SlipstreamJobsFresh Startup & VC-Backed Jobs

Senior Benefits & Leave Specialist

Slide Insurance - Tampa, FL, USA - In-office - posted 2026-08-29

Apply on the company site

SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.

Slide Insurance is seeking a Senior Benefits & Leave Specialist to support their people operations and culture. This role is central to administering and managing employee benefits and leave programs while ensuring compliance and delivering excellent employee experience. In Benefits Administration, you will manage the full lifecycle of employee benefit programs including self-insured medical, dental, vision, life, disability, HSA, FSA, and voluntary benefits. You'll handle enrollments, life events, changes, terminations, and data maintenance. You'll serve as the primary resource for employee benefit questions regarding eligibility, coverage, and deductions. You'll partner with brokers, carriers, and third-party administrators to resolve issues, support annual enrollment activities, and conduct audits and reconciliations to maintain accurate records. For Leave Administration & Accommodations, you'll be the primary internal resource for leave programs and workplace accommodations. You'll coordinate with third-party leave administrators on activity, communications, escalations, and return-to-work processes. You'll manage accommodation requests and facilitate the interactive process with employees and leaders while maintaining confidentiality and ensuring compliance with leave and accommodation requirements. You'll also support compliance and process improvement by ensuring benefits and leave administration align with regulations, plan requirements, and company policies. You'll perform audits, reporting, data validation, and documentation to support compliance and internal controls. You'll identify opportunities to improve processes, communications, system functionality, and vendor performance. Additionally, you'll provide backup payroll support including benefit deductions and leave-related payroll impacts. Required qualifications include a bachelor's degree in HR, Business Administration, or related field (or equivalent experience), 4+ years of progressive experience in benefits administration, leave administration, or HR operations with self-insured medical plan experience, and proficiency with HRIS and benefits administration systems (ADP preferred). You should have strong knowledge of employee benefits, FMLA, ADA, HIPAA, USERRA, and multi-state leave requirements. Professional certifications (SHRM-CP, PHR, CEBS) are preferred. Strong Excel skills, analytical abilities, and proven relationship-building skills are essential.

Similar roles