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.

Analyst

Company: Paul Hastings

Location: Chicago, IL

Posted Aug 20, 2025

Able to clearly document and communicate technical information to both technical and non-technical users; and. Understanding of SailPoint and Oka;

Member Services Representative

Company: Rewards Network

Location: Chicago, IL

Posted Aug 20, 2025

Answer and respond to high-volume inbound calls and emails from Rewards Network members daily; assist with account questions and provide information related to…

Sales and Marketing Director

Company: Vantage Senior Care

Location: Lincolnwood, IL

Posted Aug 20, 2025

A. Create and maintain a solid referral base by developing a sustaining relationship with social workers, case managers, and key referral sources.

4124 ORD -Journeyman Electrician - FT

Company: ERMC

Location: Chicago, IL

Posted Aug 20, 2025

Maintenance and repair of all electrical, mechanical, and control devices, equipment, and components associated with the airport conveyor system.

CNC Lathe Setup/Operator

Company: WaterSaver Faucet Co.

Location: Chicago, IL

Posted Aug 20, 2025

Ability to change, touch-off, and indicate tools for CNC lathes or mills. Ability to read and comprehend blueprints (including GD&T features such as true…

Data and AI Architect

Company: Sargent & Lundy

Location: Chicago, IL

Posted Aug 20, 2025

Evaluate, design, and implement comprehensive automation strategies across Sargent & Lundy’s Data and AI/ML platforms, driving continuous improvement in…

Insulation Sales Consultant

Company: Perma-Seal Basement Systems

Location: Burr Ridge, IL

Posted Aug 21, 2025

Maintain a valid driver license to travel to our customers’ home for scheduled appointments. Explain financing options to clients and collect payments and…

Mold Machine Operator

Company: S & C Electric Company

Location: Chicago, IL

Posted Aug 20, 2025

You will frequently use hand and power tools such as knives, scrapers, engravers and air-impact tools. Use hand tools like files, hammer, scrapper, air nozzle…

Plan-to-Fulfill Reporting & Analytics Analyst

Company: Wm. Wrigley Jr.

Location: Chicago, IL

Posted Aug 21, 2025

Partner with technical teams to align data model objects with appropriate technical objects in SAP. Bachelor's degree in a relevant business function or…

CNC Machine Operator (2nd Shift)

Company: WaterSaver Faucet Co.

Location: Chicago, IL

Posted Aug 20, 2025

Ability to handle all basic CNC machining operations including changing inserts, touching off tools and making offsets. Perform tool and insert changes.

Mobile Security Patrol officer

Company: Per Mar Security Services

Location: Oak Brook, IL

Posted Aug 20, 2025

Must have personal own vehicle! . The selected individual will patrol and secure assigned premises as well as identify risks to staff and patrons.

CNC Mill Operator

Company: Upper Deck Staffing Pro

Location: Elk Grove Village, IL

Posted Aug 20, 2025

Read and interpret blueprints and technical drawings. Proficiency in using precision measuring tools. Assist in the mechanical assembly department when required…

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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