Pentest Operations Engineer

Summary

Join Kaseya, a leading software company, and become our new Pentest Operations Engineer. This hybrid role combines Level 3 technical support with backend operational engineering, focusing on ensuring the reliable execution of automated penetration tests through our flagship product, vPenTest. You will collaborate with various teams, troubleshoot complex issues, and maintain internal documentation. This hands-on position requires strong analytical and communication skills, along with a solid foundation in infrastructure, networking, and cybersecurity. The ideal candidate will have experience in backend operations, network or systems engineering, and familiarity with penetration testing tools and automation. 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