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.

CDL-A Regional Truck Driver

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

HR Data Analyst, North America

Company: Aon Corporation

Location: Chicago, IL

Posted Aug 05, 2025

Aon offers a comprehensive package of benefits for full-time and regular part-time colleagues, including, but not limited to: a 401(k) savings plan with…

General Accountant

Company: Marriott International, Inc

Location: Chicago, IL

Posted Aug 05, 2025

Cumplir con las políticas y procedimientos de la compañía; asegurarse de que el uniforme y la apariencia personal sean pulcras y profesionales; mantener la…

CDL-A Truck Driver (Regional OTR): Comprehensive Benefits

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

Glass Project Manager

Company: MTH Industries

Location: Hillside, IL

Posted Aug 05, 2025

This role requires strong technical knowledge, organizational skills, and the ability to coordinate teams across design, procurement, fabrication, and field…

Janitor Non Union

Company: HABITAT COMPANY LLC

Location: Chicago, IL

Posted Aug 05, 2025

Full time maintenance or janitorial experience, or experience in related field. Conduct all business in accordance with The Habitat Company’s policies and…

Controller

Company: Creative Financial Staffing

Location: Chicago, IL

Posted Aug 05, 2025

Ensure compliance with all regulatory reporting requirements, including 990s, 1099s, state cost reports, and sales tax filings.

Regional CDL-A Driver: Home Weekly

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated that values our employees and drivers like family. At G&D, you’re in control.

General Accountant

Company: Marriott International, Inc

Location: Chicago, IL

Posted Aug 05, 2025

Speak with others using clear and professional language; prepare and review written documents accurately and completely; answer telephones using appropriate…

Customer Engineer III, Applied AI, Public Sector

Company: Google

Location: Chicago, IL

Posted Aug 05, 2025

Master's degree in Computer Science, Engineering, Mathematics, or a technical field. Identify and qualify business opportunities and key customer technical…

Regional Truck Driver: 100% No-Touch

Company: G&D Integrated

Location: Chicago, IL

Posted Aug 05, 2025

Company drivers earn up to $105,000 per year. G&D Integrated is now hiring Class A CDL Truck Drivers in the Joliet, IL area for *Regional OTR routes* that get…

LABORER AS ESTIMATOR

Company: City of Chicago

Location: Chicago, IL

Posted Aug 05, 2025

Staff will follow any and all required Employment/Hiring Plan provisions, federal, state and local laws, and Collective Bargaining Agreements when applicable.

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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