They Manage Empires. You Manage Everything Else.

💰 $20–$27/hr (USD) 🕐 Contract / Temp 📍 Remote (Toronto errands required) 🏢 Injoy – Private Advertiser

Imagine being handed a $50,000 travel budget and told: “Make it perfect.” Private onsens in Kyoto. A kaiseki dinner booked three months out. A last-minute flight reroute across three time zones — handled before your client even asks.

This isn’t a typical assistant role. This is an invitation to become the invisible engine behind a visionary founder’s world.

Who Is Injoy?

Injoy isn’t a staffing agency — it’s a philosophy. Built for the next generation of high-performance founders, Injoy integrates directly into a client’s life rather than sitting on the sidelines. The belief is simple: human intuition cannot be automated. No app can sense when your client wants quiet. No algorithm can curate a moment that feels like magic.

That’s where you come in.

What Makes This Role Different

✈️ Real luxury travel: You’re not booking budget hotels. You’re sourcing impossible Michelin reservations, navigating award flight upgrades on business class routes from Toronto to Asia, and managing multi-country itineraries spanning 4–8 weeks.

🧠 Proactive, not reactive: You anticipate needs before they’re spoken — like knowing your client prefers a corner booth away from kitchen noise without being told.

🌿 Creative freedom: You’re encouraged to bring your own human touch. A perfectly timed update. A backup plan that’s somehow better than the original. This is execution as art.

What You’ll Actually Do

Curate luxury travel experiences — high-end Asia itineraries, private onsens, kaiseki dining, and exclusive hotels
Master flight logistics — sourcing premium business-class flights using award space and upgrades (Toronto → Asia routes)
Provide real-time support across time zones — calm, fast, and always one step ahead
Manage serious budgets — typically $30,000–$80,000 per trip, maximising every dollar for indulgent outcomes
Handle local Toronto operations — errands and logistics so the home base runs as smoothly as the travel

You’ll Thrive Here If You Are…

🎯 Experienced — 2+ years supporting high-net-worth individuals with full discretion
🌏 Asia-travel savvy — you don’t just know the destinations, you feel them
🗣️ A calm, clear communicator — a “thoughtful over-communicator” who leaves zero to chance
🔍 Detail-obsessed — you catch problems three steps before they happen
🤝 A true partner — not an order-taker, but a quietly powerful force behind the scenes

💵 $20–$27/hr USD | Remote-First | Contract Role

The Hiring Process — No Games, No Ghosting

15-Minute Intro Call — Quick alignment check. Is this a fit? You’ll know fast.
Practical Task Project — A short, real-world exercise done on your own time. Show your logistics thinking and creative execution.
30-Minute Final Interview — A direct conversation with the client. No panel. No tricks.

What Success Looks Like After 90 Days

You’ve led at least one full multi-country Asia itinerary from start to finish. Every disruption — delayed flight, fully-booked restaurant, last-minute schedule shift — was handled so seamlessly the client barely noticed. You’ve become the person they trust without thinking twice. The invisible pillar. The quiet genius.

If that sounds like exactly the kind of role you were built for — this is your moment.

Ready to Manage the Extraordinary?

This role fills fast. Visionary founders don’t wait — and neither should you.
Send your resume + a short note on why you’re the one for this.

✦ Apply Now

Include your expected monthly salary, PA experience, and why high-end travel excites you.