How Webflow’s CPO built an AI chief of staff to manage her calendar, prep for meetings, and drive AI adoption | Rachel Wolan

Rachel Wolan, the chief product officer at Webflow, has embraced AI not just as a product leader but as a hands-on builder. A coder since age 16, Rachel has returned to her technical roots by creating a custom AI chief-of-staff application that helps manage her executive workload. In this episode, she demonstrates how she uses personal AI software to prep for meetings, triage her calendar, manage emails, and even get brutally honest feedback about how she’s spending her time. What you’ll learn: How Rachel built a custom AI chief-of-staff application that integrates with her calendar, email, and moreWhy building personal software can be a gateway to understanding AI’s capabilities for executivesHow her AI agents help her prep for podcasts, dinners, and meetings with just-in-time informationThe technical approach to building personal AI software using markdown files, API tokens, and multiple LLM interfacesHow Rachel organized company-wide “builder days” that dramatically increased AI tool adoption across her organizationWhy she believes executives must lead by example in AI adoption to authentically drive organizational change— Brought to you by: Graphite https://graphitedev.link/howiai—Your AI code review platform Atlassian for Startups https://atlassian.com/startups/howiai —From MVP to IPO — In this episode, we cover: (00:00 https://www.youtube.com/watch?v=BTcG59ZR9sg) Introduction to Rachel Wolan (02:26 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=146s) Why Rachel started leaning into AI (06:26 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=386s) Building an AI chief of staff (08:17 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=497s) Prepping for the podcast (10:00 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=600s) Rachel’s morning flow with her AI chief of staff (14:14 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=854s) Designing a personalized interface with custom note cards (16:34 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=994s) Getting “brutal truth” feedback from your AI assistant (19:34 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=1174s) Email triage and management workflows (23:31 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=1411s) Prepping for networking dinners and events (28:18 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=1698s) The result of building an AI chief of staff (30:09 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=1809s) Organizing “builder days” to drive AI adoption (35:38 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=2138s) Measuring the impact of AI adoption initiatives (38:00 https://www.youtube.com/watch?v=BTcG59ZR9sg&t=2280s) Lightning round and final thoughts — Tools referenced: • Claude: https://claude.ai/ • Claude Code: https://claude.ai/code • Cursor: https://cursor.com/ • Google Calendar API: https://developers.google.com/calendar • Gmail API: https://developers.google.com/gmail • Webflow: https://webflow.com/ • Figma: https://www.figma.com/ • Make: https://www.make.com/ • Hex: https://hex.tech/ — Where to find Rachel Wolan: LinkedIn: https://www.linkedin.com/in/rachelwolan/ X: https://x.com/rachelwolan Webflow: https://webflow.com https://webflow.com/ — Where to find Claire Vo: ChatPRD: https://www.chatprd.ai/ Website: https://clairevo.com/ LinkedIn: https://www.linkedin.com/in/clairevo/ X: https://x.com/clairevo — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Claire Vo?

  So you've built yourself an AI Chief of Staff.

• 0:03Speaker 01

  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 an agent that preps me.

• 0:18Claire Vo?

  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.

• 0:25Speaker 01

  I basically prompted it and said, hey, let's generate a How AI flow. 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.

• 0:43Claire Vo?

  Just the ability to be prepped even in a few minutes ahead of these things can really make your life better.

• 0:52Claire Vo?

  Welcome back to How I AI. I'm Claire Voe, 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 Wolin, CPO at Webflow, who's going to 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 going to 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,

• 1:34Claire Vo?

  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.

• 2:10Claire Vo?

  Developers rely on Graphite to move through review faster so you can focus on building, not waiting. Check it out at graphite dev dot link slash how I AI to get started. That's graphite dev dot link slash how I AI. 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.

• 2:52Claire Vo?

  But you and I have been chief product officers and we want to 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 going to change? I really got to figure this stuff out.

• 3:31Speaker 01

  I started coding when I was 16 and you know, it's obviously been kind of a lifelong journey of building and tinkering and you know, making mistakes. And so I feel like I kind of built that resiliency pretty early in life. And now in my current role, you know, I probably hadn't coded in about, you know, six or seven years. And then when all of the new app gen tools came out, I think lovable is like one year old now. I was like, hey, I'm going to try this out and you know, it was, it felt magical, right? And I'd kind of played around with some of the earlier versions of GPT. But you know, when it was, when kind of like vibe coding started coming to the scene,

• 4:13Speaker 01

  I actually built an app to capture my kids' memories. And that was the first vibe coded app that I built. And I built it in a weekend and it was, it just felt like something completely different than anything I'd ever built before. And, you know, here we are a year later and this is, you know, now I'm like sitting in Claude code all day and I, you know, this is an app that I kind of like am continually maintaining. You can see that I'm running it on local host. And, you know, I've probably have built dozens of apps this year. We just launched our app gen product. So I feel like a lot of times when you're building AI native products, you also have to be just in the weeds a lot and making mistakes. And I'll show you like this product is not perfect.

• 4:56Speaker 01

  This is a product for one person right now. And so that's, that's really, you know, kind of how I got started. And I think it's, it's something that now is just part of my day to day. This is how, this is my daily driver.

• 5:09Claire Vo?

  This is a story I hear a lot. It mirrors my own story. This is probably why you and I get along so well, which is, you know, started coding very early, a lot of self-taught stuff. And then, you know, get into these jobs where coding hands on keyboard wasn't my job. And then in 2023, 2024, it just became easier to go zero to one on stuff. It wasn't that I didn't have technical skills. It was just, I didn't have time, time to do things. And so the ability to, you know, do AI assisted engineering or vibe coding was, it just brought me back to the love of coding and building things. And so I hear that a lot. I certainly feel that a lot.

• 5:52Claire Vo?

  The second thing I hear a lot that I tell people who are like trying to motivate themselves to learn some AI skills is find something personal to work on. You said like this memory app for your kids and do it in a weekend. You will get hooked. I think these vibe coding platforms are some of the most addictive games on the market right now. And so again, you don't have to start with something at work. You can start with something that's personal. And I think once you get hands on and realize what's possible, it's hard to think that your day to day job is going to be the same. So let's get into what you built because I feel like I need this. So you've built yourself an AI chief of staff.

• 6:36Claire Vo?

  Tell us more and how you're using it in your everyday life.

• 6:40Speaker 01

  Yeah, so the AI Chief of Staff is actually something that I have been trying to build since I started Vibe Coding. So this is actually the first app that I tried and then didn't work the first time that I tried it. And then I've just been kind of continually trying to build it. And what you'll see here is like kind of rotating agents. I've just kind of been, you know, ticking away different use cases. And then a big part of this is also, you know, I really want to help my team level up. And so it would be inauthentic for me to tell them, hey, you need to prototype with AI if this isn't something that I'm doing every single day.

• 7:22Claire Vo?

  I completely agree. And one of the things I want to call out about how you're talking about building this software is, one, you're building it for an N of one. You're building it for yourself. So it can be really hyper customized. Two, you're building sort of a multimodal interface to this in which it can be a web app, or it can be something just like a little bit more close to the metal in terms of in the terminal or in cursor. And then I love this idea of being able to build ephemeral widgets that are useful that you can just toss away. Like, you may never look at this Q4 roadmap after Q4 again, and you may want to do it completely differently the next time. You can build these like little

• 8:04Claire Vo?

  personal ephemeral apps and then toss them away when they're not useful to you. And so I think software has become as accessible as documents have if you can lean into some of these tools. And so 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.

• 8:24Speaker 01

  I did. So I will actually run different terminals that are all running Claude. I do this partially because, you know, I want to make sure that I'm like not using too much context. And then I find that When I'm asking questions that are of a similar ilk, I get better answers back in that same terminal window. But I basically prompted it and said, hey, let's generate a how AI flow. And so I was trying to get it to tell me like, what should I actually demo? That is going to be part of this chief of staff app, right? So it knows this structure. And then what actually ends up getting output is this. So this is, it gives me like an executive summary.

• 9:07Speaker 01

  You know, if we were to vamp, it would be like, hey, here are three different ways. You could tell me about yourself and web flow.

• 9:14Claire Vo?

  I just love that you can do this on an ad hoc basis, get a structured output, feel very prepared. I don't know if you're like me and don't, don't tell my, my teams that work for me. I am a just in time executive, which means like the two seconds before I'm walking into a meeting, that's the time I have to prep for that meeting with very rare exceptions, because you are just back to back to back to back to back to things. I say sometimes to people, the number one skill you need to learn as an executive is improv, because you are just dropped into a wide variety of contexts. You need to be able to think on your toes. And so just the, I had a chief of staff and just the ability to be prepped, even in a few minutes ahead of these things can really make your life better.

• 9:57Claire Vo?

  So let's go through, okay, this is a very specific example. It's sort of our meta example.

• 10:02Speaker 01

  Yep.

• 10:02Claire Vo?

  On how we're going to go through this show, but let's talk about your morning triage and how you start your day, every day, using this AI chief of staff.

• 10:11Speaker 01

  That sounds good. So in this case, what I actually gave it was a question. I said, hey, how can I make my week, my last week better? What, what could I have done? Because I think that I don't have a chief of staff anymore. I used to have a chief of staff at another company. And so I knew that this was something that they would be like, kind of combing through my calendar and like, hey, you're not blocking your energy, right? And you're, you're not like, kind of taking care of yourself. And so, you know,

• 10:39Speaker 01

  The other, the, the main thing that they kind of called, called me out on, which I thought was really funny. So we just had our customer conference about a month and a half ago. And, you know, I haven't taken quite as many customer calls. And it's basically calling me out and saying, you know what, you're not spending enough time with customers. And that's where you get energy from. And so it's basically like doing a time analysis on my external calls. I'm like, how is that possible? And again, it did pick up, it wasn't like a hundred percent correct. And so I think that, but, but it was kind of like a signal to me. I'm like, oh, this is a place where I need to go and like reinvest. Right? And it's like, you're a CPO with like no regular visible customer contact, fatal flaw. And I'm like, oh gosh. It's very like dramatic, right?

• 11:22Claire Vo?

  Well, how does this actually access your calendar? How have you technically built this?

• 11:26Speaker 01

  Good question. So I went and I got a token from Google Cloud. And I basically, I'm not going to show it, but I, I basically have it like in my .env file. And so, but I didn't really like set that up myself. I mean, I knew that this was the way that I was going to need to construct it because I had built other apps before. But let's see if I can find it. So this is like my .env file. I'm not going to show it to you because I'll have to like burn all the, the tokens I have in there. But it's basically has a bunch of variables. And so one of those variables is my Gmail. And then it walks you through how to actually go and set that up. One of those variables is my Google Calendar.

• 12:08Speaker 01

  And, you know, then I give it certain authorization. So in the case with Google Calendar, it can only read my calendar. In the case with Gmail, it can only create drafts. It can read, it can archive, and it can create drafts and label. And so a lot of this is like thinking about how do I, you know, put the right guardrails in place? It's kind of like thinking about software, right? How do I put the right guardrails in place so that I don't make mistakes or the agent doesn't make mistakes? It's kind of janky software, right? Because I, I mean, I, because I'm like, oh, this is like pretty powerful. And then a lot of times I'll like go and kind of take some of the power away. When I realize I've given it

• 12:49Speaker 01

  like too much, you know, too much authority to act on my behalf. And so I think that's, you know, part of it is also like, Me populating my own, you know, kind of intuition about what feels good in working with agents and what feels like it's kind of like overstepping.

• 13:08Claire Vo?

  Yep. And so are you coming to this every morning? And this is sort of a meta-analysis of your calendar, which again, I've had a chief of staff. We did every Friday where we're like, what, what are you doing, girl? Like, let's, let's fix this. But tell me how you would use this on a daily basis.

• 13:23Speaker 01

  So tell me about my day tomorrow. What can I delegate? And so this will run for a couple of minutes. And when it comes back, it'll tell me this is what's coming up tomorrow. This is what I think you can actually, you can do something else. This is, you know, I think the, the way that I would like to make this smarter is this is who you should delegate to. And then, you know, I'm still kind of working on my Slack agent, so I can't show you. But what I want to do is basically like send notes to my admin and be like, hey, could we go do this?

• 13:57Claire Vo?

  And is this fetching the calendar events through an MCP? Is it, is it some custom code that you wrote?

• 14:03Speaker 01

  This is fetching it through an API token. I don't think that there's an MCP that is like a

• 14:11Claire Vo?

  Official.

• 14:12Speaker 01

  Official MCP, but what you kind of see, this is why sometimes I like looking at my briefing. So other things that I do here, you know, I actually have like a little, you know, like a little like note card that I like to make for myself. I'm like, I did prep for you. That's good. And then, you know, I'm basically kind of looking at this. The thing that I like about it is it like makes it just very easy for me to get a snapshot and, and view it. But I'm still kind of like iterating on what do I want this to be like?

• 14:44Claire Vo?

  Let's just take a pause really quickly on your web app while this is running in the background. And what I love about what you've designed is, look, we're all running on Google Calendar or whatever. But you want it to look a certain way. You want it to be designed a specific way. You want to have, can you show us that little note card really quickly?

• 15:08Speaker 01

  I, I got this idea from Mark and Drayson about like, what are my top priorities for the day? And then did I actually accomplish it?

• 15:18Claire Vo?

  And hold your horses real quick. It's also extremely cute. So for people that are not on YouTube and are listening, it is actually designed like a blue lined note card and it does this little flip. Look at you, product person. I mean, this is one of those other things where when people talk about personalized software, they don't get to talk about the little like pieces of zhuzh that you get to put in the app that just make you really happy. Okay, so sorry, sidecar on design. So your top priorities.

• 15:51Speaker 01

  Yeah, I just as a side note, like I almost redesigned the app last night because I was like, oh, I wish it kind of felt more like Apple Notes. And I think that's like part of what is fun is like, okay, what would that actually be like if I translated this app and I had like a theme for it? And so there's something, there's something really fun about like actually getting to design again, but not actually, I mean, it takes the amount of time. It's not, it's not at like the pixel level perfection of the incredible designers on my team, but it does at least convey like, you know, there's a certain je ne sais quoi of this like app that I'm trying to capture to make myself happy.

• 16:32Claire Vo?

  Yeah, I love it. It's so great. Um, okay.

• 16:35Speaker 01

  So here we go. Here we go.

• 16:37Claire Vo?

  Yep.

• 16:39Claire Vo?

  Your Chief of Staff is very mean.

• 16:43Speaker 01

  I tell it to be mean to me. That's why I wanted to like keep me in line, you know, I'm one of those people who likes to try to take on too much, I think, sometimes. Okay, so it's basically telling me to make certain meetings async. That's a great idea. It's telling me to delegate a couple of these. This is also probably a great idea. I don't think I can delegate this one, but good call. It's telling me there's too much clutter on my calendar. This is one of those things where somebody just like put something in my calendar. I don't know this person. So that's definitely optional and I haven't accepted. And then it's like, can whatever director cover this and send me a summary? Can, right? And this is really helpful. This is like forcing me to think about,

• 17:27Speaker 01

  okay, do I actually need to attend all these things that I've signed up for? And can I give myself a break during the day to do some work and, you know, maybe get home to my family at like a reasonable hour?

• 17:37Claire Vo?

  I love these delegation messages because just as a human, it is very easy to identify meetings that You don't need to go to, and then you're like, oh God, how do I say I don't want to go to this meeting?

• 17:51Claire Vo?

  So even getting that draft where you could just find, I could just copy paste that into Slack is such a useful friction reducer in managing your own time. And again, we're talking about the AI native exec just too busy, overbooked, underprepped, really just wanting to spend our time vibe coding. So I think this is really, really useful. And again, I like this because it's very conversational as a chief of staff might be. It really helps you sort of figure out what you can do with your calendar. And then I like how it's mean to you. What's the brutal truth? Let's look.

• 18:30Speaker 01

  The brutal truth is that.

• 18:34Speaker 01

  I'm like, yep.

• 18:37Claire Vo?

  It's kind of being a senior PM sometimes sounds more fun.

• 18:39Speaker 01

  I know. I'm like, is that bad? Is that a bad thing?

• 18:45Claire Vo?

  So for those again, who are not watching, the brutal truth is you're operating as a senior PM, not a CPO. You're reviewing PRDs, approving scripts and recording marketing videos.

• 18:57Speaker 01

  I mean, they're calling a spade a spade.

• 19:00Claire Vo?

  This is the behind the curtain stuff. And I tell everybody this about the origin story of chat purity, which is they're like, why did you build chat purity? And I was like, man, because no matter how fancy of a title I got, I still was writing PRDs all the time. And so this is, this is really, really great. And then I love this idea of like, the only thing that will matter in six months are, is this conversation. What an amazing way to level up. So chiefs of staff that are watching here, you need to end every meeting with your exec with the brutal truth. And build this for yourself. Okay. So this gives you a really good prep for your day. I'm presuming you do a very similar workflow for email as well. What is outstanding?

• 19:42Claire Vo?

  Can you just walk us through maybe just some of the problems that your email chief of staff solves?

• 19:48Speaker 01

  Yeah. I mean, I think that my biggest problem is that I'm, I have like five, I'm like 500 emails deep in my email. But it's basically archiving a bunch of stuff that I don't need to, it's keeping a few things in the inbox and then it's drafting a few responses. And you know, a lot of this is like, I've been kind of like continually updating this particular agent to know where to draft responses. Sometimes it drafts responses, you know, like some random SDR inbounds to me and I'm like, no, no, no, you don't need to like draft responses to this person. But a lot of times it'll be like, you know, somebody from like a, like a partnership type of email will send me an email and it'll tell me, hey, you need to pay attention to this email.

• 20:32Speaker 01

  So a lot of it is like trying to also know, like when somebody's waiting on me and asking for some document to get shared, right? And so, you know, this is like kind of a cursor view and then I can go through my inbox like very, very quickly. I think the Slack version of this is going to be like an absolute game changer since we operate almost internally in Slack 100%. But that one has been a lot harder to digest, even with like the, where the models are at. It's like almost too much data to triage.

• 21:02Claire Vo?

  Yeah.

• 21:03Speaker 01

  So I feel like that's like my next, that's my next hill to climb.

• 21:07Claire Vo?

  What does that say about what we expect of humans? That we are expected to triage a vast amount of very disparate information with a lot of disconnected context, so disconnected that fancy pants large language models cannot make sense of it. But for some reason, us with our meat brains are expected to be able to do this. And I just think that is such an indictment of how we're expected to navigate the massive amounts of information as, as people that are working on teams in these asynchronous or semi-secretist ways.

• 21:46Speaker 01

  Yeah, I mean, I think it's also become so different during, you know, like post pandemic, and especially if you're working for a remote organization. And, you know, I think that that, you know, that we're obviously only, what, you know, four years, five years into that experiment. And so I think that we haven't like, the tools haven't quite caught up with what we need to kind of declutter our brains through that kind of transition. So I still think we're in like the early days of how to effectively do remote work, but that's like a different topic for another podcast.

• 22:22Claire Vo?

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• 23:06Claire Vo?

  to the next generation of builders. They know how important it is to focus on building the right things early. Whether you're in the sticky note stage or well on your journey, teams at any stage can work smarter together. It's never too early to start with Atlassian. Head to atlassian.com/startups/howiAI for more details and eligibility. Okay, I want to do one more fun chief of staff example before we go on to our next workflow, which is how do you prep for dinners? Tell me about just this little tab is calling my name. I must know.

• 23:44Speaker 01

  All right, so I'm going to dinner tonight. It is called the CXO Collective. And what I did was I took a screenshot of this guest list. And so, you know, I'll show you it's, you know, I basically literally just took a screenshot of this guest list. And then I dropped it in here. So you can see the image that I dropped in here. And then it read each of them. And I haven't looked at this yet, so I can't tell you if this is good or not. Buyer beware. It's free. And then it went and did search on every single person on that

• 24:23Speaker 01

  list. And then I have an agent that is basically kind of like going and like doing more analysis on like this happens to be one of my colleagues who's going to the dinner guy leaf. And so, you know, like he was acquired. So it looks like they're like actually identifying the right person. So what it does is it goes and it does a search on the web, then it does a search in LinkedIn, then it goes and tries to do like more web search. And, you know, it's like, hey, this is your colleague. That's pretty good. And it also has like, the other thing that I would say that I have given this is a lot of context about me. So let me see if I can just show you a couple of examples. Yeah, so I have like, some general about me documents, like, this is

• 25:07Speaker 01

  from like some communication workshop that I went to where this is like, kind of how I want to communicate. This is like, personal resources about me. And they're all, I try to do everything in Markdown, just so it's easier for the models to understand it. And then this, I actually generated like, I try to generate this maybe once a month of like, what are the new Webflow products, off of our release notes, so that it kind of like knows everything that we've released in the last couple of years. And so then it kind of knows a lot about me. And then it's telling me about the venue. And then it's like, what are hot discussion topics? And, you know, I'm going to like, an AI marketer, kind of AEO answer engine optimization dinner. And, you know, then it's like, created this full prep doc. So I'm like, okay, that's great. And then,

• 25:52Speaker 01

  what you can see is, I'm like, can you add it to my dinner research tab? So the, everything that's in dinner research is actually a Markdown file. So that's the other way that this has like, worked really well. I could go and open this up in Cursor if I could find that file. And then, but really, I just find it easier for something like this, to go into my Chief of Staff. And then, let's see, pretty, oh, it's gonna be a nice dinner. And, you know, it's like, these are my priority connections, like, conversation starters. You know, I'm like, this is like, kind of the introvert in me, or maybe the ambivert trying to like, be prepped.

• 26:33Speaker 01

  Just I love this.

• 26:35Claire Vo?

  Because I am an introvert. I get invited to these dinners all the time. And this is, this is really great. One of the things I want to call out for how AI watchers and listeners is I recently did a mini episode on how to generate a markdown powered personal app. And so, you know, instead of having to toss these files into a database or to a file store, you can just store them as markdown files inside your repo and then display them on the front end using a markdown renderer and then it looks really nice. So I think, again, when you're building sort of a personal app for, you know, your own research or context,

• 27:18Claire Vo?

  just use markdown files as a source of truth for content and display those markdown files in a nice way on the front end. Simplifies things. You don't have to think about a database. And the benefit is then any of those markdown files can be referenced by any of the agents that you use for other things. So you could go to Claude Code and say something like, "Hey, grab the dinner prep from that steakhouse dinner I went to last month and remind me of who that person was at Twitter that I was supposed to talk to. I never got to talk to her and I want to send her an email." Like, that kind of stuff can really help just make not only the the software, the personal software better, but also just your use of overall agentic tools a lot better.

• 28:02Speaker 01

  Yeah, I feel like it's been a game changer to start using markdown files. And then also start using markdown or even like PRDs. So a lot of times I'm like updating this app and I have like kind of an ongoing PRD that's like self documenting this app.

• 28:18Claire Vo?

  I love it. And so what do you think the result of you building this chief of staff has been? How has it helped you? Are you saving time? Do you feel like your life is a little bit better? Obviously, you've learned more about AI. Kind of what is the outcome you've gotten here?

• 28:32Speaker 01

  Yeah, I think that the biggest outcome for me has, number one, been really being like close to the metal in terms of like building out AI products. And I am the one that is like, you know, able to have very, very detailed conversations. Like, for example, I didn't get a chance to this morning, but I'm gonna go and start using Gemini 3 as part of this app. And there's certain types of, it's gotten me very close to our codebase as well. So, for example, I, you know, I have like, I use Codex a lot. Right now, I'm only using it on this particular app, but I could like go and be like, tell

• 29:13Speaker 01

  me about this app. How is it built? And I think that that's really important to be able, so I also obviously have access to our repo, our monorepo. And so a lot of times, like this happens to be for telling me about this repository, right? But this is like a really good starting point for anybody who's gonna go build something, because then you can start to understand, well, how is this app that we build actually built? And I think that that it was almost something that was inaccessible unless you were sitting there and like reading code, which, you know, sometimes I do, but I think that this is like very accessible to anybody.

• 29:56Claire Vo?

  This is awesome. And again, you can just add modules, you can spin up new quad code interfaces, and then you can design whatever you want on the front end. It could look however, however you want, which I love. Well, I want to flip this to another use case in the second half of our episode, which is a little bit less about how you personally use AI, even though we've shown that a little bit. I do want to talk about how you get AI into your team. And so I want to talk about your builder days, because I think, you know, what you're setting a really great example of is I'm a CPO. You say you think of yourself as an IC CPO. I do as well, which is like, we're gonna do the work, we're gonna get into it.

• 30:40Claire Vo?

  Part of it is setting an example of how the work gets done. And then part of it is you have no credibility if you don't actually know what you're talking about to convince other people to do something in their job. And so this is a little bit of a different how AI, which is how I AI into an organization. And you've done these builder days, so tell us a little bit more about this.

• 31:03Speaker 01

  Yeah, so we did a builder day last Wednesday. So this is pretty fresh and that's the second builder day that we did in this particular way. So maybe first I'll talk about the results because I think that it's actually helpful to see that. So this is a screenshot from Hex that was a dashboard that shows all of the roles under my team. And then after builder day one, which was just design, we had maybe half the team using Cursor. And what I think is really cool is like very few people were using it before that. And then it became this like kind of sustained use because we helped people get over that hump. And, you know, not everybody. And then we just did a builder day, part two.

• 31:47Speaker 01

  And I'll talk about a little bit about how we actually ran that builder day. But we had design, product, data science, user research, analytics, engineering, you know, lots of different functions, build for builder day. And what we realized in order to get more people over that hump, and by the way, I don't think this is everyone, I think we actually had something like 80 plus prototypes that were actually built that day. Not all in Cursor. But, you know, this is like, I'm excited to see like, does this continue to be sustained? Is this something that people start to use as part of their day to day? And, you know, I really think about an organization kind of similar to any normal distribution curve where you're going to have, you know, it's the innovator's dilemma where you have

• 32:32Speaker 01

  like the early adopters, right? And, you know, we've, we identified a lot of these early adopters here back in like March, let's say. And then those people actually built out the scaffolding for May for our first builder day. And then as we had more and more people working, we actually had like a bigger user group that was inside our organization that were maybe the early majority. And now we're starting to, you know, build into the kind of like middle part of that distribution, or even maybe some of the laggards that are by just trying to reduce the friction and then trying to lean into the people who are really embracing that technology. And I think it needs to be both, you know, a top-down mandate. Like, I tell

• 33:15Speaker 01

  my team, hey, you can't get into a meeting with me without a prototype. So there's a mandate, but then it's also a bottoms up. So I think it kind of has to go both directions.

• 33:26Claire Vo?

  So this is the outcome you're trying to drive, which is like, we want to use these tools. We want to feel like not just during this spike, but overall in our day to day, those tools are useful to my team. And so explain to us what a builder day is and how it drives you towards that outcome.

• 33:41Speaker 01

  Yeah. So we're builder day is when our entire organization stopped doing what they're doing and they built a prototype for whatever they wanted it to be. And the goal was really to boost confidence, spark adoption. And so we had a couple of different types of tools. We lit up Cursor, Figma Make and Webflow. And I'll talk about how we actually enabled the organization around that. And then we actually had like different tracks for different types of teams. So we had different assignments for product. We had, you know, you can explore a new product idea. You can validate user interactions. You can test product concepts. You can build a full end-to-end workflow. You know, we did. So we also had them do

• 34:24Speaker 01

  like a warm-up assignment. And then we basically had like support channels. So we had a couple of engineers that were on call for this. We ran like a judging panel. So like me and the CEO and a couple of other cross-functional leaders were the actual judging panel. We had prizes, recognition, different categories. And then we, you know, really focused on like, how do we measure success and do this again? And so, you know, this is something that is like evolving for us. This isn't, we definitely aren't like, we've nailed every single part of this. But I was really encouraged to see so many people actually like taking one step outside their comfort zone.

• 35:00Claire Vo?

  Amazing. And so this is something that for the leaders There's out there that are just looking to like, how can I accelerate adoption? How can I up, you know, upgrade our learning and development in the org, not in this ad hoc way? This is 100% the advice I give them, a builder day, a hackathon, and it has to be a combination of tools, access, education, real prototypes and prizes. People love, love the prizes. And so if you can make this something really fun, I think it's a super effective way to engage the whole organization in just becoming more AI, AI native. And I would, I would just ask you, you know, what's the feedback from the team? What's the kind of before and after you're seeing

• 35:45Claire Vo?

  from the team before and after these builder days?

• 35:48Speaker 01

  Yeah. I mean, so I actually like copy and pasted literally the feedback that we got from our survey. So you can go and see it. Most people were not frustrated, which made me really happy, which meant that we had like gotten around of the, a lot of the technical issues. I think people found it fun, empowering, motivating and eye opening. I don't think people understood what was possible.

• 36:09Claire Vo?

  Yeah.

• 36:10Speaker 01

  And that to me was like the most heartwarming thing I could possibly imagine is all of these people, I call it getting blue pilled, right? Like all these people all of a sudden like stepped into a new part of their professional journey and that, that just made me really happy.

• 36:28Claire Vo?

  So to recap this for any of the CPOs or executives or aspiring CPOs or executives out there, you know, a couple of takeaways from this episode is one, there is just no substitute for getting your hands on to these tools, especially coding things. I think is very important in almost any role. I've been saying over and over and over again, this is the era of the hard skill. And one of the hard skills I just think is going to become more table stakes is at least being able to use code to get things done, even if you can't be an exceptional software engineer, that you can build yourself custom software, especially markdown based, that has both sort of agentic

• 37:10Claire Vo?

  access properties where Claude Code could use it and web UI, you could run it locally. If you don't want to deploy anything, it's not a big deal. And it also helps you kind of bypass some of the security concerns around using third party tools because you're running things locally, you're using, you know, internally approved API keys, all those sorts of things kind of help you stay sandboxed. In your environment and then organizationally and culturally, these builder days can have a very repeatable structure. And so if people want this, I think you're going to share this repo and this resource with us. So you can look at it. There's a repeatable process for onboarding, educating, engaging,

• 37:51Claire Vo?

  and driving sustained adoption of AI in your org through these sort of spikes in builder days. And then you're just having fun. Are you having fun? Cause I am having so much fun right now. And that's one of the reasons why I'm spending so much time on AI is it's just, it's, it's better than it used to be for my job.

• 38:10Speaker 01

  I think it's the most amazing time to ever be doing this job in the entire time that I've been doing it. It's, it's a hard job. I think it's just building products is hard, but it's never been more fun. And the possibilities have never been, you know, quite so unlimited.

• 38:26Claire Vo?

  I completely agree. Okay, let's do some lightning round questions and then let's get you back to, I just have to call it out, your two cursor windows.

• 38:37Claire Vo?

  One of us, as we say. Okay, so first lightning round question. This is hyper, hyper, hyper personalized software. Is this a product? Or do you think that just every CPO needs to go out there and build their, you know, as I say, artisanal farm to table chief of staff for your app? You know, where, where do you fall on this like personal software versus small market SaaS? For, for something like this?

• 39:04Speaker 01

  I think that parts of this are probably a product. Like I'd imagine that, you know, maybe Anthropic tries to build this themselves. Right? Where it's like everybody's chief of staff, not just for a product leader. That may not kind of get it, everything that people want. And so you may end up having kind of extensions off of that. Or, right, but I think there's going to be a whole ecosystem around how to actually like, kind of get work done and what people are doing with MCPs is just the beginning. It's still like. Let me tell you, like, the very early days of being able to access company data. But I do think that this is an app. I just don't know if it's going to be exactly this form factor.

• 39:47Claire Vo?

  Yeah. And then my second question for you, which is a little bit more on the people's side, which is you clearly care about AI fluency. How are you hiring for that? How is your team reacting to it? How are you evaluating and promoting? Kind of what's your framework for talent around this?

• 40:06Speaker 01

  Yeah, I actually tried to share a little bit of that in this, in this app so that you can kind of see that. But I think that AI is almost like you have to look at each of the different dimensions of your team, whether it's data and insights, whether it's tool fluency, you know, like builder culture, career ladder, interviewing, like you have to look at every single aspect of how you, you know, your operating system for your team and kind of like grade yourself and be like, how far have we moved down the spectrum? And, you know, in our case, like, we're in the middle of redoing our career ladder. Because I wanted to be really clear to people that it's not just fluency. It's like, I expect people to like lead and own and understand what is possible

• 40:50Speaker 01

  and push the limits of our product. And, you know, it's not just for themselves, it's for our customers.

• 40:58Speaker 01

  And then I think you have to kind of like reinvent so many different parts of your, your practice as a leader.

• 41:04Speaker 01

  And so that's, that's the skill that you kind of need to lead into as a leader is just like reinvention at all times.

• 41:10Claire Vo?

  Okay. And then my final question for you, I ask everybody, you have dual link clods open too, so this is an interesting question. But when you are prompting and he's just not listening, he's just not giving you what you want, or your chief of staff is too me, this is really funny because usually I see so many AI agents be too nice, but yours is actually really mean. What is your prompting technique? Are you an all, your, your AI is an all caps AI. So I'm curious if you go, you hit hard right back at it. What's your prompting technique?

• 41:45Speaker 01

  My prompting technique is first, when I don't like what it's giving me, I will clear Claude code. So a lot of times I'll like clear it and then I'll try again. And if I'm still not getting what I want, I'll be like, be 100x more this thing that I want. Or, you know, be 10x. And so it's like, I almost use like 10x as like a little bit more and 100x as like, go and just like rip it apart and do something else.

• 42:12Claire Vo?

  So this is a repeated tip. We heard this from Hillary at Whoop in one of our early How I AI episodes, which is these models like numbers. So say be like 20%, you know, nicer, or be 100x more harsh, or make this three times as purple, whatever it is. You can quantify it. It can calibrate how it's working for you. So great, great tip. Well, Rachel, thank you for joining us on How I AI. How can we find you and how can we be helpful to you?

• 42:40Speaker 01

  Yeah. Thanks again, Clara. This is amazing. I'm at Rachel Wolan on Twitter, and you can also find me on LinkedIn to follow me. And I also recommend checking out webflow.com. We have a brand new app gen product that we just released last week. It's really for your marketing team to be able to do vibe marketing, which is a whole new wave that we're riding. So amazing to be here.

• 43:10Claire Vo?

  Awesome. Thanks. And I appreciate you sharing all your tips on How I AI.

• 43:16Claire Vo?

  Thanks so much for watching. If you enjoyed the show, please like and subscribe here on YouTube, or even better, leave us a comment with your thoughts. You can also find this podcast on Apple Podcasts, Spotify, or your favorite podcast app. Please consider leaving us a rating and review, which will help others find the show. You can see all our episodes and learn more about the show at HowIAIPod.com. See you next time.