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

0:00Rachel Wolan:So you've built yourself an AI chief of staff. The AI chief of staff is actually something that I have been trying to build since I started vibe coding. There's a lot of repetitive things that I have to do. For example, like prepping for podcasts and speaking engagements and stuff like that. And so I've built an agent that preps me. Let's go into a specific workflow of how this chief of staff actually helps you with do something. I think you did a little prep for this podcast. I basically prompted and said, hey, let's generate a How AI flow. And so I was trying to get it to tell me what should I actually demo that is going to be part of this chief of staff app.

0:34Rachel Wolan: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 web flow. Just the ability to be prepped even in a few minutes ahead of these things can really make your life better.

0:52Welcome back to How AI 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 Wolin, CPO at Webflow, who's going to show us how she uses AI, cloud code, and personal software to run her life and her business day using AI as an executive. She's also going to show us her formula for teaching teams how to use AI, drive adoption, and get them in those new tools with excitement. Let's get to it. This episode is brought to you by Graphite, the AI-powered code review platform, helping engineering teams ship higher quality software faster.

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2:22That's graphitedev.link slash howiai. Rachel, welcome to How I AI. The reason why we are doing this podcast together is we were sitting at a very recent San Francisco-based AI event. And we were talking about how so much of the discourse is around the AI native PM, the AI native engineer, basically like the AI native IC. And we spent a lot of time on that topic here at How I AI. But you and I have been chief product officers, and we 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.

3:18So how did you get here? Because I will tell you, not every executive is as into this as maybe you and I are. So what kind of clicked in your mind to get you thinking like, my job's going to change. I really got to figure this stuff out.

3:30Rachel Wolan:I started coding when I was 16. And, you know, it's obviously been kind of a lifelong journey of building and tinkering and, you know, making mistakes. And so I feel like I kind of built that resiliency pretty early in life. And now in my current role, you know, I probably hadn't coded in about, you know, six or seven years. And then when all of the new 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. but you know when it was when kind of like vibe coding started coming in the scene I actually built an app to capture my kids memories and that was the first vibe coded app that I built and I built it in a weekend and it was it just felt like something completely different than anything I'd ever built before and you know here we are a year later and this is you know now I'm like sitting in cloud code all day and I you know this is an app that I kind of like I'm continually maintain it.

4:37Rachel Wolan:You can see that I'm running it on local host. And, you know, 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 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. 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.

5:25And then in 2023, 2024, it just became easier to go zero to one on stuff. It wasn't that I didn't have technical skills. It was just I didn't have time, time to do things. And so the ability to, you know, do AI assisted engineering or vibe coding was it just brought me back to the love of coding and building things. And so I hear that a lot. I certainly feel 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.

6:07I think these vibe coding platforms are some of the most addictive games on the market right now. And so again, you don't have to start with something at work. You can start with something that's personal. And I think once you get hands on and realize what's possible, it's hard to think that your day-to-day job is going to be the same. So let's get into what you built because I feel like I need this. So you've built yourself an AI chief of staff. Tell us more and how you're using it in your everyday life.

6:40Rachel Wolan: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 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 agents. I've just kind of been, you know, taking away different use cases. And then a big part of this is also, you know, I really want to help my team level up. And so it would be inauthentic for me to tell them, hey, you need to prototype with AI. if this isn't something that I'm doing every single day.

7:22I completely agree. And one of the things I want to call out about how you're talking about building this software is one, you're building it for an N of one. You're building it for yourself. So it can be really hyper-customized. Two, you're building sort of a multimodal interface to this in which it can be a web app or it 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, and you may want to do it completely differently the next time.

8:02You 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 so let's go into a specific workflow of how this chief of staff actually helps you with do something. I think you did a little prep for this podcast.

8:24Rachel Wolan:I did. So I will actually run different terminals that are all running Claude. I do this partially because, you know, I want to make sure that I'm like not using too much context. And then I find that when I'm asking questions that are of a similar ilk, I get better answers back in that same terminal window. But I basically prompted it and said, hey, let's generate a HowAi 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.

9:03Rachel Wolan: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. 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 the two seconds before I'm walking into a meeting, that's the time I have to prep for that meeting with very rare exceptions because you are just back to back to back to back to back to things. I say sometimes to people, the number one skill you need to learn as an executive is improv because you are just dropped into a wide variety of contexts.

9:47You 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 make your life better. So let's go through, okay, this is a very specific example. It's sort of our meta example on how we're going to go through this show, But let's talk about your morning triage and how you start your day every day using this AI chief of staff.

10:11Rachel Wolan:That sounds good. So 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? Because I think that I don't have a chief of staff anymore. I used to have a chief of staff at another company. And so I knew that this was something that they would be like kind of combing through my calendar and like, hey, you're not blocking your energy. Right. And you're not like kind of taking care of yourself. And so, you know, the main thing that they kind of called me out on, which I thought was really funny. So we just had our customer conference about a month and a half ago.

10:47And, you know, I haven't taken quite as many customer calls.

10:51Rachel Wolan:And it's basically calling me out and saying, you know what, you're not spending enough time with customers. And that's where you get energy from. And so it's basically like doing a time analysis on my external calls. I'm like, how is that possible? and again it did pick up it wasn't like a hundred percent correct and so i think that but but it was kind of like a signal to me i'm like oh this is a place where i need to go and like reinvest right and it's like you're a cpo with like no regular visible cost for contact fatal flaw and i'm like oh gosh um it's very like dramatic right uh well how does this actually access your calendar or how have you technically built this?

11:26Good question.

11:28Rachel Wolan:So I 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. 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.env file. I'm not going to show it to you because able to burn all the tokens I have in there. But it basically has a bunch of variables. And so one of those variables is my Gmail. And then it walks you through how to actually go and set that up.

12:05Rachel Wolan:One of those variables is my Google Calendar. And then I give it certain authorization. So in the case of Google Calendar, it can only read my calendar. In the case with Gmail, it can only create drafts. It can read, it can archive, and it can create drafts and label. And so a lot of this is like thinking about how do I, you know, put the right guardrails in place. It's kind of like thinking about software, right? How do I put the right guardrails in place so that I don't make mistakes or the agent doesn't make mistakes? It's kind of janky software, right? Because I mean, because I'm like, oh, this is like pretty powerful.

12:43Rachel Wolan:And then a lot of times I'll like go and kind of take some of the power away when I realize I've given it like too much, you know, too much authority to act on my behalf. And so I think that's, you know, part of it is also like me populating my own, you know, kind of intuition about what feels good in working with agents and what feels like it's kind of like overstepping. 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 are you doing, girl? Let's fix this. But tell me how you would use this on a daily basis.

13:23Rachel Wolan:So tell me about my day tomorrow. What can I delegate? And so this will run for a couple of minutes. And when it comes back, it'll tell me this is what's coming up tomorrow. This is what I think you can actually, you can do something else. This is, you know, I think the way that I would like to make this smarter is this is who you should delegate to. And then, you know, I'm still kind of working on my Slack agent. So I can't show you. But what I want to do is basically like send notes to my admin and be like, hey, could we go do this? And is this fetching the calendar events through an MCP? Is it some custom code that you wrote?

14:03Rachel Wolan:This is fetching it through an API token. I don't think that there's an MCP that is like a official MCP. But what you kind of see, this is why sometimes I like looking at my briefing. So other things that I do here, I actually have a little note card that I like to make for myself. I'm like, I did prep for you. That's good. and then you know I'm basically kind of looking at this the thing that I like about it is it like makes it just very easy for me to get a snapshot and and view it but I'm still kind of like iterating and what do I want this to be like let's just take a pause really quickly on your web app while this is running in the background and what I love about what you've designed is look we're all running on Google Calendar or whatever, but you want it to look a certain way.

15:01You want it to be designed a specific way. You want to have a, can you show us that little note card really quickly? I got this idea from Mark Andreessen about like, what are my top priorities for the

15:14Rachel Wolan:day? And then did I actually accomplish it? 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, sidecar on design. So you have your top priorities. wordies. 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.

15:58Rachel Wolan:And I think that's like part of what is fun is like, okay, what would that actually be like if I translated this app and I had like a theme for it? And so there's something, there's something really fun about like actually getting to design again, but not actually, I mean, it takes the amount of time. It's not, it's, it's not at like the pixel level perfection of the incredible designers on my team but it does at least convey like you know there's a certain um je ne sais quoi of this like app that i'm trying to to capture to make myself happy yeah i love it it's so great um okay so here we go here we go Yep.

16:39Your chief of staff is very mean. I tell it to be mean to me. That's why.

16:46Rachel Wolan:I want it to like keep me in line. You know, I'm one of those people who likes to try to take on too much, I think sometimes. Okay. So it's basically telling me to make certain meetings async. That's a great idea. It's telling me to delegate a couple of these. This is also probably a great idea. I don't think I can delegate this one, but good call. It's telling me there's too much clutter on my calendar. This is one of those things where somebody's just like, put something in my calendar. I don't know this person. So that's definitely optional and I haven't accepted. And then it's like, can whatever director cover this and send me a summary?

17:23Rachel Wolan:And this is really helpful. This is 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 to do some work and maybe get home to my family at like a reasonable hour? 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? So even giving 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.

18:00And again, we're talking about the AI native exec, just too busy, overbooked, underprepped, really just wanting to spend our time vibe coding. So I think this is really, really useful. And again, I like this because it's very conversational as a chief of staff might be. It really helps you sort of figure out what you can do with your calendar and then I like how it's mean to you. What's the brutal truth? Let's look.

18:30Rachel Wolan:The brutal truth? Is that... I'm like, yep. Because being a senior PM sometimes sounds more fun. I know. I'm like, is that bad? Is that a bad thing? 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. 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 because no matter how fancy of a title i got i still was writing prds all the time and so this is this is really really great and then i love this idea of like the only thing that will matter in six months are is this conversation what an amazing way to level up so chiefs of staff staff that are watching here, you need to end every meeting with your exec with the brutal truth and build this for yourself.

19:34Okay. So this gives you a really good prep for your day. I'm presuming you do a very similar workflow for email as well. What is outstanding? Can you just walk us through maybe just some of the problems that your email chief of staff solves?

19:48Rachel Wolan:Yeah. I mean, I think that My biggest problem is that I'm like 500 emails deep in my email. But it's basically archiving a bunch of stuff that I don't need. It's keeping a few things in the inbox and then it's drafting a few responses. And, you know, a lot of this is like I've been kind of like continually updating this particular agent to know where to draft responses. Sometimes it drafts responses, you know, like some random SDR inbounds to me. And I'm like, no, no, no. You don't need to like draft responses to this person. But a lot of times it'll be like, you know, somebody from like a, like a partnership type of email will send me an email and it'll tell me, Hey, you need to pay attention to this email.

20:32Rachel Wolan:So a lot of it is like trying to also know like when somebody is waiting on me and asking for some document to get shared. Right. And so, you know, this is like kind of a cursory view and then I can go through my inbox like very, very quickly. um i'm i think the slack version of this is going to be like an absolute game changer since we operate almost internally in slack 100 percent 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 yeah um so i feel like that's like my next that's my next hill to climb 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.

21:21So disconnected that fancy pants, large language models cannot make sense of it. But for some reason, us with our meat brains are expected to be able to do this. And I just think that is such an indictment of how we're expected to navigate the massive amounts of information as as people that are working on teams in these asynchronous or semi-secretous ways

21:45Rachel Wolan: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 you know that we're obviously only what you know four years five years into that experiment And so I think that we haven't like the tools haven't quite caught up with what we need to kind of declutter our brains through that kind of transition. So I still think we're in like the early days of how to effectively do remote work. But that's like a different topic for another podcast. The early story of Atlassian is probably very similar to your own.

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23:08They 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 slash startups slash how IAI for more details and eligibility. Okay, I want to do one more fun chief of staff example before we go on to our next workflow, which is how do you prep for dinners? Tell me about this little tab is calling my name. I must know.