Fleet Manager

Fleet Manager

Run the shop. Keep the field moving. Build something better.

At Upscale Lawncare Inc., we do more than install landscapes and hardscapes. We build outdoor spaces we’re proud of, develop leaders from within, and create real career paths for people who want more than just another job.

We’re looking for a Fleet Manager to lead our shop, manage our fleet and equipment, and keep our field teams moving. This role is ideal for someone who takes ownership, thinks ahead, solves problems before they become emergencies, and wants the freedom to improve systems and run the shop the right way.

This is not a sit-back management role. This is a working supervisor position for someone who can lead, organize, communicate, and still jump in when needed.

Why Upscale

At Upscale, this is not a dead-end shop role.

You’ll be part of a growing company with multiple service divisions, strong leadership, and real opportunity to make an impact. We believe in enhancing outdoor environments while growing people, and that shows up in how we hire, train, support, and trust our team.

Why people choose Upscale:

• Opportunity to build structure and improve how the fleet and shop operate
• Direct access to ownership and key operations leaders
• Strong team culture built on accountability, professionalism, service, and excellence
• A company that values safety, organization, communication, and doing things the right way
• Freedom to take initiative and run the shop the way you see best
• Year-round opportunity with a respected brand serving the Cincinnati region

If you want to be trusted, challenged, developed, and part of a company that is building something bigger, Upscale is the place.

Position Summary

The Fleet Manager is responsible for overseeing the shop, coordinating fleet and equipment readiness, managing preventative maintenance and repairs, and making sure trucks, trailers, and equipment are where they need to be to support production.

This role reports directly to the Owner and works closely with the Director of Install, Director of Maintenance, and Project Managers to ensure equipment is available, ready, and supporting the field.

Success in this role means the fleet is organized, downtime is reduced, repairs are handled proactively, the shop runs with accountability, and field teams are supported without constant scrambling.

What Success Looks Like

In this role, you will:

• Keep trucks, trailers, and equipment organized, maintained, and job-ready
• Stay ahead of breakdowns through preventative maintenance and planning
• Ensure equipment is available and allocated properly to support field operations
• Create structure, accountability, and consistency in the shop
• Communicate clearly with leadership, project managers, mechanics, and crew leaders
• Take ownership of problems and solve them before they affect production
• Lead as a working supervisor who sets the tone through action

Essential ResponsibilitiesFleet & Equipment Management

• Oversee maintenance, repair, and readiness of trucks, trailers, and landscape/snow equipment
• Build and manage a preventative maintenance program
• Track service intervals, inspections, registrations, and maintenance records
• Coordinate repairs with internal staff and outside vendors
• Monitor recurring equipment issues and recommend repair or replacement decisions
• Help manage seasonal readiness across multiple divisions

Shop Leadership

• Run the shop with organization, accountability, and clear expectations
• Create systems that improve efficiency, cleanliness, and workflow
• Prioritize work based on operational urgency and field needs
• Maintain inventory of common shop and repair supplies
• Support a culture of safety, pride, and responsibility in the shop

Planning & Communication

• Work closely with the Owner, Director of Install, Director of Maintenance, and Project Managers
• Coordinate equipment availability and timing to support jobs in the field
• Communicate equipment status, repair timelines, and priorities clearly
• Help reduce downtime by planning ahead instead of reacting late
• Identify process improvements and take initiative to implement them

Working Supervisor Expectations

• Be willing to work alongside the team when needed
• Assist with diagnostics, repairs, pickups, deliveries, and equipment movement
• Lead by example through urgency, follow-through, and professionalism

QualificationsExperience

• Experience in fleet management, shop management, equipment management, or a similar operations role
• Strong understanding of trucks, trailers, and landscape/snow equipment
• Experience coordinating repairs, preventative maintenance schedules, and equipment logistics
• Experience with Boss Plows, SaltDogg salt boxes, and Arctic pusher boxes is a plus
• Experience with Bobcat equipment is a plus
• Experience with Ford gas and diesel trucks/equipment is a plus
• Leadership or supervisory experience preferred
• Very Military/Veteran Friendly

Skills

• Strong organization and follow-through
• Ability to think ahead and solve problems proactively
• Strong communication with field leaders and management
• Mechanical awareness and comfort around fleet and equipment operations
• Ability to prioritize multiple moving parts in a fast-paced environment
• Self-starter who does not need constant direction

Requirements

• Valid driver’s license with clean driving record and ability to meet company insurance requirements
• Ability to work outdoors and in shop conditions as needed
• Ability to lift, move, and handle equipment and materials as required
• Ability to work overtime when seasonal demands require it

Core Competencies

• Ownership and initiative
• Forward thinking and planning
• Shop organization and accountability
• Fleet coordination and support
• Communication and teamwork
• Problem-solving and urgency

Compensation & Benefits

• Starting pay based on experience
• General compensation range: $65,000 to $80,000 salary, with bonus opportunities
• Hourly option available based on candidate experience and fit
• 60-day review based on performance and experience
• Take-home truck
• Health, dental, and vision insurance options
• 401(k) with company match
• Paid time off
• Holiday pay on company-designated holidays
• Advancement opportunities as the company continues to grow

Join the Upscale Team

If you’re the kind of person who takes ownership, sees problems before others do, and wants the opportunity to build a better-running shop and fleet operation, we’d love to talk.

At Upscale Lawncare, we’re building more than landscapes. We’re building leaders.

Job Type: Full-time

Benefits:

• 401(k) 3% Match
• Dental insurance
• Employee discount
• Flexible schedule
• Health insurance
• Opportunities for advancement
• Paid time off
• Professional development assistance
• Vision insurance

License/Certification:

• Driver’s License (Required) - Clean, no SR-22's

Ability to Commute:

• Cincinnati, OH 45211 (Required)

Work Location:

• In person

Benefits:

• 401(k)
• 401(k) matching
• Dental insurance
• Employee discount
• Health insurance
• Retirement plan

Work Location: In person