Michael Grinich - founder & CEO of WorkOS

jack bridger (00:00.11)
If a conversation scares you, if you're like hesitant to do it, it's something that probably needs to be done. If you're feeling anxious or nervous about it, you're avoiding it, you're procrastinating doing it. At the beginning of it, you just say like, this is going to be a tough conversation. If you're the founder or you're the CEO and you're unwilling to say that or have that conversation, guarantee no one else is going to be willing to do it. Hi everyone. You're listening to Scaling DevTools. I'm joined today by Michael Greenwich, who is the founder and CEO of WorkOS, who has been on the podcast before.

talking about how to cross the enterprise chasm. And that is kind of what Work OS is all about, is that it helps startups to cross the enterprise chasm, giving them everything they need out of the box to do that. Thank you so much for joining, Michael. It's great to see you again, Jack. Yeah. And how's your conference experience been? It's been really great. Probably of all the different events I've come to, this is the highest concentration of engineering leaders that are here. For our product, for Work OS, even though it's something that helps.

startups generally grow in scale. The alternative to using Work OS is usually to build something in -house. And that decision's often made by engineering leaders, people that are in management or executive level roles. So even though the engineer is gonna be the one to write the code or actually do the integration, sort of the person buying it, the actual budget comes from the engineering lead. And a lot of those people are here. And so they've come by our booth and said, I've heard about Work OS or what do you guys do? All different parts on that spectrum.

We gave a talk yesterday, Aditya from our team talked about our new fine grain authorization tech and some people came over and wanted to hear more about that. So it's just kind of a great time to engage with people like that and just a lot of fun too. Yeah, that's very interesting. I know like on the show we talk a lot about developers, how developers like to see code, developers, how to reach developers, how to get developers to try things out. But I think engineering leadership, a lot of the stuff I've seen spoken about here is much more.

at a higher level how to structure your organization, reorgs and stuff like that. Have you found it's quite different to market to the engineering leaders versus the kind of individual? Yeah, most people here were developers at some point in the sense of they were writing code, building stuff, hands on keyboard, started their career in that way. But now what they're typically thinking about is resourcing. They're thinking about where they put their limited

jack bridger (02:24.426)
actually engineering talent that they have on their team. And really they're thinking about business goals. They're not just thinking about what specific technology should I use or is it better to write this in Rust or Elixir or should I upgrade our latest version of React or Next .js. They're less interested in the actual specifics of the technology and more in the impact it has on their wider organization goals. Recruiting and building talent is a big part of that.

how to weigh priorities and trade -offs is a big part of that. Building new teams like security teams is definitely a topic that's been discussed. Everybody here is talking about AI, how they can leverage AI, ways that they're using it to be more effective and scale faster, not to mention in their own products, shipping it. So it's definitely like kind of higher level conversations. Pretty different than if you went to a conference, I don't know, like, know, like Vercell's Next .js Conf.

That's very much about Next .js, the framework. They put code on presentations and screens. Most presentations here don't have code. Ours did a little bit, but most of them don't have code shown. Yeah. And so how do you try to align Work OS? Because if you're talking to the individual, you might be saying, yeah, you don't have to build SAML yourself and stuff. How does the message change in that? Yeah, it's not about the specific feature. It's more about the wider company impact.

helping companies go up market, helping them scale. What are the deals that you haven't been able to close, the customers you haven't been able to expand to because you've been missing these features? So not necessarily the way in which we do it, but the end results on a business. That tends to resonate more with executives or people that are thinking about staffing teams, thinking about projects on maybe several quarters timeline, a year or two. A lot of those people are here. Those engineering leaders are here.

So sometimes they're interested in telling me, how do I actually do it? Show me the code. Show me a demo. But more often than not, they're like, what do I actually get from this? Walk me through the impact of it long term. Yeah, that makes sense. And so if you have a nice conversation with someone, where does it go from there typically? Yeah, well, something that's different here at this conference compared to other ones that might be just technical is we actually have salespeople here. So there's people at our booth, which is literally right on the other side of the camera, right behind us.

jack bridger (04:48.098)
that are staffing that booth, talking with people as they come by. And usually that conversation is like, hey, I'm interested in what you're doing, or I've heard about it, or I had a couple questions. But it doesn't get into too much depth here. Usually what we do is get their information. We'll send them a follow -up email, set up time to have a deeper chat, whether that's to talk about specific product features, to have a talk with a solutions engineer about architecture, to talk on the security side. Sometimes they're ready to go. They just want to understand pricing.

or kind of commercial structure stuff. But this is just the beginning. It's kind of just step one usually. And we keep coming back here to this conference for ELC because we've had customers that have discovered us here and months later actually sign up and use the product and we can tie it back to our presence at these events. So it's pretty good. It starts sometimes from just one little conversation, a great customer relationship can be built. Yeah, that's very interesting. if someone's just getting started,

kind of like really early stage dev tool? Would you say like conferences or like, you know, they should get a booth for ELC or, you know? Yeah, it's a great question. So there's so many events and so many conferences and you can just get stuck doing events forever. I mean, there's, there are people that reach out to us like advertising events to have us come sponsor it because they're starting new things and new places. So you have to be very selective. think you have to pick.

What I do for us for conferences is I will always go just by myself the first year to scout it. So no booth, no team, no presentations. I'll just buy a ticket for myself and usually just go for like a couple of days and go check it out and do like sort of a vibe check. Are there people that I think could be customers? Is the tone or the type of, know, kind of topics relevant for us as a business? And do I think if we actually brought a team, it would be impactful, you know? So the first year for ELC, that's what I did. I just came and...

bought a ticket, met some people and I was like, yeah, this is it. This is a good spot. There's many events I've gone to where that's not the case. I've gone there and I'm like, not so much, not really our vibe. And maybe not exactly how our team would fit in. One that I went to last year for the first time was reInvent, AWS reInvent, which is in Las Vegas in December. And I just bought a plane ticket, got a hotel room, just went by myself and I was just blown away. I was like, this is crazy. It's like 80 ,000 people.

jack bridger (07:08.992)
all talking about SaaS and cloud and tons of other companies and vendors there, not just AWS. I spent a bunch of time talking to folks from Cloudflare and Datadog and LaunchDarkly and all these companies that we really love and we've learned a lot from. They've inspired us. So this year, going back to re -invent, we're actually bringing a team. We have a booth that we're going to have and meet a bunch of customers there. So that's my recommendation is kind of like dip your toe in the water because it's a big investment. I mean, it's...

Of course, money, you sponsor the booth, you have to pay for stuff. But it's really just time and focus. If you're going to bring your salespeople away from engaging with customers online, if you're going to bring, in this case, had a couple engineers coming to this giving talks, that's big investment. The time is the hard thing to get back. So for every business, it's different. For every business, their product might have a different audience or different place to go to. I wouldn't say ELC is perfect for everybody.

But it's a pretty good one for us selling to developers and specifically engineering leaders. Last thing I'll say about that, if you want to get really scrappy, I remember one year I was at Saster and we had a booth, we had a pretty good sized booth, brought a bunch of people. there was this guy and we're handing out swag, right? We're handing out hats and candies and stuff and ice cream. And this guy came around giving out, I think it was like popcorn or something.

And he didn't work for the conference. He didn't have a booth. He was just a startup founder. He was doing like the reverse pitch. He was going out to people at their booth, pitching them his stuff. And I was like, this is brilliant. He doesn't have to pay for anything. He doesn't have to, you know, like actually kind of register, you know, $40 ,000 in advance or more. He was able to actually go after the same, you know, audience, but prototype it himself, just like hustle his way into it. And...

That's pretty fantastic to see that level of hunger and energy. And I don't know if he ended up going back the following year and getting a booth, but that type of attitude typically compounds and results in success. really admired it. Yeah. Yeah. You do see sometimes, like as a lot of times, people just like standing around and like just waiting where like other people are like, you know, talking to everyone that goes by and stuff. does seem like there's a lot, like they're very tiring conferences, but like.

jack bridger (09:28.418)
That hustle is... You can't be reactive. You gotta be proactive. You gotta pull people in. It's kind of like a... And if you're in a... Like New York, walking around Little Italy at dinnertime, then there's guys outside the restaurant. They're like, come in, come in. They're not just waiting for you to come in. They're kind of pulling you. The best booths, the best conferences, people have that hustle. And it's exhausting. mean, it's for sure tiring. You gotta take...

take turns, hand off stuff as people get, you know, tired from it and cycle through. People that think conferences are just time off of work or vacation. It's like totally not the case. It's the opposite. It's, it's like really, really dialed up intensity. It's draining. It's draining. Yeah. Could you tell, tell me a bit like, you know, when you're thinking about organizing your own conference, why are you thinking that that's like a good thing to do? What are you, what are you hoping to get out of it? Like, you know, that sort of stuff.

Yeah, I think we have a lot of ideas around what it could be, know, and a lot of aspirations around where we could take it long term. In the future, we would like to have an event where there's many companies talking about what it takes to become enterprise ready, what it takes to actually scale up market and really grow and develop your business, know, post product market fit. What do you do?

That's a topic much wider than just SAML or SCIM or these things that we provide. And it's really universal to every business, every software business in that sense. Now for the first one, it's not too realistic to get other people to come sponsor. It's really hard to get other people to give talks.

and just to coordinate across multiple folks. So for the first one, it's really just mostly us speaking. We're gonna have some external people on a panel and some external pretty cool fireside chat we're gonna do at it. But it's mostly us. So in terms of how we're thinking about it, we're like, okay, we'll shape it. We'll put the structure around it. We'll fund it too. We'll pay for it. But the whole point of it is to be an experiment. So long -term, we'll know how to run an event. We'll know how to invite people. We'll know how handle.

jack bridger (11:35.942)
everything from food to security to making cool swag for people that come by, to the ticketing stage beforehand and checking them in. We're hoping to learn about all that stuff and then also at the same time be able to actually announce some cool stuff that we built, showcase some features, use it as a bit of an event to focus a lot of the work that we've been doing over the last year.

So I'm really excited about it. You can probably tell it's going to be really cool. And the design, the design stuff of it is super fun. I mean, if you like designing products, a conference is kind of like a product that you like sit inside of, you know, it's a temporal one day product that you get to experience.

We have some cool stuff for that too. Yeah, it's like a whole experience. Yeah, totally. Yeah. And I also have another question related to what you mentioned earlier about like, you know, how you would just turn up to a conference and try it out. Someone asked a question in your talk yesterday about frameworks and you were like, I don't really believe in frameworks. I think it's more about your intuition, trying things and seeing what works for your company. I wonder if you could talk a little bit about...

your feelings and your beliefs. Sure. Yeah. I think I used some more explicit language when I was talking about frameworks. frameworks can be useful to explain things that have already happened. I think if you want to do an analysis and you want to categorize things or fit them into certain structures, thinking about it in terms of a framework or in terms of patterns can be helpful. When you look at industry analysts, someone from

know, Gardner, Forester, or like a McKinsey report or something, they usually put it in terms of frameworks that are easy to understand. And I think what you're focusing on there is like legibility of a market. is market is this like organic, kind of expanding crazy thing? And how do we make some sense of it and be able to talk about it? That's what frameworks are for. And they're helpful for that, to put structure around it. The problem is if you try to use the framework as a genesis point for new ideas, it's extremely constraining.

jack bridger (13:41.058)
And I think you kind of just don't get anywhere from it because it's too categorized already. so instead, rather than using a framework, the question yesterday was using a framework to kind of come up with an idea for a startup to build, like which directions you could go. My answer was more like, you should just go talk to a ton of people, build empathy with those users or with the market, really, really try to understand them and understand what makes them tick, what problems they're having, what's painful for their job, and then use that empathy to shape your idea of what could be better and then go build that.

It's not really a framework, you know, and it's messier, but I think it's a more likely source for like getting to like the bedrock of the idea or the actual pain that a person is having. Yeah, you actually used that phrase in the talk as well about like drilling down like why, why, why, why? And I think that was in the con that was on the subject of narratives about like your why and you were saying like drill why, why, why until you reach bedrock.

Yeah, think I just continue to ask why is really important and like being unsatisfied around the answer. And so you really get to the root of it. Why see has this great thing about going and talking to users and and forcing developers to go talk to users, mostly engineers and why see companies talk to users, talk to users, talk to users. It's one of our operating principles at work. OS is talk to users. I think the reason why it's valuable is because you always learn something and there's this tendency to assume you already know.

what the users want. You're very quick to just make that idea real. We're smart. We can figure it out. Yeah. And like, I totally know what they want. Or I've seen a few examples, and I got it. I got the solution. And for whatever reason, otherwise really, really intelligent people do that, and then you're off. No one gets it exactly right. No one figures it out initially. And so the talking to user step is something that generally invalidates your assumption very quickly.

And what you don't want to have happen is like spend a lot of time working on an idea and then it turns out to be wrong. So it's like check, check, check, check, check. It's a lean startup methodology. I think that the piece around asking why is part of that. It's like, why is this painful? Where is the value? Why are we doing this? Why is this important? And yesterday when we were talking about this, it was more around narrative of the company. Like why should this exist? Why is it important for us to work on? But why is it really important for us to work on? What is the thing driving us? And it can't just be like to make money necessarily.

jack bridger (16:09.57)
needs to be something like firmer than that. And ideally you can get down to the bedrock piece of it as I say, is like the pain that the customer is having in their life in some way, whether that's a problem they're having with an existing tool or it's like a task that they have to complete or something that's limiting their ability to succeed in another area. The more you can articulate that why, the more clearly you can kind of hold it.

the better you can use it. And that becomes an asset for hiring people, for raising money, and honestly for doing sales. Sometimes if you can sit down with a customer and you can just so clearly articulate the thing that they're feeling pain with, you don't even have to tell them the solution. You can just articulate what they're frustrated with. That person's like, I feel so seen and so hurt. I'll buy whatever you have. It doesn't even really matter, you know, like.

what it does, like just because I finally feel like someone understands me and understands the challenge I'm trying to have. So much of sales starts with like the what, what we've built and then like how we've built it. Here's some new technology. You know, we, built this new orchestration that's, you know, instead of using it instead of Kubernetes, it's better orchestration layer for containers. And we did it written in whatever, whatever language and it's massively paralyzed and it runs on ARM chips or whatever.

But you never get to the why. Like why is this actually important? But if you can start with the why, there's a really good book by, I think it's Simon Sinek who wrote, Start With Why. It's 150 pages long, it pretty much just says this. If you start with that piece, and you literally start with it, you begin with why, it almost instantly builds this connection between you and whoever you're talking to. And if that common ground is established, it's valuable for sales or hiring or.

fundraising or anything. Yeah, I think Adam Frankel in his book, Developer Facing Startup, I don't know if you've come across Adam. I just bought it. It's on my desk at I haven't read it yet. I got it on Monday. He talks about becoming an expert in the problem space and how that's more important than becoming an expert in the solution. Totally.

jack bridger (18:27.48)
Heard this once, I can't remember who said it, but I definitely took it to heart in that you should really try to fall in love with the problem that you're solving versus fall in love with the solution. Yeah, I think that's actually the thumbnail of the last episode that I did with I think about it all the time and I think about it in terms of founders. the thing I've come to realize too is it's not just fall in love with the problem space. It's actually sort of like fall in love with your customers, who they are.

And I don't mean like literally like go off and close maybe. But I mean in terms of like who they are, what they struggle with. One of my favorite things about work OS I've said this to you before is the type of customers we get to serve are amazing. They're like these fast growing usually technology led startups expanding up market with big aspirations with these businesses activating. You know we.

whether it's like perplexity or someone like, know, Versel or the hundreds of other customers we have, we get to work with their engineering teams and their technology teams. It's super cool. It's like, you know, it's the best thing second to going working at perplexity for me is to work with their, you know, engineering team or design team on their future product. I'm just tickled to have that opportunity. And I think that ends up being durable even when a single product doesn't work.

You build a product, you build a new feature and it flops, not everything is gonna be a hit. The thing that can be sustaining as you do through it is that connection you have with the customer, the empathy you've built and hopefully the desire you have to make their problem just go away long term. So fall in love with the problem space and also your customers, become one of them. Yeah, I think that's something I've really learned from you and I think it's quite uncommon.

I think other people do this, but we talked about this before on the previous episode, but you've had the same problem space from day one. And that's part of my armchair theory. You're quite a calm figure. We've hung out a bit. I've seen you in some semi -stressful situations. you always remain calm. And also, you seem like...

jack bridger (20:47.48)
things are under control. And my theory was that, you know, know, the direction that you're, you're going, it's like, you're not constantly thinking, I do this. It's just like, there's this kind of North North star. haven't, we haven't pivoted, you know, as a company that I think that's, it's, it's very lucky. Yeah. There's definitely things that we've changed and things that we've tried that hasn't worked or things that haven't hit as well. But we really haven't.

changed the message or the direction of the company for several years, which is great. Not everyone gets the luck to be able to do that. You have to adapt and change if it's not working. But I think that one of the reasons why it has been for us durable is it's connected to something that's higher than just the specific features we built. We're not the SAML company. We're not just about SCIM or audit logs or access control or authorization.

You know, we're not even called auth OS, right? Like authentication is a big part of what we build, but that's not the name of the company. It's this higher level thing about building a new platform for workplace tools, like the work OS, and this idea of becoming enterprise ready, enterprise ready story. If you can articulate that as your startup, you know, that narrative, or actually just have it in the back of your head as you're building it, those things end up being like pretty durable over time.

And I think for companies as you scale and you grow, you need to figure out what are those invariants that you're gonna have, whether it's, care a lot about design, the user experience or performance or speed or always being at the bleeding edge in terms of the frameworks that you support. Or for us, it's like developers, like developer joy is our number one operating principle. We always wanna build for developers. It's very hard to go add those things later, to add them post fact.

sort of knowing who you are, what you stand for as much as you can early on. I definitely look for that when I invest in people too. You know, I do some angel investing and I'm like, why is this person doing this? Why do they care about it? You know, why, why is this going to be the thing that they actually do want to keep working on for a long period of time? Cause even if you have the right idea or the right market, the right customers, it's enormously difficult to build anything and certainly to build like a startup that scales.

jack bridger (23:12.664)
there needs to be a deeper reason why that founder is going to stick it out and keep building. Yeah. And so let's say someone's built, you know, they had a problem. They experienced, they're like, this is difficult. I'm trying, this is basically me, right? You know, they've built something, it solves that problem. But there may not be a kind of, you know, a sense of like, you know, we're helping people cross the enterprise chasm sort of.

why? Do you think people should try to find that why? Or do you think it's something that is obvious to you? And if it's not, maybe you you keep, you know, doing things until you find that deep mission that you really want to solve. Yeah, that's a good question. I don't know. I think it's very hard to like, if it's an area that you're not interested in at all.

and you're just like trying to come up with any idea possible. You know, it really sucks if that doesn't work out for you, because you put all this energy into it and it fails as a company. But it kind of sucks even more if it succeeds. And now you're stuck working on this thing that you didn't really care about that's in an industry that you don't really feel that empathy with. And over time, you can like kind of learn to love anything. But I guess...

But I think it's easier if it's something you're drawn towards that you find compelling, that it's for people that you really want to spend time with. If you really love hanging out with people that work at restaurants or something, or chefs who care about cooking, build something for the food industry, the food and beverage industry. You'll just inherently be surrounded then by people that you want to spend time with. I think you shouldn't force it. You should just sort of follow your interests. And those will be the areas, in my mind, where the richest ideas are.

You know, the areas that you're like, I Paul Graham even wrote about this. It's like kind of follow, not your, just your passions, but what you're interested in. And don't be too concerned about it, whether it's a good company or not early on, or whether it's a good startup idea, just go build. And The thing that you want, the thing that you care about. Yeah, and not every idea within that will be a good idea, but it's a better place to sort of mine for the ideas than it is just like, generically to sit back and be like, I wonder what would be a good business and just be sort of armchair.

jack bridger (25:38.904)
you know, things. Yeah, search from your interests. I think that's a deeper place to draw from. Yeah. Yeah. On your specific kind of like the genesis of Work OS, I know, I can't remember if we spoke about it on the last one, but I know you've told me, I know you saw like company, you were working at a very famous startup, but that was like that kind of

someone else crossed the enterprise chasm, a competitor, before they did. And you were like, this is, this kind of sucks. Was it, was it always obvious? Was it, was it something that like, you just knew you had to solve this problem? Or was it like you were sat in a coffee shop? Like what problems do I care about? No, to be candid, I don't think I had it all figured out. Certainly not the scale of what I do now.

have it more kind of in clarity. I think I had just seen it as a problem. I had seen this as something that companies had to deal with, they had to build, they struggled with it, you know, themself to build in -house. Engineers didn't necessarily like working on it. Like it had all these characteristics that sort of intuitively felt right as the thing that would be valuable to build and work on. I didn't really think about how big the exact market would be.

you know, or try to think about it from a like mathematical perspective, maybe. I was like, it seems valuable for the world. I know some early people I could sell it to. Those people are people I like. I enjoy talking to them. And it's kind of this problem that like feels really gnarly. Just it's like, no one's really solved this in a way. There's not any good alternatives. It's just a snake pit of

of technology and I was like, that seems like valuable, you know? And so that was kind of the genesis to go after it and the idea formed from that, from those like primitives. But as I realized the power of like the building for enterprise and going on market and what these capabilities actually do to your company when you add them, it just kind of felt more and more special. And I realized like there was more and more opportunity to help people.

jack bridger (28:06.414)
And that's when I decided to raise more money and go faster and kind of scale it up. But you only have part of the picture in focus. Sometimes it feels a little bit like, remember in the 90s with internet, where early 2000s, late 90s, where you would load a page and the image would come in and it would load? I think it was like, was it like the?

I think it was like a JPEG encode where it wouldn't just load top to bottom. It would load like a few lines horizontally and then like another few lines. And so you would kind of be able to see like the picture slowly as it came in. It's kind of like that. Like you kind of have an idea with what the shape is, but it takes a while to get the full image picture in there. And I think there's kind of similarities to as the company develops what, yeah, what the business looks like. Yeah. I don't pretend to be like clairvoyance or had it.

figured out from day one or knowing WorkQuest is going to grow into what it is today. I still pinch myself a lot of mornings. I'm like, wow, it's really working. It's a real business. Yeah, it's good to know that even someone that has a very, very clear vision now, it wasn't always clear. Well, I heard. I think about this really often, actually. Years and years ago, I was at Stripes office. One of the ones I was.

was in San Francisco, was a pioneer building. I opened it and I moved into it later. So this must have been in like, man, it must have been in like 2013 or something, maybe 2014. And I remember like hanging out there, they were having like a holiday party and I was talking to Patrick and I was like, Patrick, congrats on all the success. Like I'd met him when he was at MIT. And I was like, it's been really cool to see how Stripe has grown over the last few years. And he looked at me kind of sheepishly. He was like, well we just, we haven't screwed it up yet.

And I just think about that all the time, how success, I mean, he was being very humble. They've done a lot of amazing stuff, that's right. But it's true that a large amount of success is once you get it, once you're in the pocket, just not screwing it up, not totally messing it up and just holding on for as long as you can and trying to keep the most important thing the most important thing at the company and just stay focused and stay true to your principles.

jack bridger (30:28.258)
Yeah, and Stripe's obviously grown, I don't mean to diminish their accomplishments by that statement from Patrick, but I do think a lot of companies kind of get over their skis or get ahead of themselves a little bit too much or make the wrong decisions and that leads to them kind of creating their own demise versus it being an external pressure. So much of a success, think, for companies that have raised money. It's like, if you can just focus on not screwing it up.

Just every day wake up and be like, today will not be the day I screw it up. That's so funny. You can compound towards success. And I should say also, the screw ups are small. It's not one day that the company ends, hopefully, some catastrophic thing. I think it's a million small things. It's like making the wrong hiring decision or not letting somebody go when you know it's not the right fit, not doing it quickly, compromising your...

Your product red map for a big customer that's gonna pull you in a different direction Shipping if you care about quality being like yeah, but the engineers really want to get this out and okay We're just gonna ship we'll fix it later. We'll fix you know There's some small things like that where each individual piece doesn't actually kill you but in aggregate They can really hurt so it's it's sort of like you know, it's either death by a thousand cuts or success by like You know a thousand small wins That's that's what it feels like to me at this

at this date. that's okay. So don't screw it up and avoid the small tiny cuts of screwing it up. Yeah. One of the things I wanted to ask you about that I've been kind of thinking about is, sorry, that definitely just moved is I know you've you're a solo founder.

And I think I would say the majority of people I speak to on Scaning DevTools have at least one co -founder. And YC encourage you to find co -founders, but there are obviously tons of successful founders that aren't. And you're a big example of that. wonder if you... But I think you've also, your previous startup, you did have co -founders. That's right. Yeah. So could you talk a bit about like...

jack bridger (32:51.808)
any advice you have whether people should just go ahead if they don't have a co -founder, if they should look for a co -founder? Yeah, that's a question. Yeah, it's hard for me to say. I've kind of done it both ways. I think my experience with Work OS has been a lot more successful in terms of our product and company growth and all of that. But also, it's a totally different product in a totally different market.

I've learned a ton to the first company is very different. So you can't really compare it, know, apples to apples between the between the two. Having co founders is great. I know a lot of people that have have excellent co founders and even companies where, you know, they swap off like, who's the CEO, like what were one person leaves and the other co founder becomes a CEO, that's a thing. There's also companies where

Later on, other people get called co -founders. I don't know if you've seen this in the wild, where they didn't actually start the company, but then they somehow get the title co -founder. That happens. So it's all over the place. I think at the end of the day, the question is, who are the people you can work with and collaborate really well with? And who are the people you can really trust and actually be able to share responsibility?

Because there's a lot responsibility, there's a lot to do. Unfortunately, a common thing with a lot of startups is like you'll have a group of co -founders and then not all of them will become leaders in the company in terms of actually building teams and hiring and growing the organization. And it's really tough to square later if you have somebody who was a co -founder but just wants to write code as an engineer and another person that's a co -founder is like managing half the company. And the responsibility gap changes and those people end up leaving. So I've seen a lot of examples where

the equity mismatch ends up actually coming out in terms of co -founders and their leadership. Some people have talked about fixing this with longer vesting cycles or things like that. in the reality is at the very, very beginning of the company, the roles aren't very defined. And then as the company grows in scales, roles change a lot. And for some people, that's very different than others.

jack bridger (35:02.55)
Yeah, kind of you were talking about like the writing the code and stuff. A very tactical question. If you're building like a tech, like Work OS, right? It's a technically very complex product. As a solo founder, that's, even if you were just writing all the code.

I can imagine that's more than one person's job to get the MVP. I wonder how you thought about allocating your time at the beginning, you're writing code, or where you're just someone else is writing the code, and you're talking to a customer, talking to users. Yeah, I pretty much wrote code exclusively up until I raised the seed round for Work OS.

And I was just working on it by myself, kind of ideas and trying to figure out. And at that point, I started hiring the engineering team. And then I was spending more time doing like recruiting, essentially early sales, product development, and sort of more like technical writing. Like I wrote our documentation and stuff like that. But I wasn't writing like all day, every day, like production code in the system.

I'm a little bit of an odd duck in the sense that I have a very technical background and worked as a software engineer. I've built probably 20 or 30 different products. I used to do a bunch of contract work, did a bunch of iOS work, web engineering. I have a CS degree from MIT. And I've learned the business side through just building companies and stuff.

Work OS is like the perfect hyperproduct for me to work on because it has this technical depth and matches my interest. But I think if it's someone that you're thinking about starting a technology company and you're not really a technologist, you probably need somebody as a co -founder to represent that. It's really tough to build a software company, a technology company where you're going to outsource the technology development to a third party or agency or something like that. You can maybe do it for the first version but.

jack bridger (37:05.77)
It ends up not being a long -term solution, it seems out there. And do you, like today, would you say you're the, are you still like the kind of technology leader within the company? Or is it like, I guess the question is like, do you need a founder who's like the very top of the chain in terms of tech, or you can hire like It's a good question. Yeah, there's different, there's different strategies at different companies. You know, like Apple doesn't have a CTO.

They don't have a chief technology officer. They're a technology company. Everybody is technical. Stripe does have a CTO, but they did also very, very early on. That's a role that they had in the company at the beginning. And so I think it's very company specific, what you need. If you're Pepsi, if you're making soda, maybe you do need a CTO for running IT. But maybe the CTO of Pepsi is not as the most important role compared to the chief.

I don't know, manufacturing officer or something like to financial officer, right? About the margins on the product you're making. So I think it's different. It's different for every company. You know, it's the same thing at WorkOS. Our engineers shape products and like do design work and actually build things end to end. You end up wearing a lot of hats. So titles don't really matter, you know, early on at the beginning. But I think the what I have seen as a mistake, maybe I'll just say this is like you start a company, there's like four co -founders.

And then everyone is like chief something officer. Like, because they just want to come up with titles like that. And then as the company scales, like those things don't matter. And then, you know, you have, you have a CTO that is like not running the engineering team. And then you have a CFO maybe who like has never done startup finance before or never done any finance. So it's great to start a company with other people, but I think.

If you're gonna do that, you constantly need to be talking about how your role is evolving and what the company's needs are and where to augment yourself with skills. What are the skills that you're missing? What would be ideal to hire? What are the gaps that you have? And be real about that. And it doesn't get easier, because as you succeed, people reach their limit and can't, the company's needs grow faster than an individual's ability to learn more of themselves and transform.

jack bridger (39:31.15)
The only way to get through that is to have kind of difficult conversations, be like, hey, this isn't working, or we need someone else to do this, or, I love you buddy, but.

we can't have you doing the books or like, you know, your random uncle doing our startup books. don't me doing the books. Like, let's go find a professional. Yeah. And that's constantly happening as a company, a company is growing. So we don't, we don't have a CTO at WorkOS today. We might in the future. We have a great engineering team though. And like really, really amazing talent that is able to shape our product direction. Yeah. I'm really lucky to work with those folks. Yeah. On those kind of like difficult decisions.

Do you have any, I don't want to use the word framework. Do you have any advice on making tough decisions? Generally, if a conversation scares you, if you're hesitant to do it, it's something that probably needs to be done. If you're feeling anxious or nervous about it, or if you're avoiding it, you're procrastinating doing it.

That feeling means you gotta do it. You gotta do it. If you don't, whether it's a person whose performance you need to correct or maybe let them go. Like sometimes people have like a savior mentality, like, I'm gonna give them every shot possible and then only at the very end will I let them go. Just like being problem avoidant or conflict avoidant. I see this happen with a lot of folks.

It's really tough. It's really tough. Because most people are not seeking conflict. They're not looking for that. so it's natural that they would try to avoid it. developing the skill that at the first instance of that, you're able to understand maybe why you're avoiding it and literally just reach out with the person and have the conversation. I don't have any framework for it. One trick that I have.

jack bridger (41:33.586)
is, and it sounds simple, but it sounds silly, but at the beginning of it, you just say like, this is gonna be a tough conversation. You just literally just say that to them and yourself. And it just sort of like prepares the room, you know, if you're like, and you can say that before you fire somebody, you can say that before delivering some critical feedback, just to kind of like make sure that they hear it also, be like, hey, this is.

This is going to be bit of an uncomfortable conversation, but there's something really, really important I want to talk with you about. So I want to make sure I have your attention. I can talk about it for a few minutes. I think that just brings a little bit more seriousness to it. But it's tough. It's definitely a maturity type of thing. I think firing people is one of the hardest things to do, to learn how to do.

It's awful. mean, it's like, I remember the first time I did it, it was like getting kicked in the stomach. I went and threw up later that day. I just was like physically ill from it. And yet it's the thing that like as a company grows and scales, even if you make the best hiring decisions in the world, like the needs of the organization just change. just inherently, there's some changes you're gonna need to make. And so the sooner that you can learn to have those uncomfortable conversations or sort of difficult conversations, I think.

the better you'll be able to actually make corrective action, whether it's firing somebody or killing a product, telling your team, like, hey, this thing that we've been doing is not working. We need to change direction. Because if you're the founder or you're the CEO and you're unwilling to say that or have that conversation, guarantee no one else is going to be willing to do it. They look to you for the ability to have that tough conversation.

Yeah, this is actually really, really great to hear actually. I think something that we've not spoken enough about on the podcast, think, and I feel like in the small in the experiences I've had, like been so many times where it's like those are those always those difficult conversations felt like the defining times and like also in like personal life and everything. It's like it makes such a big impact on your life and getting probably those right and not.

jack bridger (43:49.43)
As you said, I relate a lot to what you said about like, if it feels scary and you keep thinking about it and you keep thinking, my God, that's scary. You usually know that's the right thing to do. You just don't want to do it. And every day you don't do it is just suffering. It's just holding onto this like, know, burning red hot marble in your hand or something. Sometimes if it's feedback that you're just, you're scared to give somebody because you think they're going to blow up or they're not going to be able to receive it. Sometimes you give you feedback and the person's like,

OK. I totally didn't know. Thank you so much for telling me. Thank you so much for that. And you're like, I should have done that a week ago. I've been pulling my hair out, like anticipating the pain around doing this. Well, they're like, you know, you're actually right. And also, I have a similar piece of feedback for you. Being able to learn how to ask for feedback as well as giving feedback, giving feedback very quickly when it happens, being very immediate and direct.

I think these are characteristics of well -functioning teams. If you're not doing that and people don't know where they stand or you give them feedback, you know the whole like shit sandwich, ever heard that? Compliment, feedback, compliment. Really that only works on people that are really junior where their ego gets in the way of them hearing feedback. If you try to do that to somebody who's more experienced in their career, they're like, cut the crap. Just tell me, they just wanna know. They just wanna do better at whatever it is in their job or in their role.

But it's tough. It's definitely a thing to learn. I think it's I've certainly gotten, I think, better at doing that. I certainly do it faster. Whenever I see things, like, let's talk about it. Maybe not make a decision, but I at least want to make sure we're talking about it as early as possible. Yeah. I have one more question that's just kind of like a sort of left field. But I think it's like I.

It seems like you're doing a lot of the right things as like the CEO, like, you're very like, you know, you are the CEO, you're a founder. Hypothetically, if you have to like, you're like, you're forcibly going on vacation for like a year or two, and you have to like hire like replacement Michael. What kind of like traits and characteristics are you looking for, for someone that you think it's gonna, it's gonna be in a better place?

jack bridger (46:09.272)
when you come back and Work OS would be in a better place in two years? that's a good question. Yeah. Gosh, that's a great question. I I think about this pretty frequently as I'm building out the leadership team or hiring other people into the organization. Who will have the skills to augment me? Where are my weaknesses or areas that I haven't grown as fast as I need to?

In a startup, if you're the CEO, you actually have the very unique job where you're allowed to be bad at your job. You're allowed to be bad at it. I'm allowed to be a bad chief marketing officer or a bad chief financial officer. I can't commit fraud or something like that, but I'm allowed to step into those roles and bootstrap them and spin them up to learn enough to be able to go hire those people.

So there's a whole ton of areas at WorkOS where I could hire people that could be so much better than me. Pretty much all those areas, I would say. At this point, pretty much everything. And then I think to your question as well, if I was gonna be gone for a year or two, what would I try to do in advance? It's the stuff I've already been trying to do. It's like set up the organization to succeed.

Not around specific products that we've been building or specific features that we've been shipping, but more from the perspective of what are the values we have, what are the ways in which we operate, how do people get feedback, what are the kind of rituals we have as a team? Those last. At WorkOS, we've done a company all hands every single Friday since the beginning. That's not gonna stop if I was gone. I would assume not. It's just kind of built into the company.

So I mean, if I was gone for year, I actually don't think the thing would fall apart today. It might not transform in the way that I'm working on right now. Like I'm always trying to change it. I'm like...

jack bridger (48:12.782)
Like I, yeah, let's look at what I say. That's like the idea of the company that I have in my head is the company as I want it to be six to 12 months from now. And I'm working to sculpt it in that direction. I realized this actually about my job a few years ago that my job is actually not really to manage operations as it stands today. I need to make sure that happens. I need to hire really great people that can do that and execute on, you know, what we're achieving with customers and what we're building and all of that and how we're shipping stuff day to day, week to week.

and I need to keep them accountable and make sure it happens. But in terms of my job job, I think it's to grow the company, to evolve and change it.

I have a pretty specific vision for what that is and what I want it to turn into. I think it'd be very hard for me to find somebody else that could do that. So my guess is if it was like a year or two I was gone, it'd probably keep growing at the clip it is and doing well, but it might not turn into this thing in my head. Well, just this thing in my head, which is like the Work OS 2 .0 or 3 .0 or whatever it is. it's like the vision. Yeah, the vision of what it's going to turn into. And I think that's very hard.

It's just very hard for non -founders to do that because you haven't been thinking for it as long. But I have a great team. I think that's the thing. It's probably the thing I'm the most proud of at the company is not just products we build, to the customers we have. It's like the team we've put together and how they operate. It's the best part of the job. Yeah, they seem great, the people I've met today. Yeah, they're excellent. A few of them are back there. Yeah, that's so cool. just from, I did a startup.

a few years ago with my friends and we spent like one year, seven days a week sleeping in the same little apartment, working all the time. And we got some customers and it was just so hard. Everything was hard. And then we kind of stopped doing that. We kept it part time and it was so shocking to me how easy it was to maintain the existing stuff that we had. And people just kept coming back and we were putting like less than 10 % of...

jack bridger (50:19.342)
the effort in and it would just maintain. And it was like, okay, it's because it's just so hard to actually like accelerate and grow. But it's like, compared to that, the maintenance is like, quite easy. I don't know if that is like - things have inertia. Once they start working, they kind of compound and keep working. And then it's very hard to disrupt them. You know, the whole thing about, you've probably heard like a product needs to be 10 times better to be disruptive.

not just twice as good, or three times as good, 10 times better. If you go to a customer and you say, we can make it twice as good, would you switch? People actually say yes. We can make it half the price you guys are paying. Would you consider switching? yeah, 50 % off? Absolutely. But in practice, it's not enough. In practice, it actually needs to be 10 times better because there's so much inertial,

know, headwinds around it. It's so hard to change anything that it actually needs to be not just a little bit better, but an enormous amount better to overcome all of that kind of like legacy, you know, experience. And I think that's what you're kind of suggesting. There's like one things are working. They'll get to compound, you know, when they do get disrupted eventually.

It usually doesn't happen overnight as well. There's still people running IBM mainframe systems that are out there for decades. I even have this pet theory that the way to do disruption is actually not to go after existing things that have been built, but it's just to build the next thing, the next layer. It's way easier just to go capture a new market.

than it is to try to disrupt. Everyone tries to go and disrupt existing markets because there's there's money there, there's a budget, there's all this stuff that's already been built out. But I think it's way, way, way harder. A new market is smaller, but if you can capture it and it can compound and grow, that can be actually a growth avenue for you versus, you know, it's like trying to redo the foundation on a skyscraper, you know, it's like, it's just enormously complex to do something like that.

jack bridger (52:36.076)
Yeah, so it's like the Netflix blockbuster. Don't compete with Blockbuster on video. Over the top. Or think about things like WhatsApp competing with SMS on phones. It's just completely circumvented it. Didn't even compete on that front. Yeah, that makes sense. Actually, one more question is, so you're disrupting yourself as well, alas. But now I think you're starting to become big enough that there's like,

of startups that are trying to go after Work OS in a sense of like, how do you think about that? Yeah, man. People started running keywords. People started buying the Work OS keyword on Google. I was like, OK. Yeah, think if you have any kind of meaningful success, you'll have competitors. mean, it's just the way it works. And I don't really worry about it too much. I think there's like two things. The world of cloud and like,

software is just so huge. It's so, huge that more often than not, you don't collide. Like it's not zero sum between companies. Sometimes it does though. Sometimes you do have competitors in the markets. But I do think that you can't like drive a car like looking in the rear view mirror. Like you have to have all of your attention looking forward. You you can't be just, you know, glancing behind you.

especially if you're driving really fast and trying to be going as most extreme as you can. So yeah, we look at what other people build sometimes. In the Auth and Identity space, there's so many companies now building this. I mean, it's kind of wild. It's like every month there's like a new one. It's kind of cool. I think it's still like people say like the biggest competitor is still just like people doing it themselves, though, I guess. Totally. Yeah.

The question of should you roll your own off, it's wonderful. Yeah, it's like the age -old question. I feel like it's like the tabs or spaces of like modern front -end app development. There's always like big, I mean, just this week, I think there was like whole THH figure. I love it. Yeah, yeah, yeah. If you want to troll people on Twitter, just put that question on. It's like tabs or spaces, or should designers code, or should you roll your own off? It's like an evergreen.

jack bridger (55:02.562)
online debate. But auth is just one part of Work OS. It's not the only thing we have, cooking. Yeah. That's awesome. Yeah, Michael, I think that was all of my questions, actually. Yeah. It's a place to up. Yeah. So if people want to learn more about Work OS. Yeah. WorkOS .com. course, you can find me on Twitter. And.

Yeah, follow along for our, we're calling it the Enterprise Ready Conference. Enterprise Ready Conference. Yeah, if you're interested in coming, send me a DM. We're going to send out some invites in the next few weeks. It's going to be really good. Yeah, it'll be in October, end of October. I know you're going back to the UK pretty soon. We'll be excited to wait for your next visit out here. Yes, absolutely. Thank you. Cool. Thanks everyone for listening.