The Exchanges

Q On that, sorry, let's just start on that. Sales segmentation, does that need to change as you move upmarket?

A Absolutely. Yeah, I mean, when I, when, you know, when I came into, at both Slack and Glean, when I joined Slack, I immediately, after we got to about ten million in revenue, Cut the team into SMB and enterprise, and I basically said enterprise is a thousand employees and above, SMB is below, and that way we just sort of put the resourcing, the more expensive sales resourcing, on those bigger accounts. Now, at Slack, it was a lot of inbound, but even that segmentation is important to do, so you at least get your true, like your sellers starting to think about upmarket Inbound at a minimum. At Glean, when I joined, we had real great success in that mid-market segment. We had strong sellers, about like eight of them, and we decided very quickly with the team to say, we've got to move up market, let's cut it at 2000 employees and above, and, and the below will be serviced by a smaller subset of the team. And that helped us start to accelerate moving up, but you're right, it's not like, because you only have eight AEs or 10 AEs, you're not all of a sudden touching every Fortune 100 and able to do deals overnight, and so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are going to prove success at a Fortune 100, Like T-M…

AI assessment note: “Absolutely. Yeah, I mean, when I, when, you know, when I came into”

Q How willing are you to do small contract, and what would your advice be to do small contracts with mega customers where they're like, hey, land and expand?

A I think you need to be very willing to do that. Now, the key thing that we've learned, and I, you know, learned this at Slack as well, but at Glean, You've got to have success criteria. You've got to have, okay, we're going to do, let's say for Fortune, 100 company, we're going to do a 100,000, a 150,000 land deal, but you have commercial alignment and executive alignment on what are the success criteria that we need to hit to get to that seven figure contract. That's how we try to do it in structure. It's a very timely topic was we're like debating it even more as a, as a go to market team. We had one Fortune 100 companies say, we want to test how you're, how we're lowering call resolution time with Glean relative to the other solution we had and the competitors. It was very time bound. It was very specific. And we're able to tie that back exactly to dollars. So that land slash paid POC in some ways turned into the seven figure contract.

AI assessment note: “I think you need to be very willing to do that.”

Q How willing are you to do small contract, and what would your advice be to do small contracts with mega customers where they're like, hey, land and expand?

A I think you need to be very willing to do that. Now, the key thing that we've learned, and I, you know, learned this at Slack as well, but at Glean, You've got to have success criteria. You've got to have, okay, we're going to do, let's say for Fortune, 100 company, we're going to do a 100,000, a 150,000 land deal, but you have commercial alignment and executive alignment on what are the success criteria that we need to hit to get to that seven figure contract. That's how we try to do it in structure. It's a very timely topic was we're like debating it even more as a, as a go to market team. We had one Fortune 100 companies say, we want to test how you're, how we're lowering call resolution time with Glean relative to the other solution we had and the competitors. It was very time bound. It was very specific. And we're able to tie that back exactly to dollars. So that land slash paid POC in some ways turned into the seven figure contract.

AI assessment note: “I think you need to be very willing to do that.”

Q On that, sorry, let's just start on that. Sales segmentation, does that need to change as you move upmarket?

A Absolutely. Yeah, I mean, when I, when, you know, when I came into, at both Slack and Glean, when I joined Slack, I immediately, after we got to about ten million in revenue, Cut the team into SMB and enterprise, and I basically said enterprise is a thousand employees and above, SMB is below, and that way we just sort of put the resourcing, the more expensive sales resourcing, on those bigger accounts. Now, at Slack, it was a lot of inbound, but even that segmentation is important to do, so you at least get your true, like your sellers starting to think about upmarket Inbound at a minimum. At Glean, when I joined, we had real great success in that mid-market segment. We had strong sellers, about like eight of them, and we decided very quickly with the team to say, we've got to move up market, let's cut it at 2000 employees and above, and, and the below will be serviced by a smaller subset of the team. And that helped us start to accelerate moving up, but you're right, it's not like, because you only have eight AEs or 10 AEs, you're not all of a sudden touching every Fortune 100 and able to do deals overnight, and so what we did was strategically pick one or two key bets that we wanted to get to prove success in. T-Mobile became that account for us at Glean. Not just a sales team, as a company and leadership team, we said, we are going to prove success at a Fortune 100, Like T-M…

AI assessment note: “Absolutely. Yeah, I mean, when I, when, you know, when I came into”

Q What was the hardest sales skill to learn for you?

A I think rejection. Just this idea that, man, like, I, I feels, I feel a little bit of, you know, shame, you know, like, my, I started my, just to give some background, I started my sales career doing outbound, almost in-person sales, doing print ad sales in Cambridge, Massachusetts. I was selling to mom and pop shops on buying ads in this guidebook called The Unofficial Guide to Life at Harvard. I felt bad interrupting, like, a Small business owner who was trying to make, like, a little money, and so just the, the, the sort of, like, almost the shame of, like, interrupting their life, and then that rejection of them saying, hey, look, I am not interested, you know, please get away. Like, that is just, like, a really hard thing, because it's, it's just failure, failure, failure, failure.

AI assessment note: “I think rejection. Just this idea that, man, like, I, I feels, I feel”

Q Like it is the one area where I think most early stage founders get most wrong. You've hired exceptional sales teams. How do you run a process when adding to the sales team? What does that look like?

A Understand the deep history of the individual Over a chronological period of time. I didn't realize that that was a hiring methodology until Bob Fratty taught me that at Slack, which is kind of this who hiring, the who hiring method is what we call a chronological interview. Like, I ask people, what, what did you do in high school? Like, what were you proud of in high school? Not because, I don't care, and then I say, why did you go to the college you went to? What was your proudest accomplishment in college? And I do that through every Why did you leave the first job you did? Why did you go to the next job? And I go, really try to understand, because what you can build is an understanding of, like, the deep motivations that people have.

AI assessment note: “Understand the deep history of the individual Over a chronological period of time.”

Q Yeah, I do want to retain some sense of, you know, structure, otherwise my mind just goes everywhere. Slack was an incredible journey for you. Uh, it really shapes a lot of how one thinks when has, when one sees such a transformational journey. What are one or two of the biggest takeaways for you from Slack, and how did that impact how you think as a sales leader?

A The number one, number one takeaway that I, I've I've brought to Glean. It's what I give to other, you know, founders I advise and just is how important it is to have the collaboration and like collaborative tension between R&D and GTM. So when I was at Slack early days, it was interesting. Like I was struggling to get the organization to think about supporting the enterprise. We were so focused on just like the, like the inbound and the PLG. That we were starting to run into challenges with supporting and getting to customer success on the Comcast, the Walmarts that were some of those early, earlier enterprise customers, and so I think driving feedback to the product organization, challenging them, getting them on calls.

AI assessment note: “how important it is to have the collaboration and like collaborative tension between R&D and GTM”

Q What does everyone think they know about selling AI tools that they get totally wrong?

A I think that, um, that it's gonna be Easy to implement is, is what they get wrong. And that's simply, I mean, we talked about it already. I think that lots of, lots of even our AEs that we have, like we are educating them, even though our product is relatively compared to the market, easy to implement. We're, we're, we're telling them set the right expectations, make sure that you have a deployment success plan. You know, I, I took a page out of Dave Schneider's book from ServiceNow and We're implementing a system where we're not paying AEs on their deals unless they have an approved deployment success plan filled out. I think one of the things that, you know, just looking at, you know, I don't know, talking to others, like I care very much about the customer success side. I own that function at Glean, so I own the pre-sales, post-sales, and that's a, for me, a very important part to it, but I think going back to your question, it's a lot of companies are Getting the big deals done, and then assuming, okay, we can figure out the deployments later, and that's what they get wrong.

AI assessment note: “that it's gonna be Easy to implement is, is what they get wrong.”

Q I'm a salesperson. I'm brilliant at packaging. Uh, how do you actually determine true grit quality in my sales skills when I answer your questions beautifully?

A Yeah, I mean, one, one approach to this, which is in the Who hiring method, is you ask people while you're going through that process of, who is your boss? Who is the hardest person you worked for? Who is someone, like, you didn't like working for? And then you, in the moment, say, how do you spell their name again? And like, you, you basically kind of quiz them to say, you know, I'm curious, um, if I reached out to that person What would, what would they give you constructive feedback on? And so, and, you know, sometimes I even fluff it, and I'm like, oh, I think I'm connected to this person, and I might, you know, might text him and call him. Because what you, you want to just, you want to get people off of their, their, whatever, their sales skill game, and get real, and challenge them on that. That's one way. Um, the other is, I think what we were talking about before I came in here was actually have people send materials of the work that they've done. So being able to see a deck that they built, an email that they sent.

AI assessment note: “one approach to this, which is in the Who hiring method, is you ask”

Q Now, I want to start with sales leadership skills and sales skills. A lot of people suggest that they are born. You're a natural sales person. Do you believe that sales skills are born or they can be learned?

A I fundamentally believe they can be learned. Uh, you know, I, I think a lot of people would say it's innate, you know, you, you're born with it, it's that your personality, someone that's outgoing, but my, my philosophy is that pretty much humans can learn anything if they're taught and they have the motivation to do it, and so I've seen in my career someone that's joined, you know, both Facebook and Slack that many people are like, oh, they're not outgoing, they don't have that gregarious nature, But they were able to navigate just, like, figuring out how to do sales because they had the work ethic, they had the desire to learn, and ultimately, it's about, it's about inputs, and it's not just about being a personable, like, gregarious person.

AI assessment note: “I fundamentally believe they can be learned.”

Q Do they have urgency when it comes to AI tools? Are they like, we need to get this in now? Or is it like part of the innovation budget of excitement?

A Absolutely. They need to get it now. And I think they need to get it now because The companies that are doing it right are actually going to be the innovators and, like, the accelerants in the space, and, and so what, what I think happens is, like, the herd mentality. Like, you've got a couple of these big, big brands and companies that are doing AI in the right way that's actually impacting their top line or bottom line already that isn't experimental, right, and they're willing to spend, some of those accounts are willing to spend five, 10, ten million dollars Annually on these type of initiatives. Because of that, what happens is board members, you know, other CEOs of other companies are like, we need to move quickly. We need to get an AI, we need to drive an AI initiative with inside our company.

AI assessment note: “Absolutely. They need to get it now.”

Q You mentioned your interview process with Glean. With the benefit of hindsight now, what could be done to have made that process better?

A I think that the, um, and this would be more feedback for Arvind, right, my CEO, on what he could have done better. I think that Arvind should have been challenging me to put together a point of view on a couple problems that I, like, I think senior leader interviews that CEOs are doing And, and, and this is another reason we do the panel the way we do. I'll explain in a second is interviews are very precious in terms of the time that your leadership team is spending on them, right? And so Arvind, he could have spent all this time with me and it not really lead to anything. I think that having him ask me, hey, AJ, here are the three problems that we're dealing with as a company right now. Can you produce something and present to me and my leadership team on how you're going to solve it? It has two benefits. Even if I don't turn out to be the right guy, it's giving him ideas. And that's what we, so that the other, one of the strategies we have in our panel interview is, I always ask my managers, it's a double, like, choose the account that this person is prepping for their sell to, On a new prospect that we are trying to get into. I hate wasted effort. It's money, I like to kill as many birds with one stone as I can.

AI assessment note: “Arvind should have been challenging me to put together a point of view”

Q yeah, it's super tough, and it actually just makes me think of why Mormons tend to actually be such good sellers, because they actually have to go and, you know, sell the Book of Mormon to, like, African But my question to you is, you see this, like, generation of new young reps coming in today. Are there commonalities in what you see them struggle to pick up slash learn?

A I would say AEs are really struggling as being super creative and flexible and nuanced when you're engaging in a live conversation with someone. So, everyone has an idea when they're going into a call of what to say. They first think they're gonna get rejected, then they find a way to, like, convince someone to be engaged in the conversation, and what happens is the customer is actually interested, or the prospect's interested, and people go into this very specific structured prescriptive approach, where I, I think that the best sellers navigate and adjust to the, to the, to the customer, the specific situation, and so I'd say that's where I see more junior sellers struggling the most, is they're not Actively listening and morphing and changing to the conversation.

AI assessment note: “AEs are really struggling as being super creative and flexible and nuanced”

Q I was wondering though, when it comes to this, it's one thing to get a deal done. It's another thing to get implementation done to get usage. We've seen Accenture and we've seen some big consulting firms Post some amazing numbers when it comes to AI services. To what extent are these large enterprises actually able to implement new AI technologies like Glean or like many other tools?

A This is where I would say the space is like falling down. And I'll, I'll speak to Glean separately, but just to, you know, for the audience, I think everyone is being sold A bag of goods and a dream of this sort of AI enabled workforce or Automation, top line, bottom line, and then when it comes to implementation, it's taking six, nine, 12 months, or it comes attached with a five million dollar services budget next to it, which is, it's like, well, hold on, I'm paying five million dollars to implement this thing for the, with one of the, you know, the big, the big companies, and, and then, and, like, I'm paying, like, the fees for the service, so I think what we're seeing is Even adoption and usage is not where it needs to be, and we're seeing that even with, you know, look at like Microsoft Copilot, I mean, Many customers are saying it's falling flat. Like, it's just not delivering the value that was advertised. So what the challenge is, is not like some of the other technologies, a product issue, it's more of a change management security challenge.

AI assessment note: “This is where I would say the space is like falling down.”

Q I'm a salesperson. I'm brilliant at packaging. Uh, how do you actually determine true grit quality in my sales skills when I answer your questions beautifully?

A Yeah, I mean, one, one approach to this, which is in the Who hiring method, is you ask people while you're going through that process of, who is your boss? Who is the hardest person you worked for? Who is someone, like, you didn't like working for? And then you, in the moment, say, how do you spell their name again? And like, you, you basically kind of quiz them to say, you know, I'm curious, um, if I reached out to that person What would, what would they give you constructive feedback on? And so, and, you know, sometimes I even fluff it, and I'm like, oh, I think I'm connected to this person, and I might, you know, might text him and call him. Because what you, you want to just, you want to get people off of their, their, whatever, their sales skill game, and get real, and challenge them on that. That's one way. Um, the other is, I think what we were talking about before I came in here was actually have people send materials of the work that they've done. So being able to see a deck that they built, an email that they sent.

AI assessment note: “get people off of their, their, whatever, their sales skill game, and get real”

Q Can I ask you, what's the most creative thing you've done to win a deal?

A With T-Mobile at, at Slack, um, there's a couple things. Like, one is I, I I knew that if I could, one of T-Mobile's key differentiators is, um, the team of teams, how they differentiate both with customer experience in the retail stores and online, and so what I did is went into a retail store, made, became friends with one of the retail people, recorded him on the technical challenges he was having, how he works, where he thought, like, Slack could play a role. Like, I went, I became friends with this guy. I did, like, We were texting, we were still texting. Did the same thing with a support agent where I just called in, pretend to be a T-Mobile customer, and like, just chatted up with a T-Mobile, uh, customer care. Like, get in the day of the life, and then the, the, the cherry on top was, I knew, I knew the CEO at the time, John Ledger, used to hang out at the W Bar in Seattle, and so, Before an on-site, that night before, I just stayed in that W bar, like, just hanging out, and John Ledger came in, and I went up to him, and we spent time chatting. And then the next day, I saw him in the lobby, I'm like, hey John. He's like, AJ, good to see you again. And that was like, as I was walking into a CIO meeting, and Cody Sanford at the time was like, how do you know John? Like, the CEO of our company.

AI assessment note: “went into a retail store, made, became friends with one of the retail people”

Q yeah, it's super tough, and it actually just makes me think of why Mormons tend to actually be such good sellers, because they actually have to go and, you know, sell the Book of Mormon to, like, African But my question to you is, you see this, like, generation of new young reps coming in today. Are there commonalities in what you see them struggle to pick up slash learn?

A I would say AEs are really struggling as being super creative and flexible and nuanced when you're engaging in a live conversation with someone. So, everyone has an idea when they're going into a call of what to say. They first think they're gonna get rejected, then they find a way to, like, convince someone to be engaged in the conversation, and what happens is the customer is actually interested, or the prospect's interested, and people go into this very specific structured prescriptive approach, where I, I think that the best sellers navigate and adjust to the, to the, to the customer, the specific situation, and so I'd say that's where I see more junior sellers struggling the most, is they're not Actively listening and morphing and changing to the conversation.

AI assessment note: “AEs are really struggling as being super creative and flexible and nuanced”

Q I was wondering though, when it comes to this, it's one thing to get a deal done. It's another thing to get implementation done to get usage. We've seen Accenture and we've seen some big consulting firms Post some amazing numbers when it comes to AI services. To what extent are these large enterprises actually able to implement new AI technologies like Glean or like many other tools?

A This is where I would say the space is like falling down. And I'll, I'll speak to Glean separately, but just to, you know, for the audience, I think everyone is being sold A bag of goods and a dream of this sort of AI enabled workforce or Automation, top line, bottom line, and then when it comes to implementation, it's taking six, nine, 12 months, or it comes attached with a five million dollar services budget next to it, which is, it's like, well, hold on, I'm paying five million dollars to implement this thing for the, with one of the, you know, the big, the big companies, and, and then, and, like, I'm paying, like, the fees for the service, so I think what we're seeing is Even adoption and usage is not where it needs to be, and we're seeing that even with, you know, look at like Microsoft Copilot, I mean, Many customers are saying it's falling flat. Like, it's just not delivering the value that was advertised. So what the challenge is, is not like some of the other technologies, a product issue, it's more of a change management security challenge.

AI assessment note: “This is where I would say the space is like falling down.”

Q Like it is the one area where I think most early stage founders get most wrong. You've hired exceptional sales teams. How do you run a process when adding to the sales team? What does that look like?

A Understand the deep history of the individual Over a chronological period of time. I didn't realize that that was a hiring methodology until Bob Fratty taught me that at Slack, which is kind of this who hiring, the who hiring method is what we call a chronological interview. Like, I ask people, what, what did you do in high school? Like, what were you proud of in high school? Not because, I don't care, and then I say, why did you go to the college you went to? What was your proudest accomplishment in college? And I do that through every Why did you leave the first job you did? Why did you go to the next job? And I go, really try to understand, because what you can build is an understanding of, like, the deep motivations that people have.

AI assessment note: “Understand the deep history of the individual Over a chronological period of time.”

Q Do they have urgency when it comes to AI tools? Are they like, we need to get this in now? Or is it like part of the innovation budget of excitement?

A Absolutely. They need to get it now. And I think they need to get it now because The companies that are doing it right are actually going to be the innovators and, like, the accelerants in the space, and, and so what, what I think happens is, like, the herd mentality. Like, you've got a couple of these big, big brands and companies that are doing AI in the right way that's actually impacting their top line or bottom line already that isn't experimental, right, and they're willing to spend, some of those accounts are willing to spend five, 10, ten million dollars Annually on these type of initiatives. Because of that, what happens is board members, you know, other CEOs of other companies are like, we need to move quickly. We need to get an AI, we need to drive an AI initiative with inside our company.

AI assessment note: “Absolutely. They need to get it now.”

Q What are the biggest commonalities in why they fail?

A Number one is, ah, this, the, the topic I, I, I wanna bring up is, like, a lack of two things. Creative problem solving and collaborative tension. And collaborative tension is a new word I coined at our big company kickoff called GKO. Um, the creative problem solving, it's, it's not just, you can very quickly know when you've got an AE that's, all they're doing is coming to you with problems and not coming with solutions and ideas. And that is a telltale sign that someone is not a creative problem solver. So like the best, the best employees Are the ones that when they meet with their boss or a stakeholder, they say, here's the problem. Here's what I've thought about for it. And here's one or two ideas I'm thinking about. What's your feedback? Whereas the AEs that fall into that bucket of like, that I'm like, damn, like, it's like, they are coming to you and they're saying, oh, like, I can't get my SE to do X, Y, and Z. I'm like, cut the bullshit. Like, What do you want them to do? Have you talked to them yet? Like, and you have to do this, like, annoying coaching to them, which is, which is something that at this point in the senior AE careers, like, you need to be going to try to solve that problem, or coming to me with how you're thinking about solving. The second one is the collaborative tension, um, just on why we get rid of people, is if you do not have the ability to Col…

AI assessment note: “a lack of two things. Creative problem solving and collaborative tension.”

Q Yeah, I do want to retain some sense of, you know, structure, otherwise my mind just goes everywhere. Slack was an incredible journey for you. Uh, it really shapes a lot of how one thinks when has, when one sees such a transformational journey. What are one or two of the biggest takeaways for you from Slack, and how did that impact how you think as a sales leader?

A The number one, number one takeaway that I, I've I've brought to Glean. It's what I give to other, you know, founders I advise and just is how important it is to have the collaboration and like collaborative tension between R&D and GTM. So when I was at Slack early days, it was interesting. Like I was struggling to get the organization to think about supporting the enterprise. We were so focused on just like the, like the inbound and the PLG. That we were starting to run into challenges with supporting and getting to customer success on the Comcast, the Walmarts that were some of those early, earlier enterprise customers, and so I think driving feedback to the product organization, challenging them, getting them on calls.

AI assessment note: “how important it is to have the collaboration and like collaborative tension between R&D and GTM”

Q What size contract does it make sense to have CS as a really built out function and really catered account?

A You've got to be looking at it a combo of the company size and the contract size. So I think one thing that I learned at Slack is like all Slack did was look at What the ARR was for the specific account, and then tied it, and they would only put a senior CSM on the, you know, whatever, the million dollar contracts. I think that can be a little bit of a miss because you're, if you are closing, let's say you close a couple hundred K deal with Exxon Mobil, and you're putting like a junior CSM on it who doesn't know how to navigate, you're gonna have, you're not gonna be likely to drive an upsell. And so what I look at is a combination of Employee count, and are, are they over a certain dollar amount?

AI assessment note: “a combo of the company size and the contract size.”

Q What are the biggest commonalities in why they fail?

A Number one is, ah, this, the, the topic I, I, I wanna bring up is, like, a lack of two things. Creative problem solving and collaborative tension. And collaborative tension is a new word I coined at our big company kickoff called GKO. Um, the creative problem solving, it's, it's not just, you can very quickly know when you've got an AE that's, all they're doing is coming to you with problems and not coming with solutions and ideas. And that is a telltale sign that someone is not a creative problem solver. So like the best, the best employees Are the ones that when they meet with their boss or a stakeholder, they say, here's the problem. Here's what I've thought about for it. And here's one or two ideas I'm thinking about. What's your feedback? Whereas the AEs that fall into that bucket of like, that I'm like, damn, like, it's like, they are coming to you and they're saying, oh, like, I can't get my SE to do X, Y, and Z. I'm like, cut the bullshit. Like, What do you want them to do? Have you talked to them yet? Like, and you have to do this, like, annoying coaching to them, which is, which is something that at this point in the senior AE careers, like, you need to be going to try to solve that problem, or coming to me with how you're thinking about solving. The second one is the collaborative tension, um, just on why we get rid of people, is if you do not have the ability to Col…

AI assessment note: “lack of two things. Creative problem solving and collaborative tension.”

Q What would you most like to change about the world of sales?

A Kind of what you said. Like, I, I want the world to see that this is a career path that enables you to become a CEO of another company. Meaning, like, I, like, career-wise, like, at some point I want to be a CEO of a company. Like, and I think I am uniquely positioned to do that because I am On one pillar of what makes companies great, which is go to market and sales. And so, I want that next grad that, regardless of whether you go to college or you're, you know, uh, at, at an Ivy League or at a state school, to realize that you can have a massive, like, career by investing in tech sales.

AI assessment note: “I want the world to see that this is a career path that enables you”

Q We've mentioned being in the experimental budget phase and we mentioned showing them the value that we can provide them. Bluntly, are there buzzwords? You're a very smart and attuned sales leader. Are there buzzwords where you see these boardrooms light up and go, oh, that's exciting, or buzzwords where they're, ah, that's cynical?

A I mean, the buzzword right now is generative AI. You know, just saying generative AI and how are you driving AI transformation inside your organization? How are you turning your employees into AI-centric employees. That, those are, like, buzzwords that get people leaning in. Ah, a lot of the large accounts that we're in, like, we're, we're kind of coming to the table saying, look, we have a differentiated solution, we have a unique value prop, but more importantly, like, we've got real, real customers that have gone through an AI journey. We can help you learn from those customers. So that's, like, leaning into Not, like, our speak of the, taking what our customers are saying. Like, even the example of, uh, the telecom I talked about, like, their CEO is talking about an AI enabled workforce. So we're taking that buzzword and bringing it to others.

AI assessment note: “the buzzword right now is generative AI... those are, like, buzzwords that get people leaning in”

Q What size contract does it make sense to have CS as a really built out function and really catered account?

A You've got to be looking at it a combo of the company size and the contract size. So I think one thing that I learned at Slack is like all Slack did was look at What the ARR was for the specific account, and then tied it, and they would only put a senior CSM on the, you know, whatever, the million dollar contracts. I think that can be a little bit of a miss because you're, if you are closing, let's say you close a couple hundred K deal with Exxon Mobil, and you're putting like a junior CSM on it who doesn't know how to navigate, you're gonna have, you're not gonna be likely to drive an upsell. And so what I look at is a combination of Employee count, and are, are they over a certain dollar amount?

AI assessment note: “You've got to be looking at it a combo of the company size and the contract size.”

Q Well, talk to me about that, because you, you sent me beforehand this incredible deck that you did on joining Glean. What deck do you ask people to send to you, and how does that look in structure?

A You know, other than, like, going deep into the why and the chronological side, we move from there to a panel interview, and that panel interview is, they get an hour, They get a, a prompt. That prompt is, tell us your history. Uh, tell us about, like, you know, your biggest career challenge. Talk about a, a large win that you have, and then walk through an example deal of selling, how you would, not sell glean, but how you would prep for, prep for, like, going after this account. You know, you just, you don't give them much guidance after that, and you see a wide range. You see people come in that have, like, Like no slides and are just like going and that's fine. I don't care about the slides or whether, whether they look beautiful. I want to understand the deep thought that you've done in preparation. And then in that moment, the thing that I do, and I'm, I'm going to, I'm going to say it now. I used to tell candidates like, please don't tell other candidates I'm going to do this, but I'm just going to do it because I think it's a good lesson that I'd love to just share with others. Um, and I learned this actually from Lexi Reese, who is my, one of, one of my bosses at, um, Facebook. So anyway, what I ask is, and I, I throw off the interview, mid-interview, and I say, hey, hey, like, let's pause here for a sec. If I give you, like, your book of business today, a hundred acco…

AI assessment note: “That prompt is, tell us your history. Uh, tell us about, like, your biggest career challenge.”

Q What does everyone think they know about selling AI tools that they get totally wrong?

A I think that, um, that it's gonna be Easy to implement is, is what they get wrong. And that's simply, I mean, we talked about it already. I think that lots of, lots of even our AEs that we have, like we are educating them, even though our product is relatively compared to the market, easy to implement. We're, we're, we're telling them set the right expectations, make sure that you have a deployment success plan. You know, I, I took a page out of Dave Schneider's book from ServiceNow and We're implementing a system where we're not paying AEs on their deals unless they have an approved deployment success plan filled out. I think one of the things that, you know, just looking at, you know, I don't know, talking to others, like I care very much about the customer success side. I own that function at Glean, so I own the pre-sales, post-sales, and that's a, for me, a very important part to it, but I think going back to your question, it's a lot of companies are Getting the big deals done, and then assuming, okay, we can figure out the deployments later, and that's what they get wrong.

AI assessment note: “that it's gonna be Easy to implement is, is what they get wrong.”

Q You call him up the night before, What do you advise them?

A Get your hands dirty on doing, doing, doing deals. Like the, the three things I would say to them are do the deals and learn it, and the reason I say that is like my framework for decision making on going to companies and for how I coach my AEs that like set up time with me is focus on the product. That's number one. Like learn the product, sell the product, figure it out. Number two, know the people. Get to know the people in your organization, figure out, like, how to build the relationships, and three is, like, learn the position that you have, and it's the three P's. It's kind of, like, how I have always kind of simplified both my career-making decision framework, focus on good products, good people, and a good position.

AI assessment note: “the three things I would say to them are do the deals and learn it”