Benefit Specialist; Entry Level

DATTCO has an opening for a full-time Benefits Specialist in New Britain, CT. This is a full-time, on-site position and remote work is not available. The Benefits Specialist provides day-to-day support for the administration of the company’s full suite of employee benefits. This role assists employees across multiple business groups, ensuring timely, accurate processing of benefit elections, responding to inquiries, and supporting compliance activities.

The ideal candidate has at least 1 year of benefits administration experience, strong communication skills, and the ability to manage multiple tasks in a fast-paced environment.

DATTCO is a third-generation, family-owned transportation company and is New England’s largest private passenger transportation company with 2,500 employees. Learn more about us at

• Medical & dental insurance
• Life insurance
• 401k plan with company match
• Flexible spending accounts
• Paid time off
• Room for advancement – we promote from within
• Paid holidays
• Compensation of $/hour

• Support administration of all benefit programs, including medical, dental, vision, life insurance, disability, FSA, EAP, and voluntary benefits.
• Process new hire enrollments, qualifying life events, and terminations.
• Assist with annual open enrollment, including system testing, employee support, and data audits.
• Maintain accurate employee benefit records and audit vendor files for discrepancies.
• Conduct New Hire Orientation as required
• Leave Management & Compliance
  • Support administration of FMLA and other statutory or company-sponsored leave programs.
  • Ensure accurate tracking and documentation of employee leave cases.
  • Provide employees with required forms, timelines, and communication related to leave.
• Employee Support & Communication
  • Serve as the first point of contact for employee benefit questions across multiple employee groups.
  • Communicate benefit information clearly and professionally, both verbally and in writing.
  • Assist in developing benefit communications, FAQs, guides, and orientation materials.
• HR Systems & Data
  • Enter, update, and audit data across HRIS, benefits platforms, and vendor systems.
  • Generate reports, track metrics, and support data integrity initiatives.
  • Identify and escalate system or data issues to the HR Director.
• General HR Support
  • Support HR projects, audits, and cross-functional team initiatives as needed.
  • Assist with vendor relationships, invoice review, and reconciliation.

• Minimum 1 year of experience in benefits administration or HR support with exposure to a full suite of employee benefits.
• Working knowledge of FMLA and basic leave administration processes.
• Strong proficiency in MS Office (Excel, Outlook, Word); ability to quickly learn HRIS and benefit platforms.
• Excellent verbal and written communication skills with the ability to explain benefit concepts clearly.
• Strong organizational and multi-tasking ability; comfortable managing multiple cases, employees, and deadlines at one time.
• High attention to detail, accuracy, and confidentiality.
• Ability to work effectively with multiple employee groups and collaborate across departments.

• Experience with HRIS/benefits administration systems (Paycor, Benefit Advisor)
• Basic understanding of retirement plan compliance (i.e., eligibility, employer match, contribution limits).
• Experience supporting multi-site or multi-group benefit populations.

Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, protected veteran status and any other protected classes.