The Exchanges

Q How do you think about the specialization or verticalization, more importantly, of sales teams? And what I mean by that is one password is a horizontal product. Amazing because you can serve so many different people, but also difficult because you can serve healthcare, banking, consumer, you name it. Um, I like verticalized sales teams. How do you think about verticalized sales teams?

A I, I think there's a time and place. Um, and again, it'll, it'll vary from company to company. Uh, we're not verticalized today. And the main reason for that is we looked at our success across every vertical. We look at win rates, ACV, time to close. Um, and we found very, very little difference, um, across these different segments. Um, and we have yet to reach any sort of saturation, um, in any one segment really. And so we're not yet at the stage where We need to hire individuals who have built a career selling to specific verticals and have deep vertical and specialized knowledge yet, but we're absolutely going to get there. Um, I think our journey is such that, you know, we're looking at segments first and foremost, because SMBs buy very, very differently than large enterprise companies. Um, territory based splits are sort of where we're at right now, making sure that we've got the right people, right language, right time zone, and so on and so forth. The next step will be to verticalize the team. So that we go deeper and wider.

AI assessment note: “we're not verticalized today. And the main reason for that is”

Q It makes me think of the hunter analogy. And I'm just fascinated. How do you think about the hunter versus farmer analogy and knowing what structure you want at what stage?

A I think ultimately it depends on, um, how your customers are buying. So, you know, I'll give you a concrete example. Um, we, you know, we started off with the hunter farmer model at one password. Um, and the main reason for that is when we landed here and started building the team, the company had already acquired 50,000 businesses that were using our product. Um, But we had less than a two percent penetration rate within those businesses because these were fanatical users that were bringing our product into the workplace. So if all we did was have one flavor of sales individual, they would favor expanding across the base. Um, and they would likely be a lot less efficient with any inbound demand, and they certainly wouldn't be pushing themselves to go out and generate outbound demand. So early on, we decided to create that friction on both ends to say, right, we're going to have a team of hunters and a team of farmers. Today and going into next year, we're actually bringing those functions back together in a hybrid sales model. And the reason for that is we now have a multi-product portfolio. Um, our customers are landing and expanding with us far more. And what we, what we saw was that we were actually losing new business deals because we were pushing too hard to get too much upfront. And so now we sort of aligned the sales motion and model to how our customers buy and take a …

AI assessment note: “I think ultimately it depends on, um, how your customers are buying.”

Q It makes me think of the hunter analogy. And I'm just fascinated. How do you think about the hunter versus farmer analogy and knowing what structure you want at what stage?

A I think ultimately it depends on, um, how your customers are buying. So, you know, I'll give you a concrete example. Um, we, you know, we started off with the hunter farmer model at one password. Um, and the main reason for that is when we landed here and started building the team, the company had already acquired 50,000 businesses that were using our product. Um, But we had less than a two percent penetration rate within those businesses because these were fanatical users that were bringing our product into the workplace. So if all we did was have one flavor of sales individual, they would favor expanding across the base. Um, and they would likely be a lot less efficient with any inbound demand, and they certainly wouldn't be pushing themselves to go out and generate outbound demand. So early on, we decided to create that friction on both ends to say, right, we're going to have a team of hunters and a team of farmers. Today and going into next year, we're actually bringing those functions back together in a hybrid sales model. And the reason for that is we now have a multi-product portfolio. Um, our customers are landing and expanding with us far more. And what we, what we saw was that we were actually losing new business deals because we were pushing too hard to get too much upfront. And so now we sort of aligned the sales motion and model to how our customers buy and take a …

AI assessment note: “I think ultimately it depends on, um, how your customers are buying.”

Q Sorry, there's a couple of things. What are the core tools that you think every sales team and leader should be using today? You said about tech stack. Which are the, like, Hail Mary, regardless of what stage sector you're in, you have to have this.

A Yeah. I mean, look, a good CRM to start. I implemented Salesforce early on here. I've done CRM migrations before. It's a pain in the butt. Um, just start with what, you know, you're going to need to scale and be done with it. Uh, outreach and gong. I was quick to implement, uh, at one password as well. Um, you know, we leverage both of those. Um, and then some form of sales enablement tool. Um, you know, there, there's tons of great ones out there. Flock J high spot seismic. Um, I think inherently you're gonna end up with a lot of different collateral and information to feed your sales team. They'll digest it and then it goes into a repository that they'll never reference ever again. And so having a tool that surfaces the right content at the right time for the right opportunity based on stage and so on and so forth, I think is pretty important.

AI assessment note: “A good CRM to start. I implemented Salesforce early on here... outreach and gong.”

Q What one final one, what one company sales strategy has most impressed you over the last year?

A I'd say, uh, I, I look, I've been really impressed with, uh, whiz and I, I guess like, you know, a typical answer in the sense that yes, they've grown very quickly and that's admirable, but knowing the amount of talent and change management cycles, they likely needed to go through on that journey from zero to five hundred million in revenue. Over that period of time, that is the impressive and remarkable part of, of that story. Um, cause the, the playbook of how you become a billion dollar company is, is, is pretty well understood as far as just like the typical steps, whether that's international expansion, multi-product portfolio, working with partners, so on and so forth. Um, but doing that over a compressed timeframe, that's the impressive feat, um, that I think Wiz has accomplished. So, um, good on them.

AI assessment note: “I've been really impressed with, uh, whiz”

Q Can you have a sales motion like we discussed with that SMB structure? If you're paying five to 15,000 dollars, you can't afford the outbound, the AE, the CS. Can you?

A No, you, you need to be very intentional about where you deploy those resources. Um, most of our outbound motion right now is invested in mid market and enterprise. Cause that's where we get the biggest bang for our buck. The SMB teams are a lot more transactional. Uh, they work on high volume, high velocity, you know, most of, most of them pay for themselves four times over. Um, you know, even if I load in all costs and then from a CS and onboarding perspective, um, you know, we rely on low touch models. Um, with smaller customers to get them going. Ultimately, we'll get someone on the phone working with them if they need the help, but it isn't the default switch of the team to just unload the mega machine for every single customer and deal regardless of size.

AI assessment note: “No, you, you need to be very intentional about where you deploy those resources.”

Q Can you have a sales motion like we discussed with that SMB structure? If you're paying five to 15,000 dollars, you can't afford the outbound, the AE, the CS. Can you?

A No, you, you need to be very intentional about where you deploy those resources. Um, most of our outbound motion right now is invested in mid market and enterprise. Cause that's where we get the biggest bang for our buck. The SMB teams are a lot more transactional. Uh, they work on high volume, high velocity, you know, most of, most of them pay for themselves four times over. Um, you know, even if I load in all costs and then from a CS and onboarding perspective, um, you know, we rely on low touch models. Um, with smaller customers to get them going. Ultimately, we'll get someone on the phone working with them if they need the help, but it isn't the default switch of the team to just unload the mega machine for every single customer and deal regardless of size.

AI assessment note: “No, you, you need to be very intentional about where you deploy those resources.”

Q When it comes to forecasts, this is great. I'm just like pummeling you with quickfire questions. When it comes to forecasts, do you rather have the unachievable that we hit 80% of? Do you rather have the achievable that we hit? How do you think about that stretch?

A Yeah. Look, we, we typically build plans so that, you know, 70% of people can achieve them. Um, you know, it, it, it's gotta be challenging enough, um, that it's, it's forcing you to push boundaries, but we, you know, we don't design them so every single person, uh, will attain them. Um, uh, the acceleration is often much greater than deceleration. So when, you know, when, when people are having, uh, you know, really strong quarters in months, they can, they can really overachieve, but, um, you know, the, the, the goal is not to set The bar just low enough so everyone makes it across. Um, it's, it's gotta be a challenge. And, and every time that I've set a goal that is at least 20 or 30% higher than I think we're capable of achieving, even when we don't achieve it, we always end up doing 10% more, um, you know, than, than the goal that we initially set or, or, or thought was realistic. And so there, there is a, a mental element of this that is, like, just Pushing people to think creatively and outside of just the art of what they see in front of them to achieve a goal.

AI assessment note: “we typically build plans so that, you know, 70% of people can achieve them.”

Q So I come into you. Sorry. It's, it's just, this is where people love it. So I come to you. Hey, I'm on your team. I'm young and enthusiastic. Um, Dave, what does week one look like? How should we spend the first seven days?

A Yeah, so look, so your first seven days you're getting set up, I'd say really your first two weeks, um, you're, you're getting to understand the product, the systems and tools, how the job gets done, you're meeting the team, um, you're in listen and learn mode. Um, you should be asking a lot of questions about what you don't understand, not just nodding your head up and down and going, you know, going through the training. Um, but we look for that curiosity in the first two weeks. It's an indication of how engaged someone is and how willing they are to be an active participant And their success as opposed to thinking, Hey, someone's going to give me a headset and a laptop, uh, and a 20 page playbook, uh, you know, and, and suddenly I'm going to hit my target. So that's what the first two weeks look like. But the steps you take after that, whether that is reaching out to top reps on the team to understand what they're doing, whether that's shadowing calls, whether that's, you know, spending time in gong, um, whether that's seeking out more training one-on-one time. Um, all of these are really important indicators to me that say you're engaged, you're in it.

AI assessment note: “so your first seven days you're getting set up, I'd say really your first two weeks”

Q How do you think about the specialization or verticalization, more importantly, of sales teams? And what I mean by that is one password is a horizontal product. Amazing because you can serve so many different people, but also difficult because you can serve healthcare, banking, consumer, you name it. Um, I like verticalized sales teams. How do you think about verticalized sales teams?

A I, I think there's a time and place. Um, and again, it'll, it'll vary from company to company. Uh, we're not verticalized today. And the main reason for that is we looked at our success across every vertical. We look at win rates, ACV, time to close. Um, and we found very, very little difference, um, across these different segments. Um, and we have yet to reach any sort of saturation, um, in any one segment really. And so we're not yet at the stage where We need to hire individuals who have built a career selling to specific verticals and have deep vertical and specialized knowledge yet, but we're absolutely going to get there. Um, I think our journey is such that, you know, we're looking at segments first and foremost, because SMBs buy very, very differently than large enterprise companies. Um, territory based splits are sort of where we're at right now, making sure that we've got the right people, right language, right time zone, and so on and so forth. The next step will be to verticalize the team. So that we go deeper and wider.

AI assessment note: “we're not verticalized today. And the main reason for that is we looked at our success”

Q Sorry, there's a couple of things. What are the core tools that you think every sales team and leader should be using today? You said about tech stack. Which are the, like, Hail Mary, regardless of what stage sector you're in, you have to have this.

A Yeah. I mean, look, a good CRM to start. I implemented Salesforce early on here. I've done CRM migrations before. It's a pain in the butt. Um, just start with what, you know, you're going to need to scale and be done with it. Uh, outreach and gong. I was quick to implement, uh, at one password as well. Um, you know, we leverage both of those. Um, and then some form of sales enablement tool. Um, you know, there, there's tons of great ones out there. Flock J high spot seismic. Um, I think inherently you're gonna end up with a lot of different collateral and information to feed your sales team. They'll digest it and then it goes into a repository that they'll never reference ever again. And so having a tool that surfaces the right content at the right time for the right opportunity based on stage and so on and so forth, I think is pretty important.

AI assessment note: “a good CRM to start. I implemented Salesforce early on here.”

Q What is the most common risk people miss that leads to deal attrition?

A More often than not, it's an understanding of what the procurement process looks like within the company end to end. There's always some surprise budget committee individual who needs to weigh in. And so not going wall to wall and understanding what it's going to take to get a deal done is the biggest mistake that I see oftentimes, and one of the leading causes of deals slipping. Um, sometimes things will happen that are completely outside of the rep's control. I get that. Um, we can only control for, for, for what we can control, but, um, More often than not, it's about missing something in the procurement chain or not getting the right amount of value established with the right individuals in the organization. Like if you're attempting to sell a half million dollar deal to a manager in a department and they're, you know, superior or their budget holder is not even aware that these conversations are taking place. That's a huge red flag. Um, because people are inherently bad at then going back and selling the business case internally. So we actually find that we, we end up coaching a lot of our reps to do exactly that. Like not just sell the product to the person that you're working with, but coach them and help them sell this internally.

AI assessment note: “it's an understanding of what the procurement process looks like within the company end to end”

Q If AEs are meant to generate their own pipeline, what the fuck are BDRs doing?

A So they're doing the same, and I, and I think that outbound prospecting does become a team sport, um, especially when you're selling in a high enterprise, um, especially when you're selling cross mid-market. I think that for the AEs, it's a matter of keeping some of those muscles sharp. Like, you think about what outbounding really is. It's, it's about captivating interest. It's about getting to the point quickly to something that matters to the individual that you're speaking to. Like, that in and of itself is valuable, even if all you're getting is an inbound call, right? That makes you more effective at that first discovery call, that first meeting. So it's an important muscle that people need to exercise, period. And I also think there's a certain amount of appreciation and gratitude that you have When you've got a BDR, you know, working their butt off to generate pipeline for you, if you understand what goes into getting that meeting set, um, you're, you're gonna, you're gonna treat that opportunity accordingly. I think that's the difference. I still expect the majority of pipeline to be generated from the BDR team, but AEs who don't self-gen, um, just doesn't work. And I think it does them a personal disservice over time.

AI assessment note: “I still expect the majority of pipeline to be generated from the BDR team”

Q Well, before we dive into the, the who, in terms of the like, what and the when, should the founder be the one to create the first sales playbook, or can you bring in a head of sales to do it for you?

A I believe strongly that it's got to be the founder. Um, there are definitely situations where, uh, that maybe isn't the case. Um, but I, I think you do yourself a disservice as a founder, like being able to get on the front line, um, and get firsthand exposure, um, to how customers are reacting to whatever it is that you're, you're pitching or, or selling, I think is an important leverage that you then need to call bullshit on anyone else that you're ultimately going to trust sales to in the future. So, um, you know, a capable go to market first hire can certainly do that, but getting involved as a founder, I think early on is critical.

AI assessment note: “I believe strongly that it's got to be the founder.”

Q How do we think about target setting for them? Again, We've got these two new reps now. I'm the CEO, but I'm a young founder. I, I'm quite naive. How do I think about goal setting and targets for them?

A Yeah, I, I'd say, you know, in both the early days of, uh, Lightspeed and OnePassword, uh, we actually started with team goals. Um, you know, we, we, we anchored the team to deliver what was most important for the company and what the company was looking to achieve. That works for a very, very, very short period of time. Um, but it, it was Important for us to sort of establish an in it together while we started to figure out, um, you know, what sort of capacity can we get out of these individuals? Um, you know, without any sort of historicals on, Hey, I know that a rep should be able to close this many deals at this value. You kind of need to figure that out. So, you know, we would leverage spits and incentives to get the most out of people and understand, Hey, w w you know, where does that back wall live? Um, but, but focus them on one common goal. I think as you, as you think about, uh, putting guardrails and defining what that comp plan is going to look like, the simpler, the better. Um, especially in the early days, like your, you know, your rep should be able to understand how much they're going to earn and how they're going to pay their mortgage without having to go through a ton of gymnastics. Um, and you should be open to changing the comp plan as your focus as a company changes. Um, you know, anchor the people that are responsible for driving revenue to, uh, the things…

AI assessment note: “we actually started with team goals.”

Q Do you believe outbound is still a viable strategy in 24? With the proliferation of AI tools, the immense supply side of content that we're able to shift now, is outbound viable?

A I think it's viable. I think it's gotten a lot harder, um, but it is viable. Um, look, I, I'd say the easiest part of my day is marking a whole bunch of emails as unread in my inbox that are clearly people trying to sell me stuff. Uh, if it's, if it's not a priority, it's, it's easy to move it out of the way. I think AI should make, uh, should actually make it a lot easier. Right? You think about the amount of time it would take for you to do proper research and discovery on a company before reaching out. AI can accelerate that dramatically. I don't think AI is necessarily going to just, you know, work on autopilot, um, you know, and, and fill your inbox with leads and responses, but I think it could help the job of outbound prospecting become a lot more effective. And I do think that, um, you know, BDRs and AEs Uh, can actually do a sharper job at prospecting with, with a lot less effort.

AI assessment note: “I think it's viable. I think it's gotten a lot harder”

Q What does pipeline inspection look like from a structural perspective? Can you walk me through it as granular as possible?

A So I I'd say that from an SMB perspective, you're often looking at pacing. You're often looking for pattern matching on what's going on that month relative to the previous month relative to the same period last year. Um, and oftentimes we're looking at those Daily. Um, we're also looking at the pipeline, like how does a drop in pipeline this week impact us next week? So it's a very, very data driven approach and you need to obsess over it. Um, and it's not about reviewing it once a month or months, a quarter. It's about living in it every single day, but sitting down and reviewing it as a team every single week, as you start to move up market, you know, the classic is like, well, you know, enterprise deals take two quarters to close. What on earth could we possibly be talking about? You know, on a week to week basis. But the reality is, is you still need to have some form of objective or goal, um, that you're working towards, even on a weekly basis, right? What outcomes are you trying to drive? What needs to be true as part of this deal in order for us to win it? And what progress have we made towards checking off those items this week, right? How much pipeline have we built? Um, even if you're looking at things sort of, you know, two quarters in arrears, what does our pipeline look like for the second half of Next year, and how are we trending there? So we do this inspection w…

AI assessment note: “the larger the deal, the more focus you're putting on sort of the account level”

Q Who's invited to this meeting? Is it the whole sales team? Only leads? Only AEs? How do we think about that?

A So I, I think it'll vary on company size, right? If your team is small enough, I would get the whole team involved in the process. Um, I think, and it's an important part of how you drive accountability. As you grow though, it's about creating a cadence, right? So, you know, every Monday, every AE is going to sit down and look at their pipeline. They're going to take inventory of what they've done that week, how they've progressed, what's fallen out, what's moving ahead. Um, and then the following day, they're gonna report that to their frontline leader. Their frontline leader is then gonna go ahead and inspect that work, ask probing questions, ensure that there's proper hygiene, and then roll that up then to their second line leader. So typically, by the time we have our weekly forecast call, um, I'm usually having it with my directs, and we've got folks from marketing, folks from our FP&A team that are joining us as well, and then we roll a summary to The executive team.

AI assessment note: “I'm usually having it with my directs, and we've got folks from marketing”

Q I totally agree with you. Uh, when you are in those reviews, and it's, I don't have much. Yeah, no, um, notion dropped out. Next one. Rippling dropped out. Yeah, I didn't have much. How do you maintain morale when sales teams are not performing?

A I think it's important to, um, see the positive and call it out, right? I think that when the results are shit, it doesn't mean that Everything is shit. Um, I think you need to be able to call out the good. I mean, ultimately selling is a very emotional sport. And so if you've got a group of deflated, uh, salespeople out there, uh, trying to get people excited about your product, uh, it's really hard to do if they're not believing in themselves. So I think it's about being positive about the things that have gone right, but I think it's about being brutally honest about the things that are not working and getting comfortable assessing that Um, attacking the problem and not the person in that scenario, right? And so we do inspection often enough. And if you're doing inspection often enough, there should not be any surprises. And if there are, then there's something you missed as part of that process. There's something you didn't inspect for. There's a risk you didn't assess or that you didn't call out.

AI assessment note: “see the positive and call it out, right?”

Q How do you do that without being so fucking obvious? So listen, Julian, I, I, we both want one password in Notion, Rippling, Vanta, you name it, whatever. Okay. We both want that there. This is a pack of information that I would use this. How do we do it?

A I think it comes, like, the subtle art there is not just loading them up with technical jargon, even if they understand it, but thinking, What are the questions that their CFO is going to ask them when you try to go and justify spend for this product? What are they going to ask? Right? And it's about giving them those answers throughout the process, right? So that they've got it. It's at the tip of their tongue. They can answer it right away. And most of the time they can't anticipate what their CEO, what their CFO is going to ask of them. So we give that to them without asking anything in return, knowing full well that they're going to, they're going to end up facing that challenge. At some point. So we, even if we don't get access to those individuals throughout the sales process, I mean, our CFO often says like, please don't have me speak to a salesperson, but we make sure that our champion is armed with the right answers to the right questions to be able to justify it.

AI assessment note: “make sure that our champion is armed with the right answers to the right questions”

Q What is the most common risk people miss that leads to deal attrition?

A More often than not, it's an understanding of what the procurement process looks like within the company end to end. There's always some surprise budget committee individual who needs to weigh in. And so not going wall to wall and understanding what it's going to take to get a deal done is the biggest mistake that I see oftentimes, and one of the leading causes of deals slipping. Um, sometimes things will happen that are completely outside of the rep's control. I get that. Um, we can only control for, for, for what we can control, but, um, More often than not, it's about missing something in the procurement chain or not getting the right amount of value established with the right individuals in the organization. Like if you're attempting to sell a half million dollar deal to a manager in a department and they're, you know, superior or their budget holder is not even aware that these conversations are taking place. That's a huge red flag. Um, because people are inherently bad at then going back and selling the business case internally. So we actually find that we, we end up coaching a lot of our reps to do exactly that. Like not just sell the product to the person that you're working with, but coach them and help them sell this internally.

AI assessment note: “it's an understanding of what the procurement process looks like within the company”

Q Well, before we dive into the, the who, in terms of the like, what and the when, should the founder be the one to create the first sales playbook, or can you bring in a head of sales to do it for you?

A I believe strongly that it's got to be the founder. Um, there are definitely situations where, uh, that maybe isn't the case. Um, but I, I think you do yourself a disservice as a founder, like being able to get on the front line, um, and get firsthand exposure, um, to how customers are reacting to whatever it is that you're, you're pitching or, or selling, I think is an important leverage that you then need to call bullshit on anyone else that you're ultimately going to trust sales to in the future. So, um, you know, a capable go to market first hire can certainly do that, but getting involved as a founder, I think early on is critical.

AI assessment note: “I believe strongly that it's got to be the founder.”

Q If AEs are meant to generate their own pipeline, what the fuck are BDRs doing?

A So they're doing the same, and I, and I think that outbound prospecting does become a team sport, um, especially when you're selling in a high enterprise, um, especially when you're selling cross mid-market. I think that for the AEs, it's a matter of keeping some of those muscles sharp. Like, you think about what outbounding really is. It's, it's about captivating interest. It's about getting to the point quickly to something that matters to the individual that you're speaking to. Like, that in and of itself is valuable, even if all you're getting is an inbound call, right? That makes you more effective at that first discovery call, that first meeting. So it's an important muscle that people need to exercise, period. And I also think there's a certain amount of appreciation and gratitude that you have When you've got a BDR, you know, working their butt off to generate pipeline for you, if you understand what goes into getting that meeting set, um, you're, you're gonna, you're gonna treat that opportunity accordingly. I think that's the difference. I still expect the majority of pipeline to be generated from the BDR team, but AEs who don't self-gen, um, just doesn't work. And I think it does them a personal disservice over time.

AI assessment note: “So they're doing the same... I still expect the majority of pipeline to be generated”

Q What did you not spend money on that you wish you had spent money on in your time at one password?

A I think we had the opportunity to be a lot more aggressive investing in Product and engineering, whether that's sort of like a, a build or buy scenario. Um, again, I, I think we had the benefit of being a profitable business with a lot of cash at a time when, um, many companies were struggling. And so I think there was a window of opportunity there for us to substantially accelerate, uh, our pace of growth. And we chose to err on the side of caution or a middle ground. Um, and so, you know, Like hindsight's always 20, 20, and who knows where we'd be today had we, had we sort of made that decision, but that's, um, that's probably one regret that I have is not pushing a little bit harder for us to do that as a company.

AI assessment note: “we had the opportunity to be a lot more aggressive investing in Product and engineering”

Q So we now need to hire our first go to market person, Julian. You're an angel in my company. I don't know what to look for. Should I go for like a tenured sales leader or should I go for like junior reps? What, what do you advise me on that first GTM hire?

A Yeah, I, I'd say, you know, if you're very early on in your journey, um, you, you need somebody who's gonna have the humility, the patience, low ego, high curiosity. You know, sometimes the person with the fancy cover at the front of the book that's touched the right companies at the right times, um, is, is not what you want. You want somebody who has something to prove, has a chip on their shoulder, and is, is motivated to build something greater. Um, than anything they've ever been a part of. Um, and so I think you're, you're largely looking for somebody who's going to be patient, not somebody who's going to, you know, blame a lack of success and all the things the company doesn't do or doesn't have, or, Hey, if only we had these systems or this much more money to invest, they should be the type of person who's going to focus on, Hey, what's in the art of possible? What can we do? How do we push the envelope further? Um, so th that's the kind of person that I think of as, as, as a salesperson I want. And look, there, there's a company, um, you know, I advise for, Um, that, that started off with founder-led sales that's now looking, you know, staring down the barrel of making that same decision of, hey, who should that first salesperson be? Uh, and, and ultimately they, they landed on an individual who, um, you know, had found success at other companies, but ultimately felt li…

AI assessment note: “You want somebody who has something to prove, has a chip on their shoulder”

Q How do we think about target setting for them? Again, We've got these two new reps now. I'm the CEO, but I'm a young founder. I, I'm quite naive. How do I think about goal setting and targets for them?

A Yeah, I, I'd say, you know, in both the early days of, uh, Lightspeed and OnePassword, uh, we actually started with team goals. Um, you know, we, we, we anchored the team to deliver what was most important for the company and what the company was looking to achieve. That works for a very, very, very short period of time. Um, but it, it was Important for us to sort of establish an in it together while we started to figure out, um, you know, what sort of capacity can we get out of these individuals? Um, you know, without any sort of historicals on, Hey, I know that a rep should be able to close this many deals at this value. You kind of need to figure that out. So, you know, we would leverage spits and incentives to get the most out of people and understand, Hey, w w you know, where does that back wall live? Um, but, but focus them on one common goal. I think as you, as you think about, uh, putting guardrails and defining what that comp plan is going to look like, the simpler, the better. Um, especially in the early days, like your, you know, your rep should be able to understand how much they're going to earn and how they're going to pay their mortgage without having to go through a ton of gymnastics. Um, and you should be open to changing the comp plan as your focus as a company changes. Um, you know, anchor the people that are responsible for driving revenue to, uh, the things…

AI assessment note: “we actually started with team goals. Um, you know, we, we, we anchored the team”

Q Do you believe outbound is still a viable strategy in 24? With the proliferation of AI tools, the immense supply side of content that we're able to shift now, is outbound viable?

A I think it's viable. I think it's gotten a lot harder, um, but it is viable. Um, look, I, I'd say the easiest part of my day is marking a whole bunch of emails as unread in my inbox that are clearly people trying to sell me stuff. Uh, if it's, if it's not a priority, it's, it's easy to move it out of the way. I think AI should make, uh, should actually make it a lot easier. Right? You think about the amount of time it would take for you to do proper research and discovery on a company before reaching out. AI can accelerate that dramatically. I don't think AI is necessarily going to just, you know, work on autopilot, um, you know, and, and fill your inbox with leads and responses, but I think it could help the job of outbound prospecting become a lot more effective. And I do think that, um, you know, BDRs and AEs Uh, can actually do a sharper job at prospecting with, with a lot less effort.

AI assessment note: “I think it's viable. I think it's gotten a lot harder”

Q Like, I disagree, like, okay, like, uh, what if they just don't care? I don't mean that badly, Julian, but I'm just like, I don't care about credential strength, like.

A Yeah, and, and, and we get that. Um, you know, the, the security practitioners that we sell to have a number of different priorities. Uh, they've got to think about everything. It's like me telling you that, like, you know, that microphone Six inches from your mouth is probably gonna give you cancer. You're like, yeah, sure. Well, everything will. So it's, it's really about contextualizing what not solving that problem, um, is gonna, is gonna mean for them, right? And, um, connecting with something that they care about, like what are they prioritizing right now within their business? Maybe it's not credential management, but maybe it is keeping employees safe. Maybe it is minimizing The threats that exist within their company. They may not agree at first conversation that, you know, solving for credential management is going to be the solution to that, but that's your job as a seller to sort of guide them there. But I think the difference for me is not trying to create a new set of priorities or things for them to think about. It's about tapping into what they already care about, what they're already prioritizing and thinking about, um, um, and, and, and working with them in that way.

AI assessment note: “It's about tapping into what they already care about, what they're already prioritizing”

Q What does pipeline inspection look like from a structural perspective? Can you walk me through it as granular as possible?

A So I I'd say that from an SMB perspective, you're often looking at pacing. You're often looking for pattern matching on what's going on that month relative to the previous month relative to the same period last year. Um, and oftentimes we're looking at those Daily. Um, we're also looking at the pipeline, like how does a drop in pipeline this week impact us next week? So it's a very, very data driven approach and you need to obsess over it. Um, and it's not about reviewing it once a month or months, a quarter. It's about living in it every single day, but sitting down and reviewing it as a team every single week, as you start to move up market, you know, the classic is like, well, you know, enterprise deals take two quarters to close. What on earth could we possibly be talking about? You know, on a week to week basis. But the reality is, is you still need to have some form of objective or goal, um, that you're working towards, even on a weekly basis, right? What outcomes are you trying to drive? What needs to be true as part of this deal in order for us to win it? And what progress have we made towards checking off those items this week, right? How much pipeline have we built? Um, even if you're looking at things sort of, you know, two quarters in arrears, what does our pipeline look like for the second half of Next year, and how are we trending there? So we do this inspection w…

AI assessment note: “So we do this inspection weekly, regardless of segment, but I'd say the larger”

Q I totally agree with you. Uh, when you are in those reviews, and it's, I don't have much. Yeah, no, um, notion dropped out. Next one. Rippling dropped out. Yeah, I didn't have much. How do you maintain morale when sales teams are not performing?

A I think it's important to, um, see the positive and call it out, right? I think that when the results are shit, it doesn't mean that Everything is shit. Um, I think you need to be able to call out the good. I mean, ultimately selling is a very emotional sport. And so if you've got a group of deflated, uh, salespeople out there, uh, trying to get people excited about your product, uh, it's really hard to do if they're not believing in themselves. So I think it's about being positive about the things that have gone right, but I think it's about being brutally honest about the things that are not working and getting comfortable assessing that Um, attacking the problem and not the person in that scenario, right? And so we do inspection often enough. And if you're doing inspection often enough, there should not be any surprises. And if there are, then there's something you missed as part of that process. There's something you didn't inspect for. There's a risk you didn't assess or that you didn't call out.

AI assessment note: “I think it's important to, um, see the positive and call it out”