Fleet Operations Manager

About the Role

Winston Water Cooler is seeking a seasoned and strategic Fleet Operations Manager to take full ownership of our growing fleet across 70 locations. This is a hands-on, high-impact role where you'll lead the charge in developing a modern, scalable fleet program from compliance and budgeting to systems implementation and vendor partnerships.

You’ll work closely with our VP of Operations and branch leadership to ensure our vehicles, ranging from light-duty pickups to commercial trucks and trailers, are always road-ready, compliant, cost-effective, and aligned with business needs.

Key Responsibilities

• Lead the overall fleet strategy, operations, and compliance for 70 branches.
• Ensure all vehicles meet federal and state DOT requirements, including CDL-related standards.
• Manage all fleet documentation: registrations, renewals, insurance claims, audits, and compliance records.
• Own the fleet budget, including fuel programs, maintenance, leasing, and vendor relationships.
• Evaluate, select, and implement a fleet management software solution to streamline operations and improve visibility.
• Collaborate with branch managers to ensure adherence to vehicle standards and policies across all locations.
• Track and report on costs, usage, and compliance metrics for executive leadership.
• Stay current on regulatory changes and proactively adjust programs to ensure uninterrupted compliance and safety.

Qualifications

• 5 years of experience managing mixed-use fleets (light-duty, heavy-duty, trailers, and commercial vehicles).
• Expertise in DOT compliance and CDL-related requirements (CDL not required).
• Strong budget management skills and experience negotiating with fleet vendors and service providers.
• Proven ability to research and implement new systems or tools (experience with fleet management software preferred).
• Excellent organizational, communication, and multi-location coordination skills.
• Proficiency with Microsoft Office Suite, particularly Excel, Word, and Outlook.
• Fleet-related certifications (e.g., NAFA CAFM or equivalent) are a plus, but not required.

What Sets This Role Apart

• High Visibility: Report directly to the VP of Operations and collaborate with leadership across the business.
• Real Impact: Build and shape a fleet program that drives efficiency, safety, and scalability.
• Growth Opportunity: Be part of a growing company with room to evolve into broader operations leadership.
• Competitive Package: $80,000–$95,000/year DOE, plus benefits.

If you're ready to bring strategy and structure to a complex, multi-location fleet and want to be part of a company that values operational excellence, we’d love to hear from you.