We are seeking a highly skilled, trustworthy, and detail-oriented Executive Assistant to support a philanthropic and entrepreneurial business leader. This is a dynamic role that goes beyond traditional administrative duties—requiring intellectual curiosity, discretion, strong interpersonal instincts, and the ability to navigate fast-paced and high-pressure environments.

You'll be working at the intersection of business, philanthropy, and community leadership—providing direct support in managing professional and personal affairs, interpreting and summarizing complex documents, handling sensitive financial data, and potentially attending public and board events with the executive.

ESSENTIAL FUNCTIONS

Administrative & Executive Support

• Manage complex calendars, scheduling, and travel logistics across professional and personal commitments.
• Prepare, edit, and summarize correspondence, reports, and presentations—many involving confidential or complex subject matter.
• Attend key meetings and events, taking notes, capturing action items, and translating them into effective follow-ups.

Board & Philanthropic Support

• Provide direct support for activities related to multiple board commitments and philanthropic initiatives.
• Draft and edit board submissions, proposals, and donor communications.
• Liaise with non-profit and corporate partners on behalf of the executive.

Financial & Document Management

• Access and reconcile personal and professional banking information.
• Process cheque requisitions and track charitable donations and related tax documentation.
• Read, understand, and summarize complex contracts, grant agreements, and investment reports.

Public Engagement & Event Participation

• Accompany the executive to public and private events, capturing insights and observations in real time.
• Serve as a discreet liaison with event organizers, partners, and community members.
• Manage guest lists, follow-up communications, and event notes.

Relationship Management

• Interface with a diverse range of stakeholders including board members, philanthropic partners, staff, and service providers.
• Navigate complex personalities with professionalism, particularly high-performing, assertive individuals.
• Represent the executive's voice and intent when managing sensitive communications.