Inside Decagon: Finding PMF, Hiring Fast, and Scaling 10x

open space is like very very undervalued and this is this office is our first office out of all of our offices that's more of a donut shape because it's like you know high rise and just like you know when you're on one side you don't really see the people on the other side as much you can't really tell when people are eating food and um yeah so the new one is like one big like rectangle where you can like see everything yeah this is 500 people in one rectangle come on yeah that's the goal yeah good man well congrats on everything i'm excited to do this in the beginning when you were were you not um unnerved to be hiring ahead of like okay like in the beginning of decagon you know whatever 18 months ago you were like eight people 10 people right okay and like you felt demand yeah like the market was beating you down and you were like all right great i got to go hire a bunch of people across all these roles was it uh not unnerving in any way to like hire ahead I'm dead.

It was a bit. I mean, I think, like, now in hindsight, you're like, yeah, I should have hired more. Like, obviously, like, the demand was there. These customers are going to close. But you didn't know that then. I actually think we've, for the first year and a half, we were, we took a very conservative approach to hiring. So we didn't really hire ahead. We only hired someone when we actually felt the pain of, okay, like, we need someone doing this. That went for sales as well. I mean, you know, in the beginning, Ashman and I were doing all the sales. And eventually, when we hired our first salespeople, it was like we already had deals for them. So we didn't really have hire ahead. So we didn't really have that concern. I think in hindsight, you could maybe say that was a mistake where, okay, you know, in hindsight, this is such a great market. There's like so much to do here. Like maybe we should have just hired ahead.

but when you're in the moment when you're in the moment to your point you don't really want to hire ahead because you know you have all these stories of companies that hired ahead and like that worked out disastrously and then you have the fire people so for us we've always kind of taken a pretty conservative approach with building the team and like keeping it lean now of course we do hire ahead just because you have to you have to like plan out like where you because otherwise you just cannot like reactively hire this many people and things are going to break so we do hire ahead now but for the first year like first 100 people i don't really think we did too much ahead you said the first 18 months you felt like you didn't hire ahead for too much yeah like how many people were you at first 18 months not that many like maybe 50 people 50 60 people yeah we pretty much 10x the team last year we're 500 now 500 yeah you were 50 roughly a year ago something like that yeah 500 yeah come on so you don't know everybody's name in the company anymore no i'm actually pretty good with names but uh that probably stopped around 200 ish people okay yeah 500 yeah i mean we're not all in sf anymore so we have a bunch of different offices

like sales yeah sales are remote we have a big hub in new york in london when did you break the when did you relent on not hiring in in office anymore it's probably our first couple like sort of strategic salespeople because, you know, we found people that we thought were really good and we realized that, you know, these people are not, they're going to be traveling a lot anyways. Yeah. So we'll just have them be in the office when they travel here and then the rest of the time they're just traveling around meeting customers. That's pretty common for teams, I think. It's like it's, you're not always going to have all your salespeople in one office.

That also kind of defeats the purpose. And then we started the New York office, I want to say, roughly nine months ago. And so that office is, we're already on our third office there. Come on. In hindsight, maybe we did not do a good job of planning offices, but yeah, we were constantly just like overflowing. It's a pain in the butt to move offices. Yeah. And they're only like dealing with the lease, the furniture. Yeah. Just like things all the time. I mean, you're not dealing with it anymore, but it's just things. Yeah. I mean, your first office could be like a WeWork or something. That's not too bad.

Right. yeah we just moved into our new new york office and we like it a lot and again it's like that big rectangle so we're a big fan of the rectangles the vibe's just nice how often are you going there now to like get it up and running or did you go there to get it up and running uh pretty frequently i go to new york like at least every month pretty much how much more are you traveling now that the business has taken a scaled tone if you will yeah i do travel a lot um i don't really like traveling but you know it's part of my job so traveling is usually not that bad the international trips are the tricky ones so we announced we opened up australia so going there is like kind of rough and you have to go um i i was out there for the sort of launch of the office okay and then i go to Europe?

A decent amount, so maybe quarterly. For customer meetings? Yeah. And we have our office there. We have like 50 people there now. And yeah, you just got to see the team. Like last time I was there, like before the previous time, we had maybe 12 people. So now all the new people, they onboard in the US, but I haven't met a lot of them. And so it was important for me to go and just like meet the people. We have a good team getting built out there. And yeah, Europe's also tough because it's not even just the time zone it's like uh oh it's 12 it's like midnight and actually there's still a ton of calls or there's still a ton of stuff to do because it's it's like i don't know afternoon here so um that that's the tough part with traveling but i'm getting a little bit more adjusted to it why don't you like traveling generally i've never liked traveling ever i don't like traveling for fun i just don't i just like being at home yeah home is comfortable and i don't like sitting on planes i don't like sitting in cars i don't like walking long distances. Really? Yeah, it's kind of funny, but I just don't like it. I guess it feels like a waste of time to you? I guess, yeah. It's just not physically pleasant either. It's like being

in a nice air-conditioned room doing what I want to do. My wife's a lot more into traveling, so we kind of go to the places that she wants to go to. We just came back from the Dolomites for july 4th yeah how long are you there for uh just july 4th like that weekend sweet yeah do you feel guilty when you go travel not really um you mean as in like oh i should be doing work yeah i mean i do work when i travel but also it's it's also not super responsible to like be burning yeah full force every single day yeah but you could still know that and still feel guilty i think maybe i did at some point i don't feel guilty anymore yeah that's like there's like people yeah yeah and we also have a skilled team now that are all hard workers so that's what i mean you have like leverage it doesn't feel like yeah if i go to sleep that no one's pushing in the 10x of the people from 50 to 50 to 500 yeah that's insane by the way like that's that means you're doing conservatively about probably 2,000 interviews. Does that feel right?

We've maybe done more than that. That's what I mean, conservatively. Yeah, but it's split across the team, so the team does spend a lot of time interviewing. That's fine, but your company is doing 2,000 plus interviews. Over, over, definitely over. You're not hiring more than one in four. I mean, that's just what you have to do. There's no way around it. i mean there are companies out there they're growing faster than us headcount wise you know it's like everyone's growing fast the the hard part is not so much hiring the people because there's a lot of people that want to work in you know high ai companies it's making sure you're you keep your bar high so one of the things we do is um like revolute does this amazon has a

Jesse Zhangversion of this you you kind of have these like filters that you add on to the interview process at the end bar raisers or whatever you want to call them where they're just mostly selecting

for culture and you know intensity and so on and we've added those to you know make sure that we keep the bar very high as we grow did you add that like when you're gearing up to go from 50 to 500 basically pretty much yeah and who's the bar raiser you um oh it was me and ashwin for a long time we met everyone up until maybe like 300 people now we don't meet everyone but now there's like you know some fraction of the company that's been here a while and we think are very good representations of the culture and so they do these bar raising interviews what percentage of people make it past or don't make it past the bar raising uh i don't have a super do you have like a sense i mean it's definitely the majority of people make it past.

Because it's the last step in the process. If you're cutting the majority of people at the last step of the process, that's probably something wrong. I don't know the exact number, though. It's definitely a majority. When you add people that quickly, how often are you having to basically reinvent every new process inside the company? How quickly do you have to tear down a set of meetings, add a new set of meetings? Yeah, pretty quickly. I mean, it does feel like kind of a new company every quarter or two, roughly. and i mean this is my first time or ashley and i both first time you know doing company of the size and so there are sort of some learning some mistakes we make and we're just trying to do our best to iterate there are also some benefits on doing the first doing it for the first time because you're a little bit naive in a good way it's kind of the same thing with founding a company like you're a little bit naive around how hard things are and so you actually have optimism and so there are some things we've we you try to do differently just from first principles but um yeah in general the team is structured you know kind of just based on like iterative like an iterative process as we

grow yeah my my observation like in kp with founders is like even if you've done it before you've never done this meaning like if you're arvind at glean you like started a rubric yeah but like okay glean at this size and scale with this like technology wave with like the set of variables that are on the field today he's like never done this you know like benioff has never done this in this oh yeah sure you know what i mean and so i don't know i think in many ways everyone's kind of making it up yeah and i think that has always given me solace that's a good perspective actually yeah that's that's pretty true you know like um even your fiercest rival like at sierra brett who's a stud like i love brett he's making it up like he has never been for all of the things that he has accomplished he's never been at a company in this market in this time at this scale yeah growing this fast just never happened yeah and uh so the type of competition the type of like you know sales cycles are also different and so everyone's learning i agree that's what i mean yeah it's like a new pricing model like it's all different yeah for sure um like how relevant really was your last company you sold it to niantic

right oh zero relevance zero um the only i think the only relevance is like it just teaches you learnings as you mature right so um that company i was solo founder which i didn't like so that was learning um and so with osha it's like 10x easier and you kind of you kind of have to get lucky finding a co-founder but um we're also remote because it was during covid i was also learning i didn't like that so now we're in person and uh it was also a consumer app so very different and i also i think learning there is consumer is very different from you know b2b and i just gravitate towards b2b a bit more just like mentally so those are the types of learnings that you get and you kind of also learn like intuition of how to evaluate if like an idea is

Jesse Zhanga waste of time or not there's like stuff like that but in terms of like tactically like how to lead a team how to like you know run a company almost zero learning so most of those things you

just pick up along the way or you try to learn from like people that are doing it a year ahead you know yeah i guess like let's just imagine that was like a b2b sas company i'm still not convinced that you would have learned that much i agree does that make sense because everything's faster now in fact you might have learned some bad bad habits yeah exactly so um so anyway maybe if you hit your head hits the pillow tonight and you're like oh my god what's happening you're like well most people feel that way yeah yeah that's true why don't you like why didn't you like besides the obvious like it's lonely why didn't you like doing the solo founder thing Um, I think it's two things. Like one is the psychological piece, right? It's, you know, you feel like you're like a single point of failure for a lot of things. Um, regardless of how big your team is, it's like, uh, uh, like you're the only one that has like the founder responsibility and context. And so, I mean, yeah, tons of respect for a solo founders, but it's just very difficult. And the second one is that you don't really have someone with the same level of like context and commitment to bounce ideas off of.

and so a lot of ideation just takes a lot longer like i think if i have just anyone on our team if we're just like talking out loud and speaking you you arrive at decisions and like probably correct decisions way faster because you're just kind of like just kind of like another brain or another like processing unit now you can actually do some of this with uh clod which is kind of interesting you can use as it's about ideas but it just gives you like a talking like a a way to vocalize ideas and like kind of hear feedback and you kind of eliminate bad ideas really quickly whereas when you're alone and you're seeing your own thoughts it just takes way longer to arrive at ideas that's the other learning i had so i was listening to i read or listened to something that ashwin did where your co-founder yeah where he was talking about in the beginning uh you guys were in every day yep the two of you yeah that changed at some point or maybe you still in every day when did you stop asking the team to be in every day and was that like uh weird was it hard like did you feel like you were degrading performance oh uh interesting so asha and i are always in every day i mean we're not we're in every day except for saturday

saturday is like wife day sacred you have to uh have to have one day at least uh but we're in every day wife day yeah do whatever but don't do work just hang out exactly yeah and the i think early on yeah people would come in on sundays as well we never um had expectation for people to come out on sundays like it was never like when you hey like you're joining this job like you're gonna have to come in on sunday you know we're also okay with people like having lives and um not being on sundays but yeah around maybe 20 to 30 people it's like not everyone's going to be in every Sunday um now we still have like you know roughly that size of people that come in on Sundays but it's most people are just doing work they're just not in the office totally um because Sundays is a great time there's no meetings you can just like you know get your thoughts in order and catch up on stuff so people like that um so Sunday is kind of like a pseudo work day but again there's like zero expectation like no one's expecting you to respond on Sunday and it wasn't like a single time where that happened and kind of it was just kind of like a spectrum right like when you're hundreds of people not everyone's gonna come on a Sunday

like that's just that's not gonna be reasonable but people are just you know thinking about stuff and uh yeah now it's a pretty good balance I mean we're in on Sundays just because I live super close to the office and so we just go in and there's a group of people that come in and um it's a good time to get some deeper work done are you enjoying it more or less than you did in the beginning like realistically the job today is like you're traveling a lot like i think it's one of those things where it's like uh you know when you're when you're little you're short and at some point you like get tall but like no day does it feel like oh i was taller than i was yesterday it just feels like you're the same that's kind of what it feels like like i would say from the early days now it hasn't the feeling hasn't really changed that much i would say the only time it does change is like like when you're in the idea maze to like maybe post pmf and you're scaling like that is a pretty different feeling and i think no matter what anyone says the the early like zero to one phase is like way more way harder it's awful yeah so yeah every stage has it's challenges about the zero to one phase is like by far the hardest once you're past that phase

at least in my experience the general feeling is the same like the stuff you're doing is different but like you know it's enjoyable you know it's like kind of a privilege to be in a fast-growing company or have like this is even though like every day is not easy it's like you know this is what we wanted to do and so you have to be a bit thankful that you know this is um you know things are going well and you know i had my last company as well where like i was in that zero that first phase for like forever how long uh like three years maybe come on um well i was yeah i was a new grad i was like 20 at the time and i like so when you're a new grad you're like super fresh you you probably think you're like i mean we thought we were like quite smart and very technically strong whatever but you just like don't really know how to do stuff yeah so we like spent a bunch of time like working super hard on stuff that was like okay we just thought about this for a few for a little bit more it's like you could tell this is a bad idea uh and now yeah so that phase is just much tougher and so now because i have that perspective it's like it's easy to have appreciation for when you're not doing that you know how long were you in the

idea maze for dacagon like three weeks come on yeah so we um we arrived uh maybe a bit longer than that but it's like rough rough order of magnitude it was very fast because we our main goal when starting the company was like let's not be in the idea base you know that sucks

Jesse Zhangso instead of picking idea we just um we were like very aggressive about doing this like almost like sales discovery i talked about this before but like i think most founders shy away from being

as aggressive as you need to be in that phase because it feels like you're being too pushy or too salesy but no one really cares about that like your your founder starting a new company like they'll appreciate if you're asking like more tough questions like you know how much how much we pay for this you know where's the budget coming from like how do you justify ROI internally like who are the people involved like those are people those are questions that like a salesperson should ask in like a sales cycle but early on founders tend to not do that and they're just doing things like would you use this like you know yeah how useful that would this be for you and like if you're not asking the hard questions it's hard to tell so i think through that process we decided like hey this is like the obvious thing to build and that was in hindsight helpful i mean you have to be a bit lucky obviously but i think that process helped us avoid a super drawn out initial phase how long before you raised your first round well technically we raised our seed round like before Asha and I started working, like we decided like, hey, let's be co-founders and then we hadn't even incorporated yet and we had like zero ideas.

But then we just raised a small seed round from A6 and C. That was before we had anything. That's nice. It is, yeah. I mean, yeah, people have different perspectives on seed rounds. I think for us, it was like, yeah, definitely the right choice. I mean, I think everyone in our seed has been like a great partner for us. It's just any, inch of credibility that you otherwise wouldn't get at that point yeah it's worth it yeah like people often ask me like what do you optimize in the early investors i think like no investor will help you find pmf faster like that that's like not an expectation like no matter how good the investor is so the only thing that you can ask from them is like like one first of all like don't be a negative impact um but then two just be like emotional like just like emotionally supportive and help with like help hustle for like introductions and stuff like that introductions to hires and introductions to customers but like no one's gonna in fact when we were first deciding to do this most of our investors and like some very smart like you know founders we knew were like no don't do this this is a dumb idea because it's too obvious um i mean in hindsight like obviously

We didn't listen to them, but no one really knows. No one's going to have ideas. When people ask me for perspectives on what they're working on, no one's really going to have nearly close to the level of depth to give a credible- Of course not. You barely even know about your own business. You're figuring everything out on the fly right now. I think optimizing for mid-career investors in the early stages, I think is actually the sweet spot. Because they have the time and the sort of motivation to like really grind for you. Yeah. A lot of the super senior GPs, I think, are very good while you're scaling.

But in the early days, given that no one's going to help you find PMF anyways, you might as well get someone that has like a lot of time and like prioritizes you. Yeah. Yeah. I've taken a different approach. Yeah. But. Yeah, I mean, there's not only one approach. That's just the approach that we did. I took more of the like Avenger ring approach. Yeah. Just purely signal. yeah and then i have like the team of kp people that are amazing at helping me but i'm not relying on the board member themselves right in the same way yeah and like you know founders fund's whole thing is like we don't want it like it's anti-cycle yeah yeah yeah exactly i think they're really good investors though they're great yeah but like trey's whole thing is like you know yeah trey's whole thing is like the board meeting should be an hour you know like that type of thing yeah so true um how long did it take before you it became clear to you that you had pmf and what was the was there like an obvious like oh yeah here we go i wouldn't i don't think there was like a like a clear cliff or anything it was like a gradual yeah scale up i think maybe we were like a million in revenue it was just me and ashman then still but i think it's repeatable enough

Jesse Zhangwhere how many customers ish six okay maybe yeah six customers a million in revenue it's like okay well yeah there's a lot of people that want this people are willing to pay us real contracts

like there's probably something to be done here in hindsight i would say uh yeah there's also we're kind of lucky to choose a space i mean this space and coding maybe are like the two big ones for ai that are like very horizontal and just like very obvious maybe law use cases yeah law um those are a bit more vertical um i think there's other vertical use cases as well like law like some health care use cases but just in terms of like big horizontal like um we didn't know that going in obviously like it wasn't like we were mapping out the market and in fact i don't think it's wise to do that because that's pretty noisy but it's not like we were mapping out the market it's like okay you gotta do this but i think around that time we felt like there was product market fit and then did you raise the a right after that pretty much yeah so all of our rounds so far have been uh aggressively preempted i mean it's not always gonna be like this but we never really did a fundraise we just every round is just someone giving us a term sheet i guess and then we had to decide if we wanted to do it most of the time in the past we were pushing it off because we're pretty adverse this goes back to like generally

we've been pretty conservative about hiring we've also been very conservative about fundraising because i mean there's so many like instances where you raise too high of a valuation and then oh well you know there's like cycles you know it's like it's not always going to be super easy and super you know hot in in the market so we have always tried to push it off um but yeah i mean there's some there's obviously some benefits of raising uh in the early days raising gives you validation gives you sort of more people around the table well after a certain point though i think there's diminishing returns of that and like raising mostly helps you just like reprice your equity if you're hiring really fast then like maybe Higher valuation helps with that because people just, people shouldn't do this, but pretty much everyone just takes the dollar value of your equity.

So that's why. And it's like kind of a marketing event, right? Yeah, it's a good marketing event. Yeah, I think like one thing you could do is just like raise small rounds more frequently. Yeah. Like Ramp does this very well, for example. Yeah. Because every time you raise, you could announce something and it's like something that a lot of people will guarantee you to read. So you just put some messaging in there. Totally. good for you do you have a perspective on getting to know investors versus not uh yeah uh you mean like ahead of the raise yeah ahead of the raise because they're all reaching out to you like your inbox has been and will be flooded with them oh yeah i think you should definitely get to know them even even if the sole purpose is just like you can gauge how helpful they'll be so like no one no investor will ever be as helpful as during that like phase where they're trying to close a deal because like you're like their sole focus they're like super incentivized to help so if you ask them for help then and they're not that helpful then you know that they're not going to be that helpful when they're on your cap too so you can kind of just you know get to know them just be friendly just get a feel for like how you vibe with them and like if you get along with them

long term if you feel like you know there's trust and then you can ask them for introductions or help with like a problem that you're you're you're dealing with and if you feel like they're helpful then that's a really good signal um so we've done that for pretty much all of our rounds and i think that's led us to construct a very good cap table i think i think we're probably one of the companies out there if not the the single company that like leverages the cap table the most just because uh i don't know we just found it be effective and it's like a self-reinforcing loop right if someone helps you and then you close a deal and like you get to tell them and their whole team that like hey you guys like this led to like real value then that's great for them and then they'll help you more so it's self-reinforcing do you ever reach out to the investors that you want to talk to or do you just respond to the ones that reach out to you like so far it's been mostly the uh latter like people just like we respond to people that reach out because the the investing world is not not that big so like generally we know people and so i don't think there's anyone that uh we haven't met that like oh we really want to meet this

person yeah yeah were the b and the c basically back to back all the rounds were roughly like six months apart six months yeah okay which again it's not always gonna be like that so we shouldn't plan for that but six months i think is a little bit too frequent do you yeah and like all things equal they're too frequent but if you're in like the heavy growth mode like you kind of have to raise to keep the momentum going you know one of the feelings that i get deep down that makes me quite uncomfortable is that everybody how do i say this you just kind of everyone just kind of assumes like yeah the good times have been good for the last few years you just like it normalizes it just normalizes and that means like customer budget continues to like fall out of the sky that means fundraising continues to like it hasn't been that hard yeah you know i think like probably your team feels that way like it's just growing it's just you know it's growing faster than anything ever yeah you know i don't know i wonder if you like how you relate to that yeah i mean you just want to like uh have a steady mindset across everything right you can't get too high during the highs you can't get too low during the lows so you're always trying to counterbalance like we we say internally all

the time that it's not always going to be like this you do and yeah even when we do say it even though we say it we also know that like just viscerally like yeah everyone's kind of expecting just constant growth right but most businesses aren't like that like a lot of the one That are now growing fast, grew super fast during Zerp era, and then there was a couple years of roughness, and then now they're growing again. It is cyclical. We want to make sure we're talking about that. We've had very good quarters the last few quarters. When we recap the quarter, we tell everyone, hey, obviously, it's great right now. Everyone should be ready that it's not always going to be so easy.

So you got to build the toughness right now. You got to build the grit right now. And that's a message we try to make sure we emphasize. Doesn't matter, does it? Yeah. It doesn't matter. We have very few people that have sort of left the company, but we've had a few go start their own companies. and yeah maybe there is a world where like if it ever becomes harder to start your own company like that will happen less but i actually don't think i think even when there's a downturn it'll

Jesse Zhangstill be pretty easy to start a company i think the only good thing about a downturn may be that it might be easier to just recruit that's the hope yeah because there's so many companies right now

too many yeah and that's like that's a good thing for the world generally but yeah it makes recruiting very difficult and uh it's also really easy to be a founder so a lot of people a lot of people at decagon have like a very strong entrepreneurial sense like they were founders before or yeah they want to be founders and so if the barrier to entry is very low then people just do it even if they don't have an idea even if they're not sure if it's the right time yeah i was um we did a debrief on a candidate yesterday and at roadrunner there's a lot of people that that are ambitions to be founders.

Yeah. They're very spiky. And, you know, this candidate during the, like when we were talking about her, I was like, hey, this is gonna sound like a weird comment, but like, she is like a software engineer, a software engineer. This is what she loves to do. Yeah. And this is what she wants to do. And in two or three years, she just wants to be better at this craft. And I was like, you know, there's something low maintenance about that that i really like i like i don't know just like that sounds nice like you can't have a team full of those people you can't have a team full of but i'm like you know like having some people that just like love this thing i appreciate that why not get both yeah you just get both you get both but there is more maintenance with spikier people that have huge ambitions yeah there's a tax and there's obviously upside that you get with it too i think that happens across all roles so So like early days, when you're spending on anything, like the generalists are very valuable because it's like one person with all the contacts, they can do a lot of things.

As you scale, you kind of start hiring more specialists because, you know, now the functions are defined and it's like, okay, let's just get someone that's really good at this because they're going to be spending all their time doing this. And I think that that's applicable to all roles. Like I think even our sales team, our original team, was very, very, I think we got quite lucky with the team. very smart very creative like very just like self-starting and uh you cannot find like hundreds of those people so i think as we've grown we've kept the bar very high in terms of just like intelligence but now we have different personalities right like some of them are much more experienced they want to kind of come into like a playbook organization and just execute and i think that's very normal you presented to a group of 50 cios and this thing called kios that i represent for kp yeah and i was sitting next to you and you know what i thought was interesting i really want to get your reaction to this like i think Brett at Sierra was in the last one. You were at this one. I kind of like got to watch them both and see how they play out. One of the things that you, that I thought you really emphasized

was the implementation. Yeah. Like on the deployment. Yeah. And I thought you went out of your way to make a point that this was like a unique differentiation. Yeah. For how you think about your business. Is that true? And like, maybe like what's your, yeah, happy to. What's your thoughts on that um yeah maybe uh maybe i can just like zoom out contextualize everything so historically we don't really talk about competition etc just because like the space is actually like pretty noisy and there's like all these different things going on i think now is a little bit more solidified i think we're a bit more established sierra is more established and so i think we have a more clear perspective on on the two um and i think broadly like when you're building company i'm sure you relate to this like um like everyone so you you want to build a culture where like you know you're the main character right like we we just we view the world as like we're the main character there's like all these challenges and competitors that might be out there but like it doesn't really matter like we're kind of on our journey so we want to want to come up with things from first principles and like you know again like we're the main character on our journey um if i could hand select like a

competitor would i have chosen brett taylor probably not it's like if you could choose like who you're competing against like you know the ex-ceo of salesforce and cto of facebook like yeah obviously we have a lot of respect for them but that's just like that's not how life works you know life it's a very honest and true you're like uh you're on your own journey and you like challenges will come up so you have to deal with them yourself right and like that's how that's how we view it and so like you know if we're good then we should figure out a way around it so the way the way i with this like from my perspective at least this space has played out is you know you have sierra they're very good at uh getting into like enterprises and they're uh you know they've scaled their team really quickly and you know i'm sure brett is great at talking with leaders and obviously that's a skill that you know we've we've developed um but their deployment model is uh more similar to like a palantir where they they're really focused on you know forward point engineering and hey like we can do it for you or like trust us right we have really smart people and we can we can solve the problem for you end to end and uh i think our our main thesis

right and like this is again it's like not in the context of cr like when we were first starting the company our main thesis for like hey what is our viewpoint on this space is that model doesn't really make that much more sense that much sense as the ai models get better like that model makes a lot of sense where like hey you're a big enterprise you maybe don't have the talent internally to like move at that speed or like kind of do something and so working with a partner

Jesse Zhanghaving them do everything for you could be attractive but one of the main benefits of ai especially agentic ai is that it really empowers people on the team to do more and so if you think

of like cloud code or stuff like that it's like yeah you can have a non-technical people that can build a lot more now than they could before so that's like a big theme of ai right so our whole thesis is like hey can we create a deployment model where you know we're still going to be white glove because again we're working with enterprises it's never just going to be like here's software go use it so we start we still have like people that are staffed but it's more about how can we empower your team and how can we deliver a end result that is like fully in control of your team right so like everything that's get built that gets built is not code it's not like you know something that engineers have to go and configure every time or you have to ask us to come and configure it it is in the product so it's like can you build a product where the ai is fully in there it gets built it.

In the product, it's tested in the product. All the conversations that it's having, you can monitor in the product. And that's kind of the main thesis, right? It's like kind of this deployment model where, you know, ultimately the customer owns the results and the process. so yeah i mean we think that is probably a big differentiation right now right like back to the point of you know we're in a space where there's a lot of sort of defaults right like if there's all these big platforms like salesforce and google like you can use their solutions um you know maybe you know like you know brett well and and yet we're winning a lot of these big deals and so the only way we can do that is through product. And obviously, I hope they like me and they like our team, but it's like you have to build a product that is superior. And the way we've done that so far, at least, is kind of a product that really enables people to build and empowers them and makes it so that the AI is owned by them. Was there a part of the company as it grew that you feel maybe like an org or a function that you most misunderstood?

The first one that comes to mind is probably marketing. I think a lot of people probably say marketing like is so broad, right? And so fuzzy. Yeah, so fuzzy. And the people in marketing, just like in sales, are very good at marketing or selling themselves. Yeah, yes, yeah, that's a good point. Yeah, marketing, I would say, one i think we hired it a little bit slow now i think that's that goes back to one of those like the original question of like could we have hired ahead there like probably yes but it's so hard to like decide like what is the pain point for marketing i think my perspective on it has changed now i've also learned a lot more about you know the field and you know we are very strong marketers but like marketing itself is also super different right like like product marketing like kind of really being able to talk about like what you're working on is like very different from like growth and demand gen which is also very different from all like all like trying to improve your brand and uh like all like social media strategies and whatever it's just like like none of these are like very like systematic in a way where you can just like reason through everything there's like there's a little bit of art to it obviously you can you know build

systems that track everything closely. But yeah, that's probably the function that where I had to learn the most on. What hire was your first marketing person? Like what number? It was first 30 people. 30. Yeah. Okay. And what type of marketer was it? Product marketing. And do you think you should have done something different? We don't know the counterfactual, but I think product marketing has worked out for us as starting as the starting point um so ploma who's our vp marketing and uh actually came from glean yeah uh yeah i think she's she's done

Jesse Zhangvery well and i think the the thing with product marketing is because it's more amorphous that actually like fits better in your early early company because your early company is like very

amorphous so like having a product market that's just smart and can kind of like flex around like what the needs are is like good and then once you kind of get to a point where you can be more systematic and like you know do more skilled like performance marketing uh that's when it's time to have you know growth people at least that's my pov have you found it hard to prioritize your time in the right areas is the company shape shifts so much hard not really but it's definitely like a constant effort that needs to be like we constantly have to be self-reflecting on should i be spending my time on this or should i is like is there more valuable stuff that i should be working on but i wouldn't say that's like necessarily that hard I think the hard part is like forming the initial bench of like just like teammates that can do a lot of things that you would be doing and do it better than you. That's hard because in the early days, you may have no clue what you're doing. So it's like, if you have no clue what you're doing, like, how do you evaluate if someone's going to be like way better at you than this and like also be world class. But once the team starts forming, that becomes easier.

how did you and your co-founder meet uh we had a lot of mutuals before so um i knew one of his his previous co-founders um who's now one of the founders of cognition and we yeah we met just through mutual friends and we officially like started chatting about um working on a company at a uh andreason horowitz offsite got it yeah and do you feel like dumb luck like you got lucky uh in terms of finding a co-founder yeah that you like yeah actually like like you know it is very luck based i would say but it's not that dissimilar to like finding a spouse you just have to like it's like right person right time you just like if you have enough shots like opportunities then like hopefully someone fits but yeah but that's like very contrary to popular belief like you know at yc they tell you like you know make sure you work with someone that you've known for five years By the way, my experience is more similar to yours.

I count my lucky stars every day. Interesting. I didn't know that was a prevailing advice. Yes. Yeah. If that is, then I don't agree with it. I think the thing that doesn't matter a lot more are, hey, do you want the same things out of life? I think that's like the most important thing. Like, are you equally committed to being a founder? Do you want the same thing out of the company? If that's not aligned, which I think is not aligned for most founders, I think that's going to be tough to work out. And then after that is like, do you guys kind of operate at the same level? um but yeah so maybe if you are friends for a long time maybe it's more likely that those are true right but I think that matters a lot more than knowing someone for a long time when founders come to you now like asking you stuff what are the types of things that they're trying to figure out um it's all sorts of stuff like usually it's I mean the same thing right it's like you always kind of pay it forward like anyone that is like maybe a year ahead in terms of progress has a lot to offer you know someone because it's like the most it's like you're in the same time period it's like everything's relevant um like for us um like there are a lot of founders of who i really

like uh you know ramp is a company i really like but you know they're a bit older etc but you know those guys i think i've executed really well i think harvey's been really gracious with their time just because they're exactly a year older than us and like we've been pretty much on the exact same journey so yeah you just ask them about everything and like you know when people ask me it's like pretty much anything back to our earlier point it's like you can only really talk about your own experience like i think venturing out like trying to give opinions on people's situations is a little bit dangerous because like you don't really know their situation that that in depth but if you can talk to your own experience that's hugely valuable yeah because then people have a data point of like oh okay so this is this is what the team look like this is the customer base look like um here's how we dealt with like you know when execs don't agree on something or whatever yeah that's the you know like that's the point of the show you know it's like you know you tell your experience then if somebody listens and is like okay i can like glean something from that like i mean right now this is my own selfish endeavor of being like

all right what number was your marketing hire you know like okay like doesn't mean it's necessarily perfectly true for me but like it's interesting yeah it's just a data point that's all you need like it's interesting data points yeah you know and then as the as the company grows there's fewer and fewer data points that you can ask so each one is very valuable what do you mean well like there's like at a current stage there's fewer and fewer companies that have been at this stage in this environment like a couple months ago or six months ago So, like, you got to make sure that you know this guy as well, gals, that, like, hey, we spend time together, and, like, they like us, and as a result, they're, like, down to, like, give us advice, you know?

And, yeah, to your point, the advice could just be a data point. Like, it doesn't have to, we don't have to be, like, get their opinion. In fact, the advice is preferably a data point. Exactly, yeah. Yeah, yeah, yeah. You don't want people to, yeah, it's like, they just don't know, but it's like, hey, here's how we did it. it's like oh okay cool like here's how we ran a sales leader search it's like okay that's very helpful because i hadn't done a sales leader search before so it's great to hear yeah yeah um when was your first finance hire maybe like 40 people 30 to 40 people yeah and so were you setting like comp plans on your own yeah roughly okay uh we didn't find that that hard like sales comp plans yeah sales comp plans we just asked like some sales leaders that we do yeah and we just use them okay they've changed a lot over time but uh yeah that's that's just what happens i'm stoked for you thank you it's amazing what you're doing like amazing yeah i hope the show goes on for a long time you too um i hope you continue to move into new offices that continue to feel big and rectangular yeah at some point the rectangles get too big that there's no offices that exist but yeah i guess you have like multiple you stack two floors right now we have two floors

and the thought was like 200 then the next 200 go above type thing no actually the thought was like okay once this floor is done we'll just find a bigger like rectangle but then that took us like way longer than we could so because in the past it was like pretty easy to find office space then this this one like took a while in fact it's still getting built out right now like they have to like tear down walls and stuff to achieve the rectangle that we want and so we were like okay well yeah it turns out the floor below us is available so let's just get that crazy yeah yeah there's a whole uh there's a whole like art to office spaces how often do you get the team together like uh does the sales team come at the end of the month end of the quarter oh um at least once a quarter and we have like other reasons for teams to get together it's much harder for the entire company to get together now because it's just too big yeah but we had like our first big off-site uh i want to say january we were maybe like 200 people then and that was your first ever offsite i know that's not true we did offsites before but we're way smaller yeah like an offsite for 20 people was like you just get dinner somewhere yeah yeah uh yeah that was like a

big offsite and then now we're trying to think like oh man like how would you even do a full company offsite now that's funny like i mean obviously we're not even like you know we're at whatever 35 about to be 40 and um we do dinner together at roadrunner every wednesday oh nice everyone's day dinner together yeah whole company used to be easy yeah it's like you know eight of us six of us yeah go get like a table somewhere now it's like 40 people yeah where do you go you can get the whole restaurant you know it's like yeah it's like this is like yeah you gotta enjoy those times though we all we all that's the other thing we tell everyone it's like you kind of you gotta enjoy like the stage you're at because it won't last that long yeah and it's like hopefully the like the good old days will always be now you know it's like when we were in the old office we always told people like you guys should remember this office our old office is not nearly as nice as our current office but it's like you should always remember this office because you'll think back at this as like the good old days yeah when everyone was eating dinner together now it's like impossible for 200 people to eat dinner together

But yeah, we still need to try doing more. One of the values of doing catering is that everyone eats at the same time. We ran an experiment with catering and people liked it because it felt more like the old days where people were eating together. Because now people still eat together, but you just order and it comes at different times, so it's trickier. but then people thought the food was bad so yeah so i'll figure out better food but i think the dynamic is of catering yeah yeah we started to do the break-even math on yeah how many people does it make sense to start catering yeah because we're trying to like solve the same problem yeah yeah and then like you know we're like you know we're talking about doing an off-site because things are growing quickly and people are you know remote now into sales whatever oh my god we got to do it soon otherwise like this is just like unwieldy and expensive yeah you know yeah yeah yeah but um yeah my my ea is actually like world class at planning stuff come on so she's like done all the off sites they've all been like super smooth so yeah you guys want suggestions but i think we mapped out basically a ton of the locations around the bay that would be good for 40 50 people yeah

so we so where we where we netted out this could be a disaster we'll find out yeah is um yosemite uh and we're doing uh like glamping it's called auto camp yeah probably the last time we'll be able to pull this off was my thought that's super cool you know like a three and a half hour drive get a bus gave the company like you know basically our first holiday type thing and everyone's like giddy. Yeah, it's important though. I mean like more giddy than like the biggest deals that we've ever closed. You know? Yeah. It's just a great experience. Yeah. It's like most of the time people don't spend time together doing like outside of work stuff, you know?

Like they may spend a ton of time together, so it's not a lack of time, but they're just talking about work. But I think like people really bond when they're like playing basketball together or something. when did um this is going to sound weird but like when did like politics start to creep into the company where you're like oh my god like people are jockeying for this and that and roles and you know starting to point fingers if you know deployment says it's engineering and engineering says it's a product and like you know you don't when do you have to start worrying about that stuff slash how annoying is it i mean i think it starts pretty early it's like as soon as there's a team then like there's going to be some element of that and i think asha and i have always been very like allergic to stuff like that so we try to stamp it out aggressively as soon as possible and yeah it's like you know someone's complaining about um again i think this this doesn't happen that much at decagon i think we're like fairly apolitical you know hopefully but as far as you know as far as far as i know uh because when stuff does happen we like are pretty adverse to it like if someone is coming to you and saying like hey like i should own this other thing and like someone

else is owning it right now shouldn't you be worried about your own stuff right now totally like yeah a lot of stuff you need to do like what's what's up with this what's up with that and yeah hopefully that helps a bit over time i don't think it's i don't think it's possible to point one of uh one of our early engineers came to me uh yesterday two days ago was you know had feedback on someone based on something they saw started telling me i'm like dude don't don't tell me what are you telling me for i don't want to hear any of this go tell the person like don't tell me what do you want me to do you want me to go tell them on your behalf yeah like go tell them like or worst case what are you going to do like sit on it Let it fester. Yeah. I think one of the big lessons that we've learned or we've kind of been coached on is most of these cultural things result in things like that. They're very actionable, right? It's like if one of your cultural tenants is go direct to people to give feedback, I have no opinions on if that's a good one or not, but at least that's very actionable, right? It's like your culture has to be built on stuff like that rather than we're going to be a transparent org. We value transparency.

Jesse ZhangIt's like, that is much weaker than like, okay, anytime you want to give feedback to someone, you tell them directly. I think you have to build a list of actionable things like that.

Yeah. When, um, after he did it, one of our values is the truth sets us free. And after he did it, I texted him, the truth set you free. Like you have been unburdened from this thing that you felt yeah like you've been set free by that burden yeah it's important yeah true good man thanks for doing this thanks for having me yeah it's really fun yeah really fun how often do you do these uh used to be weekly okay it's worth 300 episodes or whatever yeah you do this on top of uh the company still yeah used to be but i would do it for like you know in the spirit of like going and talk to founders yeah yeah i would do this without a microphone yeah it's a great uh i would do this without a money you know like this is just i enjoy like this is a fun i enjoy this cool and it is like my own like you know i don't have like a bunch of questions that i gave you or whatever it's just like shooting the breeze yeah and i enjoy that what's been the most surprising thing with uh your company before because before starting i'm sure you've seen so many companies at roadrunner yeah um most surprising one is we basically had pmf without the p like from incorporation and i know how rare that is just like getting demand breathing down your neck and we're starting like in the enterprise

you know like playing on hard mode in a lot of cases except for the market and i don't take that for granted um like i'll maybe some things that i've been experiencing recently we used to brag about how our um tell the board like you know our hiring acceptance rate is so high yeah and now it's like much lower and it's because we're trying to scale the company and so we're just in more fights yeah you know we probably lost you know candidates to you guys you know like we're in more like with great candidates, but like we're in more fights and the types of candidates now it's a different profile. The economics are different, you know, like first 10 people.

Yeah. It's easier to, you know, like they have ultimate ownership. Yeah. Now you have like, you know, you can still tell them they have like great ownership, but it's, you know, like you're part of a team. Sure. You don't own one product. So like that has been a different recruiting motion. I have been the most common question that I guess get asked is like, are you having fun? That tends to be the question. And I would not describe it as fun. It wouldn't be the first word I would use. I feel like I feel alive. That's like the most surprising feeling that I've had is like how alive I feel. Like how everything feels visceral to me. And most of the time, like it's not fun alive, you know, it's like, holy shit, like this thing, are we going to ship this thing? You know, like, is this customer actually going to buy now that they've bought, like, are we actually going to deploy it? And I think that's like, uh, the scope of things that I now care about is insane. I just can't believe how many things I have to care about.

Yep. I don't know how else to say that. And there's some things that I just I don't know. I don't want to care about, honestly. Like, finance. I just, like, don't- You have a finance leader? No, we need to hire one. That'd be a good way to not care about it. We need to hire one. But I'm like, okay, great. Like, I need to go hire one. But, like, then I look at the list of, like, the other things, and I'm like, eh, it's, like, probably not top three. but i hate it you know but it's probably not top three you know and so um those have been a few things that have been surprising i guess um i don't do any of those resonate with you yeah for sure um the i think like at some point we realized that the only way out of situations like that is to hire because until you hire you're not gonna get that leverage that's true but like the like a layer behind that is like the opportunity cost of the time that it takes to do that is taking me away from doing things right and then everybody has that same feeling by the way across the entire org yeah so one of the things that we're feeling right now is like my head of sales always wants my head of essays like our head of implementation to be on all the calls with him even pre-sales yeah and i'm like

dude why are you doing this like she needs to go higher and he's like well you know she's going to help us put our best foot forward and i'm like yeah but then we're going to be stuck in this forever yeah and i'm like you know i could be selling still yeah and i would probably be putting the company's best foot forward if i was selling still but like you're here now you have like a couple AEs on your team. Was there a tax that we had to pay by like not putting our best foot forward in air quotes? Maybe. Uh, but like eventually, like, what am I going to do? Just like be the bottleneck to every customer. This doesn't work. And so there's like some, even I go through these like growing pains where I'm like, Oh, like there's something more, you know, like best foot forward in anything. Sure. Does that make sense? And I can feel both me and the company like even my co-founders aj and eugene like geniuses brilliant i can feel them they got to go recruit engineers but you know like aj has like 15 really important customer calls today yeah roadmap there's no easy answers this is hard and like recruiting feels like short-term opportunity costs but if you don't do it there's going to be longer long-term way higher opportunity

costs yeah because then you're always going to have to do all the finest things that come up that's true but then like on the recruiting front it's kind of like juxtaposed with this feeling of like if we don't ship this thing nothing else matters like we don't earn the right to go do anything else yeah if this thing doesn't get out the door yeah it's tough you know not to do both i guess the other thing that i and then i'll pause is just like the i was doing seven days a week in the office, which is why I asked about the like wife day. I think it's really interesting. Like my ability to have stability and like bliss at home is like almost a prerequisite for me to be good in my job. I just can't, there's just too many things in my job for me to not have like peace of mind at home. And that requires like deposits in life. And it took me, it's taking me i'm just like that's not easy yeah if that makes sense it's just like harder yeah and it you know now i'm like giving myself saturdays giving us you know my my partner saturdays uh i didn't expect that like i thought i could basically just redline this thing all the way through in a lot of different ways you know now like i'm doing it i'm kind of like then the team is doing

it kind of follows suit anyway Yeah. I don't think there's like one answer for everyone. I think even just in, in a vacuum, if I'm working seven days a week, I feel a lot less energized the following week. So having a day, at least for my natural cadence is pretty important to keep up the intensity and the other days. The other thing that I think has been surprising to us is like, every time we think we're like, Oh, by April of this year, like we're going to be doing all of these things on the product side. And like, you know, the way that we're building this agent that has to work deterministically on, uh, customers, price books, approval rules, discounts, all the things that when you want to send a quote out, you have to make sure like it follows policy. It's like kind of actually the same problem that you're solving applied to our vertical. And there is nobody has figured this out so it's just like really hard and there's like a million edge cases and if we go down we get sued you know uh and so it's like the gift that keeps on giving of like you know it's just harder longer more bleeding edge than we thought and the techniques are changing like i mean you're writing about it right now yeah they're changing like monthly yeah so you're

just like kind of like it's uncomfortable yeah you know it's like are you doing enough on the team how do you hire you know like you just like there's so many variables that are uncomfortable i don't know how else to say it yeah does that make sense yeah totally relate believe me the same same sorts of uh decisions that we made on our end so um well keep blazing the trail for for everybody keep doing it keep pushing man thank you yeah thanks for having me it's great really fun yeah appreciate it that's it for now if you like the episode please leave us a review or go back into the archives where we've done more than 200 episodes with some fantastic folks this podcast is a Kleiner Perkins production and I'm Juven thanks for listening