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.

Sales Operations Lead

Company: Janus Health

Location: Chicago IL

Posted Aug 19, 2022

Janus is a company that believes in improving healthcare efficiency and is committed to growing and empowering an inclusive community. They are looking for a Sales Operations Lead to join their team, which is responsible for growing the company's footprint across healthcare customers.

Product Marketing Manager - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 23, 2022

Black Spectacles is a purpose-driven company that aims to educate and inspire architects. They are looking for a Product Marketing Manager to join their team and help them grow. The company offers a range of benefits, including unlimited vacation, flexible work arrangements, and a commitment to diversity and inclusion.

Carrier Sales Representative (experienced)

Company: MoLo Solutions

Location: Chicago IL

Posted Aug 22, 2022

The job description is for a Carrier Sales Representative at MoLo Solutions, a logistics company. The role involves developing and maintaining relationships with carriers, sourcing new capacity, and ensuring consistent carrier relationships. The company offers a casual and fun start-up culture, extensive industry training, and opportunities for growth and advancement.

Senior Mobile Developer - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 25, 2022

Black Spectacles is a purpose-driven company that is looking for a Senior Mobile Developer to join their team. The company is committed to educating and inspiring architects across the world and is expanding its team of enthusiastic go-getters. The role involves developing and launching mobile applications for iOS and Android devices, integrating with backend systems, and owning and managing app performance and analytics.

People Operations Coordinator

Company: Silverwork Solutions

Location: Chicago IL

Posted Aug 25, 2022

The job posting is for a People Operations Coordinator at Silverwork, a fintech startup. The role involves driving the tactical aspects of People Operations, building and supporting a strong and scalable team, and making a lasting impact. The ideal candidate has HR or People Operations experience, is tech-savvy, and has a people-first focus.

Senior Product Manager, Data Ingestion

Company: Kalderos

Location: Chicago IL

Posted Aug 20, 2022

Kalderos is a high-growth, Series-B company looking to scale rapidly in 2022. They are seeking a seasoned Product Manager to own, define, and execute the roadmap for their data platform, which acquires, ingests, and analyzes over 100M claims to identify tens of millions in pharmaceutical non-compliance each year. The role offers leadership opportunities, general experience guidelines, and company perks.

Customer Success Manager

Company: HealthJoy

Location: Chicago IL

Posted Aug 19, 2022

HealthJoy is a company that offers a simplified benefits experience for users, with a mission to impact every single one of its users. The company has experienced explosive growth and has received several awards. It offers a range of benefits to its employees, including healthcare benefits, flexible PTO, and a remote work stipend.

Vice President of Finance

Company: CancerIQ

Location: Chicago IL

Posted Aug 18, 2022

Cancer IQ is looking for a VP of Finance to join their team. The role involves managing financial accounting and reporting, investor relations, and ongoing financial projects. The company is rapidly growing and requires a candidate with experience in accounting, financial planning, and analysis.

Executive Director of Growth

Company: Janus Health

Location: Chicago IL

Posted Aug 21, 2022

Janus Health Technologies is a company that aims to improve the lives of administrative workers in the healthcare industry. They are looking for an Executive Director of Growth to build and execute the overall sales approach to their Health System customers. The company values its employees, is entrepreneurial, and focused on creating a strong culture.

Technical Product Manager - ML Ops and Infra Ops

Company: Avant

Location: Chicago IL

Posted Aug 23, 2022

Avant is looking for a Technical Product Manager to lead Machine Learning Operations and Infra Operations Pod. The role involves modernizing technical infrastructure, enabling business users to leverage Avant technology, and solving critical business problems.

Growth Strategy Associate

Company: Avant

Location: Chicago IL

Posted Aug 19, 2022

The job posting is for a Growth Strategy associate who will use data analysis to help unlock new growth opportunities. The role involves breaking down complex problems, analyzing acquisition funnels, and leading loan pricing strategy. The company, Avant, values authenticity, collaboration, problem-solving, and customer-centricity.

Content Marketing Manager - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 23, 2022

Black Spectacles is a purpose-driven company that aims to educate and inspire architects. They are looking for a Content Marketing Manager to join their team, who will be responsible for creating content that drives meaningful results. The company offers a range of benefits, including unlimited vacation, flexible work arrangements, and a commitment to diversity and inclusion.

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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