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.

Senior Product Designer

Company: Fetch Rewards

Location: Chicago IL

Posted Sep 25, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. They are looking for a Senior Product Designer to continually push their app's customer experience and Product Design team to new levels.

Senior UI Designer

Company: Fetch Rewards

Location: Chicago IL

Posted Sep 25, 2022

Fetch is a build-first technology company creating a rewards program to power the world. They have grown significantly in the last 5 years and aim to become a global platform transforming how people connect with brands. The company believes in rewarding people for creating value and brands for better connections with customers. They are looking for a Senior UI Designer with extensive mobile experience to join their team.

Head of People Operations

Company: SADA

Location: Chicago IL

Posted Sep 28, 2022

SADA is looking for a Head of People Operations to lead their Human Resources team. The role involves implementing strategic solutions, managing day-to-day activities, and ensuring compliance with laws and regulations. The ideal candidate has experience with scaling internal processes, is hands-on, and thrives under deadlines. The company offers unlimited PTO, paid parental leave, and competitive compensation.

Analytics and Insights - Senior Analyst

Company: Rightpoint

Location: Chicago IL

Posted Sep 27, 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.

Manager, Content Marketing

Company: HealthJoy

Location: Chicago IL

Posted Sep 27, 2022

HealthJoy is a company that offers a simplified benefits experience for employees, with a mission to impact every single one of them. They are a remote-first workplace with a diverse team and offer a range of employee perks and benefits. The company is committed to creating a diverse environment and is proud to be an equal opportunity employer.

UI Designer

Company: Fetch Rewards

Location: Chicago IL

Posted Sep 25, 2022

Fetch is a build-first technology company creating a rewards program to power the world. They have grown from 0 to 18M active users and taken over the rewards game in the US. They believe in rewarding people for creating value and brands for better connections with customers. They are looking for a UI Designer with extensive mobile experience to join their team.

Data Engineer

Company: Veo

Location: Chicago IL

Posted Sep 26, 2022

Veo is a company that offers electric bikes and scooters for sharing, aiming to provide a greener and healthier mode of transportation. They are looking for a Data Engineer to help create an outstanding experience for their riders.

Enterprise Account Coordinator

Company: SpotHero

Location: Chicago IL

Posted Sep 28, 2022

SpotHero is a rapidly growing tech company that aims to bring the parking industry into the future through technology. They offer a unique opportunity to work for a leading e-commerce company with flexible PTO policy, excellent benefits, and a chance to collaborate with creative and innovative people.

Senior Data Product Manager (AI and Platforms)

Company: Kalderos

Location: Chicago IL

Posted Sep 27, 2022

Kalderos is a high-growth company that delivers technology and data solutions to simplify the coordination of drug discount programs in the US healthcare system. They are looking for a seasoned Product Manager to own, define, and execute the roadmap for their data platform, which enables all software products and business functions at Kalderos.

Member Services Specialist

Company: HealthJoy

Location: Chicago IL

Posted Sep 27, 2022

HealthJoy is a company that aims to simplify healthcare benefits for users. They have a talented team and have received awards for being a great place to work. The company is looking for a Marketing Team member to help them continue their high growth and impact.

Distinguished Member of Technical Staff, RF Systems Engineer

Company: Intelsat

Location: Chicago IL

Posted Sep 25, 2022

The job posting is looking for an engineer to work in an innovative and fast-paced group, responsible for developing long-range network planning analysis. The role requires expertise in satellite modems, hub infrastructure architecture, and DVB-S2 and DVB-S2X architecture. The job offers a fun, diverse, and inclusive culture, as well as benefits such as PTO, medical, tuition reimbursement, and training.

Enterprise Architect

Company: Inspire11

Location: Chicago IL

Posted Sep 26, 2022

The text describes a job opportunity at Inspire11, a consulting firm that builds customized solutions for clients. The company offers a collaborative and inclusive work environment, growth opportunities, and a chance to work on exciting projects. The text highlights the firm's commitment to continuous learning, mentorship, and leadership development.

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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