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.

People Operations Lead

Company: HealthJoy

Location: Chicago, IL

Posted Jan 19, 2023

HealthJoy is a company that aims to simplify healthcare benefits for users. They are a remote-first company with a mission to impact every single one of their employees. The company is looking for a People Operations & Total Rewards professional to join their team.

Controller

Company: SpotHero

Location: Chicago, IL

Posted Jan 23, 2023

None Found

Software Engineer II: Front End

Company: LogicGate

Location: Chicago, IL

Posted Jan 20, 2023

LogicGate is a company that values diversity, inclusivity, and growth. They offer a range of benefits and perks to their employees, including competitive salaries, variable compensation, equity, and comprehensive total rewards packages. The company also prioritizes career development and learning opportunities, and has a strong focus on giving back to the community.

Product Specialist for Health Tech Startup, Customer Success

Company: CancerIQ

Location: Chicago, IL

Posted Jan 19, 2023

CancerIQ is a healthcare technology company that enables providers to recognize and manage patients with increased cancer risk at scale. The company's mission is to engage and educate patients using cutting-edge technologies for cancer prevention. CancerIQ is seeking a Product Specialist, an entry-level customer-facing role, to work with the Customer Success Manager to ensure smooth operation of CancerIQ customer sites, meet key performance metrics, and provide ongoing support. The Product Specialist will deliver training, attend customer calls, build trust with clinical staff, develop product expertise, and assist with research and marketing materials. The role requires a Bachelor's degree, preferably in Life Sciences, Business, or Health Administration, experience in healthcare, strong organization skills, excellent communication skills, and proficiency in Microsoft Office Suite. Travel is estimated at 20% for on-site customer meetings. CancerIQ offers competitive benefits, a passionate culture, unlimited PTO, and a commitment to diversity and inclusion.

Principal, Software Engineering: Software Development Test (SDET)

Company: OCC

Location: Chicago, IL

Posted Jan 19, 2023

The job posting is for a Principal, Software Engineering: Software Development Test (SDET) position at the Options Clearing Corporation (OCC). The role involves leading manual and automated integration testing, developing test plans, and working with product teams to resolve issues. The job requires strong testing and QA automation background, technical skills, and experience in financial services or capital markets.

Compliance Analyst

Company: HealthJoy

Location: Chicago, IL

Posted Jan 23, 2023

None Found

Software Engineer III: Front End

Company: LogicGate

Location: Chicago, IL

Posted Jan 19, 2023

LogicGate is a company that values diversity, inclusivity, and growth. They offer a competitive total rewards package, flexible work arrangements, and opportunities for career development. The company is committed to fostering a culture of belonging and giving back to the community.

People Operations Lead

Company: HealthJoy

Location: Chicago, IL

Posted Jan 19, 2023

None Found

Systems Support Engineer (2nd Shift)

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Jan 19, 2023

Keeper Security is hiring talented System Support Engineers for a 100% remote position. The role involves working on complex technical issues and resolution analysis. The company is a leading provider of zero-trust and zero-knowledge security cloud services, with high ratings and certifications. The job requires a customer service mindset, IT management experience, and hands-on experience with various systems. The company offers benefits such as medical, dental, and vision insurance, 401k, and PTO.

Business Analyst (IT)

Company: SpotOn

Location: Chicago, IL

Posted Jan 23, 2023

None Found

Senior Manager, Org & People

Company: West Monroe

Location: Chicago, IL

Posted Jan 19, 2023

West Monroe's Org & People practice is seeking a Senior Manager with at least 8 years of HR experience, preferably in a client-facing strategy or advisory role. The role involves serving as a delivery leader on engagements, overseeing project scope, budget, deliverables, and team development. The ideal candidate should have expert program management skills, business development experience, and strong communication and data visualization skills. West Monroe is committed to inclusion and diversity, offering competitive rewards and benefits.

Enterprise Application Support Engineer

Company: Enfusion

Location: Chicago, IL

Posted Jan 20, 2023

None Found

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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