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.

Software Engineer III

Company: Vivid Seats

Location: Chicago, IL

Posted Oct 23, 2024

Vivid Seats is a leading online ticket marketplace that aims to connect fans to live events. The company is committed to building products that inspire human connections and has a strong company culture that empowers employees. The role of a Software Engineer II involves making highly visible enhancements to the platform, developing innovative solutions, and working cross-functionally in Agile development teams.

Senior Information Security Engineer

Company: PEAK6

Location: Chicago, IL

Posted Oct 25, 2024

PEAK6 Capital Management is a proprietary options trading firm that has been defining the industry for more than 25 years. They are looking for a skilled Senior Information Security Engineer to strengthen their team in Chicago. The role involves analyzing security measures, ensuring compliance with security standards, and collaborating with teams to build a robust security posture.

Lead Data Warehouse Engineer

Company: Beyond Finance

Location: Chicago, IL

Posted Oct 25, 2024

Beyond Finance is a company that helps people escape debt and achieve financial freedom. They are looking for collaborators to help them grow and are offering a range of benefits and opportunities for professional development.

Principal, Quality Assurance

Company: OCC

Location: Chicago, IL

Posted Oct 24, 2024

The QA Principal drives the testing tool strategy and orchestration, and works closely with development and test teams to meet quality objectives. The role involves designing and developing software testing tool frameworks, implementing best practices, and optimizing existing automation frameworks.

Procurement Manager

Company: PEAK6

Location: Chicago, IL

Posted Oct 26, 2024

PEAK6 is a leading investment firm that uses technology to find a better way of doing things. They are seeking a dynamic Procurement Manager to lead the strategic sourcing of technology and indirect categories.

Associate, Data Engineer

Company: Avant

Location: Chicago, IL

Posted Oct 26, 2024

Avant is looking for an Associate Data Engineer to build and evolve their data model. The role requires expertise in SQL, data modeling, and data engineering. The company values diversity, collaboration, and problem-solving, and offers a range of benefits and perks.

CashNetUSA Application Support Representative (Remote)

Company: Enova

Location: Chicago, IL

Posted Oct 23, 2024

The job posting is for an Application Support Representative role at Enova International, a leading financial technology company. The role involves handling inbound calls, assisting customers with loan applications, and converting prospects into sales. The company offers a range of benefits and perks, including hybrid work arrangements, health insurance, and a sabbatical program.

Director, Digital Solutions Strategy

Company: iRhythm Technologies, Inc.

Location: Chicago, IL

Posted Oct 23, 2024

iRhythm is a leading digital healthcare company that creates trusted solutions to detect, predict, and prevent disease. The company is seeking a Director of Digital Solutions Strategy to lead their Digital Strategy Partners team and drive innovative process improvement initiatives.

Manager of Implementation

Company: Hireology

Location: Chicago, IL

Posted Oct 22, 2024

Hireology is a market-leading organization with an award-winning culture, offering unlimited paid time off, health insurance, and more. The company is committed to equal employment opportunities and supports an inclusive workplace.

Sr. Software Engineer (Perm - Hybrid or Remote)

Company: Alliant Credit Union

Location: Chicago, IL

Posted Oct 25, 2024

The job description outlines the responsibilities and requirements for an application development project manager. The role involves designing, developing, and implementing projects, as well as analyzing business needs and developing software solutions. The job also requires project management skills, technical knowledge, and the ability to work with other technical support functions.

Associate, Fraud Analytics

Company: Avant

Location: Chicago, IL

Posted Oct 25, 2024

Avant is looking for knowledgeable fraud professionals to join their Fraud Operations team in Chicago. The job involves developing and implementing fraud rules, analyzing data, and communicating results to stakeholders. The company offers a range of benefits, including flexible work environment, unlimited paid time off, and access to LinkedIn Learning.

Principal Site Reliability Engineer

Company: iManage

Location: Chicago, IL

Posted Oct 24, 2024

iManage is a company that values collaboration, learning, and growth. They offer a flexible working policy, a supportive team, and opportunities for professional development. The company is committed to building a diverse and inclusive environment and encourages employees to bring their authentic selves to work.

Frequently Asked Questions

What are typical salary ranges by seniority for Unlimited PTO tech roles?
Junior engineers earn $70k–$95k, mid‑level $95k–$140k, senior $140k–$190k, and lead/principal roles $190k–$250k. Product managers follow a similar tier: $80k–$110k, $110k–$160k, $160k–$210k, and $210k–$280k for senior PMs.
What skills and certifications are required for Unlimited PTO positions?
Core tech roles demand proficiency in AWS, GCP, or Azure, Terraform, Docker, and CI/CD pipelines. Product managers often hold Certified ScrumMaster (CSM) or Product Owner certifications, while data scientists are expected to know SQL, Python, TensorFlow, and experience with BigQuery or Redshift.
Is remote work common for Unlimited PTO jobs?
Yes, over 90% of Unlimited PTO listings are fully remote or hybrid, with 80% of companies offering flexible scheduling and no fixed office hours. Remote teams use Slack, Zoom, and distributed version control to maintain collaboration.
What career progression paths exist within Unlimited PTO companies?
Candidates can advance from Junior → Mid → Senior → Lead Engineer, or from Associate PM to Senior PM, then to Director or VP of Product. Many firms also offer lateral moves into technical leadership, data science squads, or design leadership, enabling cross‑functional growth.
What industry trends affect Unlimited PTO roles?
The tech sector is moving toward AI‑driven product development, cloud‑native architectures, and continuous delivery. Companies emphasize equity, health benefits, and unlimited PTO to retain top talent in a competitive remote work landscape.

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