Notion AI
ASHLEY WINTERMUTE
Senior Technical Writer | AI & Cybersecurity Specialist
Phoenix,AZ
Summary
Senior technical writer and cybersecurity analyst with 20 years of experience turning ambiguity into clear, low-friction documentation. Trained under Dan Kaminsky, I learned early how to communicate complex systems with precision, honesty, and just enough humanity to make them actually useful.
Now leading Directive 451, I specialize in AI-assisted documentation, threat intel translation, and knowledge systems that reduce overhead—without sacrificing the signal. I work independently, write clearly, and build content systems people rely on and rarely have to fix.
Overview
20
20
years of professional experience
Work History
Senior Technical Writer & AI Researcher
Freelance
01.2018 - Current
- Authored white papers and technical reports on AI, large language models, and generative AI applications.
- Collaborated with AI researchers, data scientists, and engineers to document AI capabilities, model architectures, and business applications.
- Developed structured content review processes, ensuring clarity and technical accuracy.
- Created diagrams, workflows, and visuals to explain AI-driven systems and intelligent automation.
- Researched AI security risks, including adversarial attacks and bias mitigation strategies, and integrated findings into technical content.
Cybersecurity Consultant & Technical Writer
Remote
01.2010 - 01.2018
- Conducted in-depth security research and authored technical reports on penetration testing, vulnerability assessments, and AI-driven threat detection.
- Developed training materials on ethical hacking, network security, and compliance, supporting both technical and non-technical audiences.
- Created incident reports, risk assessments, and forensic analysis documentation for security teams.
- Researched AI’s role in cyber defense, intelligent threat detection, and security automation.
Chief Operating Officer (COO) | Technical Documentation Lead
Metrix Create Space
01.2010 - 01.2015
- Designed and maintained a comprehensive documentation library covering AI-driven digital fabrication tools (3D printing, laser cutting).
- Developed how-to guides and technical manuals for engineers and makers, simplifying complex workflows.
- Led content strategy for AI-enhanced creative tools, increasing workshop participation by 200%.
- Managed IT infrastructure and security documentation, ensuring compliance with industry best practices.
Cybersecurity Analyst & Technical Writer
White Ops / Dan Kaminsky
01.2005 - 01.2014
- Began as a one-on-one mentee under Dan Kaminsky; the role evolved into a long-term research partnership built on trust, curiosity, and a shared refusal to settle for vague answers
- Supported key projects ranging from DNS and protocol vulnerabilities to adversary tracking and documentation for coordinated disclosures
- Contributed to behind-the-scenes work on the Sony rootkit incident, helping turn technical chaos into something that made sense—clear enough to use, honest enough to trust, and human enough to actually help
- Assisted with early-stage development and research ops for White Ops (now HUMAN Security), back when detection felt more like art than adtech
- Wrote white papers, briefing decks, and technical breakdowns—always with a focus on clarity, without sacrificing the signal
Education
Advanced Coursework In NetSec & Engineering - Chosen For Private Mentorship By Dan Kaminsky
University of Advancing Technology (UAT)
Tempe, AZAssociate Of Arts - English Composition
Yavapai College
Prescott, AZ11.2023
Skills
Content Strategy & Technical Writing
Create documentation that reduces support tickets and improves onboarding
Translate technical workflows into clear, repeatable knowledge
Write for people who don’t want to read—but need to act
AI-Augmented Productivity
Use ChatGPT and Notion AI to accelerate documentation cycles
Build internal tools that generate first drafts and organize chaos
Automate SOPs, knowledge bases, and internal communications
Security-Aware Communication
Translate threat intelligence into accessible, plain language
Craft content that holds up under scrutiny, audits, and time
Communicate risk without leaking detail or overexposing systems
Information Architecture
Design internal knowledge systems people actually use
Structure content to surface answers, not just store them
Simplify complexity without sacrificing the signal
Independent Operator Skills
Self-managed, anti-micromanagement, and outcome-driven
Quick to spot gaps and close them without extra noise
Trusted by engineers, appreciated by leadership
Accomplishments
- Selected for mentorship by Dan Kaminsky, which evolved into a decade-long research partnership
- Contributed to early Sony rootkit investigation and coordinated disclosure strategy
- Founded Directive 451 to translate classified intelligence into public insight—built on the belief that context shouldn’t be a privilege, and clarity shouldn’t require clearance.
- Delivered behind-the-scenes support for major infosec talks, including DEF CON, Black Hat, Toorcon, etc.
Software
ChatGPT (Custom GPTs)
Git
Jira
Confluence
FrameMaker
Markdown
Python (light scripting)
Zapier
Snagit
Bash
Maltego
Google Workspace
Metasploit
AWS
I'm format agnostic If it's logical and has a UI, I'm good
Timeline
Senior Technical Writer & AI Researcher
Freelance
01.2018 - Current
Cybersecurity Consultant & Technical Writer
Remote
01.2010 - 01.2018
Chief Operating Officer (COO) | Technical Documentation Lead
Metrix Create Space
01.2010 - 01.2015
Cybersecurity Analyst & Technical Writer
White Ops / Dan Kaminsky
01.2005 - 01.2014
Advanced Coursework In NetSec & Engineering - Chosen For Private Mentorship By Dan Kaminsky
University of Advancing Technology (UAT)
Associate Of Arts - English Composition
Yavapai College