Senior Penetration Tester

Senior Penetration Tester

Location: Fully Remote

Duration: 3 months contract

About the Rol

eWe are seeking a highly skilled Senior Offensive Security Operator to lead and execute advanced penetration testing engagements across complex multi-cloud enterprise environments. This role combines deep offensive security expertise with AI-driven automation, autonomous testing frameworks, and scalable attack simulation capabilities

.The ideal candidate will be responsible for identifying systemic risks through offensive security assessments, adversary emulation, penetration testing, and security research while building innovative automation solutions that enhance offensive operations

.Key Responsibilitie

sOffensive Security Operation

• sConduct security assessments for mergers, acquisitions, and technology integrations
• .Plan and execute full-scope penetration testing engagements across network, application, cloud, and social engineering domains
• .Perform assume-breach exercises to validate security controls and isolation mechanisms
• .Execute adversary emulation activities aligned with the MITRE ATT&CK framework
• .Lead purple team exercises in collaboration with security operations teams
• .Deliver executive-level presentations and technical reports that clearly communicate business risk and remediation priorities

.AI-Powered Security Automatio

• nDesign and develop autonomous security testing frameworks leveraging AI/ML technologies
• .Build AI-assisted reconnaissance, target enumeration, and attack surface analysis tools using LLMs and custom agents
• .Develop automated penetration testing pipelines for continuous security validation

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• .Create offensive security tools, payload generators, command-and-control frameworks, and evasion techniques that adapt to defensive controls
• .Integrate offensive tooling with enterprise AI platforms and infrastructure
• .Automate vulnerability reporting, ticket creation, and remediation tracking workflows

.Strategic Leadershi

• pHelp define offensive security strategy, roadmaps, and priorities
• .Identify emerging attack surfaces across cloud-native platforms, AI systems, and enterprise applications
• .Participate in architecture reviews, security initiatives, and incident response activities requiring offensive security expertise
• .Monitor emerging threats, vulnerabilities, and adversary tactics relevant to modern enterprise environments

.Research & Innovatio

• nConduct research into emerging attack techniques, AI-assisted exploitation, and cloud security methodologies
• .Contribute to shared automation repositories and offensive security knowledge bases
• .Build and maintain penetration testing infrastructure using Infrastructure-as-Code practices
• .Stay current with industry research, conferences, and offensive security advancements

.Required Qualification

• s4+ years of experience in offensive security, penetration testing, red teaming, or related enterprise security roles
• .Strong expertise in at least three of the following areas
• :Network exploitatio
• nWeb application securit

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• yActive Directory attack
• sCloud infrastructure securit
• ySocial engineerin
• gPhysical security assessment
• sProficiency in Python, Go, C/C++, or similar languages for offensive tool development and automation
• .Experience building automated security testing tools, frameworks, or pipelines
• .Knowledge of Kubernetes, container security, and cloud-native attack methodologies
• .Hands-on experience with command-and-control (C2) frameworks and adversary simulation platforms
• .Strong understanding of the MITRE ATT&CK framework and adversary emulation techniques
• .Experience with AI/ML security, including attacking AI systems, prompt injection, model security, or AI-powered offensive tooling
• .Experience developing autonomous testing agents using large language models (LLMs)
• .Excellent communication skills with the ability to translate technical findings into business-focused recommendations
• .Bachelor's degree in Computer Science, Cybersecurity, or equivalent practical experience

.Preferred Qualification

• sPublished CVEs, security research, blog posts, or conference presentations
• .Experience supporting SaaS or multi-tenant environments handling sensitive customer data
• .Offensive security certifications such as OSCP, OSCE, OSEP, CRTO, GXPN, or equivalent
• .Familiarity with .NET, Java, Kotlin, and legacy application security testing
• .Experience using Infrastructure-as-Code tools such as Terraform or Pulumi