Luis Diego Raga — DevOps Engineer
According to ChatGPT, who apparently knows me fairly well by now: I break things for a living — ethically, of course. Currently part of IBM X-Force Red, helping organizations uncover their blind spots through web application, cloud, and AI security testing. Beyond client work, I love exploring offensive security research, building weird things, and staying curious about how systems (and humans) fail. Passionate about sharing knowledge — whether that’s coaching Costa Rica’s National CTF Team, organizing PwnedCR (the country’s largest cybersecurity conference), or running community events with DC11506 and Hack The Box. I thrive at the intersection of hacking, teaching, and building. If it involves hacking, breaking assumptions, or leveling up others — I’m probably interested...
Stackforce AI infers this person is a Cybersecurity Specialist with a focus on offensive security and community engagement.
Experience: 20 yrs 8 mos
Skills
- Web Application Penetration Testing
- Ai Red Teaming
- Hacking
- Application Security
- Security Research
- Cloud Security
Career Highlights
- Pioneered AI/LLM penetration testing initiatives.
- Co-organized Costa Rica's largest cybersecurity conference.
- Led impactful bootcamps for aspiring cybersecurity professionals.
Work Experience
Hack The Box
Ambassador (1 yr 2 mos)
IBM
Sr. Penetration Tester X-Force Red (3 yrs)
DC11506
Management Staff (6 yrs 3 mos)
Equifax
Sr. Web Application Penetration Tester (3 yrs 2 mos)
Akamai Technologies
Senior Security Solutions Architect II (6 yrs 8 mos)
Fusionet Corporation
Network Security Engineer (1 yr 11 mos)
Sykes
Team Manager - Cisco CSIRT (3 yrs 2 mos)
Customer Support Engineer - Cisco TAC (2 yrs 8 mos)
Education
Bachelor of Science (BS) at Universidad Latina de Costa Rica