Work
Case Studies
Detailed accounts of enterprise platform leadership and personal AI product builds: the problems, decisions, and outcomes from systems I designed and owned end to end.
7 case studies
Prudential Financial2016 – 2021Standardized Enterprise Monitoring Across a Fortune 100 Infrastructure
Defined the org-wide monitoring standard and led a zero-disruption platform migration.
Read Case Study →Prudential FinancialMar 2020 – Feb 2021Sole Owner of Enterprise Reporting During COVID-19 Disruption
Kept enterprise reporting uninterrupted throughout the COVID-19 remote transition.
Read Case Study →Prudential Financial2013 – 2021Enterprise MFA Self-Service Platform: Web, Mobile, and QR Code Enrollment
Built three interconnected authentication platforms used by the entire enterprise workforce.
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Amazon2022 – PresentStandardized Infrastructure Monitoring Across Service Teams
Defined a shared monitoring standard and drove cross-team adoption.
Read Case Study →Amazon2024 – PresentMulti-Region Workflow Orchestration Platform
A multi-region platform that puts every workflow execution behind concurrent safety checks, with adoption expanding across Amazon.
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Caskey Engineering2024 – PresentFactor-First AI Investment Platform Narrated by a Six-Persona Committee
Grew a single-ticker grader into a full investment platform: a four-factor composite (Quality, Valuation, Momentum, Health) narrated by a six-persona committee, a nightly scan of 600+ large caps, portfolio and net-worth tracking, and daily measurement of historical ranking behavior.
Read Case Study →Caskey Engineering2025 – PresentAI Marathon Coach Grounded in 90 Days of Actual Training Data
Built a coaching platform that reasons over real Garmin training and recovery history, not generic templates, pairing a deterministic safety-first rules engine with a multi-turn AI coach and a Whoop/Oura-style data dashboard.
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