Sr. Benefits Analyst

Overview

Join Our Team at Wheels Up

At Wheels Up, we're proud to be a global leader in on-demand private aviation. As one of the largest companies in the industry and a strategic partner of Delta Air Lines – we are committed to making private air travel safe, reliable, and enjoyable. With a diverse fleet of owned aircraft plus a global network of trusted charter operators, we offer our customers access to the right aircraft for their needs and the ability to fly on their terms.

 

And it doesn’t stop at private flights. Wheels Up also provides freight services, safety and security solutions, and managed services to individuals, businesses, government agencies, and more. Regardless of how, when or where you want to fly, our mission is simple; deliver a premium, personalized aviation experience for every customer.

 

We anticipate closing applications submissions for this role on 4/11/25. If the deadline is extended, we will update this job posting accordingly.

Responsibilities

Role Overview: What You’ll Be Doing

The Senior Benefits Analyst will play a critical role in the management, analysis, and optimization of the company’s benefits programs. This position requires advanced knowledge of benefits administration, regulatory compliance, data analysis, and vendor management. The Senior Benefits Analyst will work closely with the HR leadership team to drive strategic initiatives and ensure the continued success of our benefits offerings.

 

Your Key Responsibilities (Essential Functions)

• Manage and analyze the effectiveness of company benefits programs, recommending improvements and adjustments as needed
• Oversee complex benefits administration tasks, such as eligibility audits, compliance reporting, and vendor management
• Collaborate with HR leadership to design and implement benefits strategies that align with company goals and objectives
• Lead the open enrollment process, including preparation, communication, and vendor coordination
• Provide advanced support to employees on complex benefits issues, resolving escalated inquiries and concerns
• Ensure compliance with all relevant federal, state, and local benefits regulations, including ACA, ERISA, and HIPAA
• Perform benefits benchmarking and market analysis to ensure competitive offerings
• Prepare and deliver detailed benefits reports to leadership and external partners, including cost analysis, trends, and recommendations
• Lead or support the management of wellness programs and other health-related initiatives
• Provide mentorship and training to junior members of the benefits team
• Leave of Absense administration

Qualifications

What You Bring to the Table: Education & Certification Requirements

We’re looking for someone who has a unique mix of experience, skills, and passion for what we do:

• 3-5 years of experience in benefits analysis or administration, with a solid understanding of benefits strategy and compliance
• Advanced knowledge of benefits programs, including health, dental, vision, life insurance, retirement, and wellness programs
• Strong expertise in benefits data analysis, benchmarking, and vendor management.
• In-depth knowledge of federal and state benefits regulations (ACA, ERISA, HIPAA)
• Proficiency in HRIS and benefits management systems, with advanced Excel skills for reporting and data analysis
• Exceptional communication and interpersonal skills, with the ability to present data and recommendations to senior leadership
• Strong project management skills, with the ability to manage multiple complex tasks simultaneously
• Detail-oriented with strong problem-solving abilities and critical thinking skills
• Ability to handle confidential information with discretion and integrity

The Extras We Value (Preferred Requirements)

While not mandatory, here are some additional things that would make you stand out:

• Bachelor’s degree in Human Resources, Business Administration, or a related field
• Professional certifications such as CEBS (Certified Employee Benefit Specialist) or SHRM-CP/SHRM-SCP a plus
• A high degree of accuracy and attention to detail
• Intermediate to advanced level proficiency in Microsoft Excel
• Expert knowledge with benefits tools and HRIS systems (e.g., ADP)
• Detailed knowledge of benefits laws and regulations
• Excellent Oral and Written communication skills
• Expert knowledge and skills in using PowerPoint for presentations

Physical Requirements

We want to make sure you’re fully equipped for success. Here’s a look at any physical requirements nee