Executive Assistant - CEO

IGM US Holdings, Inc.; Toronto; Hybrid; CAD 80,000 - 100,000; Full time

Job summary

A dynamic corporate group in Toronto is seeking a proactive Executive Assistant to support the CEO in both business and personal domains. The ideal candidate thrives in ambiguity, manages complex calendars, and communicates with clarity and urgency. This role requires elite coordination skills, discretion, and the ability to anticipate needs. Flexibility for on-site and remote work as per the CEO's schedule is essential. Join an environment that values initiative and operational excellence.

Qualifications

• 5+ years supporting a C-suite executive in high-intensity environments.
• Experience managing complex travel schedules and high-volume calendars.
• Proactive to the point of being anticipatory.

Responsibilities

• Manage and optimize the CEO’s calendar and priorities.
• Plan and oversee travel for the CEO.
• Serve as a central hub for communication and maintain information flow.
• Build systems and processes for operational excellence.

Skills

Elite coordination skills

Exceptional written and verbal communication

Discretion and handling confidential matters

Tech-savvy across modern tools and AI

Ability to manage multiple priorities

Job description

About Gravity

Gravity is the platform public agencies use to manage budgeting, automate financial reporting, and meet compliance with confidence. From Annual Comprehensive Financial Reports (ACFR) to Budget Books to GASB disclosures, we give teams the tools to move faster, work smarter, and build public trust.

About the Role

We are seeking a world‑class Executive Assistant who operates several steps ahead, communicates with clarity and urgency, and brings exceptional foresight to a fast‑moving environment. This role directly supports the CEO across business and personal domains and acts as a stabilizing force that ensures his time, priorities, and obligations are fully optimized.

This is not a “tasks‑only” role—this is a high‑autonomy, high‑trust partnership. The ideal candidate thrives in ambiguity, anticipates needs before they are spoken, and ensures nothing falls through the cracks.

On‑site presence is required whenever the CEO is on‑site.

This may be anywhere from 5 days per week to 2 days per week, depending on his schedule. On days when the CEO is working remotely or traveling, your work can be performed off‑site. Flexibility and availability are essential.

If you bring elite coordination skills, judgment you can’t teach, and a calm, direct communication style—this role is for you.

What You’ll Do

Executive Support (CEO)

• Manage and optimize the CEO’s calendar, priorities, inbox, and daily flow—ensuring he is always prepared and running ahead of schedule.
• Anticipate needs before they arise; identify gaps, risks, and follow-ups without being asked.
• Communicate proactively, clearly, and consistently—never leaving open loops.
• Serve as the CEO’s operational anchor: scheduling, travel planning, logistics, document prep, and deadline tracking.
• Coordinate offsites, retreats, and internal team gatherings with precision and polish.
• Keep information moving across the organization while maintaining strict confidentiality.

Personal Coordination

• Plan and oversee all travel for the CEO’s, including accommodations, itineraries, calendar management, and mid‑trip communication.
• Act as the main point of contact while traveling—ensuring he has what he needs and that home logistics are handled seamlessly.
• Oversee and coordinate schedules, transportation, activities, and commitments.
• Ensure household, personal, and logistical matters are proactively addressed so the family can focus on what matters most.

Operational & Communication Excellence

• Serve as a central hub for communication—filtering noise, escalating only what matters, and ensuring fast, accurate information flow.
• Translate ambiguity into actionable plans with clear deadlines.
• Build systems, processes, and checklists that keep everything running smoothly.
• Maintain a calm presence and solution‑oriented mindset in fast‑paced, high‑pressure situations.

What You’ll Bring

• 5+ years supporting a C‑suite executive (startup, private equity, venture‑backed, or high‑intensity environment preferred).
• Proven experience owning complex travel schedules, high‑volume calendars, and personal/executive support.
• Exceptional written and verbal communication skills.
• Flawless judgment, maturity, and discretion—handling confidential matters with care.
• Ability to manage multiple competing priorities without dropping details.
• Highly self‑driven; thrives in high‑autonomy roles with limited instruction.
• Tech‑savvy across modern tools and AI.

About you

• You think five steps ahead—preventing problems before anyone knows they exist.
• You rarely need to be told something twice; you build reliable systems and habits.
• You communicate directly, professionally, and efficiently.
• You stay composed and positive, even when priorities shift or tension rises.
• You make the CEO’s life easier by default—not by instruction.
• You have extreme common sense.
• You are proactive to the point of being anticipatory.