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.

HR Coordinator

Company: SpotOn

Location: Chicago IL

Posted Aug 31, 2022

SpotOn is a company that helps small businesses and restaurants compete and win with technology. They are looking for a HR Coordinator to support and scale their organization. The role involves providing administrative and operational support for all people processes, being the first level support for all employee inquiries, and assisting in the creation of standardized tools and templates.

Operations Support Associate

Company: Silverwork Solutions

Location: Chicago IL

Posted Aug 31, 2022

Silverwork is a growing FinTech startup looking for an Operations Support Associate to supply critical tactical support to their Product Management and Software Engineering teams. The role involves addressing client and product issues, troubleshooting, and conducting corrective measures. The company offers a competitive salary, generous bonus opportunities, and a remote first environment.

Director, Airborne Hardware

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 31, 2022

The job posting is looking for a highly self-motivated leader to develop and implement innovative in-flight connectivity solutions. The role requires experience in avionics, leadership, and communication. The company emphasizes personal and professional growth, and offers great benefits and a fun culture.

Demand Planning Analyst

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 30, 2022

Intelsat Inflight is a rapidly growing company that is shaping the future of inflight internet experience. As a Demand Planning Analyst, you will collaborate with teams to ensure equipment and resources are available to meet installation and maintenance needs. The company is looking for a highly analytical and motivated individual who can drive processes and make a direct impact on the business.

Business Development Sales Representative (collegiate graduate 2022)

Company: MoLo Solutions

Location: Chicago IL

Posted Aug 30, 2022

MoLo Solutions is a start-up company that offers a business development representative position. The job involves growing the business from the ground up by building relationships with customers across North America. The company provides transportation solutions to its customers and is looking for an entrepreneurial and sales-minded individual with a strong work ethic.

Growth Marketing Manager - B2C

Company: Keeper Security, Inc.

Location: Chicago IL

Posted Aug 31, 2022

Keeper is hiring a talented B2C Growth Marketing Manager to join their rapidly growing team. The company is transforming the way organizations and individuals protect their credentials and sensitive digital assets. The job requires experience in performance marketing, CRO, customer marketing, and analytics, and offers a range of benefits.

Enterprise Account Executive

Company: Kalderos

Location: Chicago IL

Posted Aug 29, 2022

Kalderos is a company that values transparency, trust, and equity in the healthcare community. They are looking for an Enterprise Account Executive to join their team and help them achieve their goals. The company offers a range of benefits, including continuous growth and development, celebrating employee milestones, and a fair PTO system.

Operations QA Analyst

Company: Blueground

Location: Chicago IL

Posted Aug 28, 2022

Blueground is a company that aims to make people feel at home wherever they choose to live. They have grown significantly since their founding in 2013 and are now hosting guests in over 8,000 homes across 20+ cities. They value their team members and offer a range of benefits, including flexible work arrangements, competitive compensation, and a culture of collaboration and inclusiveness.

Sr Engineer, Portal Integration Test

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 30, 2022

The job posting is looking for a testing engineer to work on automated and manual testing endeavors. The role involves partnering with developers and other departments to define and influence the overall performance of products. The company emphasizes personal and professional growth, has awesome benefits, and a fun and diverse culture.

Software Engineering Manager - EcoSystem Platform

Company: Avant

Location: Chicago IL

Posted Aug 28, 2022

Avant is looking for a Software Engineering Manager to build their Ecosystem Platform Team. The role involves driving software engineer hiring, taking ownership of in-house built services, and collaborating with other teams. The company values authenticity, collaboration, problem-solving, and customer focus.

Senior Data Engineer

Company: Kalderos

Location: Chicago IL

Posted Aug 28, 2022

Kalderos is a healthcare technology organization building unifying technologies for transparency, trust, and equity. They are looking for a collaborative organizational builder with experience in data engineering, particularly in the healthcare industry. The company offers continuous growth, celebrating employee milestones, work-from-home reimbursement, a fair PTO system, and a 401K plan with a company match. They value collaboration, empowerment, feedback, and curiosity.

Senior Engineer, Backend (Money Squad)

Company: SpotHero

Location: Chicago IL

Posted Aug 30, 2022

SpotHero is seeking a Senior Backend Engineer to join the Money Squad. The role involves designing, developing, and releasing high-quality functionality, as well as collaborating with the team to deliver quality products. The company offers excellent benefits, flexible PTO policy, and a casual work environment.

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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