Hugh Robertson

I sold and onboarded every SwipeBy customer myself. Now I build AI systems and the tests that check them.

Looking for solutions engineer, customer engineer, deployment strategist, go-to-market engineer, and applied AI engineer roles in Chicago or remote.

How I check AI agents

Agents should not be able to grade their own homework.

If an AI agent can chase its own score, the score stops meaning anything. That is Goodhart's law: when a measure becomes a target, it stops being a good measure. Below is how I keep agents apart from the code that scores them, and how I test the product every night. It is part of Shayke, an applied learning project I built with AI coding agents in my own time. It has no customers.

Keeping agents apart from their grader

The agents do the work. A separate program, the scorer, grades it.

Click a move to see what happens when an agent tries it.

  • Import the scorer: stopped by tests.
  • Write a result file: allowed, the only path across.
  • Edit a golden test case: by design, they live in the scorer's own repo.
  • Open a score file: known gap, nothing at runtime stops it yet.
What this stops

An agent shaping its work around the scoring code. Tests fail if an agent's code imports the scorer or names where scores are stored.

A test run every night, the evaluator

The evaluator also scores agent outputs using the scorer's checks. Back to the wall

19 of 19 scenarios passed Latest run, on hard checks, 20 Oct 2026.

What I checked, and what I have not finished

Selling, then building

SwipeBy, Sales Manager and Account Executive

March 2025 to February 2026
  • 12 multi-unit deals and about $60K in annual recurring revenue (ARR) in my first three months, a company record, and a promotion at three months. I moved to Chicago to open the market here.
  • Nobody asked me to, but I built a lead pipeline in Python with the Google Places API and a language model that loaded restaurants and wrote up their pain points, replacing manual CRM entry. AI wrote much of the code; I designed it, directed it and ran it. Code on GitHub.
  • I also built a shared AI assistant that put research on each location in reps' hands before a visit, and grounded it so every claim had to come from its knowledge base. My reps used it without being told to.

Background

  • Seven years as a Senior Constable with Victoria Police: deciding under pressure with incomplete information, then standing behind the decision.
  • A year as Australian Army tank crew.
  • Division I football at the University of Illinois, and a BS in Management from Gies.