Tim O'Brien

Prompt engineering is totally 2025

Fri, 17 Apr 2026 00:00:00 +0000

TL;DR

LLMs are prediction engines that generate responses from the full context they’re given. In older models (GPT-1 through 2025), you could improve performance by using prompting tricks to push them toward usable output (e.g.: personas, examples, “don’t do X”). Frontier models are capable enough that those same tricks can push them too far, activating patterns you don’t want.

Lean, intentionally distilled context now beats elaborate prompts, especially when prompts include extraneous details that may invoke unwanted behavior.

About

Thu, 16 Apr 2026 00:00:00 +0000

I spent fifteen years building customer support organizations at B2B startups — three of them from zero to global, 24x7 operations supporting some of the largest institutions on the planet. I liked the work and I was good at it. Then I left.

Now I’m an owner-operator. I run a specialty coffee roastery with my brother in upstate New York, and I sell hand-forged Japanese tools and teach hand-tool woodworking. Two very different businesses held together by a through-line: making something real, keeping the margin, refusing the race to the bottom.

Annotated Resume

Tue, 23 Jul 2024 00:00:00 +0000

Summary

Highly skilled, accomplished leader with a proven track record of building and scaling global developer-facing enterprise support teams. Adept at overseeing diverse functions, including corporate IT, technical writing, and business and audit support. Highly proficient in developing strategies and processes needed to support API-driven applications, infrastructure, and teams.

Experience

PAXOS ¹

Head of Customer Enablement, 2021-2024

Built technical support engineering and documentation programs, collaborating closely with engineering and customer teams to resolve complex technical issues. Developed organizational strategy, ensured delivery against service level agreements. Interviewed and hired all staff. Created new support offerings and documents as demands of business changed ². Supervised TSEs and Tech Writers.