Senior Benefits & Leave Strategy Analyst

Skyward Specialty Insurance; Kennesaw (GA); On-site; USD 90,000 - 110,000; Full time

Benefits offered by this job

Health and welfare benefits

Tuition assistance

401(k) plan

Employee Stock Purchase Program

Job summary

Skyward Specialty Insurance seeks an experienced Senior Benefits Analyst to oversee leave of absence programs, health and welfare plans, retirement offerings, and vendor relationships for a nationwide workforce. The role emphasizes multi-state leave requirements (including NY and NJ) and compliance, while driving process improvements.

You will partner with HR, Payroll, Legal, and external vendors to ensure accurate reporting, audits, and employee communications, and to drive data-driven

Qualifications

• 5+ years of progressive experience in employee benefits and leave administration.
• Significant hands-on experience administering complex multi-state leave programs (FMLA, ADA, disability, NY/NJ leave) with third-party admins.
• Experience administering health and welfare, retirement, and voluntary benefit programs.
• Advanced Excel skills and experience with benefits, payroll, and leave data.
• Strong analytical, problem-solving, organizational and communication skills with discretion.

Responsibilities

• Serve as the primary SME for all leave of absence programs (FMLA, ADA, disability, state leaves).
• Manage full leave lifecycle: intake, eligibility, documentation, payroll coordination, return-to-work, case resolution.
• Monitor leave regulations and update policies/processes to maintain compliance.
• Support benefits operations, vendor file feeds, billing, audits, and inquiries.

Skills

5+ years experience

Multi-state leaves

Analytical skills

Strong communication

Discretion with information

Education

Bachelor's degree in HR/related field

Tools

Excel (Advanced)

Workday

Job description

Skyward Specialty Insurance seeks an experienced Senior Benefits Analyst to oversee leave of absence programs, health and welfare plans, retirement offerings, and vendor relationships for a nationwide workforce. The role emphasizes multi-state leave requirements (including NY and NJ) and compliance, while driving process improvements.

You will partner with HR, Payroll, Legal, and external vendors to ensure accurate reporting, audits, and employee communications, and to drive data-driven