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Remote Operations Engineer Jobs in Chicago, IL (NOW HIRING)

DataAnnotation

DevOps Engineer

Elgin, IL · Remote

$40 - $75/hr

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and ... other engineers -- who are driving real-world impact in AI development. Our platform offers an ...

DataAnnotation

DevOps Engineer

Naperville, IL · Remote

$40 - $75/hr

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and ... other engineers -- who are driving real-world impact in AI development. Our platform offers an ...

DataAnnotation

DevOps Engineer

Chicago, IL · Remote

$40 - $75/hr

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and ... other engineers -- who are driving real-world impact in AI development. Our platform offers an ...

DataAnnotation

DevOps Engineer

Joliet, IL · Remote

$40 - $75/hr

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and ... other engineers -- who are driving real-world impact in AI development. Our platform offers an ...

DataAnnotation

DevOps Engineer

Aurora, IL · Remote

$40 - $75/hr

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and ... other engineers -- who are driving real-world impact in AI development. Our platform offers an ...

IT Labs

Senior DevOps Engineer

Chicago, IL · Remote

$133K - $170K/yr

... s Engineer to support one of the most innovative companies in the digital health space. Our client ... Remote * US-based -- US citizenship is required * Contract or B2B arrangement Our values We are a ...

Honor

Staff Platform Engineer - Infra + DevOps

Chicago, IL · Remote

$194K - $220K/yr

We are looking for a seasoned Platform Engineer with experience in designing, implementing, and ... We use national average to determine pay as we are a remote first company. Individual pay is based ...

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All JobsRemote Operations Engineer JobsRemote Operations Engineer Jobs in Chicago, IL

Remote Operations Engineer information

See Chicago, IL salary details

$37.1K

$87.6K

$139.1K

How much do remote operations engineer jobs pay per year?

As of Jun 16, 2026, the average yearly pay for remote operations engineer in Chicago, IL is $87,592.00, according to ZipRecruiter salary data. Most workers in this role earn between $71,600.00 and $96,800.00 per year, depending on experience, location, and employer.

What are some common challenges faced by Remote Operations Engineers, and how can they be addressed?

Remote Operations Engineers often encounter challenges such as managing critical systems across different time zones, quickly diagnosing issues without on-site access, and maintaining clear communication with global teams. To succeed, it's important to leverage robust monitoring and automation tools, proactively schedule regular check-ins, and document processes thoroughly. Developing strong relationships with team members and participating in virtual collaboration sessions can also help overcome remote work barriers. In this dynamic role, adaptability and continuous learning are key to staying ahead of evolving technology and operational demands.

What are the key skills and qualifications needed to thrive in the Remote Operations Engineer position, and why are they important?

To thrive as a Remote Operations Engineer, you need a solid background in systems administration, networking, and cloud infrastructure, often demonstrated by a degree in computer science or a related field. Familiarity with tools like AWS, Azure, remote monitoring systems, and relevant certifications such as AWS Certified SysOps Administrator or CompTIA Network+ is highly valuable. Strong problem-solving skills, proactive communication, and excellent time management help engineers excel in remote and collaborative environments. These skills ensure efficient, reliable operations management and smooth coordination with distributed teams and stakeholders.

What is a Remote Operations Engineer job?

A Remote Operations Engineer monitors, manages, and optimizes systems and processes from a remote location, ensuring efficiency and reliability. They use advanced technology and software tools to oversee operations in industries like energy, manufacturing, or IT. Their responsibilities include troubleshooting, data analysis, and collaborating with on-site teams to maintain smooth operations. Strong technical skills, problem-solving abilities, and adaptability are essential for this role.

What are the most commonly searched types of Operations Engineer jobs in Chicago, IL? The most popular types of Operations Engineer jobs in Chicago, IL are:
What are popular job titles related to Remote Operations Engineer jobs in Chicago, IL? For Remote Operations Engineer jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Operations Engineer jobs in Chicago, IL look for? The top searched job categories for Remote Operations Engineer jobs in Chicago, IL are:
What cities near Chicago, IL are hiring for Remote Operations Engineer jobs? Cities near Chicago, IL with the most Remote Operations Engineer job openings:
Remote Operations Engineer jobs near you
Infographic showing various Remote Operations Engineer job openings in Chicago, IL as of June 2026, with employment types broken down into 70% Full Time, 24% Part Time, 2% Contract, and 4% Nights. Highlights an 86% Physical, 7% Hybrid, and 7% Remote job distribution, with an average salary of $87,592 per year, or $42.1 per hour.
Security Operations Engineer - AI Trainer

Security Operations Engineer - AI Trainer

DataAnnotation

Naperville, IL • Remote

$50 - $100/hr

Contractor

Posted 23 days ago

Be an early applicant

Job description

About the job:

Contribute to developing cutting-edge AI systems, while enjoying the flexibility of remote work and setting your own schedule.

We are looking for existing cybersecurity professionals to help advance AI development. Cybersecurity platforms are increasingly powered by AI — but these systems still need practitioners with real-world experience to validate whether the outputs actually hold up in practice. That's where you come in.

You'll work closely with state-of-the-art AI models on tasks like evaluating AI-generated security content, solving technical security problems, and providing feedback that directly shapes how these systems reason about real-world threats and defenses.

To get started, once you sign up for an account, you'll take a short assessment (this serves as our version of an interview). If you pass, you'll receive an email confirmation, and paid work will become available to you through our platform.

Advantages of contracting with us:

  • Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand.
  • Flexible schedule: choose which projects you take on and when you work.
  • You work on your own schedule, on your own computer, from the comfort of your own home
  • Projects are paid hourly starting at $50-100+/hr, with bonus rates available on some projects
  • Impact: help shape the future of AI technologies built for cybersecurity.

Responsibilities:

  • Evaluate AI-generated cybersecurity content — including threat analysis, vulnerability assessments, and offensive security techniques — for real-world accuracy and validity.
  • Design and solve security-focused technical problems used to train AI systems.
  • Write clear technical explanations and security-relevant code.
  • Provide feedback that directly shapes the next generation of AI security models.

Qualifications:

  • 2+ years of hands-on experience in a cybersecurity role — such as penetration testing, red teaming, incident response, detection engineering, DFIR, malware analysis, threat intelligence, or adjacent fields, including government or military cyber operations.
  • Some coding experience required; comfort navigating and patching a codebase is key.
  • Fluency in English (native or bilingual level) with strong writing skills.
  • A bachelor's degree is preferred.
  • Cybersecurity certifications are a plus (e.g., OSCP, CRTO, GREM, GCFA, CEH, and similar).

Note: Payment is made via PayPal. We will never ask for any money from you. This job is only available to those in the US, Canada, UK, Ireland, Australia, and New Zealand. This is an independent contractor position.

#cybersecurity