Todd S.

Key Skills

Software

Internal/Proprietary Tooling

Top Subject Matter

Network Engineering & Systems Architecture

Regulatory Compliance & Risk Analysis

Cybersecurity & Data Protection

Top Data Types

Text

Document

Computer Code Programming

Top Task Types

Red Teaming

RLHF

Computer Programming/Coding

Evaluation/Rating

Function Calling

Question Answering

Text Summarization

Prompt + Response Writing (SFT)

Freelancer Overview

While I am launching my career in AI data training, I bring over two decades of elite, hands-on domain expertise as a CISSP, CCIE Emeritus, and security and infrastructure leader. My extensive background managing hyperscale operations, full-stack network architecture, and complex UNIX/Linux environments means I inherently possess the deep technical knowledge required to ground-truth, evaluate, and optimize highly sophisticated LLM outputs with absolute precision. What sets me apart is my extensive background in cybersecurity and regulatory compliance. I am uniquely positioned to excel in adversarial prompt engineering and safety red-teaming. Because I have spent my career securing critical data environments, I can immediately apply those skills to stress-testing model guardrails, identifying logic flaws, and crafting rigorous edge-case prompts to ensure AI outputs are both technically accurate and securely aligned.

Labeling Experience

Director of Information Security

Segmentation

Served as the cybersecurity leader reporting directly to the Chief Engineer and partnering with executive leadership. Oversaw information security strategy, compliance, and infrastructure protection for highly regulated operations. Led enterprise cybersecurity strategy and ensured compliance with government and regulatory frameworks. • Developed and executed enterprise-wide cybersecurity strategies aligned to ITAR, CMMC, FedRAMP, and NIST 800-53 • Protected CUI and export-controlled data via access controls, IAM, encryption, and secure segmentation • Directed risk management and incident response planning aligned with federal cybersecurity mandates • Implemented secure cloud and on-premises infrastructure to meet FedRAMP High and CMMC Level 2+ requirements

2019 - 2023

Education

Work History