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 on the App Store · invite-only

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.
Small & free

Mac menu-bar apps

Two small tools I built for myself and decided to share. Free, open source, signed & notarized.

Clicker app icon
Apple TV remote

Clicker

An Apple TV remote that lives in the menu bar. Siri Remote layout, scroll to navigate, type searches from your Mac keyboard, launch apps, and see what's playing — no phone required.

Pingky app icon
Latency heatmap

Pingky

A cheerful widget that pings once a second and paints a rolling latency heatmap — green when it's fast, red when it's slow, black when it drops. For the engineer waiting on airplane Wi-Fi to come back.

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.