About the role

Senior Penetration Testing Associate conducting penetration tests at cybersecurity firm Drawbridge. Collaborating with clients to assess security and improve defenses against cyber threats.

Responsibilities

Conduct internal and external penetration tests across diverse client environments.
Qualify testing requirements and scope engagements with clients.
Troubleshoot and resolve testing issues independently.
Present detailed assessment reports and findings directly to clients.
Consult with clients regarding remediation strategies and best practices.
Act as an escalation point for analysts and associates, providing technical guidance and mentorship.
Manage test scheduling and set client timing expectations to ensure smooth project delivery.
Serve as a technical consulting resource for both internal teams and external clients.
Lead penetration testing efforts against Drawbridge systems and other critical infrastructure.
Perform customized tests for clients, including physical assessments, laptop testing, remote access testing, and cloud environment evaluations.
Create and update relevant internal documentation, ensuring accuracy and completeness.
Develop repeatable and teachable processes for performing various testing tasks.
Assist in improving the organization’s penetration test offerings, including reporting and process enhancements.
Lead breach response discussions and provide advisory services during incident response engagements.

5+ years of offensive security experience, with a focus on penetration testing.
Deep knowledge of penetration testing principles, tools, and techniques (e.g., Metasploit, Burp Suite, etc.).
Ability to identify systemic security issues based on vulnerability and configuration analysis.
Experience with Linux and Windows operating systems.
Strong working knowledge of networking concepts and attack stages (footprinting, scanning, enumeration, gaining access, privilege escalation, maintaining access, network exploitation, covering tracks).
Excellent written and verbal communication skills, with the ability to present findings to technical and non-technical audiences.
Strong ability to prioritize, organize, and multi-task in a fast-paced environment.
Experience mentoring junior team members and acting as a technical escalation point.
Excellent written and verbal communication skills.
Excellent time management skills.
Nice if you have experience with IT infrastructure, cloud technology, business continuity, disaster recovery, and incident response.
Knowledge of hedge fund, private equity, or RIA operations/compliance.
Industry certifications (e.g., OSCP, GPEN, CEH).
Experience with Python or comparable scripting language.