Joey Yakimowich-Payne

Joey Yakimowich-Payne

AI Red Teamer & Security Researcher
@Jojomaw • Edmonton, AB, Canada
#4 Global Rank GraySwan
1,024 Challenges Completed
3x HackAPrompt Champion
5,424+ Attack Chats

About

Joey is a security researcher and builder who specializes in breaking AI models and engineering the systems that power them. With over a decade of software experience and a top-tier global ranking in adversarial research, he bridges the gap between high-stakes red teaming and production-grade development. Currently an AI Security Specialist at Trajectory Labs, pursuing further studies at NAIT.

Red Teaming

Professional Security Consulting

Browser Extension Vulnerability Assessment
Target: Frontier AI Model (Under NDA)

Conducted comprehensive red teaming on an AI-powered browser extension, identifying critical architectural flaws in system prompt enforcement. Achieved high Attack Success Rates for data exfiltration and credential harvesting via novel conversation history manipulation techniques. Built custom proxy tooling to intercept and analyze API traffic patterns.

Conversation History Attacks mitmproxy Python Network Analysis
Spreadsheet Extension Injection Analysis
Target: Frontier AI Model (Under NDA)

Discovered a character encoding vulnerability enabling silent conversation history injection in an AI spreadsheet assistant. Developed universal injection payloads that manipulated sensitive data without user detection and exfiltrated information to external endpoints while the model presented benign output to the user.

Encoding Exploits Prompt Injection Data Exfiltration

Competition Results

1st
Pliny The Prompter x HackAPrompt (Team: Finally Together)
318,905 pts, 11/12 Challenges
1st
Hawaiian Havoc (Solo)
119,388 pts, 5/5 Challenges
1st
PointCrow's Speed Run (Team: ADHRD)
49,988 pts, 10/10 Challenges
#3
CBRNE Bonus (Solo)
Top 5 Finish
#5
CBRNE (Team: Tinglelings)
48,637 pts, Top 5 Finish
#4
MATS x TRAILS (Team: Operation Chimera)
Top 5 Finish

0din Bug Bounty Program

Earned 5 accepted bounties for model guardrail jailbreaks, all receiving maximum scores (91-100). Successfully bypassed copyright filters and content safety guardrails across multiple frontier models with consistently high effectiveness ratings.

Techniques & Arsenal

Adversarial Prompt Engineering Indirect Prompt Injection Multi-turn Jailbreaks Simulated Conversation History Recursive Abstraction Metacognitive Protocol Framework Resolution Contrasting Data Pair mitmproxy & Network Analysis Custom Security Tool Development Python Scripting Agentic Coding Tools

Projects

bypass-prompt-guard-2

An adversarial prefix generator that uses gradient-based optimization to bypass LLM prompt guards like Meta's Llama Guard with a >95% success rate.

Python PyTorch ML
Web2Executable
961 stars

A popular utility with 15,000+ downloads that converts web applications into native desktop executables by deconstructing PE file formats.

Python NW.js Electron
Kaboot

An AI-powered real-time P2P quiz game that uses the Gemini API for dynamic content generation and PeerJS for serverless multiplayer.

React TypeScript Node.js PeerJS Gemini API
Switch Pico Controller Bridge

Custom firmware for the Raspberry Pi Pico that emulates a Switch Pro controller, enabling remote couch co-op and automation via a Python UART bridge.

C++ Python Raspberry Pi Pico
Warp Pipe

A high-performance Linux audio library for virtual node management with per-app routing rules and a Qt6 node-graph editor.

C++20 PipeWire Qt6
halonium
83 stars

A browser automation engine written in Nim.

Nim
einheit
46 stars

A comprehensive unit testing library for the Nim ecosystem.

Nim
nim-libnx
14 stars

An automatic binding generator for Nintendo Switch homebrew that adapts Nim's garbage collector for Switch memory management.

Nim C

Engineering Experience

Current

AI Security Specialist

Trajectory Labs, PBC | Remote

Leading adversarial research and red teaming efforts against frontier AI models.

Nov 2022 – May 2023

Senior Software Engineer

Anaconda Inc | Remote

Migrated a legacy authentication system serving millions of users to Ory. Led team infrastructure and built simulated migration services.

Edmonton

Senior Software Developer

Dotdash

Led Drupal-to-Keycloak auth migration, developed 3 custom Java SSO services. Spearheaded Python 2→3 migration and built ETL tooling.

Nov 2016 – Jul 2019

Software Developer

Go Auto | Edmonton

Managed AWS for 25+ micro-services, optimized Docker builds by 50%, adopted feature flags, merged AWS accounts with zero downtime.

Jun 2015 – Aug 2016

Software Developer

Telephonic Communications

Built real-time phone billing system and call dashboard with Python/Tornado. Slack alerting for high-risk calls.

Nov 2014 – Jun 2015

Python Desktop Developer

AcroOptics LLC

Cross-platform PySide GUI, serial/wireless device communication, Arduino firmware.

2011 – 2014

Earlier Roles

devZing, TrueShip, EMC, Matrikon

Stock analysis algorithms, Django REST APIs, shipping systems, test tooling, .NET web controls.

Skills

Red Teaming

Adversarial Prompting Jailbreaking mitmproxy Network Analysis Agentic Coding Tools Indirect Injection

Languages

Python Nim Java C# JavaScript TypeScript C/C++ Bash

Frameworks

Flask Django React Spring Boot PySide/PyQt Qt6 Node.js

Cloud & Infra

AWS (ECS, EC2, Lambda, S3) Docker PipeWire OpenVPN Linux

Identity & Auth

Ory Keycloak Authentik OIDC OAuth2

Databases

PostgreSQL MySQL MongoDB SQLite MS-SQL RethinkDB

Education

Northern Alberta Institute of Technology (NAIT)
Jan 2025 – Dec 2027 (In Progress)