Michael O'Brien.

I spent twenty years teaching sailing. It taught me to settle which lines can't move before trimming anything else, and to let a crew learn by doing the work.

My first job was a six-month co-op through Northeastern at L3 Technologies, as a marketing analyst in strategic marketing. A decade in operations followed. At Uber, from 2014 to 2017, I started investigations as part of one role and built it into a 130-person program across two sites. A support agent built R2D2, an internal Slackbot that answered about 85% of the fraud team's questions from the knowledge base in Slack; I owned that knowledge base and sponsored the bot. I also wrote the logic for automated cancellation refunds. At iAdvize I advised on and helped build the sentiment analysis program for Samsung's live chat during the Galaxy S20 launch, which flagged at-risk customers in real time and alerted senior executives. At Boston Dynamics I led the rebuild of support.bostondynamics.com and built DHL's robot fleet reporting system, working with DHL directly. At Sheprd, a rideshare service for kids, I owned trust and safety and rebuilt onboarding, which tripled new bookings and doubled rebookings.

Lately the work has been whole systems. For an early-stage cybersecurity firm selling to enterprises, I built the system a small team now uses to track renewals for 34 enterprise accounts. Each account shows the contract in force, the signed documents behind it, how the client is billed, and a history of every change that can't be quietly rewritten. On the founding team of a sales platform for real estate, as Founding Director of Operations and Product, I took the product from MVP to live beta.

I also build my own products. SailMOB is a browser sailing game with real wind physics, raced head to head against an AI fleet, and I built it solo (read the case study). It's also how I build with AI agents, because the simulation and the written rules come first and the agents build against them.

I started the company for founders of Seed and Series A software companies in Greater Boston, usually around the time the first enterprise customers sign and before anyone owns the CRM or the data. The work starts with an Ops Audit, which ends in a written fix plan. Then I build what the plan calls for on your own database, and you keep the code and the data.