In short
Decagon’s agentic AI approach to enterprise customer support, emphasizing a deployment model where the AI is built and tested inside the product, monitored in-product, and owned by the customer—aiming to cut customer support costs by 65%.
Guests
Jesse Jang, co-founder and CEO of Decagon. Background: builds AI concierge/agent platforms for enterprises; previously co-founded a company sold to Niantic; started Decagon with co-founder Ashwin; scaled from early idea stage in 2023 to a $4.5B company; grew headcount from ~50–60 to ~500; hires with “bar raiser” style culture/intensity filters.
Key claims
Customer support is the “perfect wedge” for agentic AI; differentiation is deployment/ownership (not “forward deployed engineering” or “trust us to solve it for you”); AI empowers non-technical teams like cloud/code does; PMF emerged gradually (about $1M revenue with ~6 customers); conservative early hiring/fundraising, then more structured scaling.
Notable examples
Multi-channel support (voice, chat, email, SMS); monitoring AI conversations within the product; marketing hiring as product marketing first (first ~30 people); bar raiser interviews added around scaling to ~500.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOThe Power of AI in Customer Support
0:00 to 0:36
Exploring how AI empowers teams in customer support.
“One of the main benefits of AI, especially agentic AI, is that it really empowers people on the team to do more.”
Decagon's Customer Experience Revolution
1:12 to 1:40
Discussing how Decagon is transforming customer support with AI.
“Do you have the feeling when like, uh, okay, the feeling that I just had, like I started a company here at KP, it's growing.”
Scaling the Team and Office Moves
1:40 to 3:25
Jesse shares experiences of scaling Decagon's office and team.
“And then we moved into a new office Monday.”
Hiring Strategies in a High-Demand Market
3:25 to 4:35
Jesse discusses the challenges and strategies of hiring amidst rapid growth.
“In the beginning when you were, were you not, um, unnerved to be hiring ahead of like, okay.”
Building a Positive Company Culture
4:35 to 6:04
Emphasizing the importance of culture while rapidly hiring.
Lessons from Scaling: Adaptation and Iteration
6:04 to 8:06
Insights on adapting company processes as the team scales.
“That's pretty common for teams, I think.”
The Journey of Founding and Co-Founding
8:06 to 9:10
Reflecting on the differences of being a solo founder versus co-founding.
“I just don't, I just like being at home.”
Navigating New Challenges in the Market
9:10 to 14:00
Discussing the unique challenges faced in the current market landscape.
“air conditioned room doing what I want to do.”
Learnings from Previous Startups
14:00 to 14:48
The speaker reflects on the lessons learned from past startups and how they apply to current challenges.
The Importance of Co-Founders
14:48 to 17:06
Discussion on the psychological and practical benefits of having a co-founder versus being a solo founder.
“So most of those things you just pick up along the way, or you try to learn from people that are doing it a year ahead.”
Show all 31 chapters
Work-Life Balance and Team Presence
17:06 to 19:15
Exploration of team presence and work-life balance, specifically regarding in-office expectations and culture.
“I was listening to, I read or listened to something that Ashwin did where your co-founder, where he was talking about in the beginning, you guys were in every day.”
Navigating Growth Stages
19:15 to 21:09
An insight into the challenges of different growth stages in a startup and how they can impact the founder's experience.
“Like, realistically, the job today is like you're traveling a lot.”
Importance of Market Fit and Fundraising
21:09 to 23:16
Discussion on identifying product-market fit and the strategies behind fundraising early in a startup.
“You know, where's the budget coming from?”
Investor Relationships and Their Impact
23:16 to 28:00
Insights on building relationships with investors and the significance of their support during different phases of a startup.
Understanding Investor Relationships
28:00 to 29:04
Learn how to effectively engage with investors before fundraising.
The Cycle of Fundraising
29:04 to 29:58
Explore the importance of timing and frequency in fundraising rounds.
Navigating Market Cycles
29:58 to 31:18
Discuss the impact of market normalization on growth expectations.
“All the rounds were roughly like six months apart.”
Building Resilience in Business
31:18 to 32:36
Learn how to maintain a steady mindset through business ups and downs.
“That means fundraising continues to, like it hasn't been that hard.”
The Entrepreneurial Landscape
32:36 to 33:51
Examine the challenges and opportunities for new entrepreneurs.
“We have, um, we have like very few people that have sort of left the company, but, you know, we've had a few go start their own companies.”
Team Dynamics and Role Specialization
33:51 to 35:16
Understand the evolution of team roles from generalists to specialists.
“And, you know, this candidate during the, like when we were talking about her, I was like, Hey, this is going to sound like a weird comment, but like, um, she is like a software engineer, software engineer.”
Differentiation Through Implementation
35:16 to 37:26
Learn about the unique deployment strategies that set companies apart.
“It was very smart, very creative, like very just like self-starting.”
Marketing Misunderstandings in Startups
37:26 to 42:00
Discover common pitfalls in marketing strategy and hiring.
“And, you know, I'm sure Brett is great at talking with leaders.”
Navigating Early Marketing Challenges
42:00 to 44:25
Learn about the nuances of early marketing strategies in a startup.
Finding the Right Co-Founder
44:25 to 46:13
Discover the importance of co-founder alignment and luck in partnerships.
Sharing Experiences Among Founders
46:13 to 48:02
Understand the value of sharing entrepreneurial experiences and advice.
“Like, I mean, right now, this is my own selfish endeavor of being like, all right, what number was your marketing hire?”
Company Culture and Team Dynamics
48:02 to 52:03
Explore how team size affects company culture and social gatherings.
“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?”
Addressing Company Politics Early
52:03 to 56:00
Learn how to manage early-stage company politics and encourage direct feedback.
“Probably the last time we'll be able to pull this off was my thought.”
Building an Actionable Company Culture
56:00 to 57:10
Learn how actionable cultural tenets can empower feedback and transparency in organizations.
“I think you have to build a list of actionable things like that.”
Surprises in Startup Growth and Hiring
57:10 to 59:25
Discover the unexpected challenges and dynamics of scaling a startup and hiring practices.
“What's been the most surprising thing with, uh, your company before?”
The Emotional Rollercoaster of Startup Life
59:25 to 1:02:52
Understand the emotional highs and lows founders experience while managing their startups.
“that's like the most surprising feeling that I've had is like how alive I feel.”
Navigating Challenges in Product Development
1:02:52 to 1:05:19
Explore the complexities and edge cases that arise in developing cutting-edge products.
“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.”
Transcript
Automatic transcript. May contain errors.0:00One of the main benefits of AI, especially agentic AI, is that it really empowers people on the team to do more. Our whole thesis is like, how can we empower your team and how can we deliver an end result where the AI is fully in there? It gets built in the product. It's tested in the product. All the conversations that it's having, you can monitor in the product. We think that is probably a big differentiation right now. This deployment model where ultimately the customer owns the results and the process.
0:36Welcome to Grit. I'm Juven, partner at Kleiner Perkins, a show where we go beyond the highlight reel and explore the personal and professional challenges of building history-making companies. Today on the show, we've got Jesse Jang, co-founder and CEO of Decagon, the AI concierge platform reimagining customer experience. Decagon is building AI agents that help enterprises deliver faster, more personalized support across voice, chat, email, SMS, and beyond. We talk about why customer support is the perfect wedge for agentic AI and how Decagon scaled from an idea in 2023 to a$4.5 billion company.
1:12Enjoy the episode. Do you have the feeling when like, uh,
1:18okay, the feeling that I just had, like I started a company here at KP, it's growing. Yeah. Like that we incubated here. I moved in out of this KP office into a new office in January. And I was like, all right, this is like going to fit 30, 35 people. That'll last the year. And then, you know, four months in, we're like spilling on top of each other. Things are going well. It's a good problem to have. Yeah. And then we moved into a new office Monday. Fits like 120 people. Great. And I had this like weird cognitive dissonance where on the one hand, I was like, this is nice. but on the other hand i was like freaking out inside because i'm like are we gonna fill this huh how quickly are we gonna fill this right now it's too big like is this too nice like have we earned this you know you ever have that uh not really i mean we've never gone for like super nice offices nice meaning like too much space there was a little bit of that in our last office just because it was a small group at the beginning but we knew we were gonna grow pretty fast so why i mean we just had a lot of rules we were hiring for yeah and uh yeah it's engineering it's like all the all the rules kind of all add up pretty quickly and you have to get all the gna people and so on so um this our current one probably fits like 250 300 uh the previous one was like 70 max and so that was kind of a big jump um but this one's two floors so you know we start with on a floor first then we add another floor that makes sense um the new one we're trying to get everyone on like the same because like i actually feel very strongly um having one big 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 in a 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.
3:14So the new one is like one big, like rectangle. Where you can like see everything. Yeah. 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 not unnerving in any way to like hire ahead?
3:59It 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, we, for the first year and a half, we were, uh, 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. Uh, that went for sales as well. I mean, you know, in the beginning, Ashwin and I were doing all the sales and, uh, eventually when we hired our first salespeople, it was like, we already had deals for them.
4:34So 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 to 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 hundred 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 at 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 yeah 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 sales people yeah because uh you know we found people that we thought were really good and we realized that you know these people are not they're gonna 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.
6:31That's pretty common for teams, I think. 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 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 we work or something that's not too bad and then right yeah we just moved into our new new york office and uh 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 do you 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 they onboard in the u.s but you know i haven't met a lot of them and so it's important for me to go and just like meet the people yeah we have a good team getting built out there and yeah you're 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 afternoon here so um that that's the tough part of traveling but i'm getting a little bit more adjusted to it why do you like traveling generally i've never liked traveling ever i don't like traveling for fun.
8:50I just don't, I just like being at home. Yeah. Home is comfortable. 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. It feels like a waste of time to you. I guess. Yeah. Um, it's just not physically pleasant either. I just like being in a nice air conditioned room doing what I want to do. Uh, 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 how long were you there for? just July 4th like that weekend sweet do you feel guilty when you go travel?
9:30not really you mean as in like oh I should be doing work? I mean I do work when I travel but also it's also not super responsible to like be burning 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 was like there's like people yeah yeah and we also have a skilled team now that are all hard workers 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
10:19about probably 2 000 interviews does that feel right we've maybe done more than that that's what i mean conservatively to get 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 interview 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 that are growing faster than us, headcount-wise. It's like everyone's growing fast. The hard part is not so much hiring the people because there's a lot of people that want to work in high AI companies.
10:53It's making sure you keep your bar high. So one of the things we do is like Revolut does this, Amazon has a version of this. 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 intensity and so on. And we've added those to 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?
11:54I don't have a super... Do you have like a sense? I mean, it's definitely the majority of people make it past. Okay. Because it's the last step in the process. Right. If you're cutting the majority of people at the last step of the process, there'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 like having to basically reinvent every new process inside the company? like how quickly do you have to tear down a set of meetings add a new set of meetings um 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 growth.
13:13Yeah. 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, 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 moment. You know what I mean? And so, I don't know, I think in many ways, everyone's kind of making it up. And I think that has always given me solace. That's a good perspective, actually. Yeah, that's pretty true.
13:49You know, like 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 Ashwin 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 that was also learning I didn't like that so now we're in person and 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 a 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.
15:25So most of those things you just pick up along the way, or you try to learn from people that are doing it a year ahead. Yeah. I guess like, let's just imagine that was like a B2B SaaS 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 a uh like you're the only one that has like a founder responsibility in context and so i mean yeah tons of respect for solo founders but it's just very difficult and the 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.
16:28And 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 arrive at decisions and like probably correct decisions way faster. Because you're just kind of like another brain or another like processing unit. Now you can actually do some of this with Claude, which is kind of interesting. you can use that to bounce ideas, but it just gives you like a talking, like 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 in your own thoughts, it just takes way longer to arrive at ideas.
17:06That's the other learning I had. I was listening to, I read or listened to something that Ashwin did where your co-founder, where he was talking about in the beginning, you guys were in every day. Yep. The two of you. Yeah. That changed at some point, or maybe you're still in every day. When did you stop asking the team to be in every day? And was that like weird? Was it hard? Like, did you feel like you were degrading performance? Oh, 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. It's sacred. You have to have one day at least.
17:50But we're in every day. Wife day? Yeah. Do whatever, but don't do work. Just hang out with her. Exactly. Yeah. And I think early on, yeah, people would come in on Sundays as well. We never had expectation for people to come in on Sundays. It was never like, hey, you're joining this job, you're going to have to come in on Sunday. We're also okay with people having lives and not being in on Sundays. But yeah, around maybe 20 to 30 people, it's like not everyone's going to be in every Sunday. 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.
18:29They're just not in the office. Totally. 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. So Sunday is kind of like a pseudo workday. 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 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 Austin and 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.
19:13Are you enjoying it more or less than you did in the beginning? Like, realistically, the job today is like you're traveling a lot. I think it's one of those things where it's like, you know, 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 to now, the feeling hasn't really changed that much. I would say the only time it does change is when you're in the idea maze to maybe post-PMF and you're scaling.
19:48That is a pretty different feeling. And I think no matter what anyone says, the early 0-1 phase is way harder. It's awful. So, yeah, every stage has its challenges, but the 0-1 phase is 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 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 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 decagon 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 maze you know that sucks so 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 you're your founder starting a new company like they'll appreciate if you're asking more tough questions like, you know, how much we pay for this?
21:59You know, where's the budget coming from? Like, how do you justify ROI internally? Like, what 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, how useful 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.
22:37How 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 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 uh but like no one's going to 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 in hindsight like obviously we didn't listen to them but uh yeah no one's no one like really knows you know like no one's gonna have ideas like when people ask me for like perspectives on like what they're working on it's like you know no one's really gonna have nearly close to the level of depth to give like a credible you barely even know about your own business like yeah you're figuring everything out for the on the fly right now so i think um so i think optimizing for mid-career investors in the early stages i think is like 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 but 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 funds whole thing is like we don't want it like it's anti-signal.
25:15You do you. 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. How long did it take before 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 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 where 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 those are a bit more vertical i think there's other vertical use cases as well like law like some healthcare use cases but just in terms of like being 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 going to 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 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 And, 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 the market.
27:36So we have always tried to push it off. But yeah, I mean, there's obviously some benefits of raising. 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 raising a higher valuation helps with that because people just people shouldn't do this but pretty much everyone just like takes the dollar value of your equity so that's that's like kind of a marketing event right yeah it's a good marketing event yeah like 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 to read so you just put some messaging in there that's 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 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 they're 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 do you buy into the like thing so far it's been mostly the uh ladder 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?
30:32All the rounds were roughly like six months apart. Six months. Yeah. Okay. Which again, it's not always going to 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.
31:09You 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. 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 no 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 ones that are now growing fast like grew super fast during Xerp era and then like there was like a couple years of like kind of roughness and then now they're growing again like it is cyclical and yeah we want to make sure we're talking about that um like you know we've had very good quarters last few quarters, like when we recap the quarter, we tell everyone like, Hey, obviously it's great right now.
32:25Like everyone should be ready and that it's not always going to be so easy. So you got to build the toughness right now. You got to build, uh, you know, the grit right now. And that's, that's a message we try to, you know, make sure we emphasize. Doesn't matter. Does it? Yeah. It doesn't matter. We have, um, we have like very few people that have sort of left the company, but, you know, 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 still be pretty easy to start a company.
33:07I 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 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 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.
33:44Yeah, I was, um, we did a debrief on a candidate yesterday and at Roadrunner, there's a lot of people 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 going to sound like a weird comment, but like, um, she is like a software engineer, 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.
34:20I 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 don't I get both? Yeah, you can just get both. You can 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 early days, when you're spending up anything, the generalists are very valuable, because it's like one person with all the contacts, they can do a lot of things.
34:55As you scale, you kind of start hiring more specialists, because 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. It was very smart, very creative, like very just like self-starting. And 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?
35:32Like 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 in 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. 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.
36:13Yeah. 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 just like zoom out contextualize everything so historically we know 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's 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 um 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 getting into like enterprises and they're, you know, they've scaled their team really quickly.
38:06And, 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. But their deployment model is more similar to like a Palantir where they, they're really focused on, you know, forward deployed 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 at the 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 having 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 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.
39:52It is in the product. So it's like, can you build a product where the AI is fully in there? It gets built 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 the customer owns the results and 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 know 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 ashley they like our team but um 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 you know 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?
41:12The first one that comes to mind is probably marketing. I think a lot of people probably 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 that's that's a good point um yeah marketing i would say one i think we hired it a little bit slow though 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 to track everything closely but um yeah that's probably the the function that where i had to learn the most on what um hire was your first marketing person like uh what number it was first 30 people 30 yeah okay and what type of marketer was it uh product marketing and do you think you should have done something different no 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 of marketing and uh actually came from glean yeah uh yeah i think she's she's done very 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 could 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 how do you evaluate if someone's going to be way better at you than this and also be world class but once the team starts forming that becomes easier How did you and your co-founder meet?
44:29We had a lot of mutuals before so I knew one of his previous co-founders 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 the 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 and 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 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 oh and it's all sorts of stuff like usually it's i mean the same thing right so 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 what 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.
47:29Like, 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. Just the data points, you know. You know? And then 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 our 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.
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48:00So 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 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 And so were you setting like comp plans on your own?
48:49Yeah, roughly. Okay. We didn't find that that hard. Like sales comp plans? Yeah. Sales comp plans. We just asked like some sales leaders that we knew. Yeah. And we just use them. They've changed a lot over time, but yeah, 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. 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 floors.
49:30So 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 arts 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 off-site i know that's not true we did offsites before but we're way smaller yeah an off-site for 20 people was like you just get dinner somewhere yeah yeah uh yeah that was like a big off-site and then now we're trying to think like oh man like how would you even do a full company offsite now?
51:03It's funny. Like, I mean, obviously we're not even like, you know, we were at whatever, 35, about to be 40. And, um, we do dinner together at Roadrunner every Wednesday. Oh, nice. Every Wednesday, dinner together. Yeah. Full 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 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 so um but yeah we still wanted we still need to try doing more of it's like one of the things is one of the values of doing catering is that everyone eats at the same time and so yeah so we uh so we like we ran an experiment with catering and like people liked it because it's like it felt more like the old days where people are eating together because now people still eat together but like you just order and people 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 yeah and then like you know we 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 i'm like oh 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 offsites 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 where we netted out, this could be a disaster, we'll find out, is Yosemite.
53:25And we're doing glamping. It's called AutoCamp. 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 basically our first holiday type thing. And everyone's like, giddy yeah it's important like more giddy than like the biggest deals that we've ever closed you know yeah i mean it's like uh 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, this is going to sound weird, but when did politics start to creep into the company where you're like, oh my God, people are jockeying for this and that and roles and starting to point fingers if deployment says it's engineering and engineering says it's a product.
54:31When 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 there's going to be some element of that. and I think Ashwin 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 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 I know 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 but i don't think it's i don't think it's possible to avoid 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.
55:44Started telling me. I'm like, dude, 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? Like, go tell them. Like, or worst case, what are you going to do? Like, sit on it and let it fester? Yeah. Like, I think one of the big lessons that we've learned or we've kind of been coached on is, like, most of these cultural things, results in things like that they're very actionable right it's like if one of your cultural tenants is you know go direct to people to give feedback like i have no opinions 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 yeah like it's like that is much weaker than like okay anytime you want to give feedback to someone you tell them directly.
56:41Yeah. Yeah. 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 was 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.
57:40It's just like shooting the breeze. Yeah. And I enjoy that. What's been the most surprising thing with, uh, your company before? Cause 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.
58:24We 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.
59:02Sure. You don't own one product. You know? 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. Yeah. And I would not describe it as fun. It wouldn't be the first word I would use. I feel like, I feel alive. Yeah. that's like the most surprising feeling that I've had is like how alive I feel. Yeah. 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?
59:41Now that they've bought, like, are we actually going to deploy it? And I think that's like 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 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 the, 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?
1:00:30And so, um, there's been a few things that have been surprising, I guess. Um, I don't know. 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 certain situations like that is to hire because until you hire, you're not going to 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.
1:01:22Yeah. 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.
1:01:56This 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 you know it's just 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.
1:02:37That'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, um, my ability to have stability and like bliss at home is like almost a prerequisite for me to be good in my job.
1:03:20I just, I 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 me and 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 follow suit anyway yeah i don't think there's like one answer for everyone i 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 gonna be it we're 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 apply 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 so you're just kind of like it's uncomfortable are you doing enough on the team?
1:05:23how do you hire? there's so many variables that are uncomfortable I don't know how else to say it does that make sense? yeah, totally believe me the same sorts of decisions that we made on our end so well keep blazing the trail for everybody keep doing it, keep pushing man thanks for having me It's really fun. Yeah, appreciate it. That's it for now. If you liked 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.
From the publisher
How do you keep up when you go from 50 to 500 employees in a year?
Jesse Zhang shares how Decagon scaled that quickly, from hiring ahead of demand to keeping the company connected as the team grows.
He also explains why the zero-to-one phase is so different from scaling, and how Decagon found its way out of the idea maze in just three weeks.
Guest: Jesse Zhang, Co-founder and CEO, Decagon
Connect with Jesse Zhang
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