The Exchanges

Q And when we think about skill development, what have been your biggest lessons on how to train reps effectively, especially in this ramp time?

A The mental model that we used is we started with this hypothetical, fully ramped salesperson, uh, this individual who has Every single skill, every single knowledge needed to be successful, you know, in the full gamut of, of selling our solution. Then we said, okay, let's break down all those skills and knowledges into, uh, competencies that we think can be learned in three hours or less. Then let's group them by what is the ideal modality to learn it? Is it something that they can learn on their own? Is it something that they can learn on a zoom call? Is it something that they really need to be in a classroom to learn? Great. Now let's look at the ideal sequence. What's the right sequence so that we can get them to land a good, healthy new logo as early as possible. And then what we did or what we're doing is we've created a learning journey that really spans about almost nine months. And it has three week long trainings, a bootcamp, an intermediate, and an advanced. And then coming out of bootcamp, there's a one, there's a, there's a roughly half a day. There's a three hour remote session that they attend with the same cohort that they went to bootcamp with that goes deep on one competency. And so, what we end up with is people coming out of boot camp able to do pipeline generation. They're able to have a conversation, start, start meetings, they're able to do discovery, do a…

AI assessment note: “we've created a learning journey that really spans about almost nine months.”

Q It is great to do it in person as well. It makes it so much more special. I love to start with context though. When did you first realize that you had this love of sales first?

A Probably as a teenager. Um, I had a cousin, uh, my cousin Thais was dating a guy who was a manager of a clothing store, and I think I was 14 or 15 at the time, and I had worked, you know, for several years mowing lawns and raking leaves and doing odd jobs, uh, paid by the hour, and, uh, he decided to give me a shot at the store. He would let me come in on the weekends, And sell men's suits. And, uh, the commission rate was 10% and the suits were 800 to a thousand dollars. And over the course of a weekend, I could usually sell one suit, maybe two, maybe three. Uh, and so to make a hundred bucks in the air conditioning in the mall was pretty amazing. And I thought, hmm, this, there's something to this.

AI assessment note: “Probably as a teenager.”

Q Your time is going to be so conflicted or change differently by suddenly having pipeline generation as a core part of it and an expectation. How do you advise reps on time allocation? Now pipeline generation is a core part of that expectation.

A Yeah. First, you have to agree that pipeline generation is good. You can also say that roughly excellence in pipeline generation equals excellence in sales. Someone who's got a massive pipeline that misses some things in the sales cycles, They're probably still gonna do very well. Someone that executes beautifully, but doesn't have enough pipeline, they're gonna miss their number. And so that's the first thing. Let's agree that pipeline generation by the AE is worthwhile. If so, uh, if they agree with that, and I feel very strongly that that's the case, then roughly a third of your time, so maybe 20% of your time, one day a week, is dedicated to just Outbound, you know, cold calling. And then there's another probably 10 to 15% of your time that is devoted to prep for the cold calling and follow up from the cold calling. So that's kind of how you get to the 30, how I get to the 35%.

AI assessment note: “roughly a third of your time, so maybe 20% of your time, one day a week”

Q Which would you say are more often non-negotiable for you? I know it's Situation dependent, but more often than not non-negotiable.

A Um, I've spent almost my entire career at, uh, challenger companies. And so if you're going to disrupt a marketplace, um, the risk associated with hiring someone that hasn't been at a challenger company is really, really high. So that one is a near non-negotiable. Pipeline generation. Hiring AEs that have not built their own pipeline, that one is non-negotiable, because if they say they will, if they say they want to, um, they just don't know how hard it is, or they don't remember, maybe they did it as SDRs a long, long time ago, so that, that's a really big risk. That's a, that's a kind of a non-negotiable. Maybe they've only sold into mid-market accounts, and they've only sold deals in the, 50 to 150 K range. We're going to put them in enterprise selling 500 K deals with many more stakeholders. But again, we think they're really smart. We think their drive is really high. And so we, that's more negotiable. So those are, those are some of the things that I'd negotiate.

AI assessment note: “Hiring AEs that have not built their own pipeline, that one is non-negotiable”

Q And when we think about skill development, what have been your biggest lessons on how to train reps effectively, especially in this ramp time?

A The mental model that we used is we started with this hypothetical, fully ramped salesperson, uh, this individual who has Every single skill, every single knowledge needed to be successful, you know, in the full gamut of, of selling our solution. Then we said, okay, let's break down all those skills and knowledges into, uh, competencies that we think can be learned in three hours or less. Then let's group them by what is the ideal modality to learn it? Is it something that they can learn on their own? Is it something that they can learn on a zoom call? Is it something that they really need to be in a classroom to learn? Great. Now let's look at the ideal sequence. What's the right sequence so that we can get them to land a good, healthy new logo as early as possible. And then what we did or what we're doing is we've created a learning journey that really spans about almost nine months. And it has three week long trainings, a bootcamp, an intermediate, and an advanced. And then coming out of bootcamp, there's a one, there's a, there's a roughly half a day. There's a three hour remote session that they attend with the same cohort that they went to bootcamp with that goes deep on one competency. And so, what we end up with is people coming out of boot camp able to do pipeline generation. They're able to have a conversation, start, start meetings, they're able to do discovery, do a…

AI assessment note: “The mental model that we used is we started with this hypothetical, fully ramped salesperson”

Q Great. If you're an early stage founder, how do you think about the rep training and being as effective as possible?

A Yeah. You wouldn't, you wouldn't be able to afford, uh, from, you know, from a financial perspective, but also just in terms of bandwidth, you wouldn't be able to afford to build that. And frankly, you wouldn't know what to build with an early stage. That's why I go back to what I said before is for a founder at a, you know, let's say a series, a company, I would get some really smart, hardworking, uh, you know, enthusiastic individual contributors and go build it. And you won't, and you'll be able to build your enablement after you've closed, you know, 10 or 20 customers, and you're like, okay, now I've closed, let's say, 20 customers, which means I've probably failed to close another 60 customers, so I've got 80 sales cycles of experience, now I can identify the things to do, the things not to do, and I can build V-one of my training based on that, and maybe that's just two or three days.

AI assessment note: “build your enablement after you've closed, you know, 10 or 20 customers”

Q Yeah, yeah, yeah, but it's throughout the show I've been thinking this. It's just like, when you reflect on your biggest hiring mistakes, what are the ones where you look back now and go, ah, that's one I've made time and time again?

A Well, hopefully you don't make the same mistake over and over, but one that I have made, Um, that was particularly painful, um, was to hire someone based on, uh, relationships. And it was early in my career and I was at a startup and this person was very successful at, um, at EMC. And the, the numbers that they had posted and the relationships that they had were so senior. I thought this guy is just going to light it up. And I brought him on and I spent the first three months going on these fancy lunches at steak houses in New Jersey with these very senior folks who had, who were completely irrelevant to the product that we sold and, you know, fancy lunch. And the conclusion of the fancy lunch is, oh yeah, I'll ask so-and-so who's the person you need to get to and see if they're interested. And the vast majority We're not. And so nothing came of it. And what I realized is that this individual lacked the, the skills to go build pipeline. He just didn't know how to do it. He was a relationship seller, a competent guy, a hardworking guy, but the skills to actually go and call a stranger and deliver a value prop and have that resonate and, and, you know, secure a meeting and then come in and do a great meeting. All of those skills just He didn't have them. And so that was a painful because he was expensive and I had advocated for him and we had to go like outside of the standard hi…

AI assessment note: “was to hire someone based on, uh, relationships”

Q Do you agree with Jason Lampkin who says that you should always hire two reps at the same time? And subtly enforce this element of competition?

A Yes, but for a different reason. So I do think that having multiple reps co-located is far, far better. You know, at MongoDB, you mentioned that you talked to Dave. At MongoDB, we hired a lot of people, and, uh, our attrition was higher than we wanted it to be, and so we did a lot of analysis on attrition, and what we found is that lone rangers, and we meant that meaning when we have a single employee in a You know, if we have a single rep in a city and no one else at MongoDB lives in that city, their attrition rate was like four times higher. It's so hard to ramp when you're all by yourself, when that little tiny, that quick question that would have taken 10 seconds to lean over and ask the person next to you, when that now requires you to schedule time with someone and forget it. So the likelihood of failure is so much higher. So Sure, the competitive aspect is part of it, but I think the bigger part of it is just helping each other, so I'm a big advocate of hubs, and so I think at minimum you want two sales, if it's a company, if it's a, if it's a product where you have a sales engineer, two sales people and a sales engineer, that's like the minimum profile for a hub.

AI assessment note: “Yes, but for a different reason. So I do think that having multiple reps”

Q Your time is going to be so conflicted or change differently by suddenly having pipeline generation as a core part of it and an expectation. How do you advise reps on time allocation? Now pipeline generation is a core part of that expectation.

A Yeah. First, you have to agree that pipeline generation is good. You can also say that roughly excellence in pipeline generation equals excellence in sales. Someone who's got a massive pipeline that misses some things in the sales cycles, They're probably still gonna do very well. Someone that executes beautifully, but doesn't have enough pipeline, they're gonna miss their number. And so that's the first thing. Let's agree that pipeline generation by the AE is worthwhile. If so, uh, if they agree with that, and I feel very strongly that that's the case, then roughly a third of your time, so maybe 20% of your time, one day a week, is dedicated to just Outbound, you know, cold calling. And then there's another probably 10 to 15% of your time that is devoted to prep for the cold calling and follow up from the cold calling. So that's kind of how you get to the 30, how I get to the 35%.

AI assessment note: “roughly a third of your time, so maybe 20% of your time, one day a week”

Q So just so I know how we structure the week, it kind of starts on the Thursday with the planning that progresses through to action day on Tuesday. Tuesday is when we do action. We are actually hitting the accounts, hitting the targets. And then for the rest of the week we're harvesting?

A Yeah, there's a couple, couple other things. So yeah, Thursday we declare, um, Friday and over the weekend we prepare. Monday morning we review the preparation, Monday afternoon we train, Tuesday we do PG all day, and then obviously throughout the week there's follow-up, there's harvesting, and then I love to do a wrap-up on Friday, so I typically run that myself, and it's the whole sales team, and we celebrate the PG success of the week, and we tell stories of success, we tell stories about Uh, successful meetings. We also tell some stories about opportunities that have been created from previous week's PG, and it really builds, I think, an enthusiasm, a belief, and it really, and it reinforces this thing we do that's so important, so powerful, but also so hard. And so that's kind of the, the circle of life, if you will.

AI assessment note: “Thursday we declare, um, Friday and over the weekend we prepare. Monday morning we review”

Q Yeah, yeah, yeah, but it's throughout the show I've been thinking this. It's just like, when you reflect on your biggest hiring mistakes, what are the ones where you look back now and go, ah, that's one I've made time and time again?

A Well, hopefully you don't make the same mistake over and over, but one that I have made, Um, that was particularly painful, um, was to hire someone based on, uh, relationships. And it was early in my career and I was at a startup and this person was very successful at, um, at EMC. And the, the numbers that they had posted and the relationships that they had were so senior. I thought this guy is just going to light it up. And I brought him on and I spent the first three months going on these fancy lunches at steak houses in New Jersey with these very senior folks who had, who were completely irrelevant to the product that we sold and, you know, fancy lunch. And the conclusion of the fancy lunch is, oh yeah, I'll ask so-and-so who's the person you need to get to and see if they're interested. And the vast majority We're not. And so nothing came of it. And what I realized is that this individual lacked the, the skills to go build pipeline. He just didn't know how to do it. He was a relationship seller, a competent guy, a hardworking guy, but the skills to actually go and call a stranger and deliver a value prop and have that resonate and, and, you know, secure a meeting and then come in and do a great meeting. All of those skills just He didn't have them. And so that was a painful because he was expensive and I had advocated for him and we had to go like outside of the standard hi…

AI assessment note: “one that I have made, Um, that was particularly painful, um, was to hire”

Q When we're testing out these kind of skills and the non-negotiables and negotiables, we're going to get into pipeline generation. I have to later, but are we doing case studies? Are we doing take home assignments? Are we doing anything physically active to determine these skills?

A We're reaching a conclusion, uh, or we're developing an opinion on where they are in terms of maturity on the skill through interviews and back channels. I'm a big advocate for at the end of the process. We call it a challenge. We have an event where they have a couple of days to go, uh, think about some questions, prepare a presentation and come back and present it. But that's more of a validation Around the decision at the end. It wouldn't be fair, I think, to a candidate to do that early on, because it does take work, and so once as a hiring team we develop conviction around a candidate, we'll do the challenge just to, like, make sure we didn't miss anything.

AI assessment note: “We call it a challenge. We have an event where they have a couple of days”

Q What sales tactic has died a death? We've a la poubelled outbound that is still alive and well. What has died a death?

A Closing. I'm a closer. I know how to just convince this idea that you can coerce a customer or do some psychological gymnastics to get someone to sign a piece of paper when they weren't actually intending to. First of all, if you do, that's a, that deal's probably going to churn later, or they're going to find a way to rescind the order. But, um, I don't believe salespeople sell. Buyers buy. All salespeople can do is create an environment that is conducive to that purchase decision. How do you create that environment? Well, by doing good discovery, by finding challenges, by educating on how your solution meets those challenges. And once you do that, They want to buy, but the art of closing, that's baloney.

AI assessment note: “Closing. I'm a closer.”

Q It all starts with bluntly bringing reps on, and I spoke to Manny, and I spoke to, um, um, Dev at Mongo before, and they both said that you're amazing when it comes to hiring sales talent, so I wanted to start there. What are the single biggest lessons for you when it comes to effectively recruiting sales reps?

A I think it's important to think about the job that needs to be done. Arrive at a conclusion, a well-formed opinion around whether a candidate is capable of doing that job, and I think a trap and a mistake that people make is, um, Over rotating on what they have done in the past, and assuming that success in the past predicts success in the future. Um, certainly a track record of failures is, uh, is something to, to be thoughtful about and to avoid, but success in the past, you have to be able to, um, break down what needs to happen in the future, And identify what skills or what attributes are required in order to accomplish this, uh, outcome in the future, and then figure out almost like take a battery of what this person brings and how much of what they need in the future do they already bring. Investigate or interrogate what they've accomplished in the past, what their life journey is like, and form an opinion around their innate attributes so that, um, You can start to, to, to have an opinion around the likelihood of their success in the job that you're trying to, to fill.

AI assessment note: “a trap and a mistake that people make is, um, Over rotating on what they have done”

Q I want to get to the pipeline generation. You said it there. Manny was like, pipeline generation Tuesdays are famed with Carlos, and it was so central to how you acted with Mongo and how you execute so well. And so first, I just want to start by asking, we have SDRs. We have demand gen. Why do we need to have this extreme focus on pipeline generation for reps?

A There's a few reasons. Reason number one, more pipeline. Great. It's like cowbell, the more the better. Um, reason number two, think about when, um, when a salesperson gets stuck in a deal, why are they stuck? They're stuck because maybe they're too low and they can't get high, or they're in one division and they can't get over to the other division. How do you get unstuck? You PG into the person that you need to be in, to be at. You PG into the Uh, more senior person. You PG into the other, uh, division. And so the ability to generate pipeline will drive, um, will, will lead to a higher win rate on existing business. What else? Well, if you have an organization where pipeline generation is outsourced, let's say to another role, It's a natural tendency for salespeople to get, um, more and more finicky around what inbounds or what leads are worth their time, are worth working. And so the next thing you know, if you, if you take that to its logical conclusion, it's, and I've seen this, I won't mention the company, but I've seen a company where the AEs said, hey, the definition of an Of a lead worthy of me working is the customers ready to see a demo and they have, they have agreed with the SDR that if the demo goes well, they want to quote and they're ready to buy after that. So that's like 80% of the sales cycle is done and the sales are, and so now in that kind of a scenario, y…

AI assessment note: “There's a few reasons. Reason number one, more pipeline.”

Q Do you agree with Jason Lampkin who says that you should always hire two reps at the same time? And subtly enforce this element of competition?

A Yes, but for a different reason. So I do think that having multiple reps co-located is far, far better. You know, at MongoDB, you mentioned that you talked to Dave. At MongoDB, we hired a lot of people, and, uh, our attrition was higher than we wanted it to be, and so we did a lot of analysis on attrition, and what we found is that lone rangers, and we meant that meaning when we have a single employee in a You know, if we have a single rep in a city and no one else at MongoDB lives in that city, their attrition rate was like four times higher. It's so hard to ramp when you're all by yourself, when that little tiny, that quick question that would have taken 10 seconds to lean over and ask the person next to you, when that now requires you to schedule time with someone and forget it. So the likelihood of failure is so much higher. So Sure, the competitive aspect is part of it, but I think the bigger part of it is just helping each other, so I'm a big advocate of hubs, and so I think at minimum you want two sales, if it's a company, if it's a, if it's a product where you have a sales engineer, two sales people and a sales engineer, that's like the minimum profile for a hub.

AI assessment note: “Yes, but for a different reason. So I do think that having multiple reps co-located”

Q EQ, empathy, that pain tolerance, all feels a little bit like a game of art. And then we see the world today and it feels a lot more scientific. How do you think about sales being art or science?

A Yeah, I think art is what we call something when we don't understand it yet. Um, you know, people could say, oh, you know, Picasso, that's, that's art. How does he do it? And then you have, you know, students studying for years, and then they break it down. Well, it's the colors and the shapes or whatever it is that's the basis of, uh, of Picasso's art. And so I think like anything, um, there, there are people who are savants, who are gifted, and there are people who can, uh, Connect dots that others don't see, but then, um, others can, can follow, can learn, and can, can replicate those things, so I think it's more science than art, candidly.

AI assessment note: “so I think it's more science than art, candidly.”

Q And then can have incredibly granular, detailed use cases, insights about those industries. How do you feel about very verticalized playbooks?

A I have a different opinion about the playbook versus verticalized teams. Now, let me caveat this. Um, if you have a solution where it's just radically different in one, like ERP, how you implement ERP at a company that, you know, at a paint company versus a software company is, is completely, is completely different. So much so that it would be unreasonable to ask a sales rep to be able to do both. Centralizing knowledge around what's going on in an industry so that salespeople, um, can be more relevant more quickly with accounts in that industry, I think is absolutely a thing to do. And, um, even if you have a horizontal solution, Like, you know, like a technology solution, IT infrastructure. The challenges, the things that, uh, customers in a particular vertical cares about are very, very different. So empowering salespeople with that is, is really, uh, is really valuable. Verticalizing the sales force when you have a horizontal solution, I think cuts, um, it cuts against meritocracy because there's typically going to be some verticals that are better than others. Like maybe, oh, Financial services is just like the cat's meow. What a great, you know, it's such a great fit. And so, Hey, the team in New York, are they amazing or do they have all the banks? And so mixing up the territories, uh, I think, um, is, is, is really good for, you know, for, for meritocracy and for havin…

AI assessment note: “Centralizing knowledge around what's going on in an industry... is absolutely a thing to do.”

Q How would you do it differently? Are you able to let go of someone after six months if enterprise sales cycles are generally a year?

A Just like I said, because you've got milestones along the way, and so if they're not If they're not achieving the leading indicators to success, then we figure out why and we try to fix it. And if it's fixable, great. They're back on track. And if it's not fixable, then, you know, that means they're in the wrong role or at the wrong company. And so, yeah, we can, I've, you know, it's, it's not a happy day, but we've parted ways with people at bootcamp. It was, it was clear in their first month that, you know, we'd made a mistake and, you know, we, we apologize for that because we hired them. But, um, why wait nine months and waste their time and, and waste our time and opportunity costs?

AI assessment note: “we've parted ways with people at bootcamp. It was, it was clear in their first month”

Q EQ, empathy, that pain tolerance, all feels a little bit like a game of art. And then we see the world today and it feels a lot more scientific. How do you think about sales being art or science?

A Yeah, I think art is what we call something when we don't understand it yet. Um, you know, people could say, oh, you know, Picasso, that's, that's art. How does he do it? And then you have, you know, students studying for years, and then they break it down. Well, it's the colors and the shapes or whatever it is that's the basis of, uh, of Picasso's art. And so I think like anything, um, there, there are people who are savants, who are gifted, and there are people who can, uh, Connect dots that others don't see, but then, um, others can, can follow, can learn, and can, can replicate those things, so I think it's more science than art, candidly.

AI assessment note: “so I think it's more science than art, candidly.”

Q When you think about questions around a hire from that approval board or the people involved in the process, what are the most common reasons Why there is conflict in a hiring decision for sales reps?

A I think it's human nature that we tend to index around our own strengths. When we see pieces of ourselves in someone else, I think it's very tempting to become enamored with that and then to miss other gaps. And so if you've got in a hiring, you know, in a hiring chain of command, you've got people that are quite different. One person that's Super, uh, charismatic, has super high EQ. Another person that's super process oriented. The process oriented person might miss that this person is a little awkward, or the high EQ person might miss that this person is, is kind of like not, not very tight on process. And so that, that would be one area where you have disagreements.

AI assessment note: “we tend to index around our own strengths”

Q What sales tactic has died a death? We've a la poubelled outbound that is still alive and well. What has died a death?

A Closing. I'm a closer. I know how to just convince this idea that you can coerce a customer or do some psychological gymnastics to get someone to sign a piece of paper when they weren't actually intending to. First of all, if you do, that's a, that deal's probably going to churn later, or they're going to find a way to rescind the order. But, um, I don't believe salespeople sell. Buyers buy. All salespeople can do is create an environment that is conducive to that purchase decision. How do you create that environment? Well, by doing good discovery, by finding challenges, by educating on how your solution meets those challenges. And once you do that, They want to buy, but the art of closing, that's baloney.

AI assessment note: “Closing. I'm a closer. I know how to just convince this idea”

Q When we're testing out these kind of skills and the non-negotiables and negotiables, we're going to get into pipeline generation. I have to later, but are we doing case studies? Are we doing take home assignments? Are we doing anything physically active to determine these skills?

A We're reaching a conclusion, uh, or we're developing an opinion on where they are in terms of maturity on the skill through interviews and back channels. I'm a big advocate for at the end of the process. We call it a challenge. We have an event where they have a couple of days to go, uh, think about some questions, prepare a presentation and come back and present it. But that's more of a validation Around the decision at the end. It wouldn't be fair, I think, to a candidate to do that early on, because it does take work, and so once as a hiring team we develop conviction around a candidate, we'll do the challenge just to, like, make sure we didn't miss anything.

AI assessment note: “We call it a challenge. We have an event where they have a couple of days”

Q How would you do it differently? Are you able to let go of someone after six months if enterprise sales cycles are generally a year?

A Just like I said, because you've got milestones along the way, and so if they're not If they're not achieving the leading indicators to success, then we figure out why and we try to fix it. And if it's fixable, great. They're back on track. And if it's not fixable, then, you know, that means they're in the wrong role or at the wrong company. And so, yeah, we can, I've, you know, it's, it's not a happy day, but we've parted ways with people at bootcamp. It was, it was clear in their first month that, you know, we'd made a mistake and, you know, we, we apologize for that because we hired them. But, um, why wait nine months and waste their time and, and waste our time and opportunity costs?

AI assessment note: “we've parted ways with people at bootcamp. It was, it was clear in their first month”

Q And then can have incredibly granular, detailed use cases, insights about those industries. How do you feel about very verticalized playbooks?

A I have a different opinion about the playbook versus verticalized teams. Now, let me caveat this. Um, if you have a solution where it's just radically different in one, like ERP, how you implement ERP at a company that, you know, at a paint company versus a software company is, is completely, is completely different. So much so that it would be unreasonable to ask a sales rep to be able to do both. Centralizing knowledge around what's going on in an industry so that salespeople, um, can be more relevant more quickly with accounts in that industry, I think is absolutely a thing to do. And, um, even if you have a horizontal solution, Like, you know, like a technology solution, IT infrastructure. The challenges, the things that, uh, customers in a particular vertical cares about are very, very different. So empowering salespeople with that is, is really, uh, is really valuable. Verticalizing the sales force when you have a horizontal solution, I think cuts, um, it cuts against meritocracy because there's typically going to be some verticals that are better than others. Like maybe, oh, Financial services is just like the cat's meow. What a great, you know, it's such a great fit. And so, Hey, the team in New York, are they amazing or do they have all the banks? And so mixing up the territories, uh, I think, um, is, is, is really good for, you know, for, for meritocracy and for havin…

AI assessment note: “Centralizing knowledge around what's going on in an industry... is absolutely a thing to do”

Q Okay, so we don't use discounting then, and the deal slips. Okay, deal slips into next quarter, and you're my boss, and you're the sales leader, and I say, Cass, I'm sorry, the deal just slipped. It slipped. What do you say to me?

A Having a deal slip is a painful thing, and to have pain and not, uh, extract the learning is, is, is really, is to squander an opportunity. Pain is a great teacher, uh, or failures are a great teacher. And so if we revel in that pain and really analyze, we have to figure out, okay, why, why did the deal slip? And the answer has to be something we failed to do or something we did that we shouldn't have done. And therefore, what must we learn or what should we learn and what's, what must we do differently, uh, in the future? That's the key thing. Of course, deals are going to slip. We're going to lose deals. You know, shit happens. Um, let's figure out why it happened, what we learn, and, and, and let's get better as a result.

AI assessment note: “let's figure out why it happened, what we learn, and, and, and let's get better”

Q Is that, sorry, is that scalable? The manager is having to look through, what, 10 different, like, target people's accounts? There's too many people for them to be going, oh, Jill's my neighbour, oh, I know that this piece of the report is perfect for them. Is that possible to ask them to do that across the board?

A Yeah, it takes, takes an hour or two. You know, remember, the manager is in the role because they know, they know what they're doing, they've got some experience, and so it's not to say that the manager's gonna have a really great insight for every single focus account, But they'll, as they scan the 10 accounts, there'll be two, three, four accounts where they have an idea. Oh, Barclays. I read an article two years ago. Let me find it. Or I heard something on Bloomberg radio. Let me go find it for you. Um, and so then, so that's the PG prep. So the reps got, um, the reps got help from marketing, help from their manager. You know, you might even have a team of, uh, data analysts that Help with the PG prep. I'll talk about that in a moment. Um, then Monday morning, there's a, a conversation, a one-on-one conversation between the manager and the AE to review, review their PG prep. And this is where the manager really digs in to make it better. Obviously it's an accountability event to make sure that the prep was done, but more importantly, it's about making the prep even better. Hey, I don't think you're, Aiming sufficiently high. You don't have the CIO in here. You don't have any senior people or they're too high. You know, the, the Jamie Dimon is not going to respond to an email about, uh, you know, cloud cost management. So, uh, so adjust the PG prep Monday afternoons is a grea…

AI assessment note: “Yeah, it takes, takes an hour or two.”

Q Okay, so then we don't. How do we form structure around it? Can you take me to pipeline generation Tuesdays? Like, what is that? How do you structure it?

A Before I get into the weekly cadence, let's say for the quarter, I'm an enterprise salesperson. I might, um, uh, I might select from my territory, 20 top targets for the quarter. And I'll sit down with my manager the first or second day of the quarter and I'll validate. Hey, are these good? Yeah. Oh, you missed. This one's not very good. Great. Ok, now I've got 20 accounts that I'm gonna go after over the next three months. On a given week, I'm gonna focus on one or two accounts. Maybe three if they're on the smaller side. So let's say an average of two. I declare those on Thursday. Those are my focus accounts for next week. Thursday night, I declare them, which is just, I click a couple of things in Salesforce. Now, over the course of Friday and over the weekend, as a salesperson, I do some research. What's the research? I, um, look at what the execs are saying on social media. I read the 10 K. Now you can use AI to Make a lot of this stuff so much better. I researched the company. Um, I look at what, um, I look at their job postings. I look at what you might even go in looking blind and see what their engineers are saying. See what people are griping about. I try to get a sense for what's really going on inside the company. And then I develop a hypothesis about something that I think they care about that we can impact. Maybe I developed two or three hypotheses. This is for th…

AI assessment note: “Before I get into the weekly cadence, let's say for the quarter”

Q How long do you give someone to ramp?

A I think what you're asking is when do you sort of declare Uh, you know, failure in part ways. I think ideally what you have is you have a series of milestones over the course of someone's journey that start in the first few weeks. They go to training, they prepare for training. Um, they go to training. How did they do on the entrance exam? How did they do in their role play? How did they do in the, you know, uh, final exam? Were they able to get meetings coming out of their first, uh, you know, bootcamp? Were some of those early meetings converting? Are they able to get to an economic buyer in their third month? So there's all sorts of milestones along the way. And so if you sort of decompose a salesperson's ramp to productivity, then what you can do is you can identify at any moment, hopefully very, very early if they're going off course and you can figure out why. A lot of companies, You know, they, they'll, they'll start to worry about someone that hasn't sold at, you know, nine, 10, 1112 months, and so then they'll make a decision to part ways at 18 months. That's so expensive, not just in terms of...

AI assessment note: “you have a series of milestones over the course of someone's journey”

Q It all starts with bluntly bringing reps on, and I spoke to Manny, and I spoke to, um, um, Dev at Mongo before, and they both said that you're amazing when it comes to hiring sales talent, so I wanted to start there. What are the single biggest lessons for you when it comes to effectively recruiting sales reps?

A I think it's important to think about the job that needs to be done. Arrive at a conclusion, a well-formed opinion around whether a candidate is capable of doing that job, and I think a trap and a mistake that people make is, um, Over rotating on what they have done in the past, and assuming that success in the past predicts success in the future. Um, certainly a track record of failures is, uh, is something to, to be thoughtful about and to avoid, but success in the past, you have to be able to, um, break down what needs to happen in the future, And identify what skills or what attributes are required in order to accomplish this, uh, outcome in the future, and then figure out almost like take a battery of what this person brings and how much of what they need in the future do they already bring. Investigate or interrogate what they've accomplished in the past, what their life journey is like, and form an opinion around their innate attributes so that, um, You can start to, to, to have an opinion around the likelihood of their success in the job that you're trying to, to fill.

AI assessment note: “a mistake that people make is, um, Over rotating on what they have done”