Strategic Executive Assistant to CEO | Hybrid & Global Impact

Raising The Village; Toronto; Hybrid; CAD 70,000 - 90,000; Full time

Job summary

Raising The Village in Toronto is seeking an Executive Assistant to enable the Founder and CEO's effectiveness through high-level administrative and operational support in a hybrid setting.

You will manage calendars and inboxes, coordinate travel and meetings, prepare briefing materials, and support board interactions while maintaining confidentiality and adapting to shifting priorities to keep the CEO focused on strategy and impact.

Qualifications

• 5+ years of progressive executive support experience, ideally supporting a CEO or senior leader.
• Exceptional organization and prioritization skills for high-volume calendars and multiple workstreams.
• Sound judgment, discretion, and independence with confidential information.
• Resourcefulness in anticipating needs and solving issues with limited direction.
• Adaptability when priorities shift and strong follow-through.

Responsibilities

• Actively manage the CEO’s calendar and inbox across multiple time zones.
• Anticipate conflicts and determine what requires CEO attention or delegation.
• Draft executive correspondence, briefing notes, agendas, and updates in the CEO’s voice.
• Prepare the CEO for meetings by synthesizing context and highlighting decisions.
• Maintain organized executive records and protect confidential information.
• Coordinate meetings with the Executive Leadership Team and Board, track actions to completion.
• Arrange complex domestic and international travel and prepare travel briefs.
• Oversee expense reporting and support IT and office operations.
• Support special projects with concise summaries and coordinated inputs.

Skills

Executive support

Calendar management

Communication

Discretion

Project coordination

Time management

Tools

Microsoft 365

Outlook

Teams

Word

PowerPoint

Excel

Job description

Raising The Village in Toronto is seeking an Executive Assistant to enable the Founder and CEO's effectiveness through high-level administrative and operational support in a hybrid setting.

You will manage calendars and inboxes, coordinate travel and meetings, prepare briefing materials, and support board interactions while maintaining confidentiality and adapting to shifting priorities to keep the CEO focused on strategy and impact.