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.

Partner Development Manager, Retail

Company: Fetch Rewards

Location: Chicago IL

Posted Aug 13, 2022

Fetch is a build-first technology company creating a rewards program to power the world. They have grown from 0 to 17M active users and taken over the rewards game in the US. They aim to become a global platform that transforms how people connect with brands. The company believes in rewarding people for creating value and brands for having a direct connection with customers. They are looking for a Partner Development Manager to support their valued partnership with Albertsons - Jewel-Osco Division.

Manager, Pricing

Company: MoLo Solutions

Location: Chicago IL

Posted Aug 13, 2022

MoLo is a logistics company that is looking for a Manager of Pricing to manage a team of Strategic Pricing Analysts. The job requires experience in truckload brokerage, pricing strategy, and team leadership. The company offers a casual and fun start-up culture, transparent leadership, and opportunities for growth and advancement.

Retention Marketing Manager

Company: AdAction

Location: Chicago IL

Posted Aug 13, 2022

AdAction is a performance marketing company that values its employees and offers a range of benefits and perks. The company is looking for a Retention Manager to develop and execute marketing strategies to drive subscriber growth and retention.

Product Counsel

Company: Argo Group

Location: Chicago IL

Posted Aug 13, 2022

Argo Group is a leader in specialty insurance with a vibrant culture and a commitment to employee well-being and development. The company offers a range of benefits and opportunities for growth and advancement.

Payroll and HRM Supervisor

Company: Renovo Financial

Location: Chicago IL

Posted Aug 13, 2022

Renovo Financial is a rapidly growing Chicago-based private lender seeking a Payroll/HRMS Supervisor to support clients with unparalleled service. The ideal candidate has experience with ADP payroll service, HRM, and benefits administration, and is local to the Chicagoland area.

Principal Data Engineer

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 12, 2022

The job posting is looking for a Data Management professional to join their team in designing and delivering solutions for big data analytics. The role requires experience with cloud-based services, programming languages, and data processing. The company emphasizes personal and professional growth, diversity, and inclusivity.

IT Support Technician

Company: HealthJoy

Location: Chicago IL

Posted Aug 13, 2022

HealthJoy is a company that offers a unique healthcare benefits experience, using industry-leading technology to simplify benefits for users. They have experienced explosive growth and have received several awards for their HR technology and workplace culture. The company offers a range of employee perks and benefits, including healthcare benefits, flexible PTO, and parental leave.

Regional Sales Director

Company: WorkBoard Inc.

Location: Chicago IL

Posted Aug 14, 2022

WorkBoard is a company that provides a results platform to help companies achieve their growth plans. The company is looking for a Regional Sales Director to drive the adoption of their platform within a defined geography. The job requires experience in C-Suite business application value-based selling and start-up experience.

Customer Success Manager - Manufacturing

Company: Kalderos

Location: Chicago IL

Posted Aug 13, 2022

Kalderos is a company that builds unifying technologies to bring transparency, trust, and equity to the healthcare community. They are looking for a Customer Success Manager-Manufacturing to help ensure customers have a positive experience through excellent customer service and process improvement. The company values collaboration, empowerment, and continuous growth and development.

Sr. Analyst, Collections Strategy

Company: Avant

Location: Chicago IL

Posted Aug 13, 2022

Avant is hiring for a Collections Strategy team member. The job requires analyzing large datasets, delivering insights, and recommending business plan updates. The company values authenticity, collaboration, and problem-solving, and offers a range of benefits and perks.

Security Operations Engineer

Company: HealthJoy

Location: Chicago IL

Posted Aug 13, 2022

HealthJoy is a company that offers a unique healthcare benefits experience, using industry-leading technology to simplify the process. They have experienced explosive growth and have received several awards for their work. The company values its employees, offering a robust package of employee perks and benefits, and is committed to creating a diverse environment.

Carrier Sales Representative (Shift: 10:00am-7:00pm)

Company: MoLo Solutions

Location: Chicago IL

Posted Aug 13, 2022

MoLo is a logistics company that offers a casual and fun start-up culture, transparent leadership, and opportunities for growth and internal advancement. The company is looking for Carrier Sales Representatives to join their Pit Crew team, who will be responsible for supporting same day, next day, and after-hours load coverage.

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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