Executive and Personal Assistant

Position Overview

This role is for an experienced Executive and Personal Assistant supporting a senior leader in a fast-moving private organization with interests in hospitality, philanthropy, investment work, and special projects. The position is based in downtown Toronto with a hybrid schedule that requires 1–2 days onsite each week. It is a hands-on role for someone who wants to act as a strategic partner rather than provide only traditional administrative support.

The successful candidate will help keep priorities on track, manage sensitive information with care, coordinate across multiple initiatives, and contribute ideas while taking ownership of projects from start to finish. This opportunity is well suited to someone aiming to grow into a Chief of Staff-type path and who values broad exposure, autonomy, and professional growth.

Work Arrangement and Location

Downtown Toronto, Ontario, Canada. Hybrid setup with 1–2 days per week in the office.

Language Requirement

Outstanding written and spoken English is required.

Background Check

Before hire, candidates must complete a criminal record check, employment verification, and provide two professional references.

Compensation and Benefits

The compensation range is $70,000 to $90,000 per year, depending on experience. Benefits include comprehensive health and dental coverage after three months, three weeks of vacation, and eligibility for a discretionary bonus program.

What the Role Involves

This position combines executive support, project coordination, research, stakeholder communication, and administrative oversight. You will work closely with a highly engaged and entrepreneurial executive, supporting day-to-day priorities while helping advance broader business and community initiatives.

Why This Opportunity Stands Out

You will have direct access to a dynamic executive and leadership team, meaningful ownership of important work, and exposure to a wide range of areas including philanthropy, hospitality, business operations, investments, and special projects. The environment is collaborative and values initiative, insight, and dependable execution.

Hiring Partner Support

The recruiting partner helps candidates throughout the hiring process at no cost, including matching, coordination, advocacy, and coaching support.

Note from the Hiring Manager

The ideal candidate is curious, exceptionally organized, comfortable taking responsibility, and excited to contribute ideas while helping move key initiatives forward.

Responsibilities

• Manage a demanding and constantly changing calendar, including meetings, travel, and priority scheduling.
• Handle email flow, draft correspondence, and make sure urgent items are surfaced and addressed quickly.
• Own projects from planning through completion, including progress tracking and regular status updates.
• Assist with philanthropic work, stakeholder coordination, research tasks, and community-focused initiatives.
• Organize travel, events, presentations, and other administrative work across several areas of responsibility.
• Review documents, prepare written responses, gather information, and provide recommendations that support decision-making.
• Serve as a trusted point of contact between executives, internal teams, and outside stakeholders while protecting confidentiality.

Requirements

• Between 4 and 7 years of progressive experience as an Executive Assistant or senior administrative professional supporting executives or high-profile individuals.
• Strong attention to detail and the ability to balance several priorities at once.
• Proven project coordination skills with the ability to independently move work forward.
• Excellent written communication skills, including preparing correspondence, presentations, and executive-level materials.
• High level of discretion when dealing with confidential or sensitive information.
• Advanced ability with Microsoft Office Suite and digital collaboration platforms.
• Proactive, resourceful, and solution-oriented approach with strong interpersonal skills.

Perks

• Direct exposure to a senior executive and an influential leadership group.
• Opportunity to work across philanthropy, hospitality, operations, investment activity, and special projects.
• Collaborative culture where initiative and input are welcomed.
• Meaningful project ownership with visible impact.
• Hybrid working model with some remote flexibility.
• Health and dental benefits after three months.
• Three weeks of vacation.
• Discretionary bonus eligibility.

Additional Information

This role is intended for someone who wants to be more than a traditional assistant and is comfortable acting as a partner in decision-making and execution.