Senior Benefits Operations & Compliance Leader

Jobtailor; Sarasota (FL); On-site; USD 65,000 - 95,000; Full time

Job summary

Jobtailor is seeking a Senior Benefits Administrator to oversee all benefit programs, ensure compliant processing, and manage escalations for employee inquiries. You will coordinate with carriers, brokers, and TPA partners while supporting vendor transitions and system updates.

Ideal candidates will have a bachelor’s degree or equivalent experience and 5–7+ years in benefits administration, with strong attention to detail and knowledge of regulations.

Qualifications

• Bachelor's degree or equivalent experience preferred.
• 5–7+ years of experience in benefits administration (US or Canada; union experience a plus).
• Strong attention to detail and ability to manage multiple priorities.
• Solid working knowledge of benefits regulations and plan administration processes.
• Proficiency in HRIS systems; Dayforce experience preferred but not required to be deep/technical.
• Ability to troubleshoot issues and escalate appropriately.

Responsibilities

• Oversee daily operations of all benefit programs, including health, dental, vision, disability, life, retirement, and ancillary plans.
• Ensure benefit eligibility, enrollment, qualifying life events, and payroll deductions are processed accurately.
• Serve as the second‑level escalation point for employee benefit inquiries.
• Oversee day‑to‑day interactions with carriers, brokers, and third‑party administrators.
• Support benefit-related projects, such as vendor transitions, system updates, and M&A integration tasks.

Skills

Benefits Administration

HRIS Proficiency

Benefits Regulations Knowledge

Employee Benefit Inquiries Management

Attention to Detail

Education

Bachelor’s degree or equivalent experience

Tools

HRIS Systems

Dayforce

Job description

Jobtailor is seeking a Senior Benefits Administrator to oversee all benefit programs, ensure compliant processing, and manage escalations for employee inquiries. You will coordinate with carriers, brokers, and TPA partners while supporting vendor transitions and system updates.

Ideal candidates will have a bachelor’s degree or equivalent experience and 5–7+ years in benefits administration, with strong attention to detail and knowledge of regulations.