Whitney Stefko Dover, director and senior counsel of policy and legal operations at Ford, says she has replaced one family AI assistant with another.
Three months ago, Stefko Dover said she had built a family chief of staff using a bespoke Claude assistant named Claudette. The agent organized the Dover household's emails and calendars into a 4 a.m. briefing called the 'Daily Dover.' It also handled school schedules, childcare coverage, travel, birthdays, household chores, and a morning text for her husband, Chris Dover.
Now she has shifted to a ChatGPT Work assistant named Gigi. Stefko Dover said her husband, a longtime OpenAI user, encouraged her to try ChatGPT, and an August Substack post from venture firm A16z pushed her to test new agents.
For the family, Gigi offered a better interface, more continuity across projects, and stronger first drafts of emails and PowerPoint presentations, Stefko Dover said. It also made more proactive suggestions without waiting to be prompted.
The move was not a hard one. Stefko Dover said she had already created a guide showing how the assistant worked and how it connected to her family's apps. She uploaded that material into ChatGPT, carrying much of the old assistant's context over.
'Kind of the key here is owning your context,' she said. 'I think it is our job as the users to sort of own the context layer.'
Gigi has since taken on more work. 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.
She said she would not give the agent full purchasing power. '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.
The system is still imperfect. 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 Gigi makes fewer contextual errors than Claudette and remembers more about different parts of her identity. She also said the assistant is not necessarily permanent.
'There's not a final destination here,' she said. 'The power of being a user is this constant iteration.'
Stefko Dover has already added a third assistant, Ingrid, built with Instinct AI, to the family's AI org chart. She said Ingrid can carry out tasks through text messages and phone calls, and she is 'layering Ingrid on top of Gigi.'
For operators and founders, the playbook is simple: own the context, keep the human in the approval loop, and switch tools when the workflow gets better. The winners are not the people clinging to the first assistant they built; they are the ones who keep iterating until the system saves time without creating new risk.
