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William J. Littlefield II

William J. Littlefield II

Technology entrepreneur, principal engineer, and philosopher of technology and ethics

Tbilisi, Georgia
Joined June 2025

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1.9K connections
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Summary

William Littlefield is a serial entrepreneur and co-founder in the AI and fintech space, with a proven track record of leading startups from inception to acquisition. He co-founded AIrecruit, which was strategically acquired, and is currently involved in leadership roles at Unlimited, Silicon Valley Support, and as a board observer at Zero Hiring, demonstrating a continuous drive for innovation and business development. layoftheland+1
With an extensive background as a principal engineer at companies like Visa and Wizest, William possesses deep technical expertise in software architecture, full-stack development, and complex API integrations. His roles have involved integrating consumer authentication into eCommerce technologies and leading globally distributed engineering teams. scrumalliance+1
Beyond his technical and entrepreneurial ventures, William is an academic researcher in digital ethics and the philosophy of technology. He holds advanced degrees in World Literature & Philosophy and has conducted research on AI's impact on climate justice, geopolitics, and computational creativity, often exploring the reconciliation of modern technology with classical philosophical concepts. williamjlittlefield+3
William demonstrated an early entrepreneurial spirit and leadership during his time at Case Western Reserve University, winning business plan competitions with innovative projects such as a thermochromic sticker and an action-adventure video game. He credits his figure skating background with fostering discipline and a willingness to take unconventional paths, which proved beneficial in his startup career. case+1

Work

Education

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Hobbies

William is an accomplished figure skater, having trained for over a decade with Olympic coaches and athletes, competing at the U.S. Figure Skating Championships. case+2

Notes

AJAlex Jakubowskisaid
WLWilliam Littlefield
is someone they consider a true leader and domain expert in their field.

Dec 14, 2025

AJAlex Jakubowskisaid
WLWilliam Littlefield
is one of the most effective C-suite leaders they've seen at a large enterprise.

Dec 9, 2025

SBShahriar Broumandsaid
WLWilliam Littlefield
has impressed them with their ability to build and execute a go-to-market strategy for enterprise or government clients.

Oct 29, 2025

SDScott Downessaid they've seen
WLWilliam Littlefield
bring meaningful AI or machine learning expertise to platform engineering projects.

Oct 9, 2025

JSJuwariah Shareefsaid
WLWilliam Littlefield
is one of the most effective full-stack engineers they've worked with.

Oct 6, 2025

RHRush Hogansaid they would trust
WLWilliam Littlefield
to lead a critical project involving building or scaling APIs and SDKs.

Sep 29, 2025