Sam Blond on the Future of Sales in an AI-Native World | Ep. 54

[00:00] Buyers still want to talk to a person. They don't want to buy from an agent, a like, you know, Jack Altman avatar that shows up to a call that is like not really Jack. So there's no higher ROI on my time than spending time with customers. [00:18] Sam, what a delight to be here. I'm really excited to do this with you. Thank you for having me. Awesome to be here. I've been a fan of this for a really long time, so it's cool to be in this chair. I'm going to try to live up to the hype of that.

So I actually first... [00:30] learned about you, [00:31] by reading Jason Lemkin's Sastra blog back when I was starting Lattice, trying to learn about sales. And I remember [00:38] In there, it was like, you know, Jason's talking about my best, you know, sales rep at Echo Sign, and he did all of this. Then I obviously knew about you through Parker, who we both know from, you know, Zenefits and Rippling. Obviously, so I've known about you for a long time. Obviously, I've gotten to know you well over the last couple of years.

But I actually want to start by talking about sort of your sales journey. So can you talk through like, maybe just like a quick summary of like how you came up through sales, you know, a bit about these companies and maybe some of the things that you learned in each of those chapters? Yeah. [01:08] company. So Jason and Parker, both of which you alluded to, two of just like the greatest people, but also most influential people on the career that I've had and just like amazing advocates and close friends and all that stuff.

So shout out to those guys. And so let's see, I grew up in Kansas City and went to University of Missouri when I graduated. I was really fortunate that my older brother, Brian, was in San Francisco doing tech sales. I don't think I ever would have ended up [01:38] Cisco got into tech sales. I was at EchoSign and I appropriately said, like sort of lucked into the relationship with Jason. I was just like, you know, using a recruiter that was introducing me to early stage startups. One of them was EchoSign and I had a job offer and I took the job.

And so I started as an SDR, as many folks do in sort of early sales, go to market in tech startups. [02:08] me the opportunity to move up into more senior sales roles within the organization. Then Jason introduced me to Parker, went to Zenefits. I was VP of sales there for a few years. Crazy years there, which we can get into, but what a growth trajectory that was. Yeah, it was awesome. I was there for a little under two and a half years. For two of those almost two and a half years, it was incredible.

And then towards the end, sort of left turn into [02:38] goes deeper or is not as you want there. And then prior to doing Founders Fund and ultimately Monaco, most recently in the sort of sales career, I was CRO at Brex. And again, same idea, just joined a company that was really exceptional from a very early stage. And so I think three times have benefited from the experience of joining when companies are relatively unknown and near zero [03:08] and lots of revenue. Yeah. So we can spend the least time on this because it's like reaching far back into the past.

But like, what did you take away from EchoSign? Like, obviously, those were formative years for you as you thought about like what good sales looks like and what a good go to market machine looks like. But like, that's probably where you got a lot of your early ideas about how this stuff should work. So like, what were your takeaways there? Yeah. Well, I think there was some... Were you guys up against DocuSign? Yeah, that's right. So DocuSign was a competitor. [03:38] and then Adobe had acquired us. EchoSign became Adobe Sign after the acquisition.

We were actually beating DocuSign when Adobe acquired us. And DocuSign is maybe the more familiar name now because EchoSign evolved into Adobe Sign. And so let's see, a couple of things stand out. First and foremost, and again, I genuinely lucked into this. I think there's like nothing more influential early in one's sales career than the company that you join. [04:08] bit of the success of that business, you know, I was an SDR and then I was a sales rep and I was one of, let's call it like 10 growing into 40 salespeople.

There's only so much that I can sort of attribute EchoSign's overall success to me. It's funny. I put this in the true but hard to convince people of bucket of things where it's like with somebody early in their career, it's like, you know, you've got like compensation, title and quality of company. And it is very hard sometimes to convince people that quality of company is more important than those other things. [04:38] We can, of course, deal man the others. It's arguably like the only thing that matters, especially if you are joining as it is starting to take off.

The way that I think about these things, a lot of it is like the risk reward. And like the earlier you join, almost definitionally there is more risk. But if you can join like right at an inflection point when there is some signal that this company is really about to take off. But you also join in a very early stage where you are like the first, the second, the third, the fourth hire in the role or function that you are joining in. [05:08] from there just is like so, so strong.

That's exactly right. So, so Echo Sign, um, there, there was this thing that was largely outside of my control, um, that was like the overall success of the business. It was just good. That influenced my personal success, uh, as much as anything. I think there is like a different, um, variable here. Um, I, uh, [05:29] I have I sort of lucked into or found a career path that is a good fit for me. Like I enjoy this a lot and I'm pretty good at it in ways that had I tried something different, I would have probably been less good and enjoyed it less.

I want to go. I want to go to Zenefits. Parker, obviously, one of the great founders of, you know, the last decade. And, you know, obviously Zenefits in some ways, like, you know, he basically rebuilt Zenefits. [05:58] and figured out like, you know, these are the product things that need to happen for this to be a super durable company. But there was really strong product market fit there. But I think equally notable, the go to market machine and apparatus that early benefits had was like remarkable. And so like, yes, in the end, like some product things weren't there.

But like, can you talk about that early scaling? Because I think it was like at least of that, you know, it was maybe what, 2013, 14 that it was scaling, something like that. [06:28] left in quotes, around the same day in 2016, I think it was February of 2016. Can you talk about what building that go-to-market machine looked like in those early days? [06:37] Yes. So let's see. We've talked about Parker a little bit. I think an inspiration in a couple of ways, just in terms of like learning so much on how he is a founder and CEO and runs a business.

There's just like a lot of lessons there that you sort of organically learn from. What's one that you like come back to a lot? [06:57] There was a thought exercise in March of 2014 that when I signed up for Zenefits, we had a revenue target of going from effectively zero, maybe it was a few hundred K when I joined in December of 2013. So we were creating our 2014 plan. We wanted to go from effectively zero to $10 million of ARR by the end of 2014, so in 12 months. Which, by the way, in 2014, now there's people like that.

[07:21] That's like today somebody saying zero to 100. That was sort of unheard of. And Parker, let's see, Parker, as he should, has sort of like very ambitious, dream big aspirations and expectations. And so zero to 10 million was like there weren't a lot of other startups that were doing it. And so then early in the year of 2014, we were trending towards more than that. [07:51] a thought exercise of instead of finishing the year at 10 million ARR, which is our like, you know, stretch goal or however you want to frame it.

What does it look like if we finish at 20? And we want to back into sort of like, what are the headcount implications of doing this? What are the sort of like lead implications of doing this? How many leads would we need? What would the marketing spend look like? And you sort of like do whiteboard session on, I don't know, Monday night or whatever. And you end at 1 m. And we kind of like look around the room and Parker's like, well, we're not going to tell the board yet, but we're going to do this.

And three [08:21] Like the new goal is 20 million in ARR. So there's a takeaway that you can like apply that process to all sorts of aspects of the business. And is that basically, does that boil down to just like people rise to the level of expectations you set and just pushing the boundaries of what great could be just sparks more achievement? Is that kind of it? I think there's something there. I also think that there's something around like manufacturing urgency and having like really audacious goals. [08:51] process is one that I try and apply.

And it can be something like a revenue target. It can also be something like how long is something going to take? What would it take actually if we needed to do this in a shorter amount of time? And what would sort of be the trade-offs in those sorts of things? And so it's just operating rhythm of the business, something like that. Okay. So you have these ambitious goals for the year. So then what goes into that? When you said, okay, what does need to be true to go to 20 instead of 10?

What is that conversation? Well, I think one of [09:21] we benefited from quite strong product market fit at Zenefits. We benefited from the same at EchoSign, at Brex, now at Monaco. And so then I think that's worth highlighting. I do think that there's like something that – [09:37] we were pretty deliberate about at Zenefits that I took with me to both Brex and now Monaco, is being like very intentional about creating what I would describe as a demand rich environment. And I think that many founders, sales leaders, startups broadly sort of misdiagnosed the opportunity to acquire customers and grow revenue more quickly as something related to conversion [10:07] we have these opportunities that we're tracking.

We're in July of 2026. If we look back to June of 2026, and we maybe missed our revenue target. The reason that we missed that is because like, you know, gosh, this one deal that we really thought was going to come in and the sales ref said it was going to come in, it pushed. And so had it come in, we would have hit our revenue target or something like that. And my diagnosis in many of those instances is actually [10:37] And if three of them close, you finish way over target.

Yes. And if that one deal closes, you actually hit your target. But in a lot of ways, like you could have done better. I can't remember who it was. It was either you, Parker, or... [10:49] Matt Epstein. But one of the three of you told me at some point when I was like trying to get, you know, go to market advice for Lattice, it was like, look, you can improve your conversion rate by this much. You can improve like your [11:00] you know, first deal to op, but like the thing that you can change by 10 X is your top of funnel.

That's right. And I think that was always deep in, um, [11:08] you know, this group's psychology is like, you can improve all these things a little bit, but you can improve the top of funnel. Like if you have a company worth building, there's like a hundred times more customers that you could be talking to than you're talking to. I think this is like a very underrated thing. And it's like kind of like a red pill once you see it. [11:25] It's something that we have lived by and I think benefited from.

And just to sort of like reinforce the thing that you just said, I would. Well, I. [11:37] if you have 10% conversion rates. [11:39] uh, improving those conversion rates to 20%, which sounds like you're improving your conversion rates by 10%, but you're actually doubling conversion rates. It's really hard. Uh, and especially like, you know, if you have a sales organization, you have to like train the salespeople. If you're a founder, you have to get like far better at like pitching and closing and all of these things. Um, if you have a large enough addressable market, and so this doesn't totally work if you have like 50 potential customers that you can sell into, but for companies like Monaco and many other [12:09] easier to double your leads or opportunities.

And so that is where I would put a disproportionate amount of intention. And if you do so, actually at the expense of either conversion rates or maybe like efficiency, that is a worthwhile tradeoff. And so if you feel like as long as like on a per [12:30] rep basis, they're still closing enough per person per year kind of thing. As long as your growth trajectory is dramatically increasing month over month, if you have the efficiency per rep, do you care about that? Or is that something that doesn't matter till later on?

Yes, but you can apply the same logic that we just did at the company level to the rep level also. So I would rather deliver two times the number of leads or opportunities to [13:00] Give them less leads and increase their conversion. Just single our through, like focus on the throughput, the outcome. Yes. How much revenue did we close as a business this month? How much revenue did each sales rep close this month? Yes. Um, there aren't, what, what's my dad say in golf? There aren't like pictures on the scorecard or something like that.

And so like if a rep closes, I don't know, a couple hundred thousand dollars a month, it's not like, and I say this thing to reps all the time. It's not like there's like an asterisk for what your close rate [13:30] this customer that otherwise could have clicked. It's like, [13:32] $200,000 of ARR closed this month. Like that is the thing that you see. And so like, of course, you want to focus, the details matter. And of course, you want to be constantly improving and giving feedback on all of those things, but solve for the outcome.

Yeah, that's good. So what did you take then when you went to Brex? So like you had the Zenefits experience, it was both amazing and, you know, difficult in all these ways, which, you know, are well documented in the end. But [14:02] You've gotten the chance to be the leader from basically the get-go at this next company, and now you're doing it again with the lead seat and the experience. So now what happens at Brex? Well, I'll touch on the two things that I think – actually, the three things that influenced Brex's outcomes while I was there as much as anything, two of which were true at Zenefits, one of which was actually a learning from Zenefits that we started far later than

[14:32] able to capitalize on early at, uh, Rex. Then we can kind of do the same thing if it's interesting for Monaco because it's a different world today than it was in 2018. Uh, the three things, the first is like, um, recruiting and building the team, uh, at, uh, [14:46] Zenefits, my first two hires were the top two sales reps at EchoSign, brought them with me. Their names are Matt Plank and Jameson Young. Matt Plank is now the CRO at Rippling. Jameson Young was CRO at Gong. He's now SVP of something important at Rippling in their sales organization.

So these are like two of the people that have actually influenced my personal success as much [15:16] Zenefits and Brex now at Monaco, like we just have an incredible sort of like NFL level of players in a sales organization. And I think, you know, we can attribute so much of the success of the go to market organizations of these companies to the people that exist within the go to market organizations. I think the second thing we touched on is we don't have to go much deeper. [15:46] very effective job of was going out of stealth to like everyone knowing and talking about Brex very, very quickly.

And we did things like huge billboard campaigns and gifting campaigns and fundraise announcements and so much of the stuff that like maybe hopefully like Monaco is known a little bit. But you got really loud. I remember really loud. Yeah. And I think the idea was like we want as close. I don't know if we were as intentional as we are at Monaco today about this, [16:16] our target market to have heard of Brex. And so then when we reach out to founder, finance leader, controller from Brex, you know who we are.

And hopefully you have like some positive brand association with that. So we're very deliberate about that. And I think again, like the concept of creating this demand rich environment was something that we were very deliberate about early on at Brex. The third thing that I think we did, gosh, over time, [16:46] but it's benefits, we get something like a D plus from an early stage is like the influence of what would be considered today as revenue operations. And it's just being very thoughtful about, well, here's maybe the easiest illustration of this.

Not all leads are created equal. And revenue operations is like far more complex than this specific example. But I think this specific example helps highlight the influence that it can have. Not all leads are created equal. [17:16] both on like the type of company that the lead or opportunity that you are potentially selling to. There's also going to be influence at like the persona level. So who is the person that we are meeting with? One thing that we did at Zenefits, it was a mistake, is we treated all leads or opportunities, two sides of the same coin, as being equal.

And so we had things like opportunity goals that was sort of the thing that like fed into what is the ultimate outcome of revenue. [17:46] opportunities that converted at lower rates that led to less revenue. And so over this year of 2015, which was a more challenging year for Zenefits than certainly the 2014 year, I attribute a lot of that to the diminishing quality of leads and opportunities. And so the thing that we invested in early at Brax was really understanding what are the trends in the business and trying to pattern match to what are the companies and people that are most likely to convert and applying that [18:16] the sort of top of funnel and where are we pointing our missiles at targeting and acquiring these opportunities.

And so then you get the best of all the world. You get a leadership environment with the right type of people and companies that you're trying to sell to. Yes. [18:29] One of the things that I'm curious about is [18:32] For Brex, obviously you had, and this is true to all these companies, but Brex, there was this known highly competitive market with Ramp. [18:41] I'm curious about, and I would say today more than ever, basically every founder is operating in [18:48] an extremely competitive environment. Like, I think it's felt this way for a long time, but like, it really feels that way.

You know, like all good ideas have many, you know, you know, many contenders going at once. What did you learn about [19:01] competition through these and like how did you go to market through highly competitive markets? You know, it's interesting. EchoSign was certainly competitive with DocuSign. And so I think lots of learnings in terms of how to compete through that experience, [19:16] Brex evolved into being hyper-competitive. Yeah, but it started wide open. Interestingly, it was actually pretty greenfield for the majority of my time there. So my years at Brex were 2018 through like beginning of 2022.

So 2018, 2019, even 2020, it was mostly a one-horse race. There was a company called Divi that was acquired by com a little later. So there were other [19:46] of the market evolved, starting in, let's call it, 2121 and then certainly beyond. And I actually, what was not with the business for much of that period of time. And then Peter has this saying that's like, Peter Thiel has a saying that's like fairly famous that I think like is oftentimes, to your point, hard to apply to enterprise software that is seemingly like inherently [20:16] He he's so of course he's right because he's always right.

But, um, you know, experiencing, uh, Brex in what I would describe, you know, I said this term previously as Greenfield environment. Yeah. Um, [20:28] pretty smooth sailing. Monaco today, we think of it as pretty greenfield. And so we are displacing incumbents, but aren't competitive today with many new entrants into the space. We should just sort of like assume that that environment won't last forever, but we want to take as much advantage of it as fast as we possibly can to get like as close to [20:58] from the time at Brex, just in terms of focus and how quickly you want to move into different markets and segments and those sorts of things.

Yep. Okay. I want to come to that before we do. [21:09] After so, you know, this like obviously extremely sort of like this rich journey through sales. [21:15] after that and before monaco you did spend time at founders fund and you have like a new chat like a chapter to your life that was not about startup sales so like can you talk about what that was that experience what you learned [21:28] Why'd you come back to what you're, you know, a new version of what you've been doing? Yeah. Well, look, you and I have both talked about Jason and Parker.

I'd be remiss if I didn't mention something about like the learnings from Pedro Enrique Michael, who is CEO and now CEO at a company called Figure. And so like equal sort of parts inspiration and then let's see, gratitude for the influence that they've had on my career as well. [21:58] surrounding myself with the greatest people on earth. You know, like you go from Jason to Parker to Pedro, Enrique, Michael, and then we get to Founders Fund, right? And it's like, you've had folks on this, many of the folks on the show were talking about Brian prior to starting the recording, but gosh, Peter, Brian, everyone is just like exceptional there.

So let's see, I think I'm [22:20] I can get a little bit personal on, on like my mindset after Rex. Yeah. Um, so this is late 21, early 22. Um, I'm reaching like my four year, uh, uh, sort of tenure at Rex COVID. It is COVID. I'm in Miami. Uh, so I, I've moved to Miami at this point. And, um, [22:41] You know, I just felt like for the first time in my career, I felt satisfied, which is very it sounds positive. It's actually bad. I felt like sort of satisfied with what I had accomplished in this like category or world of technology sales.

And, you know, I could have let's make the assumption that I was leaving Brex. I could have done something like go either early stage and maybe like a more strategic title or something. [23:11] the probability of joining an earlier stage company that has a Brex-like outcome. We were a $12.5 billion company when I left, which is like definitionally low. And it's like, even if you did, it's like, it was kind of the same, it was just a bigger number. I wasn't motivated to do it. I wanted a new challenge. I alluded to my brother, Brian, very early on in this sort of like career arc that Brian was out in San Francisco doing technology sales when I moved out here.

Brian, at the time, had transitioned. He was a CRO at a bunch of really incredible businesses. And then [23:41] Hill. I mean, so I had seen him make this transition as, you know, like former sales leader. And I was in Miami. I got to know Keith and Founders Fund had a Miami office. And I made the decision that I wanted to get into venture. And gosh, if I had like the opportunity to join one of the greatest venture capital firms in the history of the world, I'd sort of be silly to not take advantage of that.

And so mid-late 2022, I joined Founders Fund. And like, [24:09] couldn't [24:10] be more grateful for the experience and the people in the firm are just like truly exceptional. No surprise to anybody that's potentially listening to this. Um, we weren't deploying a lot of capital at the time. This is like 22, 23. Um, and I think like I'm at the time I'm Miami based VC. Um, it was a little fish out of water. Uh, and so I don't know, you know, I talked about like, um, I did this thing at echo sign and then beyond that I could just tell, like, this is a good fit.

[24:40] Miami, but I don't know that like being in C. felt like the right fit. One of the things that Founders Fund has a track record of doing that I gravitated towards is incubating companies. And so certainly like Peter, the most famous of them with Palantir and then Trey with Andurl. And there's a bunch of folks that have Scott with General Matter and Belly and Vard and more. And so. [25:03] My brother, who I alluded to at Sutter Hill, he took this model to human capital. We decided to co-incubate a company that evolved into Monaco.

[25:10] And through that process, I was sort of gravitating far more towards like, what is the right fit? It's building Monaco and not being Miami-based VC. I asked you... [25:21] the other day just like [25:23] about like, you know, [25:25] I don't even remember why, but it was about like, you know, interest outside of work. And you were kind of saying like, well, to be honest, I don't really have hobbies right now. I'm just working a lot. But you're like, you know, I did have them in Miami. And yeah. Was that like a, [25:38] It feels to me almost like you had this very busy career [25:43] It almost feels like you took a breather and then you're like, I'm going back into the coal mines.

Potentially unintentionally, meaning to take a breather. I think what you said is exactly correct. And this this may be like it could be received negatively, meaning today I don't have many hobbies. And if I'm not literally in the office, I am thinking about Monaco and doing something sort of. I think it's very lucky to be so immersed in something that you don't have any hobbies. [26:13] Yes. [26:13] Yeah, no, it was certainly a deliberate decision. Like I knew that this was what I was signing up for when I made the decision.

And to your point, yeah, when I was in Miami, gosh, I was in really good shape. And maybe that's like correlated both with the place and the like flexibility of the job or something like that. I was on the water a lot. There were plenty of hobbies that existed. And when I went all in on Monaco, you know, I moved back to San Francisco. I live right by the office. [26:43] a high contrast chapter to chapter though. It is 180, like fairly stark contrast. And again, it was deliberate. And thus far, I'm like very happy with the decision.

I'm loving this. It's awesome. Okay. So let's talk about Monaco. So I guess this is why you started a company. Like, why this company? Like, why was this the one that you're like, I mean, I guess it's a little self-evident, but like, what was in your head where you're just like, you know, this is going [27:13] it wasn't part of the plan. [27:14] Um, meaning I had joined founders fund to be AVC. I didn't join founders fund thinking I was going to start a company, moved to San Francisco, actually become co-founder, CEO of the founders fund.

Right. Um, and so, uh, uh, started this company. It like was just pulling me, um, and felt very much like this is so obviously what I should be doing in my calling. Um, so I think part of it was, uh, uh, [27:38] Just the fit for me. And I think maybe the best way of articulating that is something like there's only one type of technology company I'm qualified to be the founder of. And it is a sales or go to market technology company. There is this other thing that is highly influential, and that is timing.

[27:56] And. [27:57] We are in the sort of early innings of this platform shift that is AI. And I do think that there will be a new market leader that emerges in the category that we are building in, which is go to market or sales technology. Yeah, it's like this paradigm, you know, in some ways seems to be. [28:18] Like... [28:19] I guess going back to cloud, it was like, you know, I guess neither of us were really working at the beginning of that shift, but it was. Maybe we're students of history, though, or something like that.

And it's like you can see that basically it's like there are all these on-prem companies. Yes. And if you started a cloud company. [28:36] at the right time, it was just really hard for those old companies to turn the boats quick enough to come do what you were doing. And it was just a genuinely better offering for customers. And so it just dominated. And in just like category after category, like the cloud version just won and the old companies couldn't get there and the customers just preferred it and bam. And it seems like in AI, there's a version of this happening now where it's going from selling tools to selling the work and marketing.

[28:59] It's just dominant to customers and the old companies can't seem to catch up. [29:03] I think you articulated it perfectly. These platform shifts rhyme. [29:08] where Siebel, that was maybe the incumbent or market leader in this category that Monaco is building in, which is go to market or sales, was the market leader. There was nothing inherently wrong with the business. In fact, like one of the most incredible businesses at the time in history. The same thing is true with the market leader today, which is Salesforce, just incredible [29:38] You can pattern match to other functions within enterprise software.

They're faced with an innovator's dilemma where they have an existing set of customers on a platform that was architected pre-AI. And so they can either continue serving the needs of those customers and focusing on where they are generating revenue and building on top of this existing platform, or they can disrupt themselves. [30:08] dilemma during a platform shift, they gravitate towards the former, which I think for us equates to opportunity where we can. And by the way, I think like what Salesforce and what other companies are doing, they are overlaying AI on top of a pre AI system architected platform, which is better than no AI, but less good than being truly AI native, which is what a company like Monaco is.

[30:38] And so for us, we can go after a sort of narrow segment of the market today, which is startups. And if you think about Salesforce's revenue, how much of Salesforce's revenue is concentrated in early stage technology startups? Less than 1%. Certainly less than 1%. And so we can go after that market. We can build a better platform. We can build a platform that's truly AI native. We can get close to monopoly market share there. [31:08] outside of startups and hopefully eventually evolve into the market leader. But whether it's us or somebody else, it seems a foregone conclusion that the category leader, the platform of record in sales in, let's call it five years, will be a platform that is architected with AI in mind and not one that was architected 20 years prior.

[31:32] You had a choice to make, which was... [31:34] Obviously, what you're selling is like work and outcomes and you're selling sort of like revenue in some sense. You chose to also be a system of record. [31:42] You didn't have to do that, but you made that deliberate choice. I think to the extent that you won't integrate with the system of record, even though you [31:48] You obviously could. You can imagine a world where you chose to do that. Most still. Many other companies. Right. Because it's easier to say, look, I'm not going to try to.

[31:55] you know, be your HubSpot, but I'm going to give you these tools that let you get more revenue and set up all these meetings and do all the, you know, accoutrements around the CRM. You've chosen to say, if you want to work with Monaco, we're the CRM. [32:06] Why did you choose that? [32:07] That's right. Well, several reasons. I think... [32:11] Thank you. [32:13] There are two categories of companies that are sales products. [32:18] There are system of record companies today that is a CRM. We actually believe that forward looking, this like concept or category of a CRM will evolve into something of the past.

We are more orienting around outcomes. And so we think that what today is this like system of record that manifests as a database CRM eventually becomes a revenue automation platform that's actually oriented around outcomes and not things like storing data. [32:48] type of company that emerges from this that is a system of record, but doesn't look like the existing systems of record. What does it mean to be the system of record? If not just like a database, what is it? [32:59] Uh, it is, um, well, look, HubSpot is appropriately named.

It is the hub. Everything orchestrates from the system of record. Yes, because it's the source of truth of data. And that's right. And you asked a question like, why did you make this decision? Well, if we, if we probably, um, if we bucket these, uh, company types or products into two categories, there's system of record and there's point solutions. Point solutions are layers on top of what today is a CRM system of record. [33:29] of those types of businesses backward looking. We have market leaders like Salesforce that today are 120 plus billion dollar companies just a few months ago are significantly larger than that.

And then several others that are actually like quite large businesses. If we think about the category of point solutions that integrate to these systems of record, there are some that experience some early revenue growth. [33:51] and early maybe marks of low to mid single digit billion dollar valuations. But none of them, historically speaking, have realized generational technology company outcomes. We're not motivated by being a point solution. We're not motivated by an outcome, which again, like a really exciting outcome for those that experience. We want a shot. We want a shot at being a market leader in one of the largest categories of enterprise software that we think

[34:21] evolve from here. Think about Salesforce and maybe enterprise software companies today broadly. Their market caps are predicated on IT budget. We are disrupting labor. Yeah, that's right. And so the future market leader has both that IT budget, but also has the labor budget. Monaco is way more expensive. [34:40] than that sort of legacy system of record products. Because we are doing the labor on behalf of our customers. - Which by the way is the story of all the AI native companies. Is it's true. - True. - It's both dramatically more expensive in some sense, and it's also dramatically cheaper in another sense.

[34:55] than what you would be doing alternatively to get the same outcome. That's exactly right. And and people not only are customers willing to pay, this is what they want. The other you asked a question that maybe I want to touch on because I think it could be insightful or maybe helpful for other founders that are starting businesses today. [35:16] There's an application of AI in Monaco-like products that is seemingly obvious, which is we are AI native. We just talked about it. It's the labor disruption. We are using agents and compute to replace workflows that founders and salespeople would otherwise be doing themselves.

And it is more expensive when a human does it. And it actually produces worse outcomes when a human does it. [35:46] certainly intentional from the very early days, the cost of building software is trending to zero. And so we want to take on as much scope as we possibly can, starting with the system of record, but also displacing all of these point solutions that we believe are actually features of a broader platform and not independent product lines or independent businesses in many cases. By the way, this extreme breadth focus. [36:11] was obviously sort of, you know, like Parker was kind of like one of the like early canonical examples of like the, what a software business really is at the end of the day is like these customer relationships that allow you to extremely efficiently build and sell more products to them.

And you, you know, the customer just gets a straight up better experience because the data is tied together. It ends up being cheaper for them in summation. You don't have to have all these different vendors, like all these things. It seems like now with AI, you should actually [36:41] The compound startup, maybe phrase or terminology that I think Parker made famous. Yes. And now it's like that should go like exponentially far. Well, I think Parker, to his credit, was probably ahead of his time on this, right, because Parker started Rippling in something like 2016.

Zinibitz was maybe less of a compound startup than Rippling was, and Rippling is more of a compound startup. I think that today, and I don't know, like the exact sort of math equation here, but we can build software. [37:11] 10 times faster than we could just a few years ago. If that is true today, that is going to be true a few years from now where we can build software 10 times faster than we can today. And so we want to go after as much sort of breadth of what we can do in the platform with the assumption that AI is going to enable us to build a product far faster.

And that is what customers want. Customers want to come to one platform. The outcomes are actually better because you don't [37:41] the system of record, the thing that does your call recording, the thing that does your outbound, the thing that builds your database. It is far more difficult to overlay an agent on top of this arbitrary set of tools with data silos than it is a single platform and source of truth that both has all of your data, but also takes all of your actions inside of the same tool. Totally.

So when you think about... [38:02] what you're selling to customers. In some sense, I guess, you're kind of selling... [38:06] well-wrapped tokens that can do all these different things, but you're kind of selling intelligence to the customer at the end of the day. So have you thought about like, you know, or I know you have, how have you thought about what this means in terms of the way you price, the long-term of what your cost structure is going to be and like what that all looks like from an economics perspective?

Because it's obviously very different than, [38:25] build software and sell it for per user per month kind of situation. For sure. Yeah. Well, two things come to mind. One is Monaco and we at Monaco are very opinionated. I think that there are certain applications of AI and maybe applied to different functions where it's largely like ones and zeros. And what I mean by that is like support is close to this, where you're like driving towards an outcome, which is a resolution to somebody's support ticket. Right. [38:55] it's even more pronounced, I think, in the world of like finance and accounting where there's like [39:00] an actual number.

There is like a real one zero type number that is the calculation of everything that comes before it. Yeah. I think sales is like. [39:10] We start with finance, we move to support, we progress to sales. There's like far more subjectivity that goes into sales. Then there is this sort of like black and white binary outcome that is true in the world of finance. And so we are very opinionated in things like how do we determine which types of companies to reach out to and when to reach out to these companies?

And what are the signals that we're leveraging and how does that be incorporated into messaging? [39:40] today just don't have experience doing, right? And so then that is the first thing that comes to mind is like the opinionated nature of the product. And then meaning that you're helping [39:50] It's funny because as you were saying that, I was like, I didn't know what you're talking about. You're talking about both. It's both about who you're reaching out to, but it's also then, you know, implied is who your customers ought to be reaching out to and all of that.

You know, everything you're talking about is kind of like what you're selling to the customers. [40:20] oftentimes have sort of deep go-to-market experience. And so we can take much of the sort of like decisions and strategy, which is a word that I don't hate, but I don't like, but I can't think of a better one right now, sort of off of their plate. And then we enable them to do the things that are super high leverage on their time, things like meeting with customers, coming up with creative campaigns that today AI is less good at.

But if you think about the workflows that I just described, building a database, overlaying signals, finding buyers, coming up with messaging, [40:50] things that Monaco is certainly better than me at and arguably better than just humans. And so then you can sort of outsource this thing to free up your time to do the highest ROI use of your time in a sort of like world of go to market, which is like customer facing. And then you asked a question on pricing. We are our pricing is correlated towards outcomes. Outcomes are relatively objective when it comes to Monaco.

Now, like the ultimate outcome or excuse me, [41:20] when it comes to the category of like go to market or sales. It's revenue. How much revenue are you generating? [41:25] There are some inputs. These are things like meetings and conversion rates. And so we rigorously track towards the ultimate outcome of revenue, the inputs of are we generating meetings? Are we improving conversion rates? And our pricing is aligned with how much a customer is using the platform. And that should be highly correlated with the impact or benefit that a customer is receiving from the platform that is like fairly easily measurable.

[41:55] So I would love to unpack kind of the go-to-market strategy you've had so far. You launched like February, so let's call it four or five months ago. [42:03] and we talked about this with Brex, but definitely you flipped a bit and everything was loud. So what I'm curious about is can you sort of [42:11] share what was in your head when you were like, okay, [42:14] It's time to launch. We're going to be loud. [42:16] here's the things we're going to do to sort of like get this whole brand going.

Yes. I think I'll describe our approach. It was the right approach for us. I'll also sort of caveat with a couple of things that I think are worth calling out that may be like advantages that we have as a business that don't necessarily apply to every startup. We wanted to take the [42:46] have a big sort of shotgun style launch, which we did back in February, where we're [42:51] We went from almost a definitionally unknown company. Nobody had LinkedIn Monaco up. Our website said coming soon or some version of that.

We certainly spent zero dollars. [43:02] on marketing up until the day that we launched. And the reason that we wanted to take that approach is, again, I haven't come up with a better analogy for it than this, which is like the boiling frog thing, where you can imagine if you are the frog and you're in the pot and the water is heating up and you don't totally notice it. Well, we can apply that to if you do marketing campaigns over a two-year period and as a consumer, you may see bits and pieces of somebody's [43:32] like, yeah, I've maybe heard of this company, but like I heard about them a long time ago and they like did this thing.

You can imagine the sort of like psychological impact of that relative to like dropping the frog in the boiling water, which is like... [43:45] Oh my gosh, we were seeing Monaco everywhere all of a sudden. Like, I see the plane, I see the billboards, and I see the poker tournaments. Your plane and your billboard gave no explanation of what Monaco was. [43:56] Like, it just said Monaco, and then, like, the billboards had, like, a big dollar sign, which I thought was hilarious, and I loved it. But, like, you didn't say...

[44:03] you know, new AI sales platform. You know, you just were like Monica. Yeah. We benefit from having a geographically concentrated target market. So we're selling to startups. You and I are sitting here in San Francisco. Many of our customers are also in San Francisco. So if we were selling to HVAC companies, we shouldn't be flying planes around San Francisco or putting billboards up around San Francisco because they're like fairly well distributed and not highly concentrated. So there are like maybe two aspects that we were deliberate about solving for. One is brand

[44:33] That's the plane. That's the billboards and and more. Yeah. [44:38] When we do think that there may be like two impacts of brand awareness. The first is we do a lot of outbound. Monaco does our outbound for us. When we reach out to a company that is graduating YC, reach out to the founder, they receive the message from me. They have heard of Monaco because they've seen the plan, whatever like the thing is. The likelihood that they respond to that outbound message is exponentially higher than if they didn't know me, if they didn't know the business.

[45:08] which is when they take the meeting, they are far more likely to convert because there is comfort in like knowing and understanding a brand like the one that we are hopefully creating around ourselves in ways that maybe other folks aren't delivered about and haven't created for themselves. [45:38] something like this, and hosting the poker tournaments and inviting specific founders to that poker tournament with the expectation that that specific founder is going to be somebody that we convert. So we solve for both. I can talk about maybe like a couple marketing principles that are things that we apply to marketing.

I would love that because, you know, like one of the things I've [46:02] often think, I don't think this applies to every startup, obviously, or I know it doesn't apply to every startup, but I think there are many startups that could be investing much harder in their brand that don't. And it's hard because it's like, well, if I do this demand-gen campaign, it turns into revenue. And if I do this brand thing or, you know, I spend this money on these sort of like brand campaigns, it's like not going to show up.

So it's hard to, but it just seems like a missed opportunity for so many people. [46:26] Yes. I think everyone should do this in their own specific approach. What Monaco is doing isn't relevant to most startups. We can do it because we sell to startups, the geographic concentration. Again, most startups don't sell to it. There's a version of it for everybody. I think there's a process that every company should follow. And then I can talk about maybe a couple of principles in case they're helpful. There is a process which like, [46:53] Most companies do not follow.

You've got to try stuff like like you just have to just do stuff and you can't be afraid to fail. And I do think that most companies here, they just don't really do anything. I do think that on this point. [47:11] It's a lot of people... [47:14] are afraid of the embarrassment of, you know, a brand campaign that failed or some marketing or sales effort that just like looked stupid and didn't land. And that's actually that is a that's psychologically harder than just like building product or doing other things that are not publicly embarrassing.

I think there are two things. [47:32] I think there's one thing that is like, I'm not good at this. So I'm an engineer, not me personally. I'm saying like putting myself in the shoes of the founder. I'm an engineer. I build product. I like I'm going to index on the thing that I'm very good at. I don't know how to do like a marketing campaign. Which is funny. You know, our CTO, my co-founder. [47:49] Eric at Lattice came up with by far our best billboard, which was like investing your people, not crypto during 20.

And that just like landed super hard and that engineer. Yeah. Yeah. So I'm not I'm bad at this or not experience this or whatever. Yes. [48:03] I don't spend the money. [48:05] I'm worried about like, you know, lighting the money on fire or something like that. I think those are the two variables that probably lead more towards stagnation or just like lack of effort in this category. The reality is like no one starts being an expert at this stuff. You've just got to like try stuff and learn. And I actually spend a lot of time with our customers doing exactly this.

Like my time, I spend customer facing all day. Let's come up with some cool campaigns that we can run for your business and just ideating on this. [48:35] high ROI to our customers. And you can do inexpensive campaigns. Like one, you don't have to be an expert at this. Two, there are campaigns that are inexpensive. I'll give an example. These like poker sets that we send to founders that say Monaco Casino, they're on brand that are prefab because Monaco has a casino. They're like 110 bucks. You can do a test, send this to 50 people, you're spending $5,000.

It's like, now like if you're truly bootstrapped [49:05] like $5,000. But you can still do stuff. There's always stuff. There's always stuff you can do. And you don't have to break the bank to do it. So you run a process. Here's what we do internally in case it's helpful for others. We run a process at least once a month. We want to have like a big splashy marketing campaign that we are trying. Get a handful of people in the company, define them as like the marketing committee or whatever it is.

They don't have to be marketing folks. It can just be you and your co-founder if you're just two people. Come up with a few ideas, put them on [49:35] Just do it. Just like jump. Don't be afraid to fail. Try something. If it doesn't work, chalk it up as a win because you learned and you're going to try something new that is going to be more effective or something like that. But you do want to have like a bit of process around this where every single month you're trying at least one or two different things that are in this like category of marketing brand awareness, demand gen, however we want to frame it.

And I think we really want to be contrarian is maybe like not the right application of that word, [50:05] New stuff. Like your plane. The plane. Was awesome. Can you talk about the plane? Yes. I feel like there might be one flying right now. We, there isn't. We took it down. We'll put it back up at some point. I think like probably reached diminishing returns or something over time. But it was like, yeah, anyway, go ahead. We... [50:22] We were at SASTER, which is Jason Lemkin's conference, the awesome conference. And we knew that there would be like a large contingency or concentration of people at this event down in San Mateo.

And so we didn't think this was like that creative. In fact, it wasn't that creative in that there was at least one, maybe two other planes flying at the same event. [50:41] Um, and so we had the banner trailing the Monaco plane at this conference. I don't know what we paid. Let's call it like a couple thousand bucks to make the banner. And then, um, I was surprised at how relatively inexpensive putting this plane in the air for many hours during the conference was, which is like 6,000 bucks a day.

And, you know, we do it for two or three days at the conference. Um, and I was just sort of thinking like, we already have the banner. Um, we already know like the cost of flying this thing. Yeah. [51:11] like [51:12] I haven't really seen these in like San Francisco proper. Do you guys, can you guys fly over the city? And part of my assumption was like there are air restrictions that like you couldn't fly in and around the city or whatever. And they were like, yeah, we can totally do it.

And so I was like, you know, starting to do the math on this thing. And it was like, [51:30] $6,000 a day. [51:32] pay for 10 days, 60 grand, [51:34] We have a lot of billboards. Some of our billboards are significantly more expensive than 60 grand. This is one of those that's like, [51:42] It's a $60,000 learning. The worst case scenario, we fly this thing around. It doesn't totally work. We learn from it and we don't do it again. It worked. Both messages on my phone, people posting on LinkedIn and Twitter and everywhere else, it was sort of everywhere.

And so we kept it up for a little bit longer. [52:12] from it. We'll put it up again when we do a big announcement that we have coming up. Yeah. You know, it's interesting. History kind of, I'm sure you've read Behind the Cloud, the early Salesforce book from Benioff. And one of the things that struck me was early Salesforce did a lot of really creative marketing. They did. Really creative. And some of it was that the message was created, like the no software thing. It's like, well, that's interesting. There was a lot there.

And just the way they even did customer dinners, I think was kind of