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

1. 0:00 – 2:26

   Introduction to Rachel Wolan

   1. CVClaire Vo0:00

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

   2. RWRachel Wolan0:03

      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.

   3. CVClaire Vo0:18

      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.

   4. RWRachel Wolan0:25

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

   5. CVClaire Vo0:29

      Mm.

   6. RWRachel Wolan0:29

      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."

   7. CVClaire Vo0:43

      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.

2. 2:26 – 6:26

   Why Rachel started leaning into AI

   1. CVClaire Vo2:27

      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"?

   2. RWRachel Wolan3:31

      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, I feel like I, I kind of built that resiliency pretty early in life. And now, uh, in my, my current role, you know, I probably, uh, hadn't coded in about, you know, six or seven years, and then when all of the new AppGen tools came out, I think Lovable is, like, one year old now, um, I was like, "Hey, I'm gonna 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, uh, but, you know, when it was s- when kind of like vibe coding started coming in the scene, I actually built an app, uh, 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 it. I'm running it on localhost, and, you know, I, I probably have built dozens of apps this year. We just launched our AppGen 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. 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.

   3. CVClaire Vo5:09

      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, [chuckles] I didn't have time to do things. And so the ability to, you know, do AI assistant 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. 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 [chuckles] 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 gonna be the same.

3. 6:26 – 8:17

   Building an AI chief of staff

   1. CVClaire Vo6:27

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

   2. RWRachel Wolan6:40

      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 it 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, uh, 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, I really want to help my team level up, and so it, 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.

   3. CVClaire Vo7:22

      I completely agree. And one of the things I wanna 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, a multimodal interface to this, in which it can be a web app, or it could 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, [chuckles] and you may wanna do it completely differently the next time. You can build these, like, little 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

4. 8:17 – 10:00

   Prepping for the podcast

   1. CVClaire Vo8:17

      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.

   2. RWRachel Wolan8:24

      I did. So I will actually run different terminals that are all running Claude. I do this partially because, you know, I, I th- I wanna make sure that I'm, like, not using too much context, and then I find that w- when I, when I'm asking questions that are of a similar ilk-

   3. CVClaire Vo8:41

      Yeah

   4. RWRachel Wolan8:41

      ... I get better answers back, um, in that same terminal window. But I basically prompted it and said, "Hey, let's generate, um, 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. You know, if we were to vamp, it would be like: Hey, here are three different ways you could tell m- tell me about yourself and, uh, Webflow.

   5. CVClaire Vo9:15

      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, I say sometimes to people, the number one skill you need to learn as an executive is improv, [chuckles] because you are just-

   6. RWRachel Wolan9:44

      That's right

   7. CVClaire Vo9:44

      ... dropped into a wide variety of contexts. You need to be able to think on your toes. And so just the abil- 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. So let's go through-

   8. RWRachel Wolan9:59

      All right.

   9. CVClaire Vo9:59

      Okay, this is a very specific

5. 10:00 – 14:14

   Rachel’s morning flow with her AI chief of staff

   1. CVClaire Vo10:00

      example. It's sort of our meta example-

   2. RWRachel Wolan10:02

      Yeah

   3. CVClaire Vo10:02

      ... on how we're gonna 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.

   4. RWRachel Wolan10:11

      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, I think that I, I don't have a chief of staff anymore. I used to have a chief of staff at a- 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? Um, "and you're, you're not, like, kind of taking care of yourself." And so, you know, uh, the other- the, the main thing that they kind of called, called me out on, which I thought was really funny, um... So we just had our conf- 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, 100% correct, and so I think that... But it, 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." Um, it's very, like-

   5. CVClaire Vo11:20

      [chuckles]

   6. RWRachel Wolan11:20

      ... dramatic, right? [chuckles] Uh-

   7. CVClaire Vo11:22

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

   8. RWRachel Wolan11:26

      Good question. Um, so I went and I got a token from Google Cloud, and I basically... I, I'm not gonna show it, but I, I basically have it, like, in my, uh, dotenv 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 gonna need to construct it because I'd built other apps before. But let's see if I can find it. So this is, like, my dotenv file. I'm not gonna show it to you, 'cause 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. Um, and then it walks you through how to actually go and set that up. One of those variables is my, uh, Google Calendar.... and you know, then I, I give it certain authorizations. 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, uh, 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? Um, it's kind of janky software, right? Because I, [chuckles] I mean, I, 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, um, when I realize I've given it, like, too much, uh, 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, um, and what feels like it's kind of, like, overstepping.

   9. CVClaire Vo13:08

      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.

   10. RWRachel Wolan13:23

       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. Uh, this is what I think you can actually... You can do something else. This is, y- you know, I think the s- the th- the way that I would like to make this smarter is, this is who you should delegate to. And then, you know, I'm, I'm still kind of working on my, my Slack agent, so I, 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?"

   11. CVClaire Vo13:57

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

   12. RWRachel Wolan14:03

       This is fetching it through an API token.

   13. CVClaire Vo14:06

       Okay. Got it.

   14. RWRachel Wolan14:06

       Um, I don't think that there's an MCP that is, like, a, uh-

   15. CVClaire Vo14:11

       Official

   16. RWRachel Wolan14:12

       ... official MCP, but

6. 14:14 – 16:34

   Designing a personalized interface with custom note cards

   1. RWRachel Wolan14:14

      what you kind of see... Th- 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, uh, uh, you know, like, a little, like, note card that I like to make, uh, for myself, and, like, I did prep for you.

   2. CVClaire Vo14:28

      Mm-hmm.

   3. RWRachel Wolan14:28

      That's good. And then, you know, I'm basically kind of looking at this. It- 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, um, to be like.

   4. CVClaire Vo14:44

      Let's just take a pause really quickly on your web app-

   5. RWRachel Wolan14:47

      Yeah

   6. CVClaire Vo14:47

      ... 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 a l- uh, can you show us that little note card really quickly?

   7. RWRachel Wolan15:08

      I, I got this idea from Marc Andreessen about, like, d- what are my top priorities for the day, and then did I actually accomplish it?

   8. CVClaire Vo15:19

      H- and hold your horses real quick. It's also extremely cute. So for people that are o- 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, I mean, this is one of those other things-

   9. RWRachel Wolan15:36

      Mm

   10. CVClaire Vo15:36

       ... 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 you have your top priorities.

   11. RWRachel Wolan15:51

       Yeah, I, I, just as a side note, like, I almost redesigned the app last night 'cause I was like: Oh, I wish it kind of felt more like Apple Notes.

   12. CVClaire Vo15:58

       Yeah.

   13. RWRachel Wolan15:58

       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, uh, there's something really fun about, like, actually getting to design again, but not actually... I mean, it takes... The, the amount of time, it's not, it's, it's not at, like, the pixel-level perfection of the incredible designers on my team, but it does at least convey, like, a, you know, there, there's a certain, um, je ne sais quoi of this, like, app that I'm trying to, to capture to make myself happy.

   14. CVClaire Vo16:32

       Yeah, I love it. It's so

7. 16:34 – 19:34

   Getting “brutal truth” feedback from your AI assistant

   1. CVClaire Vo16:34

      great. Um, okay, so-

   2. RWRachel Wolan16:36

      So here we go. Here we go.

   3. CVClaire Vo16:37

      Yep. [chuckles] Your, your chief of staff is very mean.

   4. RWRachel Wolan16:42

      [chuckles] I tell her to be mean to me, that's why. I want it to, like, keep me in line, you know? I'm, I'm one of those people-

   5. CVClaire Vo16:50

      Oh, right

   6. RWRachel Wolan16:50

      ... who likes to try to take on too much, I think, sometimes. Um, 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. Um, it's telling me there's too much clutter on my calendar. This is one of those things where somebody's just, like, put something in my calendar, I don't know this person. Um, 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 [chuckles] , 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?

   7. CVClaire Vo17:38

      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?" [laughing]

   8. RWRachel Wolan17:51

      Right. [chuckles]

   9. CVClaire Vo17:51

      So even giving that draft where you could just, "Fine, I can 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, w- just too busy, overbooked, under-prepped, really just wanting to spend her time vibe coding, [chuckles] if we're being honest. So I think this is really-... really useful, and again, I, I like this 'cause 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.

   10. RWRachel Wolan18:30

       The brutal truth is that- [laughing] I'm like, yep. [laughing]

   11. CVClaire Vo18:37

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

   12. RWRachel Wolan18:39

       I know, it-

   13. CVClaire Vo18:40

       [laughing]

   14. RWRachel Wolan18:40

       I'm like, "Is that bad? Is that a bad thing?" Um, [laughing]

   15. CVClaire Vo18:45

       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. [laughing]

   16. RWRachel Wolan18:57

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

   17. CVClaire Vo19:00

       This is the behind-the-curtain stuff, and I tell everybody this about the origin story of ChatPRD, which is they're like, "Why did you build ChatPRD?" And I was like, "Man, 'cause no matter how fancy of a title I got, I still was writing PRDs all the time." [chuckles]

   18. RWRachel Wolan19:13

       Right.

   19. CVClaire Vo19:13

       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.

   20. RWRachel Wolan19:22

       Yeah.

   21. CVClaire Vo19:22

       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.

   22. RWRachel Wolan19:31

       [chuckles]

   23. CVClaire Vo19:31

       Um, and, and build this for yourself.

8. 19:34 – 23:31

   Email triage and management workflows

   1. CVClaire Vo19:34

      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.

   2. RWRachel Wolan19:41

      Correct.

   3. CVClaire Vo19:41

      What is outstanding? Can you just walk us through maybe just some of the problems that your email, um, chief of staff solves?

   4. RWRachel Wolan19:48

      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, um, to... Uh, 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. Um, 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." 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?

   5. CVClaire Vo20:39

      Mm.

   6. RWRachel Wolan20:40

      And so, you know, this is like kind of a cursor review, and then I can go through my inbox, like, very, very quickly. Um, um, I, I think the Slack version of this is gonna be, like, an absolute game-changer since we operate [chuckles] almost internally in Slack 100%, um, 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.

   7. CVClaire Vo21:02

      Yeah.

   8. RWRachel Wolan21:03

      Um, so I, I feel like that's, like, my next... That's my next hill to climb.

   9. CVClaire Vo21:07

      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-

   10. RWRachel Wolan21:31

       [chuckles]

   11. CVClaire Vo21:31

       ... are expected to be able to do this, and I just think that is such an indictment of [chuckles] how we're expected to navigate the massive amounts of information as, as people that are working on teams in these asynchronous or semi-asynchronous ways.

   12. RWRachel Wolan21:46

       Yeah, it... 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, I think that that ha- 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, our brains, um, in through that kind of transition. So I s- I still think we're in, like, the early days of, of how to effectively do remote work, but that's, like, a different topic for another podcast.

   13. CVClaire Vo22:22

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9. 23:31 – 28:18

   Prepping for networking dinners and events

   1. CVClaire Vo23:32

      Okay, I want to do one more fun chief of staff example-

   2. RWRachel Wolan23:36

      Okay

   3. CVClaire Vo23:36

      ... before we go on to our next workflow, which is, how do you prep for dinners? Tell me about... This, this little tab-

   4. RWRachel Wolan23:42

      Sure

   5. CVClaire Vo23:42

      ... is calling my name. I must know.

   6. RWRachel Wolan23:44

      Okay. All right. So I'm going to a dinner tonight. Um, 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, I'll show you. Uh, 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, it read each of them, and it... I, I haven't looked at this yet, so I can't tell you if this is good or not. Um, buyer, buyer beware. Uh, it's free, so... Um, and then it-... went and did search on every single person on that 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, th- like, he was acquired. So it looks like they're, like, actually identifying the right person. So it, 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 pretty good. It... And it, it also has, like, con- the, 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 from, like, some communication workshops 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, a... I try to generate this maybe once a month of, like, what are the new Webflow products, um, off of our release notes, so that it kind of, like, knows everything that we've released in the last couple of years. Um, and so then it kind of knows a lot about me, and then it's telling me about the venue, uh, and then it's like, what are hot discussion topics? Um, and, you know, I'm going to, like, an AI marketer, kind of AEO, answer engine optimization, uh, dinner. And, you know, then it's, like, created this full prep doc. So I'm like, "Okay, that's great." And then 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. Um, 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, uh, like conversation starters. Um, you know, and like, th- this is, like, kind of the introvert in me or maybe the ambivert trying to, like, uh, be prepped. Um, [chuckles] just-

   7. CVClaire Vo26:33

      I love this-

   8. RWRachel Wolan26:35

      And then-

   9. CVClaire Vo26:35

      ... because I am an introvert. I get invited to these dinners all the time. Um, and this is, this is really great. One of the things I want to call out for How I AI, um, 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 into 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, um, app for, you know, your own research or context, 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, um, 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, um, agentic tools a lot better.

   10. RWRachel Wolan28:02

       Yeah. I, I feel like it's been a game changer to start using Markdown files, um, and then also start using Markdown for even, like, PRDs. So-

   11. CVClaire Vo28:11

       Yep

   12. RWRachel Wolan28:11

       ... 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.

10. 28:18 – 30:09

    The result of building an AI chief of staff

    1. CVClaire Vo28:18

       I love it. And so what do you think the result of you building this chief of staff has been? Um, 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?

    2. RWRachel Wolan28:32

       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, um, as part of this app, and there's certain types of, um... It, it's gotten me very close to our code base as well. Um, so for example, I, you know, I have, like... I, I use Code Ex a lot. Right now, I'm only using it on this particular app, but I could, like, go and, and be like, "Tell me about, uh, this app. How is it built?" And I think that that's really important to be able... Uh, so I also obviously have access to our rep- 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, um, 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, I think that this is, like, very accessible to anybody.

    3. CVClaire Vo29:56

       This is awesome. And again, you can just add modules, you can spin up new Claude Code interfaces, and then you can design whatever you want on the front end. It can look however-

    4. RWRachel Wolan30:08

       Exactly

    5. CVClaire Vo30:08

       ... however you want,

11. 30:09 – 35:38

    Organizing “builder days” to drive AI adoption

    1. CVClaire Vo30:09

       which I love. Well, I wanna flip this to another use case in the second half of our episode-

    2. RWRachel Wolan30:15

       Okay

    3. CVClaire Vo30:15

       ... which is a little bit less about how you-... personally use AI, even though we've, we've shown that a little bit, I do wanna talk about how you get AI into your team. And so I wanna talk-

    4. RWRachel Wolan30:24

       Yeah

    5. CVClaire Vo30:24

       ... 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, I do as well, which is like, we're gonna do the work, we're gonna get into it. 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 I 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.

    6. RWRachel Wolan31:03

       Yeah. So we did a builder day last Wednesday. Um, 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, 'cause I think that it's actually helpful to see that. So this is a screenshot from Hex that was a dashboard, um, 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 you... What, what I think is really cool is, like, very few people were using it before that.

    7. CVClaire Vo31:38

       Yeah.

    8. RWRachel Wolan31:38

       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, and I'll talk about a little bit about how we actually ran that builder day. But we had design, product, uh, data science, user research, analytics, engineering, you know, lots of different functions, um, 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. Um, but, you know, this is like... I, I'm excited to see, like, does this continue to be sustained? Um, is this something that people start to use as part of their day-to-day? And, you know, I, I really think about, um, an organization kind of similar to any normal distribution curve, um, where you're gonna have, you know, it- it's the innovator's dilemma, where you have, 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, um, 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, um, uh, that are... By just trying to reduce the friction and then trying to lean into the people who are really embracing that technology. Um, and, and s- I think it needs to be both, you know, a top-down mandate. Like, I tell 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.

    9. CVClaire Vo33:26

       So this is the outcome you're trying to drive-

    10. RWRachel Wolan33:28

        Right

    11. CVClaire Vo33:28

        ... which is, like, we wanna use these tools. We wanna 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.

    12. RWRachel Wolan33:42

        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. Um, and the goal was really to boost confidence, um, spark adoption. And so we had a couple of different types of tools. Um, we lit up Cursor, Figma, Make, and Webflow, um, 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 f- we had different assignments for product. We had... You know, you can explore a new product idea, um, you can validate user interactions, you can test product concepts, you can build a full end-to-end workflow. You know, we d- so we, we also had them do, like, a, a warm-up assignment. A- 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-

    13. CVClaire Vo34:39

        Mm

    14. RWRachel Wolan34:39

        ... different categories. Um, and then we, 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, we, we definitely aren't, like, we've, we've nailed every single part of this, but I was really encouraged to see so many people actually, like, taking one step outside of their comfort zone.

    15. CVClaire Vo35:00

        Amazing. And so this is something that for the leaders 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. Um, 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,

12. 35:38 – 38:00

    Measuring the impact of AI adoption initiatives

    1. CVClaire Vo35:38

       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 from the team before and after these builder days?

    2. RWRachel Wolan35:49

       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. Um, 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.

    3. CVClaire Vo36:09

       Yeah.

    4. RWRachel Wolan36:10

       And that, to me, was, like, the most heartwarming thing I could possibly imagine, um, is all of these people... I, I call it getting blue-pilled, right?

    5. CVClaire Vo36:19

       Mm-hmm.

    6. RWRachel Wolan36:19

       Like, all these people all of a sudden, like, stepped into an, a new part of their professional journey, and that, that just made me really happy.

    7. CVClaire Vo36:28

       ... So to recap this for any of the CPOs or executives or aspiring CPOs or executives out there, you know, a couple takeaways from this episode is, one, there is just no substitute for getting your hands-on to these tools, especially coding things. I think it's 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 gonna become more table stakes is at least being able to use code to get things done, even if you can't be an exceptional [chuckles] software engineer. That you can build yourself custom software, especially Markdown-based, um, that has both sort of agentic access properties where Claude Code could use it, and web UI. You could run it locally if you don't wanna deploy anything. It's not a big deal. And it also helps you kind of bypass some of the, um, 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, um, 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 gonna share-

    8. RWRachel Wolan37:43

       Yeah

    9. CVClaire Vo37:43

       ... this repo and this resource with us, so you can look at it. There's a repeatable process for onboarding, educating, engaging, and driving sustained adoption of AI in your org through, um, these sort of spikes in builder days, and then you're just having

13. 38:00 – 43:43

    Lightning round and final thoughts

    1. CVClaire Vo38:00

       fun. Are you having fun? 'Cause I am having so much fun right now.

    2. RWRachel Wolan38:03

       Yeah.

    3. CVClaire Vo38:03

       And that's one of, 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.

    4. RWRachel Wolan38:10

       I think it's the most amazing time to ever be doing this job in the entire time that I've been doing it. Um, 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.

    5. CVClaire Vo38:26

       I completely agree. Okay, let's do some lightning round questions-

    6. RWRachel Wolan38:29

       All right

    7. CVClaire Vo38:29

       ... and then let's get you back to, um, I just have to call it out, your two Cursor windows, [chuckles] down, down at the bottom. 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?

    8. RWRachel Wolan39:04

       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?

    9. CVClaire Vo39:13

       Yeah.

    10. RWRachel Wolan39:13

        Where it's, like, everybody's chief of staff, not just for a product leader. Um, 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 gonna 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. Um, but I do think that this is an app. I just don't know if it's gonna be exactly this form factor.

    11. CVClaire Vo39:47

        Yeah. And then my second question for you, which is a little bit more on the people 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?

    12. RWRachel Wolan40:06

        Yeah, I, I actually tried to share a little bit of that in this, um, 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, um, down this spectrum? And, you know, in our case, like, we're in the middle of redoing our career ladder, uh, because I want it 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 and push the limits of our product. Um, and, you know, it's not just for themselves, it's for our customers. Um, and then I think you have to kind of, like, reinvent so many different parts of your, your practice as a leader. Um, and so that's, that's the skill that you kind of need to lean into as a leader, is just, like, reinvention at all times.

    13. CVClaire Vo41:10

        Okay, and then my final question for you. I ask everybody. You have dueling Claudes 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 [chuckles] is actually really mean. What is your prompting technique? Are you in all cap... Your, your AI is in all caps AI, so I'm curious if you go... You hit hard right back at it. What's your prompting technique?

    14. RWRachel Wolan41:45

        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.

    15. CVClaire Vo42:12

        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, um, 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?

    16. RWRachel Wolan42:40

        Yeah. Uh, thanks again, Claire. This was amazing. Um, I'm @rachelwolan on Twitter, and you can also find me on LinkedIn to follow me. Um, and I also recommend checking out, uh, webflow.com. We have a brand-new AppGen product that we just released last week. Uh, 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.

    17. CVClaire Vo43:10

        Awesome. Thanks, and I appreciate you sharing all your tips on How I AI. [upbeat music] 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. [upbeat music]

Episode duration: 43:43