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.

Customer Success Manager, Commercial

Company: Kalderos

Location: Chicago, IL

Posted May 26, 2023

Kalderos is a healthcare technology organization focused on pharmaceutical pricing transparency, trust, and equity. They are looking for a Customer Success Manager-Manufacturing to support drug manufacturers with onboarding and production operations, and to engage with states and pharmacy benefit managers. The role requires strong analytical skills, project management, and experience with SaaS/cloud-based products or platforms. Kalderos offers medical, dental, and vision benefits, 401k with company match, flexible work schedule, unlimited PTO, and more.

Accountant II

Company: Curaleaf

Location: Chicago, IL

Posted May 24, 2023

Curaleaf Holdings, Inc. is a leading international cannabis company with a mission to enhance lives through the power of the plant. The company operates in 19 US states and Europe, offering a range of cannabis products and services. Curaleaf is committed to corporate social responsibility, with initiatives focused on education, national partnerships, and local causes. The company values diversity, inclusivity, and teamwork, offering competitive benefits and a start-up environment. Curaleaf has received several awards for its contributions to the cannabis industry.

Senior Associate, Business Analysis

Company: OCC

Location: Chicago, IL

Posted May 24, 2023

The job posting is seeking a business system analyst with experience in discovery, synthesis, and analysis of information. The ideal candidate should have strong communication, analytical, and problem-solving skills, and be comfortable working with various stakeholders. The job requires collaboration, presentation, and facilitation skills, and experience with agile methodologies and process modeling tools.

System Administrator

Company: HealthJoy

Location: Chicago, IL

Posted May 24, 2023

None Found

Paralegal

Company: Grubhub

Location: Chicago, IL

Posted May 24, 2023

Grubhub is a place where authentically fun culture meets innovation and teamwork. They believe in empowering people and opening doors for new opportunities. The company values strong relationships, embraces diverse ideas, and has a fast-paced environment that thrives on collaboration. They are seeking a Paralegal to support their litigation team with discovery, document production, database tracking, case administration, and law enforcement requests. The ideal candidate will have outstanding organizational capabilities, attention to detail, and a team player attitude.

Assistant Controller/Controller

Company: SpotHero

Location: Chicago, IL

Posted May 24, 2023

SpotHero is seeking an Assistant Controller/Controller to join its expanding team. The role involves overseeing all aspects of the Accounting function, including month-end close, financial reporting, audits, and A/P, A/R, payroll, and tax functions. The ideal candidate should have a strong background in GAAP accounting, be a proven leader, and enjoy process improvement. The company offers a fast-growing environment with excellent benefits, flexible PTO, and a supportive work-life balance.

Full Stack Engineer (Platform Engineer)

Company: Infleqtion

Location: Chicago, IL

Posted May 26, 2023

Infleqtion is a global quantum technology company seeking a Platform Engineer to improve SuperstaQ infrastructure, accelerate developer velocity, and maintain servers. The role requires a Bachelor's degree in engineering, computer science, or related fields, and at least 2 years of professional work experience in software development. The company offers a generous Total Rewards program, including 100% company-paid employee coverage for medical, dental, vision, and short/long term disability insurance programs, unlimited paid time off, and more.

Senior Software Engineer- Security Engineering

Company: Grubhub

Location: Chicago, IL

Posted May 24, 2023

Grubhub is seeking a talented engineer with 5+ years of experience in code engineering and 2+ years in application security to join their Security Engineering team. The role involves designing and implementing automated code vulnerability scanners, integrating security controls into the SDLC pipeline, and ensuring high security standards across their technical infrastructure, applications, and processes. The ideal candidate should have experience with AWS Cloud Environments, Python development, and knowledge of network and application security best practices. Grubhub offers a generous compensation package, flexible PTO, health and wellness benefits, free meals, and opportunities for social impact.

Associate Principal - AWS DevOps

Company: OCC

Location: Chicago, IL

Posted May 24, 2023

The job description involves providing subject matter expertise for ongoing support of applications deployed to OCC's non-production AWS environments and supporting third-party applications. The individual will identify root causes and automate solutions in support of development. They will work under general supervision and manage day-to-day activities when called upon. The primary duties include designing, building, and maintaining Kafka infrastructure, integrating Kafka with cloud-based systems, optimizing Kafka performance, and collaborating with development teams.

Technical Training Specialist

Company: Pricefx

Location: Chicago, IL

Posted May 24, 2023

Pricefx is a young and unconventional software company that provides native Cloud and SaaS pricing solutions. They are an agile company with a focus on market-driven innovation, serving diverse industries and sizes. The company is growing globally and offers a full-time position in Chicago, Illinois or remotely. The role involves creating and delivering price and product training, maintaining and updating skills, collaborating on product topics, and assisting in education and product adoption projects.

Associate Principal, IT Governance

Company: OCC

Location: Chicago, IL

Posted May 24, 2023

The job description is for an IT program development and oversight role at the Options Clearing Corporation (OCC). The role involves developing, implementing, and evaluating IT programs, collaborating with teams, and recommending technologies to improve efficiency and security. The job requires strong analytical and data reporting skills, ability to work in a fast-paced environment, and excellent communication skills.

Employee Relations Manager

Company: Curaleaf

Location: Chicago, IL

Posted May 25, 2023

Curaleaf Holdings, Inc. is a leading international provider of consumer products in cannabis with a mission to enhance lives by cultivating, sharing, and celebrating the power of the plant. The company operates in 19 states with 150 dispensaries and employs nearly 5,500 team members. Curaleaf is committed to taking corporate and social responsibility very seriously and has initiatives focused on education, partnerships, state-wide initiatives, and local causes. The company aims to be the world's leading cannabis company by consistently delivering superior products and services and driving the global acceptance of cannabis.

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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