Senior Benefits Analyst

Skyward Service Company; Houston (TX); On-site; USD 90,000 - 110,000; Full time

Benefits offered by this job

Health benefits

Tuition assistance

401k savings

Employee Stock Purchase Program

Paid time off

Paid holidays

Child bonding leave

Employee assistance

Job summary

Skyward Specialty seeks a Senior Benefits Analyst to lead administration, compliance, and improvement of our employee benefits and multi-state leave programs for a distributed workforce.

The role focuses on FMLA, ADA, disability, and state leaves (NY/NJ), plus health and welfare benefits, retirement programs, vendor management, reporting, and AI-enabled process enhancements to deliver a compliant, efficient benefits experience.

Qualifications

• 5+ years of benefits and leave administration experience.
• Experience with complex multi-state leave programs (NY, NJ).
• Strong analytical and communication skills with discretion.

Responsibilities

• Lead leave of absence administration including FMLA/ADA/disability programs and state leaves.
• Administer health, welfare, and retirement benefit programs; manage enrollments and vendor relations.
• Develop reports, ensure compliance, and drive process improvements using approved tools.

Skills

Benefits administration

Leave administration

Multi-state leaves

Advanced Excel

Data analysis

Communication skills

Education

Bachelor's degree in HR/Business/Finance

Tools

Workday

Job description

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.

• health and welfare benefits
• tuition and professional certification assistance
• 401k savings
• elective participation in the Employee Stock Purchase Program
• paid time off
• paid holidays
• child bonding leave
• other employee assistance

Skyward Specialty is a rapidly growing and innovative specialty insurance company, delivering commercial P&C products and solutions on a non-admitted and admitted basis. The Company operates through eight underwriting divisions – Accident & Health, Captives, Global Property & Agriculture, Industry Solutions, Professional Lines, Programs, Surety and Transactional E&S. At Skyward Specialty, we approach insurance differently. Our specialty insurance experts are empowered to dig deeper to customize solutions that help brokers and agents deliver impactful solutions to their clients. We operate at the complex end of the specialty market and leverage technology to bring disruptive, innovative insurance solutions to market. We are agile and steadfastly focused on our strategy to lead in the select markets in which we choose to do business. We call this our rule our niche strategy.