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.

Service Technician/Machinist

Company: Goulds Pumps IPG LLC

Location: Chicago, IL

Posted Sep 01, 2025

Building on centuries of pump design experience, PRO Services provides an array of services focuses on reducing equipment total cost of ownership and increasing…

Customer Service & Sale Representative

Company: GLOBAL TALENT NEXUS

Location: Lombard, IL

Posted Aug 31, 2025

Tech-savvy with the ability to use CRM tools and reporting systems. Proactively manage assigned customer accounts and track progress toward retention goals.

Tool Room Machinist 1st shift)

Company: Klein Tools

Location: Elk Grove Village, IL

Posted Sep 01, 2025

Fits and assembles parts into complete assembly, using jigs, fixtures, surface plates, surface table, hand tools and power tools. Ability to weld is a plus.

Customer Success Supervisor

Company: KO Business Solutions

Location: Elk Grove Village, IL

Posted Aug 31, 2025

High school diploma required; Bachelor’s degree in business or related field preferred. Familiarity with CRM systems and reporting tools.

Lease Purchase Truck Driver

Company: Risinger Brothers Transfer, Inc.

Location: Chicago, IL

Posted Sep 01, 2025

If you pride yourself in being a professional & safe Class-A Truck Driver, you can lease purchase well maintained 2020-2025 Volvo trucks for no money down and…

CDLA Local Truck Drivers

Company: Calhoun Truck Lines

Location: Chicago, IL

Posted Sep 01, 2025

HOURLY PAY - $24 -$34 (Overtime after 40 hours) LOCAL RUNS - HOME DAILY! Weekends optional STEADY & STABLE WORK!

Sales and Merchandising Specialist

Company: SAS Retail Services

Location: Chicago, IL

Posted Sep 01, 2025

Have a valid driver’s license. You’re great at building relationships with store management, calling on customers and love the autonomy of managing your own…

Extra Help - Customer Service Representative - Hospital Neonatal Nursing

Company: University of Illinois

Location: Chicago, IL

Posted Sep 01, 2025

This includes greeting patients, answering/routing telephone calls, ordering supplies and other administrative/customer service duties.

Maintenance Electrician - Days B

Company: Sherwin-Williams

Location: Chicago, IL

Posted Sep 01, 2025

Have at least an industrial, electrical, and/or welding certifications or license. Understands basic electrical and pneumatic diagrams, familiar with 12 VDC to…

CDL-A Owner Operator Local Intermodal Home Daily

Company: PB Industries, Inc

Location: Elk Grove Village, IL

Posted Sep 01, 2025

(1099 Contractors are responsible for their own health, dental, and vision insurance. 1099 Owner Operator truck drivers are also responsible for tax reporting.)…

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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