Executive Assistant w / Strong Project Management Skills

Take It Easy Group; Toronto; Remote; CAD 80,000 - 100,000; Full time

Job summary

Take It Easy Group is seeking a sharp and organized Executive Assistant to support multiple clients, including founders and C-suite leaders. This full-time remote role requires a proactive individual with strong project management skills and the ability to thrive in fast-paced environments. Responsibilities include managing calendars, driving projects, and maintaining internal systems, all while anticipating needs and surfing blockers. Ideal candidates will have 5+ years in similar roles and be tech-savvy, with a preference for those based in Canada, particularly in the Pacific Time Zone.

Qualifications

• 5+ years as an Executive Assistant, Project Manager, or Chief of Staff.
• Experience in fast-moving environments like startups or agencies.
• Ability to manage competing priorities and communicate effectively.

Responsibilities

• Manage calendars, coordinate meetings, and draft communications.
• Drive cross-functional projects to completion.
• Serve as a gatekeeper and liaison between executives and stakeholders.

Skills

Project Management

Communication

Technical Savvy

Tools

Google Workspace

Slack

Notion

Asana

Job description

• Please do not reach out to the job poster - resumes will ONLY be considered through the proper application channels

About Take It Easy Group

Take It Easy is a collective of seasoned Executive Assistants and Project Managers who thrive in fast-paced, ambiguous environments. We support high-growth startups, creative agencies, and mission-driven leaders with strategic execution and operational calm. Our work is grounded in flexibility, trust, and a shared commitment to helping leaders do their best work.

About the Role

We’re hiring a sharp, highly organized Executive Assistant with strong project management skills to join our growing remote team. This full-time role will support multiple clients—think founders, C-suite leaders, and senior executives—across different industries. You'll be their right-hand partner, owning calendars, managing communications, moving projects forward, and creating systems that bring clarity to the chaos.

We’re looking for someone based in Canada (PST strongly preferred) who is comfortable in start-up or professional services environments where priorities shift quickly and no two days are the same.

Key Responsibilities

• Provide proactive executive support : manage calendars, coordinate meetings, book travel, and draft communications
• Own and drive cross-functional projects and operational workflows to completion
• Serve as a gatekeeper and liaison between executives, teams, and external stakeholders
• Maintain internal systems : organize shared drives, maintain SOPs, track deliverables
• Anticipate needs, surface blockers, and recommend improvements
• Manage competing priorities across multiple clients with clarity and calm

You Might Be a Fit If You

• Have 5+ years of experience as an Executive Assistant, Project Manager, or Chief of Staff
• Are based in Canada (strong preference for Pacific Time Zone)
• Have supported executives or teams in ambiguous, fast-moving environments (think early-stage startups, creative agencies, or consultancies)
• Communicate clearly and thoughtfully, both in writing and over Zoom
• Love streamlining messy processes and can operate independently with minimal direction
• Are tech-savvy and comfortable with tools like Google Workspace, Slack, Notion, and Asana
• Enjoy variety in your work and thrive when wearing many hats

Compensation starting at $80,000.00 / year + based on experience.

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