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.

BSA/AML Compliance Analyst

Company: Avant

Location: Chicago IL

Posted Nov 19, 2022

Avant is looking for a new BSA/AML Compliance Analyst to join their 30+ person Legal and Compliance Department. The role involves conducting transaction monitoring, reviewing alerts, and escalating suspicious activity. The company offers a range of benefits, including flexible work environment, unlimited paid time off, and professional development opportunities.

Customer Success Manager - Manufacturing

Company: Kalderos

Location: Chicago IL

Posted Nov 18, 2022

Kalderos is a healthcare technology organization focused on pharmaceutical pricing transparency, trust, and equity. They are looking for a Customer Success Manager-Manufacturing to support drug manufacturers in onboarding and production operations, and to engage with states and pharmacy benefit managers in dispute resolution. The company offers medical, dental, and vision benefits, 401k with company match, flexible work schedule, unlimited PTO, and more. They value collaboration, diversity, and inclusion.

Admissions Advisor I

Company: Everspring

Location: Chicago IL

Posted Nov 18, 2022

The job description is for an Online Admissions Advisor at Everspring, Inc. The role involves communicating with potential online students, advising them on the admission process, and guiding them through their education journey. The company is an ed-tech trailblazer that creates customized digital solutions for top universities.

Senior Engineer, Front End

Company: SpotHero

Location: Chicago IL

Posted Nov 18, 2022

SpotHero is seeking a Senior Front End Engineer to work on their flagship consumer products, building out new features and improving existing ones. They value humility, a strong work ethic, flexibility, collaboration, technical curiosity, and constant learning. They offer excellent benefits, flexible PTO, a parking stipend, and the opportunity to work with a fun and innovative team.

IT Manager

Company: Civis Analytics

Location: Chicago, Illinois, United States

Posted Nov 19, 2022

None Found

Senior Data Engineer

Company: SpotHero

Location: Chicago IL

Posted Nov 19, 2022

SpotHero is seeking a Senior Data Engineer to join the Data Engineering squad. The role involves designing and implementing high-quality software in Python, strong SQL skills, and experience with Airflow, Luigi, or other ETL scheduling tools. The company offers excellent benefits, flexible PTO policy, and a workplace recognized as one of Chicago's Best Places to Work for Women Under 35.

Associate, Corporate Communications

Company: OCC

Location: Chicago IL

Posted Nov 18, 2022

The Options Clearing Corporation (OCC) is a leading organization in the financial industry, offering clearing and settlement services for options, futures, and securities lending transactions. The company provides a collaborative work environment, competitive benefits, and opportunities for employee growth and development.

Technical Product Manager - Data Platforms

Company: Avant

Location: Chicago IL

Posted Nov 19, 2022

Avant is a high-growth financial technology company looking for a Technical Product Manager to lead their Data Platforms. The company values collaboration, problem-solving, and customer empathy, and offers a range of benefits and perks.

Manager, Financial Planning & Analysis

Company: AdAction

Location: Chicago IL

Posted Nov 17, 2022

AdAction is seeking an experienced FP&A Manager to develop and support corporate financial planning and analysis. The ideal candidate is a creative, analytical, self-starter who thrives in a fast-paced environment and wants to help AdAction transform its FP&A processes.

Product Owner, Marketing

Company: AdAction

Location: Chicago IL

Posted Nov 17, 2022

AdAction is seeking a motivated Product Owner to help drive the product strategy and manage the product development process. The company offers a range of benefits and perks, including health insurance, 401k match, and flexible work schedule.

Social Media Manager

Company: SpotHero

Location: Chicago IL

Posted Nov 17, 2022

SpotHero is a rapidly growing tech company in Chicago that aims to change the parking industry through technology. They are seeking a Social Media Manager to develop and execute a social media strategy that drives business results. The ideal candidate should be proactive, a strong writer, detail-oriented, and creative. SpotHero offers competitive benefits, flexible PTO, and an award-winning culture.

IT Manager

Company: Civis Analytics

Location: Chicago, Illinois, United States

Posted Nov 19, 2022

Civis Analytics is a data science technology company that offers opportunities for newcomers and seasoned professionals. They value creativity, hard work, and on-the-job-excellence and offer competitive compensation and benefits packages. The company is committed to fostering a diverse, equal, and inclusive workplace.

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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