Senior Benefits Analyst

Skyward Specialty is seeking an experienced Senior Benefits Analyst to support the administration, compliance, and continuous improvement of our employee benefits and leave of absence programs.

This role serves as a key subject matter expert for employee benefits, with a strong emphasis on multi-state leave administration. The ideal candidate brings deep experience managing complex leave programs across multiple states, including New York and New Jersey leave and disability requirements, while supporting a geographically dispersed workforce.

In addition to leave administration, this role supports health and welfare benefits, retirement programs, vendor management, compliance, reporting, employee communications, and process improvement initiatives. The Senior Benefits Analyst partners closely with Human Resources, Payroll, Finance, Legal, and external vendors to deliver a compliant, efficient, and employee-focused benefits experience.

Principal Duties and Responsibilities

Leave Administration & Compliance

• 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 to maintain compliance.
• Partner with managers, HR, Payroll, Legal, and third-party administrators to address complex leave situations and escalations.
• Maintain leave reporting, audits, and employee communications.

Benefits Administration

• 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.

Analysis, Reporting & Operations

• 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.

Knowledge, Skills, and Abilities

Required Qualifications

• 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, while 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, with the ability to manage sensitive and confidential information with discretion.

Preferred Qualifications

• Bachelor's degree in Human Resources, Business Administration, Finance, or a related field, or equivalent experience.
• Workday experience, particularly Benefits and Reporting functionality.
• Experience administering retirement benefit programs.
• Knowledge of ERISA, ACA, COBRA, HIPAA, and related benefits regulations.
• Experience supporting a large, multi-state workforce.
• Familiarity with AI-enabled tools and technology used to improve reporting, research, and operational efficiency.

Compensation & Benefits

The applicable base salary for this opportunity is $90,000 - $110,000. The base pay offered will be determined by factors such as experience, skills, training, location, certifications, education, and any applicable minimum wage requirements. In addition to the base salary, this opportunity may be eligible for performance-based incentives.​ We are excited to offer a competitive total rewards package which includes health and welfare benefits, tuition and professional certification assistance, 401k savings, elective participation in the Employee Stock Purchase Program, paid time off, paid holidays, and child bonding leave, as well as other employee assistance.