Demo

Director of Fleet and Maintenance - Contractor

Casella Construction, Inc.
Pittsford, VT Contractor
POSTED ON 9/27/2025
AVAILABLE BEFORE 10/27/2025

Casella Construction is seeking to hire a Contractor for the position of Director of Fleet & Maintenance to join our team in Pittsford, Vermont for a two-to-three-year assignment. The Contractor has full P&L responsibility for a $16M heavy civil and class 7-8 truck maintenance organization and provides leadership of the Fleet Maintenance Department. Casella Construction has restructured the maintenance division by combining the off-road and on-road functions together into one primary facility at our headquarters, which creates an exciting opportunity for the right strategic leader. The Contractor interfaces with our operational departments to understand the priorities of the company and ensures the maintenance organization is fully staffed, trained, and prepared to support the company’s fleet goals. The Contractor will take ownership of developing future leaders through talent management and employee development processes. High potentials have been identified for leadership roles within the function.

The person in this position will demonstrate exceptional customer service characteristics, agility, and mechanical aptitude. The best candidate will be a safety-first leader who has in-depth leadership experience troubleshooting and repairing diesel, gas, mechanical, hydraulic, electrical and emission systems for Dozers, Excavators, Feller Bunchers, Crushers, Loaders, Rollers, Screens, Skid Steers, Trailers, Trucks/Tractors, and Low Beds.

Responsibilities:

  • Provides direct leadership for employees across two shops supporting daily operations for 30 total staff.
  • Works in conjunction with division managers and maintenance staff to hire and onboard various positions within the maintenance organization that will ensure the necessary level of support for the fleet.
  • Engages with division leads in building and managing the priorities for the daily, weekly, and monthly maintenance
  • Drives Preventative Maintenance Programs and refines and develops new programs as needed.
  • Oversees fleet utilization and balances ownership and rental needs.
  • Manages external vendor relationships.
  • Provides business continuity across the maintenance organization.
  • Develops, executes, and monitors ROI justifications for maintenance spend on relevant capital repairs and asset replacements, maintains the maintenance budget, and develops KPI’s for the division while partnering with the Manager of Fleet Finance & Warranty Procurement.
  • Leads 5-year annual Capital Planning process for fleet acquisitions.
  • Collaborates with the Maintenance Staff to facilitate the proper training and development of employees.
  • Understands, utilizes, and ensures proper compliance with the use of company’s maintenance management software (B2W) to input work orders, manage the fleet, place labor hours against work orders, inventory, and assets. Will become the B2W super-user for the maintenance area.
  • Oversees operations-related asset management activities and metrics.
  • Training requirements, both in person and online, as needed or required.

Qualifications:

  • High School Diploma or GED.
  • At least five years of experience in a management maintenance role.
  • Seven years or more of experience in a fleet maintenance environment.
  • Knowledge of diesel, gas, mechanical, hydraulic, electrical, and emission systems.
  • Experience with and knowledge of FMCSA DOT, MSHA, and OSHA regulations.
  • Certified AEMP preferred, or other trucking industry certification desired.

Attributes:

  • Excellent internal and external customer support skills with the ability to multi-task and manage numerous responsibilities in a fast-paced organization.
  • Ability to analyze and interpret financial information/fleet data/KPI’s.
  • Work collaboratively in an inclusive maintenance environment.
  • Ability to effectively plan and develop long-range strategies that accomplish objectives.
  • Strong bias for action and a sense of urgency. Resolve issues quickly.
  • Analyze and diagnose problems, develop solutions, and recommend an effective course of action.
  • A high degree of ethics and integrity to do the right thing in the right way.
  • Demonstrate leadership capabilities by taking the initiative to build, develop, and motivate the team through effective communication, managing conflict, and problem-solving.
  • Have a follow-through mentality in creating accountability and consistency for the team by bringing an issue, project, or process to completion.

Casella Construction offers a competitive salary along with a comprehensive benefits package that includes medical, dental, vision, long and short-term disability, supplemental insurances, and 401(k) retirement options including a company match.

About our Company:

Joseph Casella and John Casella are the second generation of the Casella family who are determined to carry on the successful growth and profitability Casella Construction has experienced throughout the years. We are fortunate to have and continue to expand a superlative team of people throughout the organization who are constantly expanding critical areas of our business; namely, heavy highway construction, utility installation, environmental contracting, commercial site development, demolition, aggregate, and transportation. In large part, Casella Construction's success is attributed to our capabilities and adaptability in creating dynamic solutions that enable us to remain in the forefront of technology and environmental stewardship.

If your compensation planning software is too rigid to deploy winning incentive strategies, it’s time to find an adaptable solution. Compensation Planning
Enhance your organization's compensation strategy with salary data sets that HR and team managers can use to pay your staff right. Surveys & Data Sets

What is the career path for a Director of Fleet and Maintenance - Contractor?

Sign up to receive alerts about other jobs on the Director of Fleet and Maintenance - Contractor career path by checking the boxes next to the positions that interest you.
Income Estimation: 
$49,829 - $67,442
Income Estimation: 
$60,250 - $88,519
Income Estimation: 
$43,945 - $66,104
Income Estimation: 
$60,250 - $88,519
Income Estimation: 
$82,393 - $113,057
Income Estimation: 
$43,945 - $66,104
Income Estimation: 
$82,393 - $113,057
Income Estimation: 
$95,438 - $138,796
View Core, Job Family, and Industry Job Skills and Competency Data for more than 15,000 Job Titles Skills Library

Job openings at Casella Construction, Inc.

Casella Construction, Inc.
Hired Organization Address Pittsford, VT Full Time
Casella Construction is seeking to hire a Director of Fleet & Maintenance to join our team in Pittsford, Vermont. The Di...
Casella Construction, Inc.
Hired Organization Address Saint Johnsbury, VT Full Time
Are you ready to build your future? Explore exciting opportunities in Construction where entry level positions can lead ...
Casella Construction, Inc.
Hired Organization Address Pittsford, VT Full Time
The Facilities Maintenance Specialist is a self-starter who is responsible for a wide range of seasonal maintenance task...
Casella Construction, Inc.
Hired Organization Address Pittsford, VT Full Time
Casella Construction is hiring a Safety Coordinator to join the Safety Department. The Safety Coordinator is responsible...

Not the job you're looking for? Here are some other Director of Fleet and Maintenance - Contractor jobs in the Pittsford, VT area that may be a better fit.

Director of Fleet and Maintenance

Casella Construction, Inc., Pittsford, VT

Manager, Fleet Maintenance

Dairy Farmers of America, Inc., Enosburg Falls, VT

AI Assistant is available now!

Feel free to start your new journey!