Luis Diego Raga

DevOps Engineer

Costa Rica20 yrs 8 mos experience
AI EnabledHighly Stable

Key Highlights

  • Pioneered AI/LLM penetration testing initiatives.
  • Co-organized Costa Rica's largest cybersecurity conference.
  • Led impactful bootcamps for aspiring cybersecurity professionals.
Stackforce AI infers this person is a Cybersecurity Specialist with a focus on offensive security and community engagement.

Contact

Skills

Core Skills

Web Application Penetration TestingAi Red TeamingHackingApplication SecuritySecurity ResearchCloud Security

Other Skills

AI/LLM Penetration TestingAdversarial Machine LearningBot ManagementBurp SuiteCloud ComputingCoachingDomain Name System (DNS)Event PlanningMentoringMetasploitOWASPPenetration TestingPublic SpeakingTesting ToolsTraining and Development (HR)

About

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...

Experience

Hack the box

Ambassador

Jan 2025Present · 1 yr 2 mos · Remote

  • As a Hack The Box Ambassador, I help grow and engage the local cybersecurity community by organizing and leading HTB Meetups—collaborative events where participants solve real-world challenges together. I also represent and advocate for Hack The Box at conferences and industry events, promoting hands-on learning and ethical hacking.
HackingMentoringEvent Planning

Ibm

Sr. Penetration Tester X-Force Red

Mar 2023Present · 3 yrs · Costa Rica · Remote

  • Led and executed penetration tests on Web Applications and APIs; served as Tech Lead for a subscription client and SME for the Web Application discipline driving scoping efforts, resolving escalations, and mentoring team members through complex challenges, resulting in improved resolution efficiency and stronger team collaboration.
  • Managed high-profile projects and escalations; pioneered AI/LLM penetration testing across multiple accounts, delivering innovative solutions to enhance client security.
  • Supported hiring efforts through interviews and onboarding; led engaging Web Application Security and Lockpicking Bootcamps for Costa Rica interns, earning outstanding feedback and helping cultivate core technical skills.
  • Represented IBM as a speaker and facilitator at various industry conferences and cybersecurity events.
Web Application Penetration TestingAI Red TeamingAI/LLM Penetration TestingPublic SpeakingPenetration TestingHacking+1

Dc11506

Management Staff

Dec 2019Present · 6 yrs 3 mos · Costa Rica

  • Leadership team member of DC11506, a DEF CON–affiliated cybersecurity and ethical hacking community. Co-organize PwnedCR, the region’s premier annual cybersecurity conference, along with monthly technical meetups.

Equifax

Sr. Web Application Penetration Tester

Dec 2019Feb 2023 · 3 yrs 2 mos · Costa Rica

  • Drove a global security program to identify, exploit, and communicate application and network-layer risks, while supporting mitigation strategy development.
  • Led and executed complex penetration tests and Red/Blue team exercises across business units.
  • Built strong partnerships with Security and IT leaders to enable effective assessments and remediation efforts.
  • Spearheaded integration initiatives between Security and IT teams to align on risk management priorities.
  • Managed reporting to ensure risks were captured, prioritized, and addressed efficiently.
Security ResearchApplication SecurityMetasploitVulnerability ResearchBurp SuiteVulnerability Assessment+1

Akamai technologies

Senior Security Solutions Architect II

Mar 2013Nov 2019 · 6 yrs 8 mos · San Jose, Costa Rica

  • Progressed from Solutions Architect to Senior Solutions Architect II and Subject Matter Expert (SME) over a six-year journey, contributing to Akamai’s Security Services across implementation, research, training, and leadership roles.
  • Security Leadership & SME: Led Akamai’s Attack Reporting Service, producing threat intel and research on emerging attack trends. Served as SME for Bot Manager, driving best practices, training global teams, and advising Engineering and Product teams on improvements.
  • Training & Mentorship: Designed and delivered onboarding and technical training for new hires across Costa Rica, including Solutions Architects and TPMs. Coordinated Ethical Hacking and Web Security bootcamps, CTF events, and ongoing capability development.
  • Client Integrations & Security Solutions: Deployed and optimized Akamai's cloud-based security solutions (WAF, DDoS protection, SiteShield, DNS security) for enterprise, financial, and e-commerce clients.
  • Program & Team Development: Supported strategic hiring initiatives, revamped training programs, and acted as escalation point for complex technical and integration issues.
  • Cross-Functional Collaboration: Worked with global security teams to standardize processes and supported internal programs and initiatives within Global Security & Government Services.
Security ResearchApplication SecurityTesting ToolsOWASPCloud SecurityCloud Computing+4

Fusionet corporation

Network Security Engineer

Apr 2011Mar 2013 · 1 yr 11 mos

  • Deployed, tested, and optimized network technologies for mid-sized to large enterprises, tailoring implementations to meet specific customer requirements.
  • Delivered post-sales support across network security, routing & switching (R&S), and wireless infrastructure.
  • Planned and executed vulnerability assessments and broader security evaluations to identify and mitigate risks.
  • Collaborated with the design team to address technical inquiries and contribute to new network architecture implementations.
  • Developed and delivered internal training sessions to upskill peers and associates, enhancing team knowledge and performance.

Sykes

2 roles

Team Manager - Cisco CSIRT

Promoted

Feb 2008Apr 2011 · 3 yrs 2 mos

  • Led the Costa Rica Event Analysis team (15+ analysts) responsible for analyzing data from Cisco’s corporate and extranet network using SIEM platforms and other monitoring tools to detect, investigate, and respond to security events.
  • Collaborated with escalation teams to resolve complex security incidents requiring in-depth analysis and cross-functional coordination.
  • Managed security monitoring projects, including the deployment of new tools, enhancement of detection capabilities, and development of reporting processes.
  • Performed administrative team lead duties including hiring, training, workload distribution, performance evaluations, and quality assurance—while maintaining strong relationships with internal stakeholders and the client.

Customer Support Engineer - Cisco TAC

Jun 2005Feb 2008 · 2 yrs 8 mos

  • Provided technical support for Cisco VPN and Security solutions, resolving complex customer issues and ensuring high-quality service delivery.
  • Planned and delivered onboarding and technical training sessions for new hires, contributing to team readiness and operational excellence.

Education

Universidad Latina de Costa Rica

Bachelor of Science (BS) — Systems Engineering

Jan 2008Jan 2015

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