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.

Account Executive - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 07, 2022

Black Spectacles is a purpose-driven company that is looking for an Account Executive to join their team. The role involves acquiring, retaining, and growing B2B accounts through prospecting, inbound traffic, and account management. The company offers a range of benefits, including uncapped commission and quarterly quota attainment bonuses, and is committed to reducing barriers to entry in their industry.

Data Solution Owner

Company: Inspire11

Location: Chicago IL

Posted Aug 07, 2022

The text describes Inspire11, a company that values collaboration, authenticity, and innovation. They believe in empowering their team members to drive change and take ownership of their careers. The company culture is vibrant and light-hearted, with a focus on work-life balance and individualized professional growth.

Junior Software Engineer

Company: Silverwork Solutions

Location: Chicago IL

Posted Aug 04, 2022

The job posting is for a Junior Software Engineer position at Silverwork, a FinTech startup that is looking for motivated entry-level developers to join their team. The company is committed to hiring for skill and experience through a fair and consistent interview process and offers a competitive salary with generous bonus opportunities, unlimited PTO, and other benefits.

Sales Engineer

Company: Keeper Security, Inc.

Location: Chicago IL

Posted Aug 09, 2022

Keeper Security, Inc. is a leading provider of zero-trust and zero-knowledge security cloud services, offering products that are highly rated in the industry. They are seeking a Sales Engineer to join their elite team and work with customers to identify technical requirements and support the sale of their solutions.

Data Engineer

Company: Inspire11

Location: Chicago IL

Posted Aug 07, 2022

The company Inspire11 is looking for a Data Engineer to join their team. The role involves moving and transforming data optimally between different systems, designing and documenting ETL pipeline solutions, and creating and designing database objects. The company values individualized professional growth, work-life balance, and a vibrant company culture.

Sales Development Representative, Customer Success

Company: Kalderos

Location: Chicago IL

Posted Aug 09, 2022

Kalderos is a company that delivers technology solutions to simplify the coordination of drug discount programs in the US healthcare system. They are looking for a results-oriented Sales Development Representative to support their Customer Success - Covered Entity function.

Product Specialist for Health Tech Startup, Customer Success

Company: CancerIQ

Location: Chicago IL

Posted Aug 06, 2022

CancerIQ is a technology company that enables providers to recognize and empower patients with increased risk for cancer. The company is seeking a Product Specialist to work with customers and provide training and support.

Sr. Global Channel Marketing Manager

Company: Keeper Security, Inc.

Location: Chicago IL

Posted Aug 09, 2022

Keeper Security is hiring a Global Channel Marketing Manager to join their marketing team. The job requires experience in IT channel marketing, and the company offers a range of benefits and a positive work environment.

Senior Software Engineer

Company: CSC Corptax

Location: Chicago IL

Posted Aug 08, 2022

The job description is for a software development position at CSC Corptax, a company that provides business, legal, tax, and digital brand services. The job involves designing and developing features for a cloud-based commercial tax software product, working with a distributed team, and collaborating with other teams. The company offers competitive compensation, benefits, and opportunities for career advancement.

UX/UI Designer - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 04, 2022

Black Spectacles is a purpose-driven company that is looking for a UX/UI Designer to join their team. The company is committed to educating and inspiring architects and is expanding its team of enthusiastic go-getters. The role involves leading design thinking, creating effective plans, and crafting useful and usable experiences.

Partner Marketing Director

Company: Bringg

Location: Chicago IL

Posted Aug 08, 2022

The job posting is looking for a passionate marketer manager to join the growing marketing team. The role involves defining and leading marketing activities with partners, maintaining relationships, and developing joint marketing plans. The company values its team members and emphasizes collaboration, innovation, and growth.

Engineering Manager - Remote

Company: Black Spectacles

Location: Chicago IL

Posted Aug 01, 2022

Black Spectacles is a purpose-driven company that is looking for an Engineering Manager to manage and scale their engineering team. The company is committed to reducing barriers to entry and is an equal opportunity employer.

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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