Senior Benefits & Leave Specialist

Slideinsurance
Tampa
Career-pivot friendly

Who this role is best for

Aimed at mid-to-senior level HR professionals with benefits administration expertise who thrive in collaborative, innovation-driven environments.

Best fit for

  • Candidates with 4+ years of benefits administration experience and a background in multi-state or regulated environments
    — “4+ years of progressive experience in benefits administration, leave administration, HR operations, or a related area, including self-insured medical plan experience
  • Professionals who have managed employee leave programs and workplace accommodations in a multi-state organization
    — “Serve as the primary internal resource for leave programs and workplace accommodations
  • Individuals who have experience with HRIS systems and can coordinate with third-party vendors and brokers
    — “Experience working with benefits brokers, carriers, third-party administrators, leave management vendors, and payroll processes

Things to consider

  • The role requires a strong understanding of USERRA, FMLA, ADA, and state-specific leave laws
    — “Strong knowledge of employee benefits administration, including self-funded medical and disability plans, and working knowledge of FMLA, ADA, HIPAA, USERRA, and applicable state leave requirements
  • Candidates should be prepared to handle confidential employee data and ensure compliance with regulations
    — “Maintain confidentiality and support compliance with applicable leave and accommodation requirements

How to stand out

  • Emphasize experience with self-insured medical plans and multi-state compliance in your resume and interview responses
    — “including self-insured medical plan experience
  • Highlight your ability to identify and implement process improvements in benefits and leave administration
    — “Identify opportunities to improve processes, employee communications, system functionality, and vendor performance
  • Showcase your collaboration with vendors and your ability to manage complex employee interactions
    — “Partner with brokers, carriers, and third-party administrators to resolve enrollment, eligibility, billing, and employee issues
  • Demonstrate strong Excel skills and data validation experience in your application materials
    — “Strong Excel skills preferred
Pace · SteadyCollaboration · HighAutonomy · MediumDecision Impact · Team

Derived from job-description analysis by Serendipath's career intelligence engine.

What success looks like

  • accurate benefit enrollments
  • compliance with regulations
  • employee satisfaction
Typical background
4+ years of progressive experience in benefits administration, leave administration, HR operations

Skills & requirements

Required

Benefits AdministrationLeave AdministrationHRIS ManagementComplianceProcess ImprovementEmployee Support

Preferred

Shrm-cp, PHR, CEBS Certification

Stack & domain

ADPFMLAADAHIPAAUserraShrm-cpPHRCEBSHuman ResourcesBenefits AdministrationLeave Administration

About the role

Original posting from Slideinsurance via Greenhouse

Slide Insurance - Fun. Innovation Driven. Fueled by Passion, Purpose and Technology.

At Slide, you will not only be part of a successful team, but you will also be a part of our Slide Vibe/award winning culture where collaboration and innovation are expected, recognized and awarded!

As a Senior Benefits & Leave Specialist, you'll play an important role in supporting what makes Slide unique: our people.   From benefits and leave administration to workplace accommodations, you'll help employees navigate important moments in their lives while reinforcing the culture, care, and support that define the Slide Vibe.

What You'll Do

Benefits Administration & Employee Support

Administer employee benefit programs, including self-insured medical, dental, vision, life, disability, HSA, FSA, and voluntary benefits

Manage benefit enrollments, life events, changes, terminations, and employee data maintenance

Serve as a primary resource for employee benefit questions, eligibility, coverage, and deductions

Partner with brokers, carriers, and third-party administrators to resolve enrollment, eligibility, billing, and employee issues

Support annual enrollment activities, employee communications, system testing, and data validation

Review benefit invoices, perform audits and reconciliations, and maintain accurate benefit records

Leave Administration & Accommodations

Serve as the primary internal resource for leave programs and workplace accommodations

Partner with the third-party leave administrator to coordinate leave activity, employee communications, escalations, and return-to-work processes

Manage workplace accommodation requests and facilitate the interactive process with employees and leaders

Monitor leave activity, status changes, and key dates to ensure accurate HRIS and payroll updates

Maintain confidentiality and support compliance with applicable leave and accommodation requirements

Compliance, Process Improvement & Payroll Support

Support benefits and leave administration in accordance with applicable regulations, plan requirements, and company policies

Perform audits, reporting, data validation, and documentation to support compliance and internal controls

Identify opportunities to improve processes, employee communications, system functionality, and vendor performance

Provide backup payroll support, including benefit deductions, leave-related payroll impacts, and payroll validation activities

What You Bring

Bachelor's degree in Human Resources, Business Administration, or a related field, or an equivalent combination of education and experience

4+ years of progressive experience in benefits administration, leave administration, HR operations, or a related area, including self-insured medical plan experience

Experience administering benefit and leave programs, including annual enrollment, employee communications, vendor coordination, and multi-state leave requirements

Experience working with benefits brokers, carriers, third-party administrators, leave management vendors, and payroll processes

Experience with HRIS and benefits administration systems; ADP experience preferred

Experience in a multi-state, regulated, financial services, insurance, or publicly traded organization preferred

SHRM-CP, PHR, CEBS, or similar professional certification preferred

Strong knowledge of employee benefits administration, including self-funded medical and disability plans, and working knowledge of FMLA, ADA, HIPAA, USERRA, and applicable state leave requirements

Strong analytical, organizational, problem-solving, communication, and customer service skills, with the ability to manage multiple priorities and maintain confidentiality

Proven ability to build effective relationships with employees, leaders, vendors, and business partners while delivering a positive employee experience

Strong Excel skills preferred

Commitment to living Slide's Core Values

What Slide Offers To You

The Slide Vibe - An opportunity to be a part of a fun and innovation-driven culture fueled by Passion, Purpose and Technology! Slide offers many opportunities to collaborate and innovate across the company and departments, as well as get to know other Sliders. From coffee chats, to clubs, to social events - we plan it, so all Sliders feel included and Enjoy their Journey.

Benefits - Created using Slider feedback, Slide offers a comprehensive and affordable benefits package to cover all aspects of health...Physical, Emotional, Financial, Social and Professional. A Lifestyle Spending Account is set up for each Slider and Slide contributes to it monthly for use on any benefit that individually suits you - Health Your Way!

2023 - 2026 BEST PLACE TO WORK - Tampa Bay Business Journal   

2024, 2025 & 2026 TOP WORKPLACE - Tampa Bay Times   & USA TODAY

Source: Slideinsurance careers (Greenhouse)

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