Generous Paid Time Off Jobs in Chicago, IL

73,230 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.

UI/UX Designer

Company: Velvetech

Location: Chicago, IL

Posted Feb 22, 2025

Proficiency in AI-driven design tools such as Figma with AI plugins, Adobe XD with Sensei features, or similar is required.

Creative Lead for Brand Content / Digital Experience

Company: ServiceNow

Location: Chicago, IL

Posted Feb 28, 2025

ServiceNow, a global market leader in AI-enhanced technology, is seeking a Creative Director for Digital Experiences and Content. The role involves leading the creative development of high-impact brand-building experiences across digital platforms, including social media, thought leadership, and digital media. The ideal candidate should have 15+ years of experience in the creative industry, with a proven track record of driving groundbreaking creative in B2B settings. They should be an expert in digital and social craft, with a deep understanding of UX/UI best practices and emerging content formats. The role offers a base pay of $159,400 - $279,000 plus equity, variable incentive compensation, and benefits.

Experienced Residential Electrician

Company: Zanite Electrical

Location: Chicago, IL

Posted Feb 26, 2025

Valid driver’s license and clean driving record. Assembling, installing, testing, and maintaining electrical or electronic wiring, equipment, appliances,…

Registered Nurse (RN)-Home Health-Streeterville & Surrounding Areas

Company: Luxe Home Health

Location: Streeterville, IL

Posted Feb 27, 2025

A valid IL driver’s license, auto insurance, reliable transportation, and the ability to travel throughout the service area are essential. Up to $90 per visit.

Managing Associate Teacher - Little Village

Company: Carole Robertson Center for Learning

Location: Chicago, IL

Posted Feb 27, 2025

Lead the collaboration with the TA, Aides, and Program Advisor team in the creation and facilitation of studies to support weekly lesson plans, including daily…

AI Training Physics - AI Trainer

Company: DataAnnotation

Location: Chicago, IL

Posted Feb 21, 2025

You can work on your own schedule. You will measure the progress of these AI chatbots, evaluate their logic, and solve problems to improve the quality of each…

Director, Information Security

Company: Beyond Finance

Location: Chicago, IL

Posted Feb 28, 2025

Beyond Finance is seeking a Director of Information Security with extensive experience in the field, preferably in a financial services environment. The role involves leading a team of security professionals, integrating security best practices into the software development lifecycle, and managing relationships with key security vendors. The company offers a collaborative work environment, competitive benefits, and opportunities for career development. They are looking for someone with a proven track record in developing and implementing successful information security programs, in-depth knowledge of security frameworks, and experience with DevSecOps methodologies.

Senior Data Analyst

Company: Chicago Public Schools

Location: Chicago, IL

Posted Feb 24, 2025

Effectively communicate technical findings to both technical and non-technical audiences. Strong understanding of statistical concepts and data analysis…

Internal Audit & SOX IT Senior

Company: Chime

Location: Chicago, IL

Posted Mar 01, 2025

Chime is seeking an experienced IT SOX Senior for a world-class SOX program implementation. The role involves leading IT SOX coordination, planning and executing IT-focused internal audits, consulting with IT and Engineering teams, and assessing changes affecting internal controls. The ideal candidate should have 3+ years of IT SOX experience, strong knowledge of Sarbanes-Oxley, PCAOB Auditing Standards, and the COSO framework. Excellent communication skills, project management, and external auditor relationship management are required. Chime offers a competitive salary, benefits, and a hybrid work policy.

Plumbing Service Technician

Company: Stellar Plumbing

Location: Elk Grove Village, IL

Posted Feb 24, 2025

Plumbing Service Technicians determine service needs, quote prices in the field and perform repairs. Must be willing to pursue, develop, and participate in…

Lead Software Engineer in Test

Company: Beyond Finance

Location: Chicago, IL

Posted Feb 25, 2025

Beyond Finance is a rapidly growing financial technology company committed to helping individuals escape debt. They are seeking a Lead Software Development Engineer in Test to join their team. The role involves working closely with the team to verify software quality, planning and building automation, and mentoring other team members. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career development.

IT Technical Specialist

Company: UL Solutions

Location: Chicago, IL

Posted Mar 01, 2025

The IT Technical Specialist role involves providing C-suite technology support, managing conference room technology, performing PC imaging and deployment, troubleshooting hardware and software issues, coordinating vendor support, and managing end-user technology needs. The role requires a professional, self-motivated individual with strong communication skills, multitasking abilities, and a proven customer service background. The position involves onsite and remote support, travel, and lifting up to 50 lbs. The estimated salary range is $55,000 to $65,000, with additional benefits including health, wellness, and retirement savings. The role is part of a high-performing IT team that supports innovative companies worldwide.

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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