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.

Research Lead, Market and Consumer Focus

Company: Rightpoint

Location: Chicago IL

Posted Sep 17, 2022

Rightpoint is a global experience leader, offering strategic customer experience consulting services. They have been recognized for their work in customer experience and are looking for passionate, talented people to join their team. The Research Lead (Consumer and Market Focus) role involves generating and applying insights to develop strategic customer experience programs for clients. The company offers flexible work arrangements, great benefits, and a commitment to diversity, equity, and inclusion.

Software Engineer - Web

Company: NinjaTrader

Location: Chicago IL

Posted Sep 17, 2022

NinjaTrader is a growth-stage FinTech company seeking a Software Engineer - Web to join their team. The company is building products and services for active traders and has a unique employee-centric culture. The role involves designing, developing, and implementing web applications, and requires experience with JavaScript, React.js, and CSS.

Manager, Software Portal Test

Company: Intelsat

Location: Chicago IL

Posted Sep 13, 2022

The job posting is looking for a lead or manager role in a company called Intelsat Inflight, which is a company that provides inflight internet services. The job requires experience in systems engineering, system integration testing, and test and defect management tools. The company emphasizes personal and professional growth, has awesome benefits, and a fun and diverse culture.

Sr Product Manager

Company: Kalderos

Location: Chicago IL

Posted Sep 12, 2022

Kalderos is a technology company that delivers solutions to simplify the coordination of drug discount programs in the US healthcare system. They are looking for a seasoned Product Manager to scale an AI-driven product and drive core revenue growth.

Underwriting Assistant

Company: Argo Group

Location: Chicago IL

Posted Sep 15, 2022

Argo Group is a leader in specialty insurance with a vibrant culture built on respect, equality, wellness, and opportunity. The company offers a flexible workplace, continuous learning, and professional development opportunities. It values diversity, inclusivity, and community outreach.

Program Manager

Company: Intelsat

Location: Chicago IL

Posted Sep 17, 2022

The job posting is looking for a Program Manager to lead all aspects of program delivery, including project planning, resource allocation, and financial metrics. The role requires a strong leader who can build and foster professional relationships across multiple business units, and has experience using program management tools and methodologies.

Director, DAS/Small Cell RF Design

Company: Boingo Wireless

Location: Chicago IL

Posted Sep 15, 2022

Boingo Wireless is a company that helps people stay connected by providing wireless networks in various locations. The company is looking for a Director of DAS/Small Cell RF Design to lead the design of in-building cellular networks. The job requires a strong understanding of cellular network technologies and experience in carrier deployments and design requirements.

Senior iOS Software Engineer

Company: Fetch Rewards

Location: Chicago IL

Posted Sep 15, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. They are looking for a Senior iOS Software Engineer to build and maintain a world-class mobile application.

Network and Systems Administrator

Company: SpotOn

Location: Chicago IL

Posted Sep 17, 2022

SpotOn is a technology company that helps small businesses and restaurants compete and win with its marketing software, website development, and other solutions. The company has raised $300M in funding and has been recognized for its great workplace culture. It is looking for an IT Systems Engineer to join its team and work on building out the architecture and supporting processes for its IT and critical business systems portfolio.

Sr. New Accounts Associate

Company: NinjaTrader

Location: Chicago IL

Posted Sep 17, 2022

NinjaTrader is a FinTech company that provides software and brokerage services to traders. They are looking for a Sr. New Accounts Associate to join their team, providing world-class support to customers.

Account Executive - White Label

Company: Paro

Location: Chicago IL

Posted Sep 13, 2022

Paro is seeking an Account Executive to join their ‘White Label’ team. The role involves building relationships with professional services firms, acquiring new partners and clients, and expanding the client portfolio. The company offers a comprehensive benefits package, unlimited vacation, remote work options, and a health and wellness stipend.

iOS Software Engineer

Company: Fetch Rewards

Location: Chicago IL

Posted Sep 15, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. They are looking for an iOS Software Engineer to build and maintain a world-class mobile application.

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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