The Exchanges

Q Take more trips to the bank to make bigger deposits. Uh, I was like, okay, again, this was, I was reading these when I was doing the research. They're not giving me a lot of hints, are they? So what does take more trips to the bank to make bigger deposits mean?

A So when you're talking with salespeople, one of the things This is going to be a weird thing. Um, one of the things that is, um, incredibly important is for a salesperson to understand effectiveness, um, in their movements are going to give them more capacity to be able to sell more. And so what I try to do is say, Hey, you know what? If I do my job correctly and you lean in on the playbook, And you follow the rules that have been set up. Technically, you should be able to get more done in a day to be able to make more frequent trips to the bank to make bigger deposits because that's why you're here. And I'm not going to be doing my job if it's more difficult for you to make a living or over time when your territory shrinks and your quota goes up, you can't balance the fact that I can still work the same amount of time Or less, and be able to make more money, because I'm leaning in on the system, I'm leaning in on the playbook to be able to do that. So, my message to my frontline is, my goal, if it reveals itself in a very precise way, is you go to the bank and make larger deposits more frequently, because you're following the rules of the playbook that were put into place, and until that doesn't happen, you should always be able to lean into that. So this is, this is sort of a philosophy. Um, and motivating and helping articulate that to salespeople.

AI assessment note: “So this is, this is sort of a philosophy. Um, and motivating and helping articulate”

Q I sit on many boards and the common thing that I hear is, ah, Doug, we didn't hit the numbers because you know what? It just slipped to next quarter. It's gonna happen, but it just slipped to next quarter. And I never know what to say. What would you say if you were in a board and they say, ah, slipped to next quarter?

A Well, so, so the reality is you can't close every day, every quarter, and not everything is always going to go your way. So this is always going to happen. However, it is materially triaged when the sales rep and the entire team understands the timeline that we are marching towards. And when that becomes agreeable and we hold ourselves and the customer accountable for that, Then we should be able to have a level of predictability as to what, what and how this is going to go, go, go forward. So Right now we're looking at the quarter and we're building plans with our customers that will conclude the evaluation and arrive at a decision and an implementation timeline. You have to have those discussions in constructive tension at the beginning of the campaign to understand whether or not the customer's just shopping or whether they're actually looking to solve the problem and they're preparing themselves to be able to do it. That will create more predictability in your pipeline in a quarterly close, even though some things are going to close, are, are always going to be able to push out. But having proper close plans, setting that expectation up front, making sure we're holding each other accountable for the delivery of that, having that constructive tension and being able to do that increases the probability that things remain in the quarter for sure.

AI assessment note: “having proper close plans, setting that expectation up front... increases the probability”

Q What do you think drives quality? Is it super tight ICPs with very strong discovery processes? What is it that drives that high quality?

A So, it's different for every company, but like, at Brex, because of the business that we're in, a project can be initiated by a number of different constituents or personas within an organization at multiple different levels. For multiple different reasons. So the first thing is, is that you need to be able to have the content to understand how to communicate to those personas in regards to maybe the business challenges that they have. So product marketing, positioning, um, content is like incredibly important. And then two, you have to be able to have attributes and scoring of the leads when they come in and accuracy in the data hygiene of that So, you have to make sure that people are monitoring and capturing all of this data along the way, because it is very data-driven in, in regards to that, and then you follow through the pipeline and being able to see how that's going to be able to convert over time.

AI assessment note: “attributes and scoring of the leads when they come in”

Q Now, 16 years at SAP. I mean, Doug, this is like a feat that not many people do in terms of longevity at one company. My question is, what are one to two of your biggest takeaways from 16 years at SAP?

A So the 16 years was broken up into two, like, distinct chapters. One chapter was growing up in a company called Concur, um, and Um, I joined when we were about 500 people, and about 50 or sixty million dollars in sales, um, and we grew back to almost a billion dollars before we were bought by SAP. And then SAP held us as a wholly owned subsidiary, and then started to integrate us in. So I felt like I had this, um, journey where I grew with a very, very disruptive organization, and then I joined a massive company to understand How to really scale that business globally and take advantage of it. So it was amazing, but I don't think it was like 16 years at the same company doing the same thing. I felt like I had really distinct chapters along that 16 years. So, um, that's how I sort of broke it up and, and, and sort of continued down doing that.

AI assessment note: “I grew with a very, very disruptive organization, and then I joined a massive company”

Q How do you maintain morale when a quarter's missed? It's a tough time. Sometimes a lot of work goes in and a quarter's missed. How do you maintain morale?

A If a quarter is missed, um, we need to do with seat time, but most of the time, if I'm trying to be positive, that there are a number of inputs or key indicators that are going up and to the right that would be, um, sort of indicative of successes just around the corner. Um, so Let's not make this a pattern. However, this is the stuff that we did wrong, but here's a whole bunch of stuff that is going up and to the right. So if we adhere to this, don't get rattled by getting a little bit of bad news and stay focused on adhering to the system, the process, and the playbook, then we know we're going to be able to work our way out of it. So it's the positive reinforcement that lean in on the system and the playbook, and that those things are going to pay off in the long term.

AI assessment note: “it's the positive reinforcement that lean in on the system and the playbook”

Q Can I ask you a weird one? How much of speed is talent within the sales team versus sales tooling, product market fit of company? How much of it is like individual talent versus external factors?

A I think there's a balance in both. When you get world class in both of those areas, that's when you hit the nirvana of being able to do that. However, my feeling is, is that talent in a sales rep reveals itself differently. Depending on the organization you're with, that could reveal itself that they have previous experience in being able to perform the job or be able to sell into the environment that you're being able to do. The other aspect of it is, are they smart? Are they inquisitive? Are they going to show up and work each day? Are they going to apply themselves? Are they going to measure success? Are they treating their business like a franchise? Are they taking full ownership of what they're doing? Are they accountable for every activity that they do? If I find someone like that, and we can find the balance of the right tooling and the right playbooks and the right systems in place, Then that too is in Nirvana state to be able to do that. So you can balance both to a degree.

AI assessment note: “I think there's a balance in both.”

Q Now, 16 years at SAP. I mean, Doug, this is like a feat that not many people do in terms of longevity at one company. My question is, what are one to two of your biggest takeaways from 16 years at SAP?

A So the 16 years was broken up into two, like, distinct chapters. One chapter was growing up in a company called Concur, um, and Um, I joined when we were about 500 people, and about 50 or sixty million dollars in sales, um, and we grew back to almost a billion dollars before we were bought by SAP. And then SAP held us as a wholly owned subsidiary, and then started to integrate us in. So I felt like I had this, um, journey where I grew with a very, very disruptive organization, and then I joined a massive company to understand How to really scale that business globally and take advantage of it. So it was amazing, but I don't think it was like 16 years at the same company doing the same thing. I felt like I had really distinct chapters along that 16 years. So, um, that's how I sort of broke it up and, and, and sort of continued down doing that.

AI assessment note: “I joined a massive company to understand How to really scale that business globally”

Q Lengthen your stride and quicken your step. We're going to write a book together, actually. I can be your agent. Um, these are great chapters. Um, what does lengthen your stride and quicken your step mean?

A All of these statements so that you've somehow, um, have, um, all going back to the... That most people in the world don't live to work, but they work to live. So, these aphorisms that we're talking about are just gentle reminders to make people understand, like, these are things that you constantly have to think about. Not just, not just in your professional life, but in your personal life as well. So, when I say this, like people, when, when quotas go up and territories shrink, Have, that's the definition of growth. Um, then the only way for you to be able to make more money is to go faster. And there's only two ways in the world, regardless of who you are, what age you are, what shape you are, whatever, to go faster in this world, which is you have to lighten your stride and quicken your step. It's really not that difficult. Now there's a thousand different books and techniques and tools and equipment to be able to do that. But there's only one way to run faster. Lengthen your stride and quicken your step. So we break down where the rep is or where the leaders are or where the teams are to say, what is preventing you from lengthening your stride and quickening your step? Let's remove those things and then let's lean in on the too late to make that happen over and over again. That reveals itself differently in different teams, but that's the concept of it.

AI assessment note: “the only way for you to be able to make more money is to go faster”

Q What's a good reason to lose a deal?

A What's a good reason to lose a deal? I think that, um, if they don't have a business problem that we uniquely solve, um, you don't want to jam something down their throat because you're only going to have a terrible customer success implementation process down the road. Um, there are, you know, non-controllable things that happen. People go out of business. People get bought. Uh, there's divestitures. So these are things that are sometimes outside of your control. That's why There's an old adage, you may know this, time kills all deals. Um, so that's why you're always constantly looking at your cycle time. How are you constructing this? How quickly can you get to a yes or a no? A no early is as good as a yes later. So making sure that you're, you're constantly evaluating, you know, what is the activity you're doing and how effective are you being in your day?

AI assessment note: “if they don't have a business problem that we uniquely solve”

Q Demand creation in 2023 is much harder than in 2021, especially. What do you say to teams in tougher years where demand is not as abundant as it was?

A So, well, first of all, I, I struggle, I struggle with that comment inherently because, um, in the business that Brex is in, um, spend management and total spend management, most organizations in the best of times will need some form of managing their total spend whenever they give money to an employee or a vendor to spend on the company's behalf. In good times, that has a different pattern. But, like, you're saying, like, hey, in bad times, how is it difficult to be? I think that those are the best times to create demand. When you are focused on being able to drive value in regards to investments a company makes in giving employees money to spend on their behalf, the tighter the times are, the more they need to pay attention to this. So, I guess it's a mindset. We're building pipeline Incredible right now, um, going through that because of the times that they're in.

AI assessment note: “I think that those are the best times to create demand.”

Q What do you think is the biggest challenge that salespeople have when they hear that? What's the hardest next step for them?

A I think, I think what, what manifests itself is sales reps, if they're, if they don't take that, like seriously, they try to force deals to happen, and they're not being honest in whether or not their activity is as effective in achieving their goal, because it's not, you don't, you don't wake up every single day and say, hey, how hard can I work For as little payback as possible. It's literally the opposite way around. So, so when I'm hopeful reps hear that they're like making decisions on the activity they're doing directly in front of them and saying, does this get me closer to going to the bank to make larger deposits more frequently? Or is this taking me away from that? And, and if it's taking me away, Raise your hand. I want to come over and understand how to reduce that drag, how to be able to get more frictionless activity in your business so you can be able to do that. So it's a constant feedback loop.

AI assessment note: “they try to force deals to happen, and they're not being honest”

Q person you're selling to, the CTO, everything is just looking fantastic, and then suddenly the CEO has a bit of a dodgy week of fundraising challenges, and actually goes, you know what, no, we're not going to spend anything, we're not going to engage with any new vendors, and has a sporadic turn. As a sales leader, can you really do anything about that? Do you know what I mean?

A Yeah. So I guess, I guess it would be in the anticipation and the understanding of whether or not that that organization was in a, a point where they needed more funding or they were doing like to, to not know what the financial, um, aspect or pattern is of the organization you're selling to is inexcusable. Um, and then, and then two, yeah, sure, certainly something happens. However, if you anticipate that that's a probability that it is going to happen, you have to hold that up against the value proposition that you're bringing, and then understand as to whether or not it holds enough weight to be able to do that. So if, if the funding, if, if funding is an issue, this one's an interesting one. If funding is an issue, we should know, we should know that coming out of the gig A. B, if, if the value proposition is weak enough where even a shift in that is going to throw this, you know, apple off the cart, then we have to be okay with the fact that that's the case, or we didn't go wide enough, or we don't know what's going on. So it's, it's the depth of the value proposition and the impact we're going to have on the organization against what the controllable or uncontrollable event is going

AI assessment note: “depth of the value proposition and the impact we're going to have on the organization”

Q What do you think is the biggest challenge that salespeople have when they hear that? What's the hardest next step for them?

A I think, I think what, what manifests itself is sales reps, if they're, if they don't take that, like seriously, they try to force deals to happen, and they're not being honest in whether or not their activity is as effective in achieving their goal, because it's not, you don't, you don't wake up every single day and say, hey, how hard can I work For as little payback as possible. It's literally the opposite way around. So, so when I'm hopeful reps hear that they're like making decisions on the activity they're doing directly in front of them and saying, does this get me closer to going to the bank to make larger deposits more frequently? Or is this taking me away from that? And, and if it's taking me away, Raise your hand. I want to come over and understand how to reduce that drag, how to be able to get more frictionless activity in your business so you can be able to do that. So it's a constant feedback loop.

AI assessment note: “they try to force deals to happen, and they're not being honest”

Q How do you think about creating multiple champions in the sales process? I, I, on paper, it sounds wonderful, but to be like, Doug, I love our chats, I'd love to meet the rest of your team, it always feels kind of dehumanizing, and it People know that you're trying to do it. How do you create multiple champions without transactionalizing it?

A It's a difficult one because you have to be okay with constructive tension in a sales campaign, and if you don't have constructive tension in a sales campaign, then you're probably not introducing something that's pushing the boundaries of the thinking of the group you're talking to. So, the way in which I coach to be able to do that is the fact that We have a very, very specific thing that we do to improve a customer's business, and it drives outcomes that they have yet to fully understand because it is a disruptive way of being able to think about it. In order for me to determine whether or not we have a platform to be able to do business, these are the steps I have to take to be able to do that. The benefit is, Mr. Customer, or person I'm talking to, is that You will be able to determine whether or not this is something you would want to continue to invest more discovery in, or you want to just cut bait and we don't have an opportunity. The faster we can get to that, the more time we'll save for one another. So you have to be okay pushing the customer to be able to do something that they don't want to do, but it's in their best interest to do it because the thing that I'm trying to help them understand is something that they don't fully understand. So I have to bring that expertise. I have to push the agenda, and I have to be okay with constructive tension to change sort of …

AI assessment note: “you have to be okay pushing the customer to be able to do something”

Q Lengthen your stride and quicken your step. We're going to write a book together, actually. I can be your agent. Um, these are great chapters. Um, what does lengthen your stride and quicken your step mean?

A All of these statements so that you've somehow, um, have, um, all going back to the... That most people in the world don't live to work, but they work to live. So, these aphorisms that we're talking about are just gentle reminders to make people understand, like, these are things that you constantly have to think about. Not just, not just in your professional life, but in your personal life as well. So, when I say this, like people, when, when quotas go up and territories shrink, Have, that's the definition of growth. Um, then the only way for you to be able to make more money is to go faster. And there's only two ways in the world, regardless of who you are, what age you are, what shape you are, whatever, to go faster in this world, which is you have to lighten your stride and quicken your step. It's really not that difficult. Now there's a thousand different books and techniques and tools and equipment to be able to do that. But there's only one way to run faster. Lengthen your stride and quicken your step. So we break down where the rep is or where the leaders are or where the teams are to say, what is preventing you from lengthening your stride and quickening your step? Let's remove those things and then let's lean in on the too late to make that happen over and over again. That reveals itself differently in different teams, but that's the concept of it.

AI assessment note: “the only way for you to be able to make more money is to go faster.”

Q Can I ask you a weird one? How much of speed is talent within the sales team versus sales tooling, product market fit of company? How much of it is like individual talent versus external factors?

A I think there's a balance in both. When you get world class in both of those areas, that's when you hit the nirvana of being able to do that. However, my feeling is, is that talent in a sales rep reveals itself differently. Depending on the organization you're with, that could reveal itself that they have previous experience in being able to perform the job or be able to sell into the environment that you're being able to do. The other aspect of it is, are they smart? Are they inquisitive? Are they going to show up and work each day? Are they going to apply themselves? Are they going to measure success? Are they treating their business like a franchise? Are they taking full ownership of what they're doing? Are they accountable for every activity that they do? If I find someone like that, and we can find the balance of the right tooling and the right playbooks and the right systems in place, Then that too is in Nirvana state to be able to do that. So you can balance both to a degree.

AI assessment note: “talent in a sales rep reveals itself differently.”