Seasoned LEaders.

With Expertise From Government & Tech Sectors.

Our Fellows are dedicated to safeguarding tomorrow, today. Leaders in their own sectors, they bring their inquisitive minds to our innovation laboratory, developing an ever-vigilant defense against data exploitation.

Kristopher Schroeder


Kris started toying around with computers in the late 80’s which fueled two degrees in Computer Science and a career driving market and technology strategy for leading commercial and federal customers. While working on the front line of Cyber Counter-Intelligence and open source information exploitation, he realized that there needed to be a fundamental change in how people and organizations interact and live online. He and Ryan founded Grey Market Labs to empower this change.

Prior to Grey Market Labs, Kris was a Principal and Officer in Charge for Booz Allen Hamilton leading a $40m annual systems delivery business. He helped establish the National Open Source Enterprise, created the first federal open data pandemic collection and analysis system, and horizon scanning systems for Fortune 500’s. Former Adjunct Professor with Johns Hopkins University. With his wife, he founded Uncorked, Inc a 501(c)3 supporting the DC community.

Ryan Underwood


Ryan began his software development career in the early 1990’s with BBSs, IRC, and eventually the modern internet. His interests center around internet-based surveillance, tracking and detection techniques.

His formal education includes a bachelor’s and master’s in Computer Science with a concentration in Artificial Intelligence. For the past 20 years, as a software architect and developer he has worked on projects across the internet spectrum including lawful intercept and telecommunications surveillance programs, internet research training and internet attribution research and development.

Most recently, as a Chief Engineer at Booz Allen Hamilton, he led programs focused on Data Science, Malicious Cyber Behavior and Cyber-Counterintelligence.

Engineering & Operations

Our engineering and operations team is made up of experts from Silicon Valley to Washington DC, with a unique perspective on bringing products to life and creating a captivating user experience:
• Engineering leaders in commercial Cloud Deployments, Platform-as-a-Service, Containerization, and Artificial Intelligence
• Operations and support to Federal, Fortune 500 and International Customers
• Active participants in the open source projects related to Grey Market Labs

Christopher Caine


Chris is President & CEO of Mercator XXI, LLC (, a professional services firm helping clients engage the global economy. He is also President of the Center for Global Enterprise (, a New York based non-profit organization dedicated to the study of the contemporary corporation in the era of global economic integration. Prior to Mercator XXI and CGE, Chris spent 25 years at IBM and for thirteen years he had corporate responsibility for global public policy issues that impacted IBM in his role as Vice President, Governmental Programs.

Chris is an expert in policy and economic development trends involving government, innovation, globalization, global electronic commerce, privacy, and new security challenges. Chris brings this perspective and his long history with corporations and their executives to help Grey Market Labs address the challenge of Privacy Exploitation in the conflicting age of GDPR and Facebook.

Gary Cubbage


Gary brings more than 31 years of experience developing and deploying mission and enterprise systems for federal and commercial clients. Gary recently retired as an Executive Vice President at Booz Allen Hamilton as a leader in the Digital Solutions business, with a particular emphasis on developing and operationally fielding solutions for some of the more challenging analytical and operational issues facing national security. Through these experiences he developed a deep understanding of the need for digital privacy and understanding of the associated technical and policy issues that also must be solved to address this need.

Gary lives in Leesburg and works on sharing needed, but not necessarily appreciated, guidance to his college and high school-aged daughters. He also serves as Vice Chairman for the Northern Virginia Therapeutic Riding Program (NVTRP), providing services to children with disabilities as well as returning military service personnel.

Tim Estes


Tim is the President and Founder of Digital Reasoning. Tim envisioned a new way computers could learn to understand language and made that vision a reality. He is a leading influencer, advocate and speaker for the use of technology and analytics to achieve social good in industry, government, healthcare and academia. He also cares a ton about protecting digital privacy and would have taught philosophy in another life. Tim lives in Nashville when not hopping all over the world to try to make a difference. He counts among his friends some of the most talented musicians, wellness innovators, and passionate foodies in Nashville.

Tim has been a friend of Grey Market Labs and our public benefit mission from the beginning and brings his long history with software products and success in financial services to help with some of our most pressing initiatives.