Senior Benefits Analyst

Skyward Specialty Insurance

. Serve as the primary subject matter expert for all leave of absence programs, including FMLA, ADA accommodations, short- and long-term disability, state-paid family and medical leave programs, and unpaid leaves .

Posted 9/15/2026full-timeHouston • Texas • United StatesSenior💰 $90,000 - $110,000 per yearWebsite

Core Competencies

Role fit

Core Competencies

Use this summary to align your resume positioning with the role.

Demonstrates expertise in managing leave of absence programs, including FMLA and ADA, while ensuring compliance with federal and state regulations. Proficient in data analysis and reporting to enhance benefits administration and operational efficiency.

Highest-signal resume keywords

Leave Of Absence ManagementFMLA AdministrationADA AccommodationsAdvanced Excel SkillsBenefits Compliance

ATS Keywords

Tailor your resume

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard Skills

Leave AdministrationData AnalysisBenefits AdministrationPayroll CoordinationCase ResolutionVendor ManagementRegulatory ReportingMulti-State Leave ProgramsRetirement Benefits AdministrationEmployee Benefits Communication

Soft Skills

Analytical SkillsProblem-SolvingOrganizational SkillsCommunication SkillsDiscretion

Tools & Technologies

WorkdayReporting ToolsAI-Enabled Solutions

Industry Keywords

ERISAACACOBRAHIPAAHealth And Welfare BenefitsDisability ProgramsState-Paid Family LeaveNew York Leave RequirementsNew Jersey Leave Requirements

About the role

Key responsibilities & impact

Serve as the primary subject matter expert for all leave of absence programs, including FMLA, ADA accommodations, short- and long-term disability, state-paid family and medical leave programs, and unpaid leaves
Manage the full leave lifecycle, including intake, eligibility review, documentation, payroll coordination, return-to-work processes, accommodations, and case resolution
Monitor federal, state, and local leave regulations and recommend policy, process, and communication updates
Partner with managers, HR, Payroll, Legal, and third-party administrators to address complex leave situations and escalations
Maintain leave reporting, audits, and employee communications
Administer health and welfare, retirement, and voluntary benefit programs
Manage benefit enrollments, vendor file feeds, billing, invoicing, audits, and payroll-related reconciliations
Support benefit plan operations, employee inquiries, and vendor issue resolution
Assist with open enrollment planning, employee education, and ongoing benefits communications
Develop and maintain reports related to benefits, leave, compliance, and workforce trends
Analyze data to identify discrepancies and opportunities for process improvement
Support compliance requirements, audits, plan documentation, and regulatory reporting
Leverage technology, reporting tools, and approved AI-enabled solutions to improve efficiency and enhance service delivery
Partner with Human Resources, Payroll, Finance, Legal, and external vendors to deliver a compliant, efficient, and employee-focused benefits experience

Requirements

What you’ll need

5+ years of progressive experience in employee benefits and leave administration
Significant hands-on experience administering complex multi-state leave programs, including FMLA, ADA, disability programs, state-paid family and medical leave programs, and New York and New Jersey leave and disability requirements
Experience partnering with third-party administrators and insurance carriers
Experience administering health and welfare benefit programs, including medical, dental, vision, life, and disability plans
Advanced Excel skills and experience working with benefits, payroll, and leave-related data
Strong analytical, problem-solving, organizational, and communication skills
Ability to manage sensitive and confidential information with discretion
Bachelor's degree in Human Resources, Business Administration, Finance, or a related field, or equivalent experience preferred
Workday experience, particularly Benefits and Reporting functionality preferred
Experience administering retirement benefit programs preferred
Knowledge of ERISA, ACA, COBRA, HIPAA, and related benefits regulations preferred
Experience supporting a large, multi-state workforce preferred
Familiarity with AI-enabled tools and technology used to improve reporting, research, and operational efficiency preferred