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Weekend Offensive Security Engineer Jobs in Chicago, IL

Alliant

Senior Penetration Testing Engineer

Chicago, IL · On-site

$92K - $144K/yr

Perform hands-on offensive security testing to identify, validate, and drive remediation of ... Work with software engineering, application security, and cyber threat mitigation teams to ...

Aikido Security

Forward deployed engineer Chicago

Chicago, IL · On-site

$54.25 - $74.50/hr

Aikido builds developer-first security products that reduce real risk without getting in the way of ... Basic offensive security knowledge: understand concepts like RCE, SSRF, and session handling * Able ...

Spgi

Lead Penetration Test Engineer

Chicago, IL · Hybrid

$135K/yr

We are seeking a Lead Penetration Test Engineer with extensive experience in penetration testing ... This role requires strong offensive security skills combined with cloud and application ...

S&P Global

Lead Penetration Test Engineer

Chicago, IL · Hybrid

$135K/yr

We are seeking a Lead Penetration Test Engineer with extensive experience in penetration testing ... This role requires strong offensive security skills combined with cloud and application ...

Sonoma Consulting Inc.

Security Engineer

Glenview, IL · On-site

This position occasionally requires some weekend and evening work as well as off-hours for on-call support rotation. Description: The Senior Information Security Engineer's responsibilities include:

Bank of America

Manual Ethical Hacker

Chicago, IL

Incorporate threat actors' tactics, techniques, and procedures into offensive security testing ... Detailed technical knowledge in at least 3 of the following areas: security engineering ...

Bank of America

Senior Manual Ethical Hacker

Chicago, IL

$103K - $132K/yr

Incorporate threat actors' tactics, techniques, and procedures into offensive security testing to ... Detailed technical knowledge in at least 5 of the following areas: * security engineering ...

Horizon3.ai

Commercial Sales Engineer

Chicago, IL · On-site

Learn modern cybersecurity concepts, offensive security methodologies, and consultative selling skills from experienced mentors. What You'll Bring * 1-4 years of experience in Sales Engineering ...

Next Step Systems

Network Security Engineer III

Chicago, IL · On-site

$107K - $147K/yr

Network Security Engineer III, Chicago, IL The Network Security Engineer III position is part of a ... and weekend work and local travel in response to needs of the systems being supported ...

McDonald's

Penetration Testing Lead Analyst

Chicago, IL · On-site

... offensive/defensive cybersecurity roles. • 2-3 years of additional experience in related technical cybersecurity roles (e.g. incident response, security operations, detection engineering, etc ...

BDO USA

Senior IT Penetration Tester

Oak Brook, IL · On-site

Uses offensive security tools and techniques to identify, validate, and demonstrate exploitability ... Experience supporting social engineering assessments, such as phishing, vishing, baiting, and ...

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Showing results 21-40

All JobsOffensive Security Engineer JobsWeekend Offensive Security Engineer JobsWeekend Offensive Security Engineer Jobs in Chicago, IL

Weekend Offensive Security Engineer information

See Chicago, IL salary details

$63.4K

$157.4K

$211.7K

How much do weekend offensive security engineer jobs pay per year?

As of Sep 5, 2026, the average yearly pay for weekend offensive security engineer in Chicago, IL is $157,379.00, according to ZipRecruiter salary data. Most workers in this role earn between $147,300.00 and $163,300.00 per year, depending on experience, location, and employer.

What is the difference between Weekend Offensive Security Engineer vs Penetration Tester?

AspectWeekend Offensive Security EngineerPenetration Tester
CertificationsOSCP, CEH, GPENOSCP, CEH, GPEN
Work EnvironmentPart-time, project-based, often remoteFull-time, consulting or in-house roles
Industry UsageSecurity firms, tech companies, freelanceSecurity firms, consulting, internal security teams

The Weekend Offensive Security Engineer and Penetration Tester roles share similar certifications and skills, focusing on identifying vulnerabilities. However, the Weekend Offensive Security Engineer typically works part-time or on a flexible schedule, often remotely, while Penetration Testers usually hold full-time positions. Both roles are vital in cybersecurity, but the engineer role emphasizes a flexible, project-based approach, whereas Penetration Testers often work within organizations or consulting firms on scheduled assessments.

What are the most commonly searched types of Offensive Security Engineer jobs in Chicago, IL?

The most popular types of Offensive Security Engineer jobs in Chicago, IL are:

What are popular job titles related to Weekend Offensive Security Engineer jobs in Chicago, IL?

For Weekend Offensive Security Engineer jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Weekend Offensive Security Engineer jobs in Chicago, IL look for?

The top searched job categories for Weekend Offensive Security Engineer jobs in Chicago, IL are:

What cities near Chicago, IL are hiring for Weekend Offensive Security Engineer jobs?

Cities near Chicago, IL with the most Weekend Offensive Security Engineer job openings:

Weekend Offensive Security Engineer jobs near you
Infographic showing various Weekend Offensive Security Engineer job openings in Chicago, IL as of August 2026, with employment types broken down into 81% Full Time, 16% Part Time, and 3% Contract. Highlights an 92% Physical, 3% Hybrid, and 5% Remote job distribution, with an average salary of $157,379 per year, or $75.7 per hour.

Senior Penetration Testing Engineer

Alliant

Chicago, IL • On-site

$92K - $144K/yr

Full-time

Medical, Dental, Vision, Retirement

Re-posted 29 days ago

Alliant Insurance Services rating

8.7

Company rating: 8.7 out of 10

Based on 23 frontline employees who took The Breakroom Quiz

72nd of 315 rated insurance

Job description

In this hybrid role based at our Chicago Headquarters, you will plan, execute, and report on penetration tests with a focus on web applications and web APIs across both internally developed and vendor SaaS solutions. Perform hands-on offensive security testing to identify, validate, and drive remediation of vulnerabilities in modern application and API architectures. Support targeted testing of related infrastructure, cloud services, and internal systems as needed. Work with software engineering, application security, and cyber threat mitigation teams to strengthen the organization's overall security posture.
Essential Responsibilities
  • Perform hands-on penetration testing with a primary focus on web applications and web APIs across homegrown and vendor systems, support testing of cloud, mobile, and internal systems.
  • Conduct manual and automated testing, including authenticated and unauthenticated attack scenarios.
  • Identify, exploit, and validate vulnerabilities, provide realistic assessments of risk and impact.
  • Develop proof-of-concept exploits and document attack paths when appropriate.
  • Work with development teams to guide remediation efforts, provide recommendations, review fixes, validate resolutions, and retesting.
  • Collaborate proactively with engineering through threat assessments, threat modeling, and "what-could-go-wrong" reviews before code is written.
  • Analyze and prioritize vulnerability findings based on exploitability, severity, and business impact.
  • Produce clear, actionable penetration test reports tailored for technical and non-technical audiences.
  • Present findings and trends to engineering teams, security leadership, and management.
  • Contribute to improving internal testing methodologies, tooling, and standards.
  • Stay current on emerging threats, attack techniques, and best practices relevant to modern web applications, APIs, and cloud environments.

Education & Years of Experience
  • Minimum - 4 Year Bachelors Degree in Computer Science, Cybersecurity, Information Systems or related
  • Minimum - 3 Years of Penetration testing, offensive security or related

In Lieu of Education
  • 6 Years of Penetration testing, offensive security or related

License/Certifications/Training
  • Preferred: Industry certifications such as OSWE, OSCP, OSCE, GPEN, GWAPT, CRTO, or related offensive security credentials

Compensation & Benefits:
Typical hiring range: $92,600.00 to $144,100.00 Annually. Actual compensation will be determined using factors such as experience, skills & knowledge.
Benefits: Alliant provides a benefits package including health care, vision, dental, and 401k with employer match including:
  • Annual performance bonus
  • Work from home up to 3 days a week
  • Paid parental leave
  • Employee discount programs
  • Time off including paid personal and sick days
  • 11 paid holidays
  • Education reimbursement

*Note that eligibility and cost of benefits can vary depending on the number of regularly scheduled hours, and job status such as regular full-time, regular part-time, or temporary employment.
Adhere to and ensure compliance of all business transactions with policy and process of the Bank Secrecy Act. Ensures compliance with all applicable state and federal laws, company procedures and policies. Maintains integrity and ethics in all actions and conversations with or regarding credit union members and their accounts; complies with Privacy Act directives.
The responsibilities listed do not contain a comprehensive listing of activities, duties or responsibilities that are required of the employee for this position. Duties, responsibilities and activities may change at any time with or without notice.
Equal Opportunity Employer
This employer is required to notify all applicants of their rights pursuant to federal employment laws. For further information, please review the Know Your Rights notice from the Department of Labor.

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