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.

Tax Accountant (Associate Principal)

Company: OCC

Location: Chicago IL

Posted Sep 23, 2022

The Options Clearing Corporation (OCC) is a leading financial institution that provides clearing and settlement services for options, futures, and securities lending transactions. The company offers a collaborative work environment, competitive benefits, and opportunities for professional growth.

RFP Administrator

Company: Keeper Security, Inc.

Location: Chicago IL

Posted Sep 22, 2022

Keeper Security is hiring a talented RFP Administrator to join their sales team. The role involves managing the full lifecycle of the RFP/RFI process, supporting sales and engineering teams, and collaborating with various departments. The company offers a range of benefits, including medical, dental, and vision insurance, 401(k), and a generous PTO plan.

Technical Product Manager

Company: AdAction

Location: Chicago IL

Posted Sep 23, 2022

AdAction is looking for a Technical Product Manager to own integrations solutions for clients. The role requires a mix of management and technical skills to impact a growing product and team.

Actuarial Analyst - Data

Company: Argo Group

Location: Chicago IL

Posted Sep 23, 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 also has a strong focus on diversity, equity, and inclusion, and provides a comprehensive benefits package.

Senior Engineering Manager, Engineering

Company: SpotHero

Location: Chicago IL

Posted Sep 23, 2022

SpotHero is seeking a Senior Engineering Manager to lead and inspire an Engineering squad(s) composed of backend engineers and QA. The role involves building products that support the company's scaling challenges, providing technical and professional growth for each person, and ensuring high-quality code.

Staff Cloud Infrastructure Engineer

Company: SADA

Location: Chicago IL

Posted Sep 22, 2022

The job posting is for a Staff Cloud Infrastructure Engineer at SADA, a company that has been named the largest partner in North America for Google Cloud portfolio of products. The role involves working on high-quality infrastructure projects, providing thought leadership, and delivering complex projects. The company values diversity and inclusivity and offers competitive benefits and a positive work environment.

UI/UX Designer

Company: Inspire11

Location: Chicago IL

Posted Sep 23, 2022

The text describes a company called Inspire11 that values collaboration, authenticity, and diversity. They believe in empowering their team members to take ownership of their careers and provide a work-life balance. The company culture is vibrant and light-hearted. The role of a UX/UI Designer involves collaborating with clients and internal teams to design user experiences, conducting research, and creating design artifacts.

Associate Front End Developer

Company: Rightpoint

Location: Chicago IL

Posted Sep 22, 2022

Rightpoint is a global experience leader that helps clients embed experience across their operations. They are looking for a Front-End Developer to join their team and offer a range of benefits and perks.

Staff Accountant

Company: OCC

Location: Chicago IL

Posted Sep 23, 2022

The Options Clearing Corporation (OCC) is a leading financial organization that provides clearing and settlement services for options, futures, and securities lending transactions. OCC offers a collaborative work environment, competitive benefits, and opportunities for professional growth.

Senior React/JavaScript Developer

Company: Rightpoint

Location: Chicago IL

Posted Sep 23, 2022

Rightpoint is a global experience leader that helps clients embed experience across their operations. They are searching for passionate and talented people to join their team. The company is committed to diversity, equity, and inclusion and offers a range of benefits and perks.

Associate Back End Developer

Company: Rightpoint

Location: Chicago IL

Posted Sep 22, 2022

Rightpoint is a global experience leader that helps clients embed experience across their operations. They are looking for passionate and talented people to join their team. The company offers a range of benefits and perks, including flexible PTO, hybrid work environment, and continuous training opportunities.

Jr. Java Developer

Company: Enfusion

Location: Chicago IL

Posted Sep 22, 2022

Enfusion is a pioneer in developing innovative cloud investment management software, analytics, and managed services. They help fund managers streamline operations, mitigate risk, and improve transparency. The company is committed to the growth and well-being of its people and offers a competitive compensation and benefits package.

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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