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.

Associate Principal, Cyber Risk

Company: OCC

Location: Chicago, IL

Posted Jun 12, 2023

The text describes a job position at the Options Clearing Corporation (OCC), a systemically important financial market utility. The role involves leading security observations, supporting process automation, conducting security assessments, and collaborating with various departments. The individual must have excellent communication skills, analytical abilities, and a strong understanding of information technology and risk management. Previous work in compliance, audit, risk management, or security is preferred.

IT Architect - Corporate Application Support

Company: Enfusion

Location: Chicago, IL

Posted Jun 15, 2023

Enfusion is a pioneer in developing innovative, native cloud investment management software, analytics, and managed services for asset managers and hedge funds around the globe. They offer a unique, seamless, SaaS-based platform that reshapes the global investment operations landscape. The company is committed to client service and offers expert managed services. They are looking for an IT Corporate Application Support Architect to analyze business processes, suggest improvements, implement technology solutions, and manage technology systems.

Instructional Designer I

Company: Everspring

Location: Chicago, IL

Posted Jun 11, 2023

The Learning Design team at Everspring is a collaborative group of professionals working to translate traditional courseware into online formats. The Instructional Designer I position, located in Chicago, IL, requires a motivated individual with a passion for creating outstanding learning experiences and a demonstrated track record of creating engaging, effective online programs. The role involves designing and building assigned courses, managing concurrent projects, communicating with faculty, and collaborating with the Creative Services team. The team values continuous improvement, curiosity, and learning by doing.

Compliance Analyst

Company: NinjaTrader

Location: Chicago, IL

Posted Jun 14, 2023

NinjaTrader is a FinTech company offering award-winning software and brokerage services to active traders. They are building products to help analyze and react to data from global financial markets. The company has a unique employee-centric culture in Chicago. The Compliance Analyst role involves understanding regulations, assisting with inquiries, coordinating with Marketing, reviewing promotional material, and providing compliance support. The company offers health, vision, dental coverage, 401k with company match, life and disability insurance, generous PTO, and 7 paid holidays. They are committed to equal employment opportunity and have a positive work environment.

Underwriter, NY Construction

Company: Argo Group

Location: Chicago, IL

Posted Jun 13, 2023

Argo Group is a leader in specialty insurance with a vibrant culture built on respect, equality, wellness, and opportunity. The company offers a comprehensive line of high-quality products and services designed to meet the unique coverage and claims-handling needs of its clients.

Client Services Representative

Company: NinjaTrader

Location: Chicago, IL

Posted Jun 12, 2023

NinjaTrader, a growth-stage FinTech company based in Chicago, is seeking a customer service representative with a passion for helping people and an interest in the trading industry and technology. The role involves resolving client support inquiries, educating customers on NinjaTrader's product line, and collaborating with internal teams. The ideal candidate should have empathetic communication skills, excellent time management, and be tech-savvy. Benefits include health coverage, 401k with company match, and generous PTO.

Manager, Cyber Defense

Company: OCC

Location: Chicago, IL

Posted Jun 12, 2023

The Manager, Cyber Defense will lead security professionals in analyzing threats and vulnerabilities, and overseeing security technology implementations. This role involves managing a team, leading incident response, and ensuring compliance. The ideal candidate should have team leadership experience, excellent communication skills, and technical expertise in various cybersecurity disciplines. OCC, the world's largest equity derivatives clearing organization, offers a collaborative environment with benefits like a hybrid work schedule, tuition reimbursement, and generous PTO.

Senior Underwriter, NY Construction

Company: Argo Group

Location: Chicago, IL

Posted Jun 13, 2023

Argo Group is a leader in specialty insurance with a vibrant culture built on respect, equality, wellness, and opportunity. They are an innovative organization that's small enough to be agile and big enough to make a difference in their industry. The company offers a flexible workplace, continuous learning, and professional development opportunities. They have a strong commitment to diversity, inclusion, and community outreach.

Senior Staff Data Engineer

Company: SADA

Location: Chicago, IL

Posted Jun 14, 2023

Join SADA as a Senior Staff Data Engineer, Corporate! Your mission will be to work with big data and emerging Google Cloud technologies to drive corporate services. You will have the opportunity to design, develop, and maintain the best Enterprise Data Warehouse solution to fit our corporate needs. You will be interacting with all of our business units and Google Cloud subject matter experts. From transforming business requirements, solution architecture, data modeling, architecting, ETL, metadata, and business continuity, you will have the opportunity to work collaboratively with architects and other engineers to recommend, prototype, build, and debug data infrastructures on Google Cloud Platform (GCP). You will have an opportunity to work on real-world data problems facing our customers today. Engagements vary from being purely consultative to requiring heavy hands-on work and covering a diverse array of domain areas, such as data migrations, data archival and disaster recovery, and big data analytics solutions requiring batch or streaming data pipelines, data lakes, and data warehouses. You will be expected to run point on whole projects, end-to-end, and to mentor less experienced Data Engineers. You will be recognized as an expert within the team and will build a reputation with Google and our customers. You will demonstrate repeated delivery of project architectures and critical components that other engineers demur to you for lack of expertise. You will also participate in early-stage opportunity qualification calls, as well as guide client-facing technical discussions for established projects.

Security Manager

Company: SpotHero

Location: Chicago, IL

Posted Jun 11, 2023

SpotHero is seeking a security manager to build a security program for their product application and corresponding infrastructure. The ideal candidate should have 5+ years of experience in security operations, with 1-2 years managing people. They should have excellent communication skills, a deep understanding of cybersecurity, and be comfortable leading initiatives and change management. The role offers competitive benefits, flexible PTO, and a supportive work/life balance.

Chief of Staff to the CEO

Company: Keeper Security, Inc.

Location: Chicago, IL

Posted Jun 14, 2023

Keeper is seeking a dynamic and proactive Chief of Staff to support the CEO in executing the company's vision and strategic priorities. The role involves providing strategic guidance, driving the implementation of key business initiatives, and overseeing daily operations. The ideal candidate should have a demonstrated track record of success in progressive leadership roles, deep experience in business operations, and the ability to build strong relationships and interact with all levels of the organization.

Manager, Financial Services Consulting

Company: West Monroe

Location: Chicago, IL

Posted Jun 14, 2023

West Monroe is currently seeking a Manager with Commercial Lending and Consulting expertise in the Financial Services industry to join their Chicago Financial Services Practice. The role involves applying personal and corporate knowledge and experience to tailor solutions and build partnerships helping clients gain competitive advantage in their markets. The Manager will help business and technology executives solve key problems and be responsible for leading engagements focused on improvement to commercial lending process and technology.

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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