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.

InfoSec Compliance Analyst #Hybrid

Company: Alliant Credit Union

Location: Chicago, IL

Posted Jun 07, 2025

Facilitate IT issue management by work with employees on scheduling calls and going over the issue and resolution. Work from home up to 3 days a week.

Principal Technology Architect - MFG

Company: Infosys

Location: Chicago, IL

Posted Jun 07, 2025

You will identify technology big bets, develop solution propositions around them, do solution prototypes and proactively take it to the market.

Research Chef

Company: LifeSpice Ingredients

Location: Chicago, IL

Posted Jun 07, 2025

Work with flavor companies and other suppliers to identify or develop new raw materials. Culinary degree from accredited Culinary School.

Multi-Location Retail Inventory Associate

Company: Room & Board

Location: Chicago, IL

Posted Jun 07, 2025

Maintain welcoming stock room environments that are safe, organized, efficient and support the selling teams and the customer experience.

Senior Living Sales and Marketing Director

Company: Andersonville Supportive Living

Location: Chicago, IL

Posted Jun 09, 2025

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

Cloud Architect

Company: Fortune Brands

Location: Deerfield, IL

Posted Jun 09, 2025

Cloud Architecture & Strategy: Design, develop, and implement scalable and secure PaaS-based cloud architectures, primarily in Microsoft Azure, with a focus on…

Special Education Teacher

Company: Parkland Preparatory Academy

Location: Oak Lawn, IL

Posted Jun 09, 2025

Teachers work to design instructional opportunities for students to access state learning standards, achieve IEP goals, BIP goals and transition goals.

Electrician

Company: RWS Global

Location: Chicago, IL

Posted Jun 07, 2025

Valid driver’s license required. Preferred: Vocational or technical training – Field of Study: welding, engineering, rigging, carpentry, electronics, audio,…

Tax Senior - Financial Services Organization - State and Local Tax - Real Estate

Company: EY

Location: Chicago, IL

Posted Jun 08, 2025

A CPA certification, or good standing as a member of a state bar. Staying abreast of state & local tax developments and work to develop new and innovative…

Design Manager

Company: Avant Communications LLC

Location: Chicago, IL

Posted Jun 09, 2025

Chicagoland based, this role will oversee three designers that work across digital, print, events and video, and will also serve as an individual contributor in…

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.

Related Pages