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World of Software > Computing > Seattle startup Desk raises cash to automate real estate contract work with ‘better-than-human’ AI
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Seattle startup Desk raises cash to automate real estate contract work with ‘better-than-human’ AI

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Last updated: 2025/11/19 at 1:26 PM
News Room Published 19 November 2025
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Seattle startup Desk raises cash to automate real estate contract work with ‘better-than-human’ AI
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Desk co-founders Gideon Sylvan (left) and Stewart Renehan. (Desk Photos)

AI won’t replace real estate agents completely. But it will accelerate how they do their work.

That’s part of the bet behind Seattle startup Desk, which has raised $800,000 to help real estate agents offload contract administration to AI.

The company’s lead investor is Martin Tobias of Incisive Ventures. PSL’s Geoff Entress and Flyhomes CEO Tushar Garg also invested.

Desk acts as an AI transaction coordinator, taking over administrative tasks such as tracking contract deadlines, drafting paperwork, and prepping signing packets. CEO and co-founder Gideon Sylvan said the tool combines “encyclopedic knowledge” of contracts with the tacit know-how of active local agents.

“Every agent wants to avoid paperwork, but most agents would rather do the work themselves than wait three hours for their assistant to handle it,” Sylvan said.

More than 500 agents in the Seattle area are using the software, including two board members of Northwest Multiple Listing Service. Desk said it is processing 100+ closed transactions per month, with inaccuracies on fewer than 0.2% of deals.

Desk, founded earlier this year, is also targeting brokerages to help them maintain transaction records.

Sylvan said the February release of Claude 3.7 was a breakthrough, transforming how accurately AI can read and interpret real estate contracts — including edge cases like handwritten signatures and custom conditions. “Suddenly complex contract assistance went from ‘this will be possible one day’ to ‘this is truly better-than-human,’” he noted.

While some companies are trying to replace real estate agents, Sylvan said that it’s more likely that AI becomes the “execution layer.”

“Being an agent is a contact sport filled with 10-second phone calls and short texts,” he said. “Deals come together when two agents trust each other. But the paperwork? I could care less if an AI put the paperwork together. That’s just inevitable.”

Sylvan and co-founder Stewart Renehan previously launched Lotside, a startup billed as “Zillow for house flippers.” That company didn’t quite take off but still has 20,000 monthly users, Sylvan said.

Sylvan also built a U.S. brokerage, while Renehan led data science at a PushSpring, a marketing tech startup acquired by T-Mobile in 2019.

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