Benefits Analyst

Job ID: 11885Req ID: 3444Location: Landstar System, Inc., 13410 Sutton Park Dr S, Jacksonville, Florida, United States of AmericaPosted: 2026-11-03Pay Type: Salary 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. What work will you perform? As the Benefits Specialist you will administer and continuously improves Landstar’s employee benefits programs, ensuring exceptional employee experience while maintaining compliance, operational excellence, and cost effectiveness. This role serves as a primary subject matter resource for health and welfare plans, retirement programs, leave administration, and benefit vendor partnerships. As the Benefits Specialist you will provide consultative support to employees, leaders, vendors, and HR partners while using data and industry trends to recommend enhancements to benefit programs, processes, and communications. The position combines hands-on administration with analytical responsibilities that support Landstar’s Total Rewards philosophy. Essential Responsibilities: Administer health, welfare, retirement, and voluntary benefit programs, including enrollments, changes, terminations, qualifying life events, and beneficiary updates. Ensure accurate processing and reconciliation of benefit transactions across the HRIS, payroll, carriers, and third-party administrators. Administer 401(k) activities, including enrollments, contribution changes, loan processing, compliance coordination, and employee education. Maintain accurate benefit records, reports, files, and documentation in accordance with plan and regulatory requirements. Support annual compliance activities, including Form 5500 preparation, plan audits, nondiscrimination testing, and required notices and filings. Support compliance with ERISA, COBRA, HIPAA, ACA, applicable Internal Revenue Service requirements, Department of Labor requirements, and other benefit regulations. Maintain plan documents, summary plan descriptions, employee notices, and related governance materials. Coordinate wellness initiatives and support employee wellbeing programs. Serve as a primary point of contact for employee, beneficiary, and retiree benefit questions, escalations, and issue resolution. Explain benefit programs clearly and help employees make informed enrollment decisions. Support onboarding and new-hire orientation by presenting benefit offerings, eligibility requirements, and enrollment procedures. Required Minimum Experience and Education: Bachelor’s degree in related field or equivalent experience 5 years of employee benefits administration experience Preferred Experience and Education: 2 years of experience administering health and welfare plans, retirement plans, and leave programs. CEBS, CBP, SHRM-CP, SHRM-SCP, PHR, SPHR, or another relevant professional certification. 2 years of experience working with a multi-state employee population. Knowledge, Skills, and Abilities: Ability to use Microsoft Office efficiently Strong knowledge of employee benefits administration, related regulations and compliance requirements Ability to analyze data, identify trends, and develop practical recommendations. Excellent attention to detail, organization, follow-through, and recordkeeping. Strong customer service, judgment, and problem-solving capabilities. Ability to communicate complex benefit information in a clear, accurate, and employee-friendly manner. Strong relationship management skills with employees, vendors, and internal partners. Ability to manage multiple priorities while maintaining accuracy, discretion, and confidentiality. Continuous improvement mindset with a focus on operational excellence and employee experience. ** This job posting is not designed to cover or contain a comprehensive listing of all activities, duties or responsibilities that are required of the employee. Duties, responsibilities and activities may change, or new ones may be assigned at any time with or without notice. 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 View email address on click.appcast.io . 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.