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Penetration Testing Engineer - Network Security

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Evolvesec
Full Time position
Listed on 2026-01-25
Job specializations:
  • IT/Tech
    Cybersecurity, Systems Engineer
  • Engineering
    Cybersecurity, Systems Engineer
Job Description & How to Apply Below

Overview

The Penetration Testing Engineer – Network Security is a hands-on client facing offensive security role responsible for executing network, cloud, and adversary-emulation engagements under established methodologies. This role goes beyond point-in-time vulnerability testing and actively contributes to red team and purple team operations, including social engineering, attack-path validation, and defensive collaboration.

Penetration Testing Engineers work closely with senior testers, red team leads, detection engineers, and clients to identify exploitable weaknesses, simulate real-world threat actor behavior, and validate security controls. This role is ideal for practitioners with a strong networking foundation who are ready to operate as adversaries while contributing to high-quality reporting and continuous improvement of testing capabilities.

Typical Experience
  • 3–5 years of experience in IT, cybersecurity, or offensive security
  • Prior exposure to penetration testing, red team activities, SOC collaboration, or adversary emulation
  • Experience performing internal, external, or cloud network security assessments
Core Responsibilities Network & Infrastructure Penetration Testing
  • Execute internal and external network penetration tests, including attack-path discovery and privilege escalation
  • Perform port scanning, service enumeration, and network mapping using industry-standard tools
  • Identify and validate misconfigurations, weak authentication, segmentation failures, and trust boundary issues
  • Assess on-prem and cloud network architectures (AWS, Azure, hybrid environments)
Red Team & Purple Team Operations (Required)
  • Participate in red team engagements simulating real-world adversaries
  • Execute TTP-driven attacks aligned to frameworks such as MITRE ATT&CK
  • Support purple team exercises by collaborating with defensive teams to:
    • Validate detections
    • Tune alerts
    • Measure defensive coverage
  • Provide clear attacker-perspective feedback to blue teams and security leadership
Social Engineering (Required)
  • Support and/or execute social engineering campaigns, including:
    • Phishing (email-based and credential harvesting)
    • Vishing and pretexting (as authorized)
    • Physical security testing support (where in scope)
  • Assist in campaign planning, execution, and ethical handling of sensitive data
  • Document social engineering outcomes with clear business and risk context
Reporting & Communication
  • Draft clear, accurate technical findings with reproduction steps and evidence
  • Contribute to executive summaries that explain risk, impact, and attack feasibility
  • Communicate findings effectively to:
    • Technical teams
    • Defensive stakeholders
    • Non-technical leadership
  • Support remediation validation and re-testing activities
Tooling & Continuous Improvement
  • Use and help improve offensive tooling, scripts, and testing infrastructure
  • Support automation efforts for discovery, enumeration, and validation
  • Continuously develop skills in network attacks, cloud security, and adversary techniques
Technical Skills & Knowledge Required Technical Skills
  • Strong understanding of:
    • TCP/IP, routing, DNS, DHCP
    • Network segmentation and trust boundaries
  • Hands-on experience with:
    • Port scanning and enumeration (e.g., Nmap)
    • Vulnerability identification and validation
  • Familiarity with common network attack vectors:
    • Weak credentials
    • Misconfigured services
    • Excessive trust and lateral movement paths
  • Working knowledge of firewalls, VPNs (IPSec/SSL), and access controls
  • Basic scripting for automation (Bash, Python, or Power Shell)
Cloud & Hybrid Environments
  • Navigating cloud platforms (AWS and/or Azure)
  • Understanding:
    • Security groups / NSGs
    • IAM users, roles, and policies
    • Storage services (S3, Blob Storage)
  • Identifying cloud-specific misconfigurations and exposure risk
Red / Purple Team & Social Engineering Requirements

This role requires demonstrated interest or experience in:

  • Adversary emulation and red team testing
  • Purple team collaboration with SOC and detection teams
  • Social engineering techniques and ethical execution
  • Translating attacker actions into defensive improvement opportunities

Candidates should be motivated to think like attackers while improving organizational resilience.

Soft Skills & Professional Expectations
  • S…
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