The Exchanges

Q Do you agree with that when you hear that?

A Dave is talking there truthfully about like more probably corporate motivations. Um, and so, and those are important, but they're also abstracted away from the motivations of the people you're actually selling to. And so Both of those are important. The ones that are going to cause those magical moments, it depends on the person, but probably are more about personal motivations, right? Which is, holy shit, I'm not going to get my bonus unless I can show that we are compliant with SOC, you know, standards for security by December, right? And you should know that as a salesperson, you shouldn't, you should be Familiar enough. And this is another reason to get out of your office and get off zoom and go to the customer's building and hang out with them and spend time because 58 minute meeting on zoom where everybody else is paying attention. People are not sharing some things that maybe they're going to share when you're just hanging out, right? Having a beer at TGI Fridays after the meeting or at Starbucks or whatever it is. Like, that's why I say old school is, is the new school and it's the good school because the things that worked for the fuller brush salesman or IBM or Wang or, you know, uh, HP back in the day, it'll always work because humans don't change. And so the technology has changed. Uh, you have some PLG, you got zoom. Great. Use it, but don't use it at the expense o…

AI assessment note: “Dave is talking there truthfully about like more probably corporate motivations.”

Q How do you build a really, really good qualification machine?

A You gotta expect that bullshit is there. You have to realize that human nature is such that you want to have the rose-colored glasses on, you want to believe the deal is good, and you need to know that the opposite is probably true. And you've got to look for the dirt and you've got to build that into every time you're looking at a deal, you should be thinking about it. And now medic is a nice way to have a structure, a framework for this versus some meandering conversation that may or may not get to the answer, right? So your metrics, your economic buyer, decision process, decision criteria, identify pain, champion competition. That's the way I look at medic. And so in that way, I can have a conversation in possibly even 15 minutes, but max 30 minutes. And I'm going to be able to qualify this deal. We're going to be able to look for the, for the weaknesses and strengths. Yes.

AI assessment note: “medic is a nice way to have a structure, a framework for this”

Q Do you agree with that when you hear that?

A Dave is talking there truthfully about like more probably corporate motivations. Um, and so, and those are important, but they're also abstracted away from the motivations of the people you're actually selling to. And so Both of those are important. The ones that are going to cause those magical moments, it depends on the person, but probably are more about personal motivations, right? Which is, holy shit, I'm not going to get my bonus unless I can show that we are compliant with SOC, you know, standards for security by December, right? And you should know that as a salesperson, you shouldn't, you should be Familiar enough. And this is another reason to get out of your office and get off zoom and go to the customer's building and hang out with them and spend time because 58 minute meeting on zoom where everybody else is paying attention. People are not sharing some things that maybe they're going to share when you're just hanging out, right? Having a beer at TGI Fridays after the meeting or at Starbucks or whatever it is. Like, that's why I say old school is, is the new school and it's the good school because the things that worked for the fuller brush salesman or IBM or Wang or, you know, uh, HP back in the day, it'll always work because humans don't change. And so the technology has changed. Uh, you have some PLG, you got zoom. Great. Use it, but don't use it at the expense o…

AI assessment note: “Dave is talking there truthfully about like more probably corporate motivations... both of those are important”

Q to the statement that I'm often told, which is founders should be the one to create the sales playbook. And I'm thinking, gosh, I don't know many founders that could create that pithy qualification, 30 minute cool criteria as well as you just did there. I don't think many founders can create the sales demo templates for different verticals. Should the founder be the one to create the sales playbook?

A I've never seen it. Um, so to me with all these kind of, should this be the case? Should that be the case? Like, okay, like Sony might have an academic idea. Show me how it's actually been done. I would say at Datadog, Ahmet probably did it. He, I know he did, right? He did it before I got there, but it wasn't like what I just described. It was more like, um, they, there's some marketing that they see that talks about implementing the cloud. There's a link. You link to the demo, you put, you do the, you get online one week demo, you put your credit card in, somebody calls you to do the deal, and now you have Datadog, right? Something like that. And that's a great way to get started, but you're not going to scale to billions of dollars of revenue, at least in my, my experience with that. Like you're going to need more of what I just described and every place I've ever been, that's been the sales leader doing that.

AI assessment note: “I've never seen it... every place I've ever been, that's been the sales leader”

Q How do you build a really, really good qualification machine?

A You gotta expect that bullshit is there. You have to realize that human nature is such that you want to have the rose-colored glasses on, you want to believe the deal is good, and you need to know that the opposite is probably true. And you've got to look for the dirt and you've got to build that into every time you're looking at a deal, you should be thinking about it. And now medic is a nice way to have a structure, a framework for this versus some meandering conversation that may or may not get to the answer, right? So your metrics, your economic buyer, decision process, decision criteria, identify pain, champion competition. That's the way I look at medic. And so in that way, I can have a conversation in possibly even 15 minutes, but max 30 minutes. And I'm going to be able to qualify this deal. We're going to be able to look for the, for the weaknesses and strengths. Yes.

AI assessment note: “medic is a nice way to have a structure, a framework for this”

Q And like knowing when you have it, I'm getting into like a really cool problem for a lot of people, but I just want to first define what does the sales playbook mean to you?

A In an ideal world, I can take somebody from the outside, take them to new hire training, And like when we were doing new hire training, my last two companies, when I was running all that in the new hire training, we would get outbound meetings. Like your first days, we are cold calling. And I have it all documented that these are the personas. These are the challenges they have. This is some of the terminology you need. These are the things you can say. Here's how you handle objections. All that, right? So that's like front end of the playbook. Now, discovery call. Right format for discovery call. Questions to ask. How to manage it to be pithy and concise. 30 minutes. Are we barking up the right tree? Do they agree to that, to move towards our next steps of having a demo with the right people in the room? Right. Demo. So chronologically working through every step. And in the beginning, if you are a new CRO and you're like, oh, I don't know all this stuff. You can have a, it's a generally repeatable framework, right? Where you're going to say, I'm going to identify my ideal, uh, target customer ICP. People call it these days, my outbound calling, emailing, LinkedIn, GitHub, whatever. And now I'm going to discovery how I do that demo. How do we, what do we show in the demo? What, what are our desired outcomes? What are our exit criteria for each of those? Like if they say yes, We…

AI assessment note: “chronologically working through every step”

Q Did you find the money to exercise the options?

A So, um, while I was doing the data dog job in the beginning, my night job was making a market for, uh, Medallia shares. And so I found out that some deal had been done at like 16 bucks a share through the grapevine. And this is like, you know, this is the gray area because, um, you're, you know, there was no official secondary or anything like that. So I was able to find There's a company called, um, Forge, uh, which was a lifesaver. And through them, I found somebody who wanted to buy my shares. And I even had to stop some of the people who were disgruntled former employees from saying bad things about the company because they were driving the price down. And then I found another one just on my own, kept talking to every private equity, hedge fundy kind of person I could talk to. I found somebody and it was, it was, they were sketchy kind of like, Questionable deals that I was doing on my own, but I ended up doing them and I was able to do the second one through forge. So at least I had like a legit platform to work in and I was able to get enough to exercise. I had my spreadsheet to find that, uh, optimum point where I could sell the minimum amount of shares so I can hold on to as many as possible, but still come up with the amount of cash necessary to exercise all the other shares. And that's how money I sold. And I was able to do it. I had, I negotiated a two-year term to d…

AI assessment note: “I was able to get enough to exercise.”

Q What questions do you ask to qualify the deal? Are there some standard ones which will get you to a conclusion more substantively than others?

A Yeah. So, you know, the three whys in medic or why should they do anything? Why should it be data dog or whatever? And why should, why should it be now? Right. And so asking those questions, this is some basic stuff, but, and you know, that's the thing about sales is it's not quantum physics, but we talked about discipline before we talked about repeatability. And that's a big part of this is just always doing the right thing, even when there's so many excuses to not do it. And the same thing with asking the questions, same thing with medic, you know, what metrics do we have that, that build some kind of business case, even if it's a back of the napkin kind of thing, Like, why should they do it from a metrics perspective? Do we have any metrics from previous customers that we can use to tell a story there? Economic buyer. Do we know who the economic buyer is? What I know from experience is it's probably one or two levels above whatever you think it is, whoever you think it is. So when the salesperson is engaged in the deal, they're going to think that the person who's the technical user, that's probably their, they're thinking that's their champion. That person's boss, Who's really should be the target champion. That's who they think is the economic buyer, because it's just too hard to realize that the person who's going to sign is actually multiple levels above where you've ev…

AI assessment note: “the three whys in medic or why should they do anything?”

Q What are your biggest lessons on how to do a sales demo? Well, and where do most people fuck up?

A Make sure that You do the discovery ahead of time and you understand, understand their pains and, um, think about it in terms like put yourself in the shoes of the customer and it's not about features and it's not about show up and throw up. And you want to be able to say, Hey, Joe told me that he's trying to make decisions, um, but doesn't have the right information. And that led to application downtime. And so we're going to show you an example of how you can do that in your environment. And so here's, you, you told me you have, you know, a Unix machine. Here's the Unix machine. So they can start to see themselves. It's like telling a story. It's like, if you're reading, uh, I just, I started reading, uh, the great Gatsby. And so you're like, and by the way, what, I mean, holy cow, I've never written one sentence as good as the worst sentence in that book. But if you are going to identify with the protagonist in the story, Then, then the author has you. And it's the same thing with the demo. Like I need to see myself in this story and I can see how my life gets better. I can see how my, I get better at my job. I can see how I get home to my family earlier. I get promoted. I get kudos from my boss, things like that.

AI assessment note: “it's not about features and it's not about show up and throw up”

Q How does AI change the world of sales?

A I feel like it's almost like when the, when the Microsoft office suite came out, that's how old I am. I was like, oh my God, my spreadsheet pops right into my email and my word processing and it's all in the same. And all of a sudden I could do so many more emails and proposals so much more quickly as I see it right now. You can do better research on the companies. You can write a more compelling letter, you know, uh, prospecting email. You can, you can, uh, you know, put a proposal together faster. These things, it's gonna make you more efficient and effective, um, which I think so far are all good things. I know that people are working on other things to try to have the robots do all the selling. Let's see how that goes. You know, the thing about AI is they thought I listened to the AI guys. So the people who actually developed this stuff, right? They said, we thought it would automate the menial labor jobs, like whatever, or just like not, not to denigrate any jobs, but truck driving or being an analyst or something. And instead it's making amazing art. Like, so we don't know what it's going to do, but as of right now, I think you want to be able to use it to be better at your current tasks. That's what I see.

AI assessment note: “You can do better research on the companies. You can write a more compelling letter”

Q What questions do you ask to qualify the deal? Are there some standard ones which will get you to a conclusion more substantively than others?

A Yeah. So, you know, the three whys in medic or why should they do anything? Why should it be data dog or whatever? And why should, why should it be now? Right. And so asking those questions, this is some basic stuff, but, and you know, that's the thing about sales is it's not quantum physics, but we talked about discipline before we talked about repeatability. And that's a big part of this is just always doing the right thing, even when there's so many excuses to not do it. And the same thing with asking the questions, same thing with medic, you know, what metrics do we have that, that build some kind of business case, even if it's a back of the napkin kind of thing, Like, why should they do it from a metrics perspective? Do we have any metrics from previous customers that we can use to tell a story there? Economic buyer. Do we know who the economic buyer is? What I know from experience is it's probably one or two levels above whatever you think it is, whoever you think it is. So when the salesperson is engaged in the deal, they're going to think that the person who's the technical user, that's probably their, they're thinking that's their champion. That person's boss, Who's really should be the target champion. That's who they think is the economic buyer, because it's just too hard to realize that the person who's going to sign is actually multiple levels above where you've ev…

AI assessment note: “the three whys in medic or why should they do anything? Why should it be data dog”

Q What are your biggest lessons on how to do a sales demo? Well, and where do most people fuck up?

A Make sure that You do the discovery ahead of time and you understand, understand their pains and, um, think about it in terms like put yourself in the shoes of the customer and it's not about features and it's not about show up and throw up. And you want to be able to say, Hey, Joe told me that he's trying to make decisions, um, but doesn't have the right information. And that led to application downtime. And so we're going to show you an example of how you can do that in your environment. And so here's, you, you told me you have, you know, a Unix machine. Here's the Unix machine. So they can start to see themselves. It's like telling a story. It's like, if you're reading, uh, I just, I started reading, uh, the great Gatsby. And so you're like, and by the way, what, I mean, holy cow, I've never written one sentence as good as the worst sentence in that book. But if you are going to identify with the protagonist in the story, Then, then the author has you. And it's the same thing with the demo. Like I need to see myself in this story and I can see how my life gets better. I can see how my, I get better at my job. I can see how I get home to my family earlier. I get promoted. I get kudos from my boss, things like that.

AI assessment note: “Make sure that You do the discovery ahead of time and you understand their pains”

Q How do you make a great sales culture?

A I think you've got to have the vision. And the vision is that we will be great. That this is going to be What I said at, I put a mission statement up that I stole from one of my mentors at Medallia, and I used, I, I iterated a little bit at Datadog that we will be known, we, we will, we will have a legendary sales team that will be known for making great money, um, making life-changing money, uh, being best in class and, and, and having, and having fun. And, um, and that we will learn more, you will learn more And become better at your job during your time working on my team than you would have at any other team during that same amount of time. And you will make life changing money and you will never have to look for a job again because the halo of our success will be over your head for the rest of your career and people will seek you out. That was my first day. I said that to everybody on the team. And I also said that we will do a hundred and twenty million dollars next year. And we will do two 40 the year after that. And we will have the most successful IPO in history in New York. I also said that all in the first week or so. I got in trouble.

AI assessment note: “I think you've got to have the vision. And the vision is that we will”

Q How do you detect discipline in sales candidates you're interviewing?

A Fitness is one thing. It's not universal, but like I had one guy who was phenomenal, who was at Medallia, he's into video games and music, you know, and, and he's just, that's his world. And he is great at those things and he takes them seriously. Um, and you know, I just had, it's a little bit of a different model, right? Um, doing something hard and sticking with it. So the other thing is if you were at a startup, Anybody who's been at a pre IPO company, uh, that's done well for sure, but you're going to deal with some very hard times, like something, things are not going to go the way you thought. It's going to be harder than you expected. Did you stick? Are you one of these people who leaves every 18 months or are you there for the full four plus, right? If you've got a four year vesting cycle, Kind of like, to me, it's like, ah, getting your university degree. Did, did you stick out and stick it out and make it right?

AI assessment note: “doing something hard and sticking with it. So the other thing is if you were”

Q When it comes to hiring, I think most founders actually really fuck up sales hiring. When you think about lessons from hiring great sales reps, what are your biggest lessons that you know now about hiring reps that you wish you'd known when you started?

A When I started, It's, it was, it's almost like Moneyball. If you, um, if you ever saw that movie or read that book back in the day, they were picking baseball players because they had a good jawline. Cause the guy's wife was pretty like it's, it's, it's mind boggling, but that's how they were. Scouts were picking baseball players. There used to be some of that in sales. What I would say is they come in all shapes and sizes. Also, for each company, there's a little bit different. Like, at, at, ah, at, at Medallia, we needed somebody who could show up and have A meeting with a C-suite exec. Um, and, uh, and at, and, and didn't need to get into technical details because it was not a technical sale. It was a, Hey, we envision a world where customer companies are loved by their customers and employees. You know, that's a, my, my mom can get behind that at data dog, super technical sale. So I wanted, I would ask people I wanted to make sure they could handle the subject matter. So one, so one thing I might ask is, I generally ask this all the time anyway. So I'm gonna, I'm gonna go backwards and I want to know your life journey. I want to know your life trajectory. Where'd you grow up? What'd your parents do? What were you into in high school? What's the highest level math you ever took? You know, I'm just getting, I'm getting a read because for example, In the US, if you are reasona…

AI assessment note: “What I would say is they come in all shapes and sizes.”

Q How do you make a great sales culture?

A I think you've got to have the vision. And the vision is that we will be great. That this is going to be What I said at, I put a mission statement up that I stole from one of my mentors at Medallia, and I used, I, I iterated a little bit at Datadog that we will be known, we, we will, we will have a legendary sales team that will be known for making great money, um, making life-changing money, uh, being best in class and, and, and having, and having fun. And, um, and that we will learn more, you will learn more And become better at your job during your time working on my team than you would have at any other team during that same amount of time. And you will make life changing money and you will never have to look for a job again because the halo of our success will be over your head for the rest of your career and people will seek you out. That was my first day. I said that to everybody on the team. And I also said that we will do a hundred and twenty million dollars next year. And we will do two 40 the year after that. And we will have the most successful IPO in history in New York. I also said that all in the first week or so. I got in trouble.

AI assessment note: “I think you've got to have the vision.”

Q to the statement that I'm often told, which is founders should be the one to create the sales playbook. And I'm thinking, gosh, I don't know many founders that could create that pithy qualification, 30 minute cool criteria as well as you just did there. I don't think many founders can create the sales demo templates for different verticals. Should the founder be the one to create the sales playbook?

A I've never seen it. Um, so to me with all these kind of, should this be the case? Should that be the case? Like, okay, like Sony might have an academic idea. Show me how it's actually been done. I would say at Datadog, Ahmet probably did it. He, I know he did, right? He did it before I got there, but it wasn't like what I just described. It was more like, um, they, there's some marketing that they see that talks about implementing the cloud. There's a link. You link to the demo, you put, you do the, you get online one week demo, you put your credit card in, somebody calls you to do the deal, and now you have Datadog, right? Something like that. And that's a great way to get started, but you're not going to scale to billions of dollars of revenue, at least in my, my experience with that. Like you're going to need more of what I just described and every place I've ever been, that's been the sales leader doing that.

AI assessment note: “every place I've ever been, that's been the sales leader doing that.”

Q How do you detect discipline in sales candidates you're interviewing?

A Fitness is one thing. It's not universal, but like I had one guy who was phenomenal, who was at Medallia, he's into video games and music, you know, and, and he's just, that's his world. And he is great at those things and he takes them seriously. Um, and you know, I just had, it's a little bit of a different model, right? Um, doing something hard and sticking with it. So the other thing is if you were at a startup, Anybody who's been at a pre IPO company, uh, that's done well for sure, but you're going to deal with some very hard times, like something, things are not going to go the way you thought. It's going to be harder than you expected. Did you stick? Are you one of these people who leaves every 18 months or are you there for the full four plus, right? If you've got a four year vesting cycle, Kind of like, to me, it's like, ah, getting your university degree. Did, did you stick out and stick it out and make it right?

AI assessment note: “doing something hard and sticking with it”

Q Should AEs do their own outbound or should we fully give to SDRs?

A Asking somebody else, so I call it pipeline generation PG. Asking somebody else to do PG for you is like asking them to go to the gym for you. Um, I think it creates, I don't, I don't think it creates the right culture to think that this is something that can be outsourced. Um, and so the way I look at it is PG is everybody's job. Um, and so whether you're a sales leader, a SDR, we're all constantly trying to get, we are in the deal creation business. And when I say, I said to you and I sent you an email, uh, That sales leaders should run to the front of the sales process, and I can guarantee almost, I, I think every time, every time I've talked to a company, For the first time, I don't want to lead the witness. So I don't want to say, Hey, what do you, you know, are you focused on pipeline generation? Cause their answer will be yes, of course more. I'm going to say, Hey, what would you do this week? Where, what meetings did you go on? What'd you do on Monday, Tuesday, Wednesday? What, what meetings with companies were staged in the, in the sales process? I can start to see, are they out in the field? Are they, and most, most of them, if they are doing any customer meetings, Are in closing mode. They're trying to be the closer. And if you don't have enough pipeline and you have a really high close rate, you're not going to hit your number. But if you have a ton of pipeline, and…

AI assessment note: “Asking somebody else to do PG for you is like asking them to go”

Q And I, I read that and I was like, great, but when should you layer on the world-class sales org to the PLG and how do you advise founders on that?

A Maybe one way to answer it and I'll answer it on other ways as well is as the founder, If there's that voice in your head or that feeling in your stomach where you're like, hmm, I wish I had a better salesperson right now. I wish, I wish I could break into the enterprise. I wish I could go up market. I wish I could do three year contracts instead of month to month. I wish I could do bigger deals. I wish I could sell multiple products instead of one product. Whatever it is, that voice went off in your head. Like it's, it's probably time and it probably was time before that because the other thing I was thinking about, like if you're running a race, like you're, you're a runner. And so if you're running a marathon and you don't hydrate until you are thirsty, it is too late because you are dehydrated and it's going to take a long time for yourselves to be able to get that water. And by that time might be too late. So, um, I think a general feeling or a general ethos that Yes, the product and the product like growth motion is super important. Of course it is. Excuse me. And I'm going to also build another channel of revenue generation through excellent sales, just like I have excellent product. Like when I went to Datadog, people didn't want to go there. Like recruiting was so hard. Um, and part of it was a reputation that it was a, it was an engineering company. They didn't respec…

AI assessment note: “it's probably time and it probably was time before that”

Q When it comes to hiring, I think most founders actually really fuck up sales hiring. When you think about lessons from hiring great sales reps, what are your biggest lessons that you know now about hiring reps that you wish you'd known when you started?

A When I started, It's, it was, it's almost like Moneyball. If you, um, if you ever saw that movie or read that book back in the day, they were picking baseball players because they had a good jawline. Cause the guy's wife was pretty like it's, it's, it's mind boggling, but that's how they were. Scouts were picking baseball players. There used to be some of that in sales. What I would say is they come in all shapes and sizes. Also, for each company, there's a little bit different. Like, at, at, ah, at, at Medallia, we needed somebody who could show up and have A meeting with a C-suite exec. Um, and, uh, and at, and, and didn't need to get into technical details because it was not a technical sale. It was a, Hey, we envision a world where customer companies are loved by their customers and employees. You know, that's a, my, my mom can get behind that at data dog, super technical sale. So I wanted, I would ask people I wanted to make sure they could handle the subject matter. So one, so one thing I might ask is, I generally ask this all the time anyway. So I'm gonna, I'm gonna go backwards and I want to know your life journey. I want to know your life trajectory. Where'd you grow up? What'd your parents do? What were you into in high school? What's the highest level math you ever took? You know, I'm just getting, I'm getting a read because for example, In the US, if you are reasona…

AI assessment note: “they come in all shapes and sizes. Also, for each company, there's a little bit different.”

Q That was very, very kind of you, but I just spoke to Carlos at Harness beforehand, and he said that I had to start with the mechanical engineering part. He said, why did you make the move from engineering to sales?

A Well, I ended up doing mechanical engineering, just engineering in general, because I didn't have a lot of money growing up. I read a magazine in 1987 called US News and World Report. The five or seven top earning degrees all were engineering, and I was like, I don't know any engineers. I was living, I grew up in New York City, and my dad was a cop. We were living in the country at the time, very rural place. And so, uh, I seemed pretty good at math and science and I got into it. I love technology. I always admired Steve jobs and Bill Gates and those guys were kind of heroes from my childhood. And I got a, uh, a design job in Detroit using CAD cam software. And so I got pretty good at it. I wanted to go work for the company and it was turned out to be this company, parametric technology corporation or PTC. I went there for the technology. Not realizing that they kind of possibly are the greatest sales team that's ever been put together. So this qualification methodology medic that everybody uses, it was invented there while I was there. Company was doing about two hundred million a year, so they still had the DNA of a startup. And so I talked with them about just how they built an amazing qualification machine, a pipeline generation machine, sales process machine. And I just happened into that as an engineer.

AI assessment note: “I went there for the technology... And I just happened into that as an engineer.”

Q How does AI change the world of sales?

A I feel like it's almost like when the, when the Microsoft office suite came out, that's how old I am. I was like, oh my God, my spreadsheet pops right into my email and my word processing and it's all in the same. And all of a sudden I could do so many more emails and proposals so much more quickly as I see it right now. You can do better research on the companies. You can write a more compelling letter, you know, uh, prospecting email. You can, you can, uh, you know, put a proposal together faster. These things, it's gonna make you more efficient and effective, um, which I think so far are all good things. I know that people are working on other things to try to have the robots do all the selling. Let's see how that goes. You know, the thing about AI is they thought I listened to the AI guys. So the people who actually developed this stuff, right? They said, we thought it would automate the menial labor jobs, like whatever, or just like not, not to denigrate any jobs, but truck driving or being an analyst or something. And instead it's making amazing art. Like, so we don't know what it's going to do, but as of right now, I think you want to be able to use it to be better at your current tasks. That's what I see.

AI assessment note: “it's gonna make you more efficient and effective”

Q You said about holding people accountable to numbers. Um, a lot of people are missing their numbers right now, Dan, and it's hard. Um, how do you advise leaders and sales leaders to keep morale up when sales teams are getting battered?

A They should be in it with the people, uh, especially when times are hard, like as a leader, when times are hard, you got to bring them up. And when times are good, you got to bring them down. We got to keep them steady. Don't get too high on yourself when things are good and don't feel too bad when things are going tough because that'll affect your performance. And so You should get in it with them and see what is the problem. Do we have a product problem, a market problem? Do we have a regional problem or is it a person problem? Right? And if you've gone through all of that and you're just like, I don't, I don't know the answer yet, but I do know it's not a person problem. I think there's, there's like probably a whole set of things to do. First of all, being, being with them and understanding where the pain is, because sometimes it could be the deals are coming, but they're not coming soon enough. So if you have some financial pressure, there's some, some things that you can do to be able to alleviate some of that financial pressure temporarily.

AI assessment note: “They should be in it with the people, uh, especially when times are hard”

Q Can I be blunt, Dan? You came from very humble beginnings. You mentioned your father there and kind of growing up in the countryside earlier. How is money what you thought it would be?

A Even though I had, I was part of four IPOs, the last two, which were the life changing ones, you kind of like, you have like car changing, kitchen changing, house changing, right? And then there's life changing. And it took me both Both Medallion and Datadog happened in 2019. And then you got a six month lockup. And then I was an executive officer at Datadog. So that was on a automated selling, right? Like you can't just say, I want to sell like, you know, all this stock, you know, because then it gets published and like, what's going on? There's a problem. So you just, you create a spreadsheet and the bankers just automatically sell. So I didn't have all of it until like 2021. And so, at that point, I was 50 years old. Not only was my dad a cop, but for a lot of their, my time, they were, my, both my parents were unemployed. You know, I had a lot of debt. I never, like, I had enough time Where I was, I, I, every time I use my credit card now, I still expect it to, to be declined every time because I just had such a long period of time where I defaulted on my credit cards and everything. And it took me until I was 50 years old to make that money. Thank God, because I was fully formed, I would say, and I could see how making a ton of money can distort reality for people. Um, so from that From that, on that dimension.

AI assessment note: “I could see how making a ton of money can distort reality for people.”

Q in a world of kind of try before you buy and more individual advocates, what started small can become very big as you saw with Capital One, but it's very easy to do what you said, which is 600 bucks. Ah, who cares? And so how do you think about not diminishing importance from accounts because of their small entry point and giving justified weight on what they can be?

A Oh man, such a good question. That's why you're so good at this. So, um, and we got a relaxed vibe going. So, people wearing hats, sitting on couches. So, when we started the enterprise at Datadog in early 2017, as I mentioned, there were no big deals to be had. We were, we were, we were lucky That we were able to pull off that Capital One deal, a little bit, a little bit of great execution and a little bit of luck. And, um, but there were not, those deals were not, were not around at other companies because Capital One was such a leader going to the cloud. So I had to convince the enterprise people. It was, this is like with Olivier. It was like, as long as it's a real project, solving a real problem, we kind of don't care how small the deal is. Our hypothesis was that this cloud thing was going to take off, and when it takes off, whoever is in the stack is just going to scale with their applications. And so, which is kind of like, to me, what I saw with Snowflake, and you know, but this is, this is real time, so we didn't see this yet. This is 2017. So our, our idea was just get in there. And be part of it. And if it was like a, generally speaking, probably minimum for the enterprise is 10,000 dollars, um, ARR. Right. Um, and cause then you got enough servers to, there's some heft to it. It's a real project and it happened all the time, but in the beginning it was a leap of f…

AI assessment note: “as long as it's a real project, solving a real problem, we kind of don't care”

Q Did you find the money to exercise the options?

A So, um, while I was doing the data dog job in the beginning, my night job was making a market for, uh, Medallia shares. And so I found out that some deal had been done at like 16 bucks a share through the grapevine. And this is like, you know, this is the gray area because, um, you're, you know, there was no official secondary or anything like that. So I was able to find There's a company called, um, Forge, uh, which was a lifesaver. And through them, I found somebody who wanted to buy my shares. And I even had to stop some of the people who were disgruntled former employees from saying bad things about the company because they were driving the price down. And then I found another one just on my own, kept talking to every private equity, hedge fundy kind of person I could talk to. I found somebody and it was, it was, they were sketchy kind of like, Questionable deals that I was doing on my own, but I ended up doing them and I was able to do the second one through forge. So at least I had like a legit platform to work in and I was able to get enough to exercise. I had my spreadsheet to find that, uh, optimum point where I could sell the minimum amount of shares so I can hold on to as many as possible, but still come up with the amount of cash necessary to exercise all the other shares. And that's how money I sold. And I was able to do it. I had, I negotiated a two-year term to d…

AI assessment note: “I was able to get enough to exercise.”

Q Can I be blunt, Dan? You came from very humble beginnings. You mentioned your father there and kind of growing up in the countryside earlier. How is money what you thought it would be?

A Even though I had, I was part of four IPOs, the last two, which were the life changing ones, you kind of like, you have like car changing, kitchen changing, house changing, right? And then there's life changing. And it took me both Both Medallion and Datadog happened in 2019. And then you got a six month lockup. And then I was an executive officer at Datadog. So that was on a automated selling, right? Like you can't just say, I want to sell like, you know, all this stock, you know, because then it gets published and like, what's going on? There's a problem. So you just, you create a spreadsheet and the bankers just automatically sell. So I didn't have all of it until like 2021. And so, at that point, I was 50 years old. Not only was my dad a cop, but for a lot of their, my time, they were, my, both my parents were unemployed. You know, I had a lot of debt. I never, like, I had enough time Where I was, I, I, every time I use my credit card now, I still expect it to, to be declined every time because I just had such a long period of time where I defaulted on my credit cards and everything. And it took me until I was 50 years old to make that money. Thank God, because I was fully formed, I would say, and I could see how making a ton of money can distort reality for people. Um, so from that From that, on that dimension.

AI assessment note: “I could see how making a ton of money can distort reality for people.”

Q How do we build a relationship with that buyer who's multiple levels up from the technical user without being patronizing to that technical user?

A Well, in an ideal world, you're going to earn your way up, right? And so there's two different ways. And so the fact that I was at Medallia and Datadog back to back are two extremes. So at Datadog, we started with Hands on keyboards, the practitioner, the person who's actually implementing the cloud. It was crazy, man, because everything that we were told, everything that I was ever taught, and I taught, like start, come in high, get to power early. The reality is, so at Datadog, Amit, you've had Amit Agarwal on, right? Amit and I went on a series of dinners with Shardul Shah in early 2017, and we were, and it was all CIOs. And CTOs. And we were so excited and we went to fancy restaurants and nobody cared about cloud monitoring. Nobody, everybody had just done big deals with AppDynamics and Splunk and Dynatrace and New Relic and they, and they said, we already have the cloud handled. We just did a deal with AWS. So they didn't want to talk to us at all. And I couldn't get them interested. Amit couldn't get him interested. Sheryl couldn't get him interested. That's a lot of firepower. So it's almost like the nature of the, the, the, the market cycle was such that we had to focus on the people who were actually tasked with implementing the cloud successfully. And so we were selling to the people who were implementing and the fact that Datadog actually worked, they could, they cou…

AI assessment note: “Well, in an ideal world, you're going to earn your way up, right?”

Q in a world of kind of try before you buy and more individual advocates, what started small can become very big as you saw with Capital One, but it's very easy to do what you said, which is 600 bucks. Ah, who cares? And so how do you think about not diminishing importance from accounts because of their small entry point and giving justified weight on what they can be?

A Oh man, such a good question. That's why you're so good at this. So, um, and we got a relaxed vibe going. So, people wearing hats, sitting on couches. So, when we started the enterprise at Datadog in early 2017, as I mentioned, there were no big deals to be had. We were, we were, we were lucky That we were able to pull off that Capital One deal, a little bit, a little bit of great execution and a little bit of luck. And, um, but there were not, those deals were not, were not around at other companies because Capital One was such a leader going to the cloud. So I had to convince the enterprise people. It was, this is like with Olivier. It was like, as long as it's a real project, solving a real problem, we kind of don't care how small the deal is. Our hypothesis was that this cloud thing was going to take off, and when it takes off, whoever is in the stack is just going to scale with their applications. And so, which is kind of like, to me, what I saw with Snowflake, and you know, but this is, this is real time, so we didn't see this yet. This is 2017. So our, our idea was just get in there. And be part of it. And if it was like a, generally speaking, probably minimum for the enterprise is 10,000 dollars, um, ARR. Right. Um, and cause then you got enough servers to, there's some heft to it. It's a real project and it happened all the time, but in the beginning it was a leap of f…

AI assessment note: “as long as it's a real project, solving a real problem, we kind of don't care”