Generous Paid Time Off Jobs in Chicago, IL

73,229 open positions · Updated daily

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.

Okuma CNC 5-Axis Machinist

Company: Accelera

Location: Elk Grove Village, IL

Posted May 16, 2025

We are seeking an experienced Okuma 5-axis Machinist (also known as CNC Machinist, CNC Machine Operator) to operate CNC machines, read blueprints, perform…

Maintenance Plumber

Company: Accelera

Location: Chicago, IL

Posted May 16, 2025

Proficiency in using pipe threading and cutting equipment, power and hand tools, and a gas torch. As a Pipe Fitter (also known as Pipefitter, Steamfitter, or…

Sr. Mgr, Software Engineering

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

Experience leading teams through ambiguity by driving technical design and delivery decisions. Capital One will consider for employment qualified applicants…

Senior Manager, Software Engineer (People Leader)

Company: Capital One

Location: Chicago, IL

Posted May 19, 2025

Capital One will consider for employment qualified applicants with a criminal history in a manner consistent with the requirements of applicable laws regarding…

People Intelligence and Engagement Partner

Company: Chainlink Labs

Location: Chicago, IL

Posted May 16, 2025

Tuning into the Web 3 industry and business to keep abreast with trends to reflect in own workstreams. High proficiency in operational tools (e.g., Sheets,…

Armed Security Officer/Driver

Company: Kates Detective Agency

Location: Chicago, IL

Posted May 17, 2025

Remain in compliance with local, state, and federal regulations. Clean driving record/No tickets or moving Violations. Salary Range: $18.00 - $18.00 Hourly.

CNC Vertical Turning Machinist

Company: Accelera

Location: Elk Grove Village, IL

Posted May 16, 2025

Duties include following written instructions, reading blueprints, performing machining operations to close tolerances, and ensuring parts meet specifications.

Clinical Analyst

Company: JACKSON PARK HOSPITAL AND MEDICAL CENTER

Location: Chicago, IL

Posted May 16, 2025

Assist in the development and implementation of new digital tools and technologies to improve patient outcomes. Associates Degree Minimum, Bachelors preferred.

Electrician

Company: Accelera

Location: Northlake, IL

Posted May 16, 2025

As an Electrician (also known as Electrical Technician, Industrial Electrician), you will troubleshoot programmable controllers and A/C and D/C drives, perform…

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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