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.

Director of Analytics & Insights

Company: Rightpoint

Location: Chicago IL

Posted Sep 03, 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 flexible work environment, great insurance coverage, and opportunities for continuous learning and growth.

Solutions Engineer

Company: Checkr

Location: Chicago IL

Posted Sep 05, 2022

Checkr is a technology company that aims to create a fairer future by designing technology to create opportunities for all. The company is committed to hiring talented individuals with diverse backgrounds and has been recognized for its commitment to diversity and inclusion.

Principal, Software Release Test Engineer

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Sep 06, 2022

The job posting is looking for a Principal, Software Release Test Engineer to work with Intelsat Inflight, the inflight internet company. The role involves creating and maintaining automated and manual testing endeavors, working with developers and other departments to define and influence product performance, and mentoring others on test techniques. The company emphasizes personal and professional growth, has awesome benefits, and a fun and diverse culture.

UX Designer

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Sep 04, 2022

Intelsat Inflight is looking for a UX Designer to join their team. The role involves designing passenger-facing in-air web portal and tools, conducting research, and collaborating with other designers, product managers, and engineers. The company emphasizes personal and professional growth, offers great benefits, and has a fun and inclusive culture.

Data Scientist

Company: Inspire11

Location: Chicago IL

Posted Sep 03, 2022

The text describes Inspire11, a company that values collaboration, authenticity, and diversity. They believe in empowering their team members to drive change and take ownership of their careers. The company culture is vibrant and light-hearted, with a focus on work-life balance and individualized professional growth.

Adobe Experience Manager (AEM) Architect - (Hoodoo Digital)

Company: Rightpoint

Location: Chicago IL

Posted Sep 04, 2022

Rightpoint, a digital consultancy, has joined forces with Hoodoo Digital to expand its capabilities in content, commerce, and marketing operations. The company is looking for talented individuals to join its team and create innovative customer experiences.

Engineer, Aircraft Fleet Support

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Sep 03, 2022

The job posting is for a fleet support team leader at Intelsat, a company that connects the world and transforms the satellite and inflight connectivity landscape. The role involves troubleshooting and resolving issues with Intelsat airborne systems, working closely with various teams, and mentoring and guiding team members. The company emphasizes personal and professional growth, has awesome benefits, and a fun, diverse, and inclusive culture.

SaaS Market Manager

Company: Booksy

Location: Chicago IL

Posted Sep 04, 2022

The job description is for an outside sales team member at Booksy, a company that values hiring the right people with the right intentions. The job involves building relationships with clients, conducting demos, and growing the business. The company offers a range of benefits and a creative and collaborative culture.

Principal Engineer, Systems

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Sep 03, 2022

The job posting is for a Principal Systems Engineer at Intelsat, a company that connects the world and transforms the satellite and inflight connectivity landscape. The role involves developing and producing new system architectures, defining technical requirements, and working with cross-functional teams. The company emphasizes personal and professional growth, has awesome benefits, and a fun, diverse, and inclusive culture.

Visual Design Lead/Product Design Lead

Company: Rightpoint

Location: Chicago IL

Posted Sep 03, 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 flexible work environment, great insurance coverage, and opportunities for continuous learning and growth.

Business Intelligence Developer

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Sep 04, 2022

The job posting is for a Business Intelligence professional to join Intelsat's Commercial Aviation division. The role involves designing and delivering solutions for big data analytics, working with a dynamic and innovative team, and utilizing a rigorous design methodology. The company emphasizes personal and professional growth, has awesome benefits, and a fun, diverse, and inclusive culture.

People Operations Coordinator - Part-time/Contract

Company: HealthJoy

Location: Chicago IL

Posted Sep 06, 2022

HealthJoy is a company that offers an innovative technology solution to simplify healthcare benefits, making them more accessible and affordable for users. The company has experienced significant growth, including raising $30M in Series C funding and earning awards for its best HR technology leaders. HealthJoy is committed to creating a welcoming and inclusive company culture, with a focus on supporting the overall employee experience. The company offers a robust package of employee perks and benefits, including healthcare benefits, flexible PTO, 401k+match, parental leave, and HSA contribution match. HealthJoy is an equal opportunity employer and is committed to creating a diverse 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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