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.

Truck Driver/Laborer

Company: Tuscany Construction

Location: Addison, IL

Posted Aug 04, 2025

Valid driver’s license and ability to drive company stake bed truck. Ability to travel to out of state job location preferred. Ability to lift 50-60 lbs.

Consumer Promotions Senior Analyst

Company: Kimberly-Clark

Location: Chicago, IL

Posted Aug 04, 2025

While technical proficiency is essential—particularly in Power BI—you’ll also need to be a clear communicator who can distill complex data into accessible…

Independent Contractor Roofer

Company: Green Attic Insulation

Location: Mount Prospect, IL

Posted Aug 04, 2025

The ideal candidates will have extensive experience in installing metal, shingle, and various other roofing materials, along with an OSHA 30 certification.

Customer Service Representative - 5NE Surgical Services (Evenings)

Company: University of Illinois

Location: Chicago, IL

Posted Aug 04, 2025

Under general supervision, performs complex customer service functions, day to day document verification and revision, automated and manual/electronic data…

Retail Sales Associate, Evergreen Plaza - Flex

Company: Macy’s

Location: Evergreen Park, IL

Posted Aug 04, 2025

Frequent use of computers and other technology, necessary to perform job functions, including handheld equipment, cash register and ability to process register…

Welder II/pressure valves

Company: Midland Manufacturing, OPW, a Dover Company

Location: Skokie, IL

Posted Aug 04, 2025

Benefits: Our total rewards package for eligible team members also includes: a 401(k) savings plan with employer contributions; medical, dental and vision…

Data Quality Analyst

Company: Northern Trust Corp.

Location: Chicago, IL

Posted Aug 04, 2025

Ability to develop data quality controls (using SQL or a similar programming language), and establish reporting processes via Scheduling tools like Control M.

Market Research Analyst, Online Communities

Company: Ipsos

Location: Chicago, IL

Posted Aug 04, 2025

Work with the client and account team to develop and implement a successful community strategy incorporating engagement, content and communications.

ELECTRICAL CONSTRUCTION PROJECT MANAGER

Company: GPac

Location: Chicago, IL

Posted Aug 04, 2025

Journeyman or Master Electrician license is a plus, but not required. Coordinate field teams to ensure timely and safe execution of work.

Armed Armored Car Guard & Driver

Company: Ferrari Express, Inc.

Location: Schiller Park, IL

Posted Aug 04, 2025

Must have a valid *Illinois Driver’s License* with a clean driving record. Completion of 20-hour state-approved armed guard training (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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