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Entry Level Offensive Security Engineer Jobs in Chicago, IL

US Bank

AI Red Team Lead Engineer

Chicago, IL · On-site

$105K - $139K/yr

The AI Red Team Lead Engineer leads the execution and evolution of offensive security activities focused on AI/ML systems, platforms, and integrations, in addition to traditional enterprise attack ...

The LaSalle Group

Android Engineer

Chicago, IL · On-site

$140K - $160K/yr

Knowledge of security best practices for mobile applications Compensation & Benefits * Base Salary ... entry-level positions to the C-suite. With units specializing in Accounting and Finance ...

Heico

Sustaining Engineer

Chicago, IL

$94K - $116K/yr

... security. We are located on the Northwest side of Chicago and currently have an opening for a ... Bachelor of Science in Mechanical Engineering (BSME) * Entry level to 3 years work experience.

HEICO

Sustaining Engineer

Chicago, IL

$94K - $116K/yr

... security. We are located on the Northwest side of Chicago and currently have an opening for a ... Bachelor of Science in Mechanical Engineering (BSME) * Entry level to 3 years work experience.

HEICO

Sustaining Engineer

Chicago, IL · On-site

$94K - $116K/yr

... security. We are located on the Northwest side of Chicago and currently have an opening for a ... Bachelor of Science in Mechanical Engineering (BSME) * Entry level to 3 years work experience.

ABM

Entry Level Building Engineer

Chicago, IL · On-site

$28 - $31/hr

The Building Engineer must exhibit outstanding client service and professionalism in all ... Department of Homeland Security E-Verify program. E-Verify is an internet-based system used to ...

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Entry Level Offensive Security Engineer information

See Chicago, IL salary details

$63.4K

$157.4K

$211.7K

How much do entry level offensive security engineer jobs pay per year?

As of Jul 28, 2026, the average yearly pay for entry level 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 Entry Level Offensive Security Engineer vs Penetration Tester?

AspectEntry Level Offensive Security EngineerPenetration Tester
CertificationsCompTIA Security+, CEH (Certified Ethical Hacker)CEH, OSCP (Offensive Security Certified Professional)
Work EnvironmentSecurity teams, cybersecurity firms, internal security departmentsConsulting firms, security companies, freelance engagements
Job FocusIdentify vulnerabilities, develop attack simulations, improve security posturePerform targeted security assessments, exploit vulnerabilities, report findings

Both roles involve assessing security weaknesses, often requiring similar certifications like CEH. An Entry Level Offensive Security Engineer typically works within organizations to strengthen defenses, while a Penetration Tester often conducts external assessments for clients. The main difference lies in their scope: engineers focus on proactive security development, whereas testers focus on identifying vulnerabilities through simulated attacks.

What are the key skills and qualifications needed to thrive as an Entry Level Offensive Security Engineer, and why are they important?

To thrive as an Entry Level Offensive Security Engineer, you need a solid understanding of network protocols, cybersecurity fundamentals, and common vulnerabilities, often supported by a bachelor's degree in computer science or a related field. Familiarity with penetration testing tools like Metasploit, Burp Suite, and knowledge of operating systems such as Linux is essential, and entry-level certifications like CompTIA Security+ or CEH are commonly valued. Strong analytical thinking, attention to detail, and effective communication skills help you identify security issues and clearly report findings. These competencies are crucial for assessing organizational security, executing ethical hacking tasks, and helping teams proactively defend against cyber threats.

What types of projects or tasks can an Entry Level Offensive Security Engineer expect to work on during their first year?

As an Entry Level Offensive Security Engineer, you will typically assist with vulnerability assessments, penetration testing, and security audits under the guidance of more experienced team members. Your daily tasks might include running automated scans, analyzing results, writing reports, and helping to develop and validate security tools. Collaboration with IT, development, and incident response teams is also common, as you work together to identify and remediate vulnerabilities. These experiences provide a strong foundation for professional growth and may lead to more advanced responsibilities over time.

What is an Entry Level Offensive Security Engineer?

An Entry Level Offensive Security Engineer is a cybersecurity professional who specializes in testing and assessing the security of computer systems, networks, and applications by simulating real-world attacks. Their primary responsibility is to identify vulnerabilities and weaknesses that malicious hackers could exploit. They use tools and techniques such as penetration testing, vulnerability scanning, and social engineering to find and report security issues. These engineers typically work under the guidance of more experienced team members and help organizations strengthen their security posture.
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 Entry Level Offensive Security Engineer jobs in Chicago, IL? For Entry Level Offensive Security Engineer jobs in Chicago, IL, the most frequently searched job titles are:
What job categories do people searching Entry Level Offensive Security Engineer jobs in Chicago, IL look for? The top searched job categories for Entry Level Offensive Security Engineer jobs in Chicago, IL are:
Entry Level Offensive Security Engineer jobs near you
Infographic showing various Entry Level Offensive Security Engineer job openings in Chicago, IL as of July 2026, with employment types broken down into 1% Locum Tenens, 92% Full Time, 4% Part Time, and 3% Contract. Highlights an 88% Physical, 5% Hybrid, and 7% Remote job distribution, with an average salary of $157,379 per year, or $75.7 per hour.

Forward deployed engineer Chicago

Aikido Security

Chicago, IL • On-site

Full-time

Posted 25 days ago

Job description

We're making security suck less for developers.
Security tools haven't kept up with how software is built today. They interrupt teams, slow releases, and turn security into a bottleneck instead of a capability. We built Aikido to change that. Aikido builds developer-first security products that reduce real risk without getting in the way of shipping software. We focus on what actually matters and automate the rest.
We're taking on legacy security tools teams have been stuck with, and we're winning. If you want to help us take market share and build products developers actually enjoy using, you're in the right place.
Founded in 2022 by third-time founders, Aikido has $85M in the bank and a long runway ahead. We're building toward self-securing software. Join an all-star team. Take real ownership. Push boundaries. Build things that matter.
We're looking for a forward-deployed engineer to help enterprise customers successfully deploy and operationalize our newly launched AI-powered pentest product into their environments.
Some deployments run fully on-prem. Others involve hybrid cloud setups, strict security controls, custom integrations, or heavily regulated enterprise environments. You'll own everything from "customer signed" to "deployment running smoothly", helping customers through implementation, debugging issues, and turning problems into product improvements.
Responsibilities
  • Own enterprise deployments end-to-end: from first install to a stable, healthy setup
  • Debug incidents directly in customer environments (Docker, Postgres, networking, agents, etc.)
  • Handle complex enterprise environments: proxies, firewalls, egress rules, internal CAs, air-gapped setups, and custom security requirements
  • Build and adapt integrations when needed (SSO, IdP, internal PKI, custom setups)
  • Guide customers through implementation and initial usage in complex environments
  • Improve deployment and update flows based on what actually breaks in the field
  • Act as the technical bridge between customers and engineering
  • Translate enterprise deployment issues into clear bugs, fixes, and product improvements
  • Investigate agent behavior: debug failures, auth issues, crashes, and unexpected behavior

  • Strong infrastructure and networking fundamentals (Docker, DNS, TLS, proxies, firewalls)
  • Comfortable debugging in Linux environments
  • Able to read Go, TypeScript, or Python to understand issues and trace problems
  • Familiar with how complex enterprise networks behave in practice
  • Basic offensive security knowledge: understand concepts like RCE, SSRF, and session handling
  • Able to interpret logs and debug distributed systems' behavior
  • Strong communication skills
  • Lives in Chicago

Nice to have:
  • Experience with enterprise or on-prem software deployments
  • Familiarity with cloud environments (AWS, Azure, GCP) for hybrid setups
  • Experience with SSO, identity providers, or internal PKI systems
  • Exposure to security tooling or offensive security concepts

What you can expect:
  • High-impact position in a fast-growing company.
  • Competitive salary package.
  • A company that sticks to its values in an open and informal atmosphere (see our culture page on the website for more details).
  • A diverse and inclusive organization that is proud to be an equal-opportunity employer.
  • Flexibility in working hours

We value competencies above all. The qualities of our people are what count, irrespective of gender, religion, ethnic origin, age, sexual orientation, or disability.

Apply