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Haywood Wells

@haywoodwells

Enterprise CTO driving platform modernization and AI-enabled digital transformation.

United States
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What I'm looking for

I seek senior executive roles where I can lead enterprise technology strategy, drive AI-enabled modernization, and advise leadership on risk, investment, and scaling engineering organizations.

I am an enterprise Chief Technology Officer with 20+ years of experience leading platform strategy, modernization, and AI-enabled transformation across regulated and commercial environments.

I have governed and influenced $20–30M in annual technology portfolios, served as the final technical authority for architecture and security, and designed organizational hiring systems to scale engineering capability.

My work includes translating technical decisions into business outcomes, stabilizing at-risk programs, and positioning firms for growth through disciplined modernization and AI adoption.

I hold an MBA and a BSEE, and I am pursuing an Executive PhD in Management; I partner with executive teams to align technology roadmaps to regulatory requirements, risk posture, and long-term cost curves.

Experience

Work history, roles, and key accomplishments

Education

Degrees, certifications, and relevant coursework

Claremont Graduate University, Peter F. Drucker and Masatoshi Ito Graduate School of Management logoCM

Claremont Graduate University, Peter F. Drucker and Masatoshi Ito Graduate School of Management

Doctor of Philosophy, Management

Enrolled in an Executive Doctor of Philosophy in Management program at Claremont Graduate University’s Drucker School of Management (in progress).

Tech stack

Software and tools used professionally

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Haywood Wells - Chief Technology Officer - Lucky Rabbit LLC | Himalayas