Landscaping Careers at Oakly landscaping

Join a company that builds people just as much as it builds landscapes. At Oakly Landscaping, we’re not just hiring — we’re investing in individuals who want to grow, lead, and take pride in their work. Whether you’re new to the industry or a seasoned pro, we have a place for you. Our job sites span across Oakville, Mississauga, Burlington, Milton, and Hamilton, offering full-time, seasonal, and leadership opportunities. If you’re ready to be part of a team that values your effort, supports your growth, and celebrates wins together, your next career move starts here.

📍 Currently looking for Maintenance Crew Leader, Maintenance Technician, Landscaping Crew Leader, Landscaping Technician

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Landscaping Careers | Oakly Landscaping

At Oakly Landscaping, we take pride in transforming outdoor spaces into stunning, functional landscapes that enhance the beauty and value of our clients’ properties. With over eight years of experience, we have grown into a trusted name in Mississauga, serving residential and commercial properties with unmatched professionalism and attention to detail. Our team is built on a foundation of innovation, collaboration, and a commitment to delivering excellence. We believe in empowering our employees, fostering growth, and creating a culture where everyone can thrive.

Open positions

Maintenance Crew Leader

About The Role

The Maintenance Crew Leader ensures properties consistently reflect Oakly’s standards of excellence. You’ll oversee routine maintenance tasks, lead your crew, and maintain clear communication with clients.

Compensation

Leader: $25–$27/hr

Key Responsibilities

Supervise crew members during job execution.
Submit daily updates regarding job progress, hours worked, and any issues (photos, expenses, log times).
Ensure safe and efficient use of tools and equipment.
Maintain high-quality standards on all projects.
Communicate immediate needs or issues to the Operations Manager.
Enforce company uniform standards.
Ensure crew compliance with shift clock-in/out procedures.
Report crew performance concerns to management.

Qualifications

Extensive experience in landscape maintenance.
Valid Full G driver’s license required.
Strong leadership and clear communication skills.
Proficiency in maintenance equipment operation.

Apply Today

Ready to grow your career with Oakly Landscaping? Apply now by sending your resume and cover letter to contact@oaklylandscaping.com. We can’t wait to welcome you to our team and build a remarkable future together.

Maintenance Technician

About The Role

The Maintenance Technician performs routine landscape maintenance tasks to maintain the visual and functional standards of client properties.

Compensation

Technician: $18–$20/hr

Key Responsibilities

Execute lawn care, trimming, edging, and general maintenance.
Assist crew leader in daily tasks and job completion.
Adhere strictly to safety standards and equipment handling.

Qualifications

Entry-level role; prior experience is beneficial but not required.
Strong work ethic and willingness to learn.

Apply Today

Landscaping Crew Leader

About The Role

The Landscaping Crew Leader oversees landscape projects, ensuring beautiful, functional outdoor spaces. You’ll lead your team in design implementation and maintain project standards.

Compensation

Leader: $25–$27/hr

Key Responsibilities

Supervise crew members during landscaping projects.
Submit daily progress updates including hours, job status, and relevant issues.
Ensure safe equipment use and maintenance.
Uphold project quality standards.
Communicate directly with the Operations Manager about immediate needs.
Ensure compliance with uniform standards and company regulations for shifts.
Report team performance concerns promptly.

Qualifications

Significant landscaping experience.
Valid Full G driver’s license required.
Knowledge of landscaping techniques and plant care.
Effective leadership and communication abilities.

Apply Today

Landscaping Technician

About The Role

The Landscaping Technician assists in executing landscaping projects to create appealing and functional outdoor environments.

Compensation

Technician: $18–$20/hr

Key Responsibilities

Support in project execution including planting, mulching, and installations.
Maintain cleanliness and organization of job sites.
Ensure safe handling of tools and materials.

Qualifications

Entry-level role; landscaping experience beneficial.
Team-oriented with a strong willingness to learn.

Apply Today

Why Choose oakly landscaping?

Joining Oakly Landscaping isn’t just about getting a job — it’s about becoming part of something bigger. We’ve built our company on the belief that great work starts with great people. That means we’re not just looking for labour — we’re investing in team members who want to grow, take pride in what they do, and be part of a crew that truly supports one another.

When you join Oakly, you’re stepping into a workplace where your voice is heard, your effort is noticed, and your future matters. We offer structured career paths, hands-on training, and leadership that cares about your personal and professional development. Whether you’re just starting out or bringing years of experience, there’s a place for you here — and plenty of room to grow.

Our projects are meaningful, our standards are high, and our culture is real. We work hard, we celebrate wins, and we push each other to be better every day. If you’re looking for a career where you can build more than just landscapes — where you can build a future — Oakly is the place to do it.

Areas we are hiring from

Clear Career:
Progression

From entry-level technician to Operations Manager, we offer structured career paths that provide clear, attainable advancement steps. Our commitment is to help every team member grow professionally & personally.

Culture of Recognition
and Support

Regular recognition, employee-of-the-month awards, and ongoing training ensure you feel valued and prepared for your role. We foster a collaborative environment where your voice matters.

Work-Life
Balance

We understand that your life extends beyond work. Oakly ensures balanced working hours, structured time-off policies, and ongoing support for personal and financial well-being.