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Jacob Wheatley

@jacobwheatley

Cybersecurity AI Fellow at Handshake AI who evaluated prototype models and placed top 10 in the DoD Cyber Sentinel Challenge.

United States

Message

At Handshake AI, I evaluated prototype AI models for cybersecurity knowledge accuracy, identified weaknesses in LLM responses, and documented my findings. I also assessed AI systems for security vulnerabilities and delivered targeted recommendations.

I worked directly with organizations to support AI security implementation and threat response guidance.

For the 2025 Department of Defense Cyber Sentinel Challenge, I competed in OSINT and cybersecurity CTF challenges, placing in the top 10 out of over 2,000 competitors.

I designed and built Reconsuite, a cybersecurity toolsuite with network reconnaissance, vulnerability scanning, and OSINT capabilities. I’m pursuing CompTIA Security+.

Experience

Work history, roles, and key accomplishments

Cybersecurity AI Fellow

Handshake AI

Apr 2026 - Jul 2026 (3 months)

Evaluated prototype AI models for cybersecurity knowledge accuracy, identifying weaknesses in LLM responses and documenting findings. Assessed AI systems for security vulnerabilities and delivered targeted recommendations to improve cybersecurity posture.

AI Security LLM Evaluation Vulnerability Assessment Threat Response Technical Documentation

Education

Degrees, certifications, and relevant coursework

CompTIA

CompTIA Security+, Cybersecurity

Pursuing CompTIA Security+ certification, currently in progress.

Oregon Institute of Technology

Bachelor of Cybersecurity, Cybersecurity

Bachelor of Cybersecurity with relevant coursework in network security, incident response, and cloud infrastructure. Multi-semester President's List recipient.