Executive Assistant to CEO

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

EXECUTIVE ASSISTANT TO THE CEO

Fully remote | Full-time, 1099/ contractor | Monday-Friday, US Eastern Time business hours, with availability for urgent items

ABOUT THE ROLE

A fast-growing, founder-led company is hiring a remote Executive Assistant to work directly alongside its CEO.

The CEO is growing fast on social media, personally runs the company's highest-value sales, and is also the creative strategist on client ad accounts. This role exists to remove those bottlenecks: organize him, protect his time and keep everything moving, so he can focus on content and on selling to high-net-worth clients.

This is not a passive support role. The CEO wants a partner who builds the structure, holds him to it and tells him what he needs to hear.

The single goal of this role is to buy back the CEO's time.

This role is focused on the business. Household and family logistics are handled by a separate on-site Life Manager.

KEY RESPONSIBILITIES

Calendar and priorities

• - Own and defend the CEO's calendar. Build the day around his highest-value work (content, high-value sales calls, consultations) and hold him to it.
• - Run a daily priority list so nothing important gets pushed aside by noise.
• - Triage the inbox and messages: handle what you can, flag what needs him, and close loops.

Removing bottlenecks

• - Track every deliverable, approval and decision waiting on the CEO, including creative strategy for client ad accounts, and drive turnaround so client work does not stall.
• - Act as the single intake point for company reporting: collect, review and present short digests instead of passing raw reports through.
• - Coordinate follow-ups across the team so approvals and decisions keep moving.

Sales, content and offers support

• - Schedule and prepare high-value sales calls, consultations and coaching calls: briefing notes beforehand, CRM updates and follow-ups afterwards.
• - Keep the social media content pipeline on schedule: recording blocks, coordination with editors and the team, and the publishing calendar.
• - Support the launch and delivery of new offers (coaching, consultations): scheduling, documents and logistics.

Travel and administration

• - Book business travel and build itineraries.
• - Handle business admin: documents, agreements, expense tracking.

Systems and tools

• - Build and maintain the operating layer: trackers, SOPs, checklists and recurring process documentation.
• - Expected fluency: Google Workspace, Slack, a project management tool (ClickUp, Notion or equivalent), a CRM, spreadsheets, and daily use of AI assistants.

WHAT SUCCESS LOOKS LIKE

In the first 90 days you have taken the calendar, inbox triage and reporting flow off the CEO's plate, there is a live tracker of everything waiting on him, and client creative work no longer sits on his desk for weeks.

By 6-12 months you are the CEO's right hand: the business runs on a weekly rhythm you built, nothing depends on him remembering it, and his time goes to content and high-value sales.

IDEAL CANDIDATE

• - 3+ years as an Executive Assistant, Chief of Staff or equivalent to a founder, CEO or senior executive, ideally in a fast-growing or entrepreneurial company.
• - Proven remote experience: you have run an executive's day without being in the room.
• - Fluent professional English, written and spoken.
• - Able to work US Eastern Time business hours consistently, with reliable internet and a quiet workspace.
• - Strong administrative and operational backbone. You build systems, you don't just follow them.
• - Exceptionally discretion with confidential business and financial information.
• - Tech-savvy: you master Google Workspace, Slack, a project management tool (ClickUp, Notion or equivalent), a CRM, spreadsheets, and daily use of AI assistants.

You will thrive here if

• - You are direct, unflappable and comfortable with a straightforward, high-energy, fast-moving principal. Feedback is candid and immediate, and nothing is personal.
• - You are willing to push back and tell the CEO what he needs to hear. He wants a partner who holds him accountable, not someone who waits for instructions.
• - You are energized by walking into disorder and creating structure.

Nice to have

• - Experience in a marketing agency, paid ads or creative production environment.
• - Social media or content operations experience.
• - Experience supporting a founder who sells coaching, consulting or premium offers.

WHY THIS ROLE

• - Employment type: full-time 1099 independent contractor
• - Paid Time Off and fully remote
• - Growth: direct mentorship from the CEO and a clear path to grow into a Chief of Staff position
• - Network: exposure to high-impact leaders

Complete discretion and confidentiality are required. The people who succeed in this seat enjoy managing complexity and operate with a high level of ownership in a dynamic, sometimes chaotic environment.