Landscape Supervisor

Landscaping Supervisor (Hands-On Crew Lead, 3-4 Person Crew) Company: Neighbourhood Landscaping Location: Toronto, ON (jEtobicoke) Reports to: Operations Manager Position type: Seasonal The Role We’re hiring an experienced Landscaping Supervisor to lead a 3 or 4-person crew in the field. This is a hands-on role, where you’ll be working alongside a crew of landscapers to deliver our landscaping services. As the supervisor, you will be responsible for supervising the crew, setting the pace, protecting quality, and keeping on schedule. You’ll also be the on-site point of contact for customers and ensure accurate time tracking using Jobber. What You’ll Be Responsible For: Crew leadership and daily execution Lead a crew on daily maintenance and property enhancement work Assign tasks, coach crew members, and maintain a positive, accountable jobsite culture Run quick daily start-of-day expectations and safety check-ins Equipment, tools, and load-out Confirm trucks, trailers, tools, and PPE are properly loaded and secured for the day Perform basic daily equipment checks (fuel, obvious issues, safe operation) Flag equipment/tool issues promptly for repair or replacement Schedule and production Execute the daily job schedule efficiently and adjust pacing as needed Communicate job progress, issues, and weather impacts to the Operations Manager Keep sites moving while protecting quality and safety Time tracking and job tracking (Jobber) Ensure crew members are clocking in and out of jobs accurately in Jobber Add clear job notes and photos to document work completed and any issues Quality control Perform on-site quality checks before leaving each property Correct deficiencies the same day when possible Maintain clean, professional jobsites and a strong customer experience Customer communication Act as the on-site point of contact for customers during service Handle questions and minor concerns professionally Escalate issues, scope changes, or upsell opportunities to the Operations Manager What We’re Looking For: 3+ years in landscaping with at least 1 year leading a crew (or equivalent responsibility) Strong working knowledge of maintenance services (mowing, edging, pruning, bed care, cleanups, mulching) Confident running equipment safely (mowers, trimmers, blowers, edgers, etc.) Comfortable using mobile apps for job tracking and timekeeping (Jobber experience is a strong asset) Reliable communicator, calm under pressure, and good with customers on site Valid driver’s license with a clean driving record (ability to drive truck and trailer is an asset) Physically able to work outdoors and lift up to 50 lbs What Success Looks Like (First 60 to 90 Days): Runs morning load-out smoothly and consistently Crew is on time, on schedule, and producing quality work daily Time tracking in Jobber is accurate and complete with clear notes Minimal call-backs, strong site quality, and positive customer interactions Compensation and Perks : Competitive pay based on experience Opportunities for growth into larger crew leadership or field management roles Training and support from an Operations Manager and Company leadership How to Apply: Send your resume to rob@outsiderholdings.ca with the subject line: Landscaping Supervisor Application. Include: Your years of experience and crew leadership background Whether you have Jobber experience Whether you can tow/drive truck + trailer