Unlimited Pto Jobs in Chicago, IL

16,263 open positions · Updated daily

Looking for Unlimited Pto jobs in Chicago, IL? Browse our curated listings with transparent salary information to find the perfect Unlimited Pto position in the Chicago, IL area.

Staff / Principal Data Engineer

Company: SpotHero

Location: Chicago, IL

Posted Jan 27, 2023

None Found

Sales Enablement Manager

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Jan 27, 2023

None Found

Associate Principal, Cyber Defense

Company: OCC

Location: Chicago, IL

Posted Jan 29, 2023

None Found

Sr. Sales Operations Analyst

Company: Upwork

Location: Chicago, IL

Posted Jan 28, 2023

None Found

Payroll Specialist

Company: Shipbob Inc

Location: Chicago, IL

Posted Jan 28, 2023

ShipBob is a cloud-based logistics platform that partners with e-commerce businesses to help them improve their fulfillment processes. The company is looking for a Payroll Specialist to join their team, with a competitive salary range of $41,250 - $68,750.

Systems Support Engineer (Wed-Sun)

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Jan 31, 2023

Keeper is hiring a System Support Engineer to join their team. The job requires 5+ years of IT management experience and involves providing technical support to clients. The company offers a range of benefits, including medical, dental, and vision insurance, and a generous PTO plan.

Payroll Specialist

Company: Shipbob Inc

Location: Chicago, IL

Posted Jan 28, 2023

None Found

Director of Marketing

Company: Campus Ink

Location: Chicago, IL

Posted Jan 27, 2023

None Found

Financial Analyst

Company: FOURKITES

Location: Chicago, IL

Posted Jan 27, 2023

None Found

Creative Account Manager

Company: Campus Ink

Location: Chicago, IL

Posted Jan 27, 2023

None Found

Copywriter

Company: NinjaTrader

Location: Chicago, IL

Posted Jan 29, 2023

This job posting is for a Copywriter position at NinjaTrader, a FinTech company offering award-winning software and brokerage services. The role involves creating engaging content for various platforms, conducting research, and ensuring content aligns with business goals. The ideal candidate should have an associate or bachelor's degree in marketing, communications, journalism, or a related field, financial industry experience, excellent writing skills, and the ability to work independently or in a team.

Frequently Asked Questions

What are typical salary ranges for unlimited PTO tech roles by seniority?
Entry‑level engineers start around $90k–$120k, mid‑level $120k–$160k, senior $160k–$200k, staff $200k–$250k, and principal $250k+ annually. Product managers and designers have comparable ranges, while data scientists and DevOps engineers follow similar tiers.
What skills and certifications are required for unlimited PTO positions?
Software engineers should master Go or Rust, AWS Certified Solutions Architect, and Certified Kubernetes Administrator. Product managers need Agile Scrum or SAFe certification, proficiency in Jira, and data‑analysis skills in SQL and Python. UX designers should be fluent in Figma, have a portfolio, and understand accessibility standards. Data analysts require expertise in Snowflake, Tableau, and statistical modeling. DevOps engineers need Terraform, GitHub Actions, and CI/CD best practices.
Is remote work available in unlimited PTO roles?
Yes. Most companies offering unlimited PTO—such as GitHub, Atlassian, and Shopify—provide fully remote or hybrid options. Remote‑first culture pairs well with unlimited PTO, as employees can schedule time off around project milestones and global deadlines.
What career progression paths exist in unlimited PTO tech roles?
Typical ladders progress from Associate/Junior to Mid, Senior, Staff, and Principal levels. Unlimited PTO allows professionals to focus on skill development, certifications, and cross‑team leadership, accelerating promotion timelines. Mentorship programs and internal mobility initiatives further support upward movement.
What industry trends affect unlimited PTO positions?
The shift toward outcome‑based performance, increased emphasis on mental health, and the rise of remote‑first teams are driving the adoption of unlimited PTO. Companies use the benefit to attract high‑talent, reduce turnover, and promote a culture of trust and autonomy. Data shows that firms offering unlimited PTO often report higher productivity and employee satisfaction scores.

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