Executive Assistant (supporting multiple executives experience as an EA is required)

WorkStaff360•Toronto, ON

27d•Remote

About The Position

We are seeking an experienced Executive Assistant to provide comprehensive support to multiple executives in a fast-paced, high-growth environment. This role requires exceptional organizational skills, discretion, and the ability to manage complex calendars, coordinate meetings, and handle domestic and international travel arrangements. The ideal candidate will be a proactive problem-solver, adept at managing competing priorities and maintaining confidentiality. This is a remote freelance position requiring advanced proficiency in modern productivity tools and strong self-discipline.

Requirements

5+ years of experience as an Executive Assistant, with at least 2 years supporting C- suite or senior executive leadership.
Experience supporting multiple executives simultaneously in a high-growth or fast-paced environment.
Exceptional written and verbal communication skills; able to represent executives professionally to internal and external stakeholders. Advanced fluency in English (reading and writing) is essential to this role.
Experience supporting executives across multiple time zones, including international travel coordination.
Outstanding organizational skills with meticulous attention to detail and a proven ability to manage competing priorities.
High degree of discretion, integrity, and experience handling highly confidential information.
Proven ability to work independently in a fully remote environment, with strong self-discipline and ownership; consistently maintaining a high level of visibility and responsiveness.
Advanced proficiency with modern productivity and collaboration tools, including Google Workspace or Microsoft 365, Zoom, and Slack.

Responsibilities

Own complex, ever-shifting calendars across multiple executives and time zones, resolving conflicts proactively, and protecting focus time.
Coordinate internal and external meetings, including customer meetings, cross- functional leadership sessions, and candidate interviews in a timely manner.
Prepare/ Provide agendas, meeting/ conference materials, and industry conference registrations as needed.
Plan and book domestic and international travel, including flights, lodging, and ground transportation.
Anticipate and resolve travel disruptions in real time, acting as the first line of defense when plans change.
Manage expense reports, receipts, and reimbursements in a timely and accurate manner.
Serve as a gatekeeper and first point of contact for members of the executive team, exercising strong judgment about what requires their attention.
Draft, proofread, and send professional communications on behalf of executives.
Maintain clear, timely follow-up on action items, decisions, and commitments, giving special attention to customer outreach efforts.
Collaborate with other EAs to organize leadership offsites, team events and meetings, from agenda development to logistics and follow-up.
Prepare agendas, take meeting notes, track action items, and drive accountability on deliverables.
Partner with internal and external stakeholders to coordinate customer and partner meetings.
Provide back up support for EA team when out on PTO as needed.
Support special projects for the executive team, such as preparing meeting materials and internal communications.
Maintain confidential files, contracts, and documents with a high degree of accuracy and discretion.
Continuously identify opportunities and new tools (such as AI) to improve processes and workflows that support EA and executive effectiveness.