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.

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Company: Kalderos

Location: Chicago, IL

Posted Jan 12, 2023

Kalderos is a company that values collaboration, empowerment, and feedback. They offer a range of benefits and perks, including medical, dental, and vision benefits, 401k with company match, and unlimited PTO. The company is remote-first and has offices in Chicago and Milwaukee.

Software Engineer

Company: FOURKITES

Location: Chicago, IL

Posted Jan 12, 2023

FourKites is a fast-paced, innovative startup looking for a Software Engineer to join their team. The role involves designing, developing, and maintaining their predictive supply chain visibility platform. The company offers a range of benefits, including medical, dental, and vision insurance, 20 PTO days, and ongoing learning and development opportunities.

Systems Support Engineer

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Jan 12, 2023

Keeper is hiring talented System Support Engineers to join their team. The job involves performing technical support for clients and providing resolution analysis on various technical issues. The company offers a range of benefits, including medical, dental, and vision insurance, employer-paid life insurance, and a generous PTO plan.

Employee Experience & Engagement Coordinator

Company: NinjaTrader

Location: Chicago, IL

Posted Jan 11, 2023

The text describes a job role for an Employee Experience & Engagement Coordinator at NinjaTrader. The role involves driving employee engagement and retention, creating programs for employee wellness and development, and planning social events. The primary function of the role is building relationships, and the individual will be required to be onsite for the first 3-6 months. The company offers generous PTO, health benefits, and a gym membership. NinjaTrader is an investor-backed FinTech company that provides software and brokerage services to traders.

Customer Success Manager

Company: FOURKITES

Location: Chicago, IL

Posted Jan 10, 2023

FourKites is a fast-paced, innovative startup looking for a Customer Success Manager to join their team. The role involves building relationships with strategic customers, providing excellent customer experience, and driving value realization. The company offers a range of benefits and opportunities for growth.

Lifecycle Marketing Lead

Company: HealthJoy

Location: Chicago, IL

Posted Jan 12, 2023

HealthJoy is a company that aims to simplify healthcare benefits for users. They are a remote-first employer with a comprehensive benefits package, including medical, dental, and vision insurance, as well as stock options and paid parental leave. The company is committed to equal pay and equal opportunity employment.

Staff Software Engineer

Company: FOURKITES

Location: Chicago, IL

Posted Jan 12, 2023

The job posting is for a Staff Software Engineer position at FourKites, a fast-paced and innovative startup. The role involves working on features end-to-end, developing products, and integrating with strategic partners. The company offers a competitive salary range, benefits, and ongoing learning opportunities.

Senior Associate, FRM Risk Advisory Services

Company: OCC

Location: Chicago, IL

Posted Jan 11, 2023

The job description is for a role that supports the governance, risk, and compliance activities within the Options Clearing Corporation (OCC). The role involves providing advisory services, supporting the design and enhancement of processes and controls, and developing as a subject matter expert. The job requires experience with internal controls, risk assessment strategies, audit techniques, and project management, as well as strong analytical and problem-solving skills.

Strategic Partnerships Sr Associate

Company: Avant

Location: Chicago, IL

Posted Jan 12, 2023

Avant is seeking a strategic partner development team member to work with external partners and internal stakeholders. The role involves developing and refining partnerships, optimizing acquisition pipelines, and driving personal growth. The company values diversity, collaboration, and problem-solving.

Associate, Collateral Services

Company: OCC

Location: Chicago, IL

Posted Jan 12, 2023

The job description is for a Collateral Services position at the Options Clearing Corporation (OCC). The role involves performing accurate transaction processing and activity monitoring, interacting with clearing members and banks, and assisting in the development and maintenance of OCC policies and procedures.

Lifecycle Marketing Lead

Company: HealthJoy

Location: Chicago, IL

Posted Jan 12, 2023

HealthJoy is a company that offers a simplified benefits experience for employees, with a mission to impact every single one of them. They are looking for a Lifecycle Marketing Manager to join their Marketing Team, who will collaborate cross-functionally to build strategy for nurturing customers throughout the buyer journey.

Intern, Accounting

Company: VelocityEHS

Location: Chicago, IL

Posted Jan 10, 2023

VelocityEHS is offering an Accounting internship with valuable business experience, hands-on training, and potential for full-time hours. The intern will work onsite at least once a week at the Global Headquarters in Chicago, IL. Primary duties include daily cash receipts processing, customer database updating, and general office tasks. The ideal candidate is pursuing a related degree, has strong communication skills, and proficiency in Excel. Preferred skills include MS Office proficiency, operational systems experience, and multi-tasking abilities. VelocityEHS is a leading environmental, health, and safety software company offering excellent benefits and a positive work 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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