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.

Assistant Project Manager - Light Industrial

Company: Michael Page

Location: Chicago, IL

Posted Oct 01, 2025

Review project implementation and gather data on project execution. Technical background with understanding of building engineering and commercial projects;…

Environmental Services Technician II - Evenings

Company: Endeavor Health

Location: Chicago, IL

Posted Sep 30, 2025

Performs daily and terminal cleaning, replenishes supplies and reports necessary repairs of all patient care and ancillary areas (including patient rooms,…

Chef Manager

Company: Belmont Village Oak Park

Location: Oak Park, IL

Posted Oct 01, 2025

You will select, train and grow culinary talent within our state-of-the-art kitchen and develop lasting relationships with residents and guests in our…

Investment Data Research Analyst

Company: Morningstar

Location: Chicago, IL

Posted Sep 30, 2025

Communicate data requests to data providers, including all necessary data templates and submission instructions and answering any questions.

Project Manager - Owners Rep

Company: CDO Group, Inc

Location: Oak Park, IL

Posted Oct 01, 2025

The primary role of a Project Manager is to carefully plan each phase of the project, create benchmarks and KPIs to ensure awareness, distribute resources to…

Assistant Project Manager - Affordable Housing Construction

Company: Michael Page

Location: Chicago, IL

Posted Oct 01, 2025

Proficiency in Microsoft Office and project management tools. Monitor project progress and report updates. Prepare invoices, estimates, and meeting schedules.

Tax Accountant - 2+ Yrs Paid Tax Experience Required

Company: Intuit

Location: Chicago, IL

Posted Sep 30, 2025

Interact with customers both in-person and through Intuit’s state-of-the-art video communication tools. Minimum of 2 years of paid experience filing 30 or more…

OTR CDL-A Liquid Bulk Tanker Owner Operator Drivers

Company: Liquid Cargo

Location: East Chicago, IN

Posted Sep 30, 2025

Responsible for transporting liquid bulk products across long distances *OTR, 2-3 weeks out* and *truck must have air compressor and hose rack*.

Full Stack Software Developer

Company: Bois D'Arc International

Location: Downers Grove, IL

Posted Sep 30, 2025

The ideal candidate is proficient across the tech stack and capable of building secure, scalable, and user-friendly internal tools that improve business…

Project Manager - Luxury Residential

Company: Michael Page

Location: Chicago, IL

Posted Oct 01, 2025

Bachelor's degree in Construction Management or related field preferred. Ensure quality control and compliance with design specifications and building codes.

Customer Service Representative/Check in

Company: Temco Logistics

Location: Northlake, IL

Posted Sep 30, 2025

Answer phone calls and respond to emails promptly, addressing customer questions, concerns, and requests. Ensure customers are satisfied with their delivery and…

Project Manager - Remote - Big Box

Company: Michael Page

Location: Chicago, IL

Posted Oct 01, 2025

Coordinate with stakeholders, contractors, and team members to ensure project objectives are met. Familiarity with project management tools and software.

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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