Rockie Brockway

Practice Lead, Office of the CSO


Experienced 25-year veteran of IT/IS and highly technical Information Security Analyst, Design Architect/Assessor specializing in Business Systems/Impact Analysis. Through an understanding of business needs in relation to protecting business critical data (Brand Protection), he assists organizations in achieving their desired business outcomes. He has consulted in nearly every vertical and marries a strong technical background with outstanding creativity, communication skills, leadership, team building/teamwork skills and business acumen.

Technology Background and Skillsets
• Enterprise Security Architecture
• Red/Purple Team Penetration Testing (PTES utilized)
• Adversary Emulation
• Threat/Vulnerability/Identity Management
• Monitoring and Incident Response
• Threat Intelligence
• Threat Modeling
• Data Classification Business Background and Skillsets
• Business Owner/President/CTO
• Business Systems Analysis
• Adversary Analysis
• Business Impact Analysis (FAIR utilized)
• 3rd party Risk Management
• Advanced Business/Security Metrics Development
• Outcome Oriented Strategic Business Initiatives

Education & Certifications

Case Western Reserve University, BA, Computer Science Currently none of the 30+ certifications achieved in the past 25- year career, including GSEC, GCIH and GSNA, are active. Actively working towards OSCP and EMBA.

Professional Affiliations

President, Secure Cleveland; Governing Board Cleveland CISO Executive Summit; BSides Cleveland Conference Organizer;  Infragard member (since 1998); SANS GIAC GSEC Mentor (taught three times); Cisco Partner Technology Advisory Board, Security

Industry Contributions

Security Conference Speaker at DerbyCon, GRRCon, CircleCityCon, RVASec, CONVerge Detroit, ShowMeCon,  Information Security Summit, BSides Boston/Rochester/Cleveland/Detroit, Ohio ETech

Passion for Security

Even before my first computer at the age of 12 (Apple II+) I have been fascinated and drawn towards figuring out how things work and if they can be made to do “other” things. Early exposure to a computer quickly led to changing settings on games with sector editors and programming rudimentary programs in BASIC. These gateway drugs led me to Case Western Reserve University to study Computer Science, where I was lucky enough to be introduced to Dr. Peter Tippett and interned at his company Certus International in 1992. Certus was one of the first Anti-Virus companies (later sold to Norton) and once I was exposed to the underground BBS world of computer virus sharing, reverse engineering and creating malicious Assembly code there was no turning back. My Network, Systems and Scripting basics were honed in the 90’s where I was the first employee of one of Ohio’s first ISPs. In 2000, I started my own security services focused company where I honed the higher-level skills of penetration testing, incident response, and forensics as well as jumping into the fire of owning and running a business. After we sold that company in 2007 I continued to hone those technical skills, but my attention started leaning towards the business side of infosec. Why is security so hard? Why does the business look at security as an obstacle rather than an enabler? How does this relate to basic human nature? Risk became an obsession and I started realizing the ties to group theory, natural systems, and adaptation. The past decade I have been working these theories out (with others) and applying them in real-world enterprises as a strategic and tactical advisor. This stuff is fascinating and I believe weaving these theories in with a solid Enterprise Security Architecture model provides the most value to our clients and sets us apart from other consultants who are not looking at the larger client business outcomes. Don’t get me wrong – I still love a good DNS TXT C2 Beacon and the rush of breaching a physical target. Just don’t ask me what 8086 DOS Int 21 does these days unless I can Google it.

Recent Blog Posts

The Backup Paradigm Shift: Moving Toward Attack Response Systems

Black Hawk Down I’m guessing a lot of us in the IT and Security space have experienced the gut wrenching feeling of not receiving that ICMP ping reply you were expecting from a production system, be it a firewall, switch, or server. Was there a recent configuration change that happened prior to the last reboot?...

Using Effectiveness Assessments to Identify Quick Wins

An organization’s overall security posture can be viewed from multiple different angles, such as technical assessments, program assessments, controls assessments, and risk assessments. A number of different frameworks for each of these assessment types exist, intended to help both technical teams as well as leadership organize security program building activities. Some of these include: Penetration...

Crossover Sec: Breaking Down the Silos

People who know me well, or who saw the Derbycon 6 talk I gave with Adam Hogan, “Adaptation of the Security Sub-Culture,” know of my non-InfoSec hobby and history of playing in loud bands that recorded and toured across the U.S. and Canada, mostly in the 90s. It was music in the 80s that had...
View all posts from Rockie

Recent Webinars

MITRE ATT&CK™ Solutions Update and Evolution: Exploring Advanced Applications of ATT&CK

The MITRE Adversarial Tactics, Techniques, and Common Knowledge (ATT&CKTM) Framework ( is advancing as the go-to model for understanding known cyber adversary behavior. How TrustedSec Helps Organizations With ATT&CK Today, TrustedSec uses the ATT&CK framework to help organizations prioritize security...

Resilience in the Middle of the Storm—Preparing Security Teams for Disaster

This webinar was recorded on 3/19/20. As populations are affected by disaster, what can you and your organization do now to mitigate security risk? Preparing for the worst For those who aren’t fully prepared, what are the major areas that...

Using MITRE ATT&CK(TM) for Coverage and Effectiveness Assessments

Recorded on February 13th, 2019, AT 1:00 PM EST What is the MITRE ATT&CK(TM) Framework? The MITRE Adversarial Tactics, Techniques, and Common Knowledge (ATT&CKTM) Framework ( is “a globally-accessible knowledge base of adversary tactics and techniques” that is “open and available...
View all webinars from Rockie

Recent Podcasts

Rockie Brockway

Want to work with Rockie Brockway or someone like him?

The TrustedSec team is comprised of experienced and qualified security professionals. Contact us to learn more about our services, our team, and how we can help you.
Contact Us