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 Sales Incentive Associate

Company: Grubhub

Location: Chicago, IL

Posted Oct 24, 2023

Grubhub is seeking an experienced Senior Sales Compensation Associate to join their Revenue Operations team. The role involves designing sales compensation plans, calculating commissions, analyzing sales performance data, and collaborating with cross-functional teams. The ideal candidate should have a degree in Finance, Accounting, or a related field, and at least 3 years of experience in commissions operations or sales analytics. Strong data analysis skills, proficiency in Excel and commission calculation tools, and excellent communication skills are required. The company offers a generous compensation package, flexible PTO, health and wellness benefits, free meals, and opportunities for social impact.

Systems Support Engineer (Wed-Sun, 6pm-2am CST or EST)

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Oct 24, 2023

Keeper Security is hiring for a 100% remote Systems Support Engineer position. The role involves providing technical support to clients, resolving complex technical issues, and communicating with users of varying technical experience. The ideal candidate should have 5+ years of IT management and System Administration experience, proficiency in Mac OSX, Windows & Linux administration, and knowledge of Single Sign On (SSO) environments. The position offers competitive benefits and is part of a fast-growing cybersecurity company.

Associate Principal, Application Security

Company: OCC

Location: Chicago, IL

Posted Oct 25, 2023

The Options Clearing Corporation (OCC) is seeking a candidate for a role in secure software development. The successful applicant will work closely with various teams to implement security best practices in the software development life cycle, guide application teams in secure development, and integrate custom and commercial software with security infrastructure. Key responsibilities include application security testing, vulnerability management, release management, CI/CD pipeline integration, documentation, and process improvement. The ideal candidate should have excellent communication skills, analytical abilities, and a strong understanding of security concepts and practices. Preferred skills include experience with Terraform, cloud platforms, Java programming, and agile methodologies. OCC offers a collaborative environment with benefits such as a hybrid work model, tuition reimbursement, and generous PTO.

Systems Support Engineer

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Oct 25, 2023

Keeper Security is hiring for a 100% remote Systems Support Engineer position. The role involves providing technical support to clients, resolving complex technical issues, and communicating with users of varying technical experience. The ideal candidate should have 5+ years of IT management and System Administration experience, proficiency in Mac OSX, Windows & Linux administration, and knowledge of Single Sign On (SSO) environments. A Bachelor's Degree or equivalent experience is preferred. Keeper Security offers competitive benefits including medical, dental, vision, life insurance, 401k, and a generous PTO plan.

Sr. Analyst, Sales Programs

Company: Grubhub

Location: Chicago, IL

Posted Oct 24, 2023

Grubhub is seeking an experienced Senior Analyst, Sales Programs to join their Revenue Operations team. The role involves driving accurate, efficient, and timely commission processing, maintaining signed sales plan documents, and executing the rollout of compensation plans. The ideal candidate will have a Bachelor's degree in Finance, Accounting, Business Administration, or a related field, and at least 3 years of experience in commissions operations, sales analytics, or sales operations. They should have strong proficiency in data analysis, Excel, and commission calculation tools/systems, and excellent communication skills. The role offers a competitive compensation package, flexible PTO, health and wellness benefits, free meals, and opportunities for social impact.

CNU Collections Representative (Remote)

Company: Enova

Location: Chicago, IL

Posted Oct 23, 2023

Enova International is offering a fully remote Collections Representative position with a 4-week training program. The role involves handling inbound and outbound calls to customers regarding overdue loan payments, problem-solving for delinquent accounts, and maintaining accurate customer account information. Enova is a values-driven organization that provides online financial services through its AI-powered Colossus platform, serving non-prime consumers and businesses. The company offers a flexible work schedule, health benefits, 401(k) matching, PTO, and a sabbatical program. Enova is committed to equal employment opportunity and maintaining an inclusive work environment.

Senior Data Engineering and Cloud Architect (Databricks)

Company: West Monroe

Location: Chicago, IL

Posted Oct 25, 2023

West Monroe is seeking a Senior Data Engineering and Cloud Architect with extensive experience in data platform and architecture. The role involves collaborating with clients to address complex needs, leading large-scale implementations, and mentoring a team of engineers. The ideal candidate should have proficiency in Azure, AWS, and GCP tools, strong data engineering experience, and the ability to thrive in a fast-paced, collaborative environment. West Monroe offers competitive rewards, benefits, and opportunities for growth.

Business Analytics Associate

Company: Beyond Finance

Location: Chicago, IL

Posted Oct 25, 2023

Beyond Finance is a fintech company that aims to help Americans escape debt and achieve financial freedom. They are seeking an Associate Product Manager to join their team, responsible for customer and employee experience, and business KPIs. The ideal candidate should have a quantitative degree, excellent communication skills, and the ability to work independently. Beyond Finance offers a collaborative work environment, competitive benefits, and opportunities for career growth.

Sr. Manager, Technical Operations (#Hybrid Chicago near O'Hare Airport)

Company: Alliant Credit Union

Location: Chicago, IL

Posted Oct 24, 2023

This job posting is for a senior IT role with Alliant, requiring a Bachelor's degree in Computer Science or related field and 8 years of experience in technical operations. The role involves leading IT service management, disaster recovery, and technology compliance practices, driving operational excellence, and managing technical projects. Key responsibilities include developing strategies for optimizing technical operations, collaborating with cross-functional teams, and ensuring compliance with industry standards. The role also involves people management, coaching staff, and making hire/fire decisions. Benefits include competitive medical and dental benefits, paid parental leave, gym discounts, generous PTO, tuition reimbursement, and a 401k plan with immediate employer match. The job also requires adherence to Bank Secrecy Act policies and maintaining integrity and ethics in all actions.

Senior Financial Analyst (Hybrid)

Company: Enova

Location: Chicago, IL

Posted Oct 23, 2023

Enova is seeking a Senior Financial Analyst for its FP&A team. The role involves collaborating with stakeholders, providing analytical support, driving business insights, and evaluating business opportunities. Requirements include a finance degree, 2-5 years of relevant experience, strong problem-solving skills, and proficiency in Excel. Enova offers a flexible work schedule, comprehensive benefits, and a values-driven culture.

Software Engineer (Trading Operations)

Company: Aquatic Capital Management

Location: Chicago, IL

Posted Oct 23, 2023

Aquatic, a quantitative trading and investment company founded by Jon Graham, is actively recruiting for a Software Engineer. The role involves developing, managing, and maintaining a full-stack platform with a focus on front-end user experience. The engineer will collaborate with the Trading and Operations team to design, build, and implement a platform for global operations. Key responsibilities include developing and managing the user interface, designing a best-in-class application, integrating the platform with internal and external systems, improving operational workflow through automation, and building tools for the post-trade lifecycle. The ideal candidate should have at least 5+ years of full-stack development experience, expertise in modern technologies like PostgreSQL, Express.js, React, and Node.js, and a strong bias for action. The base salary is between $150,000 and $300,000, with potential for additional compensation and benefits.

Senior Instructional Designer

Company: Apex Fintech Solutions

Location: Chicago, IL

Posted Oct 24, 2023

Apex Fintech Solutions is a company that powers innovation and digital wealth management, with a focus on simplifying and automating financial markets. They offer a range of fintech solutions and have received several prestigious industry awards. The company is looking for a Senior Instructional Designer to join their HR Learning and Organizational Development team, with a focus on designing and developing learning programs.

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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