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.

Electrician Journeyman - 90108690 - Chicago

Company: Amtrak

Location: Chicago, IL

Posted Aug 06, 2025

Experience in electrical repairs, and testing advanced electrical/electronic systems and reading, drafting, and interpreting circuit diagrams, schematics, and…

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401(k) dental insurance disability insurance

OBGYNs and Pediatricians needed

Company: Stratton Group LLC

Location: Chicago, Illinois

Posted Aug 06, 2025

View Details Apply on healthecareers.com

JANITOR III (DEPARTMENT OF FACILITIES MANAGEMENT) - SEIU 73 - VARIOUS LOCATIONS

Company: Cook County Offices Under the President

Location: Chicago, IL

Posted Aug 06, 2025

Candidates who are contacted will be required to produce original required documents (e.g., current driver’s license, diploma, school transcript, certifications…

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Facilities Maintenance Technician(WELDER)

Company: Central Transport

Location: Hillside, IL

Posted Aug 06, 2025

*Carpentry *– install floor tiles including ceramic and VCT, repair and hang metal/wood doors, masonry repairs, concrete repairs, drywall, and other trades.

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Client Engagement Associate Opening #485258

Company: Rose International

Location: Chicago, IL

Posted Aug 06, 2025

The second key focus is to develop new relationships with prospective clients. Excellent customer service skills and business etiquette.

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Public Safety Officer

Company: Jackson Park Hospital

Location: Chicago, IL

Posted Aug 06, 2025

Posted Date: 8/6/2025 Job Location: Chicago Position Type: Full-Time Division: Ancillary Services Description: Must have 20 Hours Unarmed Certificate PERC…

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CDL A Truck Driver - Pick Your Home Time

Company: K&B Transportation

Location: Chicago, IL

Posted Aug 06, 2025

We offer our OTR truck drivers one of the best health insurance policies in the industry. Road Warrior drivers earn $.70 CPM. 4 Weeks Out / 5 Days Off.

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Furniture Builder

Company: Comfy Living Chicago

Location: Chicago, IL

Posted Aug 06, 2025

You’ll be responsible for building wood frames and components for sofas and other furniture using nail/staple guns, saws, and hand tools.

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Executive Sous Chef

Company: Gibsons Italia

Location: Chicago, IL

Posted Aug 06, 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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Tax Consultant

Company: Recruiting Solutions

Location: Chicago, IL

Posted Aug 06, 2025

Our Tax Consultants work with our experienced professionals to develop and present personalized and comprehensive strategies to the businesses.

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full time academic be or bc

Pulmonary and Critical Care Medicine: Interventional Pulmonary Clinician-Educator

Company: Northwestern University

Location: Chicago, Illinois

Posted Aug 06, 2025

View Details Apply on healthecareers.com

AT&T Sales Associate

Company: Impact Management Solutions

Location: Chicago, IL

Posted Aug 06, 2025

You will be the face of AT&T’s brand, providing exceptional customer service and driving sales. Create a welcoming and friendly environment to attract and…

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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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