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.

Senior Manager, Corporate Affairs Operations

Company: Adtalem Global Education

Location: Chicago, IL

Posted Aug 04, 2025

PMP certification or equivalent project management credentials strongly preferred. Leadership skills with experience managing teams and driving organizational…

Senior Manager - Segment Communications

Company: Adtalem Global Education

Location: Chicago, IL

Posted Aug 04, 2025

7+ years of experience in communications, marketing, or related field. Proficiency in content management systems, analytics tools, and multimedia platforms.

Security Supervisor

Company: P4 Security Solutions

Location: Rogers Park, IL

Posted Aug 04, 2025

Customer service and front desk reception. The Off Duty or Retired Law Enforcement roles are ideal for those seeking flexible scheduling and premium…

Project Manager

Company: Engtal

Location: Chicago, IL

Posted Aug 04, 2025

Bachelor's degree in Construction Management, Engineering, or related field preferred (but not required based on experience).

Automation Support Engineer

Company: Retiina

Location: Forest Park, IL

Posted Aug 04, 2025

Repair and maintain systems in accordance with diagrams, sketches, operation manuals, and manufacturer’s specifications, machinery and mechanical equipment,…

Sales Associate, Holiday Seasonal, Lincoln Park- Williams Sonoma

Company: Williams-Sonoma, Inc.

Location: Chicago, IL

Posted Aug 04, 2025

Efficiently and accurately perform register transactions i.e. sales, returns, and exchanges. Assist in implementation and maintenance of visual merchandise…

Pallet Repair / Pallet Builder

Company: Schroeder's Pallet Service

Location: Bedford Park, IL

Posted Aug 04, 2025

In this position, you will support the warehouse operations by repairing pallets. The ideal candidate is a team player with experience building and repairing…

Accountant

Company: Cushman & Wakefield

Location: Chicago, IL

Posted Aug 04, 2025

May be assigned to either accounts payable or receivable and may handle billing/invoicing, cash receipts, data entry, budgets and budgeting, expenses, sales…

Maintenance Employee

Company: De LaSalle Institute

Location: Chicago, IL

Posted Aug 04, 2025

Resource room and faculty dining room.  Responsible for the cleanliness of offices, classrooms, executive office washrooms, faculty.

Solutions Architect - Central US

Company: Infoblox

Location: Chicago, IL

Posted Aug 04, 2025

Collaborating closely with the field sales teams and our customers , you will help the sales team develop new business by working directly with customers and…

Janitorial Crew Member (Full-Time)

Company: Sertoma Star Services

Location: Chicago, IL

Posted Aug 04, 2025

To comply with state regulations ensuring the safety and well-being of the individuals we support, we require all potential employees to undergo a thorough…

Implementation Manager (Operations Engineering)

Company: NewCold

Location: Chicago, IL

Posted Aug 04, 2025

As the implementation manager, you will focus on managing the implementation of NewCold worksites to ensure they are delivered on time and within budget.

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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