Penetration Tester

DeepSeas owns cyber risk for its clients: autonomously, continuously, and with proof. The company brings securitytechnology, threat intelligence, and expert practitioners together to deliver coordinated cyber defense, helpingorganizations strengthen protection while reducing the work required of their internal teams.

Combining agentic AI with human judgment, DeepSeas automates threat analysis and response within client-define boundaries, continuously improves defenses through threat hunting and detection engineering, and provides visibility into investigations, actions taken, and service performance. Its technology-agnostic approach works with the security investments clients already have.

DeepSeas connects 24/7 managed detection and response with offensive security, vulnerability management, governance, risk and compliance, CISO advisory, and incident response. With 30 years of experience in cyber defense, DeepSeas is trusted by nearly 1,000 clients around the world, including Fortune 100 enterprises and mid-market organizations. Its team of more than 250 cybersecurity professionals serves clients across 30+ countries.

Frost & Sullivan recognized DeepSeas as an Innovation Index standout in its 2025 Frost Radar™ for ManagedDetection and Response and awarded the company its 2024 Competitive Strategy Leadership Award in the global MDR market.

Defend Like You Know What’s Coming™

Learn more at deepseas.com.

Position Summary

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

Experience, Education, and Skills Required

Minimum 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

• Interest in cybersecurity, technology, or B2B marketing.
• Familiarity with social media management tools, HubSpot or another marketing automation platform, or Canva or Adobe Creative Suite.
• Basic knowledge of SEO, web content management, or marketing analytics.
• Prior marketing internship, campus organization, or freelance marketing experience.
• A portfolio or writing samples.

Information Security Responsibility

Information security is everyone's responsibility. This includes:

• 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.

Why DeepSeas?

• Join a strong, profitable industry leader in one of the highest-growth industries around.DeepSeas
• Make a direct impact on both our clients' security programs and our company culture — your opinions matter and are heard.
• 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.
• Flexible work schedule and casual work environment.
• 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.