This as-told-to essay is based on a conversation with Kristi Edleson, a 34-year-old chief of staff at Yutori, based in San Francisco. The following has been edited for length and clarity.
I work at a startup as the chief of staff, and my company’s goal has always been to build an AI chief of staff. It’s funny that when I took this role, I was signing up for that. I wasn’t nervous about it, though; I actually loved the irony.
A chief of staff’s role involves a lot of context switching, and I believe the AI product my company built focuses more on augmenting my skills than fully allowing me to hand things off. The product launched recently, but I don’t see the agent as a replacement for my full role.
I think finding the balance of what lives in your head versus what you’re willing to outsource is the hardest part of working with AI agents all day.
I’m the only non-tech person at the AI company I work for
I’d been working in recruiting for the past 10 years, and I wanted to make a pivot into something more operational. This role happened by chance spring 2025.
I knew the founders from when I was a recruiter at Meta, and they had a catch-all kind of position they wanted to fill at their startup. I don’t think we had even named the job chief of staff yet. As conversations evolved, that’s the title we landed on.
I never saw chief of staff as my forever role, but this job felt like one of the most high-impact operational roles I could get. Who better to give product feedback than someone who is living those tasks daily?
I’m the only non-technical person on the staff, and every day can be different. My job is basically anything the founders don’t have time for. That can be daily operations, finance, HR, compliance, conversations with different vendors, negotiating contracts, and reading contracts.
I give the AI chief of staff agent my manual work
I have our AI chief of staff connected to all my work tools, like email, Slack, Linear, Granola, etc. So it can pull in all of that context and pick up the things that I forgot about.
The chief of staff agent also pulls from my calendar to alert me of what else is on our plate. From there, I decide which tasks I want to hand off.
Before AI agents, I’d see my task list and know I had to do everything on it. Now I ask myself: what items can I hand off to AI so I can find even more meaningful problems to solve? That means I also need to go find those problems.
One of the things that I like to do in the mornings is switch into voice mode, do a brain dump, and unload everything I’m thinking about in any order of chaos. I’m not someone who’s super into having set prompts. That’s why I love where agents are at, at this point. I don’t have to be perfect with my prompts and can ask whatever is on my mind in a very imperfect way, and it will still work.
I like to challenge myself anytime there’s something that feels a little bit manual. How can I have an agent do that on my behalf? That could be anything from drafting emails or Slack messages to having ChatGPT help design our office swag.
I like having reach over what the agent is doing, so it will draft items, like an email, but I approve most of them before it hits send. There haven’t been any major mistakes from my agent, but I have this step in there to safeguard against mistakes the agent could make.
AI helps me negotiate vendor contracts and not ask dumb questions
One of the core parts of my job is negotiating with vendors for different kinds of technical infrastructure tools we need to run our models, like compute or inference. I’m non-technical, so I use AI to help me not ask silly questions in these meetings or slow down our timeline.
About 30 minutes before a call, I ask my agent, “What’s the latest? What’s the sentiment from the team on this tool?” It has my context for how we use certain tools, as well as conversations other teams are having about those tools in a public channel.
I go back and forth with it and sometimes ask questions that I would be embarrassed to ask the team. Then I’m able to show up in vendor conversations, have authority, and get the things we need.
Read more from our Tiny Teams series
I don’t think AI can replace me for financial tasks and strategy mapping
I don’t use the chief of staff AI agent for financial tasks right now, probably because I’m risk-averse, and maybe I’m overcautious. I think finances are probably where I, and a lot of people, draw the line. A bad email is annoying but easy to apologize for. You can’t un-spend $500.
From a personal perspective of keeping myself sharp, I still like to write and handle a lot of tasks myself, then have agents gut-check them, especially anything strategic.
I like to have a mental map of everything I’m working on, and AI sometimes works faster than my brain can keep up. I’m working on how to keep all that information somewhere in my mind, even if it’s getting less attention overall.
There’s a lot of buzz about full automation or the end of certain roles, but I’ve been happily surprised by how much more empowered I feel as a worker now because I have access to basically the world’s most patient tutor.
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