Christopher Brown | Cybersecurity & Program Management

My Value Proposition

I integrate Cybersecurity, Business Strategy, and AI to drive business outcomes.

Over 15 years, I’ve led modernization initiatives managing $4B+ portfolios—using automation, data analytics, and AI to reduce costs by 25% and deliver faster, more resilient cyber and operational capabilities.

Proven Program Leadership at Scale

Led 620 stand-ups and 320 sprints coordinating 24 experts across 6 cross-functional teams. Delivered projects 15% faster than prior years while managing $23M budgets. Pioneered the first Air Force Special Warfare enterprise, unifying 6,400 personnel and $184M in resources.

Offensive Cyber & Penetration Testing Expertise

Hold OSCP, PNPT, and CPTS certifications with hands-on experience managing penetration testing for 1,000+ Microsoft services. Built and operate PentestAutomator—an AI-enhanced platform that's executed 6K automated penetration tests, significantly reducing security validation timelines.

Cloud Security Architecture & Compliance

Triple-certified across AWS, GCP, and Azure with deep expertise in DoD RMF/ATO standards. Ensured secure deployments of 1,000+ compliant applications at Microsoft while maintaining zero security incidents. Architect and maintain enterprise-grade cybersecurity labs simulating Active Directory, cloud infrastructure, and offensive tooling.

Cost Reduction Through Automation & AI

Generated $4.5M in annual savings through ERP optimization and process automation. Leverage AI-augmented development (Claude Code, Cursor, Copilot) to build security automation tools, enhance penetration testing workflows, and reduce manual operational overhead across enterprise systems.

Executive Stakeholder Management

Managed 26 staff as executive officer to CVP level leadership. Synchronized cyber authorities across 12 Inter-Agency/Intellegence Community stakeholders and aligned product delivery with government mission needs through partnerships with engineering teams and C-suite leadership.

Experience

Microsoft

Technical Program Manager | Aug 2025 - Present

Ensured secure deployments of 1K compliant apps with DoD RMF/ATO standards by coordinating security reviews
Aligned product delivery with government mission needs by partnering with engineering teams and stakeholders to integrate secure-by-design practices.
Reduced time-to-review by 25% - spearheaded teams first ever AI-enabled security automation tool and AI agent
Authored agentic roadmap aligned to CEO priorities of AI-First, PoC developed w/ in 48 hrs, AI agent w/ in 72 hrs

Air Force Special Operations Command - Fort Liberty, NC

Director of Operations | Feb 2023 - Present

Led 620+ stand-ups and 320+ sprints for 6 cross-functional teams, improving delivery velocity by 15% on a $23M budget.
Generated $4.5M in recurring annual savings through ERP modernization and workflow automation across 7 units (750 personnel).
Coordinated cybersecurity operations with 12 interagency/intelligence stakeholders, aligning 32 mission concepts and rewriting 2 enterprise SOPs.
Designed and led a weeklong cyber training program covering AI, Linux, penetration testing, steganography, and malware analysis for 24 experts.
Created and maintained a home-based lab used for secure experimentation in cloud, adversarial simulation, and local LLM integration.

Pentagon

Senior Program Manager - Special Operations & Policy | Nov 2018 - Aug 2021

Co-led the design and implementation of the Air Forces first cyber special operations forces integrating offensive cyber into U.S. defense strategy.
Ensured 100% audit compliance by overseeing 27 cybersecurity policy manuals for 9 global organizations and 5,100+ personnel.
Directed $4B+ in budgetary planning and long-term defense programming across a 5-year FYDP.
Unified 6,400 personnel and $184M under a single Air Force Special Warfare enterprise governance structure.
Served as CEO and CVP level advisor (4 & 1 star Generals), managed $100K budget and mentoring 26 joint staff.

3rd Air Support Operations Group

Assistant Director of Operations | Apr 2017 - Oct 2018

Modernized 36 concurrent programs, reducing overall costs by 45% and improving audit-readiness across 7 orgs.
Managed a $2.7M IT/cybersecurity budget, supporting 1,200 personnel with upgraded secure systems.
Designed and stood up a new 100-person unit, enhancing mission readiness for 850 Airmen.
Implemented standardized governance and compliance reporting aligned with RMF and NIST standards.

Special Tactics Squadron

Operations Manager | Apr 2014 - Mar 2017

Led a $1.5M multinational cyber-readiness exercise involving 22 units, 53 operators, and 19 aircrew, improving joint mission synchronization.
Researched and deployed tactical cyber hardware (drones, IoT, edge computing), enhancing real-time situational awareness.
Deployed Raspberry Pi-based edge computing kits for field missions, improving cyber situational awareness in contested environments.
Maintained a 100% safety record across 45 training events and 8 major exercises.
Recovered $3.2M (21% cost reduction) by auditing and optimizing a $16M supply/equipment program.
Increased Officer manning by 35%, allowed org flexibility for surge deployment by creating/implemening regional recruiting gameplan

Technical Interests & Applied Experience

PentestAutomator: Custom-built AI-enhanced penetration testing tool automating 6K+ scans across web, internal, and cloud apps. Reduces analyst workload and speeds compliance checks at https://pentestautomator.com
Cyber Lab Architect: Architected personal cyber lab replicating enterprise environments using AWS servers, Active Directory, Kali Linux, Docker, Metasploit, Burp Suite, Nessus, and Gemma LLM.
Prompt Engineering + AI DevSecOps: Leveraging Claude, Cursor, GitHub Copilot, and Augment Code to automate threat modeling, recon, and vulnerability chaining.
Azure AI Demo: Built and deployed a live AI inference pipeline on Azure: https://chrisbrownazureaidemo.eastus2.cloudapp.azure.com
Offensive/Defensive Experimentation: Simulate purple team ops in isolated environments; experiment with credential reuse attacks, shadow admin escalation, and AI-enhanced OSINT tools.

Projects

PentestAutomator

AI-enhanced penetration testing platform executing 6K+ automated tests. Built and maintained personally to streamline offensive security operations and enhance threat detection capabilities across enterprise environments.

pentestautomator.com →

Azure AI Demo

Production demonstration of Azure AI capabilities showcasing practical implementations of AI engineering principles, cloud architecture, and machine learning integration on Azure infrastructure.

View Live Demo →

Home Cybersecurity Lab

Enterprise-grade simulation environment featuring Active Directory networks, AWS-hosted servers, offensive tooling (Kali, Metasploit, Burp Suite, Nessus), and local AI models (Gemma). Used for continuous security research, attack/defense scenario testing, and AI-enhanced reconnaissance experimentation.

github.com/csb21jb →

I'm Chris, a Cybersecurity Program Manager, Technical PM, and Penetration Testing Specialist.

My Value Proposition

I integrate Cybersecurity, Business Strategy, and AI to drive business outcomes.

Proven Program Leadership at Scale

Offensive Cyber & Penetration Testing Expertise

Cloud Security Architecture & Compliance

Cost Reduction Through Automation & AI

Executive Stakeholder Management

Skills

Cybersecurity Leadership

Technical Capabilities

Program Management

Experience

Microsoft

Air Force Special Operations Command - Fort Liberty, NC

Pentagon

3rd Air Support Operations Group

Special Tactics Squadron

Technical Interests & Applied Experience

Certifications

Projects

PentestAutomator

Azure AI Demo

Home Cybersecurity Lab

Education

Master of Business Administration, IT Management

Master of Arts, Communication

Bachelor of Arts, Information Technology Systems