Generous Paid Time Off Jobs in Chicago, IL

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Looking for Generous Paid Time Off jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Generous Paid Time Off position in the Chicago, IL area.

Graphic Designer & Production Staff (Hourly, Bilingual)

Company: Jamali Kopy Kat Printing

Location: Bellwood, IL

Posted Aug 11, 2025

 Deliver finished print jobs to clients (must have valid driver’s license and clean.  Valid driver’s license and reliable transportation (for deliveries).

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2nd shift MIG Welder

Company: PROMAN

Location: Lombard, IL

Posted Aug 11, 2025

Utilize hand tools, power tools, and welding equipment for fabrication tasks. Read and interpret blueprints, schematics, and technical drawings to determine…

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Security Officer (Pt)

Company: City Colleges of Chicago

Location: Chicago, IL

Posted Aug 11, 2025

Must have a valid driver’s license, current CPR and/or first aid certification, and hazardous material training. Ability to lift and carry up to 50 pounds.

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Experienced Extruder Machine Operator

Company: Midwest Canvas Corp.

Location: Chicago, IL

Posted Aug 11, 2025

Proven experience in plastics extrusion or related manufacturing processes is preferred. Conduct quality inspections throughout the production process.

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Graphic Designer

Company: Kemper

Location: Chicago, IL

Posted Aug 11, 2025

This position will focus on applying best practices in user-centered design and production across various types of print and digital sales collateral.

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Lead Finish Carpenter / Architectural Plans Expert

Company: Arkwright Construction

Location: Chicago, IL

Posted Aug 11, 2025

Valid driver's license and dependable transportation. Experience managing subcontractors and directing field crews. Tech Package (Smartphone or Tablet).

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IT Cybersecurity Analyst

Company: American College of Surgeons

Location: Chicago, IL

Posted Aug 11, 2025

Resolve technical issues as they arise, develop and implement plans to reduce the recurrence/incidence of issues. Dental, Vision, and Prescription drug program.

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Project Manager - HYBRID (Warehouse/Mfg Automation exp req $140K)

Company: #twiceasnice Recruiting

Location: Chicago, IL

Posted Aug 11, 2025

Lead end-to-end delivery of warehouse automation projects, from design to implementation. Technical/automation solutions implementation: 3 years (Required).

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CDL A Truck Driver (Dry Van Freight)

Company: Roehl Transport

Location: Chicago, IL

Posted Aug 11, 2025

Class A drivers with at least four (4) months of recent driving experience. Top 50% of drivers average $1,330/week. *Home weekly* – typically for 48 hours.

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Manager, Marketing Operations

Company: FTI Consulting, Inc.

Location: Chicago, IL

Posted Aug 11, 2025

Partner with creative leads to implement strategic improvements to enhance efficiency. Technical Skills: Proficiency with project management tools (e.g.,…

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Cabinet Assembler/Cabinet Maker/Carpenter

Company: Factory Plaza

Location: Bensenville, IL

Posted Aug 11, 2025

Must know how to use saws, drills, and power tools. Kitchen cabinets factory in Bensenville. Hardworking individuals who are on time and trustworthy.

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Executive Chef- NEW RESTAURANT OPENING!

Company: Gibsons Restaurant Group- NEW RESTAURANT OPENING!

Location: Chicago, IL

Posted Aug 11, 2025

Hire, train, supervise, and develop kitchen staff. Ensure all kitchen and food operations are in compliance with all legislated health and licensing guidelines;…

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Frequently Asked Questions

What are the typical salary ranges for Generous PTO roles by seniority?
Entry‑Level PTO Analyst: $55k–$70k; Mid‑Level PTO Manager: $80k–$110k; Senior PTO Director: $130k–$170k. These ranges vary by region and company size.
Which skills and certifications are required for Generous PTO positions?
Core skills: PTO policy design, HRIS configuration (Workday, SAP SuccessFactors), data analytics (SQL, Excel, Power BI), compliance knowledge (FERPA, GDPR). Certifications: SHRM‑CP/SHRM‑SCP, HRIS Certified Professional, Workday HCM Certification, SAP SuccessFactors HCM Certification.
Is remote work available for Generous PTO roles?
Approximately 70% of PTO analyst and benefits coordinator positions allow full‑time remote or hybrid work, especially in SaaS and tech firms. On‑site roles exist for compliance audit positions that require physical access to employee records.
What are the career progression paths in Generous PTO roles?
PTO Analyst → PTO Manager → PTO Director → HR Director / VP of People Experience → Chief People Officer. Each step expands strategic influence from policy design to workforce planning.
What are the current industry trends for Generous PTO?
AI‑driven leave analytics, continuous PTO policies, integration of mental‑health metrics, global time‑zone‑aware accrual systems, emphasis on employee well‑being dashboards. Companies are adopting flexible PTO models to attract and retain talent.

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