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.

Implementation Manager

Company: Augment

Location: Chicago, IL

Posted Jul 28, 2025

Our founders recognized a pattern: talented professionals were stuck handling manual data entry, phone calls, and repetitive tasks, instead of focusing on high-…

Customer Success Director

Company: Greenshoe AI

Location: Chicago, IL

Posted Jul 28, 2025

You will own the customer experience, develop trusted advisor relationships, and drive adoption, engagement, and retention. Be as specific as possible.

Carpenter / Fireplace Installer

Company: American Heritage Inc.

Location: Chicago, IL

Posted Jul 28, 2025

*Utilize Diverse Trade Skills:* Apply your experience in carpentry, plumbing, electrical, and HVAC systems to ensure seamless and comprehensive installations.

Bi-lingual Member Support Representative-French-English

Company: Midtown Athletic Club

Location: Chicago, IL

Posted Jul 28, 2025

Eager to answer a high volume of calls, emails, and/or tickets daily. Maintain a positive, empathetic, and professional attitude toward members at all times…

Data and Business Analyst

Company: Illinois Institute of Technology

Location: Chicago, IL

Posted Jul 28, 2025

Defines functional requirements for automating business processes and oversees data entry and user protocol for non-technical solutions.

Sous Chef

Company: FAIRMONT

Location: Chicago, IL

Posted Jul 28, 2025

Create unforgettable culinary experiences for our guests. Consistently offer professional, friendly and proactive guest service while supporting fellow…

Customer Service Associate

Company: Jet Brite

Location: Chicago, IL

Posted Jul 28, 2025

Strive for customer satisfaction by ensuring a thorough and enjoyable wash for all guests. Must live within a 25-minute commute of Jet Brite location.

Event Floorplan Designer and Graphic Production Specialist

Company: SourceOne Events

Location: Elmhurst, IL

Posted Jul 28, 2025

*Skills:* Proficiency in CAD software, graphic design tools (e.g., Adobe Creative Suite), and CNC machine operation. 401K with a company match up to 7%.

People Analyst, Analytics for Googlers

Company: Google

Location: Chicago, IL

Posted Jul 28, 2025

Whether recruiting the next Googler, refining our core programs, developing talent, or simply looking for ways to inject some more fun into the lives of our…

Sales Associate

Company: The LaSalle Network

Location: Addison, IL

Posted Jul 28, 2025

Follow up on previous sales quotes, new leads, completed purchase orders and sales calls. Ability to interpret blueprints, drawings, and diagrams.

Sous Chef/Kitchen Manager

Company: Pour Destino

Location: Elmhurst, IL

Posted Jul 28, 2025

Communicate effectively to solve challenges, implement new strategies, and contribute directly to the success of both restaurants.

Executive Chef - NRO

Company: Amada Restaurants

Location: Chicago, IL

Posted Jul 28, 2025

Associate or bachelor's degree in culinary arts highly preferred. Minimum 3 years culinary leadership experience, preferably in a high profile, culinary driven…

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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