Wade Woolwine
Product Security Leader & Distinguished Engineer
Professional Summary
Product Security Leader & Distinguished Engineer with 20 years of experience bridging C-level strategy and code-level implementation. A hands-on practitioner who has founded $60M+ managed services and architected DevSecOps frameworks for 800+ engineers. Expert in operationalizing cutting-edge tech from defining early MDR methodologies at Mandiant to engineering autonomous AI agents today. Passionate about leading high-performance teams, writing code, and solving complex architectural challenges.
Professional Experience
Senior Director of Product Security (Distinguished Engineer) & Deputy CISO
Rapid7
- •Architected the shift from traditional AppSec to DevSecOps for 800+ engineers across 7 product lines
- •Developed AI-powered CVE validation agent using Claude Code and Python
- •Established Security Champions program with 37 engineering leads
- •Served as Deputy CISO for 14 months, briefing Board of Directors
Principal Security Researcher (Threat Intelligence)
Rapid7
- •Developed threat analysis pipeline using Python, PyTorch, and NLP to map behaviors to MITRE ATT&CK
- •Produced the Rapid7 Quarterly Threat Report, supporting marketing campaigns and press interviews
Director & Founder, Managed Detection & Response (MDR)
Rapid7
- •Founded and scaled MDR service to $60M ARR and 250+ customers in three years
- •Designed vCISO service model for SMB executives
- •Led pre-sales, go-to-market strategy, and public evangelism
Senior Manager, Threat Analysis & Hunting
Mandiant
- •Directed team of Principal Analysts delivering advanced threat hunting against nation-state actors
- •Acted as Virtual CISO for 20 enterprise clients
- •Selected speaker for MIRcon on advanced detection methodologies
Senior Threat Analyst (Founding Team, Managed Defense)
Mandiant
- •Founding analyst for Managed Defense, authored technical service delivery methodology
- •Managed 30 simultaneous clients bridging IR and continuous monitoring
Senior Product Security Engineer
Aol
- •Delivered product security services including secure design reviews, SAST, DAST for critical applications
Cyber Threat Analyst
Mantech / Dept. of State
- •Provided cyber threat analysis and intelligence support for Department of State operations
Independent Research & Engineering
Private Cloud Architecture (Proxmox/Talos)
Designed a bare-metal cloud on 4U hardware (4x Tesla V100s) running Kubernetes on Talos Linux with Cilium. Implemented an enterprise-grade GitOps pipeline using Self-Hosted GitLab and Flux CD to automate security scanning (SAST/SCA) for all commits.
AI Agentic Workflows (MCP)
Developed custom Model Context Protocol (MCP) servers to interface Claude Code with local infrastructure (Nginx/SonarQube), enabling natural language autonomous deployment. Engineered an app to fine-tune Small Language Models (SLMs) to map threat reports to MITRE ATT&CK.
Computer Vision
Built a custom home automation integration intercepting Ring video, processing it through a custom-trained image classification model to trigger granular events in Home Assistant.
Technical Skills
Security Architecture & DevSecOps
Cloud Native & Infrastructure
AI & Machine Learning
Executive Leadership
Certifications
AWS Solutions Architect
Amazon Web Services • In Progress
AWS Security Specialty
Amazon Web Services • In Progress
DevSecOps Professional
Practical DevSecOps • In Progress
DevSecOps Expert
Practical DevSecOps • In Progress