Backgroundnew jerseysince 2011
About
I came into tech in 2011 through Workforce Opportunity Services, placed at Prudential Financial while I was still serving in the NJ Army National Guard, and taught myself to code on the job. By 2013 I was the Remote Access Analyst: Tier 3 help desk work with a side project generating QR codes for MFA enrollment. That side project ran for eight years and produced over 300,000 activation codes. It also settled which job I wanted: the engineering one, not the support one.
From there I moved up through Remote Access SRE and Senior Remote Access SRE at Prudential, where I built the MFA self-service portal used more than 18,000 times in six languages, automated over 200,000 administrative actions, and kept the VPN running for 60,000 corporate users through the early months of COVID. Most of that work was figuring out how to make safety-critical infrastructure quiet: how to remove failure modes rather than paper over them.
In June 2022 I joined Amazon, where I built a monitoring lifecycle platform that onboarded more than 2,750 application stages and brought 3 million monitors under standardized management, and hired and mentored eight new-to-industry engineers in New York. In August 2024 I moved into my current role as a Senior Software Engineer on a platform team, architecting a twelve-service workflow orchestration platform whose safety framework has run roughly 500,000 checks across Amazon's fleet, validating every change before it lands. The lesson carried over from Prudential intact: the platforms worth building are the ones that stay quiet while everything they watch does not.
Nights and weekends I test the same convictions where nobody is grading me: an open-source RAG system engineered to refuse when it should, a C++ options engine tuned to 215 million prices a second, and AI finance tools where the model narrates numbers it is never allowed to derive. The selected builds are on the work page; the full writeups live on Caskey Engineering.
Along the way I ran a New Jersey WordPress shop called Caskey Coding from 2015 to 2018 (ten sites for small businesses and community organizations), and served six years as a Military Police Officer in the 50th Brigade of the NJ Army National Guard, including a 2012 Superstorm Sandy activation where I safeguarded the distribution of 241,000 gallons of FEMA fuel for nearly a month.
Values
Guardrails, not booleans.
Safety systems that explain themselves are what keep velocity sustainable past the first incident. Every guardrail I build has to say not just what failed, but why, what would make it pass, and who owns remediation.
Structure before code.
Design before you dive in. Implementation is the fast half; the specs, folder structure, and decision logs that precede it decide whether the system holds up. The structure does not follow the AI; the AI follows the structure.
Scale is the evidence.
A title tells you where someone sits, not what they own. I state mine for context, then let the systems, and the numbers behind them, carry the argument.
Earned lessons only.
I write what I have learned by getting it wrong first, in production. The decisions I would make differently are the ones worth writing about.
Build the systems other engineers depend on. Write honestly about how it goes.
On writing
I publish long-form essays on workflow orchestration, safety-critical platforms, and spec-driven development at Caskey Engineering (caskeycoding.com). It is the engineering side of this website, a working notebook where the arguments get worked out in full.
