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.

Public Safety Officer

Company: Saint Mary of Nazareth Hospital

Location: Chicago, IL

Posted Aug 19, 2025

State Driver’s license upon hire. Experience in Healthcare security or related field preferred. Coordinates facility response to various potential problems for…

Product Analyst

Company: CI Financial Corp.

Location: Chicago, IL

Posted Aug 19, 2025

Demonstrated expertise and certifications in Salesforce or willingness to obtain administrator/consultative certification within 90 days.

Marketing Operations Analyst

Company: Culture Amp

Location: Chicago, IL

Posted Aug 18, 2025

Troubleshoot sync issues, configure API connections, manage field mapping, and collaborate with cross-functional teams to ensure tools work together effectively…

Seasonal Call Center Representative

Company: SURESTAFF LLC

Location: Bolingbrook, IL

Posted Aug 18, 2025

The Seasonal Call Center Representative provides customer-centric assistance via phone calls, email, or live chat interactions.

Temporary Online Program Manager

Company: The University of Chicago

Location: Chicago, IL

Posted Aug 18, 2025

Coordinate and support all technical aspects of live Zoom sessions including scheduling, facilitation, breakout room management, and troubleshooting.

Truck Driver

Company: Atlas Toyota Material Handling, LLC

Location: Bedford Park, IL

Posted Aug 19, 2025

Hold a valid CDL-A license with a clean driving record. Experience and certification in the operation of forklifts and aerial lift equipment.

Director of Marketing & Events

Company: The University of Chicago

Location: Chicago, IL

Posted Aug 18, 2025

Experience developing and implementing integrated marketing strategies, including digital, print, and social media components.

Day Porter

Company: Clear Investment Group

Location: Chicago, IL

Posted Aug 18, 2025

Reporting major issues (plumbing leaks, electrical hazards, appliance failures) to the maintenance team. Knowledge of basic tools (screwdriver, pliers, plunger,…

Business Analyst II

Company: Elevance Health

Location: Chicago, IL

Posted Aug 19, 2025

BA/PO/PMO certification is a plus. Works with programming staff to ensure requirements will be incorporated into system design and testing.

Sous Chef

Company: Perry's Steakhouse and Grille

Location: Oak Brook, IL

Posted Aug 18, 2025

Responsible for accurate creation and presentation of all food items served to guests. Manage back of house labor, meeting Perry’s goals and guest requirements.

Sr Software Engineer – Frontend (Chicago, IL)

Company: HERE Technologies

Location: Chicago, IL

Posted Aug 19, 2025

Contribute to technical design and architecture discussions. Experience with state management libraries like NgRx or Redux.

IT Programmer

Company: WITRON Integrated Logistics, Inc

Location: Arlington Heights, IL

Posted Aug 18, 2025

Communication with clients in respected field and independent decision-making based on knowledge level. Demonstrated ability to communicate effectively with…

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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