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Penetration Testing Manager Jobs in Chicago, IL (NOW HIRING)

Alliant

Senior Penetration Testing Engineer

Chicago, IL · On-site

$92K - $144K/yr

Perform hands-on penetration testing with a primary focus on web applications and web APIs across ... Present findings and trends to engineering teams, security leadership, and management. * Contribute ...

BDO USA

Senior IT Penetration Tester

Oak Brook, IL · On-site

The Senior Cyber Security Penetration Tester performs offensive security testing for BDO clients ... testing using Burp Suite and related techniques, focusing on authentication, session management ...

BDO

Senior IT Penetration Tester

Oak Brook, IL · On-site

The Senior Cyber Security Penetration Tester performs offensive security testing for BDO clients ... testing using Burp Suite and related techniques, focusing on authentication, session management ...

Spgi

Lead Penetration Test Engineer

Chicago, IL · Hybrid

$135K/yr

Lead Penetration TestEngineer Location: Hybrid 2 days per week onsite on one of our following sites ... testing. Vulnerability Management & Remediation Collaborate with engineering and development teams ...

S&P Global

Lead Penetration Test Engineer

Chicago, IL · Hybrid

$135K/yr

Lead Penetration TestEngineer Location: Hybrid 2 days per week onsite on one of our following sites ... testing. Vulnerability Management & Remediation Collaborate with engineering and development teams ...

UL Solutions

Senior Penetration Tester

Northbrook, IL · On-site

Conduct web application penetration testing (covering OWASP Top 10, API security, authentication ... management (IAM), network security, container/Kubernetes security, serverless architectures ...

Crowe LLP

Offensive Security Manager

Oakbrook Terrace, IL

$111K - $150K/yr

In management at Crowe, you play a pivotal role in leading teams, guiding project execution, and ... Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming ...

Crowe LLP

Offensive Security Manager

Chicago, IL · On-site

$114K - $154K/yr

In management at Crowe, you play a pivotal role in leading teams, guiding project execution, and ... Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming ...

Crowe LLP

Offensive Security Manager

Chicago, IL · On-site

$114K - $154K/yr

In management at Crowe, you play a pivotal role in leading teams, guiding project execution, and ... Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming ...

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Penetration Testing Manager information

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$58.7K

$137K

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How much do penetration testing manager jobs pay per year?

As of Sep 4, 2026, the average yearly pay for penetration testing manager in Chicago, IL is $136,970.00, according to ZipRecruiter salary data. Most workers in this role earn between $114,300.00 and $154,500.00 per year, depending on experience, location, and employer.

What does a penetration testing manager do?

A Penetration Testing Manager oversees teams that simulate cyberattacks on an organization's systems, networks, and applications to identify vulnerabilities and assess security risks. They are responsible for planning, coordinating, and ensuring the quality of penetration tests, as well as communicating findings to stakeholders and recommending remediation strategies. Additionally, they often develop testing methodologies, manage team performance, and ensure compliance with industry standards and regulations.

What are some common challenges faced by a penetration testing manager when leading a security assessment team?

Penetration Testing Managers often face the challenge of balancing technical depth with project management responsibilities. Coordinating multiple engagements, ensuring consistent testing methodologies, and managing client expectations can be demanding. Additionally, staying updated with evolving threat landscapes and ensuring the team has the necessary skills and certifications are ongoing concerns. Effective communication with both technical staff and non-technical stakeholders is crucial for translating findings into actionable recommendations.

What are the key skills and qualifications needed to thrive as a penetration testing manager, and why are they important?

To thrive as a Penetration Testing Manager, you need deep expertise in cybersecurity, vulnerability assessment, and penetration testing methodologies, typically supported by a relevant degree and certifications like OSCP or CISSP. Familiarity with tools such as Metasploit, Burp Suite, and SIEM systems is essential for effectively managing testing operations. Strong leadership, communication, and project management skills help in guiding teams and translating technical findings for stakeholders. These capabilities are crucial to ensure robust security postures, clear risk communication, and successful management of security testing initiatives.

What is the difference between Penetration Testing Manager vs Penetration Tester?

AspectPenetration Testing ManagerPenetration Tester
CertificationsOSCP, CISSP, PMPOSCP, CEH, GPEN
Work EnvironmentOversees teams, manages projects, strategic planningConducts security assessments, performs testing, technical execution
Employer & Industry UsageSecurity firms, large corporations, government agenciesSecurity teams, consulting firms, internal security departments

The main difference is that a Penetration Testing Manager focuses on managing teams, planning projects, and strategic oversight, while a Penetration Tester is hands-on, performing security assessments and testing systems. Both roles require relevant certifications and are integral to cybersecurity, but they differ in responsibilities and scope.

What are the most commonly searched types of Penetration Testing jobs in Chicago, IL?

The most popular types of Penetration Testing jobs in Chicago, IL are:

What are popular job titles related to Penetration Testing Manager jobs in Chicago, IL?

For Penetration Testing Manager jobs in Chicago, IL, the most frequently searched job titles are:

What job categories do people searching Penetration Testing Manager jobs in Chicago, IL look for?

The top searched job categories for Penetration Testing Manager jobs in Chicago, IL are:

Penetration Testing Manager jobs near you
Infographic showing various Penetration Testing Manager job openings in Chicago, IL as of August 2026, with employment types broken down into 71% Full Time, and 29% Part Time. Highlights an 67% In-person, and 33% Hybrid job distribution, with an average salary of $136,970 per year, or $65.9 per hour.

Senior Penetration Testing Engineer

Alliant

Chicago, IL • On-site

$92K - $144K/yr

Full-time

Medical, Dental, Vision, Retirement

Re-posted 28 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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