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.

Product Designer

Company: Fetch Rewards

Location: Chicago IL

Posted Nov 14, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. They are looking for a Mid to Senior level Product Designer to continually push their app's customer experience and Product Design team to new levels.

Recruiter (Remote)

Company: Janus Health

Location: Chicago IL

Posted Nov 10, 2022

Janus Health Technologies is looking for a Recruiter to join their team. The Recruiter will be responsible for attracting, hiring, and retaining top talent, and will work closely with department managers to identify future hiring needs. The company offers a range of benefits, including 100% company-paid medical coverage, unlimited PTO, and employee stock options.

Growth Copywriter (Remote)

Company: Bump Boxes

Location: Chicago IL

Posted Nov 10, 2022

Bump Health is a women's health brand that is profitable, growing, and privately held. They are looking for a Growth Copywriter to join their marketing team and craft copy for their key marketing channels.

Senior Data Engineer

Company: Fetch Rewards

Location: Chicago IL

Posted Nov 13, 2022

Fetch Rewards is a build-first technology company creating a rewards program to power the world. The company has grown from 0 to 18M active users and aims to become a global platform that transforms how people connect with brands.

Sr. Counsel, Manager

Company: Avant

Location: Chicago IL

Posted Nov 11, 2022

Avant is seeking a motivated and experienced product counsel to join their legal team. The role involves building relationships, collaborating closely with business teams, providing legal advice, ensuring compliance, and working cross-departmentally. The ideal candidate has a J.D. degree, 4-6+ years of legal experience in consumer financial services law, and experience with consumer credit card products and privacy laws. The company values authenticity, collaboration, problem-solving, customer focus, and initiative.

Sales Operations Lead (Remote)

Company: Janus Health

Location: Chicago IL

Posted Nov 10, 2022

Janus is a company that believes in improving healthcare efficiency and is looking for a Sales Operations Lead to join their team. The company values its employees, is entrepreneurial, and has a strong culture. The role involves leading a sales enablement team, managing sales opportunities, and optimizing sales processes.

Data Protection Engineer

Company: Avant

Location: Chicago IL

Posted Nov 13, 2022

Avant is looking for a Data Protection Engineer to work on identifying, establishing and maintaining data protection technical controls in context of business and regulatory needs. The engineer will work closely with security leadership, teammates and stakeholders to evaluate and implement data protection controls that align with organizational risk posture and regulatory compliance requirements.

IT System Administrator

Company: NinjaTrader

Location: Chicago IL

Posted Nov 11, 2022

The IT System Administrator role at NinjaTrader is a key position in the growing IT team. The role involves supporting technical operations, managing various systems, and providing reports to senior management. The job requires at least four years of relevant experience, a Bachelor's degree in Computer Science or related field, and strong technical skills. The company offers competitive compensation and benefits, including 15 days PTO, 401k with company match, health insurance, and a gym membership. NinjaTrader is an investor-backed FinTech company committed to equal employment opportunity.

Sr. Client Onboarding Associate

Company: NinjaTrader

Location: Chicago IL

Posted Nov 12, 2022

NinjaTrader is seeking a Sr. Client Onboarding Associate to join their rapidly growing workforce in Chicago. The role involves assisting clients with opening new brokerage accounts, ensuring applications are processed within SLAs and in line with KYC and AML policies. The Sr. Client Onboarding Associate will be responsible for ensuring all KYC cases are completed to the highest standard and in line with regulatory and company policies. They will support Compliance, Payments, Client Services, and Sales teams by providing ongoing due diligence and transaction monitoring. The role includes reviewing and processing retail futures brokerage trading account applications, identifying and monitoring possible Politically Exposed Persons or Sanctioned individuals, conducting electronic checks, communicating with clients, processing a range of applications, addressing inquiries, engaging with client-facing departments, reviewing customer documentation, and driving the delivery of a best-in-class client onboarding function.

Regulatory Complaint Management (Customer Operations) Analyst

Company: Avant

Location: Chicago IL

Posted Nov 13, 2022

The job posting is looking for a Regulatory Complaint Analyst to support customer service and operational needs. The ideal candidate has a strong writing, regulatory, and complaint management background and is comfortable interacting with business leaders. The role involves investigating regulatory complaints, identifying root causes, and making recommendations for improvements.

Executive Director of Growth (Remote)

Company: Janus Health

Location: Chicago IL

Posted Nov 10, 2022

Janus Health Technologies is a company that aims to improve the lives of administrative workers in the healthcare industry. They are looking for an Executive Director of Growth to build and execute the overall sales approach to their Health System customers. The company values its employees, is entrepreneurial, and focused on creating a strong culture.

Brand Copywriter (Remote)

Company: Bump Boxes

Location: Chicago IL

Posted Nov 10, 2022

Bump Health is a women's health brand that is profitable, growing, and privately held. They are looking for a Brand Copywriter to join their marketing team and craft copy for their key marketing channels. The company has a great product in a market with incredible demand and wants the copywriter to make a big impact on the performance of their marketing campaigns.

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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