8+ years in fleet, transportation, or maintenance management with leadership experience
Experience managing a large, dispersed commercial fleet (500+ assets preferred)
Strong knowledge of DOT/FMCSA regulations and commercial vehicle inspection
Hands-on experience with Fleetio or similar fleet management systems
Proficient in data analysis, budgeting, and lifecycle planning
Excellent communication and leadership skills
Bachelor's or Master's degree in a related field or equivalent experience
Valid driver's license and willingness to travel regularly
Responsibilities
Set fleet strategy and maintenance standards across all locations
Lead DOT/FMCSA compliance and oversee vehicle registrations
Improve fleet uptime and reliability, tracking inspections and repairs
Manage vehicle lifecycle planning and fleet budgets
Utilize Fleetio and telematics to monitor fleet performance
Oversee vendor management to control total cost of ownership
Integrate acquired fleets and develop the maintenance team
Benefits
Medical, dental, and vision insurance
Life insurance and supplemental plans
401(k) with company match
Paid time off
Employee Assistance Program
Senior leadership role in a fast-growing company
Referral bonus
Full Job Description
Director of Fleet - Greater Tampa area preferred • Full-time • Exempt • $135,000-$150,000/year • Regular travel to company locations • Reports to the Vice President, Operations
The job: You'll lead company-wide fleet strategy and operations for a large, multi-state fleet of trucks, trailers and specialized equipment. You'll own fleet reliability, preventive maintenance, inspections, asset lifecycle, fleet technology, vendor performance and capital planning. You'll also lead DOT and FMCSA compliance across our interstate and intrastate operations. You'll work closely with Operations, Safety, People Services, Finance and field leadership. This is a hands-on leadership role for someone ready to build the systems and standards behind our next stage of growth.
What You'll Do
Set the fleet strategy and consistent maintenance and inspection standards across every location
Lead DOT/FMCSA vehicle compliance, and oversee registrations and credentials including IRP, IFTA and UCR
Improve uptime and reliability, and track roadside inspections, violations, out-of-service events and repeat repairs
Own vehicle lifecycle planning (spec, upfit, deploy, replace, transfer and dispose) and the fleet operating and capital budgets
Lead Fleetio, telematics and fleet KPIs, so leadership has clear visibility into performance, cost and risk
Manage vendors, repair shops, dealers, parts, tire and towing partners to keep total cost of ownership down
Lead fleet due diligence and integration for acquisitions and new-market launches, and develop the fleet and maintenance team
What We're Looking For
8+ years of progressive fleet, transportation or maintenance management, with significant leadership responsibility
Experience leading a large, geographically dispersed commercial fleet, interstate and intrastate; 500+ assets strongly preferred
Strong working knowledge of DOT/FMCSA regulations, CDL requirements and commercial vehicle inspection programs
Hands-on Fleetio or comparable fleet system experience, plus telematics, GPS and diagnostics
Strong data and analytical skills, plus a firm grasp of budgets, lifecycle planning and total cost of ownership
A solid leader and team player with excellent communication skills
Bachelor's or Master's degree in a related field, or equivalent experience
Valid driver's license, willingness to travel regularly, and preferably based in the greater Tampa area
What Success Looks Like
As Director of Fleet, success goes far beyond keeping trucks running-it means building a fleet operation that is safe, compliant, reliable and ready to scale. A successful leader in this role achieves the following:
Higher Uptime: Unscheduled downtime, breakdowns and repeat repairs trend down across every market.
Audit-Ready Compliance: PM and inspection compliance is high, registrations are current, and roadside violations keep falling.
Data-Driven Decisions: Clear fleet KPIs guide when to repair, replace or redeploy assets, and leadership trusts the numbers.
Smart Capital and Cost Control: Budgets are hit, total cost of ownership improves, and vendors are held to clear standards.
Seamless Growth: Acquired fleets and new locations are brought onto our standards, systems and maintenance programs quickly.
What we provide
$135,000-$150,000/year salary
Medical, dental and vision insurance, life insurance, and supplemental plans
401(k) with company match
Paid time off
Employee Assistance Program
A senior leadership role shaping the fleet of a fast-growing, multi-state company
Referral bonus
Physical requirements Regular travel to yards, shops and acquisition sites. Walking yards and climbing in and around trucks and equipment to inspect them, in heat, rain and cold.
How hiring works
Apply, then take a confidential phone screen with our recruiting team.
Interview with the Vice President, Operations and executive leadership.
We run your driver's license through our insurance review, usually the same day.
You get an offer to review and sign online.
You complete one online application, and your background check and any required pre-employment tests are ordered at once.
Once everything clears, we confirm your start date.
