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Clifton Gilley
Executive product leader specializing in product management and Agile transformation
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About
Veteran product leader with roughly 20 years of experience spanning legal tech, higher education, and enterprise software, including early AI/ML applications in e-discovery at massive scale. Unusually combines product leadership with a background in law, psychology, and sociology, giving him strong domain empathy and a human-centered approach to UX, AI, and organizational transformation.
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Key Strengths
- 20 years of product leadership across legal, education, and enterprise software
- Led full front-end rebuild after Silverlight EOL while coordinating a microservices upgrade
- Shipped MVP in 3 months and near-full release 3 months later under major platform disruption
- Strong roadmap discipline using Now/Next/Later and team-level top-3 priorities
- Deep cross-functional alignment with engineering, architecture, design, sales, marketing, and services
- Early AI/ML product experience in e-discovery at massive text scale
- Translates complex AI capabilities into defensible, user-friendly workflows for attorneys
- Human-centered UX judgment that improved adoption and usability
- Willingness to challenge poor design decisions using testing and expert input
- Transformed a product org from spreadsheet-driven planning to true Agile execution
- Improved release cadence from 12-16 months to under 3 months
- Skilled at navigating organizational conflict and aligning competing business units
- Strong mentor who developed a services teammate into a product leader and later startup founder
- Domain fluency in law and social sciences that informs product strategy
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Experience
Education
Awards
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Publications
10 publications
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