Riley Brennan, Software Engineer & Tech Lead

Systems that scale. Agents that automate. Teams that ship.

Software engineer, tech lead, and recovering mathematician. For the last few years I've been building LLM-powered tools for financial-crimes investigations at Robinhood, and leading the cross-team projects that get them into production.

1,000+ hrs/mo
Investigator time saved by AI tooling
Greenfield
LLM pipelines, built from scratch
EU + UK
Same-day dual-region launch I drove
10 yrs
Building systems and leading teams
About

The short version

I like solving the problem behind the problem. Lately, that mostly means AI.

I'm a software engineer with a background in math and statistics, and I've always been pulled toward the general solution instead of the one-off fix. For the last few years, that's mostly meant AI.

At Robinhood I build LLM systems for financial-crimes investigations: greenfield pipelines that read, summarise, and classify the way an investigator would, plus the AI tooling my own team uses to move faster. Alongside that, I've led the larger projects: a self-serve detection platform, the same-day EU crypto and UK brokerage launches, and the in-house stack that's replacing our Actimize vendor for filing reports to regulators. Each one was a cross-team effort I designed and drove.

Earlier on, I led inventory systems through a company-wide ERP migration at Google and broke a monolith into services at SPS Commerce. Different problems, same throughline: leave the people around me faster and better-equipped than I found them.

Building

Not just at work

The clearest way to show what I do is to point at something I built solo, end to end, and put in front of real people. This one's live.

● Live · private beta

An AI coach that writes today's session for you

A daily coach that programs around your training, goals, schedule, and history — not a static template. It reads your training in plain English, confirms what it understood, then generates each day on demand and adapts as you log. I designed, built, and shipped the whole thing.

  • Solo, end to endProduct, backend, the LLM programming doctrine, and the frontend.
  • Production-gradeSecure, reliable, and cost-controlled — engineered to run as a real product, not a demo.
  • LLM-nativeEvery session is generated, not looked up — the thing itself, not a demo.
Contact

Let's talk.

Always happy to talk AI, financial-crimes engineering, leading messy cross-team projects, or any problem that's begging for a general solution.