Pentest Operations Engineer

Summary

Join Kaseya, a leading software company, as a Pentest Operations Engineer and help shape the future of automated security testing. This hybrid role blends Level 3 technical support with backend operational engineering, requiring collaboration with multiple technical teams. You will ensure the reliable execution of automated penetration tests through vPenTest, monitor internal tools for failures, troubleshoot complex issues, work with developers on debugging, and collaborate with DevSecOps. The role demands strong analytical thinking, reverse engineering skills, and excellent communication. Kaseya offers competitive compensation, benefits, and flexible work arrangements.

Requirements

• Strong foundation in infrastructure, networking, and cybersecurity concepts
• Proficiency in Linux environments and experience with cloud platforms (AWS, Azure, or GCP)
• Familiarity with containerization (Docker, Kubernetes) and backend service troubleshooting
• Ability to read and debug code (Ruby on Rails preferred, Python also valuable)
• Excellent analytical thinking and a strong aptitude for reverse engineering complex issues
• Effective written and verbal communication skills

Responsibilities

• Ensure the reliable execution and completion of automated penetration tests initiated through the vPenTest backend
• Monitor internal tools, logs, and metrics to detect and respond to test-related failures or abnormalities
• Troubleshoot complex issues spanning infrastructure, network communication, test orchestration, and backend services
• Work with developers to log issues, assist in debugging, and verify fixes related to the pentest execution pipeline
• Collaborate with DevSecOps to troubleshoot and investigate issues related to the automated pentest framework
• Communicate with the engineering team to align system behavior with testing methodologies and expected outcomes
• Create and maintain internal documentation for issue patterns, resolutions, and troubleshooting workflows

Preferred Qualifications

• Prior experience in a backend operations, network or systems engineering is a plus
• Experience working with penetration testing tools, automation, or security orchestration
• Relevant certifications like OSCP, CEH, or CompTIA Security+
• Exposure to SaaS products

Benefits

Competitive compensation, benefits, and flexible work arrangements