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 Manager, Strategy & Operations - NetCredit Line of Credit (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Oct 18, 2023

The Senior Manager, Strategy & Operations - NetCredit Line of Credit role at Enova involves developing strategy, managing day-to-day operations, and ensuring a positive customer experience. Key responsibilities include supporting the P&L leader in strategy development, financial forecasting, and budgeting. The role requires strong financial acumen, analytical skills, and the ability to drive revenue growth and profitability. Enova offers a flexible work schedule, comprehensive benefits, and a values-driven culture.

Chief Information Security Officer

Company: FOURKITES

Location: Chicago, IL

Posted Oct 17, 2023

FourKites, a leading supply chain visibility platform, is seeking a Chief Information Security Officer (CISO) with extensive experience in cybersecurity and cloud operations. The CISO will lead the Information Security and IT teams, oversee security policies, manage vulnerability assessments, and ensure regulatory compliance. The role involves working closely with executives and departments, engaging with external stakeholders, and driving continuous improvement in the company's security posture.

Software Engineer

Company: Grainger

Location: Chicago, IL

Posted Oct 18, 2023

Grainger, a leading Maintenance Repair & Operating provider in North America, is seeking an experienced Infrastructure Automation Engineer. The role involves developing an automation framework for IT infrastructure using Python and Ansible, promoting automation across the technology group, and collaborating with various teams to expand automation capabilities. The ideal candidate should have a Bachelor's degree in computer science or related field, 3+ years of experience as a software engineer, and proficiency in higher-level programming languages, configuration management platforms, and DevOps tools. Grainger offers comprehensive benefits, including medical, dental, vision, life insurance, paid time off, 401(k) contributions, employee discounts, parental leave, and wellbeing programs.

Head of Product Management

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Oct 18, 2023

Keeper Security, a leading cybersecurity company, is seeking a Head of Product Management to lead and execute on all aspects of product management. The role involves driving product vision, strategy, and roadmap in support of a product-led growth strategy. The successful candidate will collaborate with an elite team of industry experts to innovate and deliver industry-leading products. The position offers a competitive benefits package and the opportunity to work with a fast-growing company in the cybersecurity sector.

Customer Success Executive

Company: Pricefx

Location: Chicago, IL

Posted Oct 18, 2023

Pricefx is a leading SaaS Pricing and CPQ vendor offering flexible work opportunities, a warm and welcoming environment, and a focus on employee growth and development. The company is seeking a Customer Success Manager to manage and serve as the primary contact for Spanish-speaking customers, providing guidance on measuring success and best practices.

Chief Information Security Officer

Company: FOURKITES

Location: Chicago, IL

Posted Oct 17, 2023

FourKites is a company that offers a unique opportunity to work on complex challenges with real-world impacts. The company is looking for a Chief Information Security Officer to lead its cybersecurity initiatives and ensure the secure and efficient delivery of software services.

Technical Support Specialist

Company: SpotHero

Location: Chicago, IL

Posted Oct 17, 2023

Effective at partnering internally and externally to drive resolution of both new fulfillment requests and integration issues while also driving continuous improvement and education for self-service for Operators and across Supply Management teams. What you will do: Work with Operators, PARCS vendors, IT services vendors, Sales Ops, Account Executives to onboard new supply locations onto SpotHero platform.Partners with Supply Management to proactively share improvements in onboarding intake processMeets weekly with Supply Management to share blockers and seek clarity on any known internal and external blockersEnsures the Salesforce queue is maintained at acceptable levels and status is accurate and current.Distinguish and triage between bugs, tasks, and product improvements and escalate appropriately, both internally and externally.Develop and revise our playbooks and knowledge base to improve company efficiency.Increase efficiency and productivity of activation and fulfillment of new supply locations being integrated into SpotHero platformPartners with Product and Engineering to increase efficiency at diagnosing, documenting, and resolving complicated issues.Helps define opportunities and requirements for self-service tooling for operators.Attend biweekly Engineering sprint meetings, representing the voice of the Operators and Supply team.Secure and safeguard data to preserve its integrity, reliability, and availability and ensure appropriate access levels are maintained.Assist SMS-Admin team with requests that require higher level of technical supportWork with Supply, Rev Ops and Product on complex rate-related queries and scaling rate self-service in SpotHero Control Panel The following experience is relevant to us:Bachelor’s degree in Computer Science, Computer Engineering or equivalent with 3+ years experience in a technical support role working with Network related productsAbility to maintain a high level of productivity while managing multiple competing prioritiesProven understanding of web technologies such as Chrome, Safari, Firefox, etc.Good understanding of API technologies and troubleshooting (Postman preferred)Intermediate SQL knowledge (DataGrip preferred)Experience with logging and monitoring tools such as Sumo LogicExperience with Salesforce, Jira and ConfluenceCore Competencies: Action-Oriented - Maintains a sense of urgency to complete a task and seeks information rather than waiting for it.Analytical - Examines information methodically and in detail to solve problems or complete tasks.Collaboration - Process of working with multiple individuals to complete a task or achieve a goal.Multi-Task - Execute on more than one task at the same time.Patience - Remains calmly focused on resolving issues.Process Improvement - Evaluates processes to ensure the most efficient method is used.Relationship Management - Ability to build and maintain relationships with coworkers and business partners.Technical Capability - Ability to identify how systems and technology can improve ways of working.Time Management - Ensures performance helps maintain desired service levels.Time Management - Ensures performance helps maintain desired service levels.Tools we use:  SpotHero Admin Backend, Salesforce, BI Tool (Looker preferred), Issue and Project Tracking Software (Jira preferred), Log Management & Security Analysis Software (Sumo Logic preferred), Knowledge Sharing Platform (Confluence preferred), API testing tools for manual / exploratory testing (SOAPUI, Postman Preferred), SQL tools (pgadmin, datagrip preferred) What we are offering:Career game changer – A truly unique experience to work for a fast-growing startup in a role with unlimited potential for growth.Excellent benefits – In the US we cover up to 95% of Medical Premiums, 50% of Dental & Vision Premiums, company-sponsored Life Insurance, 401K, and generous parental leave. In Canada, we offer Medical (prescription drug and paramedical coverage), Dental, Vision, Life Insurance, STD, and LTD. Flexible PTO policy and great work/life balance – We value and support each individual team member.Annual parking stipend – we help people park!The opportunity to collaborate with fun, innovative, and passionate people in a casual, yet highly productive atmosphere.A workplace recognized as the Best Consumer Web Company by Built in Chicago, Top Company Culture by Entrepreneur, a Top Workplace by Chicago Tribune, and one of Chicago’s Best Places to Work for Women Under 35 by Crain’s Chicago Business. Steps to apply: Please include any GitHub account, LinkedIn profile, and any project that you’re particularly proud of. We love seeing work that others loved working on.SpotHero is an equal opportunity employer. We know that a diverse workforce is the strongest workforce, and are committed to building and supporting an inclusive environment for all. You will be responsible for partnering with Supply Management Specialists, IT & PARCS service vendors, Operators and Product & Engineering to onboard 3rd party integrations onto the SpotHero platform and fulfillment activities for Operators looking to leverage SpotHero services (SIQ, Blue Access, PARCS Integations).

Customer Success Manager

Company: Pricefx

Location: Chicago, IL

Posted Oct 18, 2023

Pricefx, a leading SaaS Pricing and CPQ vendor, is seeking a Spanish-speaking professional to manage customer relationships, provide support, and gather insights to improve the product. The role involves onboarding, adoption, and growth of customers, as well as addressing concerns and commercial escalations. The company values flexibility, diversity, and work-life balance, offering remote work opportunities, a monthly IT allowance, and comprehensive benefits including healthcare, 401K matching, and paid time off.

Technical Support Specialist

Company: SpotHero

Location: Chicago, IL

Posted Oct 17, 2023

The role involves partnering with various teams to support 3rd party integrations onto the SpotHero platform and fulfillment activities for Operators. The individual will work with Operators, PARCS vendors, IT services vendors, Sales Ops, and Account Executives to support new supply locations on SpotHero platform. They will also collaborate with Product and Engineering to increase efficiency at diagnosing, documenting, and resolving complicated issues. The role requires a Bachelor's degree in Computer Science, Computer Engineering or equivalent with 3+ years experience in a technical support role. The company offers excellent benefits, flexible PTO policy, and a collaborative atmosphere.

Manager, Partnerships

Company: Grubhub

Location: Chicago, IL

Posted Oct 17, 2023

We evaluate qualified applicants without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, and other legally protected characteristics. Compensation. Social Impact. Free Meals. Grubhub is an equal opportunity employer. You'll receive a great compensation package with eligibility for generous incentives, bonuses, commission, or RSUs (role-specific). Health and Wellness. At Grubhub we believe in giving back through programs like the Grubhub Community Fund . Excellent medical, dental and vision benefits, 401k matching, employee network groups and paid parental leave are just a few of our programs to support your overall well-being. Our employees get a weekly Grubhub credit to enjoy and support local restaurants.

Associate Principal, Cloud Engineering

Company: OCC

Location: Chicago, IL

Posted Oct 17, 2023

Strong hands-on experience scripting/development skills in Python, Ruby, Go, Java, JavaScript, etc. in a corporate environment Working knowledge of infrastructure design and components, such as servers, operating systems, networks, and storage Hands-on experience with: Terraform, Kubernetes, Jenkins, Kafka, Github, OpenShift, and configuration management tools such as Puppet, Chef, or Ansible Experience with architecting, implementing and maintaining highly available mission critical environments for 24x7 availability Experience working in an environment with a defined production change control process Technical Skills: Relevant experience with configuration and implementation of IaaS, Infrastructure as code, AWS, Azure, etc. Step 2You will receive an email notification to confirm that we've received your application.Step 3If you are called in for an interview, a representative from OCC will contact you to set up a date, time, and location. CIS, NIST, etc). Design, develop, and build the business's cloud infrastructure architecture.Qualifications:The requirements listed are representative of the knowledge, skill, and/or ability required. For more information about OCC , please click here .OCC is an Equal Opportunity Employer Demonstrated history of working within deadlines and ability to work well under pressure Education and/or Experience: Bachelor's degree, preferably in a technical discipline (Computer Science, Mathematics, etc. Develop and maintain a library of deployable, tested, and documented automation design scripts, processes, and procedures. Founded in 1973, OCC is dedicated to promoting stability and market integrity by delivering clearing and settlement services for options, futures and securities lending transactions. As a Systemically Important Financial Market Utility (SIFMU), OCC operates under the jurisdiction of the U.S. Securities and Exchange Commission (SEC), the U.S. Commodity Futures Trading Commission (CFTC), and the Board of Governors of the Federal Reserve System.

Speech Analyst (Remote)

Company: Enova

Location: Chicago, IL

Posted Oct 18, 2023

Enova International is seeking a Speech Analyst with 2 or more years of experience in speech analytics and proficiency in CallMiner or similar software. The role involves building and testing speech categories, identifying trends, and collaborating with leadership on strategic initiatives. Enova offers a flexible work schedule, comprehensive benefits, and a values-driven culture. The company is committed to equal employment opportunities and fostering an inclusive environment.

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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