Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

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.

Design Director, New York or Chicago

Company: Omnicom Production

Location: Chicago, IL

Posted Mar 31, 2025

Portfolio that showcases brand consistency through design systems, detailed design, scaled campaigns across channels, OLV, banners, PDP and social-first…

Property Accountant

Company: ENCORE SENIOR LIVING

Location: Chicago, IL

Posted Mar 28, 2025

The successful candidate has a bachelors degree in accounting - minimum 3- 5 years full cycle accounting experience.

Fireproofer

Company: Southwest Coating Services

Location: Chicago, IL

Posted Mar 31, 2025

Reliable vehicle, valid driver's license and proof of insurance. 401K matching after 6 months of employment. Proof of citizenship or ability to work in the U.S.…

OBGYN Physician

Company: No Employer

Location: Chicago, Illinois

Posted Mar 30, 2025

Experienced Carpenter/tradesman

Company: Davies Home Services

Location: Park Ridge, IL

Posted Mar 29, 2025

Strong skills in restoration techniques, framing, construction, painting, siding installation, tile laying, drywall.

Sous Chef

Company: LSG Sky Chefs

Location: Des Plaines, IL

Posted Mar 28, 2025

Understand and demonstrate concepts of financial controls (ex: keep food cost within budget, control stock levels while being cost conscious, minimize waste).

Analyst, Client Service Representative- Transaction Banking

Company: MUFG Bank, Ltd.

Location: Chicago, IL

Posted Apr 01, 2025

Further a culture of risk and compliance discipline, which includes, but is not limited to, maintaining compliance with Bank and business process-related…

Commercial Floor Coating Installer

Company: Southwest Coating Services

Location: Bridgeview, IL

Posted Mar 31, 2025

Reliable vehicle, valid driver's license and proof of insurance. The ideal candidate will have experience in concrete floor restoration, concrete repair and…

Senior Account Executive - Plumbing

Company: The Hill Group

Location: Franklin Park, IL

Posted Apr 01, 2025

Make warm calls to develop leads for all functions of The Hill Group. Attend monthly sales meetings with information on active leads being pursued, current…

Senior Specialist - Business Analysis

Company: LTIMindtree

Location: Chicago, IL

Posted Apr 01, 2025

Perform detailed analysis of user stories Connect and come in agreement with involved partner systems regarding various mapping documents and communication…

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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