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.

Project Manager

Company: Sidley Austin LLP

Location: Chicago, IL

Posted Jul 11, 2025

Demonstrated knowledge and execution of project management practices, tools and methodologies, including an appropriate project management tool (Smartsheet,…

CDL-A Truck Driver - Regional OTR

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

Senior Manager, Software Engineering, Back End (Go/Python/Java, Node, Jenkins, AWS, DevOps)

Company: Capital One

Location: Chicago, IL

Posted Jul 11, 2025

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

culinary chef manager - Starbucks Reserve Kitchen

Company: Starbucks

Location: Chicago, IL

Posted Jul 11, 2025

Drive the implementation of company programs by developing action plans and directly motivate and instruct kitchen teams to implement and meet operational and…

Data Analyst - Insurance

Company: WAHVE

Location: Chicago, IL

Posted Jul 11, 2025

Compile and prepare data for customer analysis. *Experience* *working in a data analysis role in the insurance or financial services industry – *_*required*_.

Commercial HVAC Preventative Maintenance Technician

Company: BGIS

Location: Chicago, IL

Posted Jul 11, 2025

Subject to drug, background, and driver’s license checks. Maintaining the company service vehicle, tools, and inventory stock while adhering to company driving…

CDL-A Truck Driver - Regional OTR - Up to $105k/yr

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

CDL-A Truck Driver - Regional OTR - Comprehensive Benefits

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

IT Project Support Specialist (Remote - IL)

Company: Tanager, Inc.

Location: Chicago, IL

Posted Jul 11, 2025

May consider college degree in IT field in lieu of experience. This position involves direct communication and support to ensure readiness to cut over remote…

CDL-A Truck Driver - Regional OTR - Home Weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Jul 11, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IN area for *Regional OTR routes* that get…

Maintenance Electrician - 1st and 2nd Shift

Company: JobSquad Staffing Solutions

Location: Chicago, IL

Posted Jul 10, 2025

Maintain, troubleshoot, and repair electrical and mechanical equipment, including motors, conveyors, PLCs, and control systems. Pay Rate: $40-$44 per hour.

Staff Product Security Engineer - AI

Company: Match Group

Location: Chicago, IL

Posted Jul 11, 2025

Experience with various prompt engineering techniques and AI models to effectively develop tooling. Bachelor’s Degree in Computing Science or related field.

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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