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Juan Caillava has worked in a variety of roles in the security and IT fields since 2005. From 2005-2008, they worked as a Teaching Assistant at the Universidad Nacional de Tucumán. In 2007, they worked as a Network Advisory at ARLAB Tecnología Informática. From 2008-2009, they were an Auditing, Analysis and Design at the same university. From 2009-2010, they worked as an Operation & Infrastructure Internship at Scania Argentina S.A., where they were responsible for LAN/WAN network administration, Windows based Server Installation and Administration, and software development. From 2010-2017, they worked as a Senior Specialist at Deloitte Argentina, where they were responsible for external and internal network penetration testing, web application penetration testing, and application source code analysis in C/C++, Java SE/EE, and ASP. Finally, from 2017-2018, they worked as a Senior Security Consultant at Core Security.

Juan Caillava obtained a Computer Engineer degree from the Universidad Nacional de Tucumán in 2009. In 2014, they obtained a CEH certification from the EC-Council. In 2015, they obtained a CISSP certification from (ISC)². In 2016, they obtained an OSCP certification from Offensive Security. In 2017, they obtained an OSCE certification from Offensive Security.