The Exchanges

Q advice on my own life. I sit on quite a few boards and they often say, ah, the deal was about to convert, but then they pushed it to next quarter. And I'm always like, how do I respond to that? Legitimately there could be reasons and then otherwise it could just not be legitimate reasons. How do you respond to the statement? Ah, it got pushed to next quarter.

A So the first question would be, did you have mutual agreement with the prospect on when we would execute? So did you work on a mutual evaluation plan or some sort of joint evaluation plan that had milestones that said, this is the timeframe that we both agree to. If the answer is yes. And the circumstance that pushed it is something like, you know, we've seen this in 20, 23 and the end of 20, 22, if there's some internal event, let's say there's a riff. You know, like, Hey, we were going down this process. We were all in with you, but we just had a reduction in force. We have to pause. We have to reassess, but this is still a priority. Then that's, you know, it's hard to anticipate that, right? Like an external person can't anticipate that. But if it's like, I, you know, I was told this was the timing. My person agreed. Okay. Maybe you never had access to the economic buyer. You really were just working with a champion that didn't have the power to really understand the buying process. So a lot of the core of that, like if it's, if it's, um, A result of the salesperson's engagement. It's because there wasn't access to the economic buyer. That's usually like the number one part of medic that makes it fail is you're just not, you're not there.

AI assessment note: “So the first question would be, did you have mutual agreement with the prospect”

Q and startup. So I was like, I don't know if that's a positive or not, but I'm all in for this. But then my problem is, okay, we've got this beautiful, genuine, you know, connection, human relationship. Speak to my CS team now, cause you're handed off. That handoff feels quite Dehumanized. How do you think about retaining genuine human connection care relationship with a very efficient, but dehumanized handoff?

A Yeah, no, I think you can't make it dehumanized and I'm in my role today. I'm responsible for all, you know, from sales through to customer success through to support and we operate as a revenue organization. So we don't operate as a sales organization and an implementation organization. And a success organization and a support organization is one. And what we prioritize to make that not feel like a handoff is the conversation that happens. We are engaged in each part. So for example, if we're gonna, if we're, you know, closing out our quarter and we're about to plan an implementation and the next phase of that customer's journey, that implementation managers on that last call and they meet them and they say, this is my colleague. These are some of the customers that they've worked with. They're a rock star. They're gonna carry you through. And I'm gonna join when you go to launch that last call. So it's like, you've gotta not hand the baton off and then let go. You've gotta hand the baton off, but say I'm coming back and I'm gonna stay connected. And you can also do that with just like structure of how you compensate people with upsell and things like that. So to make sure there's an incentive, but I think you've gotta show it. Like you actually have to show up to the call and, and stay engaged. And then additionally, Let's say you're now with a customer, you've launched, you'…

AI assessment note: “You've gotta hand the baton off, but say I'm coming back and I'm gonna stay connected.”

Q So I totally agree. Final one for you, which company sales strategy have you most been impressed by recently? Where you look at it and you're like smart.

A Yeah, actually we recently, um, it's recency, but we recently bought vitally for our customer success team. So customer success platform. And what I was really impressed with is, um, really clear communication the whole way and very direct and engaging, but What I really have noticed is post-sale is how they continue to stay connected and care about the success of our launch. And especially in this time where gross retention, you know, is so important and thinking about retaining every customer that you spent so much time earning, they've stayed connected through that whole process. So really clear communication, great sales process upfront, but they're continuing it through all the way as we've become a customer. So I've been very impressed by that.

AI assessment note: “we recently bought vitally for our customer success team”

Q and startup. So I was like, I don't know if that's a positive or not, but I'm all in for this. But then my problem is, okay, we've got this beautiful, genuine, you know, connection, human relationship. Speak to my CS team now, cause you're handed off. That handoff feels quite Dehumanized. How do you think about retaining genuine human connection care relationship with a very efficient, but dehumanized handoff?

A Yeah, no, I think you can't make it dehumanized and I'm in my role today. I'm responsible for all, you know, from sales through to customer success through to support and we operate as a revenue organization. So we don't operate as a sales organization and an implementation organization. And a success organization and a support organization is one. And what we prioritize to make that not feel like a handoff is the conversation that happens. We are engaged in each part. So for example, if we're gonna, if we're, you know, closing out our quarter and we're about to plan an implementation and the next phase of that customer's journey, that implementation managers on that last call and they meet them and they say, this is my colleague. These are some of the customers that they've worked with. They're a rock star. They're gonna carry you through. And I'm gonna join when you go to launch that last call. So it's like, you've gotta not hand the baton off and then let go. You've gotta hand the baton off, but say I'm coming back and I'm gonna stay connected. And you can also do that with just like structure of how you compensate people with upsell and things like that. So to make sure there's an incentive, but I think you've gotta show it. Like you actually have to show up to the call and, and stay engaged. And then additionally, Let's say you're now with a customer, you've launched, you'…

AI assessment note: “You've gotta hand the baton off, but say I'm coming back and I'm gonna stay connected.”

Q dig in one is like the takeaways from the organizations you've worked at, but just the first thing I'm too fascinated by You mentioned your instant love of sales. Do you think sales is something that you instantly fall in love with? Or do you think it's something that you can learn to love over time? Which one do you think is more common amongst the best you've worked with?

A Honestly, I think it's the latter. And I say that even though that wasn't my experience, because I think there's a perception sometimes about sales, that it is just this like kind of robotic, anyone can do it, go and run a script. And there's, there's not a lot of humanity to it. And I think when you really learn, That there's an art and a science to it, that it's about genuine connection with people, that it's about really like listening and actually listening, then I think you can really learn to love it. And I say that because of folks I've seen that I've been super fortunate to partner with and, and, um, coach and mentor come along the way. So it's folks that really have, I've seen them kind of, you know, them, them just blossom into sales when they maybe didn't think they could, you know, they maybe even start as an SDR. They just want to get a job just like me, you know, and they, but they see it and they see the opportunity. I think it's, I think it's actually more the latter, even though my experience was that instant energy.

AI assessment note: “Honestly, I think it's the latter. And I say that even though that wasn't”

Q I love that response. Um, we're going to get into also like flexibility and gaining energy from ambiguity, but the final one I do have to ask is Box. What was the takeaways for Box?

A Um, that was probably a favorite place of mine. And I would say from box lots of learnings, but I would say the one big learning that, that has been kind of core to the way they've run the company from the start is to be an owner. So really believe that we collectively are the company. It isn't someone else. It isn't above you, below you from the sides. It's a, it's, you know, from the way you put your attention into an email, you're sending a prospect to the way you're navigating big, Operational organizational change management. You, you are it. You're a part of it. You're doing it with a team. It's not happening to you. You're help getting it done. And that's really something Aaron just, um, has built and made core to the culture and I've carried it forward, um, in every place I've been since.

AI assessment note: “the one big learning that, that has been kind of core... is to be an owner”

Q You said that building on the success of prior sales interactions and engagements, does that mean that the head of sales should be the one to create it or should founders create it and then pop it off?

A Yeah, good question. I think the founders are the right folks to create it for a few reasons. Um, I mean, there's, there's where it started, right? They had the passion. They had the idea. No one has more passion than them. No one can better articulate the story. So They start from that place of like, this is my belief. This is my idea. This is my baby. So that, that there's that, that you're found grounding from. And what that creates is the person that knows the why and the what in, in such a deep level that they can anticipate things like, um, what problem are we trying to solve? And then when they get that customer feedback pivoting, so like, is that really as important a problem as I thought it would be for the customer? And if it is, or it isn't, How do we change our playbook to amplify how our solution solves that problem? So I think that them being the closest to it allows them to pivot just not only the playbook, but also like feedback back to product, you know? So for example, at work ramp, you know, Ted is a go to market leader and also has an incredible product background. So what's great about that is his, him setting the playbook, which he did here is he knows, he knows how customers respond. He knows what really matters to them and how our story fits in. And then if we get some feedback even now where he's less You know, connected to less, um, as close to the pla…

AI assessment note: “I think the founders are the right folks to create it for a few reasons.”

Q I've got so many questions. One, what are the biggest signs that a sales rep is not working? When are me and you going to sit down and go, oh, no.

A I think it's, um, it's activity. I mean, you, you have to put in the activity. If you're not having enough conversations and you're not working to accelerate the pipeline you have or create the pipeline that you need to have, then what are you doing? So I think you have to go back to pipeline acquisition and pipeline acceleration. What are you doing on both? Most of the time is going to be on acceleration, right? Because the intention is they're not creating all of their own pipeline. But I do think it's very important for sellers to create Some of their own pipeline. They're not fully responsible for it, but they have to have skin in the game on creating pipeline. So I look at these, those two metrics it's acceleration and acquisition and how, and then also how are they, you know, taking feedback? So let's say they have an opportunity that doesn't progress. Let's dissect that. Like, let's do some, you know, post-mortem and then learn in the next one. If you're not seeing that learning pickup, you know, after giving the right coaching and resourcing, then that's a sign to have a conversation.

AI assessment note: “I think it's, um, it's activity.”

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 you should just make sure you're preserving value through what that trade-off is”

Q For those that don't know, what's a QBR and how are the best structured?

A You know, there's argument to do quarterly or monthly, but essentially a regularly scheduled business review with your customer that demonstrates how they are progressing against the goals we originally set. So let's say that is, you're going to launch in our environment and work ramp. You're going to launch a certain number of classes. You're going to build a certain number of guides. You're going to hold this many court, whatever, you know, certifications, whatever it might be. We're going to walk through, how'd you do like how, and how did we, Agree on those and how do we set you up to have that engagement and how did the engagement go? What was the activity from it? How are your users engaged? So really, really use data back to your day, like show them with data, what is happening with their investment and then show them opportunities. Like here's some things that you aren't doing yet. And we have five customers that look just like you that are doing this really well. We want to share that. We think we should try it. Let's get a call on the calendar to talk through how we can do that. So It should be a moment where you're validating the goals of what were originally set, but also really bringing the value of what else can you do? Because it shouldn't just be a checkbox, right? Like, great. You purchased it. You got it launched. Go. What else is happening? How do you, how do…

AI assessment note: “essentially a regularly scheduled business review with your customer that demonstrates how they are progressing”

Q dig in one is like the takeaways from the organizations you've worked at, but just the first thing I'm too fascinated by You mentioned your instant love of sales. Do you think sales is something that you instantly fall in love with? Or do you think it's something that you can learn to love over time? Which one do you think is more common amongst the best you've worked with?

A Honestly, I think it's the latter. And I say that even though that wasn't my experience, because I think there's a perception sometimes about sales, that it is just this like kind of robotic, anyone can do it, go and run a script. And there's, there's not a lot of humanity to it. And I think when you really learn, That there's an art and a science to it, that it's about genuine connection with people, that it's about really like listening and actually listening, then I think you can really learn to love it. And I say that because of folks I've seen that I've been super fortunate to partner with and, and, um, coach and mentor come along the way. So it's folks that really have, I've seen them kind of, you know, them, them just blossom into sales when they maybe didn't think they could, you know, they maybe even start as an SDR. They just want to get a job just like me, you know, and they, but they see it and they see the opportunity. I think it's, I think it's actually more the latter, even though my experience was that instant energy.

AI assessment note: “Honestly, I think it's the latter. And I say that even though that wasn't”

Q Can I ask you, does this change if we're doing an enterprise motion versus a PLG motion?

A Certainly. I think a PLG motion, you know, lends itself to that scale up, right? So you can have volume, you can have velocity, you can have a lot of tries, right? Which is good for just testing messaging. It's good for just trying different sales plays. So I think there's, it's easier to your point to do that with a, you know, PLG stepping into SMB mid-market and beyond versus top down. So I would just say on the enterprise side, um, you know, it's more, there's probably a lot of nuance to what market you're entering. You know, if you're, Going into security, you probably want some folks with, with that, you know, gravitas that can go speak to a CISO and go, you know, have those conversations. But I think there's still an element too, is you can still find some up and comers that can play there as long as they've got a good surrounding support, you know, team around them to help them be successful.

AI assessment note: “Certainly. I think a PLG motion, you know, lends itself to that scale up”

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: “let's just go in with a skeptical mindset and shoot holes in this”

Q of the most incredible companies. I was like, well, how do I kind of compress this in a way where we get the takeaways, um, in an efficient style. And so we're going to go through each company and you're going to tell me a takeaway that's really impacted your mindset. And so if we start with Google, What was the takeaway and how did it impact how you think?

A The real takeaway there is the importance of building like genuine connections to do great work. You can't do anything on your own at Google. It is so big. It's so complex. There's so many layers and crossover of teams and initiatives and budgets and structures that you have to learn quickly that the stakeholder partnerships you make are critical to how you get work done. And so from the start, you've got to get out there and not just stay in your lane. You've got to go learn about the neighboring businesses. You've got to learn about the partnerships that are going to help your business grow and learn about what are their motivations. It's not just about me. I was in Google cloud. What's happening outside of Google cloud. What's parallel to us. How can we work together? And if you do that in a genuine way, you can just, there's so much that you can, you know, take that to that's an applicable, you know, skill and talent that carries over into any role. So that would be my takeaway from Google.

AI assessment note: “The real takeaway there is the importance of building like genuine connections to do great work.”

Q I loved having Aaron on the show. Very, very special person. Now, I want to dive into some of the weeds. Sure, sure. We often hear the term sales playbook. Before we get into, like, whether the founder should be the one to do it or whether someone else should do it, how do you define sales playbook?

A That's a good question. I think it's, you know, a playbook should be a, think of it as a more of a GPS. So it doesn't have to be a script, like each step down to the minute detail. I'll think of it as a guide. So depending on where you are in a sales process where there it's very early and you're doing discovery and trying to get, you know, or even earlier trying to get a meeting and then down to doing discovery and carrying it all the way through, I think a playbook is like, what's the, what's the successful Motion in this stage of the cycle that you should go lean into and flex your strength or get the support around in order to have a successful outcome. So I think it's all about like thinking of it as like drawing on the experience and the success you've seen from previous, from previous sales engagements and building that into like a guide that can help you navigate through, but enough that still gives that level of creativity and flexibility that accounts for the style of that Salesperson, um, depending on whether they're early, whether a leader, whether a directly direct, you know, individual contributor.

AI assessment note: “think of it as a more of a GPS. So it doesn't have”

Q You said that building on the success of prior sales interactions and engagements, does that mean that the head of sales should be the one to create it or should founders create it and then pop it off?

A Yeah, good question. I think the founders are the right folks to create it for a few reasons. Um, I mean, there's, there's where it started, right? They had the passion. They had the idea. No one has more passion than them. No one can better articulate the story. So They start from that place of like, this is my belief. This is my idea. This is my baby. So that, that there's that, that you're found grounding from. And what that creates is the person that knows the why and the what in, in such a deep level that they can anticipate things like, um, what problem are we trying to solve? And then when they get that customer feedback pivoting, so like, is that really as important a problem as I thought it would be for the customer? And if it is, or it isn't, How do we change our playbook to amplify how our solution solves that problem? So I think that them being the closest to it allows them to pivot just not only the playbook, but also like feedback back to product, you know? So for example, at work ramp, you know, Ted is a go to market leader and also has an incredible product background. So what's great about that is his, him setting the playbook, which he did here is he knows, he knows how customers respond. He knows what really matters to them and how our story fits in. And then if we get some feedback even now where he's less You know, connected to less, um, as close to the pla…

AI assessment note: “I think the founders are the right folks to create it for a few reasons.”

Q Okay, so we have, you know, phase one, which is like role knowledge fit. Phase two, which is kind of like data and supporting evidence to suggest quality. What, and what next?

A So I think, you know, if you're gonna go through the steps of having them maybe present to your team or get do some sort of, you know, mock discovery, mock sales call, whatever kind of the, um, you know, case study work that you do. I think that's an important step in the exercise. I don't think it is in like incumbent that it has to be on their current solution or it has to be on yours. I've seen it done both ways. I like putting, um, in front of the candidate about the company they're gonna come join, not because I'm looking for like, The perfect answer, but more I like that they just do go and do homework. Like how are they curious? Like are they, it demonstrates if they're cute, which to me is like a critical characteristic of a great salesperson is curiosity. What they gonna learn about us. What did they find that was interesting that they might find something in our story that we aren't leaning into as much that we should amplify more. So I like to have some sort of case, you know, case study discovery call, whatever it might be, um, that has, that's on the company that they're representing. And so that they can come and kind of tell how they interpret that. And then also how they, you know, that's, that's not an easy, uh, situation to be in also. So it's kind of high stakes. So how do they operate in that? Like, are they comfortable being uncomfortable? Because that's wh…

AI assessment note: “having them maybe present to your team or get do some sort of, you know, mock discovery”

Q Do you have any lessons on title and what people want in title that's important?

A It's honestly like a discovery call in sales. It's like, what's the why behind the title? What are they, are they looking because they want to demonstrate a certain level of progression on their LinkedIn profile? Is it that they want to demonstrate scope? Is it someone who's maybe, and I've seen this like gotten stuck with title at a big company where it, you know, the titles get a little murkier and are a little more flat and they come out and they're like, I need to break out of this, you know, kind of big company title level conundrum that I'm, that I'm trapped in and I want something to demonstrate my scope. So I think it's big. It's a very individual conversation, but I also think it's important to keep in mind, and this is hard to do what you're setting up For will impact the future. So if you get too aggressive on title, then you're a couple of years down the road and your next person comes in and they're like, well, wait, I'm, why am I not a senior director? You know, maybe that first person wasn't, you know? And so you're like, okay, now we got to unwind this a little bit. So I think it's, and it's okay to be comfortable with some of that in the beginning, but I think you just have to be aware of like, all right, this might be something that we have to navigate or walk back a bit as we grow.

AI assessment note: “It's honestly like a discovery call in sales. It's like, what's the why”

Q Okay. So we have that and we mark it as a perfect call. Can I ask what makes an imperfect call on the flip side? It's like, that's what we should look for. Where is it like, this is not a good call.

A This is bad. I think when, um, a salesperson is just going through a script and they're just going through like those, maybe like we, maybe we inform them through enablement. Like here's some great questions that can help guide a call. And instead of asking them and pausing and listening about where that question takes that, They just go to the next question. So it's like, and it's more of just like a checkbox and that perception, you know, it goes back to that perception sometimes with sales of being just a, you know, kind of robotic method. It's like, no, no, you, there's a list and we might give you that to help guide you, but that is not meant to be just something you kind of check, check, check, check, check. Cause what then, what then you're wasting the customer's time and you're wasting your own time. Cause you didn't get anything from that experience.

AI assessment note: “when a salesperson is just going through a script”

Q Is that dead or is that alive, actually?

A I don't think it's fully dead. Um, I mean, it was, it was the play when I started. Like, that was it. You know, you flew out to Texas, you took them to the steakhouse, you did all that stuff, right? I think with COVID and realizing what we can do remote, that is Absolutely change the game with how much selling you can do virtually. And I think if you do that right, and it doesn't feel transactional, you can still have a very genuine connection with a buyer. I think it hasn't died, but I think it's just been kind of, uh, relegated to like a very specific motion that's happening. And it's almost additive. If that makes sense, it's like, you've got to still do all the work to have that moment be really have strong ROI. Um, but, but still, you know, inherently people like getting together and connect So I think there's a lot of goodness to that. It's just like, how do you use that moment? And what's the, what's the return for the customer and for the company?

AI assessment note: “I don't think it's fully dead.”

Q For those that don't know, what's a QBR and how are the best structured?

A You know, there's argument to do quarterly or monthly, but essentially a regularly scheduled business review with your customer that demonstrates how they are progressing against the goals we originally set. So let's say that is, you're going to launch in our environment and work ramp. You're going to launch a certain number of classes. You're going to build a certain number of guides. You're going to hold this many court, whatever, you know, certifications, whatever it might be. We're going to walk through, how'd you do like how, and how did we, Agree on those and how do we set you up to have that engagement and how did the engagement go? What was the activity from it? How are your users engaged? So really, really use data back to your day, like show them with data, what is happening with their investment and then show them opportunities. Like here's some things that you aren't doing yet. And we have five customers that look just like you that are doing this really well. We want to share that. We think we should try it. Let's get a call on the calendar to talk through how we can do that. So It should be a moment where you're validating the goals of what were originally set, but also really bringing the value of what else can you do? Because it shouldn't just be a checkbox, right? Like, great. You purchased it. You got it launched. Go. What else is happening? How do you, how do…

AI assessment note: “essentially a regularly scheduled business review with your customer that demonstrates how they are progressing”

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: “I think what's important is a good deal review is based on a common framework.”

Q I love that response. Um, we're going to get into also like flexibility and gaining energy from ambiguity, but the final one I do have to ask is Box. What was the takeaways for Box?

A Um, that was probably a favorite place of mine. And I would say from box lots of learnings, but I would say the one big learning that, that has been kind of core to the way they've run the company from the start is to be an owner. So really believe that we collectively are the company. It isn't someone else. It isn't above you, below you from the sides. It's a, it's, you know, from the way you put your attention into an email, you're sending a prospect to the way you're navigating big, Operational organizational change management. You, you are it. You're a part of it. You're doing it with a team. It's not happening to you. You're help getting it done. And that's really something Aaron just, um, has built and made core to the culture and I've carried it forward, um, in every place I've been since.

AI assessment note: “the one big learning that, that has been kind of core... is to be an owner.”

Q two, you know, Hunger Games, you know, fight till death and, you know, kill the other one who doesn't, you know, get a million in ARR. Um, I think my point, but he doesn't actually say that that's really unfair of me. Um, but my point is, should we hire more than one at a time or does that actually impact quality of onboarding and the challenge of ramping them?

A Yeah, no, good question. I do. I think you should hire more than, than one at a time for a few reasons. Less about the competition. I think they're, you know, that's kind of going to happen maybe naturally, but it's more about you can work. It's work for scale. I think if you're onboarding one person, it's onboarding, onboard as many as you can, because just that time and investment in onboarding, you know, is a big commitment. So if you're onboarding one, there's huge value in onboarding more. I think there's goodness in creating a team and having, um, a place for those first sellers to collaborate and say, Hey, I'm going to try this message, this motion, the sales play. Maybe let's tune in a bit. You try this. We can test and see what's working. And then you just, you know, you created, uh, that first slight kind of group founding team. There's nothing like it. You know, there's, there's learnings, there's energy, there's culture that comes from that. So there's just so much positive, like by-product from building a team through having, you know, a small group that starts just back to my own experience. You know, I'm still connected to that first team that founded back at remedy. You know, those first sellers are still people I talk to and they have such a bond. So I think there's this Common like we're going to go do this together that you get that carries through and just r…

AI assessment note: “I think you should hire more than, than one at a time for a few reasons.”

Q I've got so many questions. One, what are the biggest signs that a sales rep is not working? When are me and you going to sit down and go, oh, no.

A I think it's, um, it's activity. I mean, you, you have to put in the activity. If you're not having enough conversations and you're not working to accelerate the pipeline you have or create the pipeline that you need to have, then what are you doing? So I think you have to go back to pipeline acquisition and pipeline acceleration. What are you doing on both? Most of the time is going to be on acceleration, right? Because the intention is they're not creating all of their own pipeline. But I do think it's very important for sellers to create Some of their own pipeline. They're not fully responsible for it, but they have to have skin in the game on creating pipeline. So I look at these, those two metrics it's acceleration and acquisition and how, and then also how are they, you know, taking feedback? So let's say they have an opportunity that doesn't progress. Let's dissect that. Like, let's do some, you know, post-mortem and then learn in the next one. If you're not seeing that learning pickup, you know, after giving the right coaching and resourcing, then that's a sign to have a conversation.

AI assessment note: “I think it's, um, it's activity.”

Q Do you think you can anticipate churn ahead of time?

A Yeah. You've got to look for signals. And then some of it is subjective, of course, because anticipation is going to come from a customer success manager connecting with a customer and like reading that experience and figuring out what does that mean? But I think you can measure a customer's health throughout of, you know, let's say a quarterly fiscal, whatever the timeframe is. And that can be with data and usage, but it also can be like, Hey, we set up these milestone calls. We're gonna have these calls to make sure we're progressing. Let's say they miss the calls. Let's say they continue to put like back to your question. It keeps getting pushed. Why is it getting pushed? We're not on the priority. Take that information, marry it with the customer data. If both are down, that's a signal that you could be stepping into an area of risk. So I, I definitely think you can do, you can do, you know, basically measure the health score of, of a customer and using both data and anecdotal experience and seeing like, what does that tell us? And then how do we get ahead of it? Okay. So let's say they're not attending calls. Does a leader in the customer success or revenue organization need to step in and say, Hey, I understand, you know, these were your original goals. We're excited to really continue to work with you. We'd really like to get a call. We've understand there's been some ch…

AI assessment note: “Yeah. You've got to look for signals. And then some of it is subjective”

Q Now I always love to start with some context. So tell me, how did you make your way into the world of sales and come to lead some of the most incredible sales orgs as you have done?

A Oh, thank you. Um, great question. I discovered sales at the ripe age of 15 and a half, um, which was the day I got a worker's permit and could get a job. So I was fired up to get a job and make some money. I applied for a few retail jobs in my hometown and the owner of two kind of neighboring boutiques met me and said, you're hired start tomorrow. So, so excited. So I march in on my first day, ready to get working. And he said, here are the keys to the other store. Uh, go open it up. Um, there's a shoe box of cash in the back. Use that for the cash register. I'll show up in a few hours and teach you what to do. And I was terrified. So he's like, open the store and get going. So I like, all right, I'm going to do this. I go and open the store and soon after opening the door, customer started coming in. So I had to start selling. I did a terrible job. Um, I don't think I charged sales tax to anyone that day. I'm sure there were some very good deals made, but what I got from it was the energy of working with customers, like how fun that is, how energizing that is. Um, it's a thrill of partnering with someone, even, even in the retail capacity in a small boutique. So I got energized by it and I stayed in retail throughout high school and college. Um, and then fast forward, I graduated from college during the recession in the early nineties. So Not a lot of jobs. I was still workin…

AI assessment note: “I discovered sales at the ripe age of 15 and a half”

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: “incentivize when that opportunity goes to the next stage”

Q Okay, so we have, you know, phase one, which is like role knowledge fit. Phase two, which is kind of like data and supporting evidence to suggest quality. What, and what next?

A So I think, you know, if you're gonna go through the steps of having them maybe present to your team or get do some sort of, you know, mock discovery, mock sales call, whatever kind of the, um, you know, case study work that you do. I think that's an important step in the exercise. I don't think it is in like incumbent that it has to be on their current solution or it has to be on yours. I've seen it done both ways. I like putting, um, in front of the candidate about the company they're gonna come join, not because I'm looking for like, The perfect answer, but more I like that they just do go and do homework. Like how are they curious? Like are they, it demonstrates if they're cute, which to me is like a critical characteristic of a great salesperson is curiosity. What they gonna learn about us. What did they find that was interesting that they might find something in our story that we aren't leaning into as much that we should amplify more. So I like to have some sort of case, you know, case study discovery call, whatever it might be, um, that has, that's on the company that they're representing. And so that they can come and kind of tell how they interpret that. And then also how they, you know, that's, that's not an easy, uh, situation to be in also. So it's kind of high stakes. So how do they operate in that? Like, are they comfortable being uncomfortable? Because that's wh…

AI assessment note: “having them maybe present to your team or get do some sort of, you know, mock discovery”

Q Do you have any lessons on title and what people want in title that's important?

A It's honestly like a discovery call in sales. It's like, what's the why behind the title? What are they, are they looking because they want to demonstrate a certain level of progression on their LinkedIn profile? Is it that they want to demonstrate scope? Is it someone who's maybe, and I've seen this like gotten stuck with title at a big company where it, you know, the titles get a little murkier and are a little more flat and they come out and they're like, I need to break out of this, you know, kind of big company title level conundrum that I'm, that I'm trapped in and I want something to demonstrate my scope. So I think it's big. It's a very individual conversation, but I also think it's important to keep in mind, and this is hard to do what you're setting up For will impact the future. So if you get too aggressive on title, then you're a couple of years down the road and your next person comes in and they're like, well, wait, I'm, why am I not a senior director? You know, maybe that first person wasn't, you know? And so you're like, okay, now we got to unwind this a little bit. So I think it's, and it's okay to be comfortable with some of that in the beginning, but I think you just have to be aware of like, all right, this might be something that we have to navigate or walk back a bit as we grow.

AI assessment note: “what's the why behind the title? What are they, are they looking because”