City of Toronto jobs

I’m a busy professional with a demanding schedule and high standards, and I need someone to take over the personal side of my life. I’ll tell you what I need done, what matters to me, and what the budget is. From there it’s yours. I’m looking for someone who figures out the best way to get it done, finds the right people, follows through, and lets me know when it’s finished.

What you’ll handle

• Admin and household tasks: booking services, arranging repairs, furnishing, appointments, and errands
• Keeping my documents, records, and paperwork organized and up to date
• Financial admin: mortgage paperwork, bank and insurance matters, and coordinating with my accountant and other advisors
• Updating my wardrobe, from shopping and tailoring to organizing what I already have
• Helping family with practical matters, from finding the right professionals to sorting out problems that have stalled
• Supporting a family-run small business, including hiring, letting people go when needed, and managing vendors
• Handling problems as they come up, whether it’s a tech issue, a contractor who didn’t show, or a bureaucratic mess
• Planning travel, dinners, and events
• Researching decisions and coming back with a clear recommendation
• Occasional remote admin backup for a medical practice (scheduling, phones, billing follow-up), with training provided

What I’m looking for

• Someone who finishes what they start. When you say it’s done, it’s done, and I don’t need to follow up.
• Strong judgment. You know when to handle something yourself, when to bring in an expert, and when to check with me.
• Good with people. You’re comfortable dealing with family members, tradespeople, and professionals, and you pick up quickly on how I like things done.
• Direct communication. I’m blunt and I want the same back. If you think something is a bad idea or will cost more than expected, tell me early.
• Complete discretion. You’ll be dealing with personal, family, and financial matters.
• Organized, with short, clear updates.

Requirements

• 5+ years in an executive assistant, chief of staff, operations, concierge, or similar role with real independence
• Comfortable using modern AI tools to work faster, with good judgment about when to double-check their output
• Based in Toronto/GTA, with a valid Ontario G license, a clean driving record, and a reliable vehicle insured for business use (mileage reimbursed)
• Available 15–20 hours per week, reachable during business hours, with some flexibility for urgent matters
• Excellent written and spoken English (French or Farsi is a plus)
• Experience with medical office software or billing is an asset, not a requirement
• Willing to sign a confidentiality and non-disclosure agreement

What I offer

• Minimum weekly pay of $750–1,050/week (15 hours at $50–70/hour, depending on experience), with additional pre-approved hours at the same rate
• A raise of $5-10/hour after a successful 90-day probation
• Real autonomy and a budget to work with
• Straight feedback and respect for your judgment

How to apply

Send your resume and a short note (under 400 words) answering these questions:

• Tell me about a time you were handed a messy problem with no instructions. What did you do, and how did it turn out?
• A family business needs to replace a key employee. You have a budget and full responsibility. What are your first five steps?
• What parts of that job would you use AI tools for, and what wouldn’t you trust them with?

Finalists will be paid to complete a short trial task. Any offer will depend on reference checks, a criminal record check, a credit check, and a driver’s abstract, all done with your written consent.

Pay: $50.00-$75.00 per hour

Expected hours: 15.0 – 25.0 per week

Benefits:

• Flexible schedule
• Mileage reimbursement
• Work from home

Work Location: Hybrid remote in Toronto, ON (Toronto District)