Comprehensive Benefits Jobs in Chicago, IL

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

Manager Contract Administrative Operations

Company: Health Care Service Corporation

Location: Chicago, IL

Posted Jun 13, 2025

J. D. degree or 4 years experience in a leadership role with independent decision-making. Manages the performance, overall quality and resource allocation to…

Licensed Plumber

Company: Tri-State Water, Power & Air

Location: Chicago, IL

Posted Jun 11, 2025

Respond promptly to emergency calls. Collaborate with contractors on new builds and renovations. All-Inclusive Support: Company truck, fuel, uniforms, tool…

Software Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Jun 11, 2025

You can work on your own schedule. A bachelor's degree (completed or in progress). You will work with the chatbots that we are building in order to measure…

Data Loss Prevention Analyst

Company: Sidley Austin LLP

Location: Chicago, IL

Posted Jun 13, 2025

This position is responsible for the ongoing design, implementation, monitoring, and refinement of the Firm’s DLP solutions. Able to work under pressure.

Bulk Tanker Driver - OTR

Company: Diversified Logistics

Location: Chicago, IL

Posted Jun 12, 2025

If you don’t have manual transmission experience, a tanker endorsement, a TWIC card, and at least 3 years of driving experience — this isn’t the job for you.

HVAC Technician

Company: Trane Technologies

Location: Willowbrook, IL

Posted Jun 12, 2025

Must possess a valid driver’s license for a minimum of 12 months, with no major or frequent traffic violations including, but not limited to:

HVAC Technician

Company: Trane Technologies

Location: Willowbrook, IL

Posted Jun 12, 2025

Must possess a valid driver’s license for a minimum of 12 months, with no major or frequent traffic violations including, but not limited to:

Graphic Designer

Company: Berglund Construction

Location: Westmont, IL

Posted Jun 11, 2025

Bachelor’s degree in graphic design, visual arts, or a related field. Develop engaging visual content for the company's website and social media platforms.

Senior Rails Engineer

Company: HAAS Alert

Location: Chicago, IL

Posted Jun 11, 2025

Collaborate with cross-functional teams to define, design, and ship new features. Strong understanding of software architecture, design patterns, and testing…

CDL A Regional Truck Driver

Company: Zeller Transportation

Location: Calumet City, IL

Posted Jun 12, 2025

Must have valid CDL-A license. If you’re ready to join a carrier that will fuel your career growth as a CDL-A truck driver, take a closer look at Zeller…

Lead Graphic Designer

Company: New Home Star

Location: Elmhurst, IL

Posted Jun 11, 2025

3–5 years of professional graphic design experience in an agency or in-house setting. Mentor, support, and guide Junior Graphic Designers in their technical and…

Traveling Project Superintendent

Company: International Contractors Inc.

Location: Oakbrook Terrace, IL

Posted Jun 11, 2025

Must have a valid driver’s license. Maintaining a safe work site by implementing good housekeeping regulations and safety requirements, enforcing safe work…

Frequently Asked Questions

What are the typical salary ranges for Comprehensive Benefits roles at different seniority levels?
Entry‑level Benefit Analyst: $55k–$75k; Mid‑level Analyst or Consultant: $75k–$95k; Senior Analyst or Manager: $95k–$130k; Director of Benefits: $130k–$170k; VP of Compensation & Benefits: $170k–$220k.
What skills and certifications are required for a career in Comprehensive Benefits?
Core skills: HRIS mastery (Workday, SAP SuccessFactors, Oracle HCM), SQL and Tableau for data analysis, vendor scorecard creation, compliance with ERISA, ACA, COBRA, and HIPAA. Certifications that add value: SHRM‑SCP, HRCI CRA, Certified Benefits Professional (CBP), Certified Employee Benefit Specialist (CEBS), and Gusto’s GDS credential.
Is remote work available for Comprehensive Benefits positions?
Yes. Tech firms such as Atlassian, GitHub, and Buffer offer fully remote and hybrid benefit teams. Remote roles require strong digital collaboration, familiarity with virtual HRIS environments, and self‑management of vendor relationships.
What career progression paths exist within Comprehensive Benefits?
Typical progression: Benefit Analyst → Lead Analyst → Benefit Manager → Benefits Director → Vice President of Compensation & Benefits. Each step adds responsibility for strategy, budgeting, cross‑functional leadership, and executive reporting.
What industry trends are shaping the future of Comprehensive Benefits?
Key trends include AI‑driven benefit personalization, expanded mental‑health and wellness programs, ESG‑aligned benefit packages, integration of health data analytics, and blockchain solutions for claims processing. Hybrid‑work models also drive new transportation and flexible‑time benefits.

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