How Webflow’s CPO built an AI chief of staff to manage her calendar and drive internal AI adoption

So you've built yourself an AI chief of staff?

The AI chief of staff is actually something that I have been trying to build since I started vibe coding. There's a lot of repetitive things that I have to do. For example, like prepping for podcasts and speaking engagements and stuff like that, and so I've built out an agent that preps me.

Let's go into a specific workflow of how this chief of staff actually helps you with do something. I think you did a little prep for this podcast.

I basically prompted and said, "Hey, let's generate a How I AI flow."

Mm.

And so I was trying to get it to tell me what should I actually demo that is going to be part of this chief of staff app? And then what actually ends up getting output is this. It gives me an executive summary. "Here are three different ways you could tell me about yourself and Webflow."

Just the ability to be prepped, even in a few minutes ahead of these things, can really make your life better. [upbeat music] Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive, here on a mission to help you build better with these new tools. Today's episode is all about the AI native executive. We have Rachel Wolan, CPO at Webflow, who's gonna show us how she uses AI, Claude Code, and personal software to run her life and her business day using AI as an executive. She's also gonna show us her formula for teaching teams how to use AI, drive adoption, and get them in those new tools with excitement. Let's get to it. This episode is brought to you by Graphite, the AI-powered code review platform, helping engineering teams ship higher quality software faster. As developers adopt AI tools, code generation is accelerating, but code review hasn't caught up. PRs are getting larger, noisier, and teams are spending more time blocked on review than building. Graphite fixes this. Graphite brings all your code review essentials into one streamlined workflow: stacked diffs, a cleaner, more intuitive PR page, AI-powered reviews, and an automated merge queue, all designed to help you move through review cycles faster. Thousands of developers rely on Graphite to move through review faster, so you can focus on building, not waiting. Check it out at graphitedev.link/howiai to get started. That's graphitedev.link/howiai. Rachel, welcome to How I AI. The reason why we are doing this podcast together is we were sitting at a very recent San Francisco-based AI event, and we were talking about how so much of the discourse is around the AI native PM, the AI native engineer, basically, like the AI native IC, and we spent a lot of time on that topic here at How I AI. But you and I have been chief product officers, and we wanna talk about the AI native executive, and I think your workflow and the tools that you have built yourself are such a great example of somebody with, you know, as I say, a very fancy C-level title, who is actually leaning into not only getting hands-on with these tools, but building things that help them do their job better with AI. So how did you get here? Because I will tell you, not every executive is as into this as maybe you and I are. So what kind of clicked in your mind to get you thinking like, "My job's gonna change. I really gotta figure this stuff out"?