Assistant, Executive

We are seeking a highly organized, detail-oriented, and forward-thinking Executive Assistant to support our Executive Vice President (Commercial Insurance). 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 EVP to focus on commercial business strategy.

The ideal candidate is a proactive self-starter who thrives in a fast-paced, high-growth environment. You are comfortable with complexity, energized by change, and fluent in modern technology. You bring sound judgment, a solutions-oriented mindset, exceptional communication skills, and the ability to anticipate the needs of senior leaders and their stakeholders.

Candidates must be available to work on‑site five days per week at our office located at 333 Bay Street, Toronto.

What can you expect in this role?

Own and optimize the EVP’s complex and dynamic calendar. With a clear understanding of business priorities and deliverables, you will thoughtfully sequence meetings, resolve conflicts, and proactively anticipate scheduling needs across a diverse group of internal leaders, C‑suite partners, and external stakeholders.

Plan and manage detailed domestic and international travel, including flights, accommodations, ground transportation, and visa requirements. Ensure timely, accurate expense reporting with exceptional attention to detail.

Serve as a trusted liaison and gatekeeper, triaging incoming communications and requests. Draft, review, and manage high‑level correspondence, ensuring clarity, professionalism, and alignment with the EVP’s voice, priorities, and brand.

Lead the planning and execution of internal and external meetings, off‑sites, technical summits, and strategic events. Coordinate logistics, prepare briefing materials, and drive clear follow‑up to ensure outcomes and accountability.

Maintain highly organized digital and physical filing systems so that key documents, research, and data are easily accessible, secure, and current. Track critical deliverables, deadlines, and preparatory materials to ensure the EVP is consistently informed and prepared.

Position requires access to non‑public, confidential, and sensitive information and the ability to maintain strict confidentiality at all times.

Build strong, trusted relationships across the organization and with external partners, representing the EVP’s office with professionalism, credibility, and a deep understanding of stakeholder needs.

Continuously seek opportunities to improve efficiency and impact by streamlining processes, enhancing communication flows, and introducing smart, scalable solutions.

Think several steps ahead by proactively identifying risks, surfacing potential issues, and proposing solutions—such as reserving required resources or flagging upcoming deadlines.

Perform additional administrative responsibilities as needed to support the EVP and broader leadership team.

What do you bring to the role?

5+ years of experience as an Executive Assistant supporting C‑level or senior executives, ideally within a fast‑paced organization.

College diploma or equivalent combination of education and relevant professional experience.

Exceptional organizational skills with the ability to manage multiple priorities simultaneously while maintaining accuracy and high standards.

Strong written and verbal communication skills, with the confidence to engage effectively at all organizational levels.

Proficiency with modern office tools, including Microsoft Office 365 (Outlook/Calendar, Word, Excel, PowerPoint).

Demonstrated ability to handle highly confidential information with professionalism, sound judgment, and discretion.

A proactive, self‑directed approach with the ability to anticipate needs, identify gaps, and propose solutions with minimal oversight.

Comfort operating in a dynamic, evolving environment, adapting quickly to changing priorities and tight timelines.

Strong interpersonal skills, including the ability to build rapport, influence without authority, and collaborate effectively across diverse work styles and personalities.

Salary Range
$59,300 - $109,200

Actual salary for…