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.

Residential Construction General Laborer

Company: Home by Molly Marino and CZ Construction Group

Location: La Grange, IL

Posted Aug 06, 2025

Reliable transportation and a valid driver’s license. Perform rough and finish carpentry including *framing, trim work, door installation, window installation…

Part Time Program Manager - Des Plaines School District

Company: Right At School

Location: Des Plaines, IL

Posted Aug 06, 2025

Coursework or training in child development and/or related field. Respond promptly to emails, text messages, and inquiries during program hours to ensure…

Residential Construction Foreman and Laborer

Company: Home by Molly Marino and CZ Construction Group

Location: La Grange, IL

Posted Aug 06, 2025

Reliable transportation and a valid driver’s license. Handle *light electrical and plumbing tasks* as needed. You’ll be expected to manage job sites, coordinate…

Cyber Security Analyst - Tier 3

Company: BigHire

Location: Hines, IL

Posted Aug 06, 2025

*Bachelor’s degree in computer science, Cybersecurity, Information Technology, or a related field (or equivalent work experience) – Must have.*.

Cleaning Technician / General Labor

Company: Stanley Steemer

Location: Chicago, IL

Posted Aug 06, 2025

Valid, US driver's license. These are field-based positions and require travel in and around the surrounding area. Power tools preferred, but will train.

Maintenance Electrician

Company: Ann & Robert H. Lurie Children’s Hospital of Chicago

Location: Chicago, IL

Posted Aug 06, 2025

Maintains a valid driver s license and safe driving record. Working knowledge of building and life safety codes with specific knowledge of city, state and…

Senior Concrete Finisher / Framer / Layout

Company: Ari Walsh

Location: Cicero, IL

Posted Aug 06, 2025

Valid DL with a good driving record. Ability to lift up to 50lbs and be comfortable working in outdoor environments/various weather conditions.

Sales Engineering Director - Modern Infrastructure

Company: Arrow Electronics, Inc.

Location: Itasca, IL

Posted Aug 06, 2025

This team of SEMs and sales engineers provide technical expertise through sales calls, presentations, solution design, product and proof of concept…

PAINTER

Company: Cook County Health & Hospitals System

Location: Chicago, IL

Posted Aug 06, 2025

A copy of a valid State ID Card or Driver’s License which identifies the holder of the ID as a Veteran, may also be attached to the application at time of…

Customer Brand Ambassador & Sales Associate

Company: Legacy Forward Solutions

Location: Elmhurst, IL

Posted Aug 06, 2025

Learn and maintain strong product knowledge to educate customers effectively. Execute brand promotions and in-store marketing strategies.

Experienced Commercial Painter

Company: Southwest Coating Services

Location: Chicago, IL

Posted Aug 06, 2025

Reliable vehicle, valid driver's license and proof of insurance. 401K matching after 6 months of employment. Wallcovering installation a plus, but not required.

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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