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.

Sales Development Representative

Company: Atlas

Location: Chicago, IL

Posted Feb 01, 2023

The text describes Atlas, a company that provides Employer of Record (EOR) services, allowing companies to employ people worldwide. The company is looking for a Sales Development Representative to join their team, with a focus on developing key business opportunities and generating qualified prospects.

Enterprise Account Executive

Company: Upwork

Location: Chicago, IL

Posted Jan 31, 2023

Upwork is a remote-first organization that offers a powerful platform for companies and talent to work together. The company is committed to creating economic opportunities and has a diverse and inclusive workforce. The job posting is for an Enterprise Account Executive role that requires a strong business case and strategic thinking.

Manager, Information Technology

Company: HealthJoy

Location: Chicago, IL

Posted Jan 31, 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 401k matching. The company is committed to equal pay and equal opportunity employment.

RevOps Systems Analyst

Company: HealthJoy

Location: Chicago, IL

Posted Jan 31, 2023

HealthJoy is a company that is dedicated to simplifying healthcare benefits for users. They are a remote-first employer and offer a comprehensive benefits package. The company is looking for a RevOps team member to support their sales team and drive greater sales alignment and efficiencies.

Director - Account Management

Company: IPG DXTRA

Location: Chicago, IL

Posted Jan 31, 2023

Golin Chicago is seeking a Director of account management with strategic social/digital expertise to join their dynamic team. The ideal candidate should have experience managing large teams, developing deep client relationships, and extensive social and digital experience. The role involves client counsel, account operations, and managing day-to-day client interactions. The successful candidate will also be expected to lead analytics and measurement teams, develop social-savvy solutions, and collaborate with various teams across disciplines and geographies.

Associate Principal, Privileged Access Management

Company: OCC

Location: Chicago, IL

Posted Jan 31, 2023

The Options Clearing Corporation (OCC) is a leading equity derivatives clearing organization, founded in 1973, dedicated to promoting stability and market integrity. OCC offers a collaborative work environment with benefits like hybrid work, tuition reimbursement, and generous PTO. The Security Engineering role involves automating deployments, managing security products, and applying industry best practices for infrastructure and configuration management. Key responsibilities include working with the Security Engineering team, understanding cloud ecosystems, and consulting with AWS security services. The ideal candidate should have hands-on experience with Python, Ansible, Terraform, Jenkins, and public cloud AWS or Azure/GCP. Preferred skills include HashiCorp Vault, Sysdig, and CyberArk API experience.

Senior Fund Accountant - Work From Home

Company: Epsilon

Location: Chicago, IL

Posted Jan 31, 2023

The job description is for a Senior Fund Accountant at Achieve, a digital personal finance company. The role involves assisting with fund accounting, investor servicing, and financial reporting. The company offers a range of benefits, including hybrid work options, competitive salary, and a positive work environment.

Associate Principal, Software Engineering: UI/UX

Company: OCC

Location: Chicago, IL

Posted Jan 31, 2023

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 for options, futures, and securities lending transactions. 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 has more than 100 clearing members and provides central counterparty (CCP) clearing and settlement services to 19 exchanges and trading platforms. The company offers a highly collaborative and supportive environment, competitive health benefits, and generous PTO and parental leave. The role of a front-end engineer at OCC involves driving front-end engineering practices, designing and developing UI Container Application - Single Client Exterior (SCE), maintaining and communicating CI/CD Pipeline Templates (Jenkins) and Base Images (Docker) for Micro-frontends, and working with the Product team to adopt a Single Client Exterior (SCE) / micro-frontend architecture.

Underwriter I, Commercial Public Management Liability

Company: Argo Group

Location: Chicago, IL

Posted Jan 31, 2023

Argo Group is a leader in specialty insurance with a vibrant culture built on respect, equality, wellness, and opportunity. The company offers a comprehensive benefits package, including flexible workplace policies, comprehensive health and wellness plans, and opportunities for professional development.

Manager - DEI Coordinator

Company: IPG DXTRA

Location: Chicago, IL

Posted Jan 31, 2023

Golin is seeking a Manager - DEI Coordinator to join their Global Diversity Equity & Inclusion team. The role will support various DEI initiatives across the organization, including Golin ERG monthly meetings and global ERG events. The ideal candidate will have project management experience, be deadline driven, and have excellent communication skills.

Senior Business Development Representative - Outbound

Company: Upwork

Location: Chicago, IL

Posted Jan 31, 2023

Upwork, a global work marketplace, is seeking a Business Development Representative to prospect for new business and book sales meetings. The role involves making outbound calls, identifying enterprise opportunities, and achieving weekly and monthly targets. Upwork offers a remote-first culture, competitive benefits, and a commitment to diversity and inclusion.

VP Director, Account Management

Company: IPG DXTRA

Location: Chicago, IL

Posted Feb 01, 2023

Golin Chicago is hiring a savvy VP, Director to lead a fast-paced, industry-leading retail brand. The role involves developing media strategies, counseling clients, and managing a team. The successful candidate will have 10+ years of relevant experience, earned media expertise, and strong hold of the consumer media landscape. The position offers a salary range of $120,000 - $219,000 and is an Equal Opportunity Employer.

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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