20Sales: How the Best Sales Teams Use AI to Win Enterprise Deals | Sales Teams Will Be Dramatically Smaller | How to Ramps Sales Reps Way Faster | Why Unpaid Design Partners are BS | Why this Generation of Sales is Soft with Ishan Mukherjee @ Rox

23:22The job is changed. The way you do your work has changed and you hope to have them evolve and thrive in the modern economy. If not, it is an existential decision. On sales, specifically as possible, how has the job changed in the way that a salesperson works. So there's two phases of SSLs person. First, you ramp to the job where you learn up how do you actually do the job. And then while you're doing the job, you're trying to hit or exceed your targets. In the ramp phase, what you used to take to maybe two and a half quarters to run a rep where you're reading everything about the customer, about the product, and you're getting on with it.

24:00If you're a really savvy person, you go to perplexity, you go to charity .gbt, hopefully with rocks you understand everything about the customer everything about what you're selling and really ramp much faster So you're talking about gaining a quarter quarter and a half. How do you ramp fast? What is it that allows you to ramp faster? It's deep research understanding kind of pain and kind of building your own internal frameworks of how to communicate Your kind of solution to the pain Which at the nitty gritty of it is the game of sales hasn't changed for a long long time Like what people used to do is print out 10k, 10qs, SEC filings, read every CEO transcript.

24:38Now you can do that on your phone in a few days. It's just reducing the time to do research and forming your opinion. Do you think people know the research they need to get to to get that information quickly? The best, too. So Rox focuses a lot on enduring enterprises. We work with large, legacy, some old school enterprises. When you spend time with 20, 30 year vets who've been selling into automotive or airlines in Europe, they get it because that's the only way to earn the credibility to even get a conversation. Kind of let alone kind of move pieces. What has happened in the last five to seven years is people think this is easy.

25:13It's not easy. You have to be kind of a consultative expert in the customers business and you have to do the research just like you all do on founders and that's the only way. Like we call Manav before hand in us and tons of questions. I totally get you. Do you think we have a generation of salespeople who are not ready for the challenging nature of sales that is to come? Yes, and it implies to most functions in venture founders, builders, we had it relatively easy the past four to five years. I want to be morbid, but things are hard. To winning is hard. It's hard to hard work. And if you look at sales specifically when everybody's spending and everybody's kind of buying.

25:58It became pretty easy. You're kind of becoming auto -takers or as they say, like shooting fish in a barrel. But when you're selling something new or selling something large, there's no easy way around deeply understanding the customer's pain and how to actually solve it. I'm seeing that constantly, like honestly, I can't really, like, we've done really well the last year. This taken me maybe two to three months longer to find those out there sales reps. is because it was just pretty easy. I was like, you didn't need the outlier sales reps because people were spending so freely in sales cycles was so compressed.

26:30I totally get that. There's so many areas that I do just want to dig in. You said that like segment one is the ramp and the compression of ramp from two and a half to maybe one and a half. If I'm a sales leader today, listen into this. What can I do to reduce the ramp of my new reps? Give the power of data and tools to them and reduce friction. What does that mean? That sounds wonderful. Exactly. So very basic things. Most sales reps in the world use chat GPT perplexity LMS in their private life, but they can't use it in the professional life because of data access problems. Data access These seem simple things like I think the words change just give them access to their tools.

27:10Second is when you think about how you train onboard folks. It's very similar to schools versus teaching your kids to YouTube which is you've got to completely change how you train people by making it more kind of AI enabled and so that you basically get them in front of deals, give them life customers, versus having them going through like two to three months of basically old -school training because that information's still. How do you think about how quickly to put wraps in front of customers? Customers are precious and must treat them so carefully. If you put a wrap who's kind of not ready, it may not be the best representation of your company.

27:44Yeah. How would you advise me? This is where I'm not the expert for scale kind of go and market because I kind of lean in like even early stage My mind says still the same which is get them in front of customers with mentorship as fast as possible So what I do in early stages After a few weeks you have to shadow a ramp A or myself Without being in that room is just really hard to replicate what's happening in the world like the words is moving too fast give an example, we have a capability where you can basically do deep research in your customers. Four weeks back, people were like, wow, by what we had.

28:21Three weeks later, deep research launched. They were like, oh, no, I now expect PhD level research. And if your training doesn't keep up to taste, if you're not in the front line, you just won't see customer expectations change because they're changing every day. So my general mindset is, hire somebody in the first week. I have a sense that if they're based on the questions that they're asking, whether they have it or not. What are those questions that make you reflect and think they all great candidates? First is not. So there's questions that they ask me or us and then there's questions I ask of them.

28:53And the questions, if they are asking us to deeply understand the psychology of the customer and the buyer, things like, hey, what is their expectation? What do think of you? I do those are really good questions because the thing that you have to really understand is what is repain, what is their propensity to buy or sell, but now deeply every consumer's expectation of software has changed. Where are they in their journey? Do they get it? Are they early like those questions are important versus any boring discovery question, right? All consumer expectations high when you're selling into the biggest enterprise is like you do.

29:27When they're traditionally walking off pretty shitty legacy enterprise software in their professional lives. Right, so this is the first time I'm seeing what they're doing in the personal lives carry over to their professional lives. In the personal life, they're teaching their kids with Chagypeti Anthropic. And now they're coming in and they're expecting it totally differently. If you look at the intent logs of how people are using rocks, they expect software to not just do some work. In some cases, they wanted to do all the work. Humans across the board, including my In Muhammad India, everybody has been, obviously, sold on the promise of AI and LMS.

30:04When they come into the workforce, they actually want the software to do as much work as humanly possible, specific where it is humanly. The software should do anything that a human can at scale. So that they could do more and more in my domain is support more customers. Why does it make sense for rocks to be verticalized versus people just use Chachi PT? Is data. The alpha is in being able to index all context about your customer. So I give you my CRM? Exactly. So Rockstrums in parallel to it. They need to love the way I invest in it. So how does this work? That's a very good question. But so I give you the CRM and then you get all of the company level data of all of my targets and all of my pipe.

30:48And that allows you to do what? Let me go back to the origin story a little bit because you brought up New Relic earlier. When I was competing head on with six or seven public companies, the difference what I was seeing in the trenches, when customers in calls where most account customer facing graphs were just not proactive enough. They knew a partial view of the customers, but they had no real time understanding of how much are they using? What do the support tickets look like? What are they looking to buy? How are they growing? Everything was not in the CRM. So they've kind of featured sales is how do you feed in real time context?

31:20Hopefully, I'll kind of complete context about the customer so that the human in front of the conversation is essentially super charged with this kind of bad suit and actually moving the deal along. So what we do is Rox gets installed in parallel to your CRM, how's part sales force dynamics. It runs in your warehouse. It indexes all internal context and brings in public context. And it's trying to do the work for you. So you have a team of Rox agents or a steam of analysts who are working for you so that you have full context and are basically moving the conversation along. Now I get it. Well, that was fantastic.

31:53I'm so glad. Totally made sense. What is the primary task that Rox does today for sellers? Absolutely. So today it does all customer research and prioritization. So we're doubling, should playing the customer's books. And now they have 10, some hundreds of customers that dealing with it. So it does all the research and prioritization for them. So now I can outbound way more effectively with way more personalization. Absolutely. The second is outbounding. We're the anti -ISTR. My my -kind of view on automation is the human evolved to become an orchestrator or a quarterback. So we do all the work of composing your sequences who'd reach out to, but the human reviews and sense.

32:28This year, we look at this data pretty closely. We're not at a point where a CEO or a CRO can just just fire on the hole, kind of fill the pipe with these kind of outbound systems because it's going to die later brand. On the outbound, we basically do compose all of our outreach with a human, kind of reviews and sense. That's the second part. So it's called Rocks Outreach. After that, when you do reach out, it does all your meeting work. So it does your pre -meeting research and meeting support follow -ups. Again, the mindset was, let's just call it a bomb or like a precedent. Before you go into a meeting, you usually get a brief, like a folder, which everything lined up, that's what you want to do is.

33:05What if you had every knowledge worker had a team of analysts who are basically preparing you to be the best version of yourself? Why is this just for RAPS, so this is basically the helpful VCs? So we have a tens of VCs on the platform. And 100 % we're pretty maximalists in terms of where systems like these could be helpful. We think deeply about what's going to happen to knowledge force across the board. But today we have some of the best VCs, hopefully, as well. like using us retune our agents based on the context. So like the email that it drops is not really trying to connect convince a founder to take a meeting or like those are things that we have to do but it's completely feasible.

33:43Demo is and Twitter DMs as you know is fine. In a world where you have this infinite supply of outbound emails because you create it and you're able to do so much more, does outbound become less effective when supply becomes infinite? Yes. Yes, and yes. So supplies infinite does yes, it becomes less effective. What our view is, how do we make the communication authentic? So very basic thing. The email needs to come from your email. Second, the email that comes out should be personalized in your voice and tone and then you should probably review it. And that's the only way to actually write about the noise floor because noise floor is increasing.

34:21Like exponentially, everything else just will not work. So second thing is you can brought up like multi threading and kind of talking through The key thing is the human has to create a human connection and one email is not going to do it. It usually takes 13 to 15 touches. So, emails, LinkedIn's, meeting them in person, getting on plane, as Jason says. So, again, our idea is how this is going to swarm of agents, help you kind of produce the content, but you have to really put in the work to have those touch points. If people think that you can close enterprise deals, but having one email go out, that's not going to happen.

34:52You mentioned earlier, everyone's spending in a prior generation, and how it impacted actually the quality of sales reps maybe. There is a real belief today that we are seeing this massive contraction in spending. Are we seeing CFOs span less and consolidate more? Consolidate more, yes. The definition of spend what I'm seeing is changing and is changing from program to people. What I mean by that is when you look at traditional SaaS and I was saying you're really going to have been in this space for a while. I was thinking about Cs, you're thinking about productivity doing and basically selling from from the IT budget.

35:25Now, a lot of sophisticated buyers are looking at systems, hopefully like rocks as well, is he can I just make my humans a lot more productive so that I might not have to hire as many, just kind of brass stacks, right? So it's their view of kind of the ROI is changing from ROI on just software to kind of the people's pen. So what we focus on is we want to be the only, for right now is we only convert if we hit our ROI metrics. We run a 30 day white love like palantir like kind of boot camp where we work with the CFO the CRO and the C suite on Three metrics the first one's dollar normalized outcomes.

36:00Well, that's pipeline generated or progressed The second was adoption third ones activity Like the system needs to return all three if not you can fire rocks. Right. What is it number one? Number one is some dollar Normalized outcome. Yeah, it could be they choose pipeline generated pipeline progressed. What do you prefer? They choose most a pipeline progressed, like because these agents are really good at making sure a human can manage a larger book of customers really effectively. If they have tens or hundreds of customers, because the agents are doing most of the back office work, is doing the research, is outbounding, is prepping for meetings, managing opportunities so that you can actually like engage.

36:39Number two, adoption. Traditionally, the adoption about a lot of these tools, they're abysmal. Like the NPS scores until so we kind of index ourselves in pretty aggressive We've hit 75 % weekly active usage is bit more than 50 % daily active So like we want to be the daily driver application. You want to be daily active daily active. Yeah closely Like we have an IAS app we have a slack like we really want to craft like the application that people use to do their work So we index if people aren't using it you can remove us What are the reason why people have not fallen in daily activities with you?

37:14Three things relevance is our agents. It is an agent XRM, these agents are trying to do a lot of the work for you. So it collects all the data, finds relevant opportunities to reach out, and then tries to compose all the throughout the region. Because we just got pulled so fast out of us like Roxas, that's a little bit honest. It's public, it's open, but with still pretty early, if finding relevant moments to actually reach out to customers, is actually a pretty hard engineering problem. Oning's coming out might be interesting, might it not be compelling and afraid to actually reach out to those customers?

37:47I find the most compelling moments are actually personal posts on LinkedIn. Exactly. It's like, hey, my daughter just graduated from Brown, and this is a picture of the commencement. And just that like, oh, I was at Brown, you sent an email, I remember my day graduating at Brown, and they're like, oh, wow, I like your show. Exactly. So you're going to hit on, you should be able to hit a product as well. Give us a lot of feedback. is removing from company level insights to contact our human level insights. And that's the joint. That's the number one piece. The second thing is it is in net new form factor, net new UI.

38:20Like if you look at our product in UI, it kind of looks like a CRM, but it's actually a summer of agents working for you. So there's a new paradigm of UI or UX, which is between a chat interface and a traditional like flat SaaS experience, where this is kind of more task oriented. And that's where we're at. So the history of rocks is the pretty experienced team the first three to four months We built a god mode agent that knows everything about every customer with a chat interface This does not work. Do you think in challenge face is the right interface for a nice wave of AI and AI I don't think I'm pretty pragmatic because we have to be very iterative on the interface level We're really opinionated about the backend and how to manage all the context But in the front end like we just have to really try to track the consumer expectations What we learned was chat interfaces are very powerful but we're very limiting to do daily work.

39:07Why are they limiting to your daily work? Because our kind of end users expect this after they do work, so they essentially want to work flows. Right? So if the agent went out there and customer research, they just need all the customer research is listed, versus them asking, hey, tell me this, tell me that. So we have account reports and org charts created for them. Similarly for outbound sequences, instead of you going and saying, hey, produce an email, we just queue up all of your email tasks. So these are these places where the software does have to lay out its outputs. Like chat is an interface for them to do more introspection and go deeper.

39:41So I'll give you every simple first, which I'll go chat with just a blank Google bar. Next is give me pills. Give me suggested things to click on. Then you hit pills like, hey, give me more output panels. And those things work really well in consumer applications like perplexity, which is amazing about the product. But in a B2B software where people are coming in to get job done, we have to just do more. So what we did is we decomposed the experience to a part where we have essentially kind of workflows designed for the job at hand. So we went like build better check style, like what are the jobs to be done?

40:16How do we actually kind of organize it that way? Like meetings, separate and email, same as the separate and account research. And like the adoption just completely was insane. We go from the few people using us to the whole company using it very, very fast. And again, like, is that a terminal state? I'm not sure, right? Like, I think we'll be creative on the UI UX. We, yeah. You mentioned adoption that. Are we about to see a wave of the most unprecedented churn in enterprise AI tools? Churn and retention is the one thing that keeps us up at night, like the biggest thing. I think it's actually a six month old day, but it's like, it's like, Dean, like we've chosen the hard part, is we want to be on the Mao -Wao Dow train and build applications where people come in and do important work every day, which is not easy.

41:07I think where people are going to die off is in terms of usage is if they just lose trust. What you have to understand is these products are inherently not deterministic. These are probabilistic systems. So the experience, the research out with that you get for say your Siemens agent could be different, what I get from Siemens agent, it's the other lab trying to figure out was relevant to me. And if the end user sees something that's not good, it's gonna kind of shave away like some of their trust. And if it gets to a point where like, I just can't trust this thing, I'm not gonna come back. That is the biggest thing.

41:41Is there going to be retention and churn issues from an end user perspective? 100%. We're seeing so many tools coming in out. Do you think we're still in the experimental budget phase, and the advantage price is buying AI tools. There's massive amounts of experimental budget. We've made the decision of not tapping into it at all because of the focus of retention, usage adoption, or why we only work with customers from their operational budget. Program, now kind of people budgets. That's a way for us to control be true seeking, but we are in the very early stages of the adoption curve. What I see is small group of outlier operational CEOs, CO, CO, CFOs who really understand that there is an existential decision to be made this year, to transform the business, to kind of keep their lead.

42:26The rest are still figuring things out. When we think about bluntly giving agents to every sales rep and allowing a swarm effect so they can be so much more productive and efficient, will sales seems to be dramatically smaller in the future? Yes, dramatically smaller. Just like engineering, just like any other function in any business, it could be 10 to 20 % of current kind of org sizes. And it's just harsh kind of reality, but that is a probable productivity gain path we're on. And it's tough as brutal. And I've seen like I've worked on automation systems all my career, I build robots in warehouses, like the company that Amazon acquired.

43:04Like we've seen these things happen all the time. And the 10 to 20 % that retains is the human to human that gets on a plane to Dallas and comes and shakes your hand and says, this is a shame I can't wait to work with you. That's why I'm here in London. I think Jason's point is important is those folks who are there to build non -transactional, long -term relationships, add a strategic level. So high ACV deeper conversation, they will be able to do a lot more. They will be able to do two to maybe three times more this year. Like we're seeing some of the best organizations increase their book size.

43:37Hey, you would have supported five customers last year. This year maybe seven, next year 12. So if I'm a founder listening today, what can I do to dramatically increase the sales efficiency performance of my team with AI today? So first hire the right folks who are future proof, like they understand the word. So are they using these tools maybe illegally in their personal life? If they don't run using it, they don't see the alpha in their personal life, they probably not going to get it. Second is I might be completely wrong here, but ramp much faster because you can just do faster be the consumer expectations are changing too fast that you have to do so.

44:15Once you're fully rammed, push the envelope of how many customers that they could support. And those are the three things without obviously losing overall quality and entertainment levels. Will there be teams which are much dramatically smaller who are pulling in the same numbers? I think it has to be proven, but strong and an intuition that that's where we'll get to. Do you not kill data providers? When you And look at your Zoom Info, so as a well -perspective, I never want to choose that out, but your Zoom Info, or any of the others, you need them if you're supported by an agent's form. We didn't start rocks or this amazing company is working in this space, kind of deeply thinking about how to source agents, but the agents have got a phenomenally good at -scale gathering information that is in the public internet.

45:01And now systems like Lean and stuff in the internet or in the internal systems. So yes, the agents will get more and more capable to just collect information, especially research APIs and the access of the world. Having said that, the data providers, the provider of source of value, where they have 10 to 15 years of back -tested data of human contact information, LinkedIn information, that they've been verifying through a lot of software, but also a lot of operational rigor, that's really hard to replicate. Like Henry and Zuman, for example, a phenomenal business, they have probably the highest quality contact data.

45:35I have a huge machine that they basically like kind of built up to have that and you partner with them and you suddenly So when we go into a customer like our agents will go in rich contacts like if you have data of zoom in for data and Salesforce or whatever It's gonna go search and kind of verify the information and Internally, we have kind of OEM the few data partners in that we waterfall like Larry just to kind of bootstrap us So these agents today are enriching the information that you already have versus going and actually gathering it. There's a split company data is frequent. Company data is public, agents are pretty much at par.

46:10Contact data is where the diver just happens. Like if you look at what the question that you brought up is like LinkedIn information. Like LinkedIn is a world garden, rightfully so. It's an extremely kind of valuable network that Microsoft LinkedIn have. People who have LinkedIn data as a data product that they sell into is just a different world that we don't see ourselves going into. We chatted before actually about agent forcing, and they are a core competitor. When we think about who wins in this next wave, whether it's incumbents with distribution and just a lot of touch points like they do have, or whether it's your rock's of the world with speed, with innovation, with agility, how do you think about that trade -off and who wins?

46:47It's a brilliant quote from Alex Rampell. It's like, will the incumbent acquire speed before the startup acquires distribution? Yeah, he's spot on. Many of us are good. You respect him a lot. but I've learned so much from my AC read about this stuff way back in smart and India. Can our approach is just time to value? Like going back to the new relic learnings or just kind of being like a product folks founder is incumbent systems have data and distribution. They have massive amounts of work. From our perspective, but it takes quarters, system integrators to actually implement things to prove ROI.

47:19For us is how do we leverage our shipping machine to land something that gets started today and gives you ROI in an extremely kind of time in a compressed manner. And then we are in the right to can expand from there. So what's gonna happen is all the incumbents of obviously repositioned as AI companies, now our agent companies, and they're also all bundling. Like as SaaS exploded, there was massing and bundling across sectors, definitely in the CRM space, right? You have phenomenal businesses like Larry and Kong and Client folks. So they're all bundling and they're AI companies. We're in this bundling cycle.

47:51With us, we wanna be hopefully the default new option of an EI native, kind of bundled software provider, yeah. Now, when we think about kind of getting in the field, it's really difficult to put out sales team. I think the hardest thing in moving from found let sales to sales wrap let sales, you've done this before, but you're doing this now with rocks. What are your biggest lessons in the transition from found let sales to sales wrap sales that you are remembering today as you do it again? Yeah. Do you have repeatable sales motion or not? And are you being absolutely true seeking? What is repeatable sales motion?

48:23repeatable sales motion is, are you able to go from a list of potential customers to a high quality first meeting autonomously without the founder helping you? The second one is, can you go from a successful first meeting to landing the customer without extreme founder assistance? If you can't do both, you don't have repeatable sales motion. So in this early stage, where I do have to kind of grow really aggressively, what I'm looking at as the first part is, based on the case studies, these reference studies can an enterprise they come in, build their own list of target customers without needing a BDR team, without needing marketing people, and then go from there to the first meeting autonomously.

49:03Can I completely, can take a step back? After M1, we just have to be true seeking. Like, we don't have a massive brand, we don't have a huge demand engine. It's not perfect product market fit, liberally. Italy founder assisted. So that's what we're looking for. The working session that I do is, I'm gonna walk you through the whole strategy. Here's what's worked. is going to have you messed up. Here are our reference customers. How would you go about producing your list of people to reach out to and how would you actually get to like having a high quality first meeting? You go for a sales leader who brings in the wraps.

49:33You go for wraps who are more junior you train without playbook. What's that first step? There's different variations. I back myself to recruit, train and build the machine with five reps reporting to me directly and then bring on a sales leader who kind of doubles the team and takes it from there. in those reps, do you want reps you've sold that size deal before or sold in that segment before? Yeah, should have held the number at that ACV size for two to five years. Not less than two, highly not more than five. Within those, they need to show that they've been innovative in the pocket. Within deals, they either have built tools on their own or were actually creative in kind of progressing or closing the deal because early state selling requires a lot creativity that founders can come in and we can use investors and has involved, because involved to kind of paper over cracks but they need to be gonna creative.

50:24That's number two thing. The number three is just they need to want to make money. Right, like I really can't deeply think about the D -hole. You would be surprised that a lot of AI companies, AEs, are not compensated with commissions. Really? Yeah, a lot of them is especially in COVID. Like so I'd really try to get deep into, you do actually hold a number. What did your conversation look like? Where do you want to get to? Because it's kind of gets deep with the psyche of a person like the best ease are just have are complete owners They're owners of their own book not very different than a CEO then a founder and that's kind of the third thing I try to get to and that's kind of separates a lot of folks who are doing it because it was easy They also have real estate portfolio on the side.

51:04They're doing a lot of things like and so you're trying to like hone in on those kind of three things Bag has some experience holding a bag a real enterprise bag Second is kind of creative. Third is DT, hold a number. Like I'd go really deep into that. How quickly do you know if that good or not good? My interviews are long. I don't believe in 30 minute interviews. Either I believe in my kind of trust in on a network of folks telling me somebody's good or not. Or I do our and how working sessions. In the working session by, I would say the half hour mark, I can tell based on the quality of the question they're asking.

51:41I am coming into one of your working sessions. How do we spend my hour and a half? Try to overshare context on the Silicon Valley ethos. Don't hide anything. Just share what you're working on because if somebody beats you on your own game, that's on you. So I just share everything. Like, hey, here's the product strategy. Here's where we are here, customer case studies. That's probably about the first 30 minutes. So when I'm doing it, I'm trying to see the questions that they're asking. They might ask about pricing or case studies. What, what, what, didn't work? that could take a lot of time, like, 34 to 5 minutes.

52:10And I do that for every candidate, because that's some kind of understanding and how they would go about. Because that's where we want them to abstract it, build a list from there. Their brain should be running. After that, we get into specific scenarios. Okay, now that we want to do a scenario, let's say we're working a strategic deal, called a large company in Europe. If I gave it to you, how would you run this deal? And then I flip, then I ask them questions, like, what if this happened? What did that happen? So the first 30 to 45 minutes is me sharing context and them asking. The next 30 minutes is like them walking through a deal.

52:42The last 15 minutes is if we feel it, you're talking about next steps. If not, you rapidly. GG hiring panels, are you happy to make a decision after that 90 minutes? Yeah, I try to like founder led early stage sales, which is what customers and talent. Like you need to be able to make deals in the room. Again, a big difference between going back to obviously, I idolize kind of Dave and Mongo. and I'm at the liver data. If you look at these download machines, a lot of the times deals don't happen because the account team has to go back, talk to deal strategy, come up with some, the best teams are enabled with tools that they can make things happen.

53:16Like if there's some heat there in the room, so if a candidate has gone through it, I'm spending an hour and a half and I try to kind of progress things along. Raps get paid a lot actually in a lot of cases. Once you're taken on, hey, I'm willing to pay over market for the best. We pay market and then come, How do you think about lessons on that? So my framework is a framework of explainability. Like the idea is comp and how much money make people make an equity. I'm still old school. It doesn't need to be public. But let's say it did leak and we came public like everybody's compensation should be explainable.

53:50There should be a rational reason as to why somebody's compensated a certain way. So I have guardrails, explain everybody guardrails, I don't want to kind of breach because if you're giving somebody some irrational package and it leaks and is going to have like trickle down effects on the team and the company's the team the team's the most important part so what I try to do is if somebody's truly outlier and they've kind of venture the thing and they're really like capitalist and thinking about incentives very aggressive with performance based either compensation or equity grants and 100 % like the outlier victories happen when you go you break rules right I totally agree with you aren't you on the opacity of salaries I think people always view everything with the expectation that everyone's rational, and actually everyone's entirely emotional and human, which means they are irrational.

54:36And also they're volatile, so at some point they'll be like, that's completely unfair. I just signed a massive deal, and then when they've had a dry spell, it's actually a fair representation. Something that I'm worried about is you mentioned Target setting earlier, and you mentioned Jason Lampkin earlier. I grew up with the Jason Lampkin School of Thought for Founders, which is triple, triple, double, double. And we're like, you know, this is what you need to do get great rounds done. Truth is now, you've got your macaws, you've got your lovable, you've got your mid journeys, these companies are scaling to 40, 50, 100 million, I mean in 12 months, and I'm worried that we've lied to a generation of founders of what it takes to get great rounds done with revenue trajectory.

55:14How do you think and feel about that as the NAI founder today? Probably the most interesting thing for me to just manage my psyche around, I would say. The way I think about it is you're building something long -term and what matters is in the online revenue, high quality revenue from customers who can be with you for the long -long term and is the unit economics are the numbers looking great for that. Like for us is traditional enterprise land and expand. Are we landing the right logos? Are we landing them at a decent land ACV and the coin? What is a decent land? Obviously, you don't even know about it.

55:49Right. Okay. Like, low six figures and then really prove value. And we're doing that is a no brainer, quick land. We compete on time to value. And is there a path to high six figures, seven figures? And that's what we really care about. What do you want to see in terms of that sales cycle and then expansion time? So if it's apartment market enterprise, we want to be at 45 days from M1 to having another first initial land basically done and signed. And after it depends on how we can construct it, there's a one year contract with a 30 day paid e -valp period. Where 30 day the customer, I know there's a lot of discussions, and we're still beta, right?

56:28So enterprise are buying beta software. So we give them the right hand. 30 days, if you don't know how the ROI, you can downgrade to our premium product, or we can have a conversation. After that, it can convert. So once it's convert, then we're looking to deliver more value and can drive more expansion. So 45 days to get to the first land. And then we have the clock starts. First is we need to prove valium 30 days. After that 30 days, it's about delivering more value, kind of finding an expansion. And I think that's the, we've already had that six figure range and how do you kind of really kind of grow from there.

57:00Ultimately, we want to be the essential software system that's helping you secure and grow your revenue. So we want to be essential. Just like SAP is or Salesforce was. Totally get that in terms of the design, enterprise sticky revenue and building the injury and value in the long term and not getting caught up in kind of sugar high hype cycles. I actually tweeted last night, it's really unfair of me. I tweeted last night, like preemptive rounds are incredibly dangerous. Yes. It encourages you to do more stuff that you shouldn't lose focus to your point earlier, be less capital efficient and then you're unable to scale into the price that is too high and you get people then leave because they know that and then the negative vortex continues.

57:39you have taken a preemptive rounds. Absolutely, a few times. Why am I wrong? I don't think you're wrong. It's really, really hard. And I've gone back and forth ultimately, like my framework and our framework is we're building this to the long term. Who do we want around the table who can help us build this long term? Did you put the cash in the bank for the rainy day? We raised 50, I think we have. Keep me honestly 50, 47 in the bank. We put in our own money to the pre -seed, so we have full skin in the game. We're not going anywhere. We lost it. It comes to me. Yeah, so like, day in and day out, I managed a billion dollar revenue book.

58:18I've seen large businesses operate and have been part of it. So it requires a lot of experience to be able to manage capital well. I think it requires the mental discipline. Honestly, what I see is young founders who raised the 50 and then go, oh, well, we could do this as well. And then we could do this. Fuck it. Why don't we just do that as well? And suddenly they do so much more and they don't have the disciplines say, hey, I'm putting it away. And this will sustain us for eight years if we want it to. And so we can build with a long time in mind. And they just do too much and bring everything forward.

58:45And I make mistakes all the time. I think where was the biggest mistake you've made with rocks between us? We're doing that. And I'm really listening in. I think I spend four years, 16 % of my time on talent. This is the team. I underestimated how important and how powerful it is. We build a founding team of mostly all kind of top AI engineering and that team has built the product, the culture, and hindsight, I would have moved faster to build out that team, and then kind of going back after going to San Francisco, like I need to spend more time. So the biggest mistake is I would have maybe five X'd, the value I would put on just hiring.

59:26Second is very detailed when thinking about AI hiring specifically, the first three months, I wasn't pragmatic enough. Like I was still looking for, Hey, maybe we could do research and let's hire like researchers. No, we're pragmatic. We're building apps here. We're building products. So let's work with the best intelligent providers. Opening eyes of the world, in the tropics of the world, and together to the world. And let's centralize our focus on working with them to build an amazing application. So about month, four, month, five, we learned that hey, we will hire amazing, that kind of apply day engineers who are shipping products.

59:57We're not a research company. Obviously, those will do things. I'd have game designers in your product team. Like if you're thinking about the weekly and daily most importantly, I was just thinking about how do I create like Rotative loops, levelling, this like addictive desire to continue to be in the platform and actually you can see it especially in sales teams Which are highly competitive where you can really create these kind of leadership style boards real composition dynamics Absolutely, you're spot on. I think that is the biggest learning is Getting designers early people deep in thinking about experience getting kind of product engineers who really think about the application, some gamification kind of post, kind of reach a market trade, and really doubling that on that.

1:00:37Get there faster. We're very, very young. We're doing okay, but I would have been more opinionated on day zero. Listen, I want to move into a quick fire around. Let's do a short statement. What sales tactic has not changed over the last five years? Jason gets it. Get on plans. Meet people. Oh, they're with that. What sales tactic has died of death? Like normal. Automated emails. Tell me about a deal that you've closed where you've done something really creative outside the box to get it done. I helped a buyer map out their bots to promotion in a large streaming company that had nothing to do with the technologies that we're providing.

1:01:14It was about how to deeply understand his career objectives to help him be successful. Nothing political, like he was just looking out for help. I probably spent like two months on it. He got promoted and then didn't do the deal. He did the deal. And he's running the whole show and that was a pretty large kind of father company. Oh wow, that's amazing. Yeah. You said about your love for PPLXT early. I love it too. Does it survive in a dominant monopoly world of chat GPT? If they keep the eyeballs and keep shipping, the end features that they are doing, I think there will continue to be a player.

1:01:44Is chat GPT the default? Yes. Do you not think it follows the same market dynamics as I'm an investor in PPLXT by the way, so I'm a big champion. But like I haven't talked about this well. It's really hard to build what they have built in the talent that they have At the very minimum they'll find a massive kind of niche like large Dough grid. Yeah, yeah, yeah, large Dough segment that they will be the best at if not they would be like a strong player in the top three for sure What would be the most significant structural change to sales teams in the nice five to ten years change of their quota?

1:02:22as humans get more productive, as they are able to support more and more customers. The book size that they support fundamentally changes. If that changes, the complete structure of the organization changes. Instead of having large teams, you need fewer teams who hold more book and management layers kind of compress and then you need different kinds of leaders and that completely changes. Like sales and marketing is 40 % of your op -x, right? Like it could potentially go down to 20%. Where does that shift to then? If it goes from 40 % to 15%, that's not going to be a 25 % difference in technology spend.

1:02:56So where else does it get redistributed to? They're just much more margin, like much healthier businesses? Like 50 % of the customer that we work with, this is boring stuff, is private equity owned. Like, me relic is, yeah, 50 % people who come inbound are portfolio wide role models. So there is definitely an element of efficiency. Ken businesses run dramatically more efficient manner when they're not growing at all costs. Yes, as a huge part to it. Where does the capital go? Hopefully some of it goes to increasing the compensation of your supercharged front line sellers. The other I'd hope I am confident I still do think there's so much more to invest in R &D.

1:03:32I think if your technology business wants to be a winner or be the number one, I still feel like R &D is severely under -invested in most scale businesses. I'd hope for or they're kind of frontline, co -ta carrying reps to gain time to make more money. So the company is doing well. And that capital to be reallocated to our end date because we don't do enough of it. How do you maintain morale when goals are missed in the sales work? If you're running kind of the motion where everybody's hitting or hitting and the company's doing great, the morale hits happen when the company collectively isn't doing great because of something macro or the time.

1:04:08If it's the other like where there's winners and losers constantly, there's two different things. Because in general, my view is three things. First is keep ranking. You gotta keep working. Second is trucey. Call your gaps and wins early. Take extreme ownership. Talk about what didn't work. And the third is in terms of morale, I do believe in the power law. There's going to be to 10 to 15 % of the folks who are true believers. We're going to be there for the long term. Just double down on them. If they hit great, if they missed, like, how do we help them win the next time? and then the middle can afford it 50%.

1:04:42Will this sway to the top 10 % or the bottom 10 % and that's what you have to manage, but the only way to manage that is have like doubling down on your kind of outlier. What do you think Salesforce have done really well with Agent Force that you take a new land from? Everything Mark Winiol has ever done, like he's his phenomenal visionary, really told the story well, marketing in sales is obviously like a top notch from what they've done. they have taken legacy enterprise bars, think like CIOs and European, Asian, kind of industrial companies, to really go on this kind of agent, kind of journey where every CIO in the world is buying this year, right?

1:05:22And that is a lot of it is because of him and Agent 4. So painting the vision of what a agentic workforce could look like, he's in a great job and he's that's why he's the coach, right? which other company sales strategy have you been most impressed by recently? I think my time horizon from a recent see perspective, like let's call it like maybe the five years, I would say MongoDB, Dev and that whole crew, I see their leaders in every great company, like XMongo people running gold market in AI companies, the fostering companies is so common. like they just build a winning culture and he's completely transformed into a business and it's a huge success.

1:06:04I learned a lot from him. The other one would be Ramp, like Eric and those folks, they were our second private beta customer. Now we have like the most used products. And there what I've seen is really high horsepower sales folks who've really grown from selling one thing to selling multiple things and now going of market, selling to some of these large, just large customers. And it's all because of just kind of score talent based that they had those two things. Dude, listen, I've so enjoyed this. I love shows like this where I can bluntly just have a very fluid conversation and you do not stick to schedule.

1:06:39You've been fantastic. So thank you so much. No, appreciate you having me in and from from from every founder and every kind of operator. Thank you for doing what you're doing. I want to say huge thank you to Ishan for joining me in the show state that was so much fun to do in person, it really does make such a difference there. I could not be more excited for the times ahead with rocks. But before we leave you today, if you're ready to leave rigid payment terms behind, Camp Chase is here to change the game. Camp Chase brings B2C buying convenience to B2B software and hardware purchases. Camp Chase offers your buyers the flexibility they demand on annual and multi -year contracts.

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1:09:11Get started today at Gong .io and unify your data, workflows and teams with AI to win more. As always, I so appreciate all your support and stay tuned for an incredible episode coming on Monday with Ernie, Found and CEO, Carvana.