20Sales: Why You Need a CRO Pre-Product | Why Remote Sales Teams Do Not Work | How Snowflake Built a Sales Machine with Chad Peets
69m 13s
The transcription features a conversation with a sales expert who shifted from stockbroking to becoming a top software sales recruiter by leveraging innate sales skills and a focused understanding of his audience. He argues that effective sales require knowing what motivates customers—such as career development and product value—beyond just financial gain. A central debate is the timing of hiring a CRO; he strongly advocates for bringing one in pre-product to conduct thousands of customer discovery calls, ensuring the product meets market needs, which founders often lack the time or expertise to do thoroughly. This approach contrasts with the conventional model where founders create initial sales playbooks. The dialogue is punctuated by promotional segments for Payhawk, which streamlines finance operations; Miro, which enhances team collaboration with AI; and Framer, an all-in-one design and publishing platform, each claiming to drive business efficiency and growth.
we bring in a CRO pre-product. You need a salesperson to create the sales playbook. How does a VP of engineering know about creating a sales playbook? Any inside salesperson should recognize that by being in the office, they are going to get better faster. If a sales inside salesperson is not willing to make the sacrifice of a 30-minute commute every day to further his own career, I don't want that person. You have to care and be willing to sacrifice to do exceptional things to be exceptional. And what I find today is people are not willing to do that. But before we dive into the show today, is your finance team a cost center tied up in enforcing policies bogged down by cumbersome processes and drowning in operational busy work? Well, what if you could unlock seamless, strategic finance that actually fuels your business growth? 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Framer already built the fastest way to publish beautiful production ready websites and is now redefining how we design for the web with the recent launch of design pages a free canvas based design tool. Framer is more than a site builder. It's a true all-in-one design platform. From social assets to campaign visuals, to vectors and icons, all the way to a live site. Framer is where ideas go to live, start and finish. No figma imports, no messy HTML. Just design, iterate and ship, all in one place. And it's completely free to start. Ready to design, iterate and publish, all in one tool? Start creating for free at framer.com/design and use the code sales for a free month of framer pro. That's framer.com/design and use the promo code sales. Framer.com/design, use the promo code sales. Rules and restrictions may apply. - You have now arrived at your destination. - Chad, I don't think I've ever been quite so excited about doing a show following a discussion pre-us starting recording. So this is gonna be a lot of fun. Thank you for joining me today. - Yeah, no, I appreciate that. Based on the people that you interviewed in the past, I find that hard to believe, but I'm humbled that you said it, so thank you. - Do you know what also? I spoke to Chris Dagnan and Mike Spicer before this show. And like if you want like hard, heavy weights who are incredible at what they do, saying someone is the best in the world at what they do, I'm like, oh shit. So I'm looking forward to this. So I wanna start off with just a little bit, though, in terms of context. How did you make your way into sales first? And let's start that. - I'll give you the short version, but I saw the movie Wall Street when I was 12 years old and I knew I wanted to be a stockbroker. So I went to USC, I studied finance, I graduated from USC, I went to Merrill Lynch to be a stockbroker. And that was 1997 and 1998. And at that time of that industry was changing. It was becoming a fee-based industry, less about trading stocks and more about just fee-based. And that's not what I wanted to do, one, two. I was turned off a bit because it was such product pushing. By that, I mean, hey, go sell this product to your customers. We're gonna charge one and a half points. This is the shit we want you to sell this week. And I didn't feel at the time like, does it matter if that's the right product for the customer? It was just we're gonna go push that product. The other thing that was clear to me was to be successful in that industry, I was gonna have to accumulate hundreds of millions of dollars in assets. And I was 22 years old, I looked like I was 16. And I would likely have had to call friends and family to raise money. And I was never going to do that. I just simply was not comfortable doing that. So at the time, I had a client that came in, I was doing some financial planning for him. And his wife said to him, you should hire this kid. And I was all arrogant and shit at the time. I was like 22. I think I made a hundred grand in my first year at a school. I thought it was all the money in the world. And I kind of chuckled at this shit. You can't afford me. Just staring at smug and he's like, how much money do you make? It's only like a hundred grand this year. I started laughing at him. He said, you don't even know what real money is. You have no idea. Put me right in my fucking place. He said, look, I run the largest software sales recruiting firm in the country. I think you could do it. You should come talk to me. Oh, okay. So I went and talked to him and decided I'm gonna get into software sales recruiting at 22 years old. Change my entire path. I had a wife at home. I was going from making $100,000 to being a recruiter with no base salary. And it was all going to be on me. And my wife said, you're going to do what? I said, yeah, we're going to give this a shot. And first year there, they were the largest firm in the country. I was the number one guy at the company. First year there. I was the number one guy at the company every year I was there. And then in 2001, the bubble burst. The partners turned on each other. And basically both tried to hire me away from the others. And I said, look, I can't be a business with people that are, if you guys are going to do this to each other, you're going to do it to me. So I started pizza and associates in 2001. I'm fascinated. You move from stock broking. By the way, Blue Horseshoe loves amicot steel. It was one of my favorites. 100%. But you said that. I was like, oh, I like him so much, but it was just so good. But you said that about like, hey, first year I was the number one sales person. Like how? So you move from stock broking. I can sell. Recruiting is selling. And so. OK, so question. Were you just born a good seller? Like, are people born great at sales? 100%. You can't teach. If someone's either someone either can sell or they can't, you can teach someone to be better. But if they don't have the innate ability to sell, some people are petrified of the phone, right? Like, you'll say pick up the phone and they're like, oh, god. I mean, I have to speak to somebody on the other side. I just did not have that fear. I was very comfortable getting somebody on the phone, thinking three steps ahead. I can understand, I think, what your needs are before we start the conversation. And I can think about the objections I think you're going to have before you have them. Use those skills and I just walked my ass. How do you do that? Because most people do like customer discovery where they ask the most inane annoying questions, you know? What are your most prime challenges? And there's a custom you're like, for fuck's sake, this is a crap expert. Focus, right? So focus is number one. So all I did was software sales recruiting. So the only people I was calling were software sales reps. So you learn your audience. So if you're a software sales rep and I study you enough, I know what motivates you. I know why you got into software sales. I know why you're sticking with your job. I know what's going to turn you on about the next job. So when I'm looking at the current company I'm recruiting for, I have to look at the things they have to offer and line those up with what the sales person is looking for. A very few people understand this, right? So you have to know who the person is you're calling. Look at their background. Look at the jobs they've taken to get to where they are and understand, okay, this is what motivated this person. By the way, it's also how you avoid calling 95% of the people that sell software. I don't recruit sales people anymore, but 95% of the people that sell software, I'm never calling. Because I can look at your background and say, okay, I know a lot about you because you made this job at this, you made this change at this point in time. I know what you were looking for. And because you were looking for that, you can't be looking for what I have to offer. I'm not calling. It's very targeted. So like my claim to fame when I was doing sales recruiting was two candidates, one hire every time. And so like when Chris and I, if you're going to go, now we're getting off target a little bit, but Chris and I took a sales organization and grew it faster than any sales organization has ever grown in history. It's no fake. There might have been other scents that have grown faster, but at the time nobody's done that, right? And if you're going to scale like that, you can't have 10 interviews per hire, right? It kills the productivity. So my claim to fame was, look, I'm nailless. I'm going to put two people in front of you. You're going to hire one of them every time. And it's about understanding your audience, and it's about understanding what you have to sell that audience and aligning the two before you even get on the call. Be mentioned like the focus and knowing the customer so intimately well, wonderful. But what do you do in a world which isn't verticalized sales when you have a horizontal customer base, which could be in aerospace or it could be in fintech and banking, how do you do that when you have a horizontal customer base you're selling? - It doesn't matter, like every company I've ever built horizontal to be clear. I've never built a sales organization focused on a particular vertical. Because I don't actually don't think that's a great approach. There's companies that have been successful in doing so, but if you're going to sell a product that only goes to one vertical, you're seriously limiting the size that the company can be, right? Just think about the tam. Like if I'm going to sell into healthcare and that's all I can sell into, that's you better crush healthcare because you have no other alternative. So every company I've ever been a part of building has been horizontal, right? So it's not about that. It's what motivates a sales rep. What motivates a sales rep that I want to recruit? Most sales rep, I want to make money. No shit. Like if I get a guy in the phone, what's your number one motivator? I want to make money. No shit, you got into sales. Is that the only thing that motivates you? Because if that's the only thing that motivates you, we're done here. I have nothing, I have nothing to discuss with you. So can we just say, I know you want to make money. I want to be developed. Oh, now I'm onto something. I want to be the best software sales person that I can be and I want to go work for people that are going to teach me and help me grow my career. That's what I want to hear. I want to sell a product to customers that's world class that's going to add value and change the way those customers conduct their businesses. Okay, now we're onto something. You care about products, you care about development. Development is key because if you don't care about getting better, then you don't care about your career. Chad, what you just said sounds lovely, but sales people who are good are often good at selling themselves. How do you detect the BS in the I want growth, development, empowerment? No, I fucking don't. I just want the money. Super easy. I'm going to pull up your resume. So help me understand why did you go from this company to that company? Why what was the motivating factor there? Why did you make that move? Oh, well, they offered me a bigger base salary. We're done. Why did you go from this company to that company? Well, they raised my quote at my current company and I wasn't real happy. We're done. But if you say, I went from this company, that company because I'm interviewed with that leader and I know every CRO, I know every sales organization and software. So I know if you're full of shit, I know who the good sales leaders are. And if I see you went to a company that I know, AppDynamics, MongoDB, Snowflake, where they have great sales leaders. And you say, oh, I went to work for Chris Degnan because I knew he was going to develop me. I knew I was going to get better. I can validate that based on the career moves in your res. To what extent do you place weight on references? And what I mean by that, a lot culture can be different. It can be not suited someone. Some cultures are suited, some are not. Some leaders are suited, some are not. How do you think about the weight on references? And how to do that well and right? OK, so the higher up you go. So for a CRO, every CRO, every Sutter Hill company, and I've placed them all, has been somebody that I know that comes from my ecosystem. I can ask a blind question. There's going to be a lot of people who listen and go, well, that's not going to encourage a diverse set of candidates. Well, that ecosystem continues to grow, right? And we have a playbook that has expanded and become more and more widely adopted. I'm sure you've heard of Medic or MedPick and all of the things that we use. So that has become more and more widely adopted. But you're right. If you look at my CROs, our CROs across our portfolio, they all come from that ecosystem. The problem is, most of these guys are now reaching the point where they've made so much money where they may not want to go back and do this again. So you have to look for the next generation. This was one of my questions, which was like, it's often said that actually it's so hot being a sales leader. No one in their right mind would do it twice. It's not true. Early stage, 100%. It's the worst job in software. So we do something unique at Sutter Hill and that we bring in a CRO pre-product. Most people don't do that. And I can explain the justification for it. But we bring people in pre-products. So if you look at like a good friend of mine, Keith Butler and Observe, amazing guy, we brought him into Observe before there was a product. He's been there for five years. The company's killing it. He's doing a great job. But he's been there for five years already. And so if you-- I don't want to put Keith, I don't know if I keep. But if you ask somebody that's gone from Ask Chris Degno, you've gone from zero. Chris is the only guy that's ever gone from zero to 3 billion. But if you ask somebody that's done that, hey, would you go back to zero? Absolutely not. Why would you bring in a CRO pre-products? So the way most companies do it is they-- you get an entrepreneur built a product. Goes and raises some money. Builds a go-to-market team goes out and sells the product, right? Agreed, that's not the basic formula. OK, so how do you know when you're building the product, if you've built the product, the market once? How can you know that? You think you know what you don't know. But you don't know. You do custom a discovery before and during product build. Who's doing, hopefully, the founder? Maybe. But what does a founder really know about it? You need a sales expert that can go conduct thousands of phone conversations that is sophisticated enough to get on the phone with the prospect to say, if we build-- and this is evolving, right? We usually go from alpha to beta to GA. And then it just continues, right? So the conversations are constantly changing and evolving. In the early stages, it's just, hey, if we built this, would you get value out of it? Tell me how you get value out of it. What are some of the things you need to see in the product? So that has to take place before you build the product. Otherwise, you could build a product that nobody wants to buy. Just understand. What do you believe that sales leaders or CROs pre-product bring that a founder cannot, the extensive nature of the questions they ask? Most founders, not all, but most founders are product people, engineering people, not sales people. So is a former VP of engineering just to pick somebody? Is that person the best person to make thousands of phone calls? Do they have the time, by the way, to make thousands of phone calls and reach out to these people and do those discovery types of conversations and then capture all that data, summarize it and make sense of it so that you can then give it back to the product and engineer organization. That's not what they should be doing. And by the way, they're not the best people to do it. So we always hear that, actually, you know, you should create the sales playbook as the founder. And then once you have some form of early playbook, you should hide the sales leader. Yeah, I don't agree with that. You think that's BS? I don't want to say it's BS. I think it's backwards. Is it not just so important for them to continue and see be so close to the customer? What I worry, 100%, they should be involved, right? And when we'll have the CRO bring in the founder to some of these conversations. But again, even if the VP of engineering was super qualified to do it, how are they finding the hours? We're talking about thousands of these phone calls. And you have to reach out to the people, coordinate the phone call, get people that are willing to talk to you, right? It's a lot of time and effort just to get the conversation set up. Your founder, it's a full time job. In fact, it's a full time job for probably a couple people. So do you then have to by nature raise large seed rounds? Because if you're going to bring in a CRO and a couple people, this is not a two to $3 million seed round. Yeah, usually you're going to need more than a couple million bucks to do this. You don't need 20, but you probably need 10. Is that a genuinely viable and realistic option, though? Sutter Hill, we're different. We incubate our own stuff. So everything we do, we incubate inside the four walls of Sutter Hill. So I can't talk to whether or not this is the right formula for others. This is the right formula for Sutter Hill. So once you, and by the way, it's one of the reasons I think we're the best in the world at building our own companies. I agree with that completely. I think the data probably shows that. But once you have that CRO that in place, I'm just intrigued because when we chatted before, you said that you're super passionate about building the right type of sales org. And when you said this, I was like, great. But what does the right type of sales org actually mean in reality? How do you think about that? So let's think about the CRO that we're talking about. When you're talking to most CROs that they've done later stage deals, the first thing, one of the things you can ask them is what's your relationship like with the product organization? Who has designed your product roadmap? Where does that come from? More often than not, what you're going to hear is, oh, I talked to the product marketing people. OK, well, who designed the product roadmap? Oh, the product organization does. Yeah, yeah, problems, right? Because product organization is going to go build what they think the customer wants to buy. The person that knows what the customer wants to buy is the person that's talking to the customer. It's the CRO. So you need a CRO that has experience and is sophisticated enough to go work collaboratively with the product organization to design the product roadmap. And say, look, right now, I'm just making this up. We have 50 ICP accounts. I can only sell into 50 accounts, right? Like when you talk to Degnan, right? Like in the very early days of Snowflake, we can only sell into add tech accounts. That's it. They were just selling to add tech. So as you want to expand that ICP, in Snowflake's case, beyond add tech, you have to know, what do I need to expand that ICP? What features? What security things? What does the product need? So I can go from 50 ICP accounts to 500 ICP accounts. And so you have to figure out what those features are. And then you have to come up with a timeline and say, OK, if you deliver these features by this date, then I can expand from 50 to 100 ICP accounts. And if I can expand from 50 to 100 ICP accounts, by the way, I can add salespeople. So Mr. Product Guy, I'm going to go hire salespeople based on your commitment to deliver the things we've agreed to in the timeline in which you agree to deliver it. But understand something, if you fail to deliver, I'm going to have salespeople that can't call on the accounts that they need to call on because we don't have the product to do it. And so you need a CRO that understands all of this. And by the way, this is where CROs just get shacked, because they will get pressure from boards, CEOs to say, we need to grow faster. You need to hire more salespeople. Go hire more salespeople. OK. Well, right now I have a 50 salespeople. You want me to go to 100? Well, in order to go to 100, I either need more use cases inside the existing accounts, or I have to go and be able to sell to other accounts. What are you going to give to me from a product standpoint that's going to enable me to do it? Conversation oftentimes just doesn't happen. I'm just interested. When we think about kind of moving from 50 ICP accounts to 150, to what extent are the product requests of those sales prospects that we want to add to that ICP profile? To what extent is that product requests common? And they all want the same thing. What do you do if it's like everyone kind of wants something different? And it's like, so here's a real common mistake. So you hire 10 reps. So what are-- a rep is going to chase money. So if you don't have ICP accounts, what would I-- what I never want to see is, hey, I just hired 10 reps. I put a rep in New York, a rep in Dallas, and a rep in San Francisco and Los Angeles. And I told them they can have all the accounts in those geographies. You're in deep shit. What's the rep going to do? He's going to go chase big dollars. He or she is going to go pay-- so they're going to go call-- hey, I'm going to go selling to Wells Fargo. I think Wells Fargo wants to spend $5 million dollars with us. Oh, really? OK. That rep is going to spend all his time chasing Wells Fargo. Wells Fargo is going to come back with a list this long of all the shit they need to see in the product. That rep is going to want to go back to the product to organization and say, give me this. Now, what if Wells Fargo is the only person that needs all that stuff you've just taken the company and diverted all resources to go build a list of things for a company that may or may not buy? But even if they buy, you've killed the company, right? Because you've taken all the resources to focus on one account. Even if you get the account, you're in deep shit. So to your point, you have to be able to look at all the data. That's why I said thousands of phone calls and say, I know through capturing all of this data that if we build these five things over the next six months, I know it will allow me to go from 50 to 150 accounts because I have the data. Why is sales not doing product marketing? If you have 1,000 calls with you. I mean, seriously, everywhere it's just paused. Does that mean we're on with this? If you have a thousand, not literally, but you know, hundreds of calls with customers, you see the words, you see how they describe pain, the things that they look for, what excites them, you can create the most compelling copy campaigns billboards you name it because you're the ones that live those customer conversations. Why are you not doing product marketing to you? I mean, because sales people, and by the way, there are some that are just to be clear. So I have had situations where sales doesn't trust product marketing and will generate their own content. So that does happen. But sales people, as good as they are, is capturing and understanding the data that doesn't mean they're necessarily great at creating content. So what you want them to do is capture all of the information, feed it back into product marketing and let product marketing create the messaging. OK, when we think about that right type of sales walk, what are the biggest ways that companies go wrong in creating that sales walk? If the CEO does not support the collaboration between product and sales, you got a problem. Now they operate in silos. And what will happen is the product organization will build what the product organization wants to build. Sales guys are struggling to sell it because it's not what the customers want. Product organization says that the sales organization, you suck. We built the product, you can't sell it. You guys are not good. Sales organization says you built the wrong shit. Now, not only do you have them operating in silos, they don't trust each other. And I've seen this and it does not end well. And it's not that uncomfortable. OK, I'm the CEO and I have this. I have this where they don't trust each other. There is this bad culture between product and sales. Chapel, do I do now help me? You've come in. Lead. Lead. Your job as a CEO is to be a leader. Lead. You have two functions that must collaborate. Get them to collaborate. Get them to understand the need for each other. Sales needs product. Product needs sales. They cannot work independently. And there is a revenue hit. That's why you want to explain the sales organization needs to explain to the product organization. If you don't deliver the things that I need, I have a forecast out there that's based on you delivering that product. If you don't deliver that product, I will miss my forecast. So there is a revenue component tied directly into the product organization. And the product organization needs to understand that. They are, in fact, while not as directly responsible as sales, they're still responsible for revenue. And so as a CEO, you have to understand that and you have to get them to work collaboratively together. The thing I find just so fucked in sales walks today is like measuring and incentives. And you said like, you know, tied to revenue there. But then we have some that are like tied to a load of different metrics, whether it's MQLs, SQLs, you name it. And I'm just going like, what is the right way to think about attribution and success within sales teams today? What behavior do you want to drive? What behavior do you, sales people are great because they're predictable. I can get you to do whatever I want you to do by setting up the complex. So would you have, would you have different attribution than according to different companies that you are with or is it always, we're revenue with sales? You know, it can be. You got to look at the business, right? Like, let's say you look at a business and say, okay, our land motion is really good. We're landing. I'm making these numbers up. We're landing. The average land sale cycle is four months. We're landing it 75K. That's a good land motion. I'm happy with that. Now my expand motion is taking 12 months. And I'm expanding from 75 and I'm getting an expansion of 50. That's not good. The sale cycle for the expand is too long and the dollar assigned to the expand is not high enough. I can start to pull different lovers in the complex. So I can say, hey, Mr. Sales Rep, I'm going to pay you 10% on the land. I'm going to pay you 12% on the expand. And just by doing that, I'm going to get a lot more focus on the expand because I pulled that lover. How big an ACV do you think you have to have to have a proper sales motion to justify it? So my biggest worry today is you see a lot of SaaS companies have 10K ACVs. And actually, Jesus, when you have SDRs, A's, customer success for a 10K ACV that has a variability on expansion, it's not enough. Yeah, that's a problem. So first of all, you have to decide, am I an inside sales organization or an outside sales organization, or both? Hopefully both, right? You really want to get both because if you have both, then you can get the velocity business and you can get the enterprise business. And you want both. So if you look at a 10K ACV, well, that's definitely not a field sales rep. If I'm a 10K ACV that I'm exclusively inside sales, and I better be able to keep the cost of sale low. Otherwise, to your point, I can't justify it. The unit economics don't work. And then you have to decide, where do I draw the line between inside sales and outside sales, right? So let's just say you're happy with a 20K deal in the inside sales. What number are you happy with in the outside sales? And it's sort of a rough benchmark. You want to be able to get three X. So there's productivity numbers, right? Like productivity is how we measure everything. It's sort of a rule of thumb. My reps should be able to generate three times the OTE. So if your OTE is 300, rough numbers, you should be able to get 900K in productivity. - How often do you get that? - Well, you better get it or you're not scaling. If you have a field sales organization, and you have 10 reps and the productivity is 600 grand, you better not be hiring. You need to get that productivity. And until such time is either you get that productivity up or at least can look at the data and see that it's trending in that direction and you trust that data, you can hire ahead of getting the productivity number, but you better trust the data. - How do you think about ramp time? When we think about getting to that three X OTE, a lot of people say, well, it's enterprise sales. It's very long sales cycles. The ramp time's tough. - I mean, look, what I want to see it is six months for an enterprise seller. So there's ramp times for inside, ramp time for outside. Inside, I'd like to see 90 days, outside six months. Reality is it probably transmores towards nine months in enterprise. Then you have to start peeling back the layers of the onion. Why is it, are the sales cycles that long? Maybe the sales cycle is only four months. Okay, then why is the ramp time nine months? Is it an enablement problem? Is it a product problem? Or is it just the nature of the business and there's nothing we can do about it? But ideally, you want it to be at six months. Do you think people hire or founders specifically hire sales enablement early enough? And I'm intrigued. What do you think of the biggest mistakes you see founders make with enablement? - So first of all, it should be the CRO's decision, not the founders. The CRO, if it's 10 reps, you can handle it. Like the CRO can be doing it. The problem is, as you start to scale, it needs to become programmatic. And when it becomes programmatic, your CRO can't do it. He's got other things he needs to be doing. So a 10 reps, do you need an enablement person? Probably not. And each circumstance clearly is unique. But at 30 to 40, yeah, you better start to think about it. And so you want the messaging and the program to be rolled out uniformly. I don't want managers doing their own thing. So the managers have to execute on the enablement, but they have to execute on the enablement plan that the enablement person has created. They cannot go off willy-nilly and do their own enablement. And you will see that from time to time. - You said about kind of incentivizing expansions. It made me think of a conversation I had with Chris before when we spoke about CS, customer success. Often customer success are attributed or given the role of expansions and making sure that customers expand as they would want to. - So hot topic, I mean, this is an ongoing conversation it has been for years. Customer success is hard. I don't know that I can look at any one company and say they've nailed customer success. As Chris I'm sure told you, they don't believe in customer success. They don't have a customer success organization, it's snowflake, or at least they didn't. Maybe they've created one out, but they didn't. The feeling was everybody's in customer success. - Do you agree with that? - Their NDR looks snowflake has a world-class product. In the early days, it was crazy. Like people would buy a 15K land deal and they'd expand to 150 and six months, right? So when you have product like that that just expands on its own, you can get away with less customer success. I've not seen that since snowflake, I haven't. So do I believe in customer success? I do, right? Now, how do you roll that out? That's an open debate. But do I think you should, what I don't agree with is the rep does the land deal walks away and the customer success rep is responsible for expansion. Expansion is sales, right? But the customer success rep, high level needs to make sure, okay. Number one is the product being implemented, okay? Have they got the product in? Number two, are they using the product and are they hitting their utilization rates? Are they exceeding those utilization rates? Are they getting the value as your champion getting the value out of the product that he or she thought they would be getting? Are they gonna continue to be a champion for you internally and go talk to other departments so that they come back and buy your stuff? Customer success needs to be managing all that. The sales person is working, should be working like this with customer success. They should be hand in hand. You don't always see it that way, but that's the way it should be in mind. When you see founders today and when you work with companies today, what are the biggest mistakes you see in terms of that relationship between sales and customer success? You kind of hit on one. One of them is just like, look, let the rep do the land and customer success is responsible at that point. That just also drives really shitty behavior from the rep because the rep is just not focused on the customer journey. The rep is focused on getting a deal done and walking away. You do not want that because then you can get over book deals. So I can go into an account and think, well, let's just say you're on a consumption model. I think that these guys probably need to consume $50,000 in credits over the next 12 months, but I'm paid off of bookings, right? Not consumption, I'm paid off of bookings. So maybe they're only going to consume $50, but I think I can get them to commit to $100. Can't fault the sales guy, he wants to get paid. So he's going to go book $100,000 or a deal. And then a year from now, you're in deep shit because you booked $100,000 if they've consumed $50, and now the accounts at risk, you're going to have churn problems. You're certainly not expanding. And so that behavior has got to be worked out of the rep so that the rep understands, look, you've done the land deal. That's the beginning of the journey for you. The big payoff for you is on the expand deal and the further expansions, right? So first and foremost, you need to get the sales rep thinking about the entire customer journey, not just booking a deal and walking away, which is very different than how software sales has been historically, right? When you were selling license deals, you walked in, did the deal and walked away. It's completely different now. - Completely is different. We mentioned there about kind of Chris Snowflake, then not agreeing with CS. I'm just interested because when I spoke to Chris beforehand, he said that you were essentially core to hiring really the entire sales team for the first five years at Snowflake. I just want to dive into that because you mentioned before about the velocity that you had. What are some of your biggest lessons on what worked first? - So first of all, we talked about being willing to have conflict. There's going to be conflict because each manager is going to have his or her own ideas about the profile and about the process, right? Well, they don't get to have that. If you're going to go hire a world-builder world-class sales machine at scale and quickly, it has to be a well-oiled machine. And what that means is we have a process. We don't deviate from that process. So I'll give you an example. Sales rep, sales rep has called four interviews. So sometimes you'll get, okay, Mr. Hire manager, you interview the rep, binary. You either want to hire him or you don't. Oftentimes, well, I'm not sure. So I'm going to have him go talk to three of my peers. Nope. If you can't make a decision on whether or not you want to hire a rep, let's just say you get two interviews. First one's for selling, second one's for qualifying. If you can't make a decision on whether or not to hire somebody after two hours with him, you're the problem. Not the candidate, it's you. It's binary. Then he goes to the next step of the process. Binary, moving forward or not. Next step, binary, moving forward or not. And you do not deviate from that process, first and foremost. So oftentimes I love a hire manager say, hey, I really, I like this guy. I want to bring in a sales engineer to get his opinion. Nope. Well, he's going to be working with the sales engineer. I don't care. If you're going to be in my interview process, you are either uniquely qualified to qualify or you are uniquely qualified to sell. If you are not one of those two things, you are not getting into the interview process. And so you'll see companies everywhere. They're like, we want the person from HR. I got this engineer. What do those people know about hiring sales people? Are different people not qualified differently to qualify different skills? What's an engineer know about qualifying a sales person? What you're going to go to is culture. Well, we want to see if it's a culture fit. Nope. Because here's the problem you have. So you bring the engineer in. Number one, it slows the process down. Number two, there's risk. I don't know what this engineer is going to say to the sales guy. We're recruiting. He could say something about the product, but he shouldn't say it scares the shit out of the rep. So there's risk there. Three, say the engineer, the rep candidate interviews with four managers, they all want to hire them. The engineer is like, I do not want to hire them. Now what are you going to do? You're fucking hiring them is what you're doing. But you've just pissed your engineer off. Well, I don't think you should hire them. Well, we're going to hire them anyway. Well, I don't agree with them. Now you got friction in the organization. Or are you going to say, OK, well, us four sales leaders like them, but this one engineer knows better than us four sales leaders about hiring a sales person. I don't think so. You mentioned speed that. You agree with high-false, high-false. And how important is speed? 100%. You have to hire fast. If you're going to go scale, you have to hire fast. But the key is understanding the profile, having somebody on the front end, which in my earlier days was me. And this is the profile. I'm not deviating from it. Back to the conflict thing, I said. So let's just say you hire a new VP of the East. And he has his background. And he's got five people he wants to bring with, which is a good thing, because we need to hire. But he has his five people, and they don't meet my profile. If I'm not on the front end, or somebody like me isn't on the front end, to support Chris and be Chris's eyes and ears, then this VP-- because Chris is now running a 400-person organization-- he's not interviewing every candidate. He doesn't have the cycles to. This VP is going to go hire five reps that we know don't match our profile. Now, who knows more about which profile works? A VP that we've just hired that's never sold the product doesn't know anything about it. Or Chris and I, who have built the entire sales organization. Well, I would argue, Chris and I know the profile better than this person. But this person wants to bring in his five buddies that don't match the profile. I'm sorry, Mr. New VP, not happening. And I've had many of these conversations. But Chris-- It's the perfect-- Empowered-- The peripheral vary depending on geography, client type, ACV size. Sure, slightly. But I mean, there's just still the core things you're looking for, right? So think about, what's the job I'm hiring you to do? Well, sell software. OK, it's more nuanced than that. So not to pick on Oracle, but I'm going to pick on Oracle. A reps at Oracle right now. We sell in software, right? We sell in software. That's what he's going to say. And I'm going to say, OK, are you doing pipeline generation? Yeah. I'm selling our new X product into all these Oracle accounts that have never brought X product. I'm hunting for new logos. No, you're not. You're going into install-based accounts, selling a product into them, probably just convincing them to do a rap and roll, saying, hey, if you buy this product, you'll just count the shit out of your existing license to buy this product from me. Now, take that versus you're going to go work for Snowflake, a $10 million ACV company. Nobody gives a shit about a cloud data warehouse. Nobody's ever heard of Snowflake. And I'm going to take that rap and give him 25 accounts and say, go convince those accounts to move all of their data from on-prem to a company called Snowflake they've never heard of. Those are two very different jobs. Should AEs be responsible for demand, Jen? They should get some support. It's a gray area. OK, they should get some support. But if I ever hear that a rep says, why aren't you hitting your number? Why I'm not getting any leads? You ain't going to make it. So yes, they are ultimately responsible for their own lead generation. But they should be something-- How quickly do you know when you've made a missile? I mean, like I had somebody not long ago say, look, we hired a rap, it's been three weeks. And I'm like, OK, look, if you're going to make a decision after three weeks, there needs to be an HR issue, substance abuse issue. The person is not showing up for work. It's got to be super obvious to fire that quickly. If you're starting to see signs, well, hey, look, you committed to the person. It's your hire. It's your job to make them successful. So if you're seeing worrying signs, fix them. So I don't want to give you a timeline, right? But when you get to the point of, OK, it's time to change this person out. It's because you've done everything you know you can do to make the person successful. And they're still not getting them. And you can look at the account list because there are times when you hire good reps into shitty accounts. So you also have to be honest and say, OK, is this just the patch or is this the individual? And a good manager knows this stuff, right? So it's the point in time where you say, I've done everything I can do to make this rep successful. There's no extraneous circumstances which would be causing him or her to fail. It's time to make them move. The other option is you have a rep that's been doing well, and now they're not doing well. Sometimes, especially at startups, it's a grind being a rep at a startup. You may just lose the will to do it, you know? And so at three years, what happens is you start to see behavioral changes. Reps not showing up in every call. I look at the pipeline. His pipeline is light. I'm measuring his number of new business meetings. Those are starting to drop off, right? So I'm looking at the data saying something is happening here. What's happening? And then you got to dig in. It's the biggest reason why a previously well performing rep turns into a non-performing rep. There's a lot of factors, but some of it is just what they get tired. I had this debate with one of our CEOs not long ago. And he said, look, I want my reps. Sales reps should love their jobs. They should enjoy their day jobs. And I said, I don't, that's not possible. They can love working for us, and they should. They should love their CRO. I respect my CRO. My CRO is invested in me. He's developing me. I'm winning, right? Big thing, I'm winning. You're making me successful. So I may not love every aspect of my day job, but I love working for you for all of those reasons. But do I like getting on the phone and making call calls three days a week and doing pipeline generation? No, I do not. So having a rep that loves his day job is very difficult in our environment. Because nobody likes doing pipeline generation. It's not fun. It's a grind. And so what can happen over time is reps wear out. And what you'll see after what can happen is, okay, I've been in the startup for three years, and I'm worn out. And then what do they do? They don't go to another startup. They go to a big company. I'm worn out. I don't want to do this shit anymore. Comes back to reading resumes. Hey, you were at this startup company, and you did really well. And then you went to IBM to use an extreme example. You went to IBM for five years. We're never talking. I'm never recruiting you. Not because you're not a good rep. Because by that move, I know what I need to know. You're done with, you don't want to do the heavy lifting anymore. Totally fine, but you don't fit into one of my companies. Are there any other core elements that you absolutely nailed with Snowflake that enabled the velocity, the scaling of that sales machine that we haven't touched on? You have to get every single person aligned on messaging, okay? Every person has their own different way of recruiting. But the messaging about the company has to be spot on and uniform. So like when I was at Snowflake, they asked me a couple of times to come up there and record videos of my Snowflake pitch specifically around the equity, right? And so Chris and I would set up calls frequently with all of his managers because the data was changing which meant the pitch kept changing. And so my job was to make sure that every leader, everybody in the interview process had the right messaging down. This is how we sell this shit. And you need to be selling it the right way. If you get managers saying different things and selling it differently as the reps are going through the process, what happens? You lose credibility. Hey, this manager said this, this manager said this, what the fuck? Now I just don't believe anything you guys were saying. You see, you got to get that you got to nail the messaging and it's got to be uniform. On the flip side, what did you not do? Well, when you look back now, you're like, okay, we nailed the consistency of messaging. We nailed the process. What do you like with the benefit of hindsight? We would do that differently. There were times when we were scaling faster where we could have probably raised the bar higher. In the early days. It's been in the seat today better than waiting for the perfect candidate tomorrow. That's a balance. So look, there are many hiring managers out there. CROs, in fact, that will say I have a checklist of 10 things. I'm going to look for the candidate that checks all 10. They will go do 100 interviews and in nine months, not fill the position. They'll get desperate and they'll bring in a guy because he has a pulse that checks two out of the 10. I've seen it a lot. And so to answer that question, it's a balancing act. It's a, but when you're hiring at scale, you have to hire. Because if you can't hire next year's forecast, not this year's, but next year's forecast is shot. Now you're going to the board saying, I got to lower the number. I know we raised off of doing 200 next year. I get it. I'm sorry, I can't hit 200 because I'm 50 heads behind because I can't hire lower the forecast, which usually means a CRO is getting shot. It's balanced to answer your question, but not hiring and missing recruiting is not an option. What have been your biggest mistakes in recruiting? I heard you were the best in the world that sales recruiting. That's that's something from Spicer. I work on this today, so I am not afraid of conflict. I don't like it. My wife, I think, thinks I like it, but I don't like it. I'm willing to have it to get to the right outcome. Having said that, I need to work on my diplomacy. As Mike has said to me, look, you're all about saving time and being effective when you deliver messages, which is correct. If I have something to say, I'm going to say it. And I probably could say it in other kinder, softer, gentler ways than the way I say it, which would be more effective in the long term than just saying what I have to say and getting it out there. And so my approach, and I do think I've gotten better at this, but I still need, I still need to work on it. My approach in terms of how I communicate and being more diplomatic, I would have done a better job at that in the past. And hopefully we'll do a better job going forward. Everyone wants to work at a hot company. Snowflakes is a sexy company in many respects. And when it was growing super fast as a startup, it was, how do you detect the company? The people who just want to see it on the rocket ship? Because it's a rocket ship. No, I mean, I'm sure we hired a lot of people like that itself, like, but again, it comes back to when you intervene. What are you looking for? Are you looking to be developed? What is your motivation for wanting to come here? Well, it's the hottest thing out there. OK, I get it, but is that it? Is that all you're looking for? Right, are you looking for career progression? Are you looking for development? Or you just want to be a part of something hot? So no, I don't think it's bad. Look at, look at Databricks, right? Databricks is hiring lots of people. So I might argue too many people. We'll see how that plays out. A lot of people are just going to Databricks as it's a hot company. Or so they think. What makes a great sales rep today? And it's not changed over time. I don't think so. I don't think it's changed. I mean, what has happened has become harder to find. Why does it become harder to find? Because our world has changed. Sometimes I feel like I don't have a place in this, just to be honest. I'm not sure I've fit into the world going forward. But like we talked about earlier, right? If I try not to say controversial things here-- You can take the matter, if that. And what I find today is people are not willing to do them. Hey, what's the culture like? What does that mean to you? Culture to me is I want to go to a place where we're going to win. I want to go to a place where the world class sales organization to say I'm a part of something special. I want to go to a place that develops and making me better. I want to go to a place that believes in meritocracy. That's a great culture to me. You ask other people to define great culture. Well, tell me about how you guys view paternity. How much time do I get off of my wife as kids? Tell me about your benefits. Do you guys-- do I have to be in the office? You know, I like to be home at four o'clock in the afternoon so I can be with my wife and kids. OK, that's the world we live in today. That's not me. And it will never be me. And I will not hire people. Can you be a truly great sales leader and have balance? Yeah, for sure. All of us have balance. Every CRO I know that's world class has wife and kids. But how do you define balance? You don't have balance. I don't have balance. No. But I haven't-- I'm a great father. My wife was to everybody. I'm a great father. My kids love me. I'm there for my kids when they need to be there for my kids. But I-- people sometimes define being a great father, husband, as the quantity of time with your family. I define it as the quality of time with my family. When I'm with my family, I'm with my family. Other people say, well, I need to spend X amount of hours with my family. But they're not really present. They're doing other shit. I prioritize quality over quality. So what you're saying, there are much fewer sales people and talent that are willing to give the intensity, the competitiveness, the unwavering commitment that is required to be excellent. Absolutely. I'm a founder that you're advising. How do I combat that, then, Chad? I hope somebody can solve it and tell me, because I don't know what it is. Recruiting today is harder than it has ever been for the type of rep we are looking for. For somebody that's willing to put the work in, it's looking for the development that we offer. Lot of reps today just don't give a shit. They just don't care, which is a concept I simply do not understand. If I'm going to do something I'm going to go all in and I want to be the best in the world at it, a lot of these people just don't care. So that's a problem. What are you doing to solve it? Nothing. I will not budge on the profile. Right? We will not bud. Even somewhere zero, there are certain aspects of the profile that I will not budge on. And so what happens is it's pointing you budge on. You've got to be willing to put the work in. Would you put your budge on the remote? Depends on the function. Inside sales. Absolutely not. Somebody said to me the other day, they were building an inside sales team. And he said, look, we require inside sales people to be in the office. My competitors don't. So they're beating me when it comes to recruiting. Because I'm calling reps saying, you have to be in the office five days a week. They're recruiting reps saying, no, no, no, no, you can work from home. So I'm losing. I said, the fuck you are. You're winning and you don't even know it. He said, well, what do you mean? I said, well, let me explain to you. I'm going after salespeople to care about their career. OK? I want the best of the best that are willing to invest in themselves. They're going to develop faster. They're going to be better at what they are doing faster. If a sales inside salesperson is not willing to make the sacrifice of a 30 minute commute every day to further his own career, I don't want that person. So you go ahead and hire. You build your company with those people. I'm going to build my company with the people that are willing to make the sacrifices to do something great. And I tell you what, I'm going to kick your ass. I love you, Chad. No, one, I totally agree with you. But I also think there's like real information advantages that come from physical co-location, which is like, oh, you hear product talk about how the new feature of that building. You hear customer support talk about problems. You hear those customer conversations. It all feeds into a much more to your point earlier, cross-functional organization, which works together better. 100%. So there's certain functions like an outside salesperson. You can't make them be in the office. I don't want them in the office. I want them in front of customers. It's outbound dead. I mean, look, I don't think it's dead, but people are having to find new ways to do it. What I'm being told-- and again, I don't do it-- but the feedback I get is emails linked in. Simply doesn't work. It just-- there's too much of it. So what I'm hearing is it's gotten back to old school, which was getting cell phone numbers and making phone calls, which I don't think is terribly effective either. But it's, as I be, it's being shared from an SDR standpoint that is more effective than just messages. So I think content is the most important thing in the world today when it comes to salesperson, because I think if you cool me and say, hey, I'm from Snowflake, and I go, oh, I actually loved your guide that you released last month. What can I help with? Suddenly, that's a much better style. It is, but what if you're a startup? I work for XYZ company. I'm trying to sell this product. You never heard from me. Snowflake was your hook there, because everybody's heard of Snowflake. So OK. But what if you're a company, nobody's ever heard of it? You've got to do really effective content marketing. You do. I mean, I'm not saying it doesn't work. And by the way, this is where I think AI comes in and helps a lot. It's the way I do the way I do the way a verticalization helps a lot. If you are selling two restaurants, I can way more-- Totally agree. Because it's customized content, right? And that's why it's so interesting. You said earlier, like the horizontal approach, I love the verticalized approach. I look at notion, and I look at air table, and I look at all these companies. Actually, question for you. All of them are trying to scale into enterprise with a PLG motion. I think that's really fucking hard. Getting the world's biggest enterprises to adopt notion. Are you kidding me? It's a totally different motion. And the problem-- I mean, look, there's a lot of time you can spend on this. But PLG, I don't know enough about their businesses. But let's just say you've got a low-level developer. It's bot your product, and he's using your product because it's PLG, right? So he's put his credit card, and he's using your product. And now I want to go sell to the CTO. And I have an enterprise rep totally different motion. So it's a completely separate sales organization. So now I've got an enterprise seller in there. I want to go sell to the CTO. CTO probably does not give a shit that he's got a bunch of engineers using the product. It's a completely different value proposition. And so a lot of people think, if I nail PLG, then I'll nail enterprise. You can nail PLG in enterprise. I just would argue that nailing one does not necessarily make you more likely to nail the other. So if you can do both, do both. But in my opinion, you've got to start with direct sales, and then let the product get to where the product needs to get through and then go to PLG. You think it's easier to start with enterprise? I do. Now, I'm not an expert on this, but I do. PLG is largely just-- enterprise is driven by a go-to-market function. It's an entire function. PLG, yes, has that. But it's largely driven by the product. One of the biggest mistakes I find founders make that I invest in is they say, too early, we're going to expand into enterprise. They say, oh, we're getting pulled in. We're getting pulled in. And I'm like, you're 3 million in ARR. You don't need to be pulled anyway. How do you think about timing of the expansion? So when we build companies, let's go back to self-like. We start in mid-market. Because why? Because I want to take a very small, a set of accounts, typically smaller accounts, because their demands are less. And I want to nail it. I want to build the product to make them happy, right? So like we have another one of my company, SIGMA. People say, well, it's a mid-market company. It's not a mid-market company. It's an enterprise. We started in mid-market by design. Because you want to have some set of customers that you can make very happy. And it's always going to be smaller accounts first. As you're making those customers happy, you're learning, as we talked about earlier, about what it takes to make the enterprise happy. And you're building that product out. So eventually, yes, you will move upstream to the enterprise. But oftentimes, you're 0.10 million. I don't-- you can't pick a metric and say, that's the metric. It's a feel for what you're getting from the customers to understand when the product is ready. But yeah, you see, customers-- excuse me-- companies go to the enterprise way too fast, right? And any company whizzes the only one I've seen do it successfully where they started in the enterprise. But typically, you want to start mid-market, which buys you time to build the product and feature set to go to the enterprise it's some later day. Do you agree with the common statement your smallest customers will most often be your most painful? Your wrong customers can be your most painful, right? Like, it's not the size of the customer. It's the wrong customer. If you're trying to keep a customer happy, that ultimately isn't a good fit. And I don't like churn any more than anybody. But sometimes, you have to look at certain customers and say, it's better that we churn this, churn the account. We can't keep them happy. We're committing too many resources to keep this small one happy. Gross revenue retention or net revenue retention. I always have this conversation with Dave Hello. Two different metrics, the measure, two different things. Which one do you think founders should focus on more? I've run to a spot and are-- Look, I don't think one is more important than the other that you just have to look they measure different things. Gross retention tells me if people like my product, right? Like, I understand if my gross retention is 90%, I probably have a pretty good product, right? If my gross retention slips down to 70%, I have a product probably. Net dollar retention is about expanding. So you can have high gross retention and a low NDR that doesn't necessarily mean you have a product problem. It means you might have a go-to-market problem. You might have a customer success problem. There could be product attributes that contribute to it. And the GRR measures to me is really about product. NDR is, yes, it's product-related, but it also ties in a bunch of other things. So I wouldn't say one is more important than the other. But I will say this, if you have a low gross retention number, by the way, by definition, you're going to have a low net dollar retention number. But if you have a low gross retention problem, you got problems. You can have a high gross retention and a low NDR. And yes, you need to address it, but it doesn't mean you're in deep shit. But if your GRR starts to slip, you got problems. If your GRR starts to slip, and the company starts to not do as well, it's tough to have that morale that's still in good shape. It's a problem. How do you advise sales leaders on how to keep a sales team together when you're in a really shit patch? And there's not momentum, and it's just shit. It's tough, and the people that are going to see it first are the sales engineers. Sales engineers are going to-- And so what will happen is your SCs will start to depart before your reps. And when your SCs start to depart, reps know that the SCs know more than the reps know about the product. So your SCs start to depart, and the reps will start to follow. And so again, it comes back to we talk about operating in silos. So if I'm a sales rep, and I'm like, hey, we're losing accounts because we said we were good, why do you lose accounts? So why do you have-- why do you have churn? Lots of different reasons, but you can have churn because we said we were going to deliver something, and we didn't deliver it. They bought the product. We committed. We didn't live up to that commitment. One, two, product just isn't working. That's another problem. Three, they're not getting the value out of the product they thought they would. And so as a sales rep, you're taking this information. You're feeding it back to the product organization. If the product organization is going like this, your reps ain't going to stay. If the product organization is saying, we got it. We hear you. Here's our plan to solve for that. We will deliver on this plan over this time frame. And then they actually deliver on it, then you can hold the sales organization together. But if they don't, you got a problem. Because the sales person feels like, I can't win. I go into these accounts. I can't win. I'm doing everything I'm supposed to do. You've sent me into a gun fight with a switchblade. I'm doing my job. Help me arm me. And you're not arming me. You're telling me that I should win with my switchblade. Or more to the point, you're telling me I have a gun. And it looks like a switchblade. I'm like, no, I have a switchblade. I think the challenge I often see is I think CEO sat forecast or sat revenue goals, which are well above the expectations or beliefs of the CRO. And it sets everywhere for failure. I mean, here's the most common thing, right? CEO says, OK, I got to go raise around. I want to raise around this valuation. To get to this valuation, forecast needs to look like this next year. Guess what, Mr. CRO? Here's your forecast for next year. The right CRO. Now, our companies are different. This cannot happen in our company. We will not allow for this, right? So the Sutter Hill company, CEO says, here's a forecast for next year. We say, great. Chad Pete's John McMahon, your CRO are on agreement with this, right? Because if they're not, that's not the forecast. So there is alignment. We do not do this. This is a mistake. We will not allow for it, Sutter Hill. Outside of Sutter Hill, CEO says, I got to go do this. And there are companies you and I both know where this has happened. The CEO, the CRO, either has to say, hold on. I am not committing to that. Like he says, or productivity number, right? Like the CEO will say, productivity this year is at $750. Next year, it's going to $9.50. Oh, is it? How is our productivity per rep going to magically go up by 200 grand? Oh, it just is. You can't have them, right? But those are the different things they do to justify the higher forecast to get the round of funding. It's tail wagging dog. The business should dictate the forecast. Not some arbitrary number that we need to raise around the funding. But that is what happens. And so back to the point, CEO says to CRO, here's your forecast for next year. CEO is going to, CRO has got a decision. You either stand up for it right there or you accept the fact you're getting fired in nine months because you know you're not hitting that number and I promise you they're going to blame you. And this happens a lot. How many do you think stand up at the time and say, no, I can't hit that number? Not enough. Because they want to keep their job. And it's like, look, I'll do everything I can this that and the other. But like they know the same thing with hiring, like I got a hundred reps. They just told me I got to go to 200 reps. I can look at the data and say, we're not ready to go to 200 reps. CEO says in order to get to the forecast, we got to go to 200 reps. What is the biggest way that people fuck up onboarding? You know, I had that, I had a STRs from replaying on the show. She's had 350 STRs in like a year or two or four years. It's a lot. Yeah. I mean, no, I'm credit time saying that with compliments, but it's like, I'm thinking about the onboarding. It's got to be programmatic and you got it, you got to dedicate resources to it. I mean, too, too often, as we talked about early stage, fine, what's your, what's your it scale like that, you have to have a programmatic approach, right? And you have to invest in it. There need to be classes. You need to bring them on site. It needs to be an ongoing process that take months that you are and don't get greedy and try to put the rep into a position where you're expecting revenue before you should expect here. She to be enabled to commit the time and resources and understand it's going to take this amount of time, this amount of resources to get our reps enabled. Do not take shortcuts. People take shortcuts in discounting. Is that okay? How do you feel about discounting? You know, again, it varies on the stage of the company, right? Early stage company. Look, we do, you'll do negative margin deals, right? Like, we're going to do this deal, but we're going to lose money on the deal. But we need the referenceable account and we'll make up for it later. 20% do. No, in that state. 20% to referenceable accounts actually make a difference. Early they make a big difference. Because again, you have an ICP where all of the accounts have very similar criteria. So if, to your point, if you're verticalized, which we all kind of are in the early stages, right? Because we have such a narrow ICP and you get some well-known account and all these accounts talk to each other and they respect each other and you get a referenceable account. That's meaningful at that stage, right? Later on, it's less meaningful unless it's a really big account and then it's more meaningful. Chad, I could talk to you all day. I kind of need that from the first moment when you said about Wall Street. But I want to start, I'm sorry, I want to finish on a quick fire round. So I say a short statement, you give me your immediate thoughts. Does that sound okay? So what if you change your mind on most in the last 12 months? That the world is changing and I need to accept the fact that it's changing and people may not come along with the way that I see with what I see. Can you not just keep going the way you are, just with the same network? I'm going to try and if I get to a point where it's like the world doesn't want to operate the way I want to operate, I will likely retire. You don't want to change. I'm not going to change. No, I mean, I will change certain things, I need to be more diplomatic. The thing that keeps me coming to work every day is learning. That's what turns me on. I want to get better every day. I want to work with people I can learn from every day. So that in it, that's kind of changing, but there are certain things I will not change. What's your biggest advice to someone starting a sales rep role to more? Take the time to invest in your career. Reach out to people to learn, learn as fast as you can and work as hard as you can. And you will become better than everybody else around you. On the flip side in terms of hierarchy, you've got a sales leader and I call you up the night before I'm starting my first like role as a sales leader. What would you advise me knowing all that you do now? Understand our business. So when you get here, you need to understand before it because now you have people reporting to you that are looking to you to add value. Very difficult for you to add value and tell you understand our business. So get in front of customers, talk to salespeople, do whatever you have to do to learn our business as fast as you possibly can so that you can start adding value to the reps on your team as quickly as possible. What's the biggest piece of BS advice that you often hear about sales? I get tired of hearing people say, look, sales people are coin operated and they are to a certain extent. They're predictable, which I like, but I get tired of hearing all sales people give a shit about it. It's making money. They're mercenaries this side and the other, I think that's bullshit. I think that's bullshit. I think the right sales people do care about the company. They care about the careers. Yes, they want to make money, right? But I think the right sales person is more than about just making money. What makes Mike Spicer so special, what he's done is unparalleled. I mean, fine. I get spend three hours on that. Look, I love Mike because Mike is always going to make the right decision. Always. Yes, he's a good human being. Yes, he's loyal and all that stuff. Mike is never going to take the easy path ever. He's always going to make the right decision, which may involve pain and doing difficult things. It doesn't matter. He's always going to do it. The only person I've ever seen or heard about that is a good stock picker. He understands markets. He can see things around corners that most good stock pickers can, but he's also an operator. I've never seen anybody else that has both of those attributes. Tell me, what's the biggest mistake you see found as making scaling to 10 million in an error? In that first journey, what is this biggest mistake that you see found as that you were with Mike? They hired a wrong zero. Pure and simple. You hired a wrong zero because you have no idea what you're looking for. There's companies which you would know that I've consulted and I've spoken to their CEOs and I'm like, what are you looking for in sales? They have no idea. In order to make the right hire, you first have to know what you're looking for and most of them don't even know what they're looking for. The problem is they don't have people that they can reach out to to tell them what to look for. I don't fault them for not knowing. The challenge is they don't have investors and board members that can tell them, hey, this is what you need to go hired to and hiring the wrong zero, kill you because then he or she's going to go build out the sales organization that's going to be the wrong sales organization. It's going to take you two years to figure it out and then you are starting over. Final one for you, Chad. What question are you not normally asked that you think you should be asked more? What's your biggest weakness? I don't know that I've ever gotten. You've never gotten that. I get like, because my story is pretty unique, right? There's very few people. In fact, I think I'm the only person that's ever gone from being a recruiter and to being a managing director at a venture firm and then starting his own venture rates. Not that it makes me better than anybody, it's just a unique path, right? When I went to Sutter Hill and I was sitting at our partner meetings, there was one guy that didn't go to Harvard. That's me. There was one guy without an MBA. That's me. I'm the dipshit that went to USC. So I get questions about the path, but I don't get that question enough, right? What's your greatest weakness? What is your greatest weakness? It's being patient. Mike has helped me a lot, right? When I see what I deem to be an emergency, and there's people that have called me to the floor and this rightfully so, when I see something to be as an emergency, I'm fucking all over. It's not, hey, let's take our time. Nope. This shit needs to be fixed right here, right now. And the reality is, when you have 100 different fires, you have to learn to prioritize things. And every problem doesn't need to be dealt with today. Some of them can be put off for a period of time. And I have had to learn that lesson. And honestly, Mike has helped me learn that one. And so, because when you're constantly saying, fire, fire, fire, fire, and they are fires, people are like, oh my god, this motherfucker is calling me again, dude. We just put a fire out. Can we hold on? So that's probably my biggest weakness, it's just learning some patience. Chad, listen, I absolutely love this. I knew when Dagnan and Spice said what they did, it would be a special one. But thank you so much for doing this and I've so enjoyed it. Me too. Thank you so much. It was great to meet you. But before we leave you today, is your finance team a coscentre tied up in enforcing policies bogged down by cumbersome processes and drowning in operational busy work? New AI agents for each finance role handle the busy work, acting with the same governance as your finance team, like having a small team of expert assistants that work 24/7 but also providing an exceptional user experience to your employees. 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Podcast Summary
Key Points:
The speaker transitioned from stockbroking to software sales recruiting, emphasizing innate sales ability and deep understanding of customer motivation as keys to success.
He advocates for hiring a Chief Revenue Officer (CRO) before a product is fully built to conduct extensive market discovery and ensure product-market fit, contrary to the common founder-led approach.
The discussion highlights the importance of sales reps being driven by career development and product value, not just money, and the need for sacrifice and commitment to excel.
Advertisements for Payhawk (finance platform), Miro (collaboration workspace), and Framer (design tool) are interspersed, promoting their efficiency and transformative business benefits.
Summary:
The transcription features a conversation with a sales expert who shifted from stockbroking to becoming a top software sales recruiter by leveraging innate sales skills and a focused understanding of his audience. He argues that effective sales require knowing what motivates customers—such as career development and product value—beyond just financial gain. A central debate is the timing of hiring a CRO; he strongly advocates for bringing one in pre-product to conduct thousands of customer discovery calls, ensuring the product meets market needs, which founders often lack the time or expertise to do thoroughly.
This approach contrasts with the conventional model where founders create initial sales playbooks. The dialogue is punctuated by promotional segments for Payhawk, which streamlines finance operations; Miro, which enhances team collaboration with AI; and Framer, an all-in-one design and publishing platform, each claiming to drive business efficiency and growth.
FAQs
A CRO pre-product can conduct extensive customer discovery to validate market demand and shape product development, ensuring you build something customers actually want to buy.
Look for candidates who value development and career growth, not just money. They should be willing to sacrifice and show commitment to improving their skills.
Review their career moves on their resume. Genuine interest in growth is shown by moves to companies with strong sales leaders and development opportunities, not just higher pay.
Payhawk transforms finance teams from operational to strategic by automating busy work with AI agents, providing a seamless user experience and supporting global business growth.
Miro's AI tools help structure thinking, synthesize information, and create visual roadmaps, enabling teams to move from ideas to execution faster and more efficiently.
Framer unifies design, CMS, and publishing in one tool, allowing teams to design, iterate, and ship websites quickly without switching between different platforms.
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