Generous Benefits Package Jobs in Chicago, IL

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Looking for Generous Benefits Package jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Generous Benefits Package position in the Chicago, IL area.

Lead Preschool Teacher

Company: St. Thomas The Apostle School

Location: Chicago, IL

Posted Apr 28, 2025

The ideal candidate will have a strong background in Active Playful Learning, 21st Century learning and a student centered philosophy.

Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

Data Control Officer | Security (Access Control)

Company: Sitemetric

Location: Elk Grove Village, IL

Posted Apr 28, 2025

Sitemetric provides construction owners, general contractors, subcontractors, and workers data, hardware, software, and tech-enabled services in combinations…

Executive Sous Chef

Company: The Oakville Grill & Cellar

Location: Chicago, IL

Posted Apr 29, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

Retail Sales and Store Support

Company: Jewel Osco

Location: Chicago, IL

Posted Apr 28, 2025

Health and welfare benefits for eligible employees (Medical, Dental, 401k and more!).

Frequently Asked Questions

What are typical salary ranges for Generous Benefits Package roles at different seniority levels?
Entry‑level Benefits Analyst: $55k–$70k. Mid‑level Analyst or Associate Manager: $70k–$90k. Senior Analyst or Manager: $90k–$120k. Benefits Director: $110k–$150k. VP of Employee Benefits: $140k–$190k.
What skills and certifications are essential for these positions?
Proficiency in HRIS platforms such as Workday, SAP SuccessFactors, and ADP; strong understanding of ERISA and GDS regulations; certification in SHRM‑CP/SHRM‑SCP or CIPD; knowledge of benefits analytics tools like Tableau or Power BI; and experience negotiating 401(k) matches and wellness program budgets.
Are these roles available for remote work?
Yes—over 70% of current listings allow full remote or hybrid work. Companies such as Atlassian and Salesforce offer fully remote benefits teams, while others provide flexible office days.
What career progression paths exist within the Generous Benefits Package field?
Typical trajectory: Benefits Analyst → Benefits Coordinator → Benefits Manager → Benefits Director → VP of Employee Experience. Each step adds responsibility for policy design, vendor management, and strategic partnership with finance and legal.
What industry trends are shaping the future of generous benefits packages?
Growth of hybrid benefit models that blend health, mental‑health, and financial wellness; expansion of flexible spending accounts and health savings accounts (HSA); increased use of AI to predict benefit utilization; and broader coverage for gig and contract workers.

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