Benefits Specialist

Phyton Talent Advisors
Chicago, IL

Benefits Specialist (Hybrid – Chicago, IL)


We’re looking for a detail-oriented and employee-focused Benefits Specialist to join our clients growing financial services firm in a hybrid role based in Chicago, IL. In this role, you’ll help shape a seamless and supportive benefits experience for employees across the U.S. If you enjoy blending analytics with employee support and thrive in a fast-paced environment, this could be a great fit.


What You’ll Do

As a Benefits Specialist, you’ll play a key role in delivering and optimizing our benefits programs:

  • Administer and support U.S. employee benefits programs including health, welfare, retirement, and wellness offerings, while assisting with global benefits processes as needed
  • Serve as a primary point of contact for employee questions related to benefits and leave of absence (LOA), ensuring timely and accurate support
  • Coordinate end-to-end leave of absence processes, including eligibility review, documentation tracking, communications, and return-to-work planning
  • Facilitate benefits onboarding sessions for new hires and provide backup support for global orientation efforts
  • Manage vendor billing and reconciliation activities, ensuring accuracy and resolving discrepancies across benefit plans
  • Monitor compliance with applicable regulations (e.g., federal, state, and global requirements) and support ongoing audit activities
  • Analyze benefits data and trends to identify opportunities for cost optimization and enhanced employee experience
  • Build and maintain reporting dashboards and key metrics such as utilization, participation rates, and vendor performance
  • Support open enrollment cycles in the U.S. and contribute to global renewals and program rollouts
  • Assist with retirement plan processes, including annual testing and audit coordination
  • Identify process improvements and implement solutions to increase efficiency and accuracy in benefits administration


What You Bring

  • Bachelor’s degree in Human Resources, Business, Finance, or a related discipline
  • 2-5 years of experience supporting employee benefits programs and related analytics
  • Hands-on experience with U.S. benefits offerings and familiarity with vendor coordination
  • Working knowledge of compliance requirements such as FMLA, ERISA, HIPAA, ADA, and state leave laws
  • Experience with HRIS and benefits systems; exposure to Workday is a plus
  • Proficiency in Excel and comfort working with data and reporting tools
  • Excellent communication skills, with experience delivering presentations and employee-facing sessions
  • High attention to detail and ability to manage sensitive information with discretion
  • Strong organizational skills and the ability to manage multiple priorities


Why Join Us?

  • Hybrid work flexibility in Chicago
  • Opportunity to influence and improve employee benefits
  • Collaborative and fast-paced environment with room to grow
  • Meaningful work that directly impacts employee well-being and experience

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