Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

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.

C# Engineer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

Global Practice Architect, Infrastructure III, Google Cloud

Company: Google

Location: Chicago, IL

Posted Aug 06, 2025

You will orchestrate across numerous contributing teams including solutions, services, partners, product engineering, marketing, and GTM stakeholder…

Pre-Certification & Call Center Representative

Company: VitalSkin Dermatology

Location: Chicago, IL

Posted Aug 06, 2025

You are able to perform all aspects of a call center: manage a high volume of incoming calls in a small, centralized call center; obtain information from the…

Staff Data Scientist

Company: The University of Chicago

Location: Chicago, IL

Posted Aug 05, 2025

Serving as a reference for staff, faculty members, and Gen3 users as technical subject matter expert by applying principles of data science to define and scope…

Python Developer

Company: BlackRock Investments

Location: Chicago, IL

Posted Aug 06, 2025

Participate in cross-functional feature requirements gathering, design, and implementation. You will collaborate with experienced engineers to develop and…

Data Scientist II, Condition Monitoring

Company: Caterpillar

Location: Chicago, IL

Posted Aug 06, 2025

In-depth technical and problem-solving skills and evidence of continuous learning in the analytics field. Programming Languages: Working knowledge of basic…

Project Manager II

Company: Gilbane Building Company

Location: Chicago, IL

Posted Aug 06, 2025

Participates in enrollment for insurance and bonds; tracks and obtains trade contractors’ compliance. Strong technical and communication skills are critical.

Custodial Worker/ Janitor

Company: Broadview Baptist Church

Location: Broadview, IL

Posted Aug 06, 2025

Adhere to established procedures to provide a safe working environment including complying with OSHA, state/local federal and City Wide regulations.

Dump Truck Driver

Company: Hana Transport Inc.

Location: Chicago, IL

Posted Aug 06, 2025

Valid commercial driver's license (CDL A) with, 3+ years experience in dump/must have a clean CDL License with no more than 2 tickets in the past 3-years.

Senior Project Accountant

Company: Rotary International

Location: Evanston, IL

Posted Aug 06, 2025

Bachelor’s degree in Accounting, Finance, or a related field (required). CPA or equivalent certification preferred. Proficient in accounting software and Excel.

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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