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.

Security Analyst

Company: WiseTech Global

Location: Chicago, IL

Posted Mar 13, 2025

Able to communicate effectively in verbal and written format with technical and non-technical audiences. Relevant certification such as CISSP, CCNA, CompTIA…

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Registered Nurse -Pediatrics OVERNIGHT 8PM to 6AM $38/HR (IN HOME HEALTH)

Company: BrightStar Care of Orland Park/Will County

Location: Alsip, IL

Posted Mar 13, 2025

Unencumbered license as a RN in the state of Illinois. Perform patient assessments and monitor vital signs, administering medications and treatments as…

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loan repayment program malpractice insurance relocation assistance

Obstetrics Gynecology

Company: Advocate Health

Location: Chicago, Illinois

Posted Mar 18, 2025

View Details Apply on healthecareers.com

Journeyman Plumber

Company: Leapros Skilled Trades

Location: Chicago, IL

Posted Mar 15, 2025

Valid driver’s license and reliable transportation. Respond to emergency plumbing calls and provide timely solutions. Must be able to climb stairs and ladders.

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Licensed Plumber

Company: Precision Today

Location: Franklin Park, IL

Posted Mar 15, 2025

Deliver sound plumbing diagnostics, repairs, and installs. Enjoy the convenience of taking your truck home each night and dispatching directly from home!

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Drain Tech

Company: Precision Today

Location: Franklin Park, IL

Posted Mar 13, 2025

Complete all drain cleaning, jetting and cable work related to in-home, service calls. Company supplied Vehicle – fully stocked, cell phone, and tablets.

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Physical Education/Health Teacher SY 25-26

Company: ACE Amandla Charter High School

Location: Chicago, IL

Posted Mar 13, 2025

Acquire professional knowledge and learn of current developments in the educational field by seeking out and attending seminars, workshops or professional…

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Senior Accountant

Company: Porte Brown, LLC

Location: Elk Grove Village, IL

Posted Mar 19, 2025

Prepare tax returns, including consolidated or multi-state business returns, complex pass-through entities and complex individuals.

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Combo Pipe Welder

Company: STARCON INTERNATIONAL

Location: Bedford Park, IL

Posted Mar 18, 2025

Read and interpret blueprints, technical drawings, and specifications to determine the appropriate welding process.

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Community Developer

Company: Ripple Fiber

Location: Lombard, IL

Posted Mar 13, 2025

A bachelor's degree in communications, business, or a related field. This role will work closely with state and local municipalities, developers, and community…

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Luxury Custom Stylist / Sales Associate

Company: BALANI Custom Clothiers

Location: Chicago, IL

Posted Mar 19, 2025

Aptitude to learn technical skills such as measuring, fitting, styling, and electronic order entry. Structured, formal training program to develop key industry-…

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Sous Chef

Company: Shaw's Crab House

Location: Chicago, IL

Posted Mar 14, 2025

Use tact and good judgment when dealing with challenges pertaining to guests, vendors and employees, and respond with patience and courtesy.

View Details Apply on SimplyHired

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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