Claudette is on a performance improvement plan.
Three months ago, Whitney Stefko Dover, a director and senior counsel of policy and legal operations at Ford, told Business Insider that she had vibe coded her family a chief of staff using a bespoke Claude assistant named Claudette. The agent turned her family's emails and calendars into a 4 a.m. briefing called the "Daily Dover." It was an early morning email that organized school schedules, childcare coverage, travel, birthdays, and household chores. It also drafted a useful morning text for her husband, Chris Dover.
Claudette "probably saved our marriage," she previously said.
Now, there's fresh competition for the chief of staff role — but Claudette hasn't been fully fired. Yet.
"I'm not convinced that, like, next month, Claudette won't be the superior chief of staff," Stefko Dover told Business Insider. "She's on a PIP."
Now, Gigi, a chief of staff she built in ChatGPT Work, is the fresh-faced agent parsing through the Dover family calendar. Stefko Dover says her husband, a longtime OpenAI user, encouraged her to try ChatGPT. An August Substack post from Silicon Valley venture capital firm A16z gave her another push to try new agents.
"Turns out I have a lot of tool bias, which was unexpected," she said about her reluctance to abandon Claudette after months of refining.
For her family, Gigi offered a better interface, maintained more continuity across projects, and produced stronger first drafts of emails and PowerPoint presentations, Stefko Dover said. It also made more proactive suggestions without waiting to be prompted.
And the switch to ChatGPT was surprisingly painless. Stefko Dover had previously created a guide explaining how the assistant worked and connected with her family's apps. She uploaded that material into ChatGPT, bringing much of the old assistant's context with it.
"I think kind of the key here is owning your context, right?" she said. "I think it is our job as the users to sort of own the context layer."
Since the switch, Gigi has taken on even more responsibilities, Stefko Dover said. Every Friday, it reads a grocery list shared with the family's nanny and fills online shopping carts.
Stefko Dover still reviews and pays for the order herself, because it still needs some supervision.
"If I were to do that, I'd probably get, like, a $500 credit card limit so that there wasn't, like, Gigi purchasing diamonds on Rodeo Drive," she said when asked if she'd give her agent purchasing power.
At one point, it suggested that her husband send flowers to his best friend's wife after mistaking her for a relative. A grocery haul recommendation included 12 boxes of bow-tie pasta.
Still, Stefko Dover said it makes fewer contextual errors than Claudette and remembers more about the different parts of her identity.
She told Business Insider that Gigi shouldn't expect to have the job forever.
"There's not a final destination here," she said. "The power of being a user is this constant iteration."
She wasn't kidding. Since the interview, Stefko Dover said she has added a third assistant to the family's AI org chart: Ingrid, built with the buzzy, invite-only Instinct AI, which can carry out tasks through text messages and phone calls.
"I'm layering Ingrid on top of Gigi," she said. "Example: Instead of me sending Chris a text message with to-dos, it can just talk to his agent (since we've both activated this capability), and his agent can then go perform tasks on his behalf!"
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Ben Shimkus is a reporter for the Business News desk. He writes about cars, transportation, retail, and jobs. Ben's reporting has appeared in Rolling Stone, The Verge, Automotive News, USA Today, AutoBody News, LGBTQ Nation, TopSpeed, and Out Magazine. He's also held staff writing positions at The U.S. Sun and the Daily Mail. He graduated from NYU with a Master's in journalism in 2024. Email Ben at [email protected] or message him privately on Signal at bshimkus.41.
