Executive Assistant
Trivium · Canada · 2026-08-28
About this role
Executive Assistant / Life Manager
Location: Remote
Type: Full-time, 1099 contractor
Compensation: $50,000–$60,000/year, based on experience
Hours: 9–5 EST, with availability outside of them for urgent things
Reports to: The founder
About the role
We are a marketing agency run by a founder who moves fast and has a lot going on. He is looking for his first Executive Assistant / Life Manager — someone who takes both the business admin and the personal logistics off his plate entirely.
There is no system in place today. You are not inheriting someone else's process; you're building one and then running it so well that he stops thinking about logistics altogether. He does not want to micromanage — he wants to hand something over and see it done.
What you'll own
• Travel: booking flights, hotels and full itineraries.
• Calendar & scheduling: managing his calendar end to end and keeping him ahead of what's coming.
• Inbox & communication: triaging email, surfacing what matters, handling the rest.
• Meeting prep: agendas, briefing notes and follow-ups so nothing gets lost between calls.
• Project tracking: he runs many projects at once — you keep the list, the deadlines and the follow-ups straight.
• Expenses & finance admin: expense reports, reimbursements, and regular communication with his accountant.
• Personal & household: appointments, medical scheduling, personal orders and shopping, groceries, and coordinating cleaners, maintenance and vendors.
• Ad hoc support for a small team of three when it's reasonable.
Requirements
Who you are
• 3+ years as an executive assistant, personal assistant or in a comparable service-driven role. Exceptional candidates with less experience and clear evidence of ownership will be considered.
• US-based. Miami preferred, with the ability to be on site around two days a week.
• Deeply organised and detail-obsessed — you track everything and nothing falls through the cracks.
• Resourceful above all. Given a goal, you figure out the how. You try first and ask second; you don't need to be walked through every task.
• Proactive — you handle things before you're asked.
• Independent. You'll get autonomy and be judged on results, not hours logged.
• Calm and easy to work with; plans change often.
• Discreet and trustworthy — you'll have access to personal and financial information.
• Comfortable with technology and quick to learn new tools; the business runs on Airtable and GoHighLevel.
• Excellent written and spoken English.
Nice to have
• Project management or operations experience.
• Experience in or around a marketing/creative agency.
• Experience supporting a founder directly
Benefits
What's on offer
• Direct, close working relationship with a founder who gives real autonomy and real trust.
• A role you get to design — you're building the system, not maintaining someone else's.
• Genuine variety: business admin one hour, personal logistics the next.
• Flexible, low-bureaucracy environment — time off is handled by conversation, not policy.
Skills asked for
- rest
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