The Exchanges

Q I don't understand why it's, why it's harder. Like product marketing is easier. Word of mouth is quicker. Um, product resonance is better. Your understanding of the customer's better deal. Why is it slower?

A So I, I wouldn't say it's slower and I'm a violent proponent of verticals. I think folks would just say it's more expensive because I can't take a banking expert and put them into healthcare. And there's not as much abilities that are designated hitters or can play every position on the field. Like your CSM team has to understand it. Your SE team has to understand it. Your AE team has to. So there is an added investment there. Plus you're specializing your messaging versus if you have a broad based message that applies to everybody, it's a little bit easier from a product marketing perspective, but I violently agree with you. I think when I look at the CROs I talked to, those that have sound vertical strategies are the ones that are feeling The least amount of pain throughout this macro climate, because I think they have it nailed and I think those with vertical approaches are actually winning right now.

AI assessment note: “I wouldn't say it's slower and I'm a violent proponent of verticals.”

Q One thing I've noticed that really increases speed is much tighter product marketing and verticalization. You're able to build a brand in a much tighter community. Can you help me out? What are some of your biggest lessons in terms of building vertical teams?

A When it comes to product marketing and messaging, and I think Salesforce is The absolute master at this. If I talk about bits and bytes and features and functions that aren't relative to your individual problem, like you're going to lose. So I think for us, right? Like when we talk to med device companies, we show up and talk about forecasting the way of create, convert, close, and churn. And they're like, we're a consumable company. So we had to relearn how to actually talk to med device companies and really understand like, oh, okay. Like you're not forecasting in the way that we are in terms of true B to B opportunities. You're actually forecasting in how many syringes or how many, whatever they're going to go through on a daily basis. How do we reframe this and help you track that in a more accurate way? So Extremely long way of saying, talk the language of your client, understand their unique problems, and how you can uniquely solve them, and sometimes you can't, right? And I think for earlier stage companies, a little bit is, yeah, it's always fun to go after the JPMCs, the Bank of the Morrigans, the biggest banks in the world, but sometimes you're not a good fit. So play where you fit well, um, and that's been a, I think, a big thing I've learned through the last three stops.

AI assessment note: “talk the language of your client, understand their unique problems”

Q What levers are you most willing to move on and compromise on?

A Without giving too many secrets about how to negotiate with Clary on the most popular sales podcast. Um, I look, I think the thing that we care the most about, of course, is number of users. So the bigger the population, the better the price you're going to get. And that is true for every named user Your company, same thing on consumption. The more you're going to commit to, the better rate you're going to get. Next for us is service start date. So how quickly can you get them? SaaS companies can't recognize that until they actually activate users. Um, meaning if you're going to activate six months from now, I'm not taking it until Q four. Q two deals are worth a lot more money to me in that sense. And then the third thing is like length of the contract. Fourth thing is always probably terms and conditions of simple things, payment terms, whatever it may be, and creativity. Creativity around T's and C's.

AI assessment note: “number of users... service start date... length of the contract... terms and conditions”

Q Ok, what about pricing? Like, how often, how do you think about discounting? A lot of sales leaders, it's so interesting, some weaponize it, and some are like, no.

A Like, a lot depends on the maturity of your sales team. You have to have guidelines in place just for safeguards and governance to not do anything silly, but I truly do, and I've told my, my sellers at the last three companies I've been to is like, you own pricing. If you come to me and help explain why this is important for the client's success and why it's going to make them successful, Within staying with reasonable guide rails, we're going to give you the pricing you need. Um, and I, I think that's ever true now where we look at macro economic environment, SAS going in the tank, like we got to be focused on adoption and long-term success. And there are times when people talk about creative deal construction, like, yeah, we've done crazy ramps to get people off the ground because they were tight, but we knew it was going to be a long-term contract and was going to help them. We've done unnatural things. If we know enough, And the client is willing to share what their constraints are. We can always find a way to solve it.

AI assessment note: “I've told my sellers at the last three companies I've been to... you own pricing.”

Q You close it. We, we do the close three, and then we think about four churn. And often it's because I close Ben and then I throw you over to, you know, whatever, uh, on CS and it's like a terrible handoff. How do we think about creating great interplay between sales and CS to make sure implementation adoption is great?

A Back to your earlier question. A lot of it has, has to do with selling the right way. So if you're selling the right way and looking at the deal construction, looking at when someone wants to be live, truly understanding the process rather than just saying, here's a sexy widget, buy it, but you've mapped out their journey based on business impact and complexity to implement. You understand upfront in pre-sales, like what they're going to do and what they need to do. It's a hell of a lot easier to hand that blueprint over to customer success. And have them pick it up. Like they've been along for the ride the whole time. Then if it is, Hey, Harry, I have this great product. That's going to solve all these issues, but we don't actually do a thorough sale. That's never going to work in general, regardless of how great your CS team is. Like you have to have a very thorough and outcome based sale, I guess, from the beginning to make sure that your customer success team is set up for success.

AI assessment note: “It's a hell of a lot easier to hand that blueprint over to customer success.”

Q Are you seeing buying new tech much less? Like people talk about CFOs, tightening budgets, centralizing. Are you seeing that?

A It's funny. So most of the CFOs I talked to are like, we're spending the same. We're just spending it on different things. Um, and I think that one, that means there's enterprise tech consolidation. So they're trying to say, Hey, I can do as much with one platform as much as humanly possible. I don't need 12 best of breed products. Two, I think you're seeing folks dabble obviously with Gen AI and we got to mention it 10 times on every podcast we're on, right? But, um, you're seeing people shift money there and spend more money there and that, that does get exceptionally expensive in certain spots. But I don't, I don't think folks are buying less. I think they're just buying differently. And from what I've seen, it's been more platform based approach and it's been more platforms that have proven success rather than just the shiny object. So if you can show material improvement on an ROI of bottom line, you know, constriction, top line growth, whatever it may be, folks are interested, but if you're just there because you're a shiny object, yeah, you're getting cut.

AI assessment note: “I don't think folks are buying less. I think they're just buying differently.”

Q What levers are you most willing to move on and compromise on?

A Without giving too many secrets about how to negotiate with Clary on the most popular sales podcast. Um, I look, I think the thing that we care the most about, of course, is number of users. So the bigger the population, the better the price you're going to get. And that is true for every named user Your company, same thing on consumption. The more you're going to commit to, the better rate you're going to get. Next for us is service start date. So how quickly can you get them? SaaS companies can't recognize that until they actually activate users. Um, meaning if you're going to activate six months from now, I'm not taking it until Q four. Q two deals are worth a lot more money to me in that sense. And then the third thing is like length of the contract. Fourth thing is always probably terms and conditions of simple things, payment terms, whatever it may be, and creativity. Creativity around T's and C's.

AI assessment note: “I think the thing that we care the most about, of course, is number of users.”

Q Ok, what about pricing? Like, how often, how do you think about discounting? A lot of sales leaders, it's so interesting, some weaponize it, and some are like, no.

A Like, a lot depends on the maturity of your sales team. You have to have guidelines in place just for safeguards and governance to not do anything silly, but I truly do, and I've told my, my sellers at the last three companies I've been to is like, you own pricing. If you come to me and help explain why this is important for the client's success and why it's going to make them successful, Within staying with reasonable guide rails, we're going to give you the pricing you need. Um, and I, I think that's ever true now where we look at macro economic environment, SAS going in the tank, like we got to be focused on adoption and long-term success. And there are times when people talk about creative deal construction, like, yeah, we've done crazy ramps to get people off the ground because they were tight, but we knew it was going to be a long-term contract and was going to help them. We've done unnatural things. If we know enough, And the client is willing to share what their constraints are. We can always find a way to solve it.

AI assessment note: “You have to have guidelines in place just for safeguards... you own pricing.”

Q You close it. We, we do the close three, and then we think about four churn. And often it's because I close Ben and then I throw you over to, you know, whatever, uh, on CS and it's like a terrible handoff. How do we think about creating great interplay between sales and CS to make sure implementation adoption is great?

A Back to your earlier question. A lot of it has, has to do with selling the right way. So if you're selling the right way and looking at the deal construction, looking at when someone wants to be live, truly understanding the process rather than just saying, here's a sexy widget, buy it, but you've mapped out their journey based on business impact and complexity to implement. You understand upfront in pre-sales, like what they're going to do and what they need to do. It's a hell of a lot easier to hand that blueprint over to customer success. And have them pick it up. Like they've been along for the ride the whole time. Then if it is, Hey, Harry, I have this great product. That's going to solve all these issues, but we don't actually do a thorough sale. That's never going to work in general, regardless of how great your CS team is. Like you have to have a very thorough and outcome based sale, I guess, from the beginning to make sure that your customer success team is set up for success.

AI assessment note: “easier to hand that blueprint over to customer success. And have them pick it up.”

Q I am fascinated. I had so many Great strengths that you have. And one of them was kind of teasing out from customers what they want. And also, as you said, getting them to see your point of view and convincing them. What are the biggest lessons in getting customers to see your points of view? What questions do you ask? What works? What doesn't? How do you approach that?

A The majority of organizations I've gone, I've been a part of, like have been on the maturity cycle where a lot of tech companies become as product sellers. They talk about me, me, me, me. Here's all the great features and functions. Here's the bits and bytes. I think the first thing in terms of like, not that you're convincing someone to see their point of view, you're showing up with an opinion, right? It's the same thing as if I go to my boss, I can't say, Hey, I have a problem, right? It's more, I have a problem and here's an idea I have to fix it. Right. And the same way when you're talking to a client, I think what we teach a lot of our sellers is really study their business. It's the easiest thing that you can do, and if you show up with a strong opinion of, hey, I've talked to your team, both qualitative, quantitative research that says, here's my perspective on where you should be going, and here's how I uniquely help you get there, you may not always win, but you have a disproportional chance that you're going to actually have a seat at the table to help that person solve their business, and candidly, like, I don't want to buy, and I buy enough software from people that don't know my business inside and out, and don't have a unique way to solve the problems I have, like, we're not in an era anymore of just buying tech For tech sake. So that's what I think about that wh…

AI assessment note: “really study their business... and if you show up with a strong opinion”

Q said was a superpower of yours was creativity when it comes to deal construction. And I want to get it right. They said, when it comes to deal construction, you're one of the best in the world, uh, taking the go to market team on the journey with him. As we work to cultivate this muscle, what makes you so good at deal construction and what is good deal construction?

A I don't know who taught me this, and I think I had a lot of great mentors probably at Salesforce that, that leaned into this, where a lot of times they, like, um, one of my first great bosses for a long, long time, Eric Eiken-Siders, where he was like, you own pricing. I'm like, no, I don't. Like, I have to go through all the approvals. I have to ask for this person and this person to approve. You ultimately get to prove it. He's like, no, you own pricing. So, what was ingrained to me early on was my job as a seller is to understand the client's constraints as it relates to their OPEX, CAPEX, cash flow, whatever it may be, and the constraints that they have, which often is tough to figure out, because sometimes it's, yes, the buyer knows it, but sometimes the procurement knows it. More often than not, it's a finance person that you never talk to, but if you can figure out through options and through the right questions what constraints they have, and then you really understand The levers you have internally. The superpower has been with a lot of training from a lot of great mentors over the time. Like how do you thread that needle of your constraints, their constraints and find a win-win situation. But a lot of times I think folks just say, here's my pricing. Here's my price per like discount percentage. Do you want to buy versus truly understanding budgets as it relates to ope…

AI assessment note: “how do you thread that needle of your constraints, their constraints and find a win-win”

Q I always think it's a hard one, because it's like, Ben, can you introduce me to your wider team? Because you might not be here, you might get hit by a bus or leave, in which case, I want to close this deal.

A Yeah, and I think, so, when I was a seller, I think I did this with trying to fourth wall folks from the human element of, you know I'm a salesperson, you know it's my job, and you know that, like, which is great about my current job, like, I sell to sellers, so it's super easy for me to say to the CRO, like, You've been in my shoes. You know, I got to talk to the CFO as well, and I got to make sure that I understand his or her constraints to figure this out. I think I did the same thing as a salesperson. A lot of times was just trying to make it a human element. If you come off in full salesperson cheese and say, Harry, I really make up some bullshit reason as to why you need to get to so-and-so they're going to smell right through it. And honestly, authenticity is the one thing that matters there. So I think what I always did was like, Candidly, I'm a salesperson, and you know it's my job to triangulate on this, so I don't waste my team's time, and I don't waste your team's time. Can I have an introduction to X, Y, or Z? Nine times out of 10 it worked.

AI assessment note: “Candidly, I'm a salesperson, and you know it's my job to triangulate”

Q Are you seeing buying new tech much less? Like people talk about CFOs, tightening budgets, centralizing. Are you seeing that?

A It's funny. So most of the CFOs I talked to are like, we're spending the same. We're just spending it on different things. Um, and I think that one, that means there's enterprise tech consolidation. So they're trying to say, Hey, I can do as much with one platform as much as humanly possible. I don't need 12 best of breed products. Two, I think you're seeing folks dabble obviously with Gen AI and we got to mention it 10 times on every podcast we're on, right? But, um, you're seeing people shift money there and spend more money there and that, that does get exceptionally expensive in certain spots. But I don't, I don't think folks are buying less. I think they're just buying differently. And from what I've seen, it's been more platform based approach and it's been more platforms that have proven success rather than just the shiny object. So if you can show material improvement on an ROI of bottom line, you know, constriction, top line growth, whatever it may be, folks are interested, but if you're just there because you're a shiny object, yeah, you're getting cut.

AI assessment note: “most of the CFOs I talked to are like, we're spending the same.”

Q How do you advise founders on leveraging the team to work more together to close a deal? What do you do in those cases? Is it ever like, Ben, you went to, you know, Wisconsin, this guy's a Wisconsin guy, like, come in on this call, talk about Scani, and just build that rapport so it's a little bit more natural. Is that it?

A I actually don't, so I think it's really hard to get a team to work together well on a deal that isn't a good team to begin with. So I think about this more from, and this may be too ethereal, but I think about it more of like, hopefully you've built great cross-functional relationships, and my job as a CRO to be tight with product, tight with marketing, tight with the CEO, and have those open and honest relationships, so it isn't, hey, this is what I need specifically for this deal for Harry. It is more a natural thing that always happens of, hey, this one might need a product roadmap, this one might need some marketing love, this one might need whatever, like, It's been, if you don't have that trust in that foundation set up up front, it's really hard, and it's really obvious, and there's the jokes we've all made of when certain sales teams show up with 16 people in the room, it's because they don't work as a freaking team, right? And those that do can show up with three and say, yeah, we got each other's backs, and we can interchange roles. Um, so I think I'd take it back a step further of, like, I think my job as a CRO is to kind of be the glue for the company, for the customer-facing efforts, to make sure we are one unified front.

AI assessment note: “I actually don't, so I think it's really hard to get a team to work together”

Q Convert, right? Um, convert. I have so many where I'm on the board of, and they're like, yeah, you know, honestly, they just said it slipped to next quarter. They love us. They love us, Ben, but it just slipped to next quarter. How do you respond when someone in your team says that?

A I, hopefully, at that point, you've gone through, like, who's the decision maker? What is their decision criteria, right? What, what was the compelling event? Is this budget and funded? The traditional med pick questions, and you'll know pretty quick digging into one Quick one-on-one with a seller, like, if they actually did their homework, or if they just trusted their champion, and they do have a great relationship, but they didn't actually help them sell internally. I think there's a reason all these sales methodologies, like, exist. It's because if you do the homework, nine times out of 10, it does work, and I think a lot of it is just doing the right research and asking the right questions.

AI assessment note: “you'll know pretty quick digging into one Quick one-on-one with a seller”

Q What do you think startups get most wrong as they try and scale from smaller to larger enterprise accounts?

A I think it's a big bet, right? And at Clary, we looked at enterprise versus commercial, and I think we said, hey, we have the most sophisticated forecasting tool, so we should move more capacity into the enterprise. But it was a big strategic decision at the board level. I think a lot of folks go to enterprise cause they say, Hey, there's more money there. Right. And that's always true. But I think you have to find your product niche and what like the unique problems your customers have and how your product solves it is where I would spend and put my chips. And I have founder friends that are saying like, we don't, we want to be gen AI for very small startups. We don't want to deal with the biggest companies in the world cause we can't build the capacity that they have. And I think that's a very intelligent decision.

AI assessment note: “a lot of folks go to enterprise cause they say, Hey, there's more money there.”

Q I don't understand why it's, why it's harder. Like product marketing is easier. Word of mouth is quicker. Um, product resonance is better. Your understanding of the customer's better deal. Why is it slower?

A So I, I wouldn't say it's slower and I'm a violent proponent of verticals. I think folks would just say it's more expensive because I can't take a banking expert and put them into healthcare. And there's not as much abilities that are designated hitters or can play every position on the field. Like your CSM team has to understand it. Your SE team has to understand it. Your AE team has to. So there is an added investment there. Plus you're specializing your messaging versus if you have a broad based message that applies to everybody, it's a little bit easier from a product marketing perspective, but I violently agree with you. I think when I look at the CROs I talked to, those that have sound vertical strategies are the ones that are feeling The least amount of pain throughout this macro climate, because I think they have it nailed and I think those with vertical approaches are actually winning right now.

AI assessment note: “So I, I wouldn't say it's slower and I'm a violent proponent of verticals.”

Q said was a superpower of yours was creativity when it comes to deal construction. And I want to get it right. They said, when it comes to deal construction, you're one of the best in the world, uh, taking the go to market team on the journey with him. As we work to cultivate this muscle, what makes you so good at deal construction and what is good deal construction?

A I don't know who taught me this, and I think I had a lot of great mentors probably at Salesforce that, that leaned into this, where a lot of times they, like, um, one of my first great bosses for a long, long time, Eric Eiken-Siders, where he was like, you own pricing. I'm like, no, I don't. Like, I have to go through all the approvals. I have to ask for this person and this person to approve. You ultimately get to prove it. He's like, no, you own pricing. So, what was ingrained to me early on was my job as a seller is to understand the client's constraints as it relates to their OPEX, CAPEX, cash flow, whatever it may be, and the constraints that they have, which often is tough to figure out, because sometimes it's, yes, the buyer knows it, but sometimes the procurement knows it. More often than not, it's a finance person that you never talk to, but if you can figure out through options and through the right questions what constraints they have, and then you really understand The levers you have internally. The superpower has been with a lot of training from a lot of great mentors over the time. Like how do you thread that needle of your constraints, their constraints and find a win-win situation. But a lot of times I think folks just say, here's my pricing. Here's my price per like discount percentage. Do you want to buy versus truly understanding budgets as it relates to ope…

AI assessment note: “how do you thread that needle of your constraints, their constraints and find a win-win”

Q I always think it's a hard one, because it's like, Ben, can you introduce me to your wider team? Because you might not be here, you might get hit by a bus or leave, in which case, I want to close this deal.

A Yeah, and I think, so, when I was a seller, I think I did this with trying to fourth wall folks from the human element of, you know I'm a salesperson, you know it's my job, and you know that, like, which is great about my current job, like, I sell to sellers, so it's super easy for me to say to the CRO, like, You've been in my shoes. You know, I got to talk to the CFO as well, and I got to make sure that I understand his or her constraints to figure this out. I think I did the same thing as a salesperson. A lot of times was just trying to make it a human element. If you come off in full salesperson cheese and say, Harry, I really make up some bullshit reason as to why you need to get to so-and-so they're going to smell right through it. And honestly, authenticity is the one thing that matters there. So I think what I always did was like, Candidly, I'm a salesperson, and you know it's my job to triangulate on this, so I don't waste my team's time, and I don't waste your team's time. Can I have an introduction to X, Y, or Z? Nine times out of 10 it worked.

AI assessment note: “Can I have an introduction to X, Y, or Z? Nine times out of 10”

Q So Stevie, the CR at Banta, is also in 20 Tales, and so I work with her closely, and she always says that actually you can stress test moving into enterprise more reasonably or without such investment than people think. Can you kind of dip your toe into an enterprise motion without having it be a big company-wide bet?

A Yes, I think you can, and sorry, what I meant is if you're shifting your capacity to enterprise, like, you better be very, very sure of it. But a thousand percent, I think the more, even the biggest tech companies in the world, when they're calling on the other biggest tech companies in the world, like you're going to have different requirements. They are a special snowflake. You're going to have to invest R and D dollars, which most startups and most earlier stage companies don't have the capacity to do on the development side. So I think to her point, it's a great one. If you test it with, Hey, I'm going to go after name, big company, X, Y, or Z. And if it requires a huge shift in my roadmap, you're going to have to give up stuff that you were planning on developing, which I think is the hardest part for earlier stage companies.

AI assessment note: “Yes, I think you can, and sorry, what I meant is”

Q But like, are leaders wrong to push for more? When you, Ben, say, hey, 1.2, am I wrong to say, come on, Ben, we can do 1.4?

A I think the best leaders don't tell them stories or believe the stories that they tell. Because great salespeople are storytellers of this is, every QBR, I'll put it this way, every QBR I've ever been to, every AE puts up a slide that says, here's me finishing at 120% to plan. Every time. It's magical. Now, do a hundred percent of AEs finish at a 120% plan? Never. Right? So I think the, the, the best sales leaders I've been around and the people that I've learned the most from is, yes, you push them to tell more, but you're really realistic and honest on the state of the business. And that requires kind of the 13 week process to make sure that you're checking and understanding where the holes in your business are.

AI assessment note: “yes, you push them to tell more, but you're really realistic and honest”

Q Final element. We get to the comp plan. We're like, yeah, we want to put Ben in the team. What are the biggest lessons on creating a comp package that's compelling for sales reps?

A I think where we've looked at this and an example from Clary, like we had hunter farmer sellers. So I think the best, and then we moved to a hybrid for the enterprise team, meaning they had both install base and that new logos. I think so often comp plans are designed, designed after the fact. I think the only big lesson that I'd have is like, you need to decide your go-to-market strategy. And yes, that's going to have inputs from finance on margin, like on margin targets, profit targets, growth targets, all of those things. Design your sales alignment, design your sales motion, and then the comp plan should come after that to reinforce those things. Too often it's backed into of like, well, this is what we did last year. Let's make a small tweak versus holistically taking a step back and looking at the overall go to market strategy, alignment, motion, talent, and what you're trying to drive and use those design principles to design the comp plan.

AI assessment note: “the comp plan should come after that to reinforce those things”

Q is your business. How the fuck do you forecast accurately in a world where traditionally, like, the joy of SaaS was like, you know, you had your, kind of, everyone stayed, and you added 20%, and it was a great business, but now the accuracy of forecasting is so hard. For me as a founder, how do you advise me on how to forecast accurately in a time of volatility?

A I think three things. One, how do you drive the most simplistic process of I, I tell people all the time, salespeople aren't lazy. They just are wired to find the quickest path from point A to point B. So you have to make it super simple, super straightforward. I think the second and third thing that I've learned a lot about being in my seat now is the process really matters. So there's a lot of forecast calls and I get to meet with a lot of CROs and I'm fortunate enough in that situation, like forecast calls you listen to and they're like, Hey, this deal's still good. And we're like, yep, that's their forecast call versus I think where we looked at this at UI path. And then again, at Clary was how do I drive a 13 week revenue cadence for the quarter that I'm going to actually chunk up into different Like four segments. So one example of this would be like week one, we're all looking at the same data that says, Hey, here's my slip deal reviews. Here's my deal back walk up. Here's my commits. And the reason you're doing that. So everybody's looking at the same page is just so that frontline managers are all asking the same questions. AEs all know what to expect. And then as a senior leader, you have the opportunity to, to manage by exception to say, where do I have a hole in the business? Is it top of funnel? Is it conversion? Is it execution? Or is it churn and retention? And t…

AI assessment note: “how do I drive a 13 week revenue cadence for the quarter”

Q It is amazing to be as granular as this, because so many founders will literally be pausing and taking notes on it. And so my question to you is like, is it one, like, should we go through week two now? Or are there elements where you're like, this is a core milestone point. This is a core milestone point. Focus on those.

A For me, we chunk it into Four chunks. So what we did is actually, and, uh, my SVP of RevOps, Scott Pizer, he helped kind of document all this and we realized it was to tighten up our own forecast cadence. And then we're like, holy cow, we're onto something and clients should be able to have access to this too. So a lot of times we're giving it to them or we're just mapping back based on their individual business needs or revenue objectives. The way I think about it is based on the individual week and there's different widgets or different pieces of the dashboard, but it's, you're looking at four different aspects of the business. So one, and I, We'll use a cheesy alliteration, um, to make it easier to follow, but we think about it as like create, convert, close, and churn. Those are the four buckets, and depending on the week, you're going deeper or less deep into each of them. So you can imagine in week one, like we just talked about, create is kind of the most important piece of this, of looking at pipe gen efforts. Do I have enough pipe coverage? All the things we talked about, but like the last piece of it is, what's my pipe coverage? What's my historical? Pipe coverage. What's my historical, um, pipe by stage, year to date, or excuse me, same time, last quarter, same time, last quarter, last year. Those types of things where you're really trying to understand the help of y…

AI assessment note: “we think about it as like create, convert, close, and churn.”

Q What skill that you're slightly cautious to admit has been the biggest contributor to your success?

A I think one earlier on in my career was the fear of failure, for sure. Like, I was very much motivated to say, I can't lose at anything, and I'm gonna do, I'm gonna outwork, out hustle, do everything within my power to make sure I don't lose, and that was one, I was talking to someone, actually our CEO the other day about this, of like, on a bike, if you try to pass me on a bike, when I was 3010 years ago, I would throw up trying to pass you. Like I would just, I couldn't let it happen. I was that competitive in everything I did or ping pong or silly things. And I think that was a big thing for a while. I think for me, another one, and there's a motivation there that's like a competitive drive. And then the second piece I think is like, I don't want to let people down. I think one that's hopefully made me be a great or decent people leader, I should say. Um, but also like the impact you're going to hopefully have with clients. If you think that lens of like, I want to make sure they walk away from this in a healthy spot, um, is another thing that I'm somewhat embarrassed to make. Cause I don't want to be like a people pleaser. I don't want to be that person and say that I'm like so insecure that I'm always worried about how people think about me. But I think a lot of times it is, um, I really, really don't want to let people down, and I want them leaving with a great taste in t…

AI assessment note: “one earlier on in my career was the fear of failure, for sure.”

Q What skill that you're slightly cautious to admit has been the biggest contributor to your success?

A I think one earlier on in my career was the fear of failure, for sure. Like, I was very much motivated to say, I can't lose at anything, and I'm gonna do, I'm gonna outwork, out hustle, do everything within my power to make sure I don't lose, and that was one, I was talking to someone, actually our CEO the other day about this, of like, on a bike, if you try to pass me on a bike, when I was 3010 years ago, I would throw up trying to pass you. Like I would just, I couldn't let it happen. I was that competitive in everything I did or ping pong or silly things. And I think that was a big thing for a while. I think for me, another one, and there's a motivation there that's like a competitive drive. And then the second piece I think is like, I don't want to let people down. I think one that's hopefully made me be a great or decent people leader, I should say. Um, but also like the impact you're going to hopefully have with clients. If you think that lens of like, I want to make sure they walk away from this in a healthy spot, um, is another thing that I'm somewhat embarrassed to make. Cause I don't want to be like a people pleaser. I don't want to be that person and say that I'm like so insecure that I'm always worried about how people think about me. But I think a lot of times it is, um, I really, really don't want to let people down, and I want them leaving with a great taste in t…

AI assessment note: “I think one earlier on in my career was the fear of failure”

Q Then we just put more CSMs on it. We give them more love. What do we do?

A I think you're underst... Standing the risk in week one for us. Yes. Eventually you're likely swarming around it, but I think for me, it's as simple as, Hey, let me look a quarter ahead. Do we have any glaring mistakes? And it's probably five percent of the forecast call, but holy cow, it's a new quarter. Let's start a new, let's get a sprint call related to this or a big deal review or whatever you want to call it to get the team on the horn. Cause one of our top 10 renewals is at risk and let's deal with it now instead of 90 days from now. So that's probably the step on that. And then step four is Basic of like, let me look at my overall pipe coverage. And you're looking at that based on historical conversion rates from various stages. And that's where I think from us, our tooling comes in more to say, Hey, the predictive forecasting, the ML is going to tell you, you're going to land at this based on where the pipe gen or the pipeline sits today across early stage, mid stage, late stage. And once you have those four things, like that's week one and we can go through the whole thing, but that it later just turns into more of like, How do you then look at conversion of pipeline? And then in the last couple of weeks, of course, it's just purely execution of, are we doing the right things to make sure we're moving the needle in as. Shortest timeframe as possible.

AI assessment note: “let's get a sprint call related to this or a big deal review”

Q How do you invest more in a marriage? That's like date night? What does that mean?

A Yeah, no, I think it, look, like, you think about this, if, how many CROs I talk to, if they're, if their CEO called, they immediately would be like, Harry, hang on 1:02, I gotta take this. If your wife calls, how many people do I know that do that? Very few in certain high power positions. So I think it's one thing of like, be honest with yourself of where your priorities are at and actually put the parameters in place to make sure you're prioritizing your spouse, your kids, your partner, whatever it may be. And I think put the same effort into it. Um, the same way where a lot of times, like I think I was on the road, you know, you're on the road for two straight weeks. You get home Friday night. The first thing you want to do is have a glass of wine and just sink into the couch. You got to show up the same way you did for the client at eight AM as you did for your kids at six PM. And I think that's probably a lesson that I've had in the last five years. And it took me a long time to, to make sure that I was putting as much effort into my personal life as I was my professional life.

AI assessment note: “show up the same way you did for the client at eight AM”

Q I am fascinated. I had so many Great strengths that you have. And one of them was kind of teasing out from customers what they want. And also, as you said, getting them to see your point of view and convincing them. What are the biggest lessons in getting customers to see your points of view? What questions do you ask? What works? What doesn't? How do you approach that?

A The majority of organizations I've gone, I've been a part of, like have been on the maturity cycle where a lot of tech companies become as product sellers. They talk about me, me, me, me. Here's all the great features and functions. Here's the bits and bytes. I think the first thing in terms of like, not that you're convincing someone to see their point of view, you're showing up with an opinion, right? It's the same thing as if I go to my boss, I can't say, Hey, I have a problem, right? It's more, I have a problem and here's an idea I have to fix it. Right. And the same way when you're talking to a client, I think what we teach a lot of our sellers is really study their business. It's the easiest thing that you can do, and if you show up with a strong opinion of, hey, I've talked to your team, both qualitative, quantitative research that says, here's my perspective on where you should be going, and here's how I uniquely help you get there, you may not always win, but you have a disproportional chance that you're going to actually have a seat at the table to help that person solve their business, and candidly, like, I don't want to buy, and I buy enough software from people that don't know my business inside and out, and don't have a unique way to solve the problems I have, like, we're not in an era anymore of just buying tech For tech sake. So that's what I think about that wh…

AI assessment note: “study their business... show up with an executive point of view”

Q What tools and processes do you use in the convert phase to move deals down pipe?

A Clary for me as a forecasting platform is as a CRO, you have a gun to your head every day. You don't have enough hours in the time, and as a founder, you feel the same way. So all I need is give me the signal to where the gap in my business is. And a lot of times it's on the career or on the convert side to your point. So if I then go into the convert, I can look at call recordings. I can look at sales engagement. I can look at med pick questions. I can dig into the deal review to say, Hey, these ones are stalled or at risk. Cause hopefully Claire is saying, look, these are the five that are not going to close. And then I know where to go. And then your job as a sales leader is pretty natural. I think for most people to help understand where that deal is at, how you can help. Um, and then move on from there. So that's one, the tooling to the process to just make sure stuff doesn't fall through the gaps, but ultimately it's just to try to focus your time for the signal to noise.

AI assessment note: “I can look at call recordings. I can look at sales engagement.”