Bob Gourley

Bob Gourley is co-founder and CTO of OODA LLC, a cybersecurity and artificial intelligence consultancy. Gourley is publisher of CTOvision and OODAloop, and the author of the bestselling book The Cyber Threat. Named as one of InfoWorld’s top 25 CTO for 2007, Gourley has served as the CTO for the U.S. Defense Intelligence Agency.

This article is by Featured Blogger Bob Gourley from his CTOvision column. Republished with the author’s permission.  

In technology due diligence, there really is no substitute for experience. 

I’ve spent a career evaluating the business impact of technology and building strategies that optimize the contribution technology makes to enterprise missions. 

In my first career as a naval intelligence officer I was frequently called upon to find ways to leverage technology to enable our missions of all source intelligence analysis. Other times I was required to assess how adversaries were using technologies as they sought to gain advantage in their own decision-making. Later as an executive with TRW and then Northrop Grumman I helped shape internal investments that sought to create technology in support of critical government missions. Back in government as the Chief Technology Officer (CTO) of the Defense Intelligence Agency (DIA) I was part of a team that sought to leverage the very best technology in the free world to support agency missions of analysis, production and collaboration. 

For the past decade I have continued to evaluate technology, including participating in numerous formal due diligence assessments. I have conducted due diligence assessments in support of private equity firms, venture capital firms, large companies seeking understanding before before purchasing other firms in M&A, and for other companies that wanted to assess their own capabilities so they could optimize their own value for a future transaction. 

I have captured lessons from my experience in technology due diligence in a short presentation on the OODA YouTube Channel this link

These lessons are provided in a way that should be of use to organizations on both the buy-side and sell-side of potential transactions, and concludes with actionable recommendations including expectations you should have when selecting a due diligence partner. 

Our hope in producing this short overview of lessons learned from technology due diligence is that you will keep OODA in mind for your future needs. In tech due diligence, experience matters, and we have that. 

For more technology due diligence related resources see: 

Technology Due Diligence Sensemaking: Due Diligence prior to an investment, merger, acquisition or other business event is best done with experienced professionals who have past performance. This is especially true when assessing the technology or cybersecurity of a target firm. Due Diligence professionals should also maintain a current understanding of the state of enterprise 

A CTOs Perspectives of Technology Debt in Mergers and Acquisition: One of the critical factors which needs to be evaluated in any technical due diligence is the concept of Technology Debt. This report provides insights into technology debt from the perspective of an enterprise CTO turned due diligence professional. These lessons can help companies preparing for a future transaction to better position themselves for optimal outcomes. These lessons can also assist private equity and other investors in thinking through aspects of technology risk and identify areas requiring additional focus prior to a transaction.