Offensive Security Supervisor

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