Executive Assistant

Job Title: Executive Administrative Assistant

Location: Toronto GTA, Canada

Work Model: Remote (with occasional in-office presence approx. once per month)

Role Type: Full-time | Exclusive Opportunity

Position Overview

We are seeking a highly poised, strategic, and proactive Executive Administrative Assistant to provide high-level administrative, organizational, and operational support to two senior leaders - one aligned to Pacific Standard Time (PST) and the other to Eastern Standard Time (EST).

This is a high-visibility, remote-first role designed for an executive partner who excels at managing competing priorities across multiple time zones, navigating dynamic calendars, and serving as a trusted extension of senior leadership. The ideal candidate will combine exceptional communication skills and razor-sharp attention to detail with the discretion required to handle sensitive enterprise information.

Key Responsibilities

• Multi-Executive Support: Deliver comprehensive administrative and operational partnership to two senior leaders, seamlessly balancing time-zone demands across PST and EST.
• Complex Calendar & Schedule Management: Proactively manage fluid, high-volume calendars, resolving scheduling conflicts across multiple regions and anticipating downstream impacts.
• Meeting & Event Logistics: Coordinate internal and executive engagements; oversee agendas, preparation decks, pre-read materials, room/virtual setups, and action-item tracking for prompt follow-through.
• Travel & Expense Management: Build comprehensive domestic and international travel itineraries, manage accommodations, clear logistics, and execute accurate expense reporting.
• Strategic Communication & Gatekeeping: Monitor and prioritize incoming communications, flag critical issues requiring immediate executive attention, and handle senior-level inquiries with tact and diplomacy.
• Document & Deck Preparation: Draft, compile, and format high-level executive presentations, status reports, briefing notes, and confidential documents using Microsoft 365.
• Stakeholder & Project Coordination: Act as a central, polished point of contact connecting executives with cross-functional teams, external partners, and enterprise leaders.
• Confidentiality & Discretion: Manage highly sensitive business decisions, personnel information, and organizational strategies with flawless discretion.

Required Qualifications

• 7+ years of progressive Executive Assistant experience supporting C-suite executives, Vice Presidents, or senior enterprise leaders.
• Proven track record of managing complex, high-volume schedules for multiple executives simultaneously across different time zones (PST and EST focus).
• Advanced mastery of Microsoft 365 (Outlook, Teams, PowerPoint, Excel, Word, and SharePoint).
• Exceptional verbal and written communication skills, with a polished, executive-ready presentation.
• Demonstrated ability to operate independently in a remote setting while staying highly connected to business needs.
• Superior organizational agility, sound judgment, and acute attention to detail.
• Location requirement: Based in the Toronto GTA with flexibility to attend in-person meetings/office events approximately once per month.

Preferred Qualifications

• Experience working within a large corporate, enterprise, or high-growth technology environment.
• Deep background handling confidential business operations and strategic executive correspondence.
• Experience in project management and action-tracking methodologies.