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.

Flat Roofing Foreman in the Chicago Area

Company: EverSeal Roofing

Location: Chicago, IL

Posted Jul 10, 2025

2–3 years’ experience in construction, roofing, or a skilled trade. If you’ve got at least *2 years of team leadership experience* and a background in…

Installer/Plumber

Company: Legendary Service

Location: Chicago, IL

Posted Jul 10, 2025

Valid driver's license with a clean driving record. Clearly explain diagnoses and repair or installation options to customers in a professional, polite manner.

Welder (TIG) 2d Shift

Company: Hydro, Inc.

Location: Chicago, IL

Posted Jul 10, 2025

Welding certification in 6g, a plus. You will be responsible for setting up and operating a variety of welding equipment, including an electric-welding…

Accounts Payable Accountant - RAIL

Company: First Citizens Bank.

Location: Chicago, IL

Posted Jul 10, 2025

The Accounts Payable Accountant role is responsible for Processing invoices, checks and wires for payments in accordance with Accounts Payable policies and…

Entry Level Sales Associate

Company: Customer Sales Representative

Location: Burr Ridge, IL

Posted Jul 10, 2025

Learn and implement sales scripts, client product information, and promotional strategies. Track and achieve weekly and monthly sales goals.

Janitorial / Cleaning Crew / Porter

Company: Dunkin Donuts

Location: Skokie, IL

Posted Jul 10, 2025

Prior experience as janitor, janitorial crew, cleaning crew, crew member, team member, porter, handyman is helpful to the success at this job.

Cabinet Finisher (2 Plus Years Finishing Experience Required)

Company: Renew Medic Chicago

Location: Bensenville, IL

Posted Jul 10, 2025

Occasionally perform work in the field on job sites doing cleaning, touch-ups, precision repairs, painting, and re-finishing. Expected hours: 40 – 50 per week.

Customer Service Representative/Clerical

Company: Insurance Placement Solutions

Location: Riverside, IL

Posted Jul 10, 2025

Answer incoming phone calls and assist clients with policy-related inquiries. Provide support with daily clerical tasks such as organizing mail and data entry.

Project Manager - Civil

Company: F.H. Paschen

Location: Chicago, IL

Posted Jul 10, 2025

Knowledge of construction, design, cost reporting and cash flow management. Develop field quality assurance and quality control plan with Superintendent.

Project Manager - JOC

Company: F.H. Paschen

Location: Chicago, IL

Posted Jul 10, 2025

Knowledge of construction, design, cost reporting and cash flow management. Develop field quality assurance and quality control plan with Superintendent.

Master Plumber

Company: Leaf Home

Location: Chicago, IL

Posted Jul 10, 2025

Train, coach and develop installation employees and contractors both in the office and in the field. Must hold a valid driver's license.

Machinist II

Company: Dart Container

Location: Chicago, IL

Posted Jul 10, 2025

Ability to obtain and maintain powered industrial truck (PIT) license. Read blueprints, schematics, specifications, bills of material, and various technical…

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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