Caskey Engineering

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.

Prudential Financial2016 – 2021

Standardized Enterprise Monitoring Across a Fortune 100 Infrastructure

Defined the org-wide monitoring standard and led a zero-disruption platform migration.

ObservabilityPlatform EngineeringSREInfrastructure
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Prudential FinancialMar 2020 – Feb 2021

Sole Owner of Enterprise Reporting During COVID-19 Disruption

Zero reporting outages during the entire COVID-19 remote transition period.

ReliabilityFinancial SystemsLeadershipOperations
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Prudential Financial2013 – 2021

Enterprise MFA Self-Service Platform: Web, Mobile, and QR Code Enrollment

Built three interconnected authentication platforms used by the entire enterprise workforce.

SecurityAuthenticationPlatformMobileEnterprise
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Amazon2022 – Present

Standardized Infrastructure Monitoring Across Thousands of Services

Defined the monitoring standard across thousands of services and drove cross-team adoption.

ObservabilityPlatform EngineeringSREStandardization
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Amazon2024 – Present

Multi-Region Workflow Orchestration Platform

Platform supporting millions of executions across multiple global regions, expanding adoption across Amazon.

Distributed SystemsWorkflow OrchestrationSafetyMulti-Region
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Caskey Coding2024 – Present

Factor-First AI Investment Analysis Narrated by a Six-Persona Committee

Built a Quality + Valuation + Growth + Momentum + Health factor composite narrated by a six-persona committee — one consistent framework across every public equity.

AI/MLFinancial SystemsPlatformFull-StackAWS
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Caskey Coding2025 – Present

AI Marathon Coach Grounded in 90 Days of Actual Training Data

Built a coaching platform that reasons over real Garmin workout history — not generic templates — with a multi-turn AI interface grounded in the athlete's actual load data.

AI/MLHealth TechAPI IntegrationFull-StackAWS
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