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

Tempus

Senior Application Security Engineer

Chicago, IL · On-site

$130K - $180K/yr

Tempus is seeking a Senior Application Security Engineer with deep expertise in penetration testing to lead efforts in identifying and remediating vulnerabilities across web, mobile, and medical ...

Tempus

Senior Application Security Engineer

Chicago, IL · On-site

$130K - $180K/yr

Tempus is seeking a Senior Application Security Engineer with deep expertise in penetration testing to lead efforts in identifying and remediating vulnerabilities across web, mobile, and medical ...

Bank of America

Senior Manual Ethical Hacker

Chicago, IL · On-site

$103K - $132K/yr

Knowledge of network and Web related protocols/technologies (e.g., UNIX/LINUX, TCP/IP, Cookies) * Experience with vulnerability assessment tools and penetration testing techniques. * Solid ...

Shiro Technologies

Cybersecurity Engineer

Chicago, IL · On-site

... Rapid7 Web Application Security, penetration testing, bug bounty, etc. In other words, our security engineers are partners to software engineers who require accurate information on why a ...

New

Crowe LLP

Offensive Security Manager

Oakbrook Terrace, IL · On-site

$111K - $150K/yr

Web application penetration testing * Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming/Threat emulation * Purple teaming * Evaluate and test IT controls, ...

New

Crowe LLP

Offensive Security Manager

Chicago, IL · On-site

$114K - $154K/yr

Web application penetration testing * Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming/Threat emulation * Purple teaming * Evaluate and test IT controls, ...

New

Crowe LLP

Offensive Security Manager

Chicago, IL · On-site

$114K - $154K/yr

Web application penetration testing * Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming/Threat emulation * Purple teaming * Evaluate and test IT controls, ...

New

Socket.dev

Offensive Security Senior Consultant

Chicago, IL · On-site

$81 - $159/hr

Web application penetration testing * Wireless penetration testing * Social engineering (phishing, telephone, onsite) * Red teaming/Threat emulation * Purple teaming * Evaluate and test IT controls, ...

New

Bank of America

Manual Ethical Hacker

Chicago, IL · On-site

Knowledge of network and Web related protocols/technologies (e.g., UNIX/LINUX, TCP/IP, Cookies) * Experience with vulnerability assessment tools and penetration testing techniques * Solid programming ...

Tempus AI

Senior Application Security Engineer

Chicago, IL · On-site

$118K - $161K/yr

Responsibilities : • Conduct penetration tests on web, mobile, and software medical device ... Required : • 5+ years of proven experience in penetration testing. • Strong understanding of ...

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Showing results 21-40

All JobsWeb Penetration Testing JobsWeb Penetration Testing Jobs in Chicago, IL

Web Penetration Testing information

See Chicago, IL salary details

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How much do web penetration testing jobs pay per hour?

As of Aug 21, 2026, the average hourly pay for web penetration testing in Chicago, IL is $60.83, according to ZipRecruiter salary data. Most workers in this role earn between $52.79 and $68.89 per hour, depending on experience, location, and employer.

What is web penetration testing?

Web penetration testing is a security assessment process where ethical hackers simulate cyberattacks on a website or web application to identify vulnerabilities and weaknesses. The goal is to find and fix security flaws before malicious hackers can exploit them. This process involves testing for issues such as SQL injection, cross-site scripting (XSS), authentication problems, and insecure configurations. The results help organizations strengthen their web security and protect sensitive data from breaches.

What are the key skills and qualifications needed to thrive as a web penetration tester?

To excel as a Web Penetration Tester, you need a solid understanding of web application security, networking protocols, and common vulnerabilities, often supported by a degree in computer science or a related field. Familiarity with tools like Burp Suite, OWASP ZAP, Metasploit, and relevant certifications such as OSCP or CEH is typically required. Strong analytical thinking, attention to detail, and effective communication skills help testers identify risks and clearly report findings to technical and non-technical stakeholders. These competencies are crucial for uncovering security flaws, ensuring robust defenses, and helping organizations mitigate potential cyber threats.

What are some common challenges faced by web penetration testers during assessments, and how can they be addressed?

Web penetration testers often encounter challenges such as limited access to required testing environments, incomplete or outdated documentation, and rapidly evolving web technologies that demand continuous learning. Additionally, testers must balance thoroughness with time constraints and ensure clear communication with development and security teams. Addressing these challenges involves proactive coordination with stakeholders, staying updated with industry tools and vulnerabilities, and maintaining detailed, well-structured reporting to facilitate remediation and collaboration.

What is the difference between Web Penetration Testing vs Web Security Analyst?

AspectWeb Penetration TestingWeb Security Analyst
CertificationsOSCP, CEH, GPENCISSP, CISA, GIAC
Work EnvironmentHands-on testing, simulated attacksMonitoring, policy development, incident response
Employer & Industry UsageCybersecurity firms, tech companies, consultingCorporate IT, financial institutions, government agencies

Web Penetration Testing focuses on actively identifying vulnerabilities through simulated attacks, while Web Security Analysts monitor and improve security measures, analyze threats, and respond to incidents. Both roles require cybersecurity certifications but differ in their approach and daily tasks.

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

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

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

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

Web Penetration Testing jobs near you
Infographic showing various Web Penetration Testing job openings in Chicago, IL as of August 2026, with employment types broken down into 1% As Needed, 84% Full Time, 11% Part Time, 3% Contract, and 1% Nights. Highlights an 88% Physical, 3% Hybrid, and 9% Remote job distribution, with an average salary of $126,535 per year, or $60.8 per hour.

Senior Application Security Engineer

Tempus

Chicago, IL • On-site

$130K - $180K/yr

Full-time

Re-posted 19 days ago

Job description

Passionate about precision medicine and advancing the healthcare industry?

Recent advancements in underlying technology have finally made it possible for AI to impact clinical care in a meaningful way. Tempus' proprietary platform connects an entire ecosystem of real-world evidence to deliver real-time, actionable insights to physicians, providing critical information about the right treatments for the right patients, at the right time.

Tempus is seeking a Senior Application Security Engineer with deep expertise in penetration testing to lead efforts in identifying and remediating vulnerabilities across web, mobile, and medical device applications. You will safeguard sensitive healthcare data and ensure the security of our internal systems and software medical device (SaMD) products, supporting our mission to improve patient outcomes through secure-by-design principles.

Key Responsibilities

  • Execute advanced black-box and grey-box penetration tests on web applications, APIs (REST/GraphQL), and internal systems.

  • Perform deep-dive mobile security assessments on iOS and Android, including reverse engineering and bypassing client-side controls like root detection and certificate pinning.

  • Lead specialized security testing and threat modeling for FDA-regulated medical device software, ensuring compliance with HIPAA, GDPR, and FDA cybersecurity guidelines.

  • Develop high-quality technical reports detailing exploit chains and business logic flaws, providing engineering teams with hands-on remediation guidance.

  • Automate security testing by developing custom tools and scripts in languages such as Python, Go, or PowerShell.

  • Communicate complex security risks and business impacts to executive leadership and cross-functional stakeholders.

  • Mentor junior team members and provide security training to development teams to foster a robust culture of security awareness.

Qualifications

  • 5+ years of experience in penetration testing, ideally within healthcare or highly regulated environments.

  • Expert knowledge of web/API vulnerabilities (OWASP Top 10) and mobile testing frameworks (Frida, Burp Suite, MobSF, Ghidra).

  • Understanding of medical protocols (DICOM, HL7) and cloud security practices (AWS, Azure, or GCP).

  • Proficiency in scripting languages (Python, JavaScript/TypeScript, Go) and secure SDLC practices.

  • Excellent analytical, problem-solving, and interpersonal communication skills.

Preferred Certifications

  • Offensive Security: OSCP, OSCE, or OSWE.

  • Mobile Security: eCMAP or GMOB.

  • General/Regulated: CEH, CSSLP, GPEN, GWAPT, or UL 2900 training.

CHI: $130,000-$180,000

The expected salary range above is applicable if the role is performed from Illinois and may vary for other locations (California, Colorado, New York). Actual salary may vary based on qualifications and experience. Tempus offers a full range of benefits, which may include incentive compensation, restricted stock units, medical and other benefits depending on the position.

We are an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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