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.

Database Developer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

Web Engineer - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 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…

CNC Supervisor / Lead Manager

Company: Swingmaster Corporation

Location: Franklin Park, IL

Posted Apr 17, 2025

High school diploma or GED required; associate degree or technical certification in machining/manufacturing preferred.

Full Stack Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 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…

Business Diversity Analyst

Company: Chicago Public Schools

Location: Chicago, IL

Posted Apr 17, 2025

Bachelor’s degree in Business Administration, Finance, Information Technology, or a related field of study from an accredited college or university.

Senior Data Engineer / Analytic Engineer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

As a Senior Data Engineer / Analytic Engineer (Microsoft Fabric), you will lead the design, implementation, and optimization of data engineering pipelines and…

Back End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 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…

Front-End Developer- AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 17, 2025

A bachelor’s degree (completed or in progress). Proficiency in at least one of the following programming languages or frameworks: JavaScript, TypeScript, Python…

Flooring Field Supervisor

Company: Performers Flooring & Design Gallery

Location: Bloomingdale, IL

Posted Apr 16, 2025

A field supervisor is responsible for the overall safety and productivity of the crew working under him. *Minimum 3 years of field experience*.

Director of Sales and Marketing | St Johns Resort Plymouth Michigan

Company: Schulte Hospitality Group

Location: Chicago, IL

Posted Apr 16, 2025

Strong understanding of digital marketing tools and platforms, including social media, SEO, PPC, and email marketing. About Saint John's Resort *.

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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