Chad Peets: Why Most Sales Reps Underperform & Remote Reps Ignore Development | E1193

We bring in a CRO pre-product. You need a salesperson to create the sales playbook. How? What 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.

Ready to go. [Music]

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 going to be a lot of fun. Thank you for joining me today.

Yeah, no, I appreciate that. Based on the people that uh you've 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 Stanagan and Mike Spicer before this show, and like, if you want like hard heavyweights who are incredible at what they do, saying someone is the best in the world at what they do, I'm like, oh, he's gonna be he's gonna be good, so I'm looking forward to this. So I want to 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 there.

Oh, I'll give you the short version, but um, I saw the movie Wall Street when I was 12 years old, and I knew I wanted to be a stockbroker. Um, I knew that, so I went to USC, I studied Finance, I graduated from USC, I went to Merrill Lynch to be a stockbroker, and that was uh 1997 and 1998. And at that time, that industry was changing; it was becoming a fee-based industry, less about trading stocks and more about just fee-based, and 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 going to charge one and a half points; this is the 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 going to go push that product. The other thing that was clear to me was to be successful in that industry, I was going to 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 to do that. Um, I I just simply was not comfortable doing that. So at the time, I had a client that came in, and I was doing some financial planning for him, and his wife said to him, you should hire this kid, and uh, and I was all arrogant, and at the time I was like 22; I was making, I think I made 100 grand my first year out of school; I thought it was all the money in the world, and I and I kind of chuckled; I said, man, you can't afford me, and uh, just arrogant and smug, and and he's like, how much money you make? I make 100 grand this year. He started laughing at me; he said, said you don't even know what real money is; you have no idea, and just put me right in my place, and he said, look, I run the largest software sales recruiting firm in the country; I think you could do it; um, you should come talk to me.

Wow. Okay, so I went and talked to him and decided I'm going to get into software sales recruiting at uh 22 years old, changed my entire path. I had a wife at home; I was going from making $100,000 to being a recruiter with uh no base salary, um, and it was all going to be on me, and I my wife said, you're going to do what? I said, yeah, we're g we're going to give this a shot, and uh, first year there, they 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, um, and basically both tried to hire me away from the others, and I said, hey, look, I I can't be in 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 Piz Associates 2001. That's when I I had that experience. I'm fascinated you move from stock broking, by the way; Blue Horseshoe loves Anacoal Steel. It was when when you said that I was like, oh, I like him so much, but what just so good. Um, but you said there about like, hey, first year I was the number one sales there person, like how so? You move from stock broking to it's a sales job, right? Like I I can I can sell; recruiting is selling, and and so but but okay, a question: Were you just born a good seller? Like, are people born great at sales?

100%. You can't teach someone's; either someone either can sell or they can't. I can I can; 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, you mean I have to speak to somebody on the other side, right? I just did not have that fear, right? I was very comfortable getting somebody on the phone and you know thinking three steps ahead, right? And that's sales, right? Like I I I can I can understand I think what your needs are before we start the conversation, and and I can think about the objections I think you're going to have before you have them, right? And so I just use those skills, and I just worked my ass off.

Can I ask how do you do that? Because most people do like customer discovery where they are some most innan annoying questions. You know what are your most prying challenges? And as a customer, you're like, for sake, this is a c, 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 salesperson is looking for, right? 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 salesp 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 you. It's very targeted. So like my 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 but Chris and I took a sales organization and grew it faster than any sales organization has ever grown in history; it's Snowflake. There might have been others since 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 it kills the productivity. So my claim to fame was, look, I'll nail this; 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.

My hands getting quite full quite quickly; uh, you can't write on paper because it makes noise for the microphones. My first question to you: I want to unpack the Chris and the Snowflake skating, but you 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?

It doesn't matter; like every every every company I've ever built, horizontal. To be clear, we I've never built a sales organization focused on a particular vertical, right? And because I I don't actually don't think that's a great approach. There's companies that have that have that have been successful in doing so, but it's if you're going to sell a product that only goes to one vertical, you're 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 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 look what what motivates a sales rep? What motivates a sales rep that I want to recruit? Most sales rep I want to make money. No, like if I get a guy in the phone, what's your number one motivator? I want to make money. No, 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 on to something, right? I want to be the best software salesperson 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 on to something. You care about product; you care about development, right? Development is key because if you don't care about getting getting better, then you don't care about your career.

Chad, what you just said sounds lovely, but salespeople who are good are often good at selling themselves. How do you detect the BS in the I want growth, development, empowerment?

No, I don't; I just want super easy. I'm gonna pull up your resume, so help me understand why did you go from this company to that company? Why? What 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 quota at my current company, and I wasn't real happy. We're done. But if you say I went from this company to that company because I'm interviewed with that leader and I know I know every CRO; I know every sales organization and software, right? So I know if you're full of; 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 Dean because I knew he was going to develop me; I knew knew I was going to get better; I can validate that based on the career moves in your resume.

To what extent do you place weight on references? And what I mean by that, okay, but but culture can be different; it can be uh not suited to someone; some cultures are suited; some are not; some leaders are suited; some are not. How do you think about the weighted on references and how to do that? Well, and right, the higher up you go, so for a CRO, every CRO at every Sutter Hill company, right, and I've placed them all, has been somebody that I know that comes from my ecosystem. Can ask a blunt 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 MedPic 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 C our CROs across our portfolio, they all come from that ecosystem. Now the good news is there continues to be more and more people on their way up in that ecosystem, so you have to look for the Next Generation, the generation from BladeLogic, which includes some home like, right? I mean, Dan Fuer from Datadog, Adam Aons from Octa, right? I mean, look at all of the different AppDynamics, Dolly Ric, who's a close personal friend of mine; um, you can look at, you know, Chris Dagnan that came out of that like, but the problem is most of these guys are now reaching a 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, you know, it's often said that actually it's so hard being a sales leader; no one in their right mind would do it twice. Is that 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, right? Most people don't do that, and I can explain the justification for, but we bring people in pre-product. So if you look at like a good friend of mine, Keith Butler at Observe, amazing guy, we brought him into Observe before there was a product; he's been there for five years; um, company's killing it; he's doing a great job, but he's been there for five years already. And so if if you I don't want to put Keith identify Keith, but if you ask somebody that's gone from ask Chris Dean, you gone from zero; Chris is the only guy's ever gone from zero to three billion, but if you ask somebody that's done that, hey, would you go back to zero? Absolutely not. I'm sorry.

Why would you bring in a CRO pre-product?

So the way most companies do it is they you get an entrepreneur; entrepreneur builds a product; goes and raises some money; builds a go-to-market team; goes out and sells the product, right?

Agreed. That's the basic form. Yeah. Okay. 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, but you don't know. You you do a discovery before and during product; who's doing that? 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 built, and this is evolving, right, as you 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 before you build a product; otherwise, you could build a product that nobody wants to buy.

Just so I 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 for product. Most Founders, not all, but most Founders are product people, engineering people, MH not sales. So is is is a is a former VP of engineering 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 Engineering organization? Founders, 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 ear playbook, you should hire the sales leader.

Yeah, I don't agree with that.

You think that's BS?

I I don't want to say it's BS; I think it's backwards. You need a salesperson to create the sales playbook. How? What does a VP of engineering know about creating a sales playbook? Is it not just so important for them to continuously be so close to the customer? What they should be involved, right? Uh, they should, and and when we'll have the CRO bring in the founder to some of these conversations, but 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 it's 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 of 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 of people, this is not a $2 to $3 million seed round.

Yeah, usually you're going to need more than a couple million bucks to do this. Yeah, you don't need 20, but you probably need 10.

Is that is that a genuinely viable and realistic option though? I mean, I mean, look, Sutter Hill, we're different; we incubate our own stuff, right? So everything we do, we incubate inside the four walls of Sutter Hill, so I I can't talk to whether or not this is the right formula for others; this is the right formula for Sutter Hill, and by the way, it's one of the reasons I think we're the best in the world at building our own companies. But once you have that CRO then 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. 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, yeah. So when you're talking to most CROs that are 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 talk to the product marketing people. Okay, well, who designs the product roadmap? Oh, the product organization does. You got you got problems, right? Because the 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, we I'm just making this up, we have 50 ICP accounts; I can only sell into 50 accounts, right? Like if when you talk to Degan, right, like in in the very early days of Snowflake, we could only sell into adtech accounts; that's it; they were just selling to adtech. So as you want to expand that ICP in Snowflake's case beyond adtech, 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 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 the timeline and say, okay, 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 jacked because they will get pressure from boards, CEOs to say, we need to grow faster; you need to hire more sales; go hire more sales. Okay, well, right now, I have up 50 sales; 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 other accounts. What are you going to give to me from a product standpoint that's going to enable me to do it? That conversation often times just doesn't happen.

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 what do you do if it's like everyone kind of wants something different and it's like so so here's a real common mistake: So you hire 10 reps; so what are what rep is going to chase money? So if you don't have ICP accounts, what what 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 because what's the rep gonna do? He's gonna go chase big dollars; he or she is gonna go pay, so they're gonna go call, hey, I'm gonna go sell into Wells Fargo; I think Wells Fargo is wants to spend $5 million with us. Oh, really? Okay, that rep's going to spend all his time chasing Wells Fargo; Wells Fargo's going to come back with a list this long of all the they need to see in the product; that rep is going to want to go back to the product organization and say, give me this now. What if Wells Fargo is the only person that needs all of that stuff? You've just taken the company and diverted all resources to go build a l 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. 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 a thousand—I'm being serious, pause—does that mean run with this? If you have a thousand, like 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 too? I mean, because salespeople, and by the way, there are some that are right, just to be clear, so I have had situations where sales doesn't trust product marketing and and

Will generate their own content, so that does happen. But salespeople, as good as they are at capturing and understanding data, 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.

When we think about that right type of sales org, what are the biggest ways that companies go wrong in creating that sales org? So now we've talked about the CRO, right? So we've talked about what the CRO must be good at: finding product-market fit. But you got to go deeper than that into some of the things we just discussed: working with product, capturing data, sharing all that, working collaboratively, etc., etc. And by the way, you have to have a CEO that supports that, right? Because your CEO might—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. The product organization says to the sales organization, "You suck; we built the product, you can't sell it; you guys are not good." The sales organization says, "You built the wrong…" Now, not only do you have them operating in silos, they don't trust each other. I've seen this, and it does not end well, and it's not that uncommon.

What do you—okay, 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. Chad, what do I do now? Help me. Come in, 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, right? Sales needs product; product needs sales. They cannot work independently, and there is a revenue hit. Like, and 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 to 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 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? It's—what behavior do salespeople—are great because they're predictable. I can get you to do whatever I want you to do by setting up the comp plan accordingly. Would you have different attri—then according to what different companies that you work with, or is it always—we're revenue? It—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 sales cycle is four months; we're landing at 75—75k." Okay, 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 sales cycle for the expand is too long, and the dollar assigned to the expand is not high enough. I can start to pull different levers in the comp plan, so I can say, "Hey, Mr. sales rep, I'm gonna pay you 10% on the land; I'm gonna pay you 12% on the expand." And just by doing that, I'm gonna get a lot more focused on the expand because I pulled that lever.

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, customer success for a 10k ACV that has a variability on expansion, it's not enough. Yeah, that's a problem. So, 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—and you want both. So if you look at a 10k ACV, well, that's definitely not a field sales rep, right? If—if I'm a 10k ACV, that I'm—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 so—and then you have to decide, okay, where do I draw the line between inside sales and outside sales? 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—and is sort of a rough benchmark, you want to be able to get 3x. So there's productivity numbers, right? Like, productivity is how we measure everything, but as sort of a rule of thumb, my reps should be able to generate three times their 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. So 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—you need to get that productivity. And until such time as 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 3x OTE? A lot of people say, "Well, it's enterprise sales; like, it's—it's very long sales cycles; the ramp time's tough." How do you think about that? I mean, look, where I want to see it—is six months for—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 trends more towards nine months—in enterprise. Then you have to start peeling back the layers of the onion: Why is it take—are the sales cycles that long? Maybe the sales cycle is only four months. Okay, then why is the ramp time nine months, right? Is it an enablement problem? Is it a product problem, right? 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 Founder's. The CRO—if it's 10 reps, you can handle it, right? Like, the CRO can be doing it. The problem is, as you start to scale, it needs to become programmatic, right? And it—when it becomes programmatic, your CRO can't do it; he's got other things he needs to be doing. So at 10 reps, do you need an enablement person? Probably not. And each—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—the program to be rolled out uniformly, right? 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. Customer success is hard. I—I don't know that I can look at any one company and say they've nailed customer success. You know, as Chris, I'm sure told you, they don't believe in customer success; they don't have a customer success organization at Snowflake, or at least they didn't; maybe they created one—but they didn't—the feeling was everybody's in customer success. You agree with that? Look, Snowflake has a world-class product. I mean, it was in the early days; it was crazy, like people would buy a 15k land deal, and they'd expand to 150 in 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—I haven't. So do I believe in customer success? I do, right now. How do you roll that out? That—that's—that's an open debate, right? But—but do I think you should—the what I don't agree with is the rep does the land deal, walks away, and the—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—have they got the product in? Number two, are they using the product, and are they—are they hitting their utilization rates? Are they exceeding those utilization rates? Are they getting the value? Is your champion getting the value out of the product that he or she thought they would be getting? Are they going to 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 salesperson 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 my opinion.

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? Well, you—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 overbooked deals. I can go into an account and think, well, 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 a $100,000 deal, and then a year from now you're in deep because you booked 100,000 if they've consumed 50, and now the account's at risk; you're going to have churn problems; you're certainly not expanding, right? 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—that's the beginning of the journey for you; the big payout 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—they're 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—first of all, we talked about being—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—build a 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, call it, four interviews, okay? So sometime you'll get—"Okay, Mr. hiring manager, you interview the rep; binary; you either want to hire him or you don't." Often times—"Well, I'm not sure, so I'm gonna 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. So 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 you'll have a hiring 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 salespeople?" Salespeople are different people; not qualified differently; to qualify, different skills. No. What's an engineer know about qualifying a salesperson? Which 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: okay, so you bring the engineer in; number one, it slows the process down, okay? 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 that he shouldn't say and scares the shit out of the rep, okay? There—so there's risk there. Three—say the engineer—the—the—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 hiring them is what you're doing, but you've just pissed your engineer off. "Well, I don't think you should hire him." "Well, we're going to hire him anyway." "Well, I don't agree with that." Now you got friction in the organization. Or are you going to say, "Okay, well, us four sales leaders like them, but this one engineer knows better than us four sales leaders about hiring a salesperson?" I don't think so.

You mentioned speed; do you agree with—hire fast, fire fast? And how important—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—"This is the profile; I'm not deviating from it." Back to the conflict thing I said, so let's just say you hire—hire a new VP of the East, right? And he has his background—or she—and he's got five people he wants to bring with him, which is a good thing because we need to hire, but he has these five people, and they don't meet my profile. If I'm not on the front end, where 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 a 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, and they're not popular, but Chris empowered me.

Does the profile 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: sell software. Okay, it's more nuanced than that, okay? So not to pick on Oracle, but I'm going to pick on Oracle—or reps at Oracle, right? Now he's selling software, right? He's selling software; that's what he's going to say, and I'm going to say, "Okay, are you doing pipeline generation?" "Yeah, I'm selling our new X product into all these Oracle accounts that have never bought X product; I'm hunting for new logos." No, you're not; you're going into installed-base accounts selling a product into them, probably just convincing them to do a wrap and roll, saying, "Hey, if you buy this product, I'll discount 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—" that's 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 rep 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 SDRs be responsible for demand gen? They should get some support. Now, if—if—if I ever—but it's—it's a gray area, okay? They should get some support, but if I ever hear that a rep says, "Well, why aren't you hitting your number? Well, I'm not getting any leads," you ain't gonna make it. So yes, they are ultimately responsible for their own lead generation, but they should be supplemented.

How quickly do you know when you've made a mis-hire? I mean, like, I had somebody not long ago say, "Look, we hired a rep; it's been three weeks," and I'm like, "Okay, 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, right? It's got to be super obvious to hire 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." I don't want to give you a—a timeline, right? But when you get to the point of, "Okay, it's time to change this personality," it's because you've done everything you know you can do to make the person successful, and they're still not getting there, 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, "Okay, 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 the move." The other option is you have a rep that's been doing well, and now they're not doing well, right? Sometimes—get—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: rep's not showing up on every call; I'm looking 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?"

What is 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. Look, it is—I had this—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 cold calls three days a week and doing pipeline generation? No, I do not. Having a rep that loves his day job is—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 a 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 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; 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. Chris and I would set up calls frequently with all of his managers because the—the—the data was changing, which meant the pitch kept changing, right? 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, 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—now I just don't believe anything you guys are saying." So 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? Like, 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—would do differently? There were times when we were scaling faster where I could have—where we could have probably raised the bar higher. Um, in the early days, is filling a seat today better than waiting for the perfect candidate tomorrow? That's a balance. So look, like I know 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 N months not filled a 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, can't hire. Lower the forecast, which usually means a C is getting shot. It's balanced to answer your question, but, but not hiring and missing recruiting is, is not an option.

What have been your biggest mistakes in recruiting? I heard you were the best in the world at sales recruiting. That's, that's something from Spy. 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, um, to get to the right outcome. Having said that, uh, I need to work on my diplomacy, as Mike has said to me, "Look, you're, you're all about saving time and being effective when you deliver messaging," which is correct. If I have something to say, I'm going to say it. 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 in getting it out there. Um, 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, um, my approach in terms of how I communicate and being more diplomatic. I would have done a better job at that in, in, in the past, and hopefully we'll do a better job going forward.

Everyone wants to work at a hot company, Snowflake, a sexy company, uh, 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 seed on the rocket ship because it's a rocket ship?" And is that bad? No. Um, I'm sure we hired a lot of people like that at Snowflake, but again it comes back to when you're interviewing, what are you looking for, right? Like, are you looking to be developed, right? What, what is your motivation for wanting to come here? Well, it's the hottest thing out there. Okay, 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. Um, look at, look at Databricks, right? Like Databricks is hiring lots of people, some might argue too many people. Um, I, I, I, we'll see how that plays out, but um, a lot of people are just going to Databricks because it's a hot company, or so they think.

What makes great sales reps today, and has it changed over time? I don't think so. I don't think it's changed. I mean, it's been, it's what's, what has happened is it's become harder to find. Um, why is it become harder to find? Because our world has changed. Um, you know, sometimes I, I, I feel like I don't have a place in, in this, just to be honest. I'm not sure I fit into the world going forward, but like, why, why? Well, like, like we talked about earlier, right? Like you have to care and be willing to sacrifice to do exceptional things, to be exceptional. And, and what I find today is people are not willing to do that. They, 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 with a world-class sales organization to say I'm a part of something special. I want to go to a place that develops and makes 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, um, how you guys view paternity? How much time do I get off? My wife has kids. Tell me about your benefits. Do you guys do—Do I have to be in the office? Um, you know, I like to be home at 4 o'clock in the, in the afternoon so I can be with my wife and kids. Okay, that's F—okay, that's the world we live in today. That's not me, and it will never be me, and I will not hire people like that.

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, has wife and kids. But how do you define balance? Well, Chad, you have balance. I don't have balance. No fair, but I have—I'm a great father, like my wife would say, everybody, I'm a great father. My kids love me. I'm there for my kids when they need me to be there for my kids, but I—people sometimes define being a great father, a husband, as the, the, 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—I prioritize quality over quantity. So is what you're saying there are much fewer salespeople and talent that are willing to give the intensity, the competitiveness, the unwavering commitment that is required to be excellent? Absolutely. How do we—I'm a Founder that you're advising—how do I combat that? I, I, I hope somebody can solve it and tell me, because I, I don't know what it is. Recruiting today is harder, and again I don't do it, but I manage my guys to do it, so I get all the feedback back. Recruiting today is harder than it has ever been for the type of rep that we are looking for, for somebody that's willing to put the work in, that's looking for the development that we offer. A lot of reps today just don't give a—they just don't care, which is a concept I simply do not understand. If I'm going to do something, I'm gonna 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? How you change it? Ju—nothing. I will not budge on the profile, right? Like we will not budge, like even some of our C—like I will—there are certain aspects of the profile that I will not budge on. And so what happens is, what, what, what aspects won't you budge on? You, you've got to be willing to put the work in, right? Like, would, would you budge on remote? No, but depends on the function. So 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." Okay, so they're beating me when it to recruiting because I'm calling reps saying you have to be in the office 5 days a week. They're recruiting reps saying, "No, no, no, you can work from home," so I'm losing. I said, "The—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 who care about their career. Okay? I want the best of the best that are willing to invest in themselves. Any inside salesperson should recognize that by being in the office they are going to get better faster, 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 gonna kick your ass." That's how I—I love you, Chad. No, I—one, I totally agree with you, but I also think there's like real information advantages that come from physical collocation, which is like, oh, you hear product talk about how the new feature that they're 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, um, functions like a fe—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.

Is outbound dead? I don't think it's dead, but people are having to find new ways to do it. Like what, what I'm being told, and again I don't do it, but, but the feedback I get is emails, LinkedIn simply doesn't work. It just, it—there's too much of it. So what I'm hearing is it's all—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, right? 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 the sales process, because I think if you call me and say, "Hey, I'm, I'm here from Snowflake," and I go, "Oh, I actually loved your guide that you released last month. What, what can I help with?" Yeah, suddenly that's a much better sale. It is, but like, what if you're a startup? Well, I work for XYZ company. I'm trying to sell this product. You've never heard from me. Snowflake was your hook there because everybody's heard of Snowflake. So okay, but what if you're a company nobody's ever heard of? You 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, and, and helps a lot, right? I, I do think it's also where verticalization helps a lot. If you are selling to restaurants only, I can more target those customized content, right? Yeah, and that's why it's so interesting you said early like you like the horizontal approach. I love the vertical approach. I look at Notion and I look at Airtable 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 hard. Getting the world's biggest Enterprises to adopt Notion? Are you kidding me? Totally different motion. It's a totally different motion. And, and the problem—I mean, look, there's a lot of time you can spend on this, but PLG, you've got—I don't know enough about their businesses, but let's just say you've got a, a low-level developer that's bought your product and he's using your product because it's PLG, right? So he's put his credit card in, he's using your product, and now I want to go sell to the CTO, right? And I, and I have an Enterprise rep—totally different motion, right? So it's a completely separate sales organization, right? So now I've got an Enterprise seller in there. I want to go sell to the CTO. CTO probably does not give a that he's got a bunch of engineers using the product. It's a completely different value proposition. A lot of people think if I nail PLG then I'll nail Enterprise. You can nail PLG and 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 you got to, in my opin—I, you got to start with direct sales and then let the product get to where the product needs to get to, 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—D—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 anywhere." How do you think about timing of the expansion? So when we build companies, we all—let's go back to Snowflake—we start in mid-market, right? Because why? Because I want to take a very small 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, um, another one of my companies, 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 your point—10 million—I don't—you know, you can't pick a metric and say that's the metric. It's a feel for what you're getting from the customer—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—Whizz is the only one I've seen do it successfully, um, where they started in the Enterprise, right? But typically you want to start mid-market, which buys you time to build the product and feature set to go to the Enterprise at some later date.

Do you agree with the common statement that your smallest customers will most often be your most painful? The wrong customers can be your most painful, right? Like it's not the size of the customer, it's the wrong customer. If we, if, if you're trying to keep a customer happy that ultimately isn't a good fit, and I don't like churning 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 the small one happy." Gross revenue retention or net revenue retention? I always have this conversation—two different metrics that measure two different things. Which one do you think Founders should focus on more? Everyone talks about NRR. I don't think one is, is more important than the other. They 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, I, I, I probably have a pretty good product, right? If my gross retention slips down to 70%, I have a product problem. 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, right? But, and the, 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, right? 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. 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, it's a problem—bad.

How do you advise sales leaders on how to keep a sales team together when you're in a really patchy and there's not momentum and it's just—I mean, it's tough. And, and the people that are going to see it first are the sales engineers. Yeah, sales engineers are gonna—and so what'll happen is your SEs will start to depart before your reps, and when your SEs start to depart, the reps know that the SEs know more than the reps know about the product, right? So you'll see SEs 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 our—we, we said we were good"—why do you lose accounts, right? 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, right? 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 gonna 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 timeframe," and then they actually deliver on it, then, then you can hold the sales organization together. But if they don't, you got a problem, because the salesperson 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 gunfight with a switchblade. I, 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, 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 a challenge I often see is I think CEOs set for costs or set revenue goals which are well above the expectations or beliefs of a CRO, and it sets everyone up for failure. I mean, here's the most common thing, right? CEO says, "Okay, 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—this, we will not allow for this, right? So Sutter Hill company CEO says, "Here's a forecast for next year." We say, "Great. Chad, Pets, John McMahon, your CRO are agree—are in 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 at 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 C—the CEO will say, "Productivity this year was at 750. Next year it's going to 950." 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 that, 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 a round of funding, but that is what happens. And so back to the point—CEO says to CRO, "Here's your forecast for next year." CEO's C's got a decision. You either stand up for—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 gonna blame you. And this happens a lot. How many CROs stand up at the time and say, "No, I can't hit—not enough"? 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 100 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 up onboarding? You know, I had the head of SDRs from Rippling on the show. She's hired 350 SDRs in like a year or two—month or two years. A lot. Yeah, I mean—know, I'm credit to her. I'm saying that with compliments, but it's like—I'm thinking about the onboarding. It's got to be programmatic, and you got to, you got to dedicate resources to it, right? I mean, too, too often, as we talked about, early stage fine, but once you, once you're at 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 takes months that you are—don't get greedy and try to put the rep into a position where you're expecting revenue before you should expect he or she to be enabled. 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, it 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. To what extent do referenceable accounts actually make a difference? Like early—they make a big difference because again you have an ICP where all of the accounts have very similar criteria. So if, 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. Uh, I, I kind of knew that from, uh, the first moment when you said about Wall Street, uh, but I, I want to start—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? Sure. So what have you changed 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, with, with what I think. Can you not just keep going the way you are, just with the same network? I'm going to try, and then if, and, 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 gonna change. No, I mean, I, I, I have—I have—I will change certain things. I need to be more diplomatic. I, I, I'm, I'm good with—look, the thing that keeps me coming to work every day is learning, right? That's, 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 ended up—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 tomorrow? 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 got a sales leader—Harry and I call you up the night before I'm starting my first like role as a sales leader. What, what would you advise me, knowing all that you do now? Understand our business. So when you get here, you need to understand, because now you have people reporting to you that are looking to you to add value. Very difficult for you to add value until 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, salespeople are coin-operated," and I know I mean, and they are to a certain extent; they're predictable, which I like, right? But I—and I get tired of hearing—all salespeople give a about it: it's making money; they're mercenaries, this, that, and the other. I think that's—I think that's—I think the right salespeople do care about the company; they care about their careers. Yes, they want to make money, right? But I think the right salesperson is more than just about making money.

What makes Mike Spicer so special? What he's done is unparalleled. Ah, I mean, I could spend three hours on that. Um, 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; doesn't matter, he's always going to do it. He's also 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, right? That—that most good stock pickers can. But he's also an operator. I've never seen anybody else that has both of those attributes. I love that. Uh, and so many things.

Tell me what's the biggest mistake you see founders making in scaling to 10 million in ARR in that first journey? What is the biggest mistake that you see founders that you work with make? Pure and simple: you hire the wrong CRO 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?" and they have no idea. And in order to make the right hire, you first have to know what you're looking for, and—and most of them don't even know what they're looking for. And 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 hire." And hiring the wrong CRO will 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, and 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?" You've never gotten that? I mean, it's—it's rare people ask me. I—I get like—because my story is pretty unique, right? Like, there's very few people—in fact, I think I'm the only person—that's ever gone from being a recruiter into being a managing director at a venture firm and then starting his own venture. It's not that it makes me better than anybody; it's just a unique path, right? Like, 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 one that went to USC. Um, so I get questions about the path, but I don't get that question enough, right? Like, "What's your greatest weakness?" What is my greatest weakness? It's being patient. Um, you know, Mike has helped me a lot, right? Like, when I see what I deem to be an emergency, and there's people that have called me to the floor on this rightfully so—when I see something to be as an emergency, I'm all over it. It's not, "Hey, let's take our time." Nope, this needs to be fixed right here, right now. And the reality is when you have a hundred 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 lesson. And so—because when you're constantly saying, "Fire, fire, fire, fire," and they are fires, but people are like, "Oh my God, this is calling me again, dude. We just put a fire out; can we hold on?" So that's—that's probably my biggest weakness is just learning some patience.

Chad, listen, I absolutely love this. I knew when Dgan and Spicer said what they did, it would be a special one. 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.