Job Description

What is Landstar?
Landstar stands for safe, secure and reliable transportation services delivered by our unique network of small business owners. Independent agents and capacity providers operating under the Landstar umbrella enjoy the strength and support of one of the industry’s most stable and successful companies. Our network of independent entrepreneurs provide customers with personalized service at the local level with the global reach and resources of a multi-billion dollar company.

Location: Onsite Saint Augustine, FL
Schedule: Monday - Friday, 8:00am – 5:00pm

What work will you perform?
As the Supervisor of Field Operations at Landstar, you will lead and develop a team dedicated to helping new owner-operators build safe, successful, and profitable businesses. In this highly visible role, you will provide coaching, guidance, and support to both employees and owner-operators, fostering strong relationships that drive engagement, retention, and long-term success. Working closely with cross-functional teams, you will champion safety initiatives, support training and development efforts, and help ensure owner-operators have the tools and knowledge needed to thrive. This position offers the opportunity to expand your knowledge of the transportation industry while making a meaningful impact on business performance, developing talent, and promoting a culture of continuous learning and operational excellence.
Essential Responsibilities:
• Supervise a team of 3-5 staff, including scheduling, training, and collaborating closely with HR on hiring, onboarding, and addressing employee relations concerns.
• Facilitate onboarding and acclimation of new owner-operators to Landstar systems through Field Operations Centers, safety meetings, and other events; provide training support in the absence of the Orientation Coordinator.
• Support and provide direction to Advisors, Orientation and Continuous Awareness of Business and Safety (CABS) Coordinators, and Field Representatives.
• Develop and maintain content for Owner-Operator Orientation, covering safety, business, and securement training.
• Monitor and review operational data in AS400 and Power BI, proactively identifying trends and preparing reports for leadership meetings regarding performance metrics and potential issues.
• Coordinate staff meetings and ongoing goal setting; assess continuing education needs for Business Capacity Owners (BCOs) and facilitate relevant training.
• Assist with maintaining FOC property, including interviewing and communicating with vendors for facility maintenance and additional projects.
Required Minimum Experience and Education:
• High school Diploma/GED
• One year of experience in internal customer service, training, coaching, or mentoring individuals in a business environment
Preferred Experience and Education:
• One year of experience in transportation, logistics, safety, training, or operations
Knowledge, Skills, and Abilities:
• Proficiency with Microsoft Office Suite (Word, PowerPoint, Excel, Access), AS400, and Power BI.
• Strong presentation development and delivery skills.
• Excellent problem-solving capabilities.
• Outstanding verbal and written communication skills.
• Analytical mindset with strong interpersonal skills to build effective working relationships.
• Exceptional organizational and time management abilities.
• Proven ability to lead, motivate, and inspire others.

Why work at Landstar?
Landstar is seeking hard-working and dedicated employees committed to exceeding the expectations of those we serve. We employ a highly diverse workforce and welcome employees from all cultures and backgrounds to our team.

Our workplace culture is second-to-none. Landstar provides a safe and professional work environment in which to thrive and grow. We offer competitive compensation, robust benefit plans including affordable medical plans, employer 401(k) match, paid time off, tuition assistance and much more.

If you want to be part of a top-notch transportation company with an emphasis on safety, service, teamwork, and dedication then Landstar is the place for you!

Landstar is an Equal Opportunity/Affirmative Action employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin or any other characteristic protected by federal, state or local laws. Landstar will provide reasonable accommodation to applicants with disabilities where appropriate. Applicants requiring reasonable accommodation for any part of the application and hiring process should send an e-mail to employment@landstar.com.

Privacy Policy

Landstar uses application information only for employment related purposes, including background investigations and regulatory compliance. Landstar will not disclose the information to any other person or entity, unless compelled by force of law. Landstar stores your application information on computers operated by Ceridian. This on-line application software is provided by Ceridian under an agreement which specifies that Ceridian will not disclose or make any use of application information stored on its secure servers.