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.

Data Engineer

Company: Aquatic Capital Management

Location: Chicago IL

Posted Dec 20, 2022

Aquatic Capital is a quantitative trading and investment company, founded by Jon Graham, seeking a Data Engineer for their Chicago or New York office. The role involves onboarding new data sources, working with vendors, and optimizing queries. The base salary is between $150,000 and $300,000, with additional compensation and benefits available. The company culture is collaborative, meritocratic, and ambitious.

Customer Service Representative

Company: Traffic Tech

Location: Chicago IL

Posted Dec 19, 2022

Traffic Tech is a leading logistics company seeking an entry-level Customer Service Representative to join their Team Mexico. The role involves coordinating freight movement, building vendor relationships, and providing excellent customer service. The company offers competitive benefits, training, and mentorship opportunities.

Technical Program Manager

Company: Fetch

Location: Chicago IL

Posted Dec 19, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. They believe people deserve to be rewarded when they create value and brands need a better connection with their customers. They offer a range of benefits and a hybrid work environment.

DAS Field Engineer

Company: Boingo Wireless

Location: Chicago IL

Posted Dec 19, 2022

Boingo Wireless is looking for a highly energetic and customer-focused person to join their Operations Team. The role involves improving and maintaining system performance in existing large-scale venues in the Chicago area. The company offers competitive pay, quarterly bonuses, and great health insurance.

Customer Success Manager

Company: Evolv Technology

Location: Chicago IL

Posted Dec 22, 2022

Evolv is looking for Customer Success Managers to build lasting relationships with customers, ensure they derive maximum value from their investment, and drive customer satisfaction and subscription renewals. The role involves developing success plans, managing activities related to product consumption, and escalating risks and issues to management. The team is distributed across the US, with most members working remotely, and the role is located in the Midwest region.

Associate Principal, Enterprise Project Management Office

Company: OCC

Location: Chicago IL

Posted Dec 19, 2022

The job description is for a project manager role at OCC, a leading equity derivatives clearing organization. The role involves driving projects from initiation to closure, leading project planning and execution, and ensuring high-quality outcomes. The job requires advanced project management skills, analytical problem-solving, and excellent communication skills.

Principal Enterprise Security Engineer -Cloud Focus

Company: Halo Investing

Location: Chicago IL

Posted Dec 19, 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 an Enterprise Security Engineer to join their team.

Business Development Representative

Company: Upwork

Location: Chicago IL

Posted Dec 19, 2022

Upwork is a remote-first organization that provides a 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 a Business Development Representative who will prospect for new business and work closely with a team to generate leads and book sales meetings.

White Label Account Executive

Company: Paro

Location: Chicago IL

Posted Dec 21, 2022

Paro is seeking an Account Executive to join their 'White Label' team, focusing on outbound sales to professional services firms. The role involves building relationships, acquiring new partners and clients, and expanding the client portfolio.

Chief Technology Officer

Company: SpotHero

Location: Chicago IL

Posted Dec 20, 2022

SpotHero is a parking solution company that is changing the way drivers park daily. They have a strong board, partnerships with major companies, and a focus on innovation and customer experience. They are seeking a Chief Technology Officer to lead their engineering team and drive company strategy.

Senior Product Designer

Company: Halo Investing

Location: Chicago IL

Posted Dec 19, 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 Senior Product Designer to help shape their user research practice.

Senior Engineer, Backend (Operator League-Integrations)

Company: SpotHero

Location: Chicago IL

Posted Dec 19, 2022

SpotHero is looking for Staff Backend Engineers to join the Operator League for the Integrations Squad. The role involves building services that make Drivers' experience seamless as they enter each Facility. The ideal candidate should have over five years of engineering experience, worked for multiple companies as a software engineer, and have strong coding skills and system design/architecture capabilities. The candidate should be able to collaborate with management, work with the Product Management team, and be an educator and mentor to others. The company offers a unique experience to work for a fast-growing startup with excellent benefits, flexible PTO, and a casual yet highly productive atmosphere.

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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