Head Groundskeeper

Job Description

Job Description

If you take pride in healthy soil, thriving plant material, and beautifully maintained outdoor spaces, this is a role where your craft truly shows.

We’re seeking a Head Groundskeeper who sees groundskeeping as more than maintenance—it’s stewardship of a living landscape. This role is responsible for the care and long-term health of all outdoor areas, including gardens, landscaped beds, turf, pathways, event spaces, animal pastures, and brewery grounds. You’ll lead a team while staying hands-on in the work that brings outdoor environments to life through every season.

Why This Role Matters

This isn’t just grounds maintenance—it’s shaping the environment people experience when they visit. Your work directly influences how guests feel when they walk the property: the color, the texture, the seasonal rhythm, and the sense of care in every detail. If you find satisfaction in a clean edge line, a thriving planting bed, or a landscape coming into balance after your work—that mindset will thrive here.

What You’ll Do

Lead & Work Alongside a Skilled Grounds Team

• Set the standard for quality, efficiency, and pride in daily work
• Stay actively involved in field work—not just from the sidelines

Cultivate Beautiful, Healthy Landscapes

• Oversee care of trees, shrubs, annuals, perennials, turf, and natural areas
• Execute and guide mowing, pruning, mulching, planting, weeding, and seasonal rotations
• Maintain the visual appeal and ecological health of the property year-round

Be a Steward of Irrigation & Plant Health

• Monitor irrigation systems to ensure optimal plant hydration and efficiency
• Apply strong horticultural knowledge to promote long-term landscape vitality

Protect and Preserve Through Smart Practices

• Implement integrated pest management (IPM) strategies
• Maintain plant health while minimizing environmental impact
• Apply treatments safely and in compliance with certification requirements

Care for Equipment That Powers the Work

• Oversee maintenance and proper use of grounds equipment and tools
• Ensure your team is trained and confident in safe operation

Shape the Guest Experience

• Partner with landscape designers to bring outdoor vision to life
• Collaborate with event teams to prepare spaces that impress guests year-round

Seasonal Rhythm of the Landscape

• Lead spring awakening and summer growth cycles
• Manage fall cleanup and winter preparation, including snow response if needed
• Ensure every season reflects a well-tended, intentional landscape

Safety & Professional Standards

• Maintain safe, efficient, and organized work environments
• Promote best practices in field safety and equipment use

What We’re Looking For

• 2+ years of supervisory experience in landscaping, groundskeeping, or horticulture
• Strong plant knowledge: trees, shrubs, turf, perennials, and seasonal color
• Experience with irrigation systems and landscape maintenance practices
• Familiarity with equipment such as mowers, trimmers, blowers, and loaders
• A leader who enjoys working outdoors and being part of the crew
• Strong organization, communication, and time management skills
• Ability to work physically demanding outdoor work in all weather conditions
• Ability to lift up to 50 lbs.
• Valid driver’s license required

Licensing & Certifications

• Pesticide Applicator License/Certification required or willingness to obtain

Work Environment

This is a hands-on outdoor role in a dynamic landscape setting. You’ll work across diverse environments—from manicured garden spaces to naturalized areas—experiencing every season firsthand.

Expect:

• Full exposure to changing weather conditions (heat, cold, rain, snow)
• Active physical work including walking large properties daily
• Frequent lifting, bending, and use of professional landscaping equipment
• Occasional ladder work and elevated pruning or maintenance tasks
• Exposure to soil, pollen, dust, and approved plant protection materials (PPE provided)
• Weekend and holiday availability during peak seasons and events
• Collaboration with multiple teams including events, brewery operations, and retail

At Homestead Gardens, we’re more than just a workplace—we’re an award-winning, community-centered team with deep roots in Anne Arundel County, MD, where we’ve been voted the “Best Of” for 49 years and counting. As the #1 family-owned retailer in the area, we take pride in supporting our local community, having donated over $1 million to local causes. When you join us, you’ll enjoy competitive pay, flexible hours, and a wealth of professional development opportunities, all while working alongside a passionate team that shares your love for plants and the great outdoors. Be part of something vibrant and impactful—join the Homestead Gardens family today!

Company Description

At Homestead Gardens, we’re more than just a workplace—we’re an award-winning, community-centered team with deep roots in Anne Arundel County, MD, where we’ve been voted the “Best Of” for 49 years and counting. As the #1 family-owned retailer in the area, we take pride in supporting our local community, having donated over $1 million to local causes. When you join us, you’ll enjoy competitive pay, flexible hours, and a wealth of professional development opportunities, all while working alongside a passionate team that shares your love for plants and the great outdoors. Be part of something vibrant and impactful—join the Homestead Gardens family today!