Experience5 roles2009 → presentupdated

Work

Eric Caskey has held five roles since 2009, fifteen of those years in technology, from the NJ Army National Guard to Senior Software Engineer at Amazon today. He joined Amazon in June 2022 and has held the Senior Software Engineer title since August 2024. The deep case studies, with the metrics and the architectural decisions, live on Caskey Engineering.

AmazonSoftware Engineer → Senior Software Engineer
Jun 2022 – Present
  • 500,000 safety checks
  • 3 million monitors

Architected a workflow orchestration platform built safe by default: validation guardrails run before every automated change, and a spec-as-code system gives AI coding agents curated context instead of raw access. Its guardrails have run 500,000 safety checks. I also own the monitoring platform underneath it, which keeps 3 million monitors standardized across 2,750+ application stages.

Case study on Caskey Engineering →
(opens Caskey Engineering)
Prudential FinancialRemote Access Analyst → Senior Remote Access SRE → Cloud Engineer, SRE
Apr 2013 – Jun 2022
  • 200,000+ administrative actions
  • 60,000 corporate users

Built the MFA self-service portal used over 18,000 times in six languages, automated 200,000+ administrative actions, and kept the VPN running for 60,000 corporate users through the early months of COVID.

Case study on Caskey Engineering →
(opens Caskey Engineering)
Workforce Opportunity ServicesConsultant
2011 – 2013

Launched my technology career as a WOS consultant, rapidly learning enterprise IT environments and contributing to Prudential's remote access platform operations.

Caskey Coding, LLCOwner, operator
Feb 2015 – May 2018
  • ten sites
  • clicks from 2 to 52

Ran a New Jersey WordPress shop. Delivered ten sites for small businesses and community organizations. SEO work for The Drain Guys took monthly organic clicks from 2 to 52 in six months.

NJ Army National GuardMilitary Police Officer, 50th Brigade Special Troops Battalion
Jul 2009 – Jun 2015
  • 241,000 gallons of FEMA fuel

Reached senior Specialist rank. Activated for 2012 Superstorm Sandy recovery, assigned to safeguard and distribute 241,000 gallons of FEMA fuel for nearly a month.

Projects

Selected builds

A selection of what I build on my own time, on the same stack I use at work. Most link to the live tool, the writeup, or the playground on Caskey Engineering. The finance work is engineering, not investment advice.

MethodSpec-driven engineering platform →One engineer, a fleet of AI coding agents, a work queue, and an attested merge gate, written up as a case study and taught as a lesson series.ToolMarathon Coach →Grounded AI marathon training plans with Garmin integration.ToolFinance Reviewer →Deterministic factor scores narrated through six investor perspectives.Open sourceBallast →An open-source RAG system with a guardrails gateway, engineered to refuse when it should.ProjectSpecSelf →An operating system for a life, run like a spec-driven codebase, with AI agents that read but never write.EngineC++ pricing engine →A Black-Scholes options engine tuned from 15 to 215 million prices a second on AVX2 SIMD.PlaygroundMarket visualizations →Real-data 3D views of market structure, volatility surfaces, and factor behavior.PlatformFinance research platform →The decision engine, backtester, and methodology behind the Reviewer, documented in the open.

Everything above, and several things that are not, lives in full on Caskey Engineering.