[Hiring] Penetration Tester @DeepSeas

Role Description

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. Penetration Testers own their engagements end-to-end within defined scope, produce client-ready deliverables without heavy oversight, and are developing the depth and breadth needed to tackle increasingly complex environments. This is the primary delivery role on the team and the foundation of the practice’s capacity.

Key Responsibilities

• Technical Delivery
  • 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 offensive security assessments of cloud environments, including exploitation of misconfigurations, IAM abuse, and privilege escalation, plus configuration audits that turn findings into prioritized remediation guidance.
  • 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.
• Reporting & Client Communication
  • 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.
• Professional Growth & Travel
  • Pursue continuous development through assigned training, lab environments, and certification advancement.
  • May be required to travel up to 25% of the time.

Qualifications

• 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.
• Deep understanding of 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.

Information Security Responsibility

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

Benefits

• Competitive benefits package including full healthcare, dental, vision, PTO, Sick Leave, Personal Choice Holidays, Life/Accident Insurance, 401(k) with company matching, and Company Bonus.
• Flexible work schedule and casual work environment.
• A collaborative culture that respects and appreciates you for your unique skills.
• A tight-knit team that supports you in doing your best work while enjoying your work life.
• Hands-on exposure to B2B marketing in the fast-moving cybersecurity industry.
• Variety of projects — you won't get bored.