Senior Penetration Engineer (Red Team Lead)

Shamrock Trading Corporation is a family of brands that has been serving the transportation and logistics industries since 1986. Shamrock offers factoring solutions, export financing, third-party logistics, a fuel card program and trucking technology.

Shamrock’s mission since the start has been to create value and success for our customers, our partners and our people. Strong ethics, dedication to our customers and close attention to the marketplace are critical to the success and growth of the Shamrock brands. Shamrock is headquartered in Overland Park, Kansas, with multiple offices throughout the U.S. Overland Park is a great place to live, work and play, being conveniently located within driving distance of everything Kansas City has to offer. Housed within the heart of Overland Park, our offices include 4 gorgeous towers on the East and West sides of Metcalf Ave. With a heavy community presence and a winning culture, Shamrock is a great place to work in Overland Park!

Why You’ll Love Working Here

Our award-winning culture is a testament to our commitment to growth, recognition and empowerment. From day one, we prioritize employees first, encouraging them to think and act like owners and providing endless opportunities for growth and self-development, both personally and professionally. Shamrock has been recognized as one of America’s 2025 “Most Loved Workplaces” by Newsweek.

Benefits

At Shamrock, we hire bright, ambitious people and give them the tools they need for a successful, long-term career here. Shamrock also offers a premier set of benefits for employees and their families:

• Training and Development: Ongoing training and professional development opportunities
• Medical: Fully paid healthcare, dental and vision premiums for employees and eligible dependents, and gym benefits
• Financial: Generous company 401(k) contributions and employee stock ownership after one year
• Work-Life Balance: Competitive PTO and work from home opportunities after an introductory period

We are seeking a Senior Security Engineer to simulate real-world adversaries and identify high-impact vulnerabilities across enterprise and cloud environments. This role focuses on executing realistic adversary simulations, penetration testing, and attack path analysis, partnering closely with defensive teams to improve detection and response capabilities. The ideal candidate is a hands-on offensive security professional with deep expertise in exploitation, post-exploitation, and adversary tactics.

What You’ll Do

• Plan and execute advanced red team engagements across enterprise environments.
• Emulate real-world threat actors using MITRE ATT&CK-aligned techniques.
• Chain vulnerabilities into realistic attack paths with business impact.
• Simulate multi-stage attacks to evaluate organizational resilience.
• Conduct penetration testing across: Web applications and APIs, cloud environments (IAM abuse, misconfigurations), identity systems (Active Directory / Entra ID) and internal networks and endpoints
• Identify and exploit vulnerabilities to demonstrate real-world risk.
• Perform lateral movement, persistence, and privilege escalation activities.
• Test and bypass security controls and detection mechanisms.
• Operate and customize command-and-control (C2) frameworks: Cobalt Strike, Sliver, Mythic, or equivalent
• Develop scripts, payloads, and tooling to support operations.
• Validate cloud security posture controls through adversarial techniques.
• Exploit identity misconfigurations, exposed credentials, and privilege escalation paths.
• Assess real-world impact of cloud exposure risks.
• Partner with SOC and blue teams to conduct purple team exercises.
• Help improve detection rules, alert quality, and response capabilities.
• Provide insight into attacker techniques to enhance defensive strategies.
• Deliver clear, actionable reports with: Risk-prioritized findings, attack path analysis, and practical remediation guidance
• Translate technical findings into business-relevant risk insights.

• 6-8+ years in offensive security, penetration testing, or red teaming.
• Proven experience executing full-scope red team engagements.
• Strong expertise in: Exploitation (web, network, identity systems), post-exploitation and lateral movement and privilege escalation techniques
• Experience with C2 frameworks and evasion techniques.
• Deep understanding of MITRE ATT&CK framework.
• Strong scripting or programming skills (Python, PowerShell, C#, etc.).

• Experience with cloud penetration testing (AWS, Azure, GCP).
• Background in exploit development or custom tooling.
• Certifications such as OSCP, OSEP, CRTO, OSCE.

We’re so excited to connect with you! If you want to work with forward-thinking people in an award-winning culture, submit your application today.

Having trouble submitting your application? Contact us at [email protected] for support.