
Overview
Terra Security is an AI-driven cybersecurity startup. As part of a part-time product and data role, I built an internal system to understand how its AI pentesting agents were being used and where they fell short, using the agents' conversation traces as the source of truth.
What I built
- Pre-scoring. Sentence-BERT embeddings to pre-score conversations.
- Structured extraction. Claude, via the tool-use API, extracts structured fields from each trace.
- Four analytics engines. Intent distribution, satisfaction, a CORE / NOISY / NICHE / REMOVE skill quadrant, and a skill-gap recommender.
- Calibration. An LLM-as-judge step calibrated against human ratings.
Design choices
Sentence-BERT pre-scoring runs before the Claude extraction step, and the LLM judge is checked against human ratings before its scores are used.
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