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.

Information Security Analyst (Hybrid, Greater Chicago Area)

Company: Byline Bank.

Location: Chicago, IL

Posted Aug 13, 2025

Participates in risk assessments to identify and assess security risks of new, existing, or proposed infrastructure.

Armed Mobile Patrol (Position Located in Northwest Suburbs)

Company: Advanced Security Solutions Inc.

Location: Chicago, IL

Posted Aug 13, 2025

Must have a valid driver's license. Work in various environments including adverse outdoor conditions such as cold, rain or heat; Constant mental alertness and…

Marketing Manager

Company: Confidential

Location: Chicago, IL

Posted Aug 13, 2025

Education: Bachelor's degree in Marketing or a related field, MBA or masters within the applicable field or tenor experience preferred.

Residential High Rise Association - Helper A Janitor & Maintenance (Uptown)

Company: The Building Group

Location: Chicago, IL

Posted Aug 13, 2025

To perform repairs to common areas including HVAC, plumbing, electrical, and carpentry components, and other items as required. Ability to lift 50 lbs.

Banquet Chef

Company: Rivers Casino Des Plaines

Location: Des Plaines, IL

Posted Aug 13, 2025

Ensures that all guests are treated in a prompt, professional and courteous manner. Accredited degree or certification in culinary arts, hospitality, or…

Janitor / Laborer for Retirement Facility

Company: Retirement & Assisted Living Facility

Location: Northlake, IL

Posted Aug 13, 2025

Duties will include but not limited to: Prepare rooms for new move-ins; Patch dry wall & painting of various parts in building; Pull and install carpet and…

Armed Security Officer 2nd & 3rd Shift (Niles, IL)

Company: Advanced Security Solutions Inc.

Location: Niles, IL

Posted Aug 13, 2025

Must have a valid driver's license. Work in various environments including adverse outdoor conditions such as cold, rain or heat; Constant mental alertness and…

Armed Security Officer 1st, 2nd & 3rd Shifts

Company: Advanced Security Solutions Inc.

Location: Skokie, IL

Posted Aug 13, 2025

Must have a valid driver's license. Work in various environments including adverse outdoor conditions such as cold, rain or heat; Constant mental alertness and…

Director, Data Science - Model Risk

Company: Capital One

Location: Chicago, IL

Posted Aug 13, 2025

A PhD in a quantitative field (Statistics, Economics, Operations Research, Analytics, Mathematics, Computer Science, or a related quantitative field) plus 4…

Welder

Company: Sureway Group, Inc.

Location: Franklin Park, IL

Posted Aug 13, 2025

Ability to read and interpret technical drawings and specifications. The Welder will work with different materials and tools, contributing to the production of…

Customer Care Coordinator

Company: Residential Real Estate Council

Location: Chicago, IL

Posted Aug 13, 2025

Engage in member recruitment and retention efforts, including proactive outreach via phone calls, emails and social media. Become part of our dynamic team...

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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