Lawn Maintenance Manager

Lawn Maintenance Manager

📍 Amaranth / Orangeville, ON
🕒 Full-Time | Year-Round

Whispering Pines Landscaping is seeking a Lawn Maintenance Manager to lead our Lawn Division during the green season and provide structured leadership, planning, and operational oversight year-round.

This is a hands-on leadership role focused on people, planning, accountability, and execution. You will play a critical role in ensuring crews are organized, supported, productive, and aligned with company standards.

You will work closely with Operations, HR, and the Management Team to ensure the division runs efficiently and profitably.

What You’ll Do

🌿 Lawn Maintenance Leadership

• Lead and oversee all lawn maintenance crews
  • Ensure crews are prepared, dispatched on time, and working safely
  • Monitor job progress, labour efficiency, and quality standards
  • Manage attendance, time tracking, and daily labour planning
  • Conduct site visits and quality control inspections
  • Communicate budgeted hours and performance expectations
  • Coordinate equipment, materials, and maintenance needs
  • Develop action plans to address quality or performance gaps
  • Participate in financial reviews and help drive divisional profitability
  • Support route optimization and efficiency planning
  • Ensure compliance with company safety standards and procedures

People Leadership

• Lead with a servant-leadership mindset. Your crews know you have their back
  • Set clear expectations and hold teams accountable
  • Support hiring, onboarding, training, and performance development
  • Partner with HR and Operations on employee relations and discipline
  • Build a strong, positive team culture
  • Model and promote Whispering Pines’ core values:
  Respect • Integrity • Teamwork • Excellence • Leadership

Who This Role Is For

• Highly organized, structured leaders
  • Confident people managers who enjoy leading crews in the field
  • Calm decision-makers who thrive under pressure
  • Individuals who take pride in operational excellence
  • Leaders comfortable balancing hands-on supervision with planning and reporting
  • Those who value accountability, systems, and continuous improvement

Experience & Skills

• 3–7+ years of experience in landscaping or maintenance operations
  • Proven supervisory or leadership experience
  • Strong scheduling, planning, and organizational skills
  • Ability to manage multiple crews and shifting priorities
  • Experience tracking labour, job performance, and budgets
  • Comfortable using operational software and reporting tools
  • Valid driver’s license required

Why Join Whispering Pines Landscaping

• Salary range: $80,000- $100,000 annually, depending on experience
  • Comprehensive group benefits
  • Retirement Savings Plan
  • Employee Assistance Program
  • Annual profit-sharing opportunities
  • Career growth and leadership development
  • Monthly team-building events and company gatherings
  • Supportive management team with strong systems
  • Be part of a respected, growing organization with long-term vision

Ready to Lead the Way?

📩 Apply today and grow your leadership career with Whispering Pines Landscaping.

We’re Proud to Be an Equal Opportunity Employer

Whispering Pines Landscaping is committed to building an inclusive, respectful, and diverse workplace. We welcome and encourage applications from people of all backgrounds and experiences.