Description:
Lifestyle Personal Assistant
The Opportunity: This is a perfect high-leverage role for someone looking for a rewarding way to generate extra income while engaging in the world of high-end lifestyle management.
About Injoy Injoy is the human-led "secret weapon" for the next generation of visionary founders. We don’t just "help". We integrate directly into our clients' lives to remove the friction of the day-to-day so they can focus on what truly matters. Our philosophy is built on Human-First intuition that software simply cannot replicate. We invest deeply in learning your "why" and "how," handling the noise so you can fuel the vision and make your time truly yours again.
The Role We are looking for a Lifestyle Personal Assistant who thrives on turning complex constraints into elegant, high-end realities. This is a remote-first role that requires occasional travel around Toronto for local errands and support. You aren't just an assistant, you're a proactive executor and a discreet partner who senses unspoken preferences before they are even uttered. From sourcing "impossible" Michelin reservations to navigating real-time travel crises across Asia, you bring a sense of magic and effortlessness to every moment.
The Lifestyle Fit (Why You’ll Love This)
This role is designed for someone who finds genuine joy in the details of a life well-lived.
- A Creative Outlet: You are encouraged to use your "human intuition" to curate moments that feel like art—whether it’s a perfectly timed update or a thoughtfully selected backup plan.
- A World of Discovery: If you are energized by the beauty of high-end Asia travel, the serenity of a private onsen, or the precision of kaiseki, you will find this work deeply inspiring.
- Quiet Impact: You take pride in being the "calm in the storm," knowing that your creative problem-solving creates a world of ease for someone else.
What You'll Do
- Curate Luxury Experiences: Research and book high-end travel, including kaiseki, onsen, and exclusive hotels with a heavy focus on Asia expertise.
- Flight & Logistics Strategy: Expertly source premium business-class flights (Toronto → Asia) using award space and upgrades.
- Real-Time Support: Provide time-zone flexible support for shifting priorities, from deep research to last-minute reservation wins.
- Financial Stewardship: Manage trip budgets (typically $30k–$80k) to deliver indulgent outcomes under target.
- Local Operations: Execute errands and logistics within the Toronto area to ensure the client’s home base runs as smoothly as his travel.
Who You Are
- A Sophisticated Navigator: 2+ years of experience supporting HNW individuals with absolute discretion.
- A Travel Expert: Passionate about high-end travel, from private onsens to Michelin dining.
- A Thoughtful Communicator: You provide clear, timely, and reassuring updates so nothing is ever left to chance
- A True Partner: You value mutual appreciation and take pride in being a quietly supportive force.
- A Calm Executor: You thrive on ambiguity and turn constraints into elegant solutions.
What Success Looks Like
- Proactive Problem-Solving: You anticipate needs before they arise, like securing a quiet booth away from kitchen noise, and sense unspoken preferences to personalize every moment
- Thoughtful Execution: You transform high-pressure disruptions, like missed flights, into seamless, elegant solutions.
- Global Logistics Mastery: You successfully lead 4–8 week multi-country itineraries with a focus on a seamless experience.
- Transparency: You are a "thoughtful over-communicator," providing proactive and reassuring updates.
- Compound Impact: You handle the "noise" so the founder can stay in their zone of genius.