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

[00:00] So you've built yourself an AI chief of staff. - The AI chief of staff is actually something that I have been trying to build since I started VibeCoding. 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. - Let's go into a specific workflow of how this chief of staff actually helps you with do something. I think you did a little prep for this podcast. - I basically prompted it and said, hey, let's generate a Howie AI flow. [00:30] to get it to tell me what should I actually demo that is going to be part of this chief of staff app. And then what actually ends up getting output is this. It gives me an executive summary. Here are three different ways you could tell me about yourself and Webflow. Just the ability to be prepped even in a few minutes ahead of these things can really make your life better. [00:52] Welcome back to How I AI. I'm Claire Vo, product leader and AI obsessive here on a mission to help [01:00] Today's episode is all about the AI Native Executive. [01:04] We have Rachel Wolin, CPO at Webflow, who's going to show us how she uses AI, cloud code and personal software to run her life. [01:15] 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. [01:28] Let's get to it. [01:30] 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,

[02:00] 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. [02:27] 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. [02:38] And we were talking about how so much of the discourse is around [02:42] The AI Native PM, the AI Native Engineer, basically like the AI Native IC. And we've spent a lot of time on that topic here at How I AI. [02:52] 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... [03:20] 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, [03:28] My job's going to change. I really got to figure this stuff out.

[03:31] I started coding when I was 16. [03:33] And, you know, it's obviously been kind of a lifelong journey of building and tinkering and... [03:39] you know, making mistakes. And so I feel like I kind of [03:43] built that resiliency pretty early in life. And now in my current role, [03:50] You know, I probably 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. I was like, hey, I'm going to try this out. And, you know, it felt magical, right? And I'd kind of played around with some of the earlier versions of GPT, right? [04:08] But when kind of like vibe coding started coming in the scene, I actually built an app [04:15] uh to capture my kids memories and that was the first vibe coded app that i built [04:20] And I built it in a weekend. And it just felt like something completely different than anything I'd ever built before. [04:26] And, you know, here we are a year later and this is, you know, now I'm like sitting in cloud code all day. And I, you know, this is an app that I kind of like I'm continually maintaining, you can see that I'm running it on localhost. [04:39] And 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, [04:49] 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 really, you know, kind of how I got started. And I think it's something that now is just part of my day-to-day. This is my daily driver.

[05:09] 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... [05:15] you know, started coding very early, a lot of self-taught stuff, and then, you know, get into these jobs where coding... [05:22] Hands on keyboard wasn't my job. [05:25] And [05:26] 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. I didn't have time to do things. And so the ability to... [05:41] 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 a lot the second thing i hear a lot [05:54] who are like trying to motivate themselves to learn some AI skills is find something [06:00] personal to work on. You said like this memory app for your kids. [06:04] 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 [06:22] think that your day-to-day job is going to be [06:25] The same. [06:26] So let's get into what you built, because I feel like I need this. [06:31] So you've built yourself an AI chief engineer. [06:35] of staff. [06:36] Tell us more and how you're using it in your everyday life.

[06:40] Yeah, so the AI chief of staff is actually something that [06:44] I have been trying to build since I started Vibe Cutting. So this is actually the first app that I tried and then didn't work. [06:52] the first time that I tried it. And then I've just been kind of continually trying to build it. [06:56] And what you'll see here is kind of rotating agents. I've just kind of been ticking away different use cases. And then a big part of this is also... [07:07] You know, I really want to... [07:10] help my team level up. [07:12] And so it would be inauthentic for me to... [07:17] tell them, hey, you need to prototype with AI if this isn't something that I'm doing every single day. [07:22] I completely agree. And one of the things I want to call out about how you're talking about building this software is, [07:27] is one, you're building it for an N of one. You're building it for yourself. So it can be really hyper-customized. [07:34] Two, you're building sort of a multimodal interface to this in which it can be a web app or it could be something just like a little bit more... [07:42] close to the metal in terms of in the terminal or in cursor. And then I love this idea of being able to [07:50] build ephemeral widgets, [07:51] that are useful that you can just toss away like [07:54] You may never look at this Q4 roadmap after Q4 again, and you may want to do it completely differently. [08:01] 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

[08:12] 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. I did. So... [08:25] I will actually run different terminals that are all running Claude. [08:29] I do this partially because, you know, I want to make sure that I'm like... [08:34] not [08:34] using too much context. And then I find that [08:38] 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 and said, hey, let's generate a HowA.AI platform. [08:50] flow. And so I was trying to get it to tell me, like, what should I actually [08:54] demo that is going to be part of this Chief of Staff app. So it knows this structure. [08:59] And then what actually ends up getting output is this. [09:03] 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 me about yourself and Webflow. [09:14] 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 tell 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.

[09:44] into a wide variety of contexts. You need to be able to think on your toes. And so just the ability, I had a chief of staff, and just the ability to be prepped even in a few minutes ahead of these things can really... [09:56] make your life better so let's go through okay this is a very specific example it's sort of our meta example [10:02] on how we're going to go through this show. But let's talk about your morning triage and how you start... [10:07] your day every day using this AI chief of staff. [10:11] That sounds good. [10:12] In this case, what I actually gave it was a question. I said, hey, how can I make my last week better? What could I have done? [10:22] 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... [10:29] they would be like kind of coming through my calendar and like, hey, you're not blocking your energy. [10:33] And you're not taking care of yourself. [10:36] And so, you know, [10:38] The main thing that they called me out on, which I thought was really funny, so we just had our customer conference about a month and a half ago. [10:47] And, you know, I haven't. [10:49] 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. [10:55] And that's where you get energy from. [10:57] And so it's basically like doing a time analysis on my external calls. I'm like, how is that possible? [11:03] And again, it did pick up, it wasn't like 100% correct. [11:06] And so I think that, 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. [11:13] Right. And it's like you're a CPO with like no regular visible cuts for contact. Fatal flaw. And I'm like, oh, gosh, it's very like dramatic. Right. Well, how does this actually access your calendar? How have you technically built this? Good question.

[11:27] So I... [11:29] went and I got a token from Google Cloud. And I basically, I'm not going to show it, but I basically have it like in my .env file. [11:41] 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'd built other apps before. But let's see if I can find it. So this is like my .emv file. I'm not going to show it to you because I'll have to like burn all the tokens I have in there. But it's basically has a bunch of variables. [11:59] And so one of those variables is my Gmail. And then it walks you through how to actually go and set that up. [12:05] One of those variables is my Google Calendar. [12:08] And [12:10] then I give it certain authorizations. So in the case of Google Calendar, it can only read my calendar. [12:15] In the case with Gmail, it can only create drafts. It can read, it can archive, and it can create drafts and label. [12:22] And so a lot of this is like, [12:25] thinking about how do I, you know, put the right guardrails in place? [12:30] 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? [12:36] And it's kind of janky software, right? Because I mean, 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. [12:47] when I realized I've given it too much [12:50] you know, too much authority to act on my behalf. And so I think that's, you know, part of it is also like, [12:56] Thank you.

[12:57] me populating my own, you know, kind of intuition about what feels good in working with agents. [13:04] and what feels like it's kind of like overstepping. [13:08] 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. So tell me about my day tomorrow. What can I delegate? [13:27] Thank you. [13:28] 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 and [13:35] Uh, this is what I think you can actually, you can do something else. This is, you know, I think the, the, the way that I would like to make this smarter is this is who you should delegate to. [13:45] 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, you know, [13:55] could we go do this? [13:57] And is this fetching the calendar events through an MCP? Is it some custom code that you wrote? This is fetching it through an API token. [14:06] I don't think that there's an MCP that is like a... [14:11] Official. Official MCP. But what you kind of see, this is why sometimes I like looking at my briefing, because I [14:18] So other things that I do hear... [14:20] You know, I actually have like a little... [14:23] you know like a little like [14:25] note card that I like to make for myself. I'm like, I did prep for you. That's good.

[14:29] And then, you know, I'm basically... [14:33] kind of looking at this, the thing that I like about it is it makes it just very easy for me to get a snapshot and view it. But I'm still kind of like iterating on what do I want this... [14:42] to be like. - Let's just take a pause really quickly on your web app while this is running in the background. [14:49] And what I love about what you've designed is... [14:53] look, we're all running on Google Calendar or whatever. [14:57] But... [14:58] You want... [15:00] it to look a certain way. [15:02] You want it to be designed a specific way. You want to have a, can you show us that little note card really quickly? Yeah. [15:08] I got this idea from Marc Andreessen. [15:11] about like, [15:13] What are my top priorities for the day? [15:15] And then... [15:16] did I actually accomplish it? [15:18] 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 and 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, [15:48] So your top priorities, [15:50] Yeah, just as a side note, I almost redesigned the app last night because I was like, oh, I wish it kind of felt more like Apple Notes. [15:58] 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?

[16:05] And I had like a theme for it. [16:06] And so there's something really fun about like actually getting to design again. [16:11] but not actually, I mean, it takes the amount of time. It's not at like the pixel level perfection of the incredible designers on my team, but it does at least convey... [16:21] Like, [16:22] You know, there's a certain... [16:25] je ne sais quoi of this app that I'm trying to capture to... [16:30] make myself happy. [16:32] Yeah. [16:32] I love it. It's so great. Okay, so here we go. Here we go. Yep. [16:37] Thank you. [16:38] Your chief of staff is very mean. I tell it to be mean to me. That's why. [16:46] I wanted to keep me in line. I'm one of those people who likes to try to take on too much, I think, sometimes. [16:53] Okay, so it's basically telling me to make certain meetings async. That's a great idea. [16:58] 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... [17:05] Good call. It's telling me there's too much clutter on my calendar. [17:10] This is one of those things where somebody's just like, put something in my calendar, I don't know this person. So that's definitely optional and I haven't accepted. [17:18] And then it's like, can whatever director cover this and send me a summary? Can, right? And... [17:24] This is really helpful. This is like forcing me to think about, 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? [17:33] to do some work and maybe get home to my family at a reasonable hour.

[17:37] I love these delegation messages because just as a human, it is very easy to identify meanings that [17:45] 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 the space? 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 [18:02] AI native exec, just too busy, overbooked, underprepped, really just wanting to spend our time vibe coding, if we're being honest. So I think this is really... [18:13] really useful and again i like this because it's very conversational as a chief of staff might be [18:21] 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. The brutal truth is that I'm like, yep. [18:36] It's kind of being a senior PM sometimes sounds more fun. I know. I'm like, is that bad? Is that a bad thing? [18:45] 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. [18:56] Yeah. [18:57] I mean, they're calling a spade a spade. 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.

[19:08] Because no matter how fancy of a title I got, I still was writing PRDs all the time. And so this is really, really great. And then I love this idea of like the only thing that will matter in six months is... [19:20] are is this conversation what an amazing way to level up so chiefs of staff [19:25] that are watching here, you need to end every meeting with your exec with [19:29] the brutal truth. Um, [19:32] 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 process [19:40] for email as well. What is outstanding? Can you just walk us through maybe just some of the problems that your email chief of staff solves? Yeah, I mean, I think that my biggest problem is that I'm, [19:52] I'm like 500 emails deep in my email. But it's basically archiving a bunch of stuff that I don't need. [19:59] It's keeping a few things in the inbox and then it's drafting a few responses. [20:05] And, you know, a lot of this is like I've been kind of like continually updating this particular agent. [20:11] to know where to draft responses. [20:14] And sometimes Duras' responses, you know, like some random SDR inbounds to me. And I'm like, no, no, no. [20:20] You don't need to draft responses to this person. But a lot of times it'll be like, [20:25] somebody from 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 trying to also know when somebody is waiting on me and asking for some document to get shared. And so this is kind of a cursory view, and then I can go through my inbox very, very quickly.

[20:46] 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 where the models are at, it's like almost too much data to triage. So I feel like that's like my next hill to climb. [21:07] 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 information? [21:19] disconnected context, so disconnected that fancy pants, large language models, cannot make sense of it. But for some reason, [21:28] 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 people that are working on teams in these asynchronous or semi-asynchronous ways. [21:46] Yeah, I mean, I think it's also... [21:48] become so different during, you know, like post-pandemic, and especially if you're working for a remote organization. [21:56] And, you know, I think that [21:58] That, you know, we're obviously only, what, you know... [22:02] four years, five years into that experiment. And so I think that we haven't like the tools haven't quite caught up. [22:08] 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...

[22:18] effectively do remote work. But that's like a different topic for another podcast. [22:22] The early story of Atlassian is probably very similar to your own. Atlassian knows firsthand the challenges that startups face every day and that the right tools are essential to go from MVP [22:34] to IPO. That's why Atlassian for Startups gives eligible companies up to 50 seats free on the Premium Edition for products like Jira, Confluence, Loom, Jira Product Discovery, Compass, and Bitbucket. So your team can use the best-in-class tools to plan, track, and collaborate on work, whatever that work might be. Many of today's most successful startups like Cloudflare, Canva, and Rivian [23:00] relied on Atlassian for their growth trajectory, and Atlassian wants to give that same opportunity 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 [23:30] eligibility. [23:31] Okay, I want to do one more fun chief of staff example before we go on to our next workflow, which is... [23:39] how do you prep for dinners? Tell me about just this little tab is calling my name. I must know. All right. So I'm going to dinner tonight. It is called the CXO Collective. And what I did was I took a screenshot

[23:55] of this guest list. [23:57] And so, you know, I'll show you it's, you know, I basically literally just took a screenshot of this guest list. [24:04] And then I dropped it in here. So you can see the image that I dropped in here. [24:09] And then it [24:09] read each of them and I haven't looked at this yet so I can't tell you if this is good or not. [24:15] Buyer beware. It's free. And then it [24:19] went and did search on every single person on that list. [24:24] And then I have an agent that is basically kind of like going and... [24:28] like doing more analysis on like this happens to be one of my colleagues who's going to the dinner guy leaf. [24:34] And so, you know, like he was acquired. So, yeah. [24:37] It looks like they're actually identifying the right person. So what it does is it goes and it does a search on the web [24:44] Then it is a search in LinkedIn. [24:45] Then it goes and tries to do more web search. And it's like, hey, this is your colleague. [24:51] 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. [24:58] So let me see if I can just show you a couple of examples. [25:02] Yeah, so I have like... [25:04] some general about me documents like [25:06] This is from some communication workshop that I went to, where this is how I want to communicate. [25:13] 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, [25:23] I try to generate this maybe once a month of like, what are the new Webflow products?

[25:27] off of our release notes so that it kind of like knows everything that we've released in the last couple of years. [25:33] And so then it kind of knows a lot about me. [25:35] And then it's telling me about the venue. And then it's like, what are hot discussion topics? [25:40] And, you know, I'm going to like an AI marketer, kind of AEO, answer engine optimization. [25:46] dinner and [25:48] 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 everything that's in dinner research is actually a markdown file. [26:01] So that's the other way that this has worked really well. I could go and open this up in Cursor if I could find that file. But really, I just find it easier for something like this to go into my chief of staff. [26:13] And then let's see. [26:15] Pretty up. It's gonna be a nice dinner and you know, it's like these are my priority connections and [26:21] like conversation starters, like, [26:24] You know, and like, [26:26] this is like kind of the introvert in me or maybe the ambivert trying to like [26:29] be prepped. [26:31] Um, just, I love this 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.

[27:01] file store. [27:03] 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 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. [27:24] 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 Cloud Code and say something like, [27:38] 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. [27:53] 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. [28:02] Yeah, I feel like it's been a game changer to start using Markdown files. [28:06] And then also start using Markdown or even like PRDs. [28:10] 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. [28:18] I love it. And so what do you think the result of you building this chief of staff has been? [28:24] 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?

[28:32] Yeah, I think that the biggest outcome for me has, number one, been... [28:37] really being close to the metal in terms of building out AI products. [28:42] And I am the one that is like, [28:45] you know, able to have very, very detailed conversations. Like, for example, I didn't get a chance to this morning, but [28:51] I'm going to go and start using Gemini 3. [28:54] as part of this app. And there's certain types of [28:58] it's gotten me very close to our code base as well. [29:02] So for example, I have like, [29:06] I use code Excel right now. [29:08] I'm only using it on this particular app, but I could go and be like, [29:13] Tell me about... [29:16] uh, [29:17] 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 monorepo. [29:28] And so a lot of times, like this happens to be telling me about this repository, right? But this is like a really good starting point. [29:36] for anybody who's going to go build something, because then you can start to understand, well, how is this app that we build actually built? [29:44] And I think that it was almost something that was inaccessible unless you were sitting there and like, [29:50] reading code, which sometimes I do. But I think that this is very accessible to anybody. [29:56] This is awesome. And again, you can just add [29:59] modules, you can spin up new quad code interfaces, and then you can design whatever you want on the front end. It can look however

[30:07] Exactly. Whatever 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... [30:25] 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 going to do the work. We're going to get into it. [30:40] 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 I'm going to say, [30:53] This is a little bit of a different how I AI, which is how I AI into... [30:59] an organization and you've done these builder days. So tell us a little bit more about this. [31:03] Yeah, so we did a builder day last Wednesday. So this is pretty fresh. And that's the second builder day. [31:10] that we did in this particular way. [31:13] So maybe first I'll talk about the results because I think that it's actually helpful to see that. [31:18] This is a screenshot from Hex that was a dashboard that shows all of the roles under my team. [31:25] And then after Builder Day 1, which was just design... [31:29] 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. [31:37] And then it became this like kind of sustained use because we helped people get over that hump.

[31:42] And, you know, not everybody is. [31:44] 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, products, data science, user research, analytics, engineering, you know, lots of different functions. [31:57] Build for Builder Day. [31:59] 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. [32:09] Um, but, [32:10] You know, this is like I'm excited to see, like, does this continue to be sustained? [32:15] Is this something that people start to use as part of their day-to-day approach? [32:21] And I really think about an organization kind of similar to any normal distribution curve [32:28] where you're going to have, you know, it's the innovator's dilemma where you have like the early adopters. [32:34] Right. And, you know, we've we identified a lot of these early adopters here back in like March, let's say. [32:40] And then those people actually built out the scaffolding for me for our first builder day. And then as we had more and more people working, we actually had like a bigger user group. [32:50] that was inside our organization that were maybe the early majority. [32:54] 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. [33:02] that are by just trying to reduce the friction and then trying to lean into the people who [33:09] are really embracing that technology. And 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. So this is the outcome you're trying to drive, which is like, we want to use these tools. We

[33:32] spike, but overall in our day to day, those tools are useful to my team. And so explain to us what [33:39] a builder day is and how it drives you towards that outcome. [33:42] Yeah, so 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. [33:55] And so we had a couple of different types of tools [33:59] We lit up Cursor, Figma Make, and Webflow, and I'll talk about how we actually enabled the organization around that. [34:07] And then we actually had 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. [34:16] You can validate user interactions, you can test product concepts, you can build a full end-to-end workflow. [34:22] So we also had them do like a warmup assignments. [34:26] And then we basically had support channels. So we had a couple of engineers that were on call for this. [34:31] 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. [34:39] different categories. And then we, you know, really focus on like, how do we measure success and do this again? [34:46] And so, you know, this is something that is like evolving for us. This isn't 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. [34:57] actually like taking one step outside of their comfort zone. Amazing. And so this is something that for the leaders out there that are just looking to like, how can I accelerate this?

[35:08] adoption, how can I 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, [35:22] real prototypes and prizes people love. [35:25] 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. [35:34] in just becoming more AI native. And I would just ask you, 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? [35:48] 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. [35:55] Most people were not frustrated, which made me really happy. [35:59] which meant that we had gotten around a lot of the technical issues. I think people found it fun, empowering, motivating, and eye-opening. [36:06] I don't think people understood what was possible. [36:09] Yeah. [36:10] And that to me was like, [36:12] the most heartwarming thing I could possibly imagine. [36:15] is all 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. [36:25] And that just made me really happy. [36:28] So to recap this for any of the CPOs or executives or aspiring CPOs or executives out there, [36:36] 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 it's very important in almost any way.

[36:48] 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 software. [37:07] that has both sort of agentic access properties where cloud code could use it and [37:13] 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. [37:33] 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... [37:49] onboarding, educating, engaging, and driving sustained adoption of AI in your org through. [37:56] these sort of spikes in builder days. And then you're just having fun. Are you having fun? Because 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. I think it's the most amazing time [38:13] to ever be doing this job in the entire time that I've been doing it. 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.

[38:26] I completely agree. Okay, let's do some lightning round questions, and then let's get you back to... [38:31] I just have to call it out your two cursor windows. Down at the bottom. One of us, as we say. Okay, so first lightning round question. This is hyper, hyper, hyper personalized software. [38:46] 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, [38:54] chief of staff for your app you know where where do you fall on this like personal software versus small market sass for for something like this [39:03] I think that parts of this are probably a product like I'd imagine that [39:08] you know, maybe [39:10] Anthropic tries to build this themselves. [39:12] Right. Where it's like everybody's chief of staff, not just for a product leader. [39:17] that may not [39:19] kind of get it everything that people want [39:22] And so you may end up having kind of extensions off of that. [39:26] Right, but I think there's going to be a whole ecosystem around how to actually kind of get work done. And what people are doing with MCPs is just the beginning. It's still like... [39:36] let me tell you, like the very early days of being able to access company data? [39:41] But I do think that this is an app. I just don't know if it's going to be exactly this form factor. [39:47] Yeah. [39:48] 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?

[40:06] Yeah, I actually tried to share a little bit of that in this. [40:10] in this app so that you can kind of see that. [40:13] But I think that AI [40:15] 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, [40:22] you know, like builder culture, career ladder. [40:25] interviewing like you had to look at every single aspect of how you you know your operating system for your team [40:32] and kind of grade yourself and be like, how far have we moved? [40:36] 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 and push the limits of our product. [40:52] And it's not just for themselves, it's for our customers. [40:57] And then I think you have to kind of like reinvent so many different parts of your practice as a leader. [41:03] And so that's the skill that you kind of need to lead into as a leader is just like reinvention at all times. [41:10] Okay, and then my final question for you, I ask everybody, you have dueling clods open too, so this is an interesting question, but... [41:19] When you are prompting and... [41:22] He's just not listening. He's just not giving you what you want. Or your chief of staff is too mean. This is really funny because usually... [41:28] I see so many AI agents be too nice, but yours is actually really mean. What is your prompting technique? Are you an all caps? 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?

[41:45] My prompting technique is first, when I don't like what it's giving me, I will clear cloud code. [41:51] So a lot of times I'll like, [41:53] clear it and then I'll try again. And if I'm still not getting what I want, I'll be like, be a hundred X more this thing that I want. [42:00] 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, [42:08] go and just like rip it apart and do something else. [42:12] 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... [42:28] 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? [42:40] Yeah. [42:42] Thanks again, Clara. This is amazing. I'm [42:45] at Rachel Wolin on Twitter. And you can also find me on LinkedIn to follow me. [42:51] And I also recommend checking out [42:54] Uh, webflow.com. We have a brand new app gen product that we just released last week. [43:00] It's really for your marketing team to be able to do vibe marketing, which is a whole new wave that we're riding. [43:07] So... [43:08] Amazing to be here. [43:09] Awesome. Thanks. And I appreciate you sharing all your tips on how I AI.

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