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.

Regional CDL-A Truck Driver, 66+ CPM

Company: Dollar General

Location: Chicago, IL

Posted Jul 23, 2025

1+ years CDL A driving experience. Must be 21 years of age. Experience preferred, requirement based on location. Short term and long term disability.

Client Service Representative

Company: LR WINDSOR Inc

Location: Chicago, IL

Posted Jul 22, 2025

State insurance license (Property & Casualty or Life & Health) must be obtained prior to start date. Previous experience in insurance, customer service, or a…

Plumber

Company: VanDerBosch Plumbing

Location: Chicago, IL

Posted Jul 22, 2025

Must have a valid driver’s license and a clean driving record. Your field experience with current plumbing license and certifications.

Senior Manager, Software Engineer

Company: Capital One

Location: Chicago, IL

Posted Jul 23, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

Program Manager HCM (Dayforce)

Company: CAI

Location: Chicago, IL

Posted Jul 22, 2025

Monitor project progress, identify potential risks, and implement mitigation strategies to minimize business disruption.

Substation Electrician

Company: Metra

Location: Chicago, IL

Posted Jul 23, 2025

Must have a valid driver's license. Starting pay rates may vary based on entry rates in the Collective Bargaining Agreement (CBA). High School Diploma or GED.

Customer Service Representative

Company: Demetrius Barbee Insurance Agency Inc

Location: Chicago, IL

Posted Jul 23, 2025

Assist clients with new quotes, updating policies, payments, and other services. You will respond promptly to inquiries, maintain accurate records, and…

Financial Control Accountant - Chicago, IL

Company: ADM

Location: Chicago, IL

Posted Jul 22, 2025

Financial wellness – flexible spending accounts, health savings account, 401(k) with matching contributions and cash balance plan, discounted employee stock…

Controller - Chicago, IL - Part-Time

Company: Your Part-Time Controller, LLC

Location: Chicago, IL

Posted Jul 23, 2025

4 WEEKS PAID TIME OFF, generally consisting of 100 hours paid vacation to start with eligibility for additional vacation based on tenure and a minimum 40 hours…

Sales Associate

Company: Levy Sector

Location: Chicago, IL

Posted Jul 23, 2025

Associates may also be eligible for paid and/or unpaid time off benefits in accordance with applicable federal, state, and local laws.

Night Custodian

Company: Community Consolidated School District 64

Location: Park Ridge, IL

Posted Jul 22, 2025

40 hours a week - 3 pm - 11:30 pm. Full benefits offered - see attached. Starting Hourly Rate - $22.35 an hour. 25-26 Medical Plan Comp Chart.pdf.

Project Manager II - Multifamily Projects

Company: Michael Page

Location: Chicago, IL

Posted Jul 23, 2025

Ability to hire, train, develop and manage a team of Project Managers by providing intentional and proactive leadership. Travel to job site 1-2 days a week.

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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