About Dr. Joe Shepherd
I've never followed the standard path. That's exactly the point.
"The organizations that are winning with AI aren't the ones who hired the most consultants. They're the ones who redesigned how they think."
I started my career in the Air Force — Aerospace Technology, not business school. That non-linear path — from military precision to startup chaos to Microsoft scale to PE advisory — is the reason I see around corners most advisors can't.
I ran a $1.2B business at CDW, led Defense and Intelligence AI programs at Microsoft, built and exited a company, and launched an advisory practice that helped nearly 50 organizations from founder-led companies to enterprise scale. Now I help PE firms and boards apply that operating experience to the hardest problem in enterprise right now: making AI work as a governed business asset, not a technology experiment.
Chief Product Officer — Career Highways
AI-native product strategy, governance architecture, platform investment
Director, Digital Manufacturing & Engineering — Microsoft
AI & secure cloud for U.S. Defense & Intelligence organizations
Founder & CEO — Eczentric (Exit: ZenLeap)
Built and exited a venture-backed talent marketplace; advised ~50 organizations from startup to enterprise
GM, Microsoft Modern Work — CDW
Led $1.2B collaboration practice through successful SaaS-era turnaround
U.S. Air Force — Aerospace Technology
Where precision, accountability, and non-linear thinking became instinct