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.

Customer Service Representative

Company: Lawson Products

Location: Chicago, IL

Posted Jul 14, 2025

Responds to a minimum of 40 calls per day in an inbound call center. Possesses entry-level problem solving kills. High School Diploma or GED.

Unarmed Security Officer #247

Company: Stark Security Inc

Location: Chicago, IL

Posted Jul 14, 2025

Make guests aware of rules that must be adhered to. Occasional – reaching, stooping, climbing, balancing, driving, bending, twisting, handling paperwork.

Senior Accountant/Bookkeeper

Company: STANLEY ZILBER & ASSOCIATES, PC

Location: Chicago, IL

Posted Jul 14, 2025

We are seeking a detail-oriented and experienced Senior Accountant/Bookkeeper. The ideal candidate will possess a strong background in Construction Accounting…

Copywriter HYBRID — FULL-TIMECHICAGO

Company: Edelman

Location: Chicago, IL

Posted Jul 14, 2025

High-level concepting, tactical program ideation and copywriting for a wide range of brand experiences, social content and marketing deliverables that generate…

Accountant

Company: Corporate Leadership Center, NFP

Location: Chicago, IL

Posted Jul 14, 2025

Assist with the annual audit, including preparing supporting information, answering questions and reviewing annual reports and Form 990.

Registered Nurse- FT/PT PM Shift Only!

Company: Pearl of Montclare

Location: Elmwood Park, IL

Posted Jul 14, 2025

Prepare & administer medications as ordered by the physician. Admit, transfer and discharge residents as required. Join The Pearl of Montclare!

Associate Manager, Investment, Search

Company: Rise

Location: Chicago, IL

Posted Jul 14, 2025

Collaborate with leadership and peers to develop solutions that will enhance our operational efficiency, tools, and systems, and improve current workflows.

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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