Challenger 300 Captain (YYZ) – Toronto/Mississauga

"

✈️ Challenger 300 Captain – Take the Left Seat in Toronto (YYZ)

Chartright Air Group is seeking a seasoned Challenger 300 Captain to be based in Mississauga and operate from Toronto (YYZ). In this client-facing, safety-first role, you’ll lead private jet charter missions, collaborate across Flight Coordination and Sales, and help shape continuous improvement across the organization.

  • Location: Mississauga, Ontario (operating out of Toronto/YYZ)
  • Company: Chartright Air Group
  • Aircraft: Bombardier Challenger 300
  • Minimum total time: 5,000 hours
  • PIC multi‑engine: 1,000+ hours required
  • Licences: Canadian ATPL, Group 1 Multi‑Engine IFR, Canadian Radio Telephone Licence
  • Medical: Valid Transport Canada Medical

🧭 What you’ll do

  • Act as Captain on the Challenger 300, ensuring every flight is conducted with uncompromising safety and professionalism.
  • Coordinate closely with the Flight Coordination Centre and Sales to deliver seamless operations and an exceptional client experience.
  • Provide direct, high‑touch customer service throughout each mission.
  • Support daily operational activities on available reserve days to keep the operation running smoothly.
  • Complete monthly training and remain current on procedures, aircraft systems, and safety standards.
  • Foster a collaborative culture by sharing ideas, improvements, and solutions with teammates across the organization.
  • Perform additional duties as required to support safe, efficient charter operations.

🧰 What you bring

  • Canadian ATPL, Group 1 Multi‑Engine IFR, valid Transport Canada Medical, and Canadian Radio Telephone Licence.
  • Minimum 5,000 hours total flight time and 1,000+ hours as Pilot‑in‑Command on multi‑engine aircraft (turbine time preferred).
  • Proficiency with FMS and glass cockpit avionics; able to interpret and manage complex flight data.
  • Strong knowledge of aviation weather, airport performance, flight planning and calculations, fuel planning, weight and balance, Canadian Aviation Regulations, and SMS practices.
  • Excellent written and verbal communication; client‑centric mindset with polished service skills.
  • Organized, detail‑driven, and able to prioritize effectively in a dynamic environment.
  • Team‑oriented, collaborative approach with the flexibility to support evolving client needs.
  • Ability to lift up to 60 lb.

🌟 Why you’ll love flying with Chartright

  • Opportunities to influence company growth and transformation alongside talented professionals.
  • Commitment to personal and professional development, including ongoing training.
  • 100% company‑paid extended health and dental coverage.
  • Employee discounts through valued partnerships for you and your family.
  • Generous RRSP/DPSP matching program.

📨 Ready to apply?

If you’re a safety‑focused leader who thrives in a collaborative, client‑centric environment, we’d love to hear from you. Step into the left seat on the Challenger 300 and help deliver an exceptional charter experience with Chartright Air Group.

"

Back to blog

Other Jobs To Apply

No other job posts for this day.

Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...