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.

Strategic Pricing Coordinator

Company: MoLo Solutions

Location: Chicago, IL

Posted Mar 01, 2023

The Strategic Pricing Coordinator will support the Yield department in managing RFPs, bids, and pricing requests. They will format customer RFPs into internal bid files, analyze supporting documents for accurate setup and pricing, and maintain the status update for each RFP in the tracking tool. The role requires 1 year of third-party logistics industry experience, strong organizational skills, and proficiency in basic computer skills, including Microsoft Office and Excel.

Associate Product Designer

Company: SpotHero

Location: Chicago, IL

Posted Mar 01, 2023

SpotHero is a rapidly growing startup that connects parking operators with drivers through a mobile app or website. They offer a full-stack product design team and are looking for an Associate Product Designer to work on the core garage-facing product. The role involves working with a senior designer, product manager, and engineering manager to create the best pricing strategy, facility management, and reporting tools. The company offers a competitive benefits package, flexible PTO, and a learning budget. They have a strong focus on diversity and inclusion.

Senior Associate, Software Engineering: UI/UX

Company: OCC

Location: Chicago, IL

Posted Mar 01, 2023

The role involves driving the front-end vision across all product engineering teams at OCC, working with Product team UI Devs in adopting a Single Client Exterior (SCE) / micro-frontend architecture, building on OCC's Design System using ReactJS and Figma, championing reusability, best practice component design & execution, and accessibility (a11y), engaging security engineering for testing and compliance, and continually learning emerging technologies/industry trends.

Social Media Specialist

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Feb 28, 2023

Keeper Security, Inc. is seeking a dynamic Social Media Specialist to join their global communications team and grow their brand awareness through various social media outlets. This is a 100% remote position with a fast-growing cybersecurity company offering competitive benefits and a positive work environment. The ideal candidate will have proven work experience in social media, in-depth knowledge of social media platforms, and the ability to create and execute creative content.

Manager, Internal Audit Information Technology & Security

Company: OCC

Location: Chicago, IL

Posted Mar 01, 2023

The Options Clearing Corporation (OCC) is a leading organization in the world, providing central counterparty clearing and settlement services. The company offers a collaborative and supportive environment, competitive benefits, and opportunities for employee growth. The role of the Internal Audit Manager is to manage independent assessments of OCC's Information Technology and Security environment, risk management, and other objectives.

Lead Contract Pricing Engineer

Company: MoLo Solutions

Location: Chicago, IL

Posted Mar 01, 2023

The job description for the Lead Contract Pricing Engineer at MoLo requires identifying and facilitating bid-specific strategies, working with the RFP Execution Manager and Strategic Pricing Coordinator, engaging with the yield team and customer teams, and managing the account-specific execution of RFPs. The role requires a minimum of 2 years of third-party logistics truckload experience and 1 year of truckload pricing experience. MoLo offers a casual and fun start-up culture, transparent leadership, industry training, and comprehensive benefits.

Senior Environmental Underwriter

Company: Argo Group

Location: Chicago, IL

Posted Feb 28, 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 line of high-quality products and services designed to meet the unique coverage and claims-handling needs of its clients.

Chief of Staff

Company: Cameo

Location: Chicago, IL

Posted Feb 28, 2023

Cameo is a global platform that allows fans to get personalized video messages and merchandise from their favorite stars and creators. The company values creativity, hard work, collaboration, and direct dialogue. They are looking for a Chief of Staff to partner with the CEO and COO on the strategy and operational cadence of the business.

Associate Principal, Privileged Access Management

Company: OCC

Location: Chicago, IL

Posted Mar 01, 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. As a Security Engineering member, you'll automate deployment and management of security products within AWS infrastructure, applying industry best practices for DevSecOps, configuration management, and Infrastructure-as-code. Key responsibilities include working with the Security Engineering team, understanding cloud ecosystems, and consulting with AWS security services. Required skills include 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.

Sales Development Representative

Company: LogicGate

Location: Chicago, IL

Posted Mar 01, 2023

LogicGate is a company that aims to transform business risks into opportunities through a modern risk management platform. They are an outcomes-first company with a focus on diversity and inclusion. They have been recognized as a top workplace by several reputable organizations. The company offers a flexible and no-code risk management solution and is committed to fostering an inclusive work environment.

Project Engineer I

Company: SpotHero

Location: Chicago, IL

Posted Feb 28, 2023

The text describes a Project Engineer I position at SpotHero, a parking reservation service. The role involves developing solutions for operational functions, creating business process automations, designing and developing new internal tools, building data pipelines, and ensuring system maintenance. The ideal candidate should have programming experience, particularly in JavaScript and SQL, and be familiar with REST APIs and JWT. The company offers a career game changer, excellent benefits, flexible PTO, and a workplace recognized for its culture and work environment.

Lead Contract Pricing Engineer

Company: MoLo Solutions

Location: Chicago, IL

Posted Mar 01, 2023

The job description for the Lead Contract Pricing Engineer at MoLo requires managing RFP execution, collaborating with teams, and ensuring effective communication of pricing strategies. The role demands a minimum of 2 years of third-party logistics truckload experience and 1 year of truckload pricing experience. The company offers a casual culture, industry training, and competitive salary with a commission structure.

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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