Remote Executive Assistant to CEO – Path to Chief of Staff

Trivium; Toronto; Remote; CAD 99,000 - 156,000; Full time

Benefits offered by this job

Fully remote

1099 contractor

Growth path to Chief of Staff

Mentorship from CEO

High-impact exposure

Job summary

Trivium, a fast-growing founder-led company, is seeking a remote Executive Assistant to work directly with the CEO. This role is hands-on, high-impact and designed to buy back the CEO’s time by owning calendars, inbox, reporting, and travel logistics.

You will build structure, push back when needed, and operate with ownership in a dynamic environment, supporting high-value content, strategy, and client work while maintaining discretion and a strong operational backbone.

Qualifications

• 3+ years as an Executive Assistant or Chief of Staff to a founder/CEO.
• Proven remote experience supporting a senior executive.
• Fluent written and spoken English with strong communication.
• Able to work US Eastern Time business hours consistently with reliable internet.

Responsibilities

• Own and defend the CEO's calendar, prioritizing high-value work.
• Triage inbox, flag items for CEO and close loops.
• Track deliverables, approvals and decisions across the team.
• Prepare briefing notes for calls, update CRM and scheduling follow-ups.
• Coordinate travel, admin tasks, and expense tracking.
• Build and maintain operating systems, trackers and SOPs.

Skills

Fluent English

Remote experience

Calendar management

Operational systems

Tools

Google Workspace

Slack

CRM

Notion/ClickUp

AI assistants

Job description

Trivium, a fast-growing founder-led company, is seeking a remote Executive Assistant to work directly with the CEO. This role is hands-on, high-impact and designed to buy back the CEO’s time by owning calendars, inbox, reporting, and travel logistics.

You will build structure, push back when needed, and operate with ownership in a dynamic environment, supporting high-value content, strategy, and client work while maintaining discretion and a strong operational backbone.