Executive Assistant to the Chief Technology Officer (CTO)

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 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:

• 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.
  
  
  

Interested in this role, but don't meet every requirement? We encourage you to apply! We know from experience that a candidate doesn't need 100% of the qualifications listed to bring incredible value to our team. We're actively seeking diverse backgrounds and perspectives to help us make insurance better. At Definity, inclusion, diversity, and equity aren't just "nice to have" — they're essential to our success.

What's in it for you?

• Hybrid work schedule for most roles
• 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
  
  
  

Actual salary for the role may vary depending on work location of the successful candidate and other factors including but not limited to, skills, education, experience, working conditions and the local labour market.  In addition to base pay, eligible employees may participate in various incentive plans which are paid out at the discretion of the company and subject to individual and company performance.

Go ahead and expect a lot — you deserve it.

It's better here — but don't take our word for it. Definity was named by Great Place to Work as one of the Best Workplaces in Canada for women, for youth, and for inclusion.

Our inclusive work environment welcomes diversity and supports accessibility. If you require accommodation at any time during the recruitment process, please let us know by contacting [email protected].

Background checks

This role requires successful clearance of background checks (including criminal checks and leadership references).