Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered produced feed
D 5 · C 5 · P 5 · Cm 5 5.00
Q start with, you know, I always start with context and kind of a little bit of history, but Philman said that we should start with the first attempt at leadership, and he said actually your first attempt at leadership was challenging and had ups and downs, and he said that that would be an interesting place to start and dig in on some lessons from that. Can we start there?
A Let's do it. So hopefully I won't, I won't like get emotional, but most of my career was in the telecom industry. I worked for Sprint and I started in customer service, worked my way all the way up to the sales organization. I was running their international wholesale business, big job, global experience. I left Sprint to be a CRO of a midsize media company that was trying to go all digital. And at the time, Harry, I was the smartest guy in the room. I had a big ego. I alienated people there that could help me because it was all about my career. My results. After a year, that's just a bad way to lead. I got fired. So this was maybe eight years ago, so I was unemployed for six months, and part of the time I was a bartender.
AI assessment note: “I alienated people there that could help me... I got fired.”
Answered produced feed
D 5 · C 5 · P 5 · Cm 5 5.00
Q start with, you know, I always start with context and kind of a little bit of history, but Philman said that we should start with the first attempt at leadership, and he said actually your first attempt at leadership was challenging and had ups and downs, and he said that that would be an interesting place to start and dig in on some lessons from that. Can we start there?
A Let's do it. So hopefully I won't, I won't like get emotional, but most of my career was in the telecom industry. I worked for Sprint and I started in customer service, worked my way all the way up to the sales organization. I was running their international wholesale business, big job, global experience. I left Sprint to be a CRO of a midsize media company that was trying to go all digital. And at the time, Harry, I was the smartest guy in the room. I had a big ego. I alienated people there that could help me because it was all about my career. My results. After a year, that's just a bad way to lead. I got fired. So this was maybe eight years ago, so I was unemployed for six months, and part of the time I was a bartender.
AI assessment note: “I left Sprint to be a CRO... I had a big ego... I got fired.”
Answered produced feed
D 5 · C 5 · P 5 · Cm 4 4.85
Q When you get fired, and when you have a really hard moment like that, how do you mentally respond? Like, what were you thinking when you left that office?
A Quite frankly, I broke down. Like, I was, I was in tears. I never failed at anything before, and that was the first time I failed. But really, I did a lot of self-reflection on what true leadership is, Listening skills are really important, so I had to reinvent myself, and then I had a friend, his name was Ryan Ratting. He's a senior executive at Salesforce, and at the time, he was a second line sales leader, and he was like, dude, you should come over to Salesforce. You know the product, you would do really well here, but no one's gonna hire you as a senior leader. You're gonna have to come in and kind of prove yourself. So I had to swallow my pride, and I came in to Salesforce eight years ago as a first line sales leader. All the way from a, you know, a CRO to a first line sales leader, but this time I came in with humility, with respect, listening, putting people first, and my career at Salesforce really flourished because I reinvented myself based on failing as a CRO with a big ego.
AI assessment note: “Quite frankly, I broke down. Like, I was, I was in tears.”
Answered produced feed
D 5 · C 5 · P 5 · Cm 4 4.85
Q When you get fired, and when you have a really hard moment like that, how do you mentally respond? Like, what were you thinking when you left that office?
A Quite frankly, I broke down. Like, I was, I was in tears. I never failed at anything before, and that was the first time I failed. But really, I did a lot of self-reflection on what true leadership is, Listening skills are really important, so I had to reinvent myself, and then I had a friend, his name was Ryan Ratting. He's a senior executive at Salesforce, and at the time, he was a second line sales leader, and he was like, dude, you should come over to Salesforce. You know the product, you would do really well here, but no one's gonna hire you as a senior leader. You're gonna have to come in and kind of prove yourself. So I had to swallow my pride, and I came in to Salesforce eight years ago as a first line sales leader. All the way from a, you know, a CRO to a first line sales leader, but this time I came in with humility, with respect, listening, putting people first, and my career at Salesforce really flourished because I reinvented myself based on failing as a CRO with a big ego.
AI assessment note: “Quite frankly, I broke down. Like, I was, I was in tears.”
Answered produced feed
D 5 · C 5 · P 5 · Cm 4 4.85
Q How do you think about the volume of resolutions? In other words, we're 90% at resolutions, or 85%, whatever it is, versus we solve the really, really difficult ones.
A Our vision for all of our clients is to be the front door and the concierge of their experience. So we can handle the easy stuff, But we can also, where we really, really thrive and shine and excel is the really complex things. Like, for example, if you're a Sonos customer and your Sonos system stops working, our agent is sophisticated enough to figure out, is it your Wi-Fi? Is it the software on the speaker? Or is it the hardware? So it's got the ability to handle that kind of complexity. If you're a serious XM customer, not only can we tell you what station shade 45 hip hop music is playing on, But we can also, if your radio stops working in your car, our agent will call the satellite and resend the encryption keys back to your car to get your satellite radio working. So this technology, it can handle very, very sophisticated things. So our job, our goal is to put, once again, your best sales rep, your best customer service agent in front of your customers, 24 seven.
AI assessment note: “we can handle the easy stuff, But we can also... excel is the really complex things”
Answered produced feed
D 5 · C 5 · P 5 · Cm 4 4.85
Q We mentioned running deals, and then you said about negotiating deals, and negotiating is where Deals can slip and where deals can not happen. What are your biggest lessons on how to and how not to negotiate large enterprise deals?
A That's great. There's different variations of enterprise sales negotiations, but it really comes back to, are you delivering value? Are you solving a problem? Are you talking to the right people? Have you done your homework? Have you built business value in or return on investment so the client can see the technology they're investing in? What are they going to get out of it? And then are you talking to the right people? Are you leveraging the power of your, of Sierra? Are you getting me involved? Are you getting Elliot Greenwald, our co-founders involved? Like, are you loading up the boat to make sure you have the right people helping you negotiate these deals? Where are you weak? Does someone else better at like negotiating like this, the financial structure of the deal? Let's get them in the boat with you. So do we need to get our general counsel, Jonathan Millard involved? Like use all the resources, all these talented people To help you get your deal across, but just know where your strengths and weaknesses are, and then know where to fill those gaps.
AI assessment note: “use all the resources, all these talented people To help you get your deal across”
Answered produced feed
D 5 · C 5 · P 4 · Cm 3 4.45
Q And you have outcome-based pricing, which is a very different structure of pricing to traditional SaaS, which has always been seat-based pricing. Now, I always worry that when you are introducing something new, It is uncertain and people need educating. How has the process been in terms of introducing really a relatively new pricing mechanism to traditional enterprise customers who aren't used to it?
A This is the most fun I've had as a sales leader in my entire career because I'm selling a business model that people get immediately. They no longer have to pay for the right to use software. They don't pay for seats. They don't pay for consumption. They pay for outcomes. Did our agent solve a problem? Did our agent convert a sale? Did it make the right product recommendation? If so, we get paid. And oh, by the way, it's a fraction of what you're paying human beings to do this work. So people get it. We don't charge implementation fees or any integration work. We absorb all of that. So when you partner with Sierra, you're paying for outcomes, you're paying for results. And it's just the fun model that people get. And it's fun to be in the space. And we're creating a brand new category of software and the way we price it and the way people consume it. It's really fun.
AI assessment note: “selling a business model that people get immediately”
Answered produced feed
D 5 · C 5 · P 4 · Cm 3 4.45
Q And you have outcome-based pricing, which is a very different structure of pricing to traditional SaaS, which has always been seat-based pricing. Now, I always worry that when you are introducing something new, It is uncertain and people need educating. How has the process been in terms of introducing really a relatively new pricing mechanism to traditional enterprise customers who aren't used to it?
A This is the most fun I've had as a sales leader in my entire career because I'm selling a business model that people get immediately. They no longer have to pay for the right to use software. They don't pay for seats. They don't pay for consumption. They pay for outcomes. Did our agent solve a problem? Did our agent convert a sale? Did it make the right product recommendation? If so, we get paid. And oh, by the way, it's a fraction of what you're paying human beings to do this work. So people get it. We don't charge implementation fees or any integration work. We absorb all of that. So when you partner with Sierra, you're paying for outcomes, you're paying for results. And it's just the fun model that people get. And it's fun to be in the space. And we're creating a brand new category of software and the way we price it and the way people consume it. It's really fun.
AI assessment note: “I'm selling a business model that people get immediately.”
Answered produced feed
D 4 · C 5 · P 4 · Cm 4 4.30
Q So let's give them a shot, right? Let's do it. And there's two parts where I find really telling of a candidate in terms of how they think, which is salary and title. How do you learn about the candidate from salary and title? So is it bad for If I come in and say, I want to be a VP of sales.
A At Sierra, what we do is everyone comes in as an individual contributor for a certain period, even if you were in leadership, like myself included. Once again, as I said before, when I started, there was no sales team. So I was an AE, I was an SDR, I was a BDR, took the trash out. I kind of like earned my right to kind of lead a team. And all of the sales leaders that we brought into Sierra, they came in for a period of time to be an IC. And that takes humility. I mean, you've got to like master your craft. You've got to learn how to prospect. You've got to learn how to run a deal. You've got to learn how to negotiate a deal. And I think that's important and powerful. So when you do start running a team, you know how to lead your team, especially when this is a brand new category of software. We're a new company. So I think it's important for people to come in and kind of earn, earn their leadership. And Michael Jordan says, like, earn your leadership every day. I still feel like I'm earning my leadership every day, but that's just how we approach it. Now over time that may change.
AI assessment note: “everyone comes in as an individual contributor for a certain period, even if you were in leadership”
Answered produced feed
D 5 · C 4 · P 4 · Cm 4 4.30
Q You mentioned generational wealth there. Often sales reps teams are suggested to be coin-operated, more mercenary than other functions. To what extent do you find salespeople, and I know it's generalists, so forgive me for it, but it's a podcast, mission-driven versus money-driven?
A It's a great question. That's like the million dollar question about sales. Obviously, everyone wants to go into sales. People want to make money because there is unlimited compensation. But I also think people like being part of something special. I think people like being creators and trailblazers and helping to build something. So I think that's an aspect. People love recognition. You get into sales for recognition. But I think also people get into sales because they're intellectually curious. They love how companies make money. They want to help these companies be successful. So there's a lot of other reasons why people get into sales. I also find that a lot of former athletes get into sales, like myself. I was a former, I played college American football, and I played-
AI assessment note: “People want to make money because there is unlimited compensation. But I also think”
Answered produced feed
D 3 · C 5 · P 5 · Cm 4 4.25
Q How do you think about the volume of resolutions? In other words, we're 90% at resolutions, or 85%, whatever it is, versus we solve the really, really difficult ones.
A Our vision for all of our clients is to be the front door and the concierge of their experience. So we can handle the easy stuff, But we can also, where we really, really thrive and shine and excel is the really complex things. Like, for example, if you're a Sonos customer and your Sonos system stops working, our agent is sophisticated enough to figure out, is it your Wi-Fi? Is it the software on the speaker? Or is it the hardware? So it's got the ability to handle that kind of complexity. If you're a serious XM customer, not only can we tell you what station shade 45 hip hop music is playing on, But we can also, if your radio stops working in your car, our agent will call the satellite and resend the encryption keys back to your car to get your satellite radio working. So this technology, it can handle very, very sophisticated things. So our job, our goal is to put, once again, your best sales rep, your best customer service agent in front of your customers, 24 seven.
AI assessment note: “where we really, really thrive and shine and excel is the really complex things.”
Answered produced feed
D 5 · C 4 · P 4 · Cm 3 4.15
Q We mentioned running deals, and then you said about negotiating deals, and negotiating is where Deals can slip and where deals can not happen. What are your biggest lessons on how to and how not to negotiate large enterprise deals?
A That's great. There's different variations of enterprise sales negotiations, but it really comes back to, are you delivering value? Are you solving a problem? Are you talking to the right people? Have you done your homework? Have you built business value in or return on investment so the client can see the technology they're investing in? What are they going to get out of it? And then are you talking to the right people? Are you leveraging the power of your, of Sierra? Are you getting me involved? Are you getting Elliot Greenwald, our co-founders involved? Like, are you loading up the boat to make sure you have the right people helping you negotiate these deals? Where are you weak? Does someone else better at like negotiating like this, the financial structure of the deal? Let's get them in the boat with you. So do we need to get our general counsel, Jonathan Millard involved? Like use all the resources, all these talented people To help you get your deal across, but just know where your strengths and weaknesses are, and then know where to fill those gaps.
AI assessment note: “use all the resources, all these talented people To help you get your deal across”
Answered produced feed
D 5 · C 4 · P 4 · Cm 3 4.15
Q Do you agree? What the larger enterprise contract will be pre POC. In other words, when you sign the POC, do you say, if we hit X goals, we will sign Y contract?
A No, it's somewhat fluid. I mean, we have, I think the client in our team, we have an idea of what the potential could be, but in order for us to even get to the potential, talk about the potential, we need to execute in the proof of concept based on the journeys that we're going to build and the results that they want to see. But we do have somewhat of an idea of kind of potentially where this could be, and our vision is to be the front door of their experience, be their concierge, put their best sales professional, their best customer service agent in front of their customers, 24 seven. But we've got to earn our right to be able to, to be the front door of the experience by executing in the proof of concept.
AI assessment note: “No, it's somewhat fluid. I mean, we have... an idea of what the potential could be”
Answered produced feed
D 4 · C 5 · P 4 · Cm 3 4.15
Q I totally agree with you. Do you think we demonize the money chasing? I think it's great. If you want to make money, And you're like, I want to make a lot of money, and I'm here to crush it. I'm like, great. But I think a lot of people go, oh, they're not here for the mission, and they're not here to have impact. Fine.
A It's quite okay to want to, you know, make a lot of money, but I think it's more of what I try to do when I interview people is connect, like, what is your why? Like, what motivates you every day? Why do you get up, and why do you get after it every single day? And what you'll find, it's not the money, it's what the money can do. It's like providing a better life for your family, sending your kids to college or private school. Or being able to get on a flight and travel first class. I think it's not just about the cash. It's about what the cash can do. So I always try to connect with people's why and what's motivating them.
AI assessment note: “It's quite okay to want to, you know, make a lot of money”
Answered produced feed
D 4 · C 4 · P 4 · Cm 4 4.00
Q Why? What makes him so good at sales?
A Brett has the ability to articulate and connect the technology to actual business, and he makes it simple for people to understand and follow, and he's a great storyteller. They had a pretty strong process because we had design customers, a proof of concept selling motion, so there were some things in place, but What I was able to do with our leadership team was take that to the next level and really define our sales process. And huge shout out to my sales methodologies like Medic and the Challenger Sale. We've taken all of that. We call ours peer, and that is, um, partnerships, use case, ROI, and then I love this one, event comma compelling. So we've kind of elevated what we've learned to different, um, experiences and created a new sales process, which we're executing.
AI assessment note: “Brett has the ability to articulate and connect the technology to actual business”
Answered produced feed
D 5 · C 4 · P 3 · Cm 3 3.90
Q What do you advise on competition? You do have competitors. Every space does. It's worth something really. How do you advise founders on how to think about competition and also just how to message about competition in sales cycles?
A We are in a ultra competitive environment. We're competing with big tech. We're competing with startups. We're competing with, I can build this myself. We're competing with, I'm too scared to put AI in front of my customers. So there's lots of competition, but I just think it is make basically understanding your message. Understanding how to combat what your competitor is going to throw against you. Understanding your competition, respecting your competition. Don't take your competition for granted, but know your strengths of how you can beat your competition and just making sure your team is enabled on that and not, don't be scared to compete. I love to compete. I love waking up every day and knowing that every client that I'm chasing, someone else is chasing that client too, and I need to show up better, stronger, faster, more craftsmanship. Make sure my product, you know, we have an awesome product to sell. So that, that's kind of how I think about competition. I love it. It's always going to be there, especially in AI, but just understanding your competition, respect your competition, and know how to sell against them.
AI assessment note: “understanding your competition, respect your competition, and know how to sell against them.”
Answered produced feed
D 4 · C 4 · P 4 · Cm 3 3.85
Q of mine says, don't do it. It's not possible. A question that I have for you is, are you a unique situation respectfully because you're Brett Taylor and the team is so stellar? If you're like a normal team with great founders, but you're 25, you're 30, whatever, do you think this is an isolated incident where basically you can get people like you Because of who the founders are.
A The bread and clay factor obviously definitely helps, but I still think it's a startup, and there's a lot of uncertainty, a lot of unknown, and what I sell, I don't sell, I just try to teach people what the vision of where this could go, and in my heart and soul, I believe Sierra is going to be one of the most important companies in AI, and I tell people that you have an opportunity to be on the ground floor of one of the most important technology companies in the world. And also this is an opportunity to create real generational wealth for your family if we execute. And then also I look at it too. The reason, one of the reasons I came is like, I want to be a legend, man. I want to be a trailblazer. I want to help, you know, make Sierra a generational company and then open up doors for other, you know, minorities to get these kinds of opportunities and take these kinds of risks. And I always go back to this quote from Muhammad Ali. If your dreams don't scare you, they're not big enough. So the most important decisions I've made in my career is when it's scary and when it's uncomfortable. If you can convince people to see where potentially this company is going to go, then it's much easier to recruit them.
AI assessment note: “The bread and clay factor obviously definitely helps, but I still think it's a startup”
Answered produced feed
D 4 · C 4 · P 4 · Cm 3 3.85
Q of mine says, don't do it. It's not possible. A question that I have for you is, are you a unique situation respectfully because you're Brett Taylor and the team is so stellar? If you're like a normal team with great founders, but you're 25, you're 30, whatever, do you think this is an isolated incident where basically you can get people like you Because of who the founders are.
A The bread and clay factor obviously definitely helps, but I still think it's a startup, and there's a lot of uncertainty, a lot of unknown, and what I sell, I don't sell, I just try to teach people what the vision of where this could go, and in my heart and soul, I believe Sierra is going to be one of the most important companies in AI, and I tell people that you have an opportunity to be on the ground floor of one of the most important technology companies in the world. And also this is an opportunity to create real generational wealth for your family if we execute. And then also I look at it too. The reason, one of the reasons I came is like, I want to be a legend, man. I want to be a trailblazer. I want to help, you know, make Sierra a generational company and then open up doors for other, you know, minorities to get these kinds of opportunities and take these kinds of risks. And I always go back to this quote from Muhammad Ali. If your dreams don't scare you, they're not big enough. So the most important decisions I've made in my career is when it's scary and when it's uncomfortable. If you can convince people to see where potentially this company is going to go, then it's much easier to recruit them.
AI assessment note: “The bread and clay factor obviously definitely helps, but I still think it's a startup”
Answered produced feed
D 5 · C 4 · P 3 · Cm 2 3.75
Q Do you agree? What the larger enterprise contract will be pre POC. In other words, when you sign the POC, do you say, if we hit X goals, we will sign Y contract?
A No, it's somewhat fluid. I mean, we have, I think the client in our team, we have an idea of what the potential could be, but in order for us to even get to the potential, talk about the potential, we need to execute in the proof of concept based on the journeys that we're going to build and the results that they want to see. But we do have somewhat of an idea of kind of potentially where this could be, and our vision is to be the front door of their experience, be their concierge, put their best sales professional, their best customer service agent in front of their customers, 24 seven. But we've got to earn our right to be able to, to be the front door of the experience by executing in the proof of concept.
AI assessment note: “No, it's somewhat fluid.”
Answered produced feed
D 4 · C 4 · P 3 · Cm 3 3.60
Q You mentioned generational wealth there. Often sales reps teams are suggested to be coin-operated, more mercenary than other functions. To what extent do you find salespeople, and I know it's generalists, so forgive me for it, but it's a podcast, mission-driven versus money-driven?
A It's a great question. That's like the million dollar question about sales. Obviously, everyone wants to go into sales. People want to make money because there is unlimited compensation. But I also think people like being part of something special. I think people like being creators and trailblazers and helping to build something. So I think that's an aspect. People love recognition. You get into sales for recognition. But I think also people get into sales because they're intellectually curious. They love how companies make money. They want to help these companies be successful. So there's a lot of other reasons why people get into sales. I also find that a lot of former athletes get into sales, like myself. I was a former, I played college American football, and I played-
AI assessment note: “People want to make money because there is unlimited compensation. But I also think”
Answered produced feed
D 4 · C 4 · P 3 · Cm 3 3.60
Q Do you have any lessons? I find this hard actually as a leader today. Do you have any lessons in how to give feedback that's hard, but in a way that doesn't discourage them moving forwards and kind of make sure they leave inspired with their head up?
A Yeah. So it starts off with, I think the leadership style and your principles. So I start off with, I'm open, I'm honest, I'm transparent. I lead from the front. I treat people with respect. I would never ask someone to do something I wouldn't do myself, but I also have high expectations and I'm very clear about what's expected. So I think if you lead with that type of energy and people know what to expect. So I think delivering feedback because you're doing it quite often is pretty easy. As long as you're, you're respectful, but you're honest and you also are open to receiving feedback. People will accept your feedback, and they'll also listen and action your feedback. If you're willing, you do it in a respectful way, but you're also open to getting feedback back. I get lots of feedback, not only from my colleagues, but also my wife and my children.
AI assessment note: “As long as you're, you're respectful, but you're honest and you also are open”
Answered produced feed
D 4 · C 4 · P 3 · Cm 3 3.60
Q Do you think it has a higher hit rate when the founders or the heads of sale Does it versus AEs and BDRs and you name it?
A I think so, but I also think it comes down to messaging and timing. If you have a relevant message, I think that captures people's attention. I think everyone is trying to figure out AI, how to put AI to work and how to use AI to solve problems and reduce costs. So I think our message is resonating, but it's very competitive and it's hard. If you're consistent with it, you know, we now have customer stories. We had a lot of very successful customer stories, so we can lean into that as well. But at the end of the day, You have to be the one to initiate the conversation, and I think that's why I'm aggressive and I'm making cold calls and prospecting myself.
AI assessment note: “I think so, but I also think it comes down to messaging and timing.”
Answered produced feed
D 4 · C 4 · P 3 · Cm 3 3.60
Q Do you have any lessons? I find this hard actually as a leader today. Do you have any lessons in how to give feedback that's hard, but in a way that doesn't discourage them moving forwards and kind of make sure they leave inspired with their head up?
A Yeah. So it starts off with, I think the leadership style and your principles. So I start off with, I'm open, I'm honest, I'm transparent. I lead from the front. I treat people with respect. I would never ask someone to do something I wouldn't do myself, but I also have high expectations and I'm very clear about what's expected. So I think if you lead with that type of energy and people know what to expect. So I think delivering feedback because you're doing it quite often is pretty easy. As long as you're, you're respectful, but you're honest and you also are open to receiving feedback. People will accept your feedback, and they'll also listen and action your feedback. If you're willing, you do it in a respectful way, but you're also open to getting feedback back. I get lots of feedback, not only from my colleagues, but also my wife and my children.
AI assessment note: “delivering feedback because you're doing it quite often is pretty easy”
Redirected produced feed
D 3 · C 4 · P 4 · Cm 3 3.55
Q Why? What makes him so good at sales?
A Brett has the ability to articulate and connect the technology to actual business, and he makes it simple for people to understand and follow, and he's a great storyteller. They had a pretty strong process because we had design customers, a proof of concept selling motion, so there were some things in place, but What I was able to do with our leadership team was take that to the next level and really define our sales process. And huge shout out to my sales methodologies like Medic and the Challenger Sale. We've taken all of that. We call ours peer, and that is, um, partnerships, use case, ROI, and then I love this one, event comma compelling. So we've kind of elevated what we've learned to different, um, experiences and created a new sales process, which we're executing.
AI assessment note: “Brett has the ability to articulate and connect the technology to actual business”
Redirected produced feed
D 3 · C 4 · P 4 · Cm 3 3.55
Q I totally agree with you. Do you think we demonize the money chasing? I think it's great. If you want to make money, And you're like, I want to make a lot of money, and I'm here to crush it. I'm like, great. But I think a lot of people go, oh, they're not here for the mission, and they're not here to have impact. Fine.
A It's quite okay to want to, you know, make a lot of money, but I think it's more of what I try to do when I interview people is connect, like, what is your why? Like, what motivates you every day? Why do you get up, and why do you get after it every single day? And what you'll find, it's not the money, it's what the money can do. It's like providing a better life for your family, sending your kids to college or private school. Or being able to get on a flight and travel first class. I think it's not just about the cash. It's about what the cash can do. So I always try to connect with people's why and what's motivating them.
AI assessment note: “what I try to do when I interview people is connect, like, what is your why”
Partly produced feed
D 3 · C 4 · P 4 · Cm 3 3.55
Q So let's give them a shot, right? Let's do it. And there's two parts where I find really telling of a candidate in terms of how they think, which is salary and title. How do you learn about the candidate from salary and title? So is it bad for If I come in and say, I want to be a VP of sales.
A At Sierra, what we do is everyone comes in as an individual contributor for a certain period, even if you were in leadership, like myself included. Once again, as I said before, when I started, there was no sales team. So I was an AE, I was an SDR, I was a BDR, took the trash out. I kind of like earned my right to kind of lead a team. And all of the sales leaders that we brought into Sierra, they came in for a period of time to be an IC. And that takes humility. I mean, you've got to like master your craft. You've got to learn how to prospect. You've got to learn how to run a deal. You've got to learn how to negotiate a deal. And I think that's important and powerful. So when you do start running a team, you know how to lead your team, especially when this is a brand new category of software. We're a new company. So I think it's important for people to come in and kind of earn, earn their leadership. And Michael Jordan says, like, earn your leadership every day. I still feel like I'm earning my leadership every day, but that's just how we approach it. Now over time that may change.
AI assessment note: “everyone comes in as an individual contributor for a certain period, even if you were in leadership”
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D 4 · C 4 · P 2 · Cm 2 3.20
Q What do you advise on competition? You do have competitors. Every space does. It's worth something really. How do you advise founders on how to think about competition and also just how to message about competition in sales cycles?
A We are in a ultra competitive environment. We're competing with big tech. We're competing with startups. We're competing with, I can build this myself. We're competing with, I'm too scared to put AI in front of my customers. So there's lots of competition, but I just think it is make basically understanding your message. Understanding how to combat what your competitor is going to throw against you. Understanding your competition, respecting your competition. Don't take your competition for granted, but know your strengths of how you can beat your competition and just making sure your team is enabled on that and not, don't be scared to compete. I love to compete. I love waking up every day and knowing that every client that I'm chasing, someone else is chasing that client too, and I need to show up better, stronger, faster, more craftsmanship. Make sure my product, you know, we have an awesome product to sell. So that, that's kind of how I think about competition. I love it. It's always going to be there, especially in AI, but just understanding your competition, respect your competition, and know how to sell against them.
AI assessment note: “understanding your competition, respecting your competition. Don't take your competition for granted”
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D 3 · C 3 · P 3 · Cm 3 3.00
Q Do you think it has a higher hit rate when the founders or the heads of sale Does it versus AEs and BDRs and you name it?
A I think so, but I also think it comes down to messaging and timing. If you have a relevant message, I think that captures people's attention. I think everyone is trying to figure out AI, how to put AI to work and how to use AI to solve problems and reduce costs. So I think our message is resonating, but it's very competitive and it's hard. If you're consistent with it, you know, we now have customer stories. We had a lot of very successful customer stories, so we can lean into that as well. But at the end of the day, You have to be the one to initiate the conversation, and I think that's why I'm aggressive and I'm making cold calls and prospecting myself.
AI assessment note: “I think so, but I also think it comes down to messaging and timing.”