Landscape Maintenance Estimator

Grow + Lead Salisbury's Maintenance Division

Why This Role? Why Now?

Salisbury Landscaping is expanding our year-round Landscape Maintenance Division, and we're looking for someone who knows the field, understands the work, and is ready for the next step.

If you've spent years in landscape maintenance—running crews, managing sites, solving problems on the fly—and you're ready to transition into an office-based leadership role where your field experience becomes your superpower, this is the opportunity.

You'll shape systems, win new work, influence hiring and training, and help build a division with huge growth potential.

This isn't just estimating.

This is taking ownership of a division and growing it.

Who you are

A Maintenance Pro Ready for a New Challenge

You've spent time in the field and know what maintenance really takes—labour pacing, equipment needs, seasonal challenges, and client expectations.

Operationally Smart

You understand how to build efficient routes, structure crews, price accurately, and spot where productivity is lost—or gained.

Driven to Build Something Bigger

You're motivated by growth: more clients, more contracts, stronger systems, and high-performing crews.

A Confident Communicator

Whether you're walking a site, presenting a proposal, or guiding a foreman, you bring clarity, confidence, and a collaborative approach.

Ready to Lead

You want a role where your experience influences decisions, shapes processes, and drives results.

What You'll Do

Estimation & Sales (Core Focus)

• Price and estimate residential and commercial maintenance contracts using your field knowledge to ensure accuracy.
• Build maintenance packages that balance client expectations with operational efficiency.
• Prepare proposals, present to clients, and win work that supports sustainable growth.
• Conduct site visits, scope assessments, and seasonal reviews with clients.

Division Growth & Leadership

• Help shape the structure and systems of our expanding Maintenance Division.
• Identify gaps and propose improvements in routing, scheduling, productivity, and client experience.
• Support recruitment, onboarding, and training of maintenance staff.
• Work closely with Operations to align estimates with real-time production.

Field Coordination & Quality Assurance

• Partner with foremen and lead hands to ensure crews are set up for success.
• Conduct periodic site walks to validate quality, production pacing, and safety.
• Ensure materials, equipment, and information are fully prepared ahead of scheduled work.

Financial & Operational Oversight

• Track job costs vs. estimates and recommend efficiencies.
• Review crew productivity and provide input on labour planning.
• Maintain accurate records in Aspire (or similar systems).

Qualifications

• 3–5+ years of experience in landscape maintenance (crew lead, foreman, supervisor, or similar).
• Strong understanding of residential and/or commercial maintenance operations.
• Experience estimating, job costing, or quoting maintenance work (formal or informal).
• Strong communication and relationship-building skills.
• Highly organized; able to manage multiple bids and timelines.
• Proficiency in Aspire or similar systems (an asset).
• Valid Class 5 license with a clean abstract.

If you've been looking for a way off the tools without losing connection to the work you know, this role is the bridge.

Benefits

• Year-round employment
• Group Benefits and Health Spending Account after three (3) months
• Wellness Program
• Employer Family Assistance Plan (EFAP) with 24/7 short-term counselling and wellness services. There is no cost to employees with access by phone or web
• Employee RRSP matching up to $1000 after one year of employment
• Courses and Onsite Training
• COR Certified
• Safety Training

Job Type: Full-time

Pay: $70,000.00 per year

Benefits:

• Company events
• Dental care
• Disability insurance
• Employee assistance program
• Extended health care
• Life insurance
• On-site parking
• RRSP match

Work Location: In person