20Sales: How to Scale Into Enterprise Effectively and the Biggest Mistakes Made When Making the Move From PLG to Enterprise, Why Discovery Today is F***** & The Biggest Lessons on How to Do Sales Team Compensation with Sean Murray, CRO @ Greenhouse

24:36What does that mean? Like how do you actually do that? Does that mean sales team spend time in the CS and CS and sales? I just unpacked that for me and if I'm a founder listening, what should I do? No, it's a great equation to go and solve for. What I'm finding now is that in customer success, you have fewer touch points with your customer and the product must sing for you at some point, of course. But when you're having those customer conversations, can you also weave in the commercial component of upsell and or crosssell? Because in customer success, you're building trust, you're building that relationship.

25:09And in some models of one of which I'm part of and I've been part of, is you have this like awkward high tension moment where a salesperson comes on and it's like, but wait, I got more things for you. But to have that process a bit more centralized is probably the best part. So if I'm a founder right now, You must find people that care greatly. I just saw post by Jason Limpkin and was spot on like your first few CS hires, someone that cares greatly about your product, they're passionate, they're smart, and everything else will sort itself out. But if I'm a founder right now, I would think about combining those roles a bit within CS and account management, but separate that from your new logo hunters.

25:44Make sure that's separated. Okay, so how do you manage the challenging element of the handoff? Hey, Sean, I've sold you, and now you've just, you've learned to love me. meet my colleague Sarah and you're like, whoa, what? How do you handle that? We handle it. How I handle the past is three technology. That handoff should be flawless. So to the founders that are listening, ensure that you should have a hunter organization that chases new logos. I firmly believe it. By the way, Harry, I was able to, one of the highlights of my sales career is I was able to launch the sale of the Challenger Sale.

26:16Have you heard of the Challenger Sale? Right. Oh, Harry, this is a must read for you. Brent Adamson, MetDix, and they're the authors and the researchers behind a lot of the content. But the argument is, and I firmly believe this to this day, you have an organization that secures new logos so long as you have the runway and the tam to support it, and then you have a customer -facing organization. You separate those two. But to answer your question, the technology... Well, that's too good. So wait, you have someone to secure new logos. What does that mean? Like, they go out and they pull together a list of names that could be good targets and just help me understand how that works.

26:50Okay, you have the new logo organization and their only purpose in life is to go get more new customers. So when they get an order for signed, you pass it off to a customer facing team, whether that be called the carom management, customer success, customer support, where do you want to call them? But these are two distinct different teams. Harry, when you have those roles combined, the research is profound. When you combine those roles, it doesn't work very well. So long as you have the tam, the total adjustable market, and you have the green field available where you can go and secure new logos, you've got that runway, those roles should be separated.

27:27Okay, so they're separated. And then we have the handoff where you bring in technology. How does technology help a handoff? Like conversational intelligence? Help me understand how you know, Gong will help our sales and sales teams make a seamless transition. So a big plug for garlic, but the AI that they are building within the conversation intelligence is remarkable. If I'm a customer success person and I'm inheriting a new customer, I can go into calling and just look for quick highlights, quick moments that were important during the sales process on how I'm going to absorb and learn about that customer.

28:04It's brilliant. And so that's how that transition now happens flawlessly. So you would then expect your CS person to come into the cool learn and then me as a CS hop on that handoff cool and say Sean you're the customer in this case. How are your daughters doing? I know that you're going to Taylor Swift and you go oh wow like they've got that relationship base sell already Is that what you want in the enterprise the short answer is yes the last three companies? I've helped build I pursue every segment from SMB startups all the way up to the 20 ,000 employee mega companies. And in the enterprise segment, that level of personalization makes a difference and very important.

28:45So to answer your question, yes, we expect our teams. Maybe not that I'm going to go to a Taylor Swift concert in London with my daughter. Maybe not that far. But certainly what my top three problems are that I must solve in this current year, that level of detail, yes. Now at scale, maybe in the SMB where it's a bit more automated, not as much personalization is required. Okay, so then we have that and you're like, yeah, like the CS person, that's good, that's good. And now I'm going, hmm, as the CS person, we can upsell him. How do I bring in the sales person back into the process when I've now built quite a good relationship with CS?

29:23Yes, you have account managers or salespeople that are also talking to your customers, Along with these customer success relationship builders that are typically measured on NPS, my argument is to combine those rules. Leverage technology, leverage the data on when you know customers should be up for expansion, should be up for cross -selling. Your data should tell you that whether you're using GainSight or GONG, whatever technology you're using, you should be able to see that and allow the frictionless sales environment to happen within the customer organization. So CS is sales? Yes. Yes. Okay, if CS is sales, is there not a misalignment?

30:02Hey me out here. You're one of my customers. You know what? You may not quite be ready for our full enterprise AI product yet, but I think you could be soon. And so why don't I sell it to you now because it's nearly the end of the quarter and I really want that bonus. So you know what, Sean, you need it now. But really Harry, we're all in sales. Come on, we're all in sales and we're serving our customer. We are in the good news the customers expect it right they expect it they expect to be sold to do you think in CS They don't feel like it's a safe space why you do just want them to be made as successful as possible Maybe I'm ignorant and naive.

30:41No, you're not ignorant because my CS organization today They are not in sales. They are not I want to make an argument that we should be today They are not in sales many customer success organizations do not have a quota, right? they sit in cost of revenue or cogs and they do not have a quota and they focus on adoption using the product. That's a classic mark. If they're not but you would want them to be, why are they not? That's the question. Can you not stomp your feet? Well, I am being in my hand against the desk. I gotta be better at my persuasion. But it really also, Harry, it depends also on the product because if the product is easier to adopt, you probably need less customer success.

31:21So the innovation of the product makes the difference. And if you have a heavy people or a human -oriented customer success organization could be a red flag for the buyer. No, I get that. You've said about the range of customers you sell too, and you have sold too over your career. I'm investing many companies in the hoodie growl. It's like, well, we're going to scale into enterprise. And then hundreds of thousands of dollars of ACVs will just magically open up. It doesn't happen like that. And there's this real naivety. What do you think customers or founders get wrong about moving into enterprise?

31:54A lot. Okay, there is a lot to get wrong. The three biggest hurdles in taking that holy grail of moving up into the enterprises, massive ECBs, the sexy LTV to CAC, those sexy logos that you need to talk about. But the hardest problems, first, the credibility. No one knows who you are, especially in the enterprise. IT will destroy you. The second is do you have a real product market fit for those big companies? Because those big companies, they all believe that they're special snowflakes. And so they need things that are just different because you've built an SMB or a mid -market platform that's there to scale.

32:31And third, it's somewhat related to both, but you're financial. And you're financials because as you move up market, they just don't trust you. Very similar to credibility, but they just don't trust that you'll be around. They don't trust that you can survive. As a startup for that long. So I think those are the three that I've experienced to move in. I would ask, okay So IT will kill you. Why? Why will IT kill me? What do we get wrong here? Because as you move up market the IT organization gets more senior and more senior and more authority and more authority The higher you go up and the worst thing that can happen to an enterprise is a data breach or security flaw and many of startups They don't have the proof points that they meet all the compliance requirements at the enterprise will demand of them So to me that's when IT really becomes difficult So as you prepare to move up market make sure that you can defend those arguments before we even try moving up market That's one two will you do customization for me to land my contract?

33:32How do you advise founders on the willingness to customize versus not in order to secure a contract? I love this Harry. So this is the most friction a founder will experience in their life Not not not marriage marriage is easy compared to this friction But this is going to be the real friction is when they are moving up that market and how they're going to differentiate Those two on the customization of sales that because the sales organizations are gonna say hey look We've got to go create 15 different bells and 20 different whistles to make this company work for us And I refer to that as sales debt and so the lesson learned is how do you balance sales debt?

34:14Because every once in a while you're gonna want to take down Adobe as a customer So you can say you've got Adobe as a customer or the snowflake so those sexy logos like sales force whatever But you must balance that sales debt and just know when to walk away from deals because the biggest pain point you move into the enterprises, they want you all to be special, and they want customization and it's gnarly. So as one example Harry at Greenhouse where I'm building now, I really cap it at 10 ,000 employees that I try not to pursue much more above that. And it's mostly because it just gets so difficult above that threshold.

34:49And I don't think the big money really isn't with those companies anyways. They actually, there aren't many companies that have over 10 ,000 employees, but when you get to that level, it gets gnarly. Can I ask you, have you made any mistakes in terms of taking on sales debt too much with a specific customer? Yes. It's easy to you. Yes, many, many, many mistakes. And it's less about over -promising, is being upfront about what we can and can't do or what we can try to do, but the biggest mistake is the time I can't get back. So I went to go after one of those sexy logos. I went back to my product and my engineers were like, look, this is gonna be easy, you gotta trust me.

35:26I've never been an engineer before, but this sounds really easy. And I had my product team, my engineering team, invest a year of their time trying to make it work. And it didn't. And so I can't get that time back in with founders. That time is too precious. And so those are the big mistakes. It's not about being false or lying to your customer, but it's the time that you can't get back. Yeah, I mean, that's a very accommodating product team to be fair to actually engage for that long and to let you roll with it. Yeah, no, I'm totally short. Do you mention the sexy logos? Do they really make a difference?

35:56Like when companies come and say, hey, we've got Slack and Dropbox and you name it, do they make a difference or not? Like cleansing. It's a good question. The short answer is it does make a difference. Now, every salesperson in the world pitches and they over pitch those enterprise logos, but the first problem that I mentioned when moving up market is you lack credibility. And the reason why those logos do matter is I need to show you, So Harry, you're my enterprise customer and you're looking at me like you can't do half the shit that you're talking about But what I need to be able to say is like Harry look I'm gonna set you up with the folks at Slack DocuSign and Snowflake and they're gonna tell you a story of how they use my product.

36:36I need that you need that That's very impressive and different though There's a difference between hey look at these sexy logos now by and hey Why didn't you speak to existing customers and they'll be references for us? Do you see what I mean? Yes? Yes, but they're two in the same, right? Which is, the hurdle you're jumping over is the credibility hurt. Do you worry about asking existing customers to sell for you? Do you worry that it's too much to ask that they don't have time? It depends. Okay, Harry, we're role -playing again. Harry, you as my enterprise customer, I'm not going to ask you for your time to help me go sell to other big companies.

37:12But if you do, maybe I'll give you a little bit of a discount and you'll all do something for you. So I do ask in advance, so when I'm moving up market, I make these concessions as part of my negotiation when I'm closing a deal. Okay, so you'll say, hey, if you can help on up to three different potential customers, we can have a wiggle room of 10 % on a renewal. Correct, right? So as I'm moving up markets over the founders that are listening, that have aspirations to go be bold and move up to the enterprise, do it, but think very carefully. And when you're negotiating these terms with your first 25 state enterprise customers, given gets, you're going to need their help to get this going.

37:51So give them the concessions that they need. Make it worth their while and get it in writing so that you can use it. Okay, another area where they're like, not only, yes, everyone wants customization, especially now everyone wants a discount. And some are like, you know what, we don't discount. We know the value of our product and others are like, of course we discount. What's the right approach to discounting for founders listening, thinking about that scale in to enterprise? Discounting is okay. It's fine. In different environments, it's important that you adjust what you need to. We all believe that our products are the best, especially those founders that are listening I know.

38:28But there are moments that when everyone on the block is charging $80 for a beautiful stake and then the market goes south and then the rest of the street is selling those stakes for $20. You can't keep charging $80 for your stake. You can, but you're going to lose. The worst deal is the one that takes too long. Just move on. Go get the next deal. So I have been a big advocate of flexibility, maybe a discount and refaming it a little bit. It's flexibility in negotiating terms. Not necessarily just discounting a drop of your price, but go get something different. So as an example, if my price is 100K, I will do this deal for 60 and then Harry, What I expect from you is a story about how you love my product.

39:08Harry, I want you on the stage of my annual conference Raving about my product and I want two social posts from you Raving about my product and then we'll do the deal for 60 so it's not a discount. It's a trade I like that you said that I loved it You said there about kind of the time is the biggest killer and if it takes too long move on Do you think you know up front if a deal will take a long time and what are signals that a the potential prospect is going to be a slow mover. Yes, there are many indicators and having a data driven process teaches you about what those clues are. Okay, what are they?

39:45There's probably a list of about 40. The level of consensus that's required. The level of approvals that are required. Okay, so let's just take those, sorry, I like to go. Are people honest? Everyone likes to feel important. When you say, hey, you know, You a decision maker for buying a green house? Of course I am. Yeah, yeah, yeah, yeah, it's me. You're speaking to the right path. How do you know? That's a great call out in you are right. That happens nine times out of 10 and frankly, they are not the person that can sign the order form. So you are right. The question to ask maybe differently is who should I engage early?

40:20Because Harry will play again, okay? Harry, buyers like you, I have 7 ,000 customers and buyers that look and feel just like you. What happens at the end of this process is the CFO will get involved, the head of procurement will get involved, IT will get involved. Harry, I don't think your company's going to be any different. So, in order to be a good steward of your time, let's get them involved now. Because then I can set you up for success. Harry, you want this product, I know you do. But in order for you to be successful, let's get these players involved. Do you know what damage there, you go?

40:49I'm sitting here thinking, you don't believe that I'm the buyer. No, no, I don't. I have this credibility on my shoulder, Harry, because what I said to you, Harry, companies that look and feel just like you. Some of your competitors, companies that are in your ecosystem, this is what happens at the end. My hypothesis is this is what's going to happen to us at the end. These people are going to want to get involved. This competitive selling work, does saying, I'm taking the most competitive industry CRM's, you know, Monday .com and pipe drive, does saying, hey, Monday .com, we're actually working with pipe drive and they're seeing incredible success.

41:23You don't want to be left behind. Does competitive selling work in that respect? I value the question. The short answer, yes. What I will say about with the competition and selling against their competition is when I'm directly the seller is to not be little or throw mud at my competitors. It rarely works. If you roll around on the mud with pigs, you just get dirty. And so I teach my sales organizations as best I can to not speak ill of the competitors. I totally agree. I think it's the fastest way to lose credibility. So there's need to chat shit about someone. I think you see it often with venture investors too, and it's just like, you're not a good way to do it.

42:01Okay, we missed one crucial thing, which is like for me, I think a lot of companies actually try and move into enterprise way too soon. A million an hour, SMB market's a lot bigger than that, okay? So if we wanna start there, let's start there, proper. When's the right time to move into enterprise? You know, you've done three now. When are you like, okay, this is ready to ramp? Yes, I like this question. The first answer would be let the data teach you on when you're able to do it. So if you have inbound, if you have clues from companies as you start to move up ever so slightly, if you get those clues from either, again, the inbound or how your customer is using your products, let that data teach you if you can start creeping up market.

42:41And then the third would be to run a phase one, try it, try. If you want to go into the enterprise, yes, it's a full company effort. And that's what a lot of founders get wrong. What founders think is that it's a sales and marketing good and market thing. It takes a whole company to rally around it. It's an entire company motion looming into the enterprise. It is ambitious but tried. Is there a way to try it without huge resources? Is there a way to put your foot in the water of the enterprise with a couple of customers see if it's what you need? Or is it a full -on budget reallocation? The hard truth is it's a full -on budget allocation.

43:17It's a full -on effort. However, you can test to see if your product will work with a few test cases, with some few customers. So for example, to the founders out there, try and engage in enterprise and maybe do it on the house. Engage a few customers and give them your product for a year and let them use it for a year. Find out where the mistakes are. Find out what goes wrong. Learn what's wrong with your product before you really go big. So there's probably a little bit of bold hairy, but the truth is, you need some capital to go into the enterprise. And you won't get that immediate love. It takes time.

43:51It doesn't have the same return and speed as a SMB or a mid -market will have. That's the truth. I always say enterprises like content. It's way harder than people think and it takes way longer. We did 300 shows before we got to a thousand plays per show. 300. You said they're about kind of the speed and like obviously small ACV small companies, you know kind of quicker. How do you know when a sales rep's not working out? It's a bit easier in sales to know when it's working or when it's not working. And... But do you think it's an enterprise because it takes so long? I do, I do. And the reason why is if you structure a data driven sales process, when you can see, when deals fall off from let's say stage two to stage three.

44:33Or in stage two, if that sales rep wasn't clicking off the right criteria to graduate from stage two into stage three, then you know that you've got a talent issue pretty quickly. What do you do then? What do you do with those reps? Yeah, do you say hey like it's not working and just cut it like how often A wraps repairable versus just let him go. It's a great question. The right answer is you move on and you bring a new talent That's the right answer. Do you think you're good at hiring sales reps? Yes, I'm the best. You know why? Why? Because I've got that software I don't worry about hiring because I've got great software.

45:07Okay. Well help me understand that I'm a founder I'm hiring my sales team. How do I hire sales reps or sales teams with software? Okay, there's a lot to unpack here, but I've been leveraging software for many, many years in my hiring effort. And when I'm learning about hiring sales people, the best people, there's a lot more data and science involved than one would think. So it really first starts with how you attract talent to your company. What are the words that you're using in your job description to ensure that you're creating a fair and equitable environment to motivate people to come and work for you.

45:43So that's really where the process starts for me is harm attracting talent. Can I be blunt? Fair and equitable environment to encourage people to motive it. Do you know what honestly sales reps want Sean? They want a company that's selling fast and easy where you get high comp and you get good comps and the sales aren't that freaking hard. Doesn't that sound like a dream? That's what you got two job offers. One way you feel inclusive and in the empowered and another way sales are easy and comes as high. I don't think so, Harry. Now, here's what I've learned in my journey. Let's go back to that example of attracting talent to your company.

46:19Okay? According to Forbes Women, that in general neutral, jaw posts, 74 % of women less likely to interview. Now, hear me out. When in that same description, in the same source, if there are masculine -related tasks or words, like you'll crush it, you'll dominate like those types of words. Only 55 % of women will apply. Now, hold on. According to exactly insights, those that identify as female outperform their male counterparts by 8%. If you, as a sales manager, have a certain profile that you're most attracted to, then that's probably where you're going to go and hire. And so, when I feel this though, I've perfected sales hiring.

47:03It's because I eliminate bias from the process. It's very structured. It's driven by competencies. Okay, so we realized that the words matter in terms of how they impact our funnel of applicants on the talent side. So we use gender -neutral words. We use personality -neutral words. And then what? And then we have like a talent pool. How do we then hire? The next step after you've attracted all this talent to your company, right? You're an advantage because you've got this massive pool to choose from, right? So then what happens next is your proper kickoff. And agreeing on what are the right competencies that we are seeking?

47:42What are the right attributes that we are seeking? And then who is going to do what? So setting up the structured process to ensure you have consistency for the follow through in the interview process. So for example, the high performing reps, they have similar competencies, drive for results, persuasion, negotiation, intellectual curiosity. So you incorporate that in your structured process and you only get so much time with the candidate candidates only gonna give you as a higherer so much time let's say there are three or four people that interview that candidate They all ask the same damn questions.

48:18So you're not getting enough data from that candidate in the short time allowance that you do have So how do you get enough data and how do you make it different? Why it's not like oh tell me about a time when you persuaded someone to do something they wouldn't have otherwise done Great question. The interview for each person, interview E, is highly structured. So Harry, you and I were on the same interview team. Okay, in our software, here's what I'm going to do. I'm seeking and checking out for negotiation, competencies, persuasion competencies, and drive -for -results. Here are the questions I'm going to ask and hear how they will be assessed.

48:55Okay, Harry, you are going to test for these other competencies. Here are the questions you are going to ask and here's how you will assess them. So the interview is very structured and I'm making this up. It's a three hour process for the candidate and every candidate is also going to have the same take -home test. Every candidate is going to go through the same personality test. There's no room for bias, there's no room for repetitive nature, and you follow that process. So you can get the most data for your candidate and that amount of time that you're allowed. Okay, so we have three different interviews over three hours and how they just divide it up just so I understand I'm a founder literally hiring my first sales people one is like Competencies, what are the other two?

49:37Yeah, so the competencies are your big buckets, okay? So let's just use one big bucket as an example drive for results like that that's the bucket They're using then you have three questions that are related to drive for results But you must ask each candidate the same exact questions so they have consistency across the board, right? You don't tweak those questions at all You want to make sure that when you're testing for drive for results like let me give you a specific question, right? So the question that could be consistent is tell me about a time when you were told to call me back in six months What did you do?

50:11What was your action and then what was the result as an example? No, I've got an answer for you actually did this. I emailed not banning or 52 times once every single week with a different email every time related to a tweet that he sent in the prior week with like one of my comments on it I saw that that was like four months ago, right? Yeah, it was a long sale cycle But but yeah, okay, and so you're looking for that story of persistence question for you Yes, do you feel you lose the art of someone's story and understanding them with the rigidity of a formula? I hear you, but it's like me saying I ask the same structured questions in 20 sales.

50:53Because your story is different and I want to understand the fabric of what makes you, you, not a robot. Sure, you can get those stories through that structured process. So, for example, let's go back to that question that you showed about Mark Benioff. I just learned a lot about you and you're craft in the elegance of your answer. You're still capturing a little bit of the art, But what I'm trying to avoid Harry is the unconscious bias that inevitably creeps in to every single interview that all human beings do and that's okay But if I can build in more science in more data driven results and the little amount of time that I do have I'll take that Every time other than the nuance that you're referring to like the art side Okay, I got you and so the competencies are like the three cool buckets that could be drive another one persuasion another one whatever we want to choose and we then do three different interviews for each one correct?

51:49No. So the interview let's say the interview is one hour okay. You and I before we start our process of interviewing in general we're gonna have a kickoff meeting and we're going to agree on these are the core competencies there are probably a making this up. There are six to eight of them. I'm the first interview. I'm gonna interview for these three competencies across nine questions. It's gonna be in a scorecard and then you're gonna be able to see it, the scorecard. Now you, Harry, you've got these three or four competencies and here are the nine questions that you're gonna ask. And they're different from mine.

52:19They must be different. So we get as much data about this camera as we possibly can. So we have that as that structure for those cool pillars. You said about a sales task and a take home task. What do you ask them to do? Is it one on you? Is it one on another company? How do you structure that? Yeah, it really depends Harry. It depends. It's my first sales rep or my first sales manager. If it's a first sales rep It might not be a take home test instead. It could be a C cat test that you would take. It could be a personality test that you could take It could be different types of tests, but when I do take home tests It could be something as simple as what would be your 30 60 and 90 day plan when you start with me That could be it so then you can grasp their intellectual curiosity you can grasp their drive, their passion about your product and the problem that you're solving, it can really be a choose your own adventure on what that take home test could be.

53:12Would you ever hire someone who hasn't done sales before? Yes, and I have many, many times. What's more important, someone's sold the ACV that you're selling or to the industry that you're selling to? I don't have a sexy answer, but what I can say is I have hired teachers before. School, educational teachers, professors into sales. Well, it goes back to the teaching element. There are any big lessons for you on negotiation on comp, and what that tells you about people. I find that it's specifically title in comp, a two of the most revealing parts of a hiring process. Do you have any lessons on this?

53:45I have so many lessons on comp. So first, the biggest lessons I've learned on comp, it is transparency, my biggest lesson. For those that are up to negotiate at final offer, to me that just creates a different economic bias that could come in into that process. So maybe someone's better at negotiating compensation than another, right? So maybe that filters it. With transparency, look, I'm never gonna be the highest paid shop in town. You can always go somewhere else to make more money, but I'm looking for transparency, so everyone knows what they're walking into. Here's the variable pay, here's the salary, and it's just very transparent.

54:24Everyone knows what it is. So I don't waste my time on waste theirs. Transparent pay. The second lesson I've learned is I've moved to a national pay structure. If I live in London, if I live in New York City, if I live in Cleveland, Ohio, it's still the same job, right? You're still performing the same tasks. So that transparent standard pay doesn't really matter. We live in a pan -high rent. I assume you live in London. I assume that you live in New York City, and I will pay you on that high end. Not the highest paid shop in New York City, but I'll pay you on that high end. So transparency and one pay structure.

54:57What are the biggest mistakes people might when they're negotiating comp. They underpay or they overpay. Those are the biggest mistakes. There's great data that exists about how much people are paid for certain roles. It's very transparent, but some people they underpay in a startup and they're trying to overpay them, say, on the equity side. Right? I get that, but that's a mistake. Yeah. What's the right OT level, do you think? So, on the enterprise, a national pay, depending on what your quota would be, it's probably a great place to start, right? So best practice is a five to one ratio. If I'm gonna pay someone 200 pounds sterling, I want them to have a million quid as a goal or as a quota.

55:38Think about what that ratio that you're willing to pay. Now to start up, you may have to sacrifice that a bit to maybe four to one. You need some of what that quota is versus what you're willing to pay. But that's considered best practice, so look at it in that type of way. Then, depending on where you're hiring, you can get plenty of data on what the averages are. How long does it take to ramp to get people to quota? Like you bring me in, like second quarter, does Harry Tanta hit quota? If third quarter, I know it depends on the ACV, but selling in enterprise with large ACVs, how long does that take?

56:08Yeah, so if you're selling into the enterprise and let's use an ACV of 100K, you want to let that rep ramp for about six months. Move slow in order to move fast later. But don't wait those six months to measure their performance. Have stagegeats along the way those six months. But enterprise rep it'll take a good year, right? because the next six months, you ease them into their quota. You want them to be successful at the end of the day. The thing that Martin Kills companies has shown, when you look at the amount of sales reps that leave after two years, it's so high. And so you actually have like six months of productivity in 24 because it takes a year to ramp.

56:43The final six they're thinking about, you know, how they're going to leave. And so you've got six in the middle where they're productive. Doesn't this kill organizations? It does if you let it. And the conversation we had a little bit earlier, a piece of conversation I had earlier, which is in your sales process, you'll know within the first six months if this rep's going to cut it and the enterprise or not. You should. And what I think founders make a mistake is they wait for how many deals that they get a year and a half later. There should be more stage gates. What are the stage gates in the first six months that this should be had to understand the effectiveness of a rapid enterprise?

57:18Certification. So I've always embedded a certification culture within my revenue organization. And so you're testing these sales pros. You're having them test on your product. You're testing them on your narratives. You're testing them on whatever is that you want to test them on. And then when they get in sales cycles, are they graduating from Stage 2 to Stage 3 in the sales cycle or not? What's missing? Listening to the gone conversations or chorus or sales level, wherever you use. But those first six months in the enterprise are very, very critical. How the fuck do I fall cost in 2024, Sean?

57:50Like, you know, everyone's telling me it's harder than ever. everyone saying, I'll see FOs, they're not buying. And I'm sitting here today as a CRO or a CEO, thinking, are we gonna 2X last year? Are we gonna 3X? The short answer is artificial intelligence. That's how you're gonna forecast in 2024. There's technology, shout out to my friends at Clary. There's technology today that's putting a lot more science using the machine learning into what's gonna be the output 90 days out. And frankly, our mining logo side, it's been within 5 % accurate. 90 days out. So that's how you should forecast in 2024.

58:25Use the technology. I have wasted years of my life trying to predict the future in forecasting. Years of my life will never get back and I still can't get it right. I still try so damn hard. But forecasting is very difficult. Do you think sales leaders are very good to stay on the whole? When you look across the sales leader landscape state, you like, yeah, awesome set of sales leaders. or you like I was quite rude about it, the ammo is being useless. Do you feel that most heads of cells are pretty useless? I think it's about half or useless, half or very good. I listen to a bit you did about playbooks.

58:57And first, I would refer to playbooks as sheet music. That's what, made books, fun fact for you. The term playbooks is a sport analogy based on American football. So I prefer like, I use like sheet music instead. Yeah, why sheet music not playbooks? Because I'm auditioning right now for candidates in the future that might come work for me. And I want to make sure that I can attract the right people that work in my organization, because I'm not running an old school playbook. I want to run sheet music and pattern recognition. It's a little bit different. And so the sales leaders that are shit right now, Harry, they're running the old sheet music.

59:31They're trying to get people back into an office where there's high fives and kegs and ping pong, and they feel that that's like the culture that they need to be successful. Where today salespeople, they're more interested in career -bathing. They're more interested in learning and in development. I had one sales rep, one of the highest performers that we have. We're all getting together. Those that live in the same city, and we're having a conversation about when the sales manager said, we were talking about the year -end clothes. And a sales manager said, ah, I miss the sales floor. You know, the gongs and all that low noise and the music.

1:00:04And when the highest performing rep said that, she said, what's the sales floor? So to me, it's the biggest, like, ah, moment. Look, I miss. I want to lean in much harder to the future of sales, not to where we were in the past. And the bit that I heard about what you're saying about playbooks, I agree to a certain extent. There's 75 % of key pillars that make up a sales craft. That is the same, no matter where you go. There's sales strategy, there's talent management, there's operations, that's the same. That you pick up and you bring somewhere else, right? But in every organization, it's different.

1:00:37There are probably 35 key attributes that make up those core four pillars that make up a sales organization. And those might vary from company to company. But to answer your question, Harry, half the sales leaders probably are not gonna make it in the next year or two. The final one, cause I can talk to you all day, but on that sheet music versus playbook, should the founder be the one to create the first sheet music? Or should it be an external head of sales first sales hire? Founders are incredible sales people. They care greatly about the product, they build the product, They typically know everything about the product, which makes them great sales people.

1:01:11I would argue that that sheet music is created by a professional that has the pattern recognition that has seen it before. So I do not believe a founder should build that sheet music or playbook for how we're going to go to market. That's fascinating. I believe they should. If the founder doesn't know, then how are we going to hire someone who's going to do it? If I didn't know the person that I'm selling to, the ACV that I'm how I'm gonna reach them, the message that I'm gonna reach them. There's many different types of sales leaders. I don't know which one to hire if I don't have that play but built out.

1:01:42It's not a wrong assessment that the founders should know all of those things. I agree with you. However, there are professionals that know exactly how to craft that message. Like in sales, go to market motion, three common themes. You got a methodology, process, and behavior. Now, you as a founder might not have that pattern recognition skill set built up enough. to know what those behaviors are that you want to incorporate, or what the segmentation strategy should be, or what methodology or process to use, bring on someone that has that pattern recognition and that expertise that can do probably better than a founder that's never done it before.

1:02:19Yep, nope, I get that. Right, Sean, I could talk to you all day, clearly. So I'm going to happy you with questions unlike the last hour and 20 minutes, and you're going to give me an immediate thought. and we're going to start with what single trait is most important for sales rep to have? Intellectual curiosity. How do you test it? What question? You test intellectual curiosity based on their questions that they ask of you, maybe at the end of your interview. I'm so with you. I always say to founders, they'll say at the end, you know, do you have any questions to me on the process, on the firm, and the best always do have many questions.

1:02:53Yes. What sales tactic has died of death? Discovery. There's too much information that we can extract on our own that we should know a lot about our buyer before we engage with them What's your favorite question to ask in an interview process for a sales rep? Explain the time to me when you were asked to call back in six months. The reason why I love that question Harry is you will expose that person and how they operate pretty quickly To the majority not just say it. I haven't I haven't been asked to go back in six months. No, the majority say oh Oh, that's great. I'll make sure I put it on my calendar.

1:03:28Here's what I'm gonna do in the end term and I'll call you in six months. I've had the majority say that. What's the best answer? The best answer to that question? They refrained the problem and they teach me something that I didn't know about my business right now in that moment. That's the best answer. What other function do sales have the most friction with? Sadly, it's product and marketing because sales people, they want a product that's applicable for everyone, right? So they complain about the product which is wrong. And the second reason why sales wrong is on marketing. They want a fat pipeline of buyers that are ready to buy and they blame marketing for it, which is also wrong.

1:04:02So that's typically where the most conflict is. Tell me to a deal you've had to get really creative to win. What did you do, Sean? Ever's feature. What we're talking about earlier about discounting. It's not about discounting. It's about giving gets. And I've had some of the biggest companies that I must win. And I must have them as a customer, but they'll sit on my customer advisory board. We will promote them in different ways. We will use their product in new ways. They're ways to get creative to win the business But basically people want to buy they just don't want to be sold to and so the way I get creative to win deals Is to make it a no -brainer for that buyer to trust me and to go with me.

1:04:37How do you maintain moral when mist goes happen? It always happens at some point. How do you maintain moral? It's goal visualization Celebrating these small quick wins is very important because there are small wins that happen throughout the day and goal visualization reminding the team of our purpose and our mission and why we do this every day. Reminding the team of the impact that we're having in the market as an example, Harry, over this past year when there's a very low hiring volume that's happening right now, Reenhouse. We have helped over a million people win the job of their dream by using a fair process leveraging Reenhouse software.

1:05:16So I remind people of really what we're building and what we're doing. Seven thousand customers. And we've processed over a million offer letters through our software. This year when no one's hiring, but to answer your question, don't forget the goal visualization. Yeah, we all want to make money and hit our code today. All those things, but you got to go deeper sometimes and get back to it really motivates people because that everyone's motivated by money, shockingly. The final one. What one company sales strategy has most impressed you recently when you look across the landscape? 20VC you. I appreciate what you're building and I now want to because you're creating value.

1:05:51You're drawing someone like me in and you're offering this value to other people that are just like me. And then now I want to buy more of the products that you have. I want my leaders to get exposed to what you're doing. You're trying to sell me anything. But that gets back to the teaching and how buyers want to buy. So I'm impressed with the operation, whether you're meaning to do this or not. I'm impressed by it. I so appreciate that. I've loved this. As you can tell for me, the best shows are when it's really very natural. I definitely feel that this was a natural conversation. Thank you so much, Sean.

1:06:22I've loved doing this. Carrie, it's been a treat. This is such a fun conversation. When are we gonna have this conversation again? Taylor Swift. It's London Taylor Swift. And we'll be live streaming our excursions. Taylor Swift's live event in London. No, I'm obviously joking, but you can check out the full episode in the video of that show on YouTube by searching for 20VC. Sure, I'm incredible there, I love the natural discussion. But before we leave you today, CFOs and controllers, is expense management a painful chore? If yes, sounds like you might use concur. Well, it's time to switch to Brexit.

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