Offensive Security Supervisor

DeepSeas

Offensive Security Supervisor at DeepSeas leading technical delivery and team mentorship. Responsible for managing engagements and developing junior consultants in cybersecurity.

Posted 6/8/2026full-timeRemote • California • 🇺🇸 United StatesMid-LevelSeniorWebsite

Tech Stack

Tools & technologies

AWSAzureCloudGoogle Cloud Platform

About the role

Key responsibilities & impact

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.

Requirements

What you’ll need

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

Benefits

Comp & perks

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!
- 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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

penetration testingcloud securityAWSAzureGCPAI security testingtechnical report writingmentoringoffensive security

Soft Skills

team leadershipcommunicationorganizational skillsfeedback deliverymentoring

Certifications

OSCPPNPTOSEPCRTOCRTEBSCP