Inspired with Alexa von Tobel
00:03:12 · Alexa von Tobel, Max Shaw
[00:03:12] S2: Let's go NYC. Max, what about you? [00:03:16] S3: Awesome. Well, I met Brian at Yext. I was there for ten years where I led product globally. I would... Did not have any motorcycle businesses, but I'd... I have built a bunch of random apps over the years, a lot with my other cofounder, Mark, who we've met in college together. And the most prominent is probably this app called Gifjif, where you can put your face on a GIF. This is all pre AI, but it was a lot of fun. [00:03:43] S2: So we just announced, and I am so excited that Inspired is your teammate, early stage seed investor here, and everything that we're building with Windmill. And before we just even, like, dive into the future, what is Windmill in plain English from your guys' head?
00:04:01 · Max Shaw
[00:04:01] S3: Yeah. So Windmill's the missing system that I've always wanted throughout my career. I was at Yext. I started as an individual, then eventually managed a small team, and then I ran a pretty big team. And it felt like this... There's this missing system that allowed me to stay on top of my team, to understand how people were developing, and to help them grow in a scalable systematic way. And that system just didn't exist. And in the age of AI, one of the things that kind of been part of the founding story since the beginning is that as each individual employee gets a lot more leverage with AI, everyone is running their army of agents, people end up mattering a lot more. And having the right person in the right role with the right set of responsibilities is now more important than ever. And we think the companies that win in the future are not gonna be the ones that automate the most people out of their jobs. They're gonna be the ones that put the best talent in the exact right opportunity for them to excel. In order to do that, there's this missing system that just doesn't exist. You have your org chart in your HR system. You have all your productivity apps where all the work actually happens. You have, like, a performance review system that's disconnected from both of those. And if you wanna start to use AI to help understand your talent, understand your people, we think the most important asset going forward, you need a new system that synthesizes all this context together. And so Windmill is building that missing link. We call it the context graph for your people. And with that, you're gonna be able to develop talent and to scale out organizations and to orchestrate your teams in an entirely new way. And so we're building that missing foundation.
00:05:38 · Alexa von Tobel
[00:05:38] S2: Let's talk status quo, guys. I, you know, was a manager at a Fortune 50 company. I I I... You know, when I was trying to learn best, I'm very familiar with performance reviews. They're always quite awkward. I think many companies don't even do them. And yet when I think about in my own career, probably the moments that I'm most grateful for have been moments of genuine, thoughtful feedback, where somebody said to me, you're great at this. Keep doing it. You're terrible at this, Alexa. There's always been a long list. Do less of it. Or here's a tool to make the thing that you're not good at better. I mean, truly, and I could not be more sincere in saying that that the gifts of my career have been moments of really thoughtful but critical feedback. Where upon reflection I was like, gosh, feedback is a gift. And I know we all sort of say it, but actually don't mean it because it sucks. It's such a gift. It is such a gift. What's the status quo right now, Max?
00:06:43 · Max Shaw
[00:06:43] S3: Yeah. The the status quo is is pretty bad, I would say. And most of it is extremely inconsistent because the status quo relies entirely on how good is your manager. And there's no consistency. There's no real system in place for any of this. Maybe you have an HR performance view tool that you use once a year. But outside of that, there isn't a system that is kind of understanding any of these pieces of missing contacts. And so ultimately, it often comes down to how good of a job does your manager do in terms of giving you feedback, giving you coaching, giving you advice on how to succeed. Right now, we talk to a lot of ICs. Pretty consistently, everyone says they're not getting enough feedback. Everyone wants to under... Especially the ones who are ambitious and trying to grow, they wanna get more feedback on what's going well, and more importantly, how they can improve. Constructive feedback is pretty nonexistent across a lot of organizations. And most HR teams spend the vast majority of their time just trying to administer existing processes. And they don't really have the time to think more strategically about how do we change the culture into one where feedback is... Focusing on feedback, feedback is given a lot more frequently and in the moment. And so there are pockets where you have examples of managers who do a really good job at this, but unfortunately, that's not the status quo. And so too often, you're getting feedback once a year in a performance review that doesn't really reflect actually what happened because the manager forgot most of the stuff that happened over the last six months. In early my career, like, I... Especially when I was not a manager, I would always say, like, oh, my manager just kinda sucks. And then you start managing a team, then you start managing a big team. And recently, there's been a lot of news about how organizations are flattening. Yesterday at Coinbase, they talked about how people are gonna have more direct reports. If people can't handle this at five or six direct reports, it's all gonna completely fall apart at 10 or 15 or 20 direct reports unless there's a new way of thinking about this stuff and a new system in place. And so so that's how we're thinking about it. But the status quo is is not great, and it's extremely inconsistent.
00:08:44 · Alexa von Tobel, Max Shaw
[00:08:44] S2: Let's dream a little bit about Windmill, and let's just talk a little bit about what the product does today and where it will be in two years. Because the status quo is, again, a a pretty, like like, very rudimentary. Here's what's going well. Here's what's not. Maybe a three sixty review. Maybe if you're more senior and important enough, Or if you're really important, they'll hire you a coach who will then also give you a lot of... But that's like for the... Maybe the management team, maybe the c suite, and that's [00:09:20] S3: it. Mhmm. [00:09:21] S2: Let's let's talk about what Windmill does today and where Windmill's going.
00:09:25 · Max Shaw
[00:09:25] S3: Yeah. So I I think right now, what we're focused on is making the existing processes 10 x better. And so that is primarily performance reviews, pulse surveys, which is a quick way for people to get feedback on how stuff's going, and then one on ones. And the way we've made those products... Those processes 10 x better is that we infuse all of the context. So as an example, in the one on one, the system already knows what the person's been up to. Right? So you don't need to spend your one on one trying to catch up on the status of existing items. You can focus on employee growth and development areas. In the performance review, similarly, the system already knows what the person did over the last six months. And so you don't need to spend time trying to remember what happened. You instead focus on the more meaningful part, which is kind of understanding and thinking about it at a high level and and trying to pinpoint where this employee can improve. And so that's really the... Where the existing product shines is taking these existing processes and then making them 10 x better. Longer term, I actually think a lot of these existing processes will start to look very different. In a few years, I think the concept of running a performance review cycle once or twice a year is gonna be extremely outdated, and the system will be used in a much more continuous fashion. You're not gonna have to shut down the company for... It used to take, like, for multiple weeks with Windmill, it can take just a few days. But why would you only do this important process once a year? If it's so important, Alexa, you talked about how it's like one of the most important parts... Things you remember is about getting that feedback. Why is it happening once or twice a year? And the reason is because it's so time consuming. And so if you're using... Able to use AI to make it much, much faster, you're, of course, gonna do it more frequently. And that's gonna pretty fun and fundamentally change how you think about this, and it's gonna go from these once a year processes into a more continuous coaching pattern.