Yutori: AI Mimics the Role of Chief of Staff

Kristi Edleson, chief of staff at Yutori, a San Francisco-based startup, uses an AI version of herself to help manage her workload. She explains that the hardest part is knowing when to do the work herself or delegate it to her AI agent. Although she relies on this agent for many tasks, she refuses to entrust it with managing finances. This essay is based on a conversation with Kristi Edleson, 34, and the content has been edited for length and clarity.

Kristi accepted the role of chief of staff knowing that her company's goal was to create an AI agent for this position. She wasn't nervous about it and even found the irony amusing. The role of chief of staff involves a lot of context switching, and she believes that the AI product developed by her company focuses more on augmenting her skills than on the possibility of completely delegating her tasks. The product was recently launched, but she does not see the agent as a replacement for her entire role.

Kristi thinks that finding the balance between what is in her head and what she is willing to delegate is the most challenging part of working with AI agents all day. She is the only non-technical person in the AI company she works for. Having worked in recruitment for the past ten years, she wanted to transition to something more operational. The role of chief of staff came about by chance in the spring of 2025.

She had known the founders since her time at Meta, and they had a versatile position they wanted for their startup. She doesn't even think they had officially named the chief of staff position yet. As conversations evolved, that title was settled on. She never viewed the chief of staff role as her definitive position, but this job seemed to be one of the most impactful operational roles she could obtain. Who better to provide feedback on the product than someone who lives these tasks daily?

Kristi is the only non-technical person on the team, and each day can be different. Her job essentially involves doing everything the founders do not have time for. This can include daily operations, finance, human resources, compliance, conversations with various vendors, contract negotiations, and reading contracts.

I Delegate My Manual Work to the AI Agent

Kristi has connected the chief of staff AI agent to all her work tools, such as email, Slack, Linear, Granola, etc. This way, it can integrate all that context and take care of things she has forgotten. The chief of staff agent also pulls information from her calendar to alert her about upcoming tasks. From there, she decides which tasks she wants to delegate.

Before AI agents, she would look at her to-do list and know she had to do everything. Now, she asks herself: what items can she delegate to the AI so she can focus on more significant problems to solve? This means she also has to seek out those problems.

One of the things she enjoys doing in the morning is switching to voice mode, brainstorming, and unloading everything she thinks in a chaotic order. She is not someone who likes to have fixed prompts. That’s why she appreciates where the agents are at this stage. She doesn’t need to be perfect with her prompts and can ask any question imperfectly, and it will still work.

She likes to challenge herself whenever there is something that seems a bit manual. How can she get an agent to handle it for her? This can range from drafting emails or Slack messages to using ChatGPT to help design their promotional items.

She likes to have control over what the agent does, so it drafts items, like an email, but she approves them before they are sent. There have been no major errors from her agent, but she has this step to protect herself against potential mistakes.

AI Helps Me Negotiate Vendor Contracts and Avoid Asking Stupid Questions

One of the essential parts of her job involves negotiating with vendors for different types of technical infrastructure tools they need to run their models, such as computing or inference. Being non-technical, she uses AI to help her avoid asking stupid questions during these meetings or slowing down their schedule.

About 30 minutes before a call, she asks her agent: "What’s the latest news? What’s the team’s sentiment about this tool?" It has context on how they use certain tools, as well as conversations other teams have about these tools in a public channel.

She goes back and forth with it and sometimes asks questions she would be embarrassed to ask the team. Then, she can show up to vendor conversations with authority and get what they need.

I Don’t Think AI Can Replace Me for Financial Tasks and Strategic Planning

She is not currently using the chief of staff AI agent for financial tasks, probably because she is risk-averse, and perhaps she is too cautious. She thinks finance is probably where she, and many others, draw the line. A bad email is annoying but easy to excuse. You can’t mistakenly spend $500.

From a personal standpoint to stay sharp, she still enjoys writing and managing many tasks herself, then having them checked by the agents, especially anything strategic.

She likes to have a mental map of everything she is working on, and the AI sometimes works faster than her brain can keep up. She works to keep all that information somewhere in her mind, even if it gets less attention overall.

There is a lot of noise around complete automation or the end of certain roles, but she has been pleasantly surprised to see how much more autonomous she feels as a worker now that she has access to what is essentially the world’s most patient tutor.