Thoughtfully Curated Benefits Jobs in Chicago, IL

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

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 for Thoughtfully Curated Benefits roles by seniority?
Entry‑level Benefits Analyst: $60k–$90k. Mid‑level Benefits Architect or Consultant: $90k–$130k. Senior roles such as Benefits Director or VP of Benefits: $130k–$200k. Ranges vary by company size, region, and the complexity of benefit programs managed.
What skills and certifications are required for these positions?
Core skills: benefits compliance (ERISA, COBRA), data analytics (Excel, SQL, Tableau), vendor management, and employee engagement. Certifications: Certified Employee Benefits Specialist (CEBS), Society for Human Resource Management – Benefits Credential (SHRM‑B), Certified Compensation Professional (CCP), and proficiency with platforms like Workday, SAP SuccessFactors, Zenefits, Gusto, or Benefitfocus.
Is remote work available for Thoughtfully Curated Benefits roles?
Yes. Most benefits analyst and consultant positions offer fully remote or hybrid arrangements. Companies use Slack, Microsoft Teams, and cloud‑based benefits portals to enable real‑time collaboration and remote onboarding.
What career progression paths exist in this field?
Typical progression: Benefits Analyst → Senior Analyst → Benefits Manager → Director of Benefits → Vice President of Benefits or Chief Benefits Officer. Alternatively, a consulting track may lead from Benefits Consultant → Senior Consultant → Benefits Partner → Managing Director.
What industry trends are shaping Thoughtfully Curated Benefits?
Key trends include: 1) AI‑driven benefits recommendation engines that tailor plans to individual employee profiles; 2) expansion of mental‑health and flexible‑spending accounts; 3) real‑time enrollment and usage analytics; 4) ESG‑aligned benefit strategies; and 5) increased emphasis on data privacy and compliance in benefits data management.

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