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Remote Offensive Analyst Jobs in Chicago, IL (NOW HIRING)

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SOC Analyst

Elgin, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Cybersecurity Analyst

Joliet, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Cybersecurity Analyst

Elgin, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Cybersecurity Analyst

Naperville, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Cybersecurity Analyst

Aurora, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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SOC Analyst

Chicago, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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SOC Analyst

Aurora, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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SOC Analyst

Joliet, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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SOC Analyst

Naperville, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Cybersecurity Analyst

Chicago, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... and offensive security techniques -- for real-world accuracy and validity. * Design and solve ...

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Penetration Tester

Joliet, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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Penetration Tester

Elgin, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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Red Team Engineer

Chicago, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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AI Security Specialist

Joliet, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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Penetration Tester

Naperville, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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Security Operations Engineer

Aurora, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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Cloud Security Engineer

Chicago, IL · Remote

$40 - $75/hr

Fully remote: work from anywhere in the US, Canada, UK, Ireland, Australia, and New Zealand ... threat analysis, vulnerability assessments, and offensive security techniques -- for real-world ...

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All JobsRemote Offensive Analyst JobsRemote Offensive Analyst Jobs in Chicago, IL

Remote Offensive Analyst information

See Chicago, IL salary details

$31.9K

$75.5K

$133.9K

How much do remote offensive analyst jobs pay per year?

As of May 28, 2026, the average yearly pay for remote offensive analyst in Chicago, IL is $75,469.00, according to ZipRecruiter salary data. Most workers in this role earn between $54,100.00 and $89,600.00 per year, depending on experience, location, and employer.

What are the key skills and qualifications needed to thrive as a Remote Offensive Analyst, and why are they important?

To thrive as a Remote Offensive Analyst, you need strong expertise in cybersecurity, penetration testing, vulnerability assessment, and a solid understanding of network protocols, often supported by a degree in computer science or a related field. Familiarity with tools such as Metasploit, Burp Suite, Nmap, and certifications like OSCP or CEH are typically required. Analytical thinking, problem-solving skills, and clear communication are crucial soft skills for effectively reporting findings and collaborating with distributed teams. These abilities are vital for identifying exploitable weaknesses and strengthening an organization's security posture in a remote work environment.

How does a Remote Offensive Analyst typically collaborate with other cybersecurity team members while working offsite?

As a Remote Offensive Analyst, you will frequently collaborate with cybersecurity teams through virtual meetings, secure chat platforms, and shared documentation tools. Effective communication is crucial, as you'll often coordinate penetration testing efforts, share findings with blue team members, and participate in debrief sessions with stakeholders. Despite the remote setup, teamwork remains essential—expect to work closely with incident response, threat intelligence, and IT staff to ensure vulnerabilities are identified and addressed efficiently. Regular updates and clear documentation help maintain alignment and foster a strong security posture across distributed teams.

What is a Remote Offensive Analyst?

A Remote Offensive Analyst is a cybersecurity professional who works remotely to identify and exploit vulnerabilities in computer systems, networks, and applications. Their primary role is to simulate cyberattacks, such as penetration testing or red teaming, to help organizations find and fix security weaknesses before malicious actors can exploit them. By working remotely, these analysts can perform security assessments from anywhere in the world, often using specialized tools and techniques. They play a critical role in strengthening an organization's cybersecurity defenses and ensuring compliance with industry regulations.

What is the difference between Remote Offensive Analyst vs Remote Penetration Tester?

AspectRemote Offensive AnalystRemote Penetration Tester
CredentialsCertifications like OSCP, CEH, CISSP often preferredCertifications like OSCP, CEH, GPEN commonly required
Work EnvironmentTypically part of security teams, focusing on offensive security strategiesOften contracted or employed within security firms, conducting simulated attacks
Industry UsageUsed in cybersecurity teams across various industries for proactive security testingCommonly used in cybersecurity consulting and internal security assessments

Both roles focus on offensive security, but Remote Offensive Analysts often work within organizations' security teams to develop attack simulations, while Remote Penetration Testers usually perform external assessments for clients. The skills and certifications overlap significantly, making them closely related but distinct in their typical work settings.

What are popular job titles related to Remote Offensive Analyst jobs in Chicago, IL? For Remote Offensive Analyst jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Remote Offensive Analyst jobs in Chicago, IL look for? The top searched job categories for Remote Offensive Analyst jobs in Chicago, IL are:
Remote Offensive Analyst jobs near you

Offensive Security Analyst (Structured / Non-Exploit)

Alignerr

Chicago, IL • Remote

Other

This job post has expired today. Applications are no longer accepted.

Job description

Offensive Security Analyst (Structured / Non-Exploit) - AI Training
About the Role
What if your ability to trace an attacker's footsteps - mapping kill chains, spotting defensive gaps, and modeling adversary behavior - could directly shape how the world's most advanced AI systems understand cybersecurity?
We're looking for Offensive Security Analysts to bring real-world attack knowledge to frontier AI development. This role is about structured adversarial reasoning, not exploit development. You'll work with realistic threat scenarios to help AI systems learn how attacks unfold, where defenses break down, and how risk propagates across modern infrastructure.
This is a fully remote, flexible contract role built for security professionals who think offensively but want to apply that expertise in a new and impactful way.
  • Organization
    : Alignerr
  • Type
    : Hourly Contract
  • Location
    : Remote
  • Commitment
    : 10-40 hours/week
What You'll Do
  • Analyze attack paths, kill chains, and adversary strategies across realistic, production-style environments
  • Identify and classify weaknesses, misconfigurations, and defensive gaps
  • Review red-team scenarios and intrusion narratives for accuracy, completeness, and adversarial realism
  • Generate, label, and validate adversarial reasoning data used to train and evaluate AI systems
  • Clearly articulate attack chains, impact, and risk tradeoffs in structured formats
  • Work independently and asynchronously on task-based assignments at your own pace
Who You Are
  • 2+ years of hands-on experience in penetration testing, red teaming, or a blue-team role with deep attack knowledge
  • You understand how real attacks unfold in production environments - not just theory
  • Able to break down complex attack chains and explain them clearly in writing
  • Detail-oriented, methodical, and comfortable working without hand-holding
  • No exploit development skills required - this role is about reasoning, analysis, and structured thinking
Nice to Have
  • Experience with threat modeling, adversary simulation, or attack surface analysis
  • Familiarity with frameworks like MITRE ATT&CK, Cyber Kill Chain, or OWASP
  • Background in security architecture, incident response, or threat intelligence
  • Prior experience reviewing or annotating technical content for quality or training purposes
Why Join Us
  • Work directly on frontier AI projects alongside leading AI research labs
  • Fully remote and flexible - work when and where it suits you
  • Freelance autonomy with meaningful, intellectually engaging work
  • Apply your offensive security expertise to a domain that's actively shaping the future of AI
  • Potential for ongoing work and contract extension as new projects launch

Apply