
• Act as a liaison and gatekeeper.

Skills

Organizational Skills

Communication Skills

Problem Solving

Interpersonal Skills

Education

College diploma or equivalent experience

Tools

Microsoft Office 365

Job description

Executive Assistant to the Chief Technology Officer (CTO)

Join to apply for the Executive Assistant to the Chief Technology Officer (CTO) role at Definity.

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 embrace 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 work and team needs. Bring your true self and be part of our journey. It’s better here.

We are seeking a highly organized, detail-oriented, and forward-thinking Executive Assistant to support our CTO. This role goes beyond traditional administrative tasks; you will serve as a strategic partner, trusted advisor, and operational anchor, enabling the CTO to focus on innovation, technical strategy, and leadership.

The ideal candidate is a self-starter who thrives in a fast-paced, high-growth environment. You are comfortable with technology, creative, solutions-oriented, and possess exceptional communication skills. You understand how to support and anticipate the needs of senior executives and their stakeholders.

Key Responsibilities:

• Manage and optimize the CTO’s complex calendar, prioritizing meetings, resolving conflicts, and anticipating scheduling needs across stakeholders including C-suite and external partners.
• Plan and coordinate domestic and international travel, including flights, accommodations, ground transportation, visas, and prepare expense reports accurately and promptly.
• Act as a liaison and gatekeeper, triaging communications, drafting and reviewing high-level correspondence, and ensuring professionalism and alignment with the CTO’s voice.
• Organize and execute internal and external meetings, off-sites, summits, and events, handling logistics, preparing materials, and ensuring follow-up.
• Maintain organized digital and physical filing systems, ensuring easy access to critical documents and data, and track key deliverables and deadlines.
• Handle sensitive and confidential information with discretion, integrity, and professionalism.
• Build and maintain strong relationships across the organization and with external partners, representing the CTO’s office professionally.
• Bring creativity to problem-solving, process improvements, and communication flow enhancements.
• Proactively identify opportunities, flag issues, and propose solutions, including resource planning and deadline monitoring.
• Perform other administrative duties as needed.

Qualifications:

• 5+ years supporting C-level executives, preferably in a fast-paced technology environment.
• College diploma or equivalent experience.
• Exceptional organizational skills, attention to detail, and ability to manage multiple priorities.
• Strong written and verbal communication skills.
• Proficiency with Microsoft Office 365 (Calendar, Word, Excel, PowerPoint).
• Experience handling confidential information with integrity.
• Self-motivated, proactive, and solutions-oriented.
• Ability to adapt to changing priorities and work under tight deadlines.
• Excellent interpersonal skills to build rapport and collaborate effectively.

We encourage applicants who may not meet every requirement but can bring valuable skills and perspectives. Diversity, inclusion, and equity are central to our success.

What’s in it for you?

• Hybrid work schedule
• Company share ownership program
• Pension and savings plans with company-matched RRSP contributions
• Paid volunteer days and charitable donation matching
• Educational resources, tuition support, and paid study leave
• Inclusive environment supporting gender affirmation, BIPOC counseling, and working parents
• Wellness and recognition programs
• Product and service discounts

Salary varies based on location, skills, and experience. Incentive plans may also apply.

Our inclusive environment welcomes diversity and supports accessibility. Accommodation requests during recruitment can be made by contacting [email protected].

This role requires successful background checks, including criminal and reference checks.

Additional Details

• Seniority level: Mid-Senior level
• Employment type: Full-time
• Job function: Administrative
• Industry: Insurance