Pentest Operations Engineer

Kaseya is the leading provider of complete IT infrastructure and security management solutions for Managed Service Providers (MSPs) and internal IT organizations worldwide powered by AI. Kaseya’s best-in-breed technologies allow organizations to efficiently manage and secure IT to drive sustained business success. Kaseya has achieved sustained, strong double-digit growth over the past several years and is backed by Insight Venture Partners www.insightpartners.com), a leading global private equity firm investing in high-growth technology and software companies that drive transformative change in the industries they serve.

Founded in 2000, Kaseya currently serves customers in over 20 countries across a wide variety of industries and manages over 15 million endpoints worldwide. To learn more about our company and our award-winning solutions, go to www.Kaseya.com and for more information on Kaseya’s culture, please click here: Kaseya Culture.

Kaseya is not your typical company. We are not afraid to tell you exactly who we are and our expectations. The thousands of people that succeed at Kaseya are prepared to go above and beyond for the betterment of our customers.

Pentest Operations Engineer

About Us

We’re a leading software company creating cutting-edge solutions for Managed Services Providers (MSPs). Our flagship product, vPenTest, developed by Vonahi Security, is transforming how organizations conduct network penetration testing through automation. As we expand, we’re seeking a highly motivated Pentest Operations Engineer to help ensure our automated penetration tests continue to run reliably and efficiently at scale.

Role Overview

The Pentest Operations Engineer is a hybrid role that blends Level 3 technical support with backend operational engineering. You’ll work closely with our Development, DevSecOps, and Penetration Testing teams to ensure that automated penetration tests initiated through vPenTest are consistently executed as expected — even across complex infrastructure and edge cases.

This is a hands-on, backend-focused role ideal for someone who is naturally curious, highly analytical, and thrives on reverse engineering and problem-solving. Strong communication and collaboration are key, as you’ll be the bridge between multiple technical teams troubleshooting intricate issues behind the scenes.

Key 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.
  
  

Required Skills & Experience

• 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.
• Prior experience in a backend operations, network or systems engineering is a plus.
  
  

Preferred Qualifications

• Experience working with penetration testing tools, automation, or security orchestration.
• Relevant certifications like OSCP, CEH, or CompTIA Security+.
• Exposure to SaaS products.
  
  

Why Join Us?

• Help shape the future of automated security testing.
• Work with a passionate, highly technical team committed to innovation.
• Enjoy competitive compensation, benefits, and flexible work arrangements.
  
  

Join the Kaseya growth rocket ship and see how we are #ChangingLives !

Additional Information

Kaseya provides equal employment opportunity to all employees and applicants without regard to race, religion, age, ancestry, gender, sex, sexual orientation, national origin, citizenship status, physical or mental disability, veteran status, marital status, or any other characteristic protected by applicable law.