Seasoned LEaders.

With Expertise From Commercial & Government Tech Sectors.

Our team members 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.

Nicholas Donofrio


Nicholas Donofrio (NAE) is a 44-year IBM veteran who held the coveted position of Executive Vice President Innovation and Technology and was also selected as an IBM Fellow, the company’s highest technical honor. He is a Life Fellow of the Institute for Electrical and Electronics Engineers, a Fellow of the U.K.-based Royal Academy of Engineering, a member of the U.S.-based National Academy of Engineering (NAE), a Fellow of the American Academy of Arts and Sciences, a member of the CT Academy of Science and Engineering, the New York Academy of Science, Sigma Xi, Tau Beta Pi, Eta Kappa Nu and the Society of Women Engineers.

He is also a member of the Boards of Security Scorecard, Sproxil, Quantexa, HYPR, TCIG.TECH, Ravenpod, the New York Genome Center, the National Association of Corporate Directors, and the Peace Tech Lab. He served on the Boards of APTIV, AMD, Liberty Mutual, BNY Mellon, O’Brien & Geere, the New York Hall of Science, NACME, INROADS, the CT Board of Regents for Higher Education, RPI, Clarkson University, and Syracuse University. He is a Presidential Fellow at NYU Tandon School of Engineering and a Lecturer at the Columbia University School of Professional Studies.

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.

Todd Helfrich


Todd helps tech leaders understand the public sector and increase their probability of success across commercial and government technology product sales. Helping people solve challenging problems through innovative solutions is something he enjoys greatly. With over 20 years of experience in cybersecurity, customers past and present rely on Todd as a strategic advisor. He has has helped multiple businesses reach growth targets and had four successful exits due to the business being acquired by major tech players, including Attivo Networks to Sentinel One, 2022.
As a business advisor and investor in the technology sector, he works closely with members of the venture capital community, including Dell Technology Ventures, Forgepoint Capital, Google Ventures, Gula Tech Ventures, Grey Croft, Intel Capital, In-Q-Tel, IVP, and Paladin Capital Group.
Todd serves as ambassador to Cyversity, a nonprofit focused on Diversity, Equality and Inclusion (DEI) and, beyond work life, he is a father and a husband — his family is the “why” behind his success.