Benefits Manager

Applied Systems•Chicago, IL
•Hybrid

About The Position

Applied is where insurance technology gets reinvented, and we build it fast. Our cloud software and AI-powered solutions reach thousands of agencies and brokers worldwide, setting the pace for what modern insurance can do. We’re looking for a Benefits Manager to join our People Team and lead the design and delivery of our benefits and wellness programs, along with the AI-enabled systems that keep them running smoothly.

Requirements

  • Bachelor’s degree in Human Resources, Communications, Information Systems, or a related field (or equivalent experience), plus 5–8 years of progressive experience in benefits administration, benefits program management, or HRIS/benefits technology
  • Proven project management experience leading cross-functional benefits initiatives end to end, from open enrollment to vendor implementations and system transitions
  • Hands-on experience testing and administering a benefits module within a major HRIS platform (UKG strongly preferred)
  • Working knowledge of federal and state benefit regulations, including ERISA, COBRA, HIPAA, FMLA, and ACA
  • Experience managing benefits communications programs and employee engagement initiatives

Nice To Haves

  • CEBS or CBP certification
  • Experience with M&A benefit integrations or similar system and program transitions
  • Familiarity with AI writing tools and an understanding of RPA and workflow automation concepts

Responsibilities

  • Implement and manage benefit and wellness programs aligned to our total rewards philosophy, including open enrollment, vendor implementations, and M&A benefit integrations
  • Create inclusive, AI-assisted benefits communications and resources that drive awareness, engagement, and utilization across the platforms employees use
  • Govern benefits technology, including the HRIS benefit module, enrollment platform, and carrier feeds, and help shape our automation roadmap and human-AI decision boundaries
  • Build analytics dashboards and share utilization data and benchmark insights that inform plan design, vendor selection, and budget decisions
  • Build strong relationships with benefit vendors, consultants, and administrators, and monitor regulatory changes that affect plan administration
  • Keep compliance documentation current and support ERISA activities, including 5500 preparation, plan document reviews, and discrimination testing

Benefits

  • Medical, Dental, and Vision Coverage
  • Holiday and Vacation Time
  • Health & Wellness Days
  • A Bonus Day for Your Birthday
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