Riley Trottier
Riley Trottier
Senior Product Manager - building with artificial intelligence

I'm a Senior Product Manager at Workday, building an agent for contract management and automated accounting. Outside work I build and ship my own AI apps, including two live web apps, an MCP server and a public library of Claude skills, and I write here about building them. Before Workday I worked on payments, public transit and health tech products.

LATEST DISPATCH · PRODUCT

Building a PM Operating System

Six layers in one repo, from a rules file to scheduled jobs, that hold my AI setup at work together and make it easier to fix.

RECENT DISPATCHES

PRODUCT

Fixing AI Automations That Failed Quietly

Three scheduled AI jobs that never worked, and the changes to where they run, what they cost and how they get checked.

Oct 2026 · 4 min read
PRODUCT

Guardrails for an AI Assistant

Five rules that keep an AI assistant from doing something slightly wrong under my name, and how each one is enforced.

Oct 2026 · 3 min read
PRODUCT

Building an AI Skills Library

Turning repeated AI instructions into versioned skill files, split across git repos, so a fix made once carries over to every task after it.

Oct 2026 · 3 min read
PRODUCT

Probabilistic Planner, Deterministic Executor

A design for AI features where every number has to be explainable. The model proposes, and plain code checks and carries it out.

Oct 2026 · 3 min read
BUILDING

Why I Shut Down Throughline

A personal dashboard built with Claude in September 2026, what went wrong with it, and why it was turned off after a few weeks.

Sep 2026 · 5 min read
BUILDING

Building ReflectAI, an AI Journaling App

A daily journal where Claude writes monthly and yearly reports. The AI reports took one rewrite of the instructions; privacy, sign-in and testing took much longer.

Sep 2026 · 4 min read
BUILDING

Building OnePage, My First App

A one-screen task manager with AI monthly reports, built on Replit in May 2025 and later moved to Railway.

Sep 2026 · 3 min read

About

I've spent about eight years in product management, across payments, health tech, public transit and now enterprise finance software. I'm based in Victoria, BC, where I'm learning French and playing a lot of chess. Proud new father as of 2026.

I'm always glad to talk about product management and building with AI. More about me or send me an email.