Landscaping Supervisor - Full- Time

Cypress-Living; Fort Myers (FL); On-site; USD 55,000 - 85,000; Full time

Job summary

CRG Property Management, serving Cypress Cove and other Cypress organizations, seeks a Landscaping Supervisor in Fort Myers, FL. You will lead grounds teams, coordinate internal resources and external vendors, and ensure safe, beautiful outdoor spaces across campus.

The role requires strong horticultural knowledge, organizational skills, and the ability to manage priorities in a large, hospitality-like campus setting.

Qualifications

• 5+ years in landscaping, grounds management, horticulture, or related field.

Responsibilities

• Lead landscaping, grounds maintenance, and campus enhancement programs.
• Develop seasonal landscaping plans including irrigation strategies for Southwest Florida.

Skills

Leadership

Budget management

Vendor management

Job description

Cypress Living Main Office
Fort Myers, FL 33908, USA

• On-site
• Administration
• Full-Time
• Requisition #: LANDS001145

Description

CRG Property Management is seeking an experienced and motivated Landscaping Supervisor to lead our grounds maintenance, landscaping, and campus beautification operations.

This is an exciting opportunity for a hands‑on leader who combines strong horticultural knowledge with excellent organization, leadership, and decision‑making skills. The Landscaping Supervisor will play a key role in maintaining beautiful, safe, and welcoming environments while leading a talented grounds team and coordinating internal resources and external vendors.

WHAT YOU WILL BE DOING:

• Lead the planning and execution of landscaping, grounds maintenance, and campus enhancement programs.
• Develop seasonal landscaping plans, including plantings, irrigation strategies, and sustainability initiatives suited to Southwest Florida conditions.
• Establish daily and long‑term priorities based on operational needs, seasonal demands, weather, staffing, and available resources.
• Oversee lawns, walkways, lakes, water features, irrigation systems, landscaped areas, and other exterior spaces.
• Maintain campus curb appeal in accordance with established standards and client expectations.
• Develop a preventative maintenance plan to ensure landscaping equipment is safe and operating efficiently.
• Identify and resolve issues involving irrigation, drainage, plant health, pest management, and storm‑related damage.
• Coordinate storm preparation, campus readiness, post‑storm cleanup, and restoration efforts.
• Ensure compliance with environmental standards, water‑use guidelines, and safe application of landscaping materials.
• Provide recommendations to leadership regarding grounds improvements, beautification projects, and long‑term sustainability.
• Coordinate and oversee internal grounds staff and external landscaping vendors.
• Evaluate vendor performance, including scope, pricing, quality, and service delivery.
• Develop and manage landscaping budgets covering materials, labor, and contracted services.
• Monitor expenses and identify opportunities to improve efficiency and control costs.
• May oversee landscaping services for property owners’ associations (POAs) and other contracted clients, ensuring consistent quality and effective use of resources.
• Provide day‑to‑day leadership, direction, and support to grounds and landscaping team members.
• Participate in interviewing, selection, hiring, and onboarding decisions.
• Provide meaningful input regarding hiring, discipline, and termination decisions.
• Conduct performance evaluations and provide ongoing coaching, feedback, and professional development.
• Address performance concerns and administer corrective action in accordance with company policies.
• Review and approve employee timecards and time‑off requests while ensuring appropriate staffing coverage.
• Foster a safe, productive, collaborative, and team‑oriented work environment.

WHAT WE ARE LOOKING FOR:

• Minimum 5 years of experience in landscaping, grounds management, horticulture, or a related field
• Must possess a current Green Industries Best Management Practices (GI-BMP) Certification and Florida Limited Commercial Landscape Maintenance (LCLM) license, or have the ability to obtain both within six (6) months of hire
• Strong ability to lead teams and manage day‑to‑day operations
• Experience managing budgets and vendor relationships
• Understanding of irrigation systems, drainage, and Southwest Florida environmental conditions
• Ability to manage multiple seasonal and operational priorities
• Excellent problem‑solving and independent decision‑making skills
• Strong communication, organization, and follow‑through
• Experience in a large campus, hospitality, country club, golf course, senior living, or similar environment

We are:

• CRG Property Management supports a broad range of property management, facilities, landscaping, grounds, and campus operations for Cypress Cove and other affiliated Cypress organizations, as well as property owners’ associations and other contracted clients. As part of the Cypress family, which includes Cypress Living, Cypress Cove, Cypress at Home, and CRG Advisory Services, we work together to create vibrant communities, maintain exceptional environments, and support the mission of enhancing abundant living for aging adults.

Join CRG Property Management and help us cultivate exceptional environments, strong teams, and lasting results.

Qualifications

Experience

Required

5 years: Landscaping, grounds management, horticulture, or a related field.

Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws.For further information, please review the Know Your Rights notice from the Department of Labor.