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.

CAD Program Manager

Company: The Container Store Inc.

Location: Elmhurst, IL

Posted Jul 12, 2025

Bachelor's degree in Engineering, Computer Science, or related field. 4-7 years of experience in CAD program management or related field.

Preschool Assistant Director River North

Company: Kido

Location: Chicago, IL

Posted Jul 12, 2025

Oversee curriculum implementation and ensure licensing compliance. CDA or Bachelor’s degree in Early Childhood or a related field.

Insurance Sales Agent - Customer Service

Company: Freeway Insurance Services America, LLC

Location: Berwyn, IL

Posted Jul 12, 2025

Personal Lines or Property and Casualty license preferred (but not required). Accurate accounting of all currency transactions as well as timely delivery of…

Public Safety Supervisor (Armed) 3rd Shift

Company: Advocate Aurora Health

Location: Chicago, IL

Posted Jul 12, 2025

A valid driver’s license issued by the Division of Motor Vehicle. Responsible for KRA results; provides input to and implements the budget, administers policies…

Flex Security Officer - Open Schedule

Company: Securitas

Location: McCook, IL

Posted Jul 12, 2025

Provide high level of customer service to clients, employees, and guests. Valid Driver's License and clear driving history. Prior security experience a plus.

Senior Brand Manager, Brand Growth & Innovation - Cottonelle®

Company: Kimberly-Clark

Location: Chicago, IL

Posted Jul 13, 2025

Lead portfolio technology mapping and cascade strategy, including business case ownership of big technical bets. Bachelors Degree in Business/Marketing.

Insurance Sales Agent - Customer Service

Company: Freeway Insurance Services America, LLC

Location: Addison, IL

Posted Jul 12, 2025

Personal Lines or Property and Casualty license preferred (but not required). Accurate accounting of all currency transactions as well as timely delivery of…

Welder 1/Fabrication

Company: Weiss-Aug – Elk Grove Village, IL

Location: Elk Grove Village, IL

Posted Jul 12, 2025

Minimum of 1 year of manufacturing experience. Give finished tank an inspection to ensure tank meets customer visual requirements, i.e. weld spatter removed,…

Executive Sous Chef | Full-Time | McCormick Place Convention Center

Company: Oak View Group

Location: Chicago, IL

Posted Jul 13, 2025

Continually manage, monitor and seek labor efficiencies to reduce costs, improve product output and enhance overall guest experience.

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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