Director of Benefits
Dental Care Alliance•Sarasota, FL
•Remote
About The Position
The Director of Benefits is responsible for supporting the strategic design, implementation, and administration of the organization’s employee benefits programs. This role ensures that benefit offerings are competitive, cost-effective, compliant with regulations, and aligned with the company’s overall talent strategy.
Requirements
- 10+ years of progressive experience in benefits administration or total rewards
- 3–5+ years of leadership or management experience
- Deep knowledge of employee benefits programs and regulatory requirements
- Strong analytical, financial, and negotiation skills
- Excellent communication and leadership abilities
Nice To Haves
- Master’s degree
- Relevant certifications preferred (e.g., CEBS, CBP, SHRM-CP/SCP)
Responsibilities
- Oversee and manage end-to-end administration of benefits programs including medical, dental, vision, life, disability, FSA/HSA, and 401(k)
- Oversee worker’s compensation, and leave administration programs
- Partner with Total Rewards and Finance to align benefits strategy objectives (cost control, scalability, ROI) while maintaining competitive offerings
- Support plan design, renewals, and contribution strategies across a distributed, multi-state workforce
- Handle escalated employee benefits issues and provide guidance on complex cases
- Oversee benefits budgeting, forecasting, and cost-control initiatives
- Manage relationships with external vendors, brokers, and consultants
- Support benefits budgeting, forecasting, and cost containment initiatives
- Analyze claims data and utilization trends to inform executive decision-making
- Identify efficiency opportunities through plan design and vendor optimization
- Lead benefits-related workstreams for acquisitions, including due diligence and integration
- Evaluate legacy benefit plans and manage transitions into DSO-sponsored programs
- Partner with HR, Legal, and Integration teams for smooth employee transitions
- Oversee high-volume onboarding and enrollment processes
- Ensure compliance with ERISA, ACA, COBRA, HIPAA, and multi-state regulations
- Manage Form 5500 filings, nondiscrimination testing, and audits
- Maintain plan documents, SPDs, and required notices
- Partner with legal and external advisors during acquisitions and audits
- Oversee compliance and license tracking such as CPR, Hygiene and dentist licenses, vaccines, OIG, DEA, PALS, CDS, and malpractice
- Serve as functional lead for benefits administration within UKG
- Configure benefit plans, eligibility rules, and workflows
- Ensure integrations between UKG, carriers, and payroll
- Lead system testing and drive automation improvements
- Manage relationships with brokers, carriers, and TPAs
- Support RFP processes and vendor negotiations
- Monitor service levels and resolve escalated issues
- Lead annual open enrollment across a dispersed workforce
- Develop targeted, easy-to-understand communications
- Ensure system readiness and payroll accuracy
- Supervise and develop benefits team members
- Standardize processes across legacy and acquired practices
- Drive continuous improvement in efficiency and employee experience
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What This Job Offers
Job Type
Full-time
Career Level
Director
