Competitive Benefits Jobs in Chicago, IL

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Looking for Competitive Benefits jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Competitive 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…

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).

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…

Power BI Developer

Company: Velvetech

Location: Chicago, IL

Posted Apr 18, 2025

Design, develop and support data analytics using Power BI service, self-service models, and visualization tools. Experience with differen large language models.

Frequently Asked Questions

What are typical salary ranges for Competitive Benefits positions by seniority?
Entry‑level Benefits Analyst: $55k–$70k; Mid‑level Analyst or Manager: $70k–$90k; Senior Analyst/Benefits Manager: $90k–$120k; Director of Benefits: $120k–$160k; VP of Total Rewards: $160k–$220k. These figures are based on 2024 Glassdoor data and internal benchmarks from large tech firms.
What skills and certifications are required for a career in Competitive Benefits?
Core skills: benefits strategy, actuarial modeling, vendor negotiations, compliance with ACA/COBRA/HIPAA, data analysis (Excel, SQL, Tableau), and HRIS proficiency (BambooHR, Workday, ADP). Certifications: Certified Employee Benefit Specialist (CEBS), Compensation & Benefits Professional (C&BPS), Certified Compensation Professional (CCP), and HRIS certifications from SAP SuccessFactors or Workday.
Is remote work possible in Competitive Benefits roles?
Yes—most companies support hybrid or fully remote arrangements. Cloud‑based benefits portals, Slack, Microsoft Teams, and Zoom enable real‑time collaboration. Firms like Deloitte, Accenture, and tech startups routinely offer flexible options.
What career progression paths exist within Competitive Benefits?
Typical progression: Analyst → Manager → Director → VP of Total Rewards. Lateral moves can lead to HRIS leadership, data science in benefits analytics, or consulting. Experienced professionals may launch boutique benefits‑consulting firms or partner with HR tech vendors.
What industry trends are shaping Competitive Benefits today?
Key trends: AI‑driven benefits personalization; real‑time wellness dashboards; expansion of gig‑worker coverage; regulatory updates from the Omnibus Act; and heightened data‑privacy compliance. Tools like Workday Adaptive Insights, SAP SuccessFactors, and Gainsight are increasingly integrated to support these innovations.

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