Founder & CEO

TrailGuide AI is led by Mike Cauldwell, a technology leader dedicated to bringing enterprise-grade AI strategy to growing businesses.

Mike has spent his career mastering complex systems so business owners don't have to. His background includes optimizing business systems at Booz Allen Hamilton and managing major programs at Amazon Web Services, where he trained internal teams on AI implementation. This technical rigor is grounded in his service as an Army Infantry and Special Operations officer and his academic pursuits that include an MBA from NYU and a Master’s in Information Technology from Virginia Tech.

Mike founded TrailGuide to cut through the hype. He provides SMBs with a disciplined, practical approach to AI focused on clarity, transparency, and execution.