IT Supervisor

The IT Supervisor leads the day-to-day technology needs of the FLASH Family of Companies and is responsible for ensuring IT systems, projects, and priorities are organized, actively managed, and completed on time. A key responsibility of this position is serving as FLASH’s resident expert and primary owner of Trimble TMW Suite, TMT Fleet Maintenance, and related Trimble products and integrations. This individual will develop a strong understanding of how our operations use these systems and continually identify opportunities to improve processes, reporting, data quality, and system utilization. This is a hands-on, on-site leadership position requiring active engagement with employees, departments, and day-to-day operations to provide training and support, manage projects, and identify opportunities for improvement., TMW/TMT & Business Systems

• Serve as the company’s primary internal expert for Trimble TMW Suite, TMT Fleet Maintenance, and related systems and integrations.
• Manage configuration, troubleshooting, upgrades, integrations, reporting, user needs, data integrity, permissions, and system documentation.
• Identify opportunities to better utilize existing technology, improve processes, and eliminate inefficient or manual work.
• Serve as the primary liaison with Trimble and other technology vendors.

Project Management & Department Leadership

• Maintain an organized and prioritized list of IT projects with clear owners, milestones and deadlines, and actively manage projects from initiation through completion.
• Lead and develop IT staff through clear expectations, ongoing coaching, performance feedback, and formal performance evaluations.
• Delegate work appropriately and consistently follow up with employees and vendors to ensure commitments are completed on time.
• Identify roadblocks, drive resolution, and clearly communicate project status and issues to leadership.
• Build processes and documentation that strengthen the department and reduce dependence on any one individual.

Employee Technology Training

• Develop and conduct individual, small-group, and company-wide training on TMW/TMT, Microsoft Outlook, Excel, Microsoft 365, Adobe Acrobat, and other company technology platforms.
• Identify technology skill gaps and provide training and resources to improve employee proficiency and efficiency.
• Develop practical user guides, procedures, and training materials.

IT Operations & Continuous Improvement

• Oversee company computers, servers, networks, applications, mobile devices, communications systems, and cloud services, including planning for upgrades, replacement, and future technology needs.
• Provide hands-on technical support and troubleshooting when needed and ensure IT requests are appropriately prioritized and resolved.
• Maintain technology assets, licensing, user access, cybersecurity, backups, recovery, and system documentation.
• Coordinate technology requirements for employee onboarding and offboarding.
• Partner with department leaders to identify and implement practical technology, reporting, automation, and process improvements that provide measurable business value.
• Assist with IT budgeting, technology purchasing, vendor management, and evaluation of technology investments.

Key Measures of Success

• IT projects are completed on time and within defined scope, with clear owners, milestones, deadlines, and status communication.
• Strong internal expertise and improved utilization of Trimble TMW/TMT.
• Improved employee proficiency with company technology and business applications.
• IT staff are effectively developed, delegated to, and held accountable.
• Critical systems are reliable and secure, with recurring and long-standing technology issues reduced.

• Significant transportation management system experience required; Trimble TMW Suite and/or TMT Fleet Maintenance experience strongly preferred.
• Demonstrated ability to organize, prioritize, and manage multiple projects through completion with strong follow-through and attention to deadlines.
• Experience leading and developing employees, managing vendors, and directing project teams.
• Strong training and facilitation skills with the ability to teach employees with varying levels of technical proficiency.
• Proficiency with Microsoft 365, particularly Outlook and Excel, and common business applications such as Adobe Acrobat.
• Strong analytical, troubleshooting, problem-solving, and communication skills.
• Ability and willingness to work on-site as a regular requirement of the position and travel to other company locations as needed to provide support, training, and implementation of IT projects., * Bachelor’s degree in Information Technology, Computer Science, Management Information Systems, or related field preferred; equivalent professional experience considered.
• Five or more years of progressively responsible IT experience, including supervisory, team lead, or significant project leadership experience, preferred.
• Enterprise software experience in transportation or logistics strongly preferred.