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.

Senior Staff / Principal Engineer

Company: SpotHero

Location: Chicago IL

Posted Aug 11, 2022

SpotHero is looking for Principal/Senior Staff Engineers with over twelve years of experience in engineering, worked for multiple companies, and is an expert or polymath in Software Engineering. The role involves collaborating with management, contributing to the codebase, providing support for any part of the codebase, and working with the Product Management team. The company values humility, a strong work ethic, flexibility, collaboration, technical curiosity, and constant learning. They have a tech stack that includes Python/Django, Kotlin, GoLang, JavaScript/TypeScript/React, iOS Swift, Kotlin in Android, and more. They use various tools and services like Bitrise, Dagger, RxJava, Espresso, Retrofit, Fastlane, Sentry, Docker, Kubernetes, .Net CORE, and more. They offer excellent benefits, a flexible PTO policy, and a workplace recognized for its culture and work environment.

Advisor, Customer Operations

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 12, 2022

The Advisor, Customer Operations role at Intelsat is responsible for ensuring customer satisfaction with Inflight Entertainment and Connectivity (IFEC). The role involves being the primary liaison between key airline customers and internal operational groups, driving key metrics, and participating in the development of a comprehensive automated alerting mechanism. The role requires strong communication skills, business acumen, and the ability to solve complex problems.

Principal Software Engineer

Company: Avant

Location: Chicago IL

Posted Aug 11, 2022

AvantDeliver is looking for experienced engineers to work on high-quality software applications. The company values collaboration, problem-solving, and customer satisfaction. It offers a flexible growth environment, great perks, and benefits.

Sr. Technical Writer

Company: Intelsat (formerly Gogo)

Location: Chicago IL

Posted Aug 12, 2022

The job requires organizing, writing, and publishing maintenance documentation, and working in a dynamic environment. The company emphasizes personal and professional growth, and offers benefits and a fun, diverse culture.

Designer, Brand

Company: Kalderos

Location: Chicago IL

Posted Aug 10, 2022

Kalderos is a company that is building unifying technologies to bring transparency, trust, and equity to the healthcare community. They are looking for a Designer, Brand to join their team and contribute to building their visual identity system and institutional storytelling.

Strategic Account Executive

Company: Paro

Location: Chicago IL

Posted Aug 09, 2022

Paro is a company that empowers business professionals to pursue meaningful work on their own terms. They provide flexible finance and accounting solutions to businesses through a network of freelance experts. The company is looking to add a Strategic Account Executive to their team, responsible for acquiring new clients and expanding their client portfolio.

Technical Support Specialist

Company: Baird & Warner

Location: Chicago IL

Posted Aug 09, 2022

Baird & Warner Real Estate is a company that values its employees and provides them with the support they need to grow in their careers. The company has a strong culture and is committed to making its team feel part of something bigger.

Public Sector Marketing Manager

Company: Keeper Security, Inc.

Location: Chicago IL

Posted Aug 12, 2022

Keeper Security is hiring a Public Sector Marketing Manager to join their team. The ideal candidate will have experience in Public Sector marketing, account-based marketing techniques, and be conversant in modern demand generation techniques.

Claims Specialist

Company: MoLo Solutions

Location: Chicago IL

Posted Aug 10, 2022

The job description is for a Claims Specialist role at MoLo, a logistics company. The job involves investigating and resolving cargo claims, negotiating settlements, and collaborating with internal and external teams. The company offers a casual and fun start-up culture, extensive training, and opportunities for growth and advancement.

Technical Product Manager - Data Platforms

Company: Avant

Location: Chicago IL

Posted Aug 11, 2022

Avant is a high-growth financial technology company looking for a Technical Product Manager to lead their Data Platforms. The company values collaboration, problem-solving, and customer empathy, and offers a range of benefits and perks.

Software Engineer, Deposits Platform Team

Company: Avant

Location: Chicago IL

Posted Aug 11, 2022

The job posting is for a DevOps/SRE role at Avant, a company that values diversity, collaboration, and problem-solving. The job involves developing tools and infrastructure to support customer-facing products, and requires strong development experience and prior success in enabling effective partnerships.

Executive Assistant to C-Suite

Company: Inspire11

Location: Chicago IL

Posted Aug 11, 2022

Inspire11 is a team of passionate and collaborative individuals who believe in driving change and taking ownership of their careers. They partner with clients to define strategies and optimize their business in data and digital. The company values individualized professional growth, work-life balance, and a vibrant company culture.

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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