The Exchanges

Q My question to you is, and it's a really hard one. Sales are not going well in my startup. They're not going well. We've missed numbers and the team feels it. What do I do then? Like, Do I get everyone excited, get everyone jacked up again, but they've been failing, like it is not okay. How do you respond to a team that's not hitting numbers?

A Yeah, I think it's more empowering. One, you've got to be honest about it. At a startup, you have to have revenue, right? You have a burn rate. That's not changing. So you've got to have revenue to offset that, or you're shortening the time horizon until your next fundraise. So I think you have to have an honest conversation about that. And then the sales team needs to To run a diagnostic, you have to get to root cause analysis. I would think that in general, coming out of that, you're going to uncover places in your sales process that are not well tuned that you can fix. And the sales team is also probably going to have legitimate feedback about where the product's not working. And then the CEO, it's up to you to determine whether or not you think that those product gaps are ones that belong in your roadmap. And if they do, then you've got to give the sales team a little bit of credit that maybe they're not winning because The product needs some things, or you got to say the things you're saying we need to win are outside of our product roadmap, in which case we have any, like a ICP problem of who we're actually targeting and talking to and how do you go fix that? Right? So I think what often doesn't happen when sort of the founder and the sales or don't operate effectively and ultimately fire your head of sales, right? Is did you get to a root cause analysis that you can agre…

AI assessment note: “One, you've got to be honest about it... you have to get to root cause analysis.”

Q If we go back to the actual process, we mentioned that some of the core characteristics we're looking for. How do I actually structure a hiring process? I've never hired, not a head of sales, but a sales rep before. Like, do I hire them in one meeting, two meetings, three? Like, how would you advise me to structure the actual hiring process?

A Yeah, well, first of all, let's hit on the word you're using, which is structure. So I think that's one of the mistakes that folks make is it should be a structured hiring process. You want to sit down and figure out what you think is going to need to be true about that individual and then design multiple interviews that test for those capabilities. When I was at Dialpad, one of the things we actually did was we brought folks in to the office. It's hard to do it in COVID, but like into the office for like a half day. And we actually just like let them, you know, sit beside our salespeople, stuck them on chat, saw, you know, if you dumped them in the deep end, could they actually sort of figure out how to respond to some of these things? And kind of gave them a hands-on experience with it, because we figured out that that was like a good way to separate who was like really a startup salesperson from somebody who was a salesperson who wanted to work at a startup. But, you know, that's one of the things we've also done at Stripe, right, is you have a homework assignment, something that's very reflective of what you're going to ask that person to do on day one when they show up. And it's a good way to test whether or not they're going to be capable of executing that thing, particularly because at the beginning, you're not going to get much more than a A phone and a computer, you kn…

AI assessment note: “design multiple interviews that test for those capabilities”

Q No, I totally get you. Ok, so that's one. We have that homework assignment. We come. I've blown you away. What next? I've impressed you with the first homework assignment slash case study. What happens in meeting number two? Do we have a friendly get to know you and talk about my ambitions? Like, how do we literally structure the next step?

A Got it, yeah. So before that homework assignment part, what we do are a set of screens. A lot of those are, you know, talking through your background, you kind of see what folks highlight, asking a core set of questions that get at someone's sales skills, and then you flip into this phase. So normally, with this homework assignment, for us, There's typically around four total interviews. So one is going to review this project, and then the other three are testing for alignment with our operating principles, and then sales skills. So from a sales skill perspective, you know, you would talk through the most complicated deal that they've worked on, or have them pitch you on their product and have a mock sales call around that, or talk through how you do pipeline management, talk through objection handling, your worst loss, You know, how you've gotten into an account that was totally cold, right? So those are a bunch of different things you might ask about. And then questions that are probably getting reused across the company that again are getting at values in how you solve problems and how you do the job. And those are typically behavioral where you'll talk about things that they've done in the past that and see if the way they went about solving that thing is how you would want that done at your company.

AI assessment note: “There's typically around four total interviews. So one is going to review this project”

Q Say we've done that, and now you've hired me. Yes, I'm joining Stripe as, you know, a new rep. Fantastic. Exciting. The hardest thing of all, I think that most startups mess up. Onboarding process. What does the best onboarding process for new reps look like, and how do you like to structure it?

A Yeah, this is something I was really impressed with at Stripe when I started. So for a company of the The scale we were at at that point, it was a full week of just spin up and you had sessions with John and Patrick where they were really, you know, spending time outlining the culture, outlining the company vision, which I felt like drove a lot of alignment out of the gates. And then, you know, day two, I think we would all get thrown into the support cues. And so that was really great at teaching our users first orientation and getting hands-on experience with customers and learning the product. So, you know, you would get a bunch of the questions that were coming inbound and a bunch of materials, and you'd have to just go and, you know, find the answer in them, which that's how it's going to be at a startup. You're not going to have a perfect playbook. And so you get the playbook that you have as it exists, and then you start to figure out, you know, how do you go answer things beyond that? But that is one of the things that when I came into Stripe, we didn't have from a sales perspective. You know, you basically still were in this super smart, kind of reactive, like Q&A for sales, and there wasn't a process. And so what I did for my first 30 days, I just went out, figured out, you know, where there were patterns and then started to put in what I thought was going to be our s…

AI assessment note: “it was a full week of just spin up and you had sessions with John”

Q So for me now joining Stripe in terms of like the onboarding process, Like, what does my first week look like? What does my first month look like? When do I speak to my first customers?

A Your first week at Stripe right now is very pan-stripe. So actually salespeople are with product people, with engineers, folks in recruiting, etc. And it's still similar to what I just described, where John and Patrick talk, and you basically get a broad lay of the land of the company strategy, all of our products, operating principles. And then the second week is when you flip over into sales, And this is where we go really deep on here are our customers. Here's how we segment. Here's our ideal customer profile. Let's actually start talking about the value proposition, our core messaging, objection handling. So you sort of get crash course on the Stripe sales process because I believe strongly you want to get folks in front of customers right away. A savvy salesperson can talk to somebody actually knowing very little about the product they're selling because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls pretty effectively and then just admit when they don't know the answer and go back and get it. So we're trying to get people in the deep end on calls right out of the gates. This is hard if you're super, super early from a sales perspective, but pair folks up obviously with more tenured reps do a lot of shadowing, or if you have solution architects, if you're selling a very tech…

AI assessment note: “Your first week at Stripe right now is very pan-stripe.”

Q So for me now joining Stripe in terms of like the onboarding process, Like, what does my first week look like? What does my first month look like? When do I speak to my first customers?

A Your first week at Stripe right now is very pan-stripe. So actually salespeople are with product people, with engineers, folks in recruiting, etc. And it's still similar to what I just described, where John and Patrick talk, and you basically get a broad lay of the land of the company strategy, all of our products, operating principles. And then the second week is when you flip over into sales, And this is where we go really deep on here are our customers. Here's how we segment. Here's our ideal customer profile. Let's actually start talking about the value proposition, our core messaging, objection handling. So you sort of get crash course on the Stripe sales process because I believe strongly you want to get folks in front of customers right away. A savvy salesperson can talk to somebody actually knowing very little about the product they're selling because what great salespeople do is ask good questions. And so if you can teach folks what questions to ask out of the gates, they actually can run calls pretty effectively and then just admit when they don't know the answer and go back and get it. So we're trying to get people in the deep end on calls right out of the gates. This is hard if you're super, super early from a sales perspective, but pair folks up obviously with more tenured reps do a lot of shadowing, or if you have solution architects, if you're selling a very tech…

AI assessment note: “Your first week at Stripe right now is very pan-stripe.”

Q If we go back to the actual process, we mentioned that some of the core characteristics we're looking for. How do I actually structure a hiring process? I've never hired, not a head of sales, but a sales rep before. Like, do I hire them in one meeting, two meetings, three? Like, how would you advise me to structure the actual hiring process?

A Yeah, well, first of all, let's hit on the word you're using, which is structure. So I think that's one of the mistakes that folks make is it should be a structured hiring process. You want to sit down and figure out what you think is going to need to be true about that individual and then design multiple interviews that test for those capabilities. When I was at Dialpad, one of the things we actually did was we brought folks in to the office. It's hard to do it in COVID, but like into the office for like a half day. And we actually just like let them, you know, sit beside our salespeople, stuck them on chat, saw, you know, if you dumped them in the deep end, could they actually sort of figure out how to respond to some of these things? And kind of gave them a hands-on experience with it, because we figured out that that was like a good way to separate who was like really a startup salesperson from somebody who was a salesperson who wanted to work at a startup. But, you know, that's one of the things we've also done at Stripe, right, is you have a homework assignment, something that's very reflective of what you're going to ask that person to do on day one when they show up. And it's a good way to test whether or not they're going to be capable of executing that thing, particularly because at the beginning, you're not going to get much more than a A phone and a computer, you kn…

AI assessment note: “design multiple interviews that test for those capabilities”

Q you think about, if we're not hiring that head of sales, we're bringing in reps. How do we make sure that we're not bringing, because I think often something I see also is they bring in one and they're just bad reps. And then they think of the problem with their model and it's just the rep. Should they bring in two or three? How should we think about that?

A Yeah, I agree. I think you want to have, you know, a handful. So again, you don't get the rep Problem. You're also at that point, I think trying to get to some level of pattern recognition, both on, are you honing in on an ideal customer profile? Are you seeing replicability anywhere? You know, it's hard to trust a single individual's point of view on what the pattern is. And so I do think you're going to want two to three folks to sort of corroborate that pattern as being, you know, true versus sort of a single individual's point of view, but two to three people versus going out and hiring 10, 20, you know, is obviously very different. And at that point, typically you'll have some other functions that are more operational at the company that you can kind of collapse everybody under until you get your formal head of sales.

AI assessment note: “I do think you're going to want two to three folks to sort of corroborate”

Q Say we've done that, and now you've hired me. Yes, I'm joining Stripe as, you know, a new rep. Fantastic. Exciting. The hardest thing of all, I think that most startups mess up. Onboarding process. What does the best onboarding process for new reps look like, and how do you like to structure it?

A Yeah, this is something I was really impressed with at Stripe when I started. So for a company of the The scale we were at at that point, it was a full week of just spin up and you had sessions with John and Patrick where they were really, you know, spending time outlining the culture, outlining the company vision, which I felt like drove a lot of alignment out of the gates. And then, you know, day two, I think we would all get thrown into the support cues. And so that was really great at teaching our users first orientation and getting hands-on experience with customers and learning the product. So, you know, you would get a bunch of the questions that were coming inbound and a bunch of materials, and you'd have to just go and, you know, find the answer in them, which that's how it's going to be at a startup. You're not going to have a perfect playbook. And so you get the playbook that you have as it exists, and then you start to figure out, you know, how do you go answer things beyond that? But that is one of the things that when I came into Stripe, we didn't have from a sales perspective. You know, you basically still were in this super smart, kind of reactive, like Q&A for sales, and there wasn't a process. And so what I did for my first 30 days, I just went out, figured out, you know, where there were patterns and then started to put in what I thought was going to be our s…

AI assessment note: “it was a full week of just spin up and you had sessions with John and Patrick”

Q So in terms of our ninety-day check-in, you're my boss, Jean. What do you expect me to have achieved in those first 90 days? What's the, oh, Harry's doing well. We're happy with how Harry's progressing. What are the signs?

A Number one, first and foremost, is are you mastering the product? And how to talk about it to a customer. So very enablement and learning oriented in the first 90 days. And so, and you get good feedback on this if you're doing a lot of ride-alongs, then, you know, their spin-up buddy can be pretty discerning of, is this person rapidly grokking the product, or am I constantly having to remind them of, here's how this actually works, or they're missing things. So a huge part is just, are you actually learning and incorporating what you need to know? But then beyond that, you know, sales ultimately is a match And so if you have that target, you can reverse engineer that right of in order to hit this number, you need to close this many deals of this size and take, you know, you win at this rate, it takes this amount of time. And so you actually can be able to tell your salesperson by nine days in, you know, I need you to have created and opportunities, you know, of this average size. And then we can ask ourselves whether or not you're there. If you are, Awesome. How do we accelerate that much more quickly? And if you're not, then, well, where within that funnel do you seem to be off? Are your deals too little? Do you not have enough? If you don't have enough, are you talking to enough people? Are you talking to the right people, right? And you can start to run a diagnostic.

AI assessment note: “Number one, first and foremost, is are you mastering the product?”

Q My question to you is, and it's a really hard one. Sales are not going well in my startup. They're not going well. We've missed numbers and the team feels it. What do I do then? Like, Do I get everyone excited, get everyone jacked up again, but they've been failing, like it is not okay. How do you respond to a team that's not hitting numbers?

A Yeah, I think it's more empowering. One, you've got to be honest about it. At a startup, you have to have revenue, right? You have a burn rate. That's not changing. So you've got to have revenue to offset that, or you're shortening the time horizon until your next fundraise. So I think you have to have an honest conversation about that. And then the sales team needs to To run a diagnostic, you have to get to root cause analysis. I would think that in general, coming out of that, you're going to uncover places in your sales process that are not well tuned that you can fix. And the sales team is also probably going to have legitimate feedback about where the product's not working. And then the CEO, it's up to you to determine whether or not you think that those product gaps are ones that belong in your roadmap. And if they do, then you've got to give the sales team a little bit of credit that maybe they're not winning because The product needs some things, or you got to say the things you're saying we need to win are outside of our product roadmap, in which case we have any, like a ICP problem of who we're actually targeting and talking to and how do you go fix that? Right? So I think what often doesn't happen when sort of the founder and the sales or don't operate effectively and ultimately fire your head of sales, right? Is did you get to a root cause analysis that you can agre…

AI assessment note: “One, you've got to be honest about it.”

Q you think about, if we're not hiring that head of sales, we're bringing in reps. How do we make sure that we're not bringing, because I think often something I see also is they bring in one and they're just bad reps. And then they think of the problem with their model and it's just the rep. Should they bring in two or three? How should we think about that?

A Yeah, I agree. I think you want to have, you know, a handful. So again, you don't get the rep Problem. You're also at that point, I think trying to get to some level of pattern recognition, both on, are you honing in on an ideal customer profile? Are you seeing replicability anywhere? You know, it's hard to trust a single individual's point of view on what the pattern is. And so I do think you're going to want two to three folks to sort of corroborate that pattern as being, you know, true versus sort of a single individual's point of view, but two to three people versus going out and hiring 10, 20, you know, is obviously very different. And at that point, typically you'll have some other functions that are more operational at the company that you can kind of collapse everybody under until you get your formal head of sales.

AI assessment note: “I do think you're going to want two to three folks to sort of corroborate”

Q There are a couple of things I have to unpack. You said kind of hit your number. Jean, I'm a startup founder for the first time. I don't know how to set quota. How do I set quota? Do I go really easy so they feel great and feel confident? Do I push it really hard so they're really ambitious? How should I set quota?

A Yeah, so the way we did this at Stripe, which I think worked well, was you want to build a sales org that If it does what it's supposed to do, you would obviously invest your next dollar in it. So we sat down with go to market with finance and designed our quotas to do exactly that. And then we had a ramp curve into them. So it gives folks breathing room to come up to speed to learn, but progress towards ultimately what productivity is going to need to look like. And then what we did at Stripe was also, we started with team-based quotas. You know, you're learning. We also started with lower leverage. So again, you're not, don't have as much at risk. And as we got better about understanding what was achievable, you know, where was something replicable, then we started increasing leverage, moving things more towards individual, you know, etc.

AI assessment note: “we sat down with go to market with finance and designed our quotas”

Q So in terms of our ninety-day check-in, you're my boss, Jean. What do you expect me to have achieved in those first 90 days? What's the, oh, Harry's doing well. We're happy with how Harry's progressing. What are the signs?

A Number one, first and foremost, is are you mastering the product? And how to talk about it to a customer. So very enablement and learning oriented in the first 90 days. And so, and you get good feedback on this if you're doing a lot of ride-alongs, then, you know, their spin-up buddy can be pretty discerning of, is this person rapidly grokking the product, or am I constantly having to remind them of, here's how this actually works, or they're missing things. So a huge part is just, are you actually learning and incorporating what you need to know? But then beyond that, you know, sales ultimately is a match And so if you have that target, you can reverse engineer that right of in order to hit this number, you need to close this many deals of this size and take, you know, you win at this rate, it takes this amount of time. And so you actually can be able to tell your salesperson by nine days in, you know, I need you to have created and opportunities, you know, of this average size. And then we can ask ourselves whether or not you're there. If you are, Awesome. How do we accelerate that much more quickly? And if you're not, then, well, where within that funnel do you seem to be off? Are your deals too little? Do you not have enough? If you don't have enough, are you talking to enough people? Are you talking to the right people, right? And you can start to run a diagnostic.

AI assessment note: “Number one, first and foremost, is are you mastering the product?”

Q Speaking of leveraging other people in the org, for me as the CEO, back to me as the CEO, and you as my advisor, what can I do to encourage sales to interact more efficiently with both customer success and product? How can I create these synergies where that may be traditionally more siloed?

A Yeah. I think one of the things we've done well at Stripe is getting product engaged, you know, from a sales perspective and having product on the front lines. One, it's a great way for them to get feedback. Two, great way to have, you know, empathy. And often you can produce like these perfect documents, great quantified data, and then you bring someone on a sales call and they get that aha moment. But you also want to use product efficiently. So I think You know, we're thoughtful around having some level of gating so that, you know, whether it's me or another leader is, is deciding when we're pulling product in. A lot of salespeople love having product on their call, right? Products should be pretty darn good at pitching as well. It has a stronger point of view often on the vision because it's in their head. But anyway, I typically am all for get product on calls. And then from a customer success perspective, you know, that's another key one where I think you want to have Really think about architecting the customer journey, and in particular, handoffs between organizations, and having a strong feedback loop around those handoffs, because often, you know, sales can do things that just really aren't setting customer success up for success. And so you want that feedback, because we can often change things that will make, you know, downstream lives easier. But then similarly, we…

AI assessment note: “getting product engaged, you know, from a sales perspective and having product on the front lines.”

Q Who's invited to loss reviews? Is it just sales teams? Is it Product. Is it customer success? How do you think about the right people to have in the room?

A Yeah, no, it ends up being all of them. So in the last reviews right now, actually, you know, we're now at a larger scale. And so we have one person team who helps us run this, but he'll prepare a bunch of content. And then you often find when you've reviewed the losses and you can put in Salesforce loss reasons, those types of things you wind up with like clear go to market challenges where our messaging, our strategies off, as you think about positioning yourself relative to Competition. We end up with like operational things where sort of roadblocks in your deal velocity actually wound up holding you back and killing the deal, and then you end up with product gaps. So we'll talk through all of those, and they influence product roadmap, and then obviously go to market changes as well.

AI assessment note: “Yeah, no, it ends up being all of them.”

Q Who's invited to loss reviews? Is it just sales teams? Is it Product. Is it customer success? How do you think about the right people to have in the room?

A Yeah, no, it ends up being all of them. So in the last reviews right now, actually, you know, we're now at a larger scale. And so we have one person team who helps us run this, but he'll prepare a bunch of content. And then you often find when you've reviewed the losses and you can put in Salesforce loss reasons, those types of things you wind up with like clear go to market challenges where our messaging, our strategies off, as you think about positioning yourself relative to Competition. We end up with like operational things where sort of roadblocks in your deal velocity actually wound up holding you back and killing the deal, and then you end up with product gaps. So we'll talk through all of those, and they influence product roadmap, and then obviously go to market changes as well.

AI assessment note: “Yeah, no, it ends up being all of them.”

Q No, I totally get you. Ok, so that's one. We have that homework assignment. We come. I've blown you away. What next? I've impressed you with the first homework assignment slash case study. What happens in meeting number two? Do we have a friendly get to know you and talk about my ambitions? Like, how do we literally structure the next step?

A Got it, yeah. So before that homework assignment part, what we do are a set of screens. A lot of those are, you know, talking through your background, you kind of see what folks highlight, asking a core set of questions that get at someone's sales skills, and then you flip into this phase. So normally, with this homework assignment, for us, There's typically around four total interviews. So one is going to review this project, and then the other three are testing for alignment with our operating principles, and then sales skills. So from a sales skill perspective, you know, you would talk through the most complicated deal that they've worked on, or have them pitch you on their product and have a mock sales call around that, or talk through how you do pipeline management, talk through objection handling, your worst loss, You know, how you've gotten into an account that was totally cold, right? So those are a bunch of different things you might ask about. And then questions that are probably getting reused across the company that again are getting at values in how you solve problems and how you do the job. And those are typically behavioral where you'll talk about things that they've done in the past that and see if the way they went about solving that thing is how you would want that done at your company.

AI assessment note: “There's typically around four total interviews. So one is going to review this project”

Q There are a couple of things I have to unpack. You said kind of hit your number. Jean, I'm a startup founder for the first time. I don't know how to set quota. How do I set quota? Do I go really easy so they feel great and feel confident? Do I push it really hard so they're really ambitious? How should I set quota?

A Yeah, so the way we did this at Stripe, which I think worked well, was you want to build a sales org that If it does what it's supposed to do, you would obviously invest your next dollar in it. So we sat down with go to market with finance and designed our quotas to do exactly that. And then we had a ramp curve into them. So it gives folks breathing room to come up to speed to learn, but progress towards ultimately what productivity is going to need to look like. And then what we did at Stripe was also, we started with team-based quotas. You know, you're learning. We also started with lower leverage. So again, you're not, don't have as much at risk. And as we got better about understanding what was achievable, you know, where was something replicable, then we started increasing leverage, moving things more towards individual, you know, etc.

AI assessment note: “we sat down with go to market with finance and designed our quotas”

Q Is it difficult in a very product-led growth motion in terms of sales feeling important enough? When product-led growth and product is so central that they're like, fuck, product makes up like 75% of revenue, and we're 25% with our traditional enterprise sales. We're not that important. Is it difficult to make them feel important in such a PLG motion?

A Yeah, so it's definitely, it's different, right, than a company that's like hardcore enterprise sales hooped to nuts. But I think what's important to remember is you put sales in place for a reason. And typically in that segment of the market, you do need sales. So at Stripe, as an example, product-led growth, sort of like the online self-search channel was awesome for, let's call it a series A, series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. People are not coming to the website and just signing up. They really need to talk to a human and go through a validation. And you can see when sales team in place, our deal sizes got a lot bigger and we started winning a different class of company than we had won before sales. And so I think it's just important to remember product-led growth can be awesome for a certain portion of the market. And if you can get to like very high revenue numbers on that portion, kudos to you because it's very efficient. But when it comes to pursuing larger accounts, multi-million dollar deals, It's pretty rare to do those without a human involved.

AI assessment note: “what's important to remember is you put sales in place for a reason”

Q So just so I understand this, so I do a homework assignment before the first meeting or in it with you?

A In it. So look, you've got to sell your startup first. So you've got to, you know, it's equal parts. The first one or two calls are going to be equal parts. You're interviewing them, but they're also interviewing you. Moving to a startup is a risk. So once you've gotten to the point where there's mutual interest on both sides is then when you get into the more It's a core part of the interview, and through that, well, a lot of it's behavioral, and, you know, they'll just answer questions through the interview process, but then part of it is we do give people, you know, two to three questions to prepare in advance, oftentimes with, like, hey, you get three slides, but you don't want to give people a homework assignment that's going to take them 24 hours to complete. They've got a day job, you know, but enough where you're putting a little sweat equity into proving that you really want this.

AI assessment note: “In it. So look, you've got to sell your startup first.”

Q Not at all, but I want to start with a little bit of an entry point. So how did you first make your way into the world of tech? And then how did you come to run some of the most powerful sales orgs today?

A So I started off looking up to my father. He worked in tech, so he spent 17 years at IBM, was one of the first people to sell a PC. He just had this really dynamic career. I think it's funny, like, what I remember most about it was he would go on all these business trips, and when he would come back after a week away, he'd bring you a little toy, which is very memorable as like a six-year-old. But it just made me want to have this international career when I grew up. And when I was looking closer to graduating from college, he and I had a conversation on the wine train in Napa. Trying to figure out what I was going to do. I wanted to come back to the Bay Area. I wanted to have a dynamic career, and he really got me to think about tech.

AI assessment note: “he really got me to think about tech.”

Q Speaking of leveraging other people in the org, for me as the CEO, back to me as the CEO, and you as my advisor, what can I do to encourage sales to interact more efficiently with both customer success and product? How can I create these synergies where that may be traditionally more siloed?

A Yeah. I think one of the things we've done well at Stripe is getting product engaged, you know, from a sales perspective and having product on the front lines. One, it's a great way for them to get feedback. Two, great way to have, you know, empathy. And often you can produce like these perfect documents, great quantified data, and then you bring someone on a sales call and they get that aha moment. But you also want to use product efficiently. So I think You know, we're thoughtful around having some level of gating so that, you know, whether it's me or another leader is, is deciding when we're pulling product in. A lot of salespeople love having product on their call, right? Products should be pretty darn good at pitching as well. It has a stronger point of view often on the vision because it's in their head. But anyway, I typically am all for get product on calls. And then from a customer success perspective, you know, that's another key one where I think you want to have Really think about architecting the customer journey, and in particular, handoffs between organizations, and having a strong feedback loop around those handoffs, because often, you know, sales can do things that just really aren't setting customer success up for success. And so you want that feedback, because we can often change things that will make, you know, downstream lives easier. But then similarly, we…

AI assessment note: “architecting the customer journey, and in particular, handoffs between organizations”

Q Not at all, but I want to start with a little bit of an entry point. So how did you first make your way into the world of tech? And then how did you come to run some of the most powerful sales orgs today?

A So I started off looking up to my father. He worked in tech, so he spent 17 years at IBM, was one of the first people to sell a PC. He just had this really dynamic career. I think it's funny, like, what I remember most about it was he would go on all these business trips, and when he would come back after a week away, he'd bring you a little toy, which is very memorable as like a six-year-old. But it just made me want to have this international career when I grew up. And when I was looking closer to graduating from college, he and I had a conversation on the wine train in Napa. Trying to figure out what I was going to do. I wanted to come back to the Bay Area. I wanted to have a dynamic career, and he really got me to think about tech.

AI assessment note: “he really got me to think about tech.”

Q Is it difficult in a very product-led growth motion in terms of sales feeling important enough? When product-led growth and product is so central that they're like, fuck, product makes up like 75% of revenue, and we're 25% with our traditional enterprise sales. We're not that important. Is it difficult to make them feel important in such a PLG motion?

A Yeah, so it's definitely, it's different, right, than a company that's like hardcore enterprise sales hooped to nuts. But I think what's important to remember is you put sales in place for a reason. And typically in that segment of the market, you do need sales. So at Stripe, as an example, product-led growth, sort of like the online self-search channel was awesome for, let's call it a series A, series B company. The minute you get past that, it doesn't work anymore. You're not like, if you build it, they will come. People are not coming to the website and just signing up. They really need to talk to a human and go through a validation. And you can see when sales team in place, our deal sizes got a lot bigger and we started winning a different class of company than we had won before sales. And so I think it's just important to remember product-led growth can be awesome for a certain portion of the market. And if you can get to like very high revenue numbers on that portion, kudos to you because it's very efficient. But when it comes to pursuing larger accounts, multi-million dollar deals, It's pretty rare to do those without a human involved.

AI assessment note: “when it comes to pursuing larger accounts, multi-million dollar deals, It's pretty rare”

Q So just so I understand this, so I do a homework assignment before the first meeting or in it with you?

A In it. So look, you've got to sell your startup first. So you've got to, you know, it's equal parts. The first one or two calls are going to be equal parts. You're interviewing them, but they're also interviewing you. Moving to a startup is a risk. So once you've gotten to the point where there's mutual interest on both sides is then when you get into the more It's a core part of the interview, and through that, well, a lot of it's behavioral, and, you know, they'll just answer questions through the interview process, but then part of it is we do give people, you know, two to three questions to prepare in advance, oftentimes with, like, hey, you get three slides, but you don't want to give people a homework assignment that's going to take them 24 hours to complete. They've got a day job, you know, but enough where you're putting a little sweat equity into proving that you really want this.

AI assessment note: “In it. So look, you've got to sell your startup first.”