The Exchanges

Q it a nightmare. And so when you're going to do more than one at once, take it. I want to run a hypothetical process with you where you're a advisor or angel in my company, and I am a founder scaling the sales team. We've now identified that I need this scrappy hustler mentality and profile. How do I literally structure the process for hiring a new sales team member?

A So I think from a process perspective is you break down an interview process into, into kind of chunks, if you will. So the first, um, part would be just vetting for, um, and this is a term I learned at Google, which the way just they framed it is really helpful. It's like vetting for just role related knowledge. Do they have knowledge that relates to the role that you feel help would, would say, yes, I want them to kind of go through to the next phase in the process. So Do they demonstrate the characteristics? Do they know enough to be dangerous, right? Then some experience that they can lean on to go forward from, from a, you know, enroll with the company. And then you're the next deal in the process is the how. So how have they been successful? What stories can they lean on and tell you how they've navigated through a win or a loss? Most importantly, a loss who like, how did they bring in different resources? How do they navigate change? Cause You know, a lot of folks will say, oh yes, I want to be part of a startup. I'm ready for it. I'm ready for all the crazy and the chaos, but like, are they really, really want that? So really kind of peel back those layers and ask questions that can help you reveal how they've navigated something really hard. And does that energize them or does that make them go, ah, you know, run away?

AI assessment note: “you break down an interview process into, into kind of chunks, if you will.”

Q You said there about measuring health score. Final one. I could talk to you all day. The final one is actually deal reviews. Crucial part of what we do. How do you structure them? How often do you do them? Who sets the agenda? I've never done them before. I'm this angel investment of yours. What would you advise me?

A I think what's important is a good deal review is based on a common framework. So whatever your framework might be, let's say it's medic. I'm just for, you know, the structure sake that the team participant in the deal review knows what you're going to be asking and can prepare. Not that it should be a big exercise and huge prep. You're not, you know, writing a PhD dissertation to, to do a deal review, but you know, know what we're going to talk about. We're going to talk about the metrics that are important to that customer. We're going to talk about who the economic buyer is. We're going to talk about Their process, um, from a decision-making process and a decision-making, you know, structure. So we're going to talk about those. So common language, really important. Second is you use the deal review to learn and diagnose. You're looking to see, are we on the right track? You're not looking to just like tell someone they're doing a bad job like that. They're going to come in with the defense and tell you what you want to hear and make the deal review not as productive. Also deal review should not be story time. I always say this. It's not your time to tell me a story like Don't say, oh, I met with this person who's connected to this person. I talked to this person. This is what we said. And they said this, I was like, no, I don't, that that's fine that there's a story, but let…

AI assessment note: “a good deal review is based on a common framework. So whatever your framework might be”

Q Ridiculous suggestion. In terms of like the next step, they've blown us away. They're fantastic. And we want to offer it to them. What are some of your biggest lessons on compensation and title when it comes to sales and additions?

A So on compensation, I think you learn a lot in that moment with the candidate. So you learn a lot about them and especially if it's competitive and they might come to you and say, Hey, I'm getting, you know, 50 K more OTE over here. And then you ask, okay, well, what does that mean for you? What does that represent? What is it in equity? Is it an OTE? What is it? And what's driving that ask? So I think it's compensation. It's an opportunity to really understand what motivates that person. And also if they have real, like as a startup, like, do they really believe they're taking a risk? Are they excited about that future opportunity that shows up in equity? You know, what are the questions around equity? Do they, you see an excitement in those questions? And if it comes down to just a dollars on OT, I'm always a little bit like, that's a little, it's not a full red flag depending on, you know, where the conversation goes, but it's something that I concerns me because that will come back You know, in the future where someone's going to be maybe, you know, you have a hard quarter. How do they navigate that? You know, if, if things don't come together, do they have the staying power to work through, you know, the ups and downs that can happen in a startup? So I think it's a moment to really understand what someone's motivations are and also just like see kind of where their, um, re…

AI assessment note: “So on compensation, I think you learn a lot in that moment with the candidate.”

Q How do you create goals that actually align to outcomes versus ticking the box?

A Yeah, no, then I've seen that definitely have had that happen. So that, that is a, you know, I think anyone who's led any sort of sales development team or the team right after the sales development team has experienced that, And I think the way to mitigate that is a few ways is having, you know, a qualification criteria that has to be met. So if it's a band, if it's a, you know, whatever the structure is that identifies kind of the core drivers of that call. But also I think what can make like can validate if that's quality is to have some sort of checkpoint, if you will, of sales stage progression. So let's say you set a meeting and opportunity it's early in stage, but we're going to incentivize when that opportunity goes to the next stage. So when the seller takes over, But they move it forward because that, that is a vote of quality, right? That demonstrates that that opportunity that you created for that salesperson moved forward in their funnel. And that, I think that's a moment of like, yes, we had stage progression off this. This wasn't just like, to your point, like a fluffy meeting that didn't went anywhere. They checked a box. They got the list on the dashboard, all that good stuff. It actually is turning into something. So I think that's another way to just counterbalance and mitigate that. But I think having, you have to have some sort of structure. So, you know, I…

AI assessment note: “we're going to incentivize when that opportunity goes to the next stage”

Q it a nightmare. And so when you're going to do more than one at once, take it. I want to run a hypothetical process with you where you're a advisor or angel in my company, and I am a founder scaling the sales team. We've now identified that I need this scrappy hustler mentality and profile. How do I literally structure the process for hiring a new sales team member?

A So I think from a process perspective is you break down an interview process into, into kind of chunks, if you will. So the first, um, part would be just vetting for, um, and this is a term I learned at Google, which the way just they framed it is really helpful. It's like vetting for just role related knowledge. Do they have knowledge that relates to the role that you feel help would, would say, yes, I want them to kind of go through to the next phase in the process. So Do they demonstrate the characteristics? Do they know enough to be dangerous, right? Then some experience that they can lean on to go forward from, from a, you know, enroll with the company. And then you're the next deal in the process is the how. So how have they been successful? What stories can they lean on and tell you how they've navigated through a win or a loss? Most importantly, a loss who like, how did they bring in different resources? How do they navigate change? Cause You know, a lot of folks will say, oh yes, I want to be part of a startup. I'm ready for it. I'm ready for all the crazy and the chaos, but like, are they really, really want that? So really kind of peel back those layers and ask questions that can help you reveal how they've navigated something really hard. And does that energize them or does that make them go, ah, you know, run away?

AI assessment note: “you break down an interview process into, into kind of chunks, if you will.”

Q No, I, I totally get you. Can I ask, do you ever do discounting? It's often the lever to get deals over the line. How do you think about discounting and how do you advise founders on whether to or not to do it?

A I mean, there's some dependence on, you know, what market you're in, how many competitors, all that good stuff. Like if you're just, if you're, if it's really competitive market and, and there's not as much differentiation as you'd like, you might need to do it to just get a foothold and to make sure you are grabbing market share where you can. I, you know, definitely understand when that has to happen. I think it's all about a trade-off. It's like, what are you, what are you demonstrating from a value trade for that? Is there something that, Hey, I'm going to give you this discount, but exchange for that, um, especially in the early stages, I need references. You know, I need the folks that will speak on our behalf beyond just me said founder or, or sales leader or whomever the person is, is in the engagement. So I think you should just make sure you're preserving value through what that trade-off is with the discount. And I think in the early days, it's like customer stories, it's references, it's introductions to, you know, Hey, could you, are there referrals you can help me with? That can help me broaden my reach that I maybe couldn't get myself. And then also just, of course, you just, you want to not make sure you're demonstrating what that discount represents. So I think it's also, I'm a big fan of like when you're even going to proposal stage, showing it like this is ex…

AI assessment note: “I think it's all about a trade-off. It's like, what are you demonstrating”

Q So what, what questions do you ask? Cause salespeople sell a good game.

A They do. Yeah. No, I think it's like, no, you're absolutely right. Cause you know, there's some great People can interview really well and tricky, right? So I think this, the, the things to dig in on is I like to ask about like a loss. And so, and, and less about like, tell me why you lost, but it's like, what they, what did they do? So, oh, it wasn't, you know, they're not pointing to someone else. They're not saying it was this person's fault. It was my territory. It was this, you know, there's something else other than me, but it was like, what resources did you bring in to help you? What did you learn from that? Like, give me an example of what you learned from that loss and how you brought it to your next win. And what that demonstrates is not only like an ability to kind of reflect and, and, you know, take an experience, learn from it and turn it into action, but also how do they work in a team? Because I think, especially in a startup, like the team is so critical to the success. So how do they partner with other, um, resources in the company to go get something done? I think vetting for that is really important. And then I think, you know, if you hear too many, too many mentions of I, I, I, I mean, of course it's, it's sales and you want folks to be proud of their performance, but if it's too much on just what they did independently, for me, that's a red flag because I …

AI assessment note: “I like to ask about like a loss... what resources did you bring in”

Q How do you know whether you're actually speaking to the economic buyer? A lot of people internally like to pump their chest and I can do this. I can do this.

A Yeah. Well, I think you start from, from doing the discovery with your champion and coach to understand like, who are the stakeholders? Like who ultimately signs, like who actually docu signs this? Whose budget does it come from? And how does this fit into their priorities? That's super important because especially right now, you know, when a lot of companies are looking at saving, you know, and cost cutting and where can they, where can they consolidate? If you haven't sold to the economic buyer that really understands the true value of what you're, you're bringing, it's very likely that you can be consolidated, you know, from away from, but if you have Built value and connection with that economic buyer and they understand what, how that's solving a problem for them. You're mitigating that chance of being, of being consolidated against. So, um, I think it's really understanding like who's the ultimate person where this impacts and if they are looking at their P and L and this is part of it, or they, you know, thumbs up, I'm not changing.

AI assessment note: “doing the discovery with your champion and coach to understand like, who are the stakeholders”

Q Yeah. Um, how do you feel about customer testimonials and what works in terms of getting them?

A I think you have to, that's bold, but I think you have to, um, and I'm a big fan mark, but, um, you have to say there's a caveat around that. Like we've got to prove value. So we've got to prove what we've been telling you for whatever this selling motion period is. We're confident we're going to do that. And in exchange for that, we'd like a testimonial, but I think it's, it's important to ask, but I think it's important to set the framework is like, we're going to meet the goal, the mutual goals that we agreed on. We're going to get you to what you're trying to To reach from a, you know, organization perspective and then ask and then and say, and at that moment, I'm going to come back and ask for it. And I think it's like, it's a seeding opportunity. It also demonstrates that you're staying connected to them for the longterm. I think when a customer really is in partnership with you and believes that you genuinely are looking for a longterm fruitful partnership, they're going to be apt to do that because they believe that that, you know, genuine human connection that you've demonstrated in that great discovery and that great listening Is going to prove to be a really good investment long-term. So I think if you set that stage, then you can get that testimonial, but you should, I think, make sure you're going back to you're going to prove the value that you've said you would b…

AI assessment note: “set the framework is like, we're going to meet the goal... and then ask”

Q How do you advise founders on when's the right time to add that scrappy hungry profile?

A I think it's all about thinking about scale. So if the founder's doing it, and let's say you've got 10 to 20 customers, like how, Much more can they do like just in their, in their straight daily capacity, you know, how much can they get done in, in addition to growing and scaling the company through all the other disciplines, through engineering, through products, through all the other things that kind of overseeing just the operations of the business. So I think it's that moment where you find a repeatable, you've got enough customers and you find enough of a repeatable process that can take your good work and grow it, you know, and, and take and get and have feedback. I think also just someone that you can work with, like, Hey, we've been trying this for the first X number of customers. Let's try something. Let's tune that a little bit. I'll go try that and come back to you with feedback. You try, you know, there's, there's someone you can play with, which I think there's huge value in having partnership, you know, that kind of how many people do you hire at a certain time? There's huge value in being to learn from someone that's next to you. So I think it's a combination of customers, how many you have, and just thinking about the CEO or founder needs to now scale beyond and focus on other things. And this person can help them do that, but they can still stay close.

AI assessment note: “it's that moment where you find a repeatable, you've got enough customers”

Q How do you think about whether to pay up for someone? Versus saying, you know what, you go for the other role.

A I've done that. I've done that. I've said, you know, when someone's really like, this OTE is so, I can't step away from this. And we maybe, maybe you could get closer and bridge it enough. But if that is all they're talking about, sometimes you have to, you have to walk away and say, you know what, that sounds like it's a better fit for you. And if that changes, let's, you know, I always leave a door open. I think it's important that the valley is small, right? You just cannot, you know, shut a door. And so I think it's okay to leave it open, but it's okay to sometimes walk away. I'm trying to think if there's anyone that we walk away from there. I was like, ah, that got away and I, no one's coming to mind. So, you know, that tells me that those weren't the wrong decisions.

AI assessment note: “if that is all they're talking about, sometimes you have to... walk away”

Q this brilliant talent. We've got this team on board. We're going to go to the process of onboarding and working with them. And you said to me before that selling requires active listening and genuine human connection. I read it and felt warm and fuzzy and respectfully didn't have a clue what it meant. What specifically and tangibly can be done to create this active listening and genuine human connection?

A Good question. So the best, one of the most important Characteristics, in my opinion, with a great salesperson is being curious. You have to be curious about not just what you bring to market and excited by that, but what the other person's company role, career path, goals are. Let's, for the sake of the exercise, say we've hired someone that has really, that is curious, that really cares and is interested in that person on the other end of the Zoom call, right? That they're meeting with and they're selling to. What active listening means is if you Walk that back to a core sales skill. It's discovery. So just walking back to like a core, like, you know, common language that we all know in sales, it's discovery. It's someone who can ask a question, who can ask the next question that's connected to that first question. Really listen to the first answer to inform the next question and listen, not just for the answer you want to hear, but the answer you maybe don't want to hear, which is, you know, some Red flag roadblock. That's going to slow down or make the selling engagement difficult. It's listening for the, the places where there's alignment and it's listening for the places where there isn't alignment that we need to go build that alignment through a really tight sales engagement. The way you teach that I think is, I mean, there's a lot of, you know, just discovery I think i…

AI assessment note: “you have to shadow a lot and listen a lot and it's a practice art”

Q Okay, so when we think about that first kind of hire, so to speak, most often go for the logoed rep or the logoed person, but you feel differently. Why do you believe this approach of, like, the hailed logo person isn't maybe the right one?

A A couple reasons. I believe, especially in the early stages, that, um, there's a huge opportunity to not only, like, identify and sprout new talent in a startup, because you're looking for somebody who's demonstrated drive and ambition and all that good stuff, but that doesn't just translate into a huge logo person. It's, like, what gets them energized? How do they navigate through ambiguity? There's an openness to like, I am in it because I'm passionate and I believe in this and I have all the talent to go navigate challenges and to go build something, but I'm not so set in a way that there's only one way to do it. So I think there's a, there's a great benefit you get from not just like creating that environment where you're going to create some great leaders that are going to go grow into other, you know, amazing things and help that company or future companies grow. But there's a mindset That, um, there's a grit and scrappiness that can help you really accelerate through that energy of that team. So I'm a big believer in you can really do great things with maybe a more junior, perceived junior talent, um, because of the creativity they can bring, and they don't have kind of a bias from a previous experience.

AI assessment note: “they don't have kind of a bias from a previous experience.”

Q How do you advise founders on when's the right time to add that scrappy hungry profile?

A I think it's all about thinking about scale. So if the founder's doing it, and let's say you've got 10 to 20 customers, like how, Much more can they do like just in their, in their straight daily capacity, you know, how much can they get done in, in addition to growing and scaling the company through all the other disciplines, through engineering, through products, through all the other things that kind of overseeing just the operations of the business. So I think it's that moment where you find a repeatable, you've got enough customers and you find enough of a repeatable process that can take your good work and grow it, you know, and, and take and get and have feedback. I think also just someone that you can work with, like, Hey, we've been trying this for the first X number of customers. Let's try something. Let's tune that a little bit. I'll go try that and come back to you with feedback. You try, you know, there's, there's someone you can play with, which I think there's huge value in having partnership, you know, that kind of how many people do you hire at a certain time? There's huge value in being to learn from someone that's next to you. So I think it's a combination of customers, how many you have, and just thinking about the CEO or founder needs to now scale beyond and focus on other things. And this person can help them do that, but they can still stay close.

AI assessment note: “it's that moment where you find a repeatable, you've got enough customers”

Q Okay, so when we think about that first kind of hire, so to speak, most often go for the logoed rep or the logoed person, but you feel differently. Why do you believe this approach of, like, the hailed logo person isn't maybe the right one?

A A couple reasons. I believe, especially in the early stages, that, um, there's a huge opportunity to not only, like, identify and sprout new talent in a startup, because you're looking for somebody who's demonstrated drive and ambition and all that good stuff, but that doesn't just translate into a huge logo person. It's, like, what gets them energized? How do they navigate through ambiguity? There's an openness to like, I am in it because I'm passionate and I believe in this and I have all the talent to go navigate challenges and to go build something, but I'm not so set in a way that there's only one way to do it. So I think there's a, there's a great benefit you get from not just like creating that environment where you're going to create some great leaders that are going to go grow into other, you know, amazing things and help that company or future companies grow. But there's a mindset That, um, there's a grit and scrappiness that can help you really accelerate through that energy of that team. So I'm a big believer in you can really do great things with maybe a more junior, perceived junior talent, um, because of the creativity they can bring, and they don't have kind of a bias from a previous experience.

AI assessment note: “they don't have kind of a bias from a previous experience.”

Q Ridiculous suggestion. In terms of like the next step, they've blown us away. They're fantastic. And we want to offer it to them. What are some of your biggest lessons on compensation and title when it comes to sales and additions?

A So on compensation, I think you learn a lot in that moment with the candidate. So you learn a lot about them and especially if it's competitive and they might come to you and say, Hey, I'm getting, you know, 50 K more OTE over here. And then you ask, okay, well, what does that mean for you? What does that represent? What is it in equity? Is it an OTE? What is it? And what's driving that ask? So I think it's compensation. It's an opportunity to really understand what motivates that person. And also if they have real, like as a startup, like, do they really believe they're taking a risk? Are they excited about that future opportunity that shows up in equity? You know, what are the questions around equity? Do they, you see an excitement in those questions? And if it comes down to just a dollars on OT, I'm always a little bit like, that's a little, it's not a full red flag depending on, you know, where the conversation goes, but it's something that I concerns me because that will come back You know, in the future where someone's going to be maybe, you know, you have a hard quarter. How do they navigate that? You know, if, if things don't come together, do they have the staying power to work through, you know, the ups and downs that can happen in a startup? So I think it's a moment to really understand what someone's motivations are and also just like see kind of where their, um, re…

AI assessment note: “So on compensation, I think you learn a lot in that moment with the candidate.”

Q Final, final one, I promise. But like, this is like all predicting pipeline and predicting How much we're going to make bluntly? One of your friends said that you're one of the best in the world to quote at predictable sales execution. How do you think about forecasting with accuracy when times are as challenging as they are in terms of volatility?

A First, that's a really nice friend. So I don't know who said that, but that's it. But thank you, friend. Um, I would say it's that back to that balance of you have to have, you know, you have to set the foundation that there's going to be a level of accountability to the forecast and you have to dig in with the forecast when you are in a high and when you are in a low. So oftentimes you'll see like the forecast inspection happens when you're having a down quarter forecast inspection needs to happen In the best of quarters, because if you just only pivot to when you're down, then it's in a fear based moment and you're making decisions that are informed by that stress of missing. You've got to have that same level of rigor all the time. And you got to teach your leaders that you've got to demonstrate that that's really important. You're going to have rigor when you're having the best quarter and you're gonna have rigor when you're having the worst quarter. And so you learn that and you teach that and that becomes kind of your basis for accountability. And I think right now, especially in 20, 23, it's hard to anticipate. So it's back to like, Having really healthy skepticism about every deal. Like they could be telling, it could look beautiful, but like, let's just go in with a skeptical mindset and shoot holes in this because we don't have the benefit of a buffer. We don't have a…

AI assessment note: “Having really healthy skepticism about every deal.”

Q this brilliant talent. We've got this team on board. We're going to go to the process of onboarding and working with them. And you said to me before that selling requires active listening and genuine human connection. I read it and felt warm and fuzzy and respectfully didn't have a clue what it meant. What specifically and tangibly can be done to create this active listening and genuine human connection?

A Good question. So the best, one of the most important Characteristics, in my opinion, with a great salesperson is being curious. You have to be curious about not just what you bring to market and excited by that, but what the other person's company role, career path, goals are. Let's, for the sake of the exercise, say we've hired someone that has really, that is curious, that really cares and is interested in that person on the other end of the Zoom call, right? That they're meeting with and they're selling to. What active listening means is if you Walk that back to a core sales skill. It's discovery. So just walking back to like a core, like, you know, common language that we all know in sales, it's discovery. It's someone who can ask a question, who can ask the next question that's connected to that first question. Really listen to the first answer to inform the next question and listen, not just for the answer you want to hear, but the answer you maybe don't want to hear, which is, you know, some Red flag roadblock. That's going to slow down or make the selling engagement difficult. It's listening for the, the places where there's alignment and it's listening for the places where there isn't alignment that we need to go build that alignment through a really tight sales engagement. The way you teach that I think is, I mean, there's a lot of, you know, just discovery I think i…

AI assessment note: “It's someone who can ask a question, who can ask the next question”

Q How do you know whether you're actually speaking to the economic buyer? A lot of people internally like to pump their chest and I can do this. I can do this.

A Yeah. Well, I think you start from, from doing the discovery with your champion and coach to understand like, who are the stakeholders? Like who ultimately signs, like who actually docu signs this? Whose budget does it come from? And how does this fit into their priorities? That's super important because especially right now, you know, when a lot of companies are looking at saving, you know, and cost cutting and where can they, where can they consolidate? If you haven't sold to the economic buyer that really understands the true value of what you're, you're bringing, it's very likely that you can be consolidated, you know, from away from, but if you have Built value and connection with that economic buyer and they understand what, how that's solving a problem for them. You're mitigating that chance of being, of being consolidated against. So, um, I think it's really understanding like who's the ultimate person where this impacts and if they are looking at their P and L and this is part of it, or they, you know, thumbs up, I'm not changing.

AI assessment note: “who ultimately signs, like who actually docu signs this? Whose budget does it come from?”

Q What do you mean the how, like the ways in which they achieved were murky, like it was non-ethical?

A Yeah, exactly. And then I think another piece is, um, you know, I don't think you need to do a million references, because people are going to send you the references, of course, they're going to say all the good things, but I do think if you can get some connection to people that have worked alongside with some sort of, you know, reference backdoor that, Shares a little bit more insight is helpful. And I think in places where we may be moving too fast, because we really had to get it done and couldn't get some of that, those, those additional touch points that, that we could have maybe seen around a corner, um, in advance. And I think, you know, again, it's, it's a lot of it is folks want to say they're ready for a startup, you know, and like, I'm all about it. It's going to be great. I'm in for the, I'm in for the journey. And then they get there and they're like, wait, what? You know, so it's, so I think that's, I mean, I've made some mistakes there. It's, it's hard to bet, honestly, because it's hard to say, like, you can anticipate everything and prepare someone for that. But there's been some places where it's like, this is just too fast and too ambiguous and too crazy. And I, I can't, you know, so, um, but that that's, that's, I think you should expect one of those every once in a while. Right.

AI assessment note: “Yeah, exactly. And then I think another piece is”