Senior Executive Assistant

Remote · Full-Time · 6 PM to 2 AM South Africa Time

About Us

We’re a small, growing Canadian professional services firm with a remote team. We’re hiring a senior Executive Assistant to run the founder’s week and the firm’s operations desk.

About the Role

This is a senior role for someone who has run operations, not just a calendar.

You’ll own the founder’s calendar, inbox and travel, plus the operations work that keeps the firm running: client invoicing, team payroll prep, payroll and filing deadlines, hiring coordination, and making sure client requests reach the right person and get done. When the founder travels, you keep everything moving.

What You’ll Do

• Run the founder’s calendar, inbox and travel, with work and family in one place
• Triage shared client inboxes and turn requests into tracked tasks for the team
• Prepare monthly client invoicing and the team’s payroll run
• Keep payroll, remittance and year-end filing deadlines on track across clients
• Coordinate hiring, onboarding and offboarding
• Handle vendors, subscriptions, insurance and other business admin
• Follow up on open items until they close, without being asked

Who You Are

• Senior. You’ve been the person a business owner relies on to run things, not just book things.
• Decisive. You make sensible calls on the founder’s behalf and report back.
• Accurate. Invoices, payroll and calendars are right the first time.
• Organized across many deadlines at once.
• AI-fluent. You use Claude or similar tools to work faster, and you check the output.

Must-Haves

• 5+ years as an Executive Assistant, Operations Manager or similar, supporting a business owner
• Hands-on invoicing and payroll administration experience
• 3+ years of remote work
• Excellent written and spoken English
• Available full-time, Monday to Friday, 6 PM to 2 AM South Africa time (night shift)
• Reliable internet, quiet workspace, and backup power and internet
• References we can speak with

Nice-to-Haves

• Canadian payroll filings (T4, ROE, WorkSafeBC) or US payroll (W-2, 1099)
• Accounting or bookkeeping firm experience
• Managing other assistants
• Supporting a founder through extended travel

Software

If you have experience with any of the following, note it in your application:

• Google Workspace
• Claude or ChatGPT
• QuickBooks Online (QBO)
• Gusto, Wagepoint or ADP
• Wise
• Missive
• Double (formerly Keeper)
• GoHighLevel (GHL)

Logistics

• Schedule: Full-time, Monday to Friday, 6 PM to 2 AM South Africa time (9 AM to 5 PM Vancouver time)
• Setup: 100% remote
• Compensation: Based on experience. Share your expectations in your application.
• Term: Long-term role

How to Apply

Apply through this posting. Generic applications will be ignored.

Follow these instructions exactly:

1. Start the first line of your application with the word AHEAD in capital letters.
2. Answer the three questions below in order, numbered 1, 2, and 3.
3. After your answers, list the software from the list above that you have used, one per line, with the number of years beside each. If you have used none of them, write “None.”
4. End your application with your salary expectation for a full-time role on these hours, written as a monthly amount in USD.

The three questions:

1. Tell us about the last time you made a decision on your executive’s behalf without asking first. What was it, and how did it turn out?
2. Describe an invoicing or payroll process you ran from start to finish: the system, how many clients or people, and how you caught errors before anything went out.
3. Your executive is travelling for six weeks across three time zones. What changes about how you work?

Applications that skip any of these steps will not be reviewed.

Senior Executive Assistant