Offensive Security Supervisor Department: Offensive Security Employment Type: Full Time Location: Remote - United States Description The Offensive Security Supervisor bridges hands-on technical delivery with day-to-day team leadership. This is a senior individual contributor role does not carry formal people management responsibilities but plays a critical role in keeping the team running smoothly, maintaining quality standards, and developing junior consultants. Supervisors are expected to remain active technical contributors while serving as the first point of escalation for the team during the Manager's absence or when dealing with engagement-level challenges.

Key Responsibilities

Following are the major results needed for success in the role. Additional responsibilities, tasks and duties will be assigned and required as needed. Technical Delivery Independently execute and lead complex engagements across all major DeepSeas Offensive Security service lines, including network, web application, cloud, and AI/LLM security assessments Lead cloud offensive assessments across AWS, Azure, and GCP Lead or support AI/LLM security engagements covering OWASP LLM Top 10 attack classes, agentic system abuse, and AI-integrated application testing Serve as technical lead or QA reviewer on multi-consultant engagements Review and approve Associate and Senior reports before client delivery, ensuring findings accuracy, narrative quality, and executive summary effectiveness Provide technical escalation support when team members encounter novel environments or blocked attack paths Team Mentorship & Day-to-Day Operations Serve as primary day-to-day point of contact for the team handling scheduling conflicts, engagement logistics, and consultant questions Conduct structured technical mentorship with teammates: pairing on engagements, reviewing work, and delivering actionable feedback Run or facilitate weekly team stand-ups, engagement check-ins, and internal knowledge-sharing sessions Track team workload and flag capacity or quality concerns to leadership proactively Coordinate with service leads to maintain and update team methodology documentation, templates, and internal playbooks Assist with onboarding new team members, including tool access, lab orientation, and early-engagement pairing Sales & Client Enablement Participate in scoping and discovery calls, providing technical input to support SOW development Assist in building service-specific collateral, methodology documentation, and capability presentations Serve as a technical reference during sales conversations when needed Experience, Education and Skills Required 5+ years of professional penetration testing experience Hands-on pentest certification required (OSCP, PNPT, or equivalent); advanced certifications (OSEP, CRTO, CRTE, BSCP) strongly preferred Demonstrated offensive experience in cloud environments (AWS, Azure, or GCP) and familiarity with AI/LLM security testing concepts Demonstrated ability to mentor junior practitioners and communicate feedback constructively Strong organizational instincts — comfortable managing multiple concurrent engagement timelines Experience reviewing and editing technical reports to a client-delivery standard Excellent verbal communication; comfortable leading team meetings and client debrief calls Why DeepSeas? At Deep Seas, we like to say that heart rates go down, careers take off, and security programs mature. Our values provide the ultimate guide for our daily behavior and decisions. Without these values, we aren’t Deep Seas. They preserve the essence of our organization, reflect the personalities of our Deeps (how we affectionately refer to our teammates), and enable us to exceed expectations. Our values are: We are client obsessed. We stand in solidarity with our teammates. We prioritize personal health and well-being. We believe in the power of diversity. We solve hard problems at the speed of cyber. This is your chance to join a supportive crew of teammates and an industry-leading organization that values opportunities for growth. If DeepSeas sounds like a good fit for you, send us your resume and let’s talk! Information security is everyone’s 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. DeepSeas considers this position is as Moderate Risk with a potential to view/access/download restricted/private client/internal data. This information must be treated with sensitivity and in the most secure manner. HR reserves the right to perform random background/drug screens to ensure the safety of client/DeepSeas data