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.

Chief Information Security Officer (CISO)

Company: Halo Investing

Location: Chicago IL

Posted Nov 08, 2022

Halo Investing is a fintech company that provides a platform for defined outcome investing. They are looking for a Chief Information Security Officer to join their team and help define and execute security strategies.

Director of Enterprise Sales

Company: Halo Investing

Location: Chicago IL

Posted Nov 08, 2022

Halo Investing is a FinTech company that provides a platform for defined outcome investing. They have raised over $100 million in funding and are changing the world of investing by democratizing the protective investment marketplace.

Client Services Representative

Company: OCC

Location: Chicago IL

Posted Nov 07, 2022

The Options Clearing Corporation (OCC) is the world's largest equity derivatives clearing organization, dedicated to promoting stability and market integrity by delivering clearing and settlement services. As a Systemically Important Financial Market Utility (SIFMU), OCC operates under the jurisdiction of the U.S. Securities and Exchange Commission (SEC), the U.S. Commodity Futures Trading Commission (CFTC), and the Board of Governors of the Federal Reserve System. OCC provides central counterparty (CCP) clearing and settlement services to 19 exchanges and trading platforms, offering a highly collaborative and supportive environment with competitive benefits and a hybrid work environment.

Creative Copywriter (Remote)

Company: Bump Boxes

Location: Chicago IL

Posted Nov 10, 2022

Bump Health is a women's health brand that is profitable, growing, and privately held. They are looking for a creative copywriter to join their marketing team and craft copy for their key marketing channels.

Campaign Insights Manager

Company: InMarket

Location: Chicago IL

Posted Nov 08, 2022

InMarket is seeking a creative and data-driven Campaign Insights Manager to join their Insights team. The role involves partnering with various internal teams to deliver insightful, elegant, and actionable data to clients. The Campaign Insights Manager must have excellent communication skills, flawless time management, and be able to operate in a fast-paced environment with strict deadlines.

Marketing Copywriter (Remote)

Company: Bump Boxes

Location: Chicago IL

Posted Nov 10, 2022

Bump Health is a women's health brand that is profitable, growing, and privately held. They are looking for a marketing copywriter to join their team and help them craft the copy for their marketing channels. The company has a great product in a market with incredible demand and wants the copywriter to make a big impact on the performance of their marketing campaigns.

Business Analyst

Company: OCC

Location: Chicago IL

Posted Nov 09, 2022

The job description is for a Senior Associate position in the Business Engineering & Strategy team at the Options Clearing Corporation (OCC). The role involves working on high-priority improvement initiatives, leading project management, and developing agile user stories. The team is responsible for delivering human-centric design solutions and improving business processes through automation.

Mid-Market Sales Manager

Company: Atlas

Location: Chicago IL

Posted Nov 08, 2022

The text describes Atlas, a company that simplifies global expansion for businesses. It highlights the company's mission, technology, and benefits, including a diverse and inclusive environment, flexible PTO, and growth opportunities.

Fraud Operations, Analyst

Company: Avant

Location: Chicago IL

Posted Nov 08, 2022

Avant is looking for knowledgeable fraud professionals to join their Fraud Operations team in Chicago. The job involves reviewing and remediation of escalations, supporting investigations, and communicating with stakeholders. The company values diversity, collaboration, and problem-solving, and offers great benefits and perks.

Regional Vice President

Company: Halo Investing

Location: Chicago IL

Posted Nov 08, 2022

Halo Investing is a financial technology company that provides a platform for defined outcome investing. The company has received recognition for its innovative approach and has raised over $100 million in funding. It is based in Chicago and has offices in Zurich and Abu Dhabi.

Head of Enterprise Sales

Company: Halo Investing

Location: Chicago IL

Posted Nov 08, 2022

Halo Investing is a FinTech company that provides a platform for defined outcome investing. They have raised over $100 million in funding and are looking for a Head of Enterprise Sales to lead their sales team.

Fraud Operations, Analyst

Company: Avant

Location: Chicago IL

Posted Nov 08, 2022

Avant is seeking knowledgeable fraud professionals to join their Fraud Operations team in Chicago. The role involves supporting real-time escalations, offline analysis of emerging threat vectors, and communication of investigation details. The team collaborates with various internal stakeholders to identify emerging threats and communicate findings to business leaders. The position requires a Bachelor's degree or 2+ years of experience in fraud analysis, proficiency in Microsoft Office and SQL, and strong communication skills.

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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