Oakly Landscaping is hiring a Maintenance Crew Leader to lead a 2–4 person maintenance crew serving residential and commercial properties across the GTA.

This role is for someone who can lead from the front, keep the day organized, maintain high standards, and make sure the crew is ready to work before leaving the yard.

The work

You will be responsible for:

- Organizing the crew and confirming the day's route, priorities, access notes, and property instructions
- Leading mowing, edging, trimming, blowing, pruning, detail work, and seasonal cleanups
- Completing start-of-day circle checks on the truck, trailer, tools, and equipment
- Assigning tasks and keeping the crew productive and on pace
- Inspecting completed work and correcting quality issues
- Training and supporting crew members
- Communicating professionally with clients, property managers, and the office
- Reporting completed work, delays, material needs, safety concerns, and equipment issues
- Keeping trucks, trailers, tools, and equipment clean, organized, secure, and ready
- Participating in weekly crew-lead planning meetings

What success looks like

- The crew is prepared and past the gate by the 7:00 AM departure target.
- Routes stay organized and work is completed on pace.
- Properties meet Oakly's quality standard with minimal callbacks and rework.
- Crew members receive clear direction, training, and feedback.
- Daily reports and field updates are accurate and timely.
- Equipment is inspected, cared for, secured, and ready for the next shift.
- Clients and property managers experience a professional, reliable crew.

What we're looking for

- Experience leading a landscaping or property maintenance crew
- Strong experience with mowing, pruning, trimming, edging, blowing, detail work, and seasonal cleanups
- Ability to organize people, tools, equipment, and route priorities
- Strong communication skills with clients and property managers
- High standards for quality,



safety, cleanliness, and accountability
- Ability to train and coach less-experienced team members
- Physical ability to perform landscape maintenance and lift materials
- Comfort working outdoors in changing weather
- Full G driver's licence with a clean abstract
- CVOR eligibility and willingness to apply
- Fluent English communication skills; Spanish is a strong asset

Why join Oakly Landscaping Oakly Landscaping is a full-service residential and commercial landscaping company based in Mississauga and serving the GTA.

We focus on reliable execution, quality craftsmanship, clear communication, safety, and professional service. Our maintenance crews use clear readiness and closeout standards so the day starts organized and problems are reported before they affect production or the client experience.

This is an opportunity to take real ownership of a crew, develop junior team members, and grow with a company that values professionalism, integrity, accountability, and lasting results.

What we provide

- CA$25.00–CA$27.00 per hour
- Full time, in-person work
- On-site parking
- Opportunity to grow into greater field responsibility
- Support from office and operations leadership
- Clear standards and accountability

This isn't for you if…

- You are not comfortable being responsible for the crew's preparation, conduct, and results.
- You regularly arrive late or leave readiness and cleanup problems for someone else.
- You avoid feedback or accountability.
- You are careless with company vehicles, equipment, tools, or client properties.
- You want the title without the responsibility of leading people and protecting quality.

How to apply Send your resume and a short note about your landscaping leadership experience to [email protected].

Please include your availability, driver's licence status, and a brief description of the maintenance crews or routes you have led.

Pay: $25.00-$27.00 per hour

Work Location: In person

📌 Maintenance Crew Leader (Oakville)
🏢 Oakly Landscaping
📍 Oakville