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 Associate, Chicago

Company: Chowbus

Location: Chicago, IL

Posted Feb 11, 2023

The job posting is for an entrepreneurial customer success expert to lead the onboarding of new restaurants to the Chowbus marketplace app, manage client restaurant accounts, and provide support and coordination for various tasks. The ideal candidate should have a bachelor's degree, be bilingual, have excellent communication skills, and have experience in account management or sales. The company offers a fair compensation package, medical insurance, and unlimited PTO.

Senior Software Engineer, Backend

Company: HealthJoy

Location: Chicago, IL

Posted Feb 07, 2023

HealthJoy is a company that aims to simplify healthcare benefits for users. They are looking for a senior software engineer to join their marketing team and develop software that improves people's lives.

Resolutions Management Associate

Company: Avant

Location: Chicago, IL

Posted Feb 11, 2023

The job description is for a Resolutions Management Associate on the Customer Operations Team at Avant. The role involves leading three teams, coordinating daily/weekly/monthly trends monitoring, and exercising judgment to escalate departmental issues or employee concerns. The ideal candidate has a minimum of 3-4 years of strategic and operating roles with proven results, strong people management and development skills, and experience continuously improving customer-facing operations.

Account Executive

Company: VideoAmp

Location: Chicago, IL

Posted Feb 08, 2023

VideoAmp is seeking highly energetic, motivated, and fun sales leaders to drive explosive growth on the Account Sales Team. Candidates should have a proven track record of exceeding revenue goals, building relationships, and living by the company's values. The role involves exceeding revenue goals, accelerating demand for VideoAmp solutions, and championing the VideoAmp brand. Candidates should have 3 years of agency experience with 1-2 years of sales experience and deep product knowledge. The company offers a minimum base salary of $95,000, unlimited paid time off, company-sponsored benefits, fitness classes, and wellness programs.

Sales Development Representative - Remote

Company: Ascent

Location: Chicago, IL

Posted Feb 08, 2023

Ascent is a Chicago-based startup that offers a platform for regulatory compliance. The company is looking for a Sales Development Representative to join their team. The role involves identifying prospective customers, managing inbound leads, and nurturing relationships to close deals.

IT Service Desk Hardware Technician

Company: Capstone Logistics, LLC

Location: Chicago, IL

Posted Feb 10, 2023

Capstone is a data-driven, results-oriented transportation solutions provider offering integrated solutions for inbound logistics to last-mile delivery. They are looking for sharp, ambitious candidates to join their team, providing first-level and second-level support for incoming technology issues. The position involves proactive support, customization and deployment of new/upgraded hardware and software, and maintaining a central source of information for service desk staff and support technicians.

Principal Site Reliability Engineer

Company: Avant

Location: Chicago, IL

Posted Feb 09, 2023

Avant is a company that values diversity, collaboration, and problem-solving. They offer a range of benefits and perks, including flexible work environment, unlimited paid time off, and access to LinkedIn Learning. The company is looking for a platform architecture leader to help drive efforts to maintain the integrity of their platform and services.

Senior Data Platform Engineer

Company: Highnote

Location: Chicago, IL

Posted Feb 08, 2023

Highnote is a fintech company that provides an all-in-one card issuer processor and program management platform. They are looking for a Data Platform Team member to build modern scalable, secure, and reliable data platforms and data pipelines.

Copywriter

Company: Kalderos

Location: Chicago, IL

Posted Feb 09, 2023

Kalderos is a company that is building unifying technologies to bring transparency, trust, and equity to the healthcare community. They are looking for a Copywriter to join their team and are offering a range of benefits and perks.

Enterprise Account Executive, Central (Remote-Chicago)

Company: OnSiteIQ

Location: Chicago, IL

Posted Feb 09, 2023

OnSiteIQ is seeking an Enterprise Account Executive to drive regional sales efforts and manage all sales activities within assigned accounts composed of premier real estate developers, property owners, corporations, and private equity funds. The role involves end-to-end sales motions with largest customers, representing the brand, and moving the mission forward. The candidate will have the ability to work remotely and travel when needed for customer visits and internal meetings. The role requires leading revenue objectives, connecting with C-level executives, building and executing on an account strategy, and driving top-of-funnel activity.

Senior Software Engineer

Company: Highnote

Location: Chicago, IL

Posted Feb 08, 2023

Highnote is an all-in-one card issuer processor and program management platform founded in 2020 by a team of leaders from Braintree, PayPal, and Lending Club. They have raised $104M+ and have 100+ employees. They operate through their core values of customer obsession, executional excellence, and intentional inclusion. They are looking for builders who thrive in ambiguity and are excited about shipping customer-centric software.

Customer Growth Manager

Company: BenchPrep

Location: Chicago, IL

Posted Feb 08, 2023

The text describes a role for a Customer Growth Manager at BenchPrep, a company that delivers an advanced learning experience for certification, credentialing, test prep, continuing education, and training. The role involves working with existing customers to identify growth opportunities and expand their relationship with BenchPrep. The company values customer centricity, problem-solving, and a positive attitude. They offer a total rewards package, including medical benefits, potential for yearly bonus, stipends for work-from-home expenses, flexible paid time off, annual professional development stipend dollars, and a competitive base salary.

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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