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Working at Courtyard AI
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About
Courtyard's argument is that search is moving inside AI assistants, and that small and medium-sized businesses are the ones most likely to be left out of that shift. Its product pulls a business's own knowledge — availability and scheduling from the software it already runs, PDFs like menus and price lists, images, and research about the business from the open web — into a single structured record that agents can read, exposed over the business's own MCP endpoint. The company describes the outcome plainly on its site: "The more AI knows your business, the more customers it sends." Kirk Simpson, who co-founded Wave and sold it to H&R Block, told the TechTO stage in June 2026 that Courtyard came out of GoConfirm, the earlier consumer venture he could not make work, and that the idea belongs to Sam Pajot-Phipps, Courtyard's chief executive: "Courtyard is really aimed at helping small to medium-sized businesses find new customers through AI." Simpson said the same day that the GoConfirm-to-Courtyard run had been about three years at that point. The company publishes no head office and no founding year of its own.
Backers
No funding round has been announced publicly for Courtyard AI and the company names no investors on its own site.
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Quick answers
What is Courtyard AI?
Software that assembles a structured, up-to-date record of a small business — hours, availability, price lists, menus, images, answers to common questions — and makes it readable by AI assistants like ChatGPT, Gemini and Perplexity, so those assistants describe the business correctly and refer customers to it.
Who runs it?
Sam Pajot-Phipps is chief executive and a co-founder. Kirk Simpson, who co-founded Wave, and Peter Carrescia are the other co-founders. Simpson credited the idea to Pajot-Phipps on the TechTO stage in June 2026.
What was GoConfirm?
The consumer venture Courtyard grew out of. Simpson told TechTO in June 2026 that he tried to take GoConfirm into consumer and "we just couldn't make it work", and that coming back to small business "feels like home".
Who from Courtyard AI is in this directory?
Kirk Simpson, its co-founder, who has spoken on the TechTO stage seven times since 2016 — mostly about Wave, the free accounting software he co-founded and sold to H&R Block for $537M.