John Gillespie
Wilmington, North Carolina, United States
Summary
👤
Senior🎓
Top SchoolJohn Gillespie is a seasoned technology executive and CTO with 17+ years of experience building cloud-first, data-driven systems across logistics, healthcare, and banking. Currently leading engineering and AI strategy at FreightVana, he has a proven track record scaling operations (helping MegaCorp Logistics grow from $350M to $1B while keeping IT spend under 2%) and reducing unit costs through automation and forecasting. He combines deep enterprise architecture and governance experience—implementing Azure-first platforms, identity automation, and regulatory-aligned security—with hands-on delivery of TMS, ERP, and analytics modernizations. As founder of Outer Kai Technologies he advises boards and CEOs on AI readiness and right-sized operating models, blending fractional CTO pragmatism with executive accountability. Based in Wilmington, NC, he’s equally comfortable in the data plane and the boardroom, and treats software as a sandbox for exploring ideas that drive measurable business outcomes.
10 years of coding experience
5 years of employment as a software developer
Political Science and Government, Political Science and Government at University of North Carolina WilmingtonPublic Health, Public Health at University of North Carolina at Charlotte
Github Skills (18)
git10
javascript10
github10
patch10
css10
math10
subversion10
nodejs10
react10
codebase9
certification9
html5-canvas7
chrome6
canvas4
github-pages4
Programming languages (4)
Github contributions (5)
olddognewtrix123/Precursor
May 2017 - Jun 2018
Contributions:3 pushes, 1 branch in 1 year
olddognewtrix123/kyle
May 2018 - Jun 2018
Contributions:6 commits, 3 pushes, 1 branch in 1 month
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