alex@portfolio: ~

➜ whoami

Senior Rails Developer · Security Expert · AI Engineer

➜ ssh root@10.10.10.██ -i ~/.ssh/alex

root@pwned:~# cat proof.txt

Two decades of professional software development, with deep roots in Ruby on Rails and a persistent thread of security

through everything — full-stack builds, distributed team lead, zero-downtime migrations, payment-critical infra at PayPal.

Five years at Offensive Security — built the vulnerable machines tens of thousands of security students hacked through.

8,000+ hrs mentoring toward OSCP, OSCE, OSWE, and OSWP.

root@pwned:~# ls /opt/

ollama/

root@pwned:~# ollama run alex:latest "who built you?"

pulling manifest ████████████ 100%

Work Experience

  1. Engineering Manager & DevOps Consultant

    Current

    Greyhat Chile

    Santiago, Chile / Worldwide · August 2018 – Present

    • Led and mentored a Ruby development team, guiding architecture, enforcing coding standards, and supporting developer growth.
    • Migrated 12+ production Rails applications from Ruby 3.2/3.3 to Ruby 3.4.x and Rails 7.x to Rails 8.1.3, managing breaking changes in Active Support, Action Cable, and the Propshaft asset pipeline with zero-downtime deployments.
    • Designed and built a production-grade AI inference service (Python, LangGraph, OpenAI, pgvector) powering automated ticket dispatch, AI summaries, and LLM-as-judge evaluation frameworks with hallucination detection.
    • Implemented AI feature rollouts across a large Rails monolith — dispatch eligibility, priority recommendations, technician assignment suggestions — gated by feature flags and account-level settings with circuit breaker protection.
    • Managed AWS cloud infrastructure via Terraform, implementing IaC and CI/CD pipelines for reliable multi-environment deployments.
    • Implemented monitoring and observability with Datadog, custom alerting, and performance tracking across distributed services.
    • Automated operational workflows through scripting and infrastructure tooling, reducing manual intervention.
    • Actively contribute to AI initiatives as a mentor, guiding developers in the effective and secure integration of AI and LLMs, including practical application of the OWASP LLM Top 10 principles.
    • Executed complex Ruby and Rails migrations with minimal disruption, optimized database indexing and query performance, and migrated monolithic Paperclip storage to ActiveStorage.

  2. Ruby on Rails Developer

    Taller Technologies / Braintree Venmo at PayPal

    Remote / US · July 2021 – December 2021

    • Developed new features for Braintree / Venmo payment applications using Ruby on Rails.
    • Utilized VIM/TMux, Pair Programming, and Python for automation in development workflows.

  3. Vulnerable Machine Engineer / Senior Student Administrator

    Offensive Security LTD

    Remote / Worldwide · February 2016 – June 2021

    Vulnerable Machine Engineer

    • Developed training applications in Ruby on Rails, ReactJS, Laravel, Java Spring, Django, and Node.js with PostgreSQL, MySQL, and MongoDB.
    • Managed AWS servers and provided remote lab administration for Linux, Unix, and Windows.
    • Researched and developed exploit/attack vectors in Python for cybersecurity training.

    Senior Student Administrator

    • Mentored over 8,000 hours, training students for OSCP, OSCE, OSWP, and OSWE certifications, focusing on hands-on techniques.
    • Offered guidance on offensive security methods, best practices, and problem-solving.

  4. Senior Software Engineer

    Bithaus Chile

    Santiago, Chile · July 2015 – January 2016

    • Maintained J2EE applications with PostgreSQL databases as a Senior Java Developer.
    • Administered Amazon EC2 servers and assisted with Datadog monitoring implementation.

  5. Founder / Entrepreneurship

    Alexertech of Alex B.

    Mérida, Venezuela · March 2008 – April 2015

    • Provided Full Stack Development and Training in Java, JSP, PHP, JavaScript, CSS, XML & XSLT, PostgreSQL, MySQL.
    • Developed a virtual classroom for IT Security and Software development courses for over 700 students, with automated student administration.