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.

Manager, Investment, Affiliate and Influencer

Company: Rise

Location: Chicago, IL

Posted Jul 30, 2025

Serve as trusted advisor and consultant to clients on calls, emails, and in-person meetings. The Manager will provide strategic direction to team members…

Electrical Project Manager (Electrical Experience Required)

Company: Sievert Electric Service & Sales Co Inc

Location: Forest Park, IL

Posted Jul 30, 2025

The Electrical Project Manager will be responsible for overseeing electrical contracting projects, managing budgets, leading electrical design efforts, and…

Data Analyst - Regulatory Data and Systems ( or recent graduate opportunity)

Company: BMO US

Location: Chicago, IL

Posted Jul 30, 2025

Participates in the design, implementation and management of core business processes to ensure the accuracy of risk data used in reporting.

Owner Operator Truck Driver

Company: HTA Transpotation INC

Location: Chicago, IL

Posted Jul 30, 2025

Proven experience (2 years) in commercial driving with a valid driver's license (CDL required). As an Owner Operator, you will have the flexibility to manage…

Department Manager - Plumbing

Company: American Vintage Home

Location: Chicago, IL

Posted Jul 30, 2025

Assist sales staff with design, layout, equipment, and material selections when needed. Identify technical weaknesses in trainees and provide support and…

Software Engineer

Company: Morningstar

Location: Chicago, IL

Posted Jul 30, 2025

You will be exposed to all aspects of product development: design of user experience, system architecture, model development, productionizing models, API/…

Project Manager, Supply Chain Continuity

Company: Ferrara Candy Company, Inc.

Location: Chicago, IL

Posted Jul 30, 2025

Financial analysis and/or cost accounting experience within a manufacturing business. Knowledge of technical functions such as planning, procurement,…

Customer Service Representative - Full-Time

Company: United Airlines

Location: Chicago, IL

Posted Jul 30, 2025

You will be interacting with our domestic and international customers in our lobbies and at gates, helping them with ticketing, baggage, greeting customers as…

CDL A Truck Driver Owner Operators w/ Sleeper Cab & Own Authority / All Diesel Covered/ Midwest Run

Company: SLS Transportation

Location: Chicago, IL

Posted Jul 30, 2025

Over 30 years of experience in servicing Confectionery, Pharmaceutical, Nutraceutical, Food, and Grocery Industries. Our Drivers are guaranteed stability all…

Senior Financial Analyst, Data Center Acquisitions, Energy finance

Company: Google

Location: Chicago, IL

Posted Jul 30, 2025

Bachelor's degree in Business, Finance, Economics, Statistics, or another quantitative field, or equivalent practical experience.

Mortgage Sales Account Executive / Area Manager

Company: Lendsure Mortgage- Wholesale Non -QM

Location: Chicago, IL

Posted Jul 30, 2025

Your duties shall be to solicit and obtain, on a wholesale basis, residential mortgage loan submissions which conform to LendSure’s loan programs, underwriting…

Overnight Customer Service Representative

Company: Midwest Foods

Location: Chicago, IL

Posted Jul 30, 2025

Manage high volume of phone calls. Experience in data entry and navigating databases. Able to handle finishing bills for 40 routes (600 invoices) in a timely…

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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