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 Engineer, Front End

Company: SpotHero

Location: Chicago, IL

Posted Jan 08, 2023

SpotHero is seeking a Senior Front End Engineer to work on their flagship consumer products. The company values teamwork, humility, and constant learning, and offers excellent benefits, flexible PTO, and a unique experience to work for a fast-growing startup.

Manager, Information Technology

Company: HealthJoy

Location: Chicago, IL

Posted Jan 06, 2023

HealthJoy is a remote-first workplace with a mission to simplify healthcare benefits. They have raised over $100M in funding and offer a comprehensive package of employee perks and benefits. The company is looking for an IT Manager to lead a team in creating new experiences to deliver Joy to their members.

Senior Environmental Underwriter

Company: Argo Group

Location: Chicago, IL

Posted Jan 09, 2023

Argo Group is a leader in specialty insurance with a vibrant culture that values respect, equality, wellness, and opportunity. They are an innovative organization that is flexible and agile, with a focus on creating a comfortable, respectful, and equal workplace. The Environmental Division is looking for a Senior Underwriter to write new and renewal Package and/or Casualty business within the Environmental Division. The successful candidate will have a bachelor's degree in environmental science, engineering, geology, or a related field, as well as environmental consulting experience. They will also need strong communication skills, attention to detail, and the ability to work independently in a fast-paced environment. The company offers a comprehensive benefits package, including competitive compensation, health and wellness options, and paid time off.

Senior Program Manager - Enterprise Program Success

Company: Upwork

Location: Chicago IL

Posted Jan 06, 2023

Upwork is a remote-first organization that provides a platform for companies and talent to work together. The company is committed to diversity and inclusion, and offers a range of benefits to its employees.

Senior Accountant

Company: SpotHero

Location: Chicago, IL

Posted Jan 09, 2023

SpotHero is seeking a Senior Accountant to drive day-to-day accounting and financial processes. The role involves creating journal entries, preparing balance sheets, and working with various departments. The company offers excellent benefits, flexible work arrangements, and a unique experience working for a fast-growing startup.

Sales Enablement Manager

Company: SpotHero

Location: Chicago IL

Posted Jan 07, 2023

SpotHero is a rapidly growing tech company that aims to bring the parking industry into the future through technology. They offer a unique opportunity to work in a dynamic environment, with a focus on creating space for life. The company values inclusivity, diversity, and work-life balance, and offers excellent benefits and a competitive salary.

Associate Principal, Windows Services

Company: OCC

Location: Chicago IL

Posted Jan 07, 2023

The job posting is seeking a Windows server engineer to administer and enhance the Windows server infrastructure. The successful candidate must have prior experience designing, supporting and administering Windows server environment. The job requires excellent people skills, strong analytical and technical skills for trouble shooting complex issues.

Associate Principal, Site Reliability Engineering

Company: OCC

Location: Chicago IL

Posted Jan 07, 2023

The job description is for a Site Reliability Engineer/DevOps position at the Options Clearing Corporation. The role involves supporting the availability and performance of the company's cloud platform, collaborating with development and operations teams, and providing guidance on cloud technologies and application profiling.

Carrier Sales Representative (Shift: 1:00pm-10:00pm)

Company: MoLo Solutions

Location: Chicago IL

Posted Jan 07, 2023

MoLo is seeking a Carrier Sales Representative for a fast-paced role from 1:00pm to 10:00pm CST. The successful candidate will cover same-day, next-day, and after-hour loads, develop carrier relationships, and meet performance metrics. MoLo offers a casual start-up culture, extensive training, career development, competitive salary, and comprehensive benefits. The company is committed to diversity and inclusion.

Technical Support Specialist

Company: Baird & Warner

Location: Chicago IL

Posted Jan 06, 2023

Baird & Warner Real Estate is a company that values its employees and provides them with the support they need to grow in their careers. They believe in empowering their team to be independent and make a positive impact on their community.

Product Designer

Company: LogicGate

Location: Chicago IL

Posted Jan 07, 2023

LogicGate is looking for a Product Designer to join their team and help build a robust platform for operationalizing and automating risk management and compliance programs. The ideal candidate is someone who is excited about solving new and difficult challenges, has cross-functional collaboration skills, and is a strong communicator and creative problem-solver. The company offers competitive total rewards packages, including a competitive salary range, variable plans, equity grants, paid time off, ongoing learning stipend, paid parental leave, 401k matching, health, vision, and dental insurance, accident and life insurance, and generous PTO, Annual Company Holidays, Summer and Winter Fridays, and Health Days. DEIB is a priority for the company, and they offer employee affinity groups, volunteer hours, and company-wide charitable activities.

Senior Staff / Principal Engineer

Company: SpotHero

Location: Chicago, IL

Posted Jan 08, 2023

SpotHero is looking for a Principal/Senior Staff Engineer with over 12 years of experience in software engineering. The ideal candidate will have strong coding skills, system design/architecture capabilities, and experience working with multiple companies. The role involves collaborating with management, contributing to the codebase, and providing support for any part of the codebase. The company offers a unique experience, excellent benefits, and a flexible PTO policy.

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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