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

Sam Blond argues that the next sales leader will be an AI-native platform that automates revenue work while keeping people focused on customers.

Uncapped · Jack Altman

The best minutes

  1. 9:38Pipeline volume matters more than small conversion gains5 min
  2. 28:50Salesforce is constrained by its pre-AI architecture3 min
  3. 1:02:35Give buyers a clear path to getting valuePro pick 4 min

Also worth watching

  1. 6:41Zenefits reset its target after modeling a $20M year3 min
  2. 14:07Brex grew through strong hires, broad awareness and better targeting5 min
  3. 32:03Falling software costs push Monaco toward a broader platform6 min
  4. 42:11A launch burst can make outbound feel familiar4 min
  5. 52:59Early marketing spend should benefit prospective customers6 min

Skip the career chronology and Founders Fund story, followed by the competitive-market discussion and product-pricing overview.

Full analysis · 6 min read

Real Alpha · Nov 8

Sam Blond says doubling leads can beat a 10% to 20% conversion push

  • For large markets, Blond said doubling leads can be easier than moving conversion from 10% to 20%.
  • But Zenefits showed that raw opportunity counts can reward low-quality leads.
  • Track closed revenue per rep, lead quality and time returned by automation.

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Read the rest of the analysis

6 sections, the 3 other voices it tests Blond against, and what it means for you. Every episode we cut gets one.

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12:13

More pipeline can beat a higher close rate

Blond’s most useful operating point is about throughput, not persuasion. For companies with large markets, he said doubling leads or opportunities can be easier than doubling conversion.

His example starts with a missed monthly target blamed on one deal slipping. Blond said the company should have had like five deals.

The host then said three wins from that larger set could finish way over plan. Blond agreed, distinguishing enough pipeline to hit target from enough to exceed it.

His 10% to 20% comparison is an illustration, not a reported funnel benchmark. He said doubling conversion is difficult, while doubling opportunities may be easier when the addressable market is large.

At rep level, he would rather deliver twice as many leads even if conversion falls slightly, provided closed revenue per rep rises. But Zenefits complicates a volume-only reading.

In 2015, Blond said opportunity goals encouraged low-quality leads that converted less often and generated less revenue. At Brex, he said, the team later targeted company and buyer profiles more likely to convert.

“There aren't points for what your close rate was.”
13:35

Our read

The advice is to widen the funnel while judging the system by closed revenue. It holds only when viable buyers remain plentiful and lead quality stays visible.

29:42

Incumbents face an architecture test, not an AI demo

Blond’s CRM thesis is an architecture bet. He said Salesforce’s platform predates AI, leaving it to serve existing customers or disrupt its own system.

That is a seller’s framing, not a neutral verdict on Salesforce. Monaco sells an AI-native revenue platform and wants to replace CRM as sales’ system of record.

Blond said early-stage technology startups represent less than one percent of Salesforce revenue, giving a new entrant room to build in a segment the incumbent can neglect.

His forecast goes further. Blond expects the sales platform leader in five years to be built with AI in mind, but the episode offers no comparative customer results.

George Kurtz, CrowdStrike’s president and CEO, made a related point on No Priors in October 2026, urging incumbents to shorten development cycles and disrupt themselves.

That comparison supports the risk of waiting, not Monaco’s product superiority. Kurtz discussed cybersecurity, not sales CRM.

“less good than being truly AI native”
30:32

Our read

The startup wedge makes the incumbent challenge plausible, not proven. The test is whether a new architecture delivers better outcomes as it moves beyond startups.

35:46

Owning the record raises both upside and burden

Being the system of record is a bigger bet than adding AI features. Blond said data and actions should live in one platform, replacing scattered CRM-adjacent tools.

He argued agents work better with a shared source of truth than across silos for call recording, outbound and account data. That product thesis is plausible, but unquantified here.

The commercial ambition is also broader. Blond said Monaco charges more than legacy systems because it performs labor as well as software, and pricing follows platform usage.

Blond said software could be built something like 10 times faster than a few years ago. He expects that pace to keep rising, supporting a wider platform ambition.

Amjad Masad, Replit’s cofounder and CEO, said on Lightcone in November 2026 that customers should shape what gets built next. That offers a check on Monaco’s breadth thesis, not evidence against it.

Faster building helps only if new modules answer demonstrated customer needs. Otherwise, a larger product may add scope without improving the buyer’s outcome.

“We are disrupting labor.”
34:37

Our read

A broad platform could capture more value than a point solution, but it must prove consolidation improves outcomes. Faster building alone does not establish demand or attractive economics.

42:47

Creative marketing earns attention, but attribution stays thin

Monaco’s launch was designed for a concentrated audience. Blond said the company stayed in stealth, spent zero on marketing before launch in February, then used planes and billboards around San Francisco.

That play fit the geography of selling to startups, he said. For his hypothetical, he used $6,000 per day times ten days, or $60,000, as a possible learning cost, not an actual flight duration.

Blond said awareness lifted outbound replies and meeting conversion, but gave no controlled comparison or exact lift. That is an operator’s report, not a measured causal estimate.

His broader advice favors creative campaigns over paid ads in efficient markets, and spending in ways that benefit prospects. Take Monaco’s referral example, where he said the company pays $2,000 when a customer’s friend signs up.

That is different from paid advertising, not automatically better. Teams need to compare acquisition cost and customer value, neither of which the episode supplies for these campaigns.

Our read

Brand can make outbound warmer, but the episode cannot isolate its return. Early teams should test campaigns sized to their own audience, not copy Monaco’s spectacle.

1:00:41

Automation should return time to people, not remove them

Monaco’s AI promise is to automate non-customer-facing sales tasks, not put an agent in front of buyers. Blond listed account research, buyer identification, messaging, follow-up and pipeline updates.

That distinction matters. If software takes routine work, reps can spend time with customers and creative campaigns, but value depends on time actually returned.

Blond said B2B buyers still want a person on the call. He also described customer meetings as his highest-return use of time, a view from a founder selling sales automation.

His product pitch and work advice can coexist. Monaco automates workflows, while founders handle relationship-building and creative decisions that remain harder to delegate.

Dylan Field, Figma’s cofounder and CEO, said on All-In in October 2026 that AI makes production easier without automatically improving creative work. That is about design, not sales, but it reinforces Blond’s distinction between automation and human judgment.

The episode gives no hours saved per rep, adoption rate or incremental revenue linked to automation. Those measures matter more than a general promise of leverage.

“buyers still want to talk to a person.”
1:00:48

Our read

Measure whether reps spend more time with qualified customers and close more revenue per rep. Do not confuse tasks automated with value delivered.

1:03:16

Mapped buying steps turn interest into a real decision

Blond’s practical selling advice starts with a map from first meeting to onboarding and customer value. He said founders should propose a path, then ask buyers to add security, procurement or legal steps.

For example, a trial could run for two weeks with agreed outcomes and scheduled check-ins. The point is to set the next action before the call ends, not rely on vague follow-up.

Urgency is defensible only when capacity is genuinely constrained. In Blond’s example, three pilot spaces are available and two are already spoken for, but he said not to mislead buyers.

Demand connects this advice back to pipeline. Blond said abundant pipeline lets sellers walk away from poor fit instead of clinging to a polite but unlikely buyer.

He also reported multiple cases of old leads revived through Monaco’s follow-up, but gave no count or conversion rate. That supports persistence, not a repeatable sales result.

“you and the customer aren't flying blind.”
1:04:40

Our read

A clear path makes buying easier to evaluate and exposes weak fit sooner. Measure honest capacity-based urgency and persistent follow-up separately from customer value.

What it means for you

  1. Track lead quality. Review qualified opportunities, conversion and closed revenue per rep together. Segment results by buyer and company type so volume does not hide weaker leads.
  2. Baseline workflow time. Measure hours spent on research, updates and follow-ups before automating them. Compare time returned with customer-facing activity and revenue per rep.
  3. Run a campaign test. Choose a defined audience and a campaign that benefits prospects directly. Track replies and meetings, then compare results with the spend and effort.
  4. Map the buying path. Write down each step from first meeting to customer value, including buyer approvals and pilot outcomes. Track stalls, disqualifications and completed purchases.

What to watch

  • Whether Monaco reports time saved, revenue per rep and retention alongside usage-based pricing.
  • Whether an AI-native sales platform expands beyond startups while showing better outcomes than incumbent workflows.
  • Whether larger lead volumes preserve qualified opportunity share and closed revenue per rep.

Send this to a founder or revenue leader setting pipeline targets and CRM strategy.

12:13

Watch the minute where Blond says doubling leads can be easier than doubling conversion

Written by Real Alpha from the episode's transcript and the other moments it links, then checked against the transcript. Quotes are the speaker's exact words.

Minute by minute

  1. 0:49Company quality compounds early

    Blond traces his sales career from EchoSign, where he started as an SDR and moved into senior sales roles, to Zenefits and Brex. He says joining a strong company at an inflection point can matter more to a career than title or compensation, and that sales was a good fit for him.

  2. 5:27Ambitious goals create urgency

    At Zenefits, Blond says the 2014 plan called for growing from near zero to $10 million in ARR, then Parker asked the team to model what it would take to reach $20 million. The team later adopted the higher goal. Blond says this kind of exercise can expose what needs to change and manufacture urgency.

  3. 9:38Pipeline beats conversion gains

    Blond says founders often blame missed targets on a deal slipping when they should ask whether they had enough deals in the pipeline. For companies with a large addressable market, he argues, doubling leads can be easier than doubling a 10% conversion rate to 20%. He prioritizes revenue closed over a rep’s close rate.

  4. 14:07Strong teams and brand drive GTM

    Blond credits go-to-market results at Zenefits, Brex and Monaco to strong teams, and says he brought EchoSign colleagues Matt Plank and Jameson Young to Zenefits. At Brex, he says, loud campaigns aimed to make the company familiar to nearly all of its target market. He also says Brex invested early in revenue operations to identify which companies and buyers were most likely to convert.

  5. 20:57Founders Fund led back to building

    After Brex, Blond says he felt satisfied with what he had accomplished in sales and wanted a new challenge, so he joined Founders Fund in 2022. He gravitated toward incubating companies and co-incubated Monaco with his brother. Blond says building Monaco proved a better fit than working as a venture investor.

  6. 27:47AI creates an opening for a new leader

    Blond argues that Salesforce faces an innovator’s dilemma because its platform was built before AI, while Monaco is designed around AI from the start. He says Monaco can begin with startups, which account for less than 1% of Salesforce’s revenue, build a foothold there and later move upmarket. He expects the sales category leader to be built with AI in mind.

  7. 31:19Monaco wants the system of record

    Blond says Monaco chose to be a system of record because he sees the category evolving from a database CRM into a revenue automation platform focused on outcomes. He argues that point solutions have not produced the same kind of generational company outcomes as systems of record. He also wants Monaco to replace labor and multiple sales tools with one platform that shares data and takes action.

  8. 37:49Pricing follows platform usage

    Blond says sales involves more judgment than functions such as finance, so Monaco takes opinions on whom to contact, when to reach out and what to say. That can help startup founders who lack deep go-to-market experience. He says Monaco prices according to platform usage, which he expects to correlate with customer impact and revenue.

  9. 41:38A concentrated launch amplifies brand

    Blond says Monaco stayed in stealth through its design-customer phase, then launched broadly in February after spending nothing on marketing. Because its startup customers are concentrated in San Francisco, he says the campaign could make the brand visible through planes and billboards. He also distinguishes broad brand awareness from targeted efforts, such as reaching specific founders with gifts or events.

  10. 49:33Creative campaigns earn attention

    Blond says Monaco’s plane experiment cost about $6,000 a day, or $60,000 for 10 days, and generated enough attention to justify flying it longer. He recommends trying campaigns regularly rather than defaulting to paid advertising, and favors efforts that benefit prospective customers directly. He cites $110 poker sets and $2,000 customer referral payments as examples.

  11. 58:24AI frees time for human selling

    Blond says AI can handle tasks such as building a database, scoring accounts, finding buyers, writing messages and updating pipeline. That gives founders and salespeople more time for customer conversations and creative campaigns. He says B2B buyers still want to speak with a person, not an AI avatar.

  12. 1:02:25Give buyers a clear path

    Blond advises founders to lay out the steps from a demo to onboarding and value, then ask buyers to add any security, procurement or legal requirements. He says scheduled milestones keep opportunities from drifting after a promising meeting. He also recommends stating genuine limits on pilot capacity to help interested buyers make a decision.

  13. 1:06:50Abundant pipeline enables selectivity

    Blond says a strong pipeline lets founders stop pursuing buyers who are unlikely to benefit and focus on those who are a good fit. He says Monaco’s AI can re-engage old prospects, including companies that had seen a demo months earlier and later returned ready to buy.

Published Jul 14, 2026.

Transcript · 59 min read

Uncapped, hosted by Jack Altman, with Sam Blond.

Transcribed by machine (Whisper) from the episode’s audio, so a word may be off here and there.

  1. 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. 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. um so i actually first learned about you by reading jason lemkin's sastra blog back when i was you know starting lives trying to learn about sales and i remember in there it was like you know jason's talking about my best you know sales rep at echo sign and he did all 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 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

  2. we'll talk about lucking into some incredible company so uh jason and parker both of which you alluded to two of just like the greatest people but also um most influential people on the the career that i've had um and just like amazing advocates and close friends and all that stuff so shout out to those guys uh and um so let's see i 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 out here but for that. So then 22, moved to San Francisco, 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. I was there for something like six years. The company did relatively well and afforded 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

  3. into. But like, I mean, what a growth trajectory that was. Yeah, it was awesome. You know, 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 like towards the end, like sort of left turn into lots of lessons and we can, you know, it 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 dollars of revenue and then being able to leave when they were much, much larger and lots of revenue. Yeah. So we can spend the least time on this cause it's like reaching far back into the past, but like, what, 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,

Read the whole transcript
  1. what, what were your takeaways there? Yeah. Well, I think there was some, were you guys up against DocuSign? Yeah, that's right. So, um, DocuSign was a competitor. Um, EchoSign was private for like three or four of the years that I was there. 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...

  2. Nothing more influential early in one's sales career than the company that you join. And you control a little 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, you know, 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. It's arguably like we can, of course, 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 in 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 joined in a very early stage where you were like the first, the second, the

  3. third, the fourth hire in, in the role or function that you were joining in. Um, and then the path dependency on the career 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 that influenced my personal success, uh, as much as anything, I think there is like a different variable here. 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.

  4. I want to go to Zenefits. Parker, obviously one of the great founders of the last decade. And, you know, obviously, Zenefits in some ways, like, you know, he basically rebuilt Zenefits 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 Zenefits 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. Yeah. I joined in December of 2013 and then Parker and I both left around the same day, 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? 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

  5. Sam Blond · 3 min

    “Parker's like, well, we're not going to tell the board yet, but we're going to do this.”

  6. the business, something like that. Okay. So you have these ambitious goals for the year. So then like what goes into that? Like when you said, okay, what does need to be true to go to 20 instead of 10? Like what's the, what is that conversation? Well, I think one of the things that we benefited from quite strong product market fit at Zenefits. We benefited from the same at Echo Sign, at Brex, now at Monaco. And so then I think that's worth highlighting. I do think that there's like something that we were pretty deliberate about at Zenefits that I took with me to

  7. It was both amazing and, you know, difficult in all these ways, which, you know, are well documented in the end. but then Brex was like this amazing run. So you've now had the Ecosign experience. 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?

  8. Well, I'll touch on the two things that I think... Actually, the three things that influenced

  9. Sam Blond · 5 min

    “what are the companies and people that are most likely to convert”

  10. Yes. One of the things that I'm curious about is for Brex, obviously you had, and this is true at all these companies, but Brex, there was this known highly competitive market with Ramp. And I'm curious about, and I would say today more than ever, basically every founder is operating in an extremely competitive environment. Like, I think it's felt this way for a long time, but like, it really feels that way.

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

  12. Uh, so 2018, 2019, even 2020, um, it was, um, mostly a one horse race. There was a company called Divi that was acquired by build.com a little later. So there were other players in the space, but Brexit was always like, um, the market leader. Um, and then I think dynamics of the market evolved, you know, starting in, let's call it 21, 21, and then certainly, uh, beyond. And I actually, what was, um, uh, not with the business, um, for, for much of that period of time. and then Uh, Peter has this, uh, uh, saying that's like fairly, Peter Thiel has a saying that's like fairly famous. Um, that I think like it is oftentimes to your point, hard to apply to enterprise software that is seemingly like inherently competitive. This competition is for losers. And, um, gosh, like, uh, uh, 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, I said this, uh, term, uh, previously as, as greenfield environment, um, pretty smooth sailing.

  13. Yeah. 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. Yeah. 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 a monopoly as we can and then evolve from there. And I think there probably are learnings 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. OK, I want to come to that before we do after.

  14. So, you know, this like obviously extremely sort of like this rich journey through sales after that and before Monaco, you did spend time at Founders Fund and you have like a new chapter to your life that was not about startup sales. so like can you talk about what that was that experience what you learned why'd you come back to what you're you know a new version of what you've been doing yeah well look um i i've you and i have both talked about um jason and parker i'd be remiss if i didn't mention something about like the learnings from pedro enrique michael who is ceo now ceo at a company called figure um and so like equal sort of parts inspiration and then um uh let's see gratitude for for the influence that they've had on my career as well. And again, just like every single time I have been so fortunate in 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, we're 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 can get a little bit personal on like my mindset after Brex. So this is late 21,

  15. early 22. I'm reaching like my four year sort of tenure at Brex. COVID. It is COVID. I'm in Miami. Yeah. So I've moved to Miami at this point. And, 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, but I would effectively lead go to market at a company. Just like definitionally, the probability of joining an earlier stage company that has a Brex-like outcome.

  16. You know, 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. Like I wanted a new challenge. You know, 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 he was a VC at Sutter Hill. I mean, so I had seen him make this transition as, you know, like former sales leader.

  17. 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. world. I'd sort of be silly to not like take advantage of that. And so mid-late 2022, I joined Founders Fund and like couldn't 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. We weren't deploying a lot of capital at the time. This is like 22, 23. And I think like I'm, at the time, I'm Miami-based VC. It was a little fish out of water. And so I don't know, you know, I talked about like, I did this thing at EchoSign and then beyond that I could just tell, like, this is a good fit. I don't know, certainly being in Miami, but I don't know that like being in VC 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

  18. General Matter and Dalian with Vard and more. And so 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. 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 um the other day just like uh about like you know 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 um yeah was that like uh it feels to me almost like you had this like very busy career it almost feels like you took a breather and then you're like i'm going back into the coal mines? Potentially unintentionally, meaning the take a breather. I think what you said is exactly correct. And it could be received negatively, meaning today I don't have many hobbies. And if I'm not literally in the office, I'm thinking about Monaco and doing something sort of related to the business. I think it's very lucky to be so immersed in something that you don't have any hobbies. I think that's like a blessing. Yeah, no, it was certainly a deliberate

  19. decision. 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 correlated both with the place and the 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, I moved back to San Francisco. I live right by the office. It is, um, a high, high contrast chapter to chapter though. It is, it is, um, uh, uh, one 80 like, like, um, fairly STARK contrast. Uh, 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, um, so this is why you started a company, like why this company, like, why, why was this the one that you're like, I mean, I guess it's a a little self-evident, but like what was in your head where you're just like, you know, this is going to be what I'm going to do? It wasn't part of the plan. Meaning I had joined Founders Fund to be AVC. I didn't join Founders Fund thinking I was going to start a company, move to San Francisco, actually become co-founder, CEO of the Founders Fund. Right. And so I started this company. It

  20. like was just pulling me and felt very much like this is so obviously what I should be doing in my calling. So I think part of it was 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. And we are in the sort of early. things 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.

  21. Yeah. It's like this paradigm, you know, in some ways seems to be like, 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 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 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 it's just dominant to customers and the old companies can't seem to catch up.

  22. Sam Blond · 3 min

    “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”

  23. record. You didn't have to do that, but you made that deliberate choice. I think to the extent where you won't integrate with the system of record, even though you obviously could, you can imagine a world where you chose to do that. Many other companies, right. Because it's easier

  24. to say, look, I'm not going to try to 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. Why'd you choose that? That's right.

  25. Sam Blond · 6 min

    “the cost of building software is trending to zero. And so we want to take on as much scope as we possibly can”

  26. what you're selling to customers, in some sense, I guess, you're kind of selling 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

  27. 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 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. It's even more pronounced, I think, in the world of like finance and accounting where there is like 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 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

  28. signals that we're leveraging and how does that be incorporated into messaging and these things that many of our customers 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 yes um and then meaning that you're helping 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 that kind of like what you're selling to the customers.

  29. Yeah, well, we're certainly running on Monaco. And yes, I think customers hopefully benefit from the opinionated nature of the platform itself in ways that if you think about our customer, most of them are startup seed, series A. They don't, as founders, 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, these are 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.

  30. 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, outcomes are relatively objective when it comes to the category of like go-to-market or sales. It's revenue. How much revenue are you generating? 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 um that is like fairly easily measurable 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 and we talked about this with brex but definitely like you flipped a bit and like everything everything was loud so like what i'm curious about is can you sort of um share what was in your head when you're like okay it's time to launch we're gonna be loud here's the things we're going to do to sort of like get this whole brand going? Yes. Uh, I think, um, I'll describe

  31. Sam Blond · 4 min

    “They have heard of Monaco because they've seen the plan, whatever the thing is.”

  32. about maybe like a couple marketing principles that are things that we apply to marketing.

  33. I would love that because, you know, like one of the things I often think, I don't think this applies to every startup, obviously, or I know it doesn't apply to every startup. 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. 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... But there's a version of it for almost everybody. 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 most companies do not follow. You've got to try stuff. 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.

  34. I do think that on this point, it's a lot of people 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. 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 a founder. I'm an engineer. I build product. I like I'm going to index on the thing that I'm very good at.

  35. I don't know how to do like a marketing campaign. Which is funny. You know, our CTO at my co-founder, Eric at Lattice came up with by far our best billboard, which was like investing your people, not crypto during 2018. And that just like landed super hard. and that engineer yeah yeah uh so I'm not, I'm bad at this, so I'm not experiencing this or whatever. I don't spend the money. 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.

  36. You 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. Uh, and just ideating on this. And I think that's hopefully a high ROI to our customers. Um, and you can do inexpensive campaigns. Uh, like one, you don't have to be an expert at this too. Um, 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. Um, you can do a test, send this to 50 people. You're spending $5,000. It's like, um, Now, if you are truly bootstrapped and have no dollars to spend, sure, you can't do the $5,000.

  37. But you can still do stuff. There's always stuff you can do. 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 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 the whiteboard and just do it.

  38. 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 um are in this like category of marketing brand awareness demand gen however we want to frame it uh and i think we really want to be um contrarian is maybe like not the right application of that word but we do want to be creative new stuff 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 right now we um there there isn't we took it down we'll put it back up at some point uh i think like probably reached diminishing returns or something over time but it was like yeah anyway go ahead yeah we we were at saster which is um jason limkin's conference awesome conference uh and we knew that there would be like a large contingency or concentration of people at this event down in san mateo and so um we 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

  39. same event 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 yeah 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 six thousand 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 uh do you guys like 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 math on this thing and it was like six thousand bucks a day pay for 10 days it's 60 grand 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, it's a $60,000 learning. Like the worst case scenario, we fly this thing around. It doesn't totally work. We like learn from it and we don't do it again.

  40. It worked. So we, you know, both like 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. And so it was one of those things that was like just an evolution of something that we had tried at the conference. Let's like try it in the city. It worked in the city. We learned from it. We'll put it up again when we do a big like announcement that we have coming up. Yeah. You know, it's interesting, like history kind of, I'm sure you've read Behind the Cloud, you know, the early Salesforce book from Benioff. And like one of the things that like struck me was like early Salesforce did a lot of really creative marketing they did really creative and like some of it was that the message was creative like the no software thing it's like well you know that's interesting you know there was a lot there and just like the way they even did like customer dinners you know i think was like kind of creative and you know it's like all became sort of like tried at some point but like being the first to do a good go-to-market idea is worth a lot it seems like i think they're um the one that i understand as much as any was like the the protest it may be like a big siebel or

  41. oracle conference where it was like the no software um which i think was uh really smart yeah so like when you're thinking about this are you are you like i'm gonna do new activities and then i'm gonna put them on some back burner or you like i just have to always be like do these things stack and build over time or are you just like i gotta always have a new thing there are

  42. Sam Blond · 6 min

    “Early on, I would try and bucket like 100% of the marketing spend actually to something that benefits the person that we are targeting.”

  43. guess of early startup go to market is like the ground game and maybe just to wrap you know this conversation can you talk about your sitting like that was like a very good illustration to me of like if i'm like a monaco customer like and i'm meeting with you like i can now like immediately imagine how i'm going and thinking about doing doing that the ground game side where i'm like okay now i also need to do the sales calls and build the early machine and i'm like a series a or late seed stage founder with early go to market but i've got like you know a handful of reps or two reps or 10 reps or whatever. What are the principles you're teaching me or talking to me about as a sales org builder? Yeah. Well, first, maybe at a more, we've already used this word in a different context and more like meta level. I think that there's something that is worth maybe touching on. It is like, how should we be applying AI to go to market? And then what does that give us leverage to focus our actual time and energy on, which is the thing that you just talked about.

  44. So backward looking, I think most labor in the sort of like category of startup go-to-market was on what I would describe as workflows that today AI is actually better at doing. This is like building your TAM, scoring your accounts, overlaying signals, finding buyers, writing messaging, all of this like fully online. workflow orchestration that agents are just better than any human in the world at. And so it is true that that is like what Monaco does for you. All of this sort of like non-customer facing sales related activities, building your database, scoring your accounts, finding leads, engaging with buyers after you finish a meeting, updating your pipeline, reminding you who you need to reach out to, all of these things. And what that does, whether it's Monica or not, it allows you to spend your time on higher ROI, higher leverage activities. I think there are two categories. One is, and this is the thing that I spend all of my time doing, but it is meeting with customers.

  45. Today, especially if you were in like B2B, 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, maybe on, I would suspect, our customers' time than spending time with customers. And a lot of the things that we're able to leverage with AI allow us to spend far more of our time, whether you're a founder or a salesperson, on that human connection, developing relationships, customer facing. I think the second thing is this category of creative, operationally complex campaigns. We've talked about a bunch of them. You could do like a chat GPT conversation where you're like, can you come up with some marketing ideas for me?

  46. I think it would be hard for that to result in the plane, as an example. I think that today, AI will sort of pattern match to things that have already been done because that is what AI is trained on. And so if you are trying to do something like truly creative, in of one, innovative, I think it is more likely to surface inside the four walls of your company by doing the sort of like ideation that I talked about, which is let's come up with two ideas, each person multiply by four, that's eight ideas, put them on a whiteboard, talk through each of them, pick the two or three, the best ones that we're going to do. And Monaco and AI actually give us the like ability to spend our time doing those things that is how I spend my time with customers is is the less about the sort of like how should you be meeting with customers I do like how should you sell those sorts of things but it's coming up with like creative campaign ideas count me in as like one of the people that comes up with the ideas that we put on the whiteboard yeah that's awesome um and then I guess like on that last piece is there anything um worth talking about in terms of like how to actually sell or like the practice of, you know,

  47. Sam Blond · 4 min

    “Because if you aren't educating the buyer on how to onboard, receive value and ultimately buy your product, the customer like doesn't know how to buy your product.”

  48. Like, I better speak up to like, you know, get this thing that a lot of folks are already incredibly interested. I assume also important in all of this is sort of just like having like a willingness to disqualify when you genuinely think that the product is not going to help the customer. And I think people can feel that. Like if you're like, hey, my goal here is not to sell you something that you don't need or want. My goal is to sell you something that's going to be useful to you for years. And so if I don't think that that's going to be the case, I'm going to stop selling it to you.

  49. Man, when you say that, it's interesting where my mind goes, which is something different than what you just said. But I think it is true that growth solves a lot of problems. I think an input to that is something like demand solves a lot of problems. And what you just articulated, I think, is a symptom of not enough demand, which is where founders and salespeople are hanging on for dear life to the one guy that I pitched over the last couple of days because they kind of seemed interested. That's right. But if you're like, I've got four more calls I should get to, and I think this is going to be painful. And by the way, I get paid also on you retaining. And so like, I don't think I want to sell this to you anymore. You can, Parker, I stole this from him. You can sort of swipe left. I've never been on one of the dating apps, but I think Tinder, you sort of like swipe right if you like them and swipe left if you don't. And so an abundant pipeline allows you to only try to sell the product to people who need it.

  50. That's exactly right. And it's not, when I say that, it's not like disrespectful to the customer or being inefficient about not following up. It's actually that like you are focusing your resources on the people that are truly interested that will receive the most value from the product and not on the like person that took a call that was like said a lot of niceties. Yeah. But like actually probably isn't actually interested if we're intellectually honest. And by the way, a lot of it is like a not now, but you know, let's come back to this. if you're like oh we have so many customers if you're like if it's somebody who's like you know i am just getting started i don't really have product market fit yet i don't have any reps you know i'm interested you might be like if you bet like sure if you want to buy it now but like it might be better if you bought this in six months once you're going a little bit we're we're four months in um four or five months in uh launched in february and um monaco does an awesome job of continuing to engage with older customers on our behalf. But I cannot tell you, well, I can tell you the amount of times where I'm just sitting there and resurrected from what effectively

  51. is The Dead, a company that we demoed back in February that Monaco sort of re-engages with on my behalf. Response comes in. I see the response and it's like, I'm ready to go. And again, all of this stems from more demos in February, right? And so I think lots of sort of anecdotes of what a demand-rich environment evolves to. Sam, this was awesome. I learn a bunch every time we talk. Thank you for doing this with me. You are the best. Thank you so much for partnering with me on Monaco. And it's just an absolute pleasure to come on the show. So thanks for having me.

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