Town's CEO Says Most People Don't Know What to Ask AI

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Most people still use ChatGPT and Claude as a replacement for Google Search, not to get work done, says Jean-Denis Greze, CEO of the AI assistant startup Town. He told Fast Company the main reason is simple: people do not know what to type into the chat box. "Putting someone in front of an empty box and asking them to write what to do ... that's not onboarding," he said.

Town announced a $108 million Series B on Oct. 19, co-led by Forerunner Ventures and Menlo Ventures, at a $1 billion valuation. Greze cofounded the San Francisco company with Tony Vincent in late 2024. He was previously CTO of Plaid, where the engineering team grew from about 20 people to 350. Town is aimed at small-business owners and mid-market firms.

Small workflows

Greze conceded that ChatGPT or Claude could do most of what Town does, and that large rivals such as Google, Microsoft and OpenAI may win on distribution. "As a startup, that's the risk you're taking on," he said.

One customer is a small travel firm that rents cars and gear and runs its business over email. Staff send photos of damaged items to a central person. Town now gathers those emails each day, checks the CRM and drafts replies. The firm used to write 10 to 12 such emails a day, which took 25 minutes. Now it takes five.

Town calls its product a "Townie" rather than an assistant or chief of staff, because Greze thinks those labels carry human expectations. He compares the technology to a browser or a device: the share of time people spend in a browser or on a phone will fall, he says, while the share spent talking to an AI will grow. Town's main plan costs $50 a month, and he says consumer use cases are subsidized by business ones.

Voice, trust and pace

Next, Greze is focused on live voice and on what he calls agent-to-agent work, in which one person's assistant asks colleagues' assistants who knows a contact at another company, without revealing private details.

On trust, he said such assistants only work if people believe they act in their interest, and that paying for a service is what makes that possible. The pace of the market is the hardest part of the job, he said. Ideas that took nine months to copy are now copied in a month or two. Greze, who is 47, said he has never worked this hard. He said he is either ecstatic about shipping before OpenAI or in fear of a tweet from Sam Altman.

Outside work, he has Town research food blogs each Monday and propose four classic and four new restaurants for his Sunday date night with his wife.

Source: Fast Company