Great Benefits Jobs in Chicago, IL

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

Sales and Marketing Representative

Company: SERVPRO

Location: Broadview, IL

Posted Apr 18, 2025

In this role you will be meeting with potential customers to help develop our customer base and exceed sales goals via route selling, continuing education…

Data Analyst - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Apr 18, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

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…

Tax Senior - Financial Services Organization - State and Local Tax - Real Estate

Company: EY

Location: Chicago, IL

Posted Apr 20, 2025

A CPA certification, or good standing as a member of a state bar. Staying abreast of state & local tax developments and work to develop new and innovative…

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…

Tax Services Manager - FSO - GCR/Insurance EDGE

Company: EY

Location: Chicago, IL

Posted Apr 18, 2025

Direct experience in state and local taxation (e.g., state return compliance, state income tax accounting, state apportionment fundamentals).

Frequently Asked Questions

What are typical salary ranges by seniority in Great Benefits roles?
Entry‑level Benefits Analyst: $55k–$70k. Mid‑level Benefits Specialist: $70k–$90k. Senior Benefits Manager: $90k–$120k. Director of Benefits: $120k–$160k, depending on company size and region.
What skills and certifications are required for Great Benefits positions?
Core skills: proficiency in HCM systems like Workday, SAP SuccessFactors, or ADP; data analysis with Excel or Tableau; knowledge of ACA, COBRA, HIPAA; strong negotiation skills. Certifications: Certified Employee Benefits Advisor (CEBA), Certified Benefit Professional (CBP), SHRM‑CP or SHRM‑SCP, and specialization in benefits technology (e.g., Zenefits or Benefitfocus).
Is remote work available for Great Benefits roles?
Over 70% of Great Benefits roles support remote or hybrid arrangements. Companies such as Gusto, Benefitfocus, and Mercer offer fully remote positions, while larger firms may require occasional on‑site presence for carrier meetings.
What are common career progression paths in Great Benefits?
Typical path: Benefits Analyst → Benefits Specialist → Benefits Manager → Director of Benefits → VP of People & Benefits. Advancement often requires demonstrating carrier negotiation success, data‑driven program design, and leadership of cross‑functional initiatives.
What industry trends are shaping Great Benefits today?
Current trends include AI‑driven benefits analytics, increased focus on mental‑health and behavioral wellness, expansion of gig‑economy benefits packages, compliance with evolving data‑privacy laws, and integration of benefits platforms into unified HCM solutions.

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