Cypress HCM · 18 hours ago
Senior Offensive Security Engineer-Web&AI
Mountain View, CA
Contract
Onsite
Mid, Senior Level
5+ years expCypress HCM is looking for a Senior Offensive Security Engineer to proactively identify, exploit, and help eliminate security weaknesses across their web platforms and AI/ML systems. The role involves conducting offensive security assessments, leading penetration tests, and influencing secure architecture design across the organization.
Human ResourcesInformation TechnologyStaffing Agency
Responsibilities
Conduct offensive security assessments on large-scale web applications, REST APIs, and cloud backed services
Identify and validate vulnerabilities including injection flaws, access control issues, authentication/authorization weaknesses, SSRF, deserialization, and logic bugs
Evaluate LLM-based systems and AI agents for prompt injection, data exfiltration, model abuse and jailbreaks
Design and execute red team–style engagements simulating real-world adversaries
Develop custom exploitation tools, PoCs, and fuzzers for web and AI attack surfaces
Identify systemic security weaknesses and collaborate with engineering teams to drive long term mitigations
Review architectures and designs for new products with an attacker mindset
Produce clear, actionable security reports and present findings to technical and executive stakeholders
Qualification
Required
Master's degree in Computer Science, Computer Engineering, Information Security, or a closely related technical field
5+ years of experience in offensive security, penetration testing, or red teaming
Deep expertise in web application security
Strong understanding of API security
Hands-on experience testing AI/ML or LLM-based systems, or strong motivation with demonstrated research in this area
Proficiency in at least one scripting or programming language (Python, Go, JavaScript, or similar)
Strong knowledge of common exploitation techniques and attacker tooling
Preferred
Doctorate (PhD) in a relevant field is a plus but not required
Prior work on adversarial ML, red-teaming AI systems, or secure LLM pipeline design
Experience with cloud security (AWS, GCP, Azure) and containerized environments
Background in security research, published CVEs, CTF experience, blog posts, or conference talks
OSCP, OSEP, OSWE, CRTO, or similar
Company
Cypress HCM
Cypress HCM is a staffing and recruiting company providing technology and creative recruiting solutions.
51-200 employees
Funding
Current Stage
Growth StageLeadership Team
Mark Lillig
CEO
Philip Oommen
CFO
Company data provided by crunchbase