The Exchanges

Q the sales leader perspective. How can we make sure we have sales performance? Uh, if we're an AE, you said before, there are things that AEs can do to ensure that they hit or exceed quota. What do you think that they can do? And if you were an AE in today's market, what do you advise them in terms of what they can do to hit and exceed quota?

A I mean, I think nothing's a given. Um, but I think people are still running their businesses. They're still operating. It's an opportunity to get creative, to pivot your messaging. From, to efficiency, to cost savings, to operational efficiencies, all of these things. And I think I've watched the team get really creative. We've got two folks down at a customer onsite right now, running a hackathon with the team. They're retool sponsoring a hackathon and they're building applications together. And so they're meeting all these new teams. They're embedding themselves in the business. They're building great relationships. Um, and I think hopefully they'll find some cool opportunities. Uh, we've got folks running webinars themselves. With customers they work with and targeting very specific verticals, which I think has been really cool to watch. We've got folks creating their own customer dinners and traveling to create new interest. Like the team is getting really creative. Um, and I think that that's what this type of economy will drive is really honestly inspiring creativity from the team.

AI assessment note: “pivot your messaging... running a hackathon... running webinars... creating their own customer dinners”

Q But, but, like, when you think about that time with them, are there one or two takeaways that you've really taken away from them and from Segment that stay with you today?

A Three. There's three that I would say I've learned. I, the, the amount I learned, like, the compression of what I learned at Segment by just being around such incredible people, I feel incredibly lucky, uh, to have had that opportunity and to have learned from everyone I was able to learn from, but I think the biggest would be keep the talent bar as high as possible for as long as possible. Do not Ever build a process or a structure or a team or anything until you know what problem you're trying to solve. That's become a very core thing that we have a lot of Eleanor isms and one is whenever someone comes to me with something, I'll say, what's the problem we're trying to solve. I think it's so easy and hyper growth to just build, build, build, build, build, copy and paste your old playbook, build, build, build, build, build, build. And you have to, there's such pressure to move quickly, but if you know what problem you're solving, you can't go wrong and you can at least always stand behind that decision later. Um, And I think the third is that selling into a new category is really challenging. It's a different type of challenge retools, a new category segment was a new category. You're not just selling a point solution. You're not just selling a product. You have to create budgets. You have to create, it's like, you're not selling the technology. You're selling a behavior change…

AI assessment note: “Three. There's three that I would say I've learned.”

Q So help me out here. Um, I'm a founder, uh, and you're an angel in my company, and you're gonna help me today. Um, do I create the sales playbook? Do I hire a team to create the sales playbook? And what is a sales playbook?

A So I think the role of the founder at the beginning in terms of the sales perspective, that's not their job, I believe, to create the sales playbook, but it is their job to generate the inputs That go into that playbook. And I think the playbook could be sort of two different things. It could be, how do you do deals like your deal playbook? What does that look like? What's your sales process? But then in a much more macro level, I think it very much is also what's your hiring profile. What's your org design? What's your customer life cycle? What's your tech stack? All of these things. But I think when you go back to the beginning and what do you founders need to focus on the founder's job is to talk to as many prospects. And customers as possible. They need to be focused on finding product market fit. They need to get just incredibly close to the problem that you're solving. They need to learn how customers want to buy their product because that's step zero of building a sales playbook. Do they want to sign up with a credit card? Do they want a POC? Do seven people need to be involved? There's only one person need to be involved. How senior does that person need to be? These are the inputs that a sales hire for sales hire will need to build the playbook. But I don't think a founder necessarily needs to do that, but they do need to generate the inputs.

AI assessment note: “that's not their job, I believe, to create the sales playbook”

Q senior versus junior. A lot of people say it depends on actually your motion, whether you're PLG or whether you're enterprise, and they, they kind of always are quite binary when I speak to them, which is like, you have to be one or the other. Do you agree that you have to be product-led or like enterprise top-down traditional sales, or can you be both at the same time?

A I do think it's a little bit of a false dichotomy. Um, I think, especially in the early stages, I think there are some, and again, I think this is also what founders should realize in their first through. It's all about how your customer wants to buy and what does that look like at that stage? Do they want to read docs and sign up with a credit card? Do they need to bring in other people? Can they buy it themselves? What's their level of seniority? What does the sales process look like? How long did it take? Were they immediately able to go get budget? Did they have to go above? Did you have to go above? Did you have to run a full blown trial or did they just want to try it out for a little bit? These are the types of things that I think are what's so important and why finder founder led sales in the beginning is so important because it's going to teach you what type of model you're in. I also do think you can have both a segment was both, uh, while I was there, retool is both right now. We have a PLG motion and we also have an enterprise motion. I think that works from zero to a hundred million roughly. And I think once you hit around a hundred million, You need to start to pick a lane a little bit more because by that stage, your buyer has likely changed. Your sales process has likely changed. If you're a category creator, your market's maturity has likely changed. Your produ…

AI assessment note: “I do think it's a little bit of a false dichotomy.”

Q but like you said there, like, you know, don't just copy stripe, you know, always know the why. When it comes to pricing, I'm always like, oh, fuck it. Don't bother to reinvent the wheel. If it works for other people, just do it. Like if it's a similar lab model, do you agree with that when it comes to pricing or do you actually think I'm being too flippant?

A No, I think it's pattern recognition is so important and people are used to, they buy seats from Salesforce. They pay, well, it depends on product of Stripe. They pay consumption pricing with Twilio. They, you know, there are no models going out and creating a new pricing model is why, like, do not reinvent the wheel when it comes to pricing. However, I think it is important to know what your value metric is and to always start with. How do customers get value out of my product? What is that metric? How can I get as close to that metric as possible? Because you need the price to value to be there. When you buy more Stripe and you spend more money, you get more revenue. Like there is extremely tight price to value alignment. And so what's the way to get that tightest price to value alignment where with their spending more, you're increasing the value that you're delivering.

AI assessment note: “do not reinvent the wheel when it comes to pricing. However, I think it is important”

Q Do you not expect some within 30 to 60 days? I want to be seeing customer calls going forward to next stage. I want to be seeing conversations progressing. We can push this.

A Yeah. I would say an empty calendar is a red flag to your point. They're not outbounding. They're not booking any meetings. They're not meeting with their SDR. They're not meeting with their sales engineer. They're not meeting with their CSMs. So I think an empty calendar would be a huge one. Um, and two, uh, I think if someone's really ramping and going all in, they are asking me so many questions. Like if they're not peppering you with questions, if they're not peppering their onboarding buddy with questions, if they're not posting in channels, then like, Hey, I was reading this. I was listening to this call. Could someone walk me through this? Then I know they're not actually trying to deeply engage with the material and internalize it. And that to me is a huge red flag. So yeah, an empty calendar and no questions.

AI assessment note: “I would say an empty calendar is a red flag to your point.”

Q flexibility that street fighters have. Wonderful terminology. Great title for the show, by the way. Um, but, uh, I, I want to ask, if we think about the process, I've never hired sales teams before, Elna, in this hypothetical founder situation. So when it comes to the process, How do I structure the process? Like, can you walk me through how you do yours, and how I should do mine?

A So again, I think that it always comes back to what's important to you at that stage. What are you hiring for at that stage? And I think so many of my sales cycles that I'm in are, are you going to build something, or are you going to buy something? I think it's the same with hiring. When it comes to your candidates, what do you want to build, and what do you want to buy? And so I always think about, here's what I can build. I can teach this Sales process. I can teach how to use the product. I can teach how the technical aspects. I can't teach IQ. I can't teach EQ. I can't teach character. I can't teach drive and I can't think teach curiosity and I can't teach the ability to deliver pricing without fainting, you know, or something like that. Like what's the, what are the things that I cannot teach that I must buy and are critically important to me? And those five are mine. So design interviews that test for those things, like what are your important, how do you test for those? Where are you getting the signal? I also want to test for technical comfort. So what's an interview to make sure they're just not going to be intimidated by a technical product or selling to engineers. I want to test for past performance. Have they been successful? Um, and then I build the interview process from there, but it starts with what am I buying?

AI assessment note: “design interviews that test for those things... I build the interview process from there”

Q senior versus junior. A lot of people say it depends on actually your motion, whether you're PLG or whether you're enterprise, and they, they kind of always are quite binary when I speak to them, which is like, you have to be one or the other. Do you agree that you have to be product-led or like enterprise top-down traditional sales, or can you be both at the same time?

A I do think it's a little bit of a false dichotomy. Um, I think, especially in the early stages, I think there are some, and again, I think this is also what founders should realize in their first through. It's all about how your customer wants to buy and what does that look like at that stage? Do they want to read docs and sign up with a credit card? Do they need to bring in other people? Can they buy it themselves? What's their level of seniority? What does the sales process look like? How long did it take? Were they immediately able to go get budget? Did they have to go above? Did you have to go above? Did you have to run a full blown trial or did they just want to try it out for a little bit? These are the types of things that I think are what's so important and why finder founder led sales in the beginning is so important because it's going to teach you what type of model you're in. I also do think you can have both a segment was both, uh, while I was there, retool is both right now. We have a PLG motion and we also have an enterprise motion. I think that works from zero to a hundred million roughly. And I think once you hit around a hundred million, You need to start to pick a lane a little bit more because by that stage, your buyer has likely changed. Your sales process has likely changed. If you're a category creator, your market's maturity has likely changed. Your produ…

AI assessment note: “I do think it's a little bit of a false dichotomy.”

Q but like you said there, like, you know, don't just copy stripe, you know, always know the why. When it comes to pricing, I'm always like, oh, fuck it. Don't bother to reinvent the wheel. If it works for other people, just do it. Like if it's a similar lab model, do you agree with that when it comes to pricing or do you actually think I'm being too flippant?

A No, I think it's pattern recognition is so important and people are used to, they buy seats from Salesforce. They pay, well, it depends on product of Stripe. They pay consumption pricing with Twilio. They, you know, there are no models going out and creating a new pricing model is why, like, do not reinvent the wheel when it comes to pricing. However, I think it is important to know what your value metric is and to always start with. How do customers get value out of my product? What is that metric? How can I get as close to that metric as possible? Because you need the price to value to be there. When you buy more Stripe and you spend more money, you get more revenue. Like there is extremely tight price to value alignment. And so what's the way to get that tightest price to value alignment where with their spending more, you're increasing the value that you're delivering.

AI assessment note: “do not reinvent the wheel when it comes to pricing”

Q Can I, speaking of the market there, and how you mentioned it's changed a little bit in the last few months, how do you think about the market mattering when it comes to hiring the best talent, and does what people want in a role change according to market, really presumably salary versus equity?

A I have noticed a shift. I think people are It's funny. I think when things were so insane towards the end of 20, 21, people were looking for the next moon shot. Like they wanted the big valuation. They wanted the equity. They would take early bets more. Uh, and then people are trying to de-risk their choices. Now is this company spending responsibly? Have they made smart financial investment investments or reps hitting their numbers? People have been challenging me on that way more than they used to. What does rep success look like? Where is it? Where are the deals coming from? What is lead flow like? And so I think now folks are optimizing for cash a little bit more than equity. Still both though. Um, but they're more focused on de-risking versus finding the moonshot.

AI assessment note: “folks are optimizing for cash a little bit more than equity”

Q the sales leader perspective. How can we make sure we have sales performance? Uh, if we're an AE, you said before, there are things that AEs can do to ensure that they hit or exceed quota. What do you think that they can do? And if you were an AE in today's market, what do you advise them in terms of what they can do to hit and exceed quota?

A I mean, I think nothing's a given. Um, but I think people are still running their businesses. They're still operating. It's an opportunity to get creative, to pivot your messaging. From, to efficiency, to cost savings, to operational efficiencies, all of these things. And I think I've watched the team get really creative. We've got two folks down at a customer onsite right now, running a hackathon with the team. They're retool sponsoring a hackathon and they're building applications together. And so they're meeting all these new teams. They're embedding themselves in the business. They're building great relationships. Um, and I think hopefully they'll find some cool opportunities. Uh, we've got folks running webinars themselves. With customers they work with and targeting very specific verticals, which I think has been really cool to watch. We've got folks creating their own customer dinners and traveling to create new interest. Like the team is getting really creative. Um, and I think that that's what this type of economy will drive is really honestly inspiring creativity from the team.

AI assessment note: “It's an opportunity to get creative, to pivot your messaging.”

Q But, but, like, when you think about that time with them, are there one or two takeaways that you've really taken away from them and from Segment that stay with you today?

A Three. There's three that I would say I've learned. I, the, the amount I learned, like, the compression of what I learned at Segment by just being around such incredible people, I feel incredibly lucky, uh, to have had that opportunity and to have learned from everyone I was able to learn from, but I think the biggest would be keep the talent bar as high as possible for as long as possible. Do not Ever build a process or a structure or a team or anything until you know what problem you're trying to solve. That's become a very core thing that we have a lot of Eleanor isms and one is whenever someone comes to me with something, I'll say, what's the problem we're trying to solve. I think it's so easy and hyper growth to just build, build, build, build, build, copy and paste your old playbook, build, build, build, build, build, build. And you have to, there's such pressure to move quickly, but if you know what problem you're solving, you can't go wrong and you can at least always stand behind that decision later. Um, And I think the third is that selling into a new category is really challenging. It's a different type of challenge retools, a new category segment was a new category. You're not just selling a point solution. You're not just selling a product. You have to create budgets. You have to create, it's like, you're not selling the technology. You're selling a behavior change…

AI assessment note: “Three. There's three that I would say I've learned.”

Q So I do want to touch on that because Jordan told me I had to, uh, and never argue with Jordan. He said, given your roots there in customer success, like, how do you think that was an advantage for you today as a sales leader, having had that as your start and how did that impact your mindset as a sales leader?

A Yeah, me, I think it's a massive advantage. I think I've, I've now looking back, I've led customer success teams, pre and post sales engineering operations teams. Renewals teams, expansion sales teams, new business sales teams, and I think, actually, I think one way to put it, I have a customer from Clever, my first company, who I used to call, and they would say, we never have any idea what your role is, we just know we have to do what you tell us to, um, and like, would that all calls went that way, uh, but I think it speaks to, it has made me, I don't see myself now as a sales team builder, even though I've, I've sort of Moved into specializing in sales. Um, I see myself as a company builder. It's why I like early stage startups. It's why I like to always see the complete picture and always ground every decision I make in what is the complete customer life cycle? What's going to need to happen three months, six months from now? What are we going to run into? What are the challenges we're going to face? I think it's, it's helped me see around corners a little bit in a way that you can't, if you haven't been exposed to as many different types of conversations. I mean, I've been in Hundreds of QBRs, of renewals calls, of churns, save calls, of discovery calls, and POC scoping calls, like the, the pattern recognition you can build by just having been present in so many conversat…

AI assessment note: “I don't see myself now as a sales team builder... I see myself as a company builder.”

Q Got you. And that's the final step. Okay. What, what makes the best, the best in those cases?

A Then, so to your point, or what Jordan said earlier about how do you sell a product with no buyer or no use case? We test for that in the interview process. How do you sell a product with no buyer or no use case? Uh, so it's to me, the biggest signal on dot connecting. Can they take an abstract product and tell a compelling story? So can they pick a company Can they understand the company and their business model well enough to know what problems exist? Can they tap connect the dots between rituals functionality with the problems that company has? And can they turn that into an interesting narrative that would be compelling for a buyer?

AI assessment note: “to me, the biggest signal on dot connecting. Can they take an abstract product”

Q So I do want to touch on that because Jordan told me I had to, uh, and never argue with Jordan. He said, given your roots there in customer success, like, how do you think that was an advantage for you today as a sales leader, having had that as your start and how did that impact your mindset as a sales leader?

A Yeah, me, I think it's a massive advantage. I think I've, I've now looking back, I've led customer success teams, pre and post sales engineering operations teams. Renewals teams, expansion sales teams, new business sales teams, and I think, actually, I think one way to put it, I have a customer from Clever, my first company, who I used to call, and they would say, we never have any idea what your role is, we just know we have to do what you tell us to, um, and like, would that all calls went that way, uh, but I think it speaks to, it has made me, I don't see myself now as a sales team builder, even though I've, I've sort of Moved into specializing in sales. Um, I see myself as a company builder. It's why I like early stage startups. It's why I like to always see the complete picture and always ground every decision I make in what is the complete customer life cycle? What's going to need to happen three months, six months from now? What are we going to run into? What are the challenges we're going to face? I think it's, it's helped me see around corners a little bit in a way that you can't, if you haven't been exposed to as many different types of conversations. I mean, I've been in Hundreds of QBRs, of renewals calls, of churns, save calls, of discovery calls, and POC scoping calls, like the, the pattern recognition you can build by just having been present in so many conversat…

AI assessment note: “I think it's a massive advantage... it has made me... see myself as a company builder”

Q Can I, speaking of the market there, and how you mentioned it's changed a little bit in the last few months, how do you think about the market mattering when it comes to hiring the best talent, and does what people want in a role change according to market, really presumably salary versus equity?

A I have noticed a shift. I think people are It's funny. I think when things were so insane towards the end of 20, 21, people were looking for the next moon shot. Like they wanted the big valuation. They wanted the equity. They would take early bets more. Uh, and then people are trying to de-risk their choices. Now is this company spending responsibly? Have they made smart financial investment investments or reps hitting their numbers? People have been challenging me on that way more than they used to. What does rep success look like? Where is it? Where are the deals coming from? What is lead flow like? And so I think now folks are optimizing for cash a little bit more than equity. Still both though. Um, but they're more focused on de-risking versus finding the moonshot.

AI assessment note: “I think now folks are optimizing for cash a little bit more than equity.”

Q Eleanor, I am a moron, ok? I need help more than this. We're going to break down one by one. Technical aptitude, like, how do you test this? Is it like screen share demo? And I'll, how, let's dive into that. How do you test for technical?

A Uh, I like them to explain, we, we have one of our sales engineers interview, and we, they explain it's on, walk us through the previous last product you've sold. Walk us through the tech. And so then we can test how deep did they get in their previous product, and did they understand it? And then we'll ask a few questions about retool. We're not even looking for, for future candidates out there. Um, we're looking for less. Can you answer them more? How do you handle yourself when you're asked questions you don't know the answer to? Do you try to make something up or do you just say great question? I'm not sure I'll have to bring in someone else.

AI assessment note: “we have one of our sales engineers interview, and we, they explain”

Q Got you. And that's the final step. Okay. What, what makes the best, the best in those cases?

A Then, so to your point, or what Jordan said earlier about how do you sell a product with no buyer or no use case? We test for that in the interview process. How do you sell a product with no buyer or no use case? Uh, so it's to me, the biggest signal on dot connecting. Can they take an abstract product and tell a compelling story? So can they pick a company Can they understand the company and their business model well enough to know what problems exist? Can they tap connect the dots between rituals functionality with the problems that company has? And can they turn that into an interesting narrative that would be compelling for a buyer?

AI assessment note: “to me, the biggest signal on dot connecting. Can they take an abstract product”

Q What incredible energy he has, I have to admit, but I want to start a little bit on you. So tell me, how did you make your way into the world of tech, and how did you come to be a sales leader, obviously today at Retool?

A Uh, I frequently use my own narrative as an example for folks on why careers are such a general gem versus a ladder, but I actually lived in New York before, which is where I live now, um, and I worked for the New York City Department of Education on a middle school literacy program. I was in schools, Once a week working on rolling out software to ensure sixth graders or grade six are graduating reading on grade level. Um, and as part of that, we purchased as a school district, a lot of literacy software, and I was very focused on rolling that out. I ran into a ton of infrastructure challenges. I wasn't able to connect the software to the underlying data systems and students move in and out of classrooms in New York city, more than one million times a day. And so the data became obsolete. Almost immediately. And I bought really expensive software and the kids couldn't use it because they couldn't log in because we didn't know what school they were in, who their teacher was, what classes they were in. And then we weren't able to securely send that to the software providers. So I taught myself how to write scripts to try and improve this process. I think I violated quite a few student privacy laws, uh, with the very casual way in which I was shipping off student data to third parties, which in hindsight makes me feel incredibly uncomfortable. Um, But I was looking, uh, one day fo…

AI assessment note: “I worked for the New York City Department of Education on a middle school literacy program.”

Q Do you not expect some within 30 to 60 days? I want to be seeing customer calls going forward to next stage. I want to be seeing conversations progressing. We can push this.

A Yeah. I would say an empty calendar is a red flag to your point. They're not outbounding. They're not booking any meetings. They're not meeting with their SDR. They're not meeting with their sales engineer. They're not meeting with their CSMs. So I think an empty calendar would be a huge one. Um, and two, uh, I think if someone's really ramping and going all in, they are asking me so many questions. Like if they're not peppering you with questions, if they're not peppering their onboarding buddy with questions, if they're not posting in channels, then like, Hey, I was reading this. I was listening to this call. Could someone walk me through this? Then I know they're not actually trying to deeply engage with the material and internalize it. And that to me is a huge red flag. So yeah, an empty calendar and no questions.

AI assessment note: “Yeah. I would say an empty calendar is a red flag to your point.”

Q teams wanting enterprises, the additional layer, and the poor sales reps go, the customers are telling me about the product messaging on our website, and they're concerned about it being for startups, and I'm having to sell this kind of different product. How do you think about the challenge of serving two masters too soon, and when the right time is to kind of layer on that new customer persona?

A I mean, I think it's hard, but I think it's fun. And I think it's why salespeople still get to have a job and add a lot of value to the process. Like that's the part we're figuring out. We, so I always want to make sure we have enterprise logos on our website so that we can point to, yes, it's all of the above. And I'll frequently say the way that pricing and packaging is structured as it lends itself to that. So I'll say, yeah, we have these self-service options on our website. They're for folks at smaller companies, they're for startups, they're for you to get started, they're for you to trial, they're for you to have an easy way to get started with the product. But when you're buying and investing in a product like Retool or X or Y or Z, a platform, it's a behavior change and it requires multiple stakeholders. It requires a full blown evaluation. It requires having multiple use cases in order to get started. And it requires creating space in your budget and your team and your process to bring a new platform in. And that requires a more thorough evaluation. And that's why we have done with customers like X, Y, and Z. Um, so to me, that's the fun part is the deal situational awareness. It requires like our reps have to always think what type of deal am I in? Am I in an enterprise deal? Am I in a PLG deal? Do I need to just get out of the way? Do I need to zoom out and run a ni…

AI assessment note: “our reps have to always think what type of deal am I in?”

Q Given your experience, and then we'll move on to actually building the team, what's your biggest advice to founders when it comes to blending together product-led growth and a traditional sales lab model?

A Uh, just take the time, always asking yourself what you're learning and what you're trying to learn. Like, it shouldn't just be, just know the why behind everything you're doing. It, you know, it shouldn't just be, uh, Well, Stripe was really successful. So we're going to do what Stripe did. You know, it should be, why was Stripe successful? What can we take away from that? Okay. What is our product? What's the hypothesis that we're testing? You should just. It's a risk because you create complexity when you create both and you have to do it for a reason. So you, it comes back to what's the problem you're trying to solve. What's the hypothesis you're testing. Don't go out and just hire 10 or 15 reps. Hire one, hire two. How are they successful? What are they doing? Are we ready? What's the right profile? Great. Let's hire two more, three more. Great. Are they successful? What's the profile? Okay, good. Now we feel we've validated this hypothesis. Let's hire more, but to be Cyclical and test hypothesis as part of it before you just create a lot of complexity that you have to unwind later.

AI assessment note: “It's a risk because you create complexity when you create both and you have to do it for a reason.”

Q Totally get you. Cause we mentioned like the talent changes there in terms of what they want from the roles. When we think about like actually once onboarding the quotas that they're going against, that must change too. In terms of like, how does quota setting and target setting for you as a leader change in cold versus hot markets?

A I mean, you don't get to decide what the market is, unfortunately. So I think all you can do is always look at the most recent set of data. You have to look at the company goals and where are you trying to go? And then you reconcile the two. So what are you seeing? What is top of funnel? What is past performance look like? What is average deal size? What is average sales cycle? What kind of pipeline coverage do you need to hit the target every month, every quarter, every year? And how can you take that and map it into a comp plan where, you know, hopefully I think the, the, the logic I've always used is that you should design a comp structure where at least 80% of your reps are hitting. Um, and that's sort of where the bell curve is.

AI assessment note: “all you can do is always look at the most recent set of data.”

Q How do you feel about discounting to get deals done?

A I don't know, not like team no discount. There's a time and a place. Um, but I think discounting is Sort of a false hearing. It's just, do you understand the value you're providing? Do you understand how important that is to them and what problems you're solving? Do you understand their alternative to using your product? And do you have a compelling ROI case? And then if you have all of those things and you have them with the right people and you're negotiating with someone who can say yes, sometimes people have a tendency to negotiate with people who can only say no, if you're negotiating to someone to say yes, and you believe it's a fair exchange of value. And if it's a discount that gets you there, great.

AI assessment note: “There's a time and a place... if it's a discount that gets you there, great.”

Q Given your experience, and then we'll move on to actually building the team, what's your biggest advice to founders when it comes to blending together product-led growth and a traditional sales lab model?

A Uh, just take the time, always asking yourself what you're learning and what you're trying to learn. Like, it shouldn't just be, just know the why behind everything you're doing. It, you know, it shouldn't just be, uh, Well, Stripe was really successful. So we're going to do what Stripe did. You know, it should be, why was Stripe successful? What can we take away from that? Okay. What is our product? What's the hypothesis that we're testing? You should just. It's a risk because you create complexity when you create both and you have to do it for a reason. So you, it comes back to what's the problem you're trying to solve. What's the hypothesis you're testing. Don't go out and just hire 10 or 15 reps. Hire one, hire two. How are they successful? What are they doing? Are we ready? What's the right profile? Great. Let's hire two more, three more. Great. Are they successful? What's the profile? Okay, good. Now we feel we've validated this hypothesis. Let's hire more, but to be Cyclical and test hypothesis as part of it before you just create a lot of complexity that you have to unwind later.

AI assessment note: “Don't go out and just hire 10 or 15 reps. Hire one, hire two.”

Q What are signs that you're ready for sales enablement?

A I mean, I always think people hire rev ops too late and sales enablement too late, um, because you can't hire it once you need it. You got to hire it before you need it. So maybe hire it when you've onboarded your first few reps and you realized you're starting to figure out what works, but you as the sales leader is, are wearing too many hats and you want to go focus on something else, then Bring in sales enablement then. Um, I think it's a tough role to hire for too, but, um, I think you hire before you need it. When you're feeling like onboarding is going really well and you're patting yourself on the back, it's probably time to hire sales enablement.

AI assessment note: “hire it when you've onboarded your first few reps and you realized you're starting”

Q What are signs that you're ready for sales enablement?

A I mean, I always think people hire rev ops too late and sales enablement too late, um, because you can't hire it once you need it. You got to hire it before you need it. So maybe hire it when you've onboarded your first few reps and you realized you're starting to figure out what works, but you as the sales leader is, are wearing too many hats and you want to go focus on something else, then Bring in sales enablement then. Um, I think it's a tough role to hire for too, but, um, I think you hire before you need it. When you're feeling like onboarding is going really well and you're patting yourself on the back, it's probably time to hire sales enablement.

AI assessment note: “hire it when you've onboarded your first few reps and you realized you're starting”

Q We've been in the mindset here that we're just buyers in this talent market. Sadly, that's not the case. When you think about closing candidates, have there been patterns between the hardest and the easiest candidates to close?

A Yeah. I mean, I think it's, it's looked really different over the last few months. Like it's definitely shifted and you can feel it. Um, in terms of the hardest candidates to close, ones who came just from a company that just had a big exit where the really good early talent is starting to look, those are people, those are profiles people really like to go after us. So those are really tough to close. They have a lot of options. They've had a lot of success. They know what they're looking for. Uh, they know the hallmarks of a company that will be successful, so they push you really hard. Um, those folks can be really hard to close.

AI assessment note: “In terms of the hardest candidates to close, ones who came just from a company”

Q What is the tipping point for you need to hire your first sales hire? And how do you think about advising me on whether that's a senior leader who builds a team beneath them, or whether it's junior AEs who we send out into the field and just go hunt quota?

A I mean, I think it is a little more arts than science. And I think a lot of it depends on what you expect out of that person. If we're going to someone hired, hire someone junior, don't expect them to build the end to end thing of the entire hiring profile, this tech stack, get the leaders in place, be one of sales enablement, all of that. So I think a lot of it comes down to what are the founders expectations? I mean, everything comes down to expectations, but what are the founders expectations of what that role or do? But I think, so you can hire someone at any point. It just matters on what to expect from them. But I think you don't hire someone until you have found thought about this a lot in advising, but you found some form of product market fit. You can retain the customers, your clothes, you close. You have some notion of how your customers want to buy your product. You've generated some form of reliable inbound. I think back to the expectations piece. I think sometimes there's an expectation that you hire a salesperson and then boom, there's a revenue. But really sales is there to accelerate a healthy machine, but it can't fix a broken one.

AI assessment note: “you don't hire someone until you have... found some form of product market fit.”

Q What do you think is the hardest thing for you in terms of scaling into a sales leader?

A It's a lot of work. Um, it's really, it's just a lot of work at a hyper growth company. I just took a week and a half off and came back and worked three, 15 hour days back to back. Um, and then I decided I needed another vacation. Uh, I think it's just hard. And I think a lot of people don't want to say that it's hard or, Say that it's a lot of work. I think it's really fun. I think it's an intellectual challenge. I think it's extremely rewarding and I think it's a lot of work and it's really hard. There's a thousand things that are immediate. And I think it's that classic urgent versus important. And how do you prioritize what's important and how do you make sure you get done? What is urgent?

AI assessment note: “There's a thousand things that are immediate. And I think it's that classic urgent versus important.”