Penetration Tester

About the Role

DeepSeas is a leader in cyber defense with 30 years of experience, serving nearly 1,000 clients worldwide, including Fortune 100 enterprises, mid-market organizations, higher education institutions, and government agencies. The Penetration Tester is a practicing offensive security professional who independently executes client engagements across DeepSeas' core service lines. This role represents the transition from emerging practitioner to confident, self-sufficient contributor, owning engagements end-to-end within defined scope and producing client-ready deliverables without heavy oversight.

Responsibilities

• Conduct internal and external network penetration tests including enumeration, exploitation, lateral movement, and post-exploitation within defined scope.
• Perform web application assessments aligned to OWASP Top 10 and API security testing standards.
• Conduct basic cloud security assessments (AWS, Azure, GCP) including misconfiguration identification, IAM review, and exposed services enumeration.
• Bring experience with adversarial engagements such as red team and purple team exercises.
• Support AI/LLM security assessments including prompt injection, model abuse scenarios, and OWASP LLM Top 10 coverage under senior guidance.
• Produce complete, client-ready findings reports with clear technical narratives, reproduction steps, risk ratings, and remediation guidance.
• Participate in client kick-off calls and debrief walkthroughs, communicating findings professionally to technical and non-technical stakeholders.
• Maintain accurate engagement documentation, time tracking, and artifact organization in project management systems.
• Pursue continuous development through assigned training, lab environments, and certification advancement.
• May be required to travel up to 25% of the time.

Candidates must be U.S. citizens and currently reside within the United States.

Requirements

• 2-5 years of professional penetration testing or applied offensive security experience; strong candidates with equivalent demonstrated skills will be considered.
• Proficiency with standard toolsets: Nmap, Metasploit, Burp Suite, Nessus/OpenVAS, BloodHound, or equivalents.
• Solid understanding of networking fundamentals (TCP/IP, DNS, HTTP/S, AD, VPNs) and common vulnerability classes.
• Familiarity with at least one scripting language (Python, Bash, or PowerShell) for basic automation and tooling.
• Exposure to cloud platforms (AWS, Azure, or GCP) and awareness of common cloud misconfiguration patterns.
• Solid understanding of AI technology in everyday work activities.
• Strong written communication with the ability to produce accurate, professional-quality findings documentation.

Preferred Qualifications

• Hands-on penetration testing certification, such as PNPT (TCM Security), OSCP (Offensive Security), CompTIA PenTest+, or eWPT/eJPT with demonstrated experience.

About DeepSeas

At DeepSeas, we prioritize reducing stress while advancing careers and maturing security programs. Our values guide daily behavior and decisions, reflecting the essence of our organization and the personalities of our teammates ("Deeps"). These values include:

• Client obsession
• Standing in solidarity with teammates
• Prioritizing personal health and well-being
• Believing in the power of diversity
• Solving hard problems at the speed of cyber

This role offers the opportunity to join a supportive team and an industry-leading organization that values growth and innovation.

Security Responsibilities

• Understanding and following DeepSeas’s information security policies and procedures.
• Remaining vigilant and reporting any suspicious activity or possible weaknesses in information security.
• Actively participating in efforts to maintain and improve information security.

This position is considered Moderate Risk with potential access to restricted/private client/internal data, which must be treated with sensitivity and in the most secure manner.