The Exchanges

Q That is very, very kind of you. Now, I, I love a little bit of context, and I think, you know, sales is something that often I hear people fall in love with, and I wanted to start, when did you fall in love with sales first, and what was that entry point for you?

A I didn't get into sales coming out of college. I was actually in finance and accounting, and I worked in a finance and an accounting organization, uh, coming out, and then one of my buddies said, hey, you know what? I think you'd be awesome in sales. Why don't you talk to a recruiter? So I spoke with the recruiter and my very first sales job was at a company called Cintas. They rent uniforms and they do programs like that. And it was an incredible journey. They had an incredible training program. And the second I got into that organization, met the people and started to understand what sales was all about. I fell in love immediately. It was amazing.

AI assessment note: “The second I got into that organization... I fell in love immediately.”

Q Can I ask you, how do you think about effective goal setting against pipeline that actually ties back to revenue? Because I've done it before where you say, hey, I want X number of leads, and they go out and get X number of really shit leads. It creates no dollars. How do you think about creating effective goals that tie to revenue?

A So if we're speaking about pipeline, then first I begin with the source by which the pipeline is created. And there are a number of sources by which that can be, that can be inbound, that can be partnered, that can be self-generated, um, that could be internal referrals from the organization, and so on and so forth. So first of all, we understand where is it that we can be able to get our pipeline. Then what we have to do is we have to create attributes To that pipeline to be able to understand the characteristics of it. And primarily the way in which I would go that is the quality of that pipeline of conversions at each stage of the pipeline process. So then we can be able to dial in and say, okay, this message through this channel converts at a higher rate, and then you can adjust your levers and your, and your dials to be able to lean in on that You have to be able to have better pipeline. So the, the goal would be not to create, everyone talks about like, you need that five X pipeline, you need that seven X pipeline in order to make your goals. Not necessarily. When I left Concur and where I'm trying to drive Brexit, we had less than one X pipeline going into a quarter because we knew how to build pipeline in the customer base. We knew how to be able to convert it. So our effectiveness in pipeline creation just created the proper pipeline To be able to do those kinds of thi…

AI assessment note: “It's not the abundance of pipeline. It's the quality of the pipeline from source”

Q Can I ask, how do you think about increasing urgency in a sales process? Most things are not like hair on fire. Like, you know, some things like cyber protection when you've been attacked. Yes, you need it right now, but most things you don't have to buy today. How do you create urgency in the sales process?

A Yeah, so the best way, the shortest answer for that is that you have a value proposition that's either going to save the company money, make the company money, save time, or do something so dramatic that waiting another day or another week has a financial impact on that. And then if you're capable of being able to articulate that as cleanly and crisply as possible, then every day you wait that you don't address this problem. You're just hemorrhaging cash or throwing money out the window. That's going to be the easiest way to be able to do that. It means you have to have a very strong value proposition. You have to be very diligent in your discovery. We talked about this earlier. You have to talk to multiple constituents, and you have to put a business case that all folks believe Is something that is going to be impactful to the organization. In the thing that Rex sells, I'm letting you know that, and I say this to my team all the time, it's a mandatory non-core, non-mission critical business process. So, this is just a business process that you have to deal with because you're in business. Um, it doesn't mean that it's not critically important because, as I said before, it's the last financial frontier that organizations have yet to tackle. So, Having multiple interviews, doing a deep discovery, forcing yourself to understand how the business operates will reveal whether or not…

AI assessment note: “waiting another day or another week has a financial impact on that”

Q You said measurable outcomes there, and it made me think of a, a word that is thrown about so much, and I just don't think it's really very clear, which is sales playbook. When you think about sales playbooks, what does sales playbook mean to you when you hear that?

A So for me, um, like it has a couple, it has a couple of different like layers to it, if you will, Harry. Like for me, like a general sales playbook is the fact that in, in order for whatever segment you're talking about to run an effective campaign that provides a delightful customer experience where we explore whether or not there's potential for a partnership You need to do these particular things in this particular sequence, and each one of these things has these criteria that have to be fulfilled before you go to the next one. And being able to get people to respect the fact that if you skip a step or you skip checklist items, it's going to reveal itself at the end. And it's not that you're trying to, to, um, convince a company or trying to You know, trick a company. This is honestly the fact that if you miss a step down the way, then that partnership isn't going to be that promise that we're going to be able to deliver. So at the very highest level, steps in the process, checklist for each step, adhering to finishing that in order to go into the next one, um, is really how I look at a playbook and how important that is to be able to do that.

AI assessment note: “steps in the process, checklist for each step, adhering to finishing that”

Q the show, and he said the hard thing about this time is, before you'd just have people call and they would upsell, they'd pay, and then say, hey, let's have 20 more seats. And now we have to prove our ROI with data, with case studies, and actually we're changing a lot of our CS team structure to accommodate the expansive needs of like proof. Are you seeing that too?

A Yes. 100%, yes. Like, you're, you're only as good as the last promise you made and fulfilled with an organization, um, and making sure that you're driving business outcomes that are important to the company, not for you. The second a customer thinks that you are trying to do something that's benefiting you personally or breaks versus actually serving the customer, then all trust is lost. So what you're Currently are you're constantly trying to be able to do Harry is being able to understand the business challenges that they face, understanding how impactful that is to the organization, and then being able to talk openly about how we may or may not be able to participate and helping those come to life. And, and if you have a business process and a business review process supported by value engineering research insight, Experts, and you're bringing these ideas to a customer, that's when you have the most valuable relationship. Add-ons, um, expansions, purchase of other products or categories of products are a byproduct of doing all of this other stuff really, really well.

AI assessment note: “Yes. 100%, yes. Like, you're, you're only as good as the last promise”

Q What's a bad reason for, like, not winning a deal? If you, if we had a deal review and you said, how did that deal go? I said, yeah, we didn't get it. And then what would you get?

A Yeah. So there's one, there's a huge pet peeve of mine. The only reason that you, that I get furious when we lose a deal is when we're surprised, and that can reveal itself in a number of different ways. If you are running a proper deal, you shouldn't be surprised, and if at the end of a campaign, insert whatever it was that surprised you, that is a bad reason to lose a deal, because if you're good at your profession, You should never be surprised as to why you lost the deal. It should be evident, and you should have done it, and you don't win them all, totally, but if at the end we realized that there was an individual we didn't talk to, there was a department that was looking at something similar, uh, whatever the answer is here, that is inexcusable if you're running your campaign in the way in which we need you to run your campaign.

AI assessment note: “The only reason that I get furious when we lose a deal is when we're surprised”

Q Final one before we do a quick fire. What do you think are the biggest mistakes founders or sales leaders make when they hire their sales teams?

A I think what I've seen is that they rely too heavily on the sales person having all the answers for how to be able to run a proper campaign or to understand how to position value or what kind of information is necessary when you're capturing it during the course of, um, the sales campaign. So I think that, uh, founders, um, underestimate The supporting cast of characters and tooling and expertise and enablement that has to accompany a salesperson. A salesperson on and to themselves aren't going to sell well on average. They need to be supported by a team of people that tools them correctly, and then that works much better. It doesn't need to be massive. It doesn't need to be overdone, but all of the departments, this is where all the work sort of comes to a point. And to think that that salesperson just magically is going to do that without having some teams that are going to help them understand what to do is, is short sighted.

AI assessment note: “they rely too heavily on the sales person having all the answers”

Q What's a bad reason for, like, not winning a deal? If you, if we had a deal review and you said, how did that deal go? I said, yeah, we didn't get it. And then what would you get?

A Yeah. So there's one, there's a huge pet peeve of mine. The only reason that you, that I get furious when we lose a deal is when we're surprised, and that can reveal itself in a number of different ways. If you are running a proper deal, you shouldn't be surprised, and if at the end of a campaign, insert whatever it was that surprised you, that is a bad reason to lose a deal, because if you're good at your profession, You should never be surprised as to why you lost the deal. It should be evident, and you should have done it, and you don't win them all, totally, but if at the end we realized that there was an individual we didn't talk to, there was a department that was looking at something similar, uh, whatever the answer is here, that is inexcusable if you're running your campaign in the way in which we need you to run your campaign.

AI assessment note: “when we're surprised, and that can reveal itself in a number of different ways.”

Q Does the old school enterprise sale go to the Taylor Swift concert, the Superbowl? Does that still work?

A Not as much. The only reason being is most organizations now have policies and being able to receive gifts, um, associated with that. So most companies have kind of alleviated that, but I go back to the conversation that we had before. Of course, there needs to be a relationship with between myself as a salesperson and company or the individual that I'm doing with, but What we're seeing is that customers will value them, you challenging their ideas or their status quo by being able to bring insights or, or, or views that are pushing the boundaries. So I go back to if you're teaching someone something and you're creating constructive tension, there's more respect for that relationship than whether we go to a Taylor Swift concert or something like that.

AI assessment note: “Not as much. The only reason being is most organizations now have policies”

Q I could, I could keep going on that train, but I'm like, shit, I need to actually vote. But I had so many great quotes that you say, and I called it the aphorisms of Doug. Uh, which I love as a title for this. So number one is pipeline is our air without it. We die. Can you unpack this for me and, and what you mean by that?

A Sure. So one of the things that I don't think organizations embrace fully is the fact that you obviously have a marketing department, and on the surface, you think, hey, marketing department is responsible for pipeline. And to a degree, that's correct. However, everyone's responsibility is demand creation. So I have three major objectives that I tie My entire go-to-market distribution team too. One is advanced demand creation. Two is the profitable conversion of that, uh, pipeline. And then three is the protection and growth of our customer base. So when I say pipeline is our heir, I say that everybody has to contribute to building demand. And if you don't, then we are going to run out of demand to be able to meet the growth goals that we have. So everything begins with Everybody pitching in to create pipeline and demand, and that is why I say that this is our area. It doesn't matter what department you're in, it doesn't matter what function you have, you constantly have to be thinking about how you're contributing to building demand in an organization.

AI assessment note: “when I say pipeline is our heir, I say that everybody has to contribute”

Q I mean, that's brilliant. I listen. The next one is threading multiple needles with one toss of the thread. What did you mean by this? Can you unpack this one?

A So when I'm talking with, um, and coaching my either leaders or my sales Folks, or all of the contributing departments that are there, I don't think that people recognize that a properly run sales campaign begins at, like, hello, right? And so, you have this thread, and in order to get a deal done, especially in this environment, you have to be so precise in the way in which you're tossing that, and it's not just going through, like, hey, I've got to just convince the CFO, or I just have to convince the vice president of finance or controller. You actually have to throw that thread, and you have to be able to Convince and hook multiple people, maybe five, six, seven people through that. So it's how precise are you? Did you line everything up? And when you toss it, you really have only one toss because companies today aren't going to give you a second or third chance if you falter during the course of your campaign. So it's a way to bring focus to people to say every word you say, every action you do, Has to be precise, and it has to be leaning towards something that you want to get done. So I always make that thing. You're tossing thread through multiple needles. That's how precise we need to be. And if you're not thinking that way, then you're doing yourself in the company that you're actually trying to serve. A complete disservice.

AI assessment note: “you have to be able to Convince and hook multiple people, maybe five, six, seven”

Q Can I ask, how do you think about increasing urgency in a sales process? Most things are not like hair on fire. Like, you know, some things like cyber protection when you've been attacked. Yes, you need it right now, but most things you don't have to buy today. How do you create urgency in the sales process?

A Yeah, so the best way, the shortest answer for that is that you have a value proposition that's either going to save the company money, make the company money, save time, or do something so dramatic that waiting another day or another week has a financial impact on that. And then if you're capable of being able to articulate that as cleanly and crisply as possible, then every day you wait that you don't address this problem. You're just hemorrhaging cash or throwing money out the window. That's going to be the easiest way to be able to do that. It means you have to have a very strong value proposition. You have to be very diligent in your discovery. We talked about this earlier. You have to talk to multiple constituents, and you have to put a business case that all folks believe Is something that is going to be impactful to the organization. In the thing that Rex sells, I'm letting you know that, and I say this to my team all the time, it's a mandatory non-core, non-mission critical business process. So, this is just a business process that you have to deal with because you're in business. Um, it doesn't mean that it's not critically important because, as I said before, it's the last financial frontier that organizations have yet to tackle. So, Having multiple interviews, doing a deep discovery, forcing yourself to understand how the business operates will reveal whether or not…

AI assessment note: “you have a value proposition that's either going to save the company money, make the company money”

Q Speaking of kind of those big contracts, when you get them, I think the hardest thing is actually the handoff to CS. It's this beautiful process of relationship building and getting to know each other. And then it's like, great. Now you've signed. Here's Jasmine, or here's Simon, or whoever the CS is. How do you do the handoff well, do you think?

A It begins with taking a look at the entire customer life cycle. From beginning, uh, where we create awareness, um, the type of sales campaign that we run, what we capture during that sales campaign, what we pass over to the implementation team, how we're logging our interactions with those individuals, and then being able to transition to customer success. So in what we're trying to build at Brex, and we're getting maniacally good at this, is making sure that During the awareness process for those people that raise their hand to learn more, we put them into a sales process that's indicative of their role and the business challenge that they have. We're capturing the information in a platform, passing that off to a sales to service handoff into the implementation team. The sales rep and the readiness team stay very close at hand. Sales rep peels off. The customer success is introduced during the implementation process. We catalog and log everything that needs to happen, and if you recall, and I've said this a couple of times, the only reason why someone's going to buy Brex, for instance, is because it's going to improve their business by being able to deliver an outcome. The awareness process had somebody that said, I'd like to learn more about that. I do have a problem, and I'd like this kind of outcome. The sales campaign captures that. When it gets to customer success, the on…

AI assessment note: “passing that off to a sales to service handoff into the implementation team.”

Q Can I ask you, Doug, everything you say is very structured, logical, and rational, and it just seems so kind of in place. What's the hardest part about being kind of the revenue leader that you are?

A Uh, you know, I think that one of the, one of the joys about this is that as prepared as you can be, and as organized or as thoughtful, um, that you can be, it's still people. And, you know, we are a human wrapper around a world-class product, and we interface with all Types of individuals and all different levels within an organization. And that creates a really unique platform that is. Unpredictable at times, people have bad days and good days and kids are sick. Yeah. And you know, my car broke down and stuff happens. And when you scale and you have hundreds, if not thousands of people working for you and you're inter interfacing with tens of thousands of individuals at Companies. Um, I think that that level of human impredictability is the piece that, um, you know, sort of like bleeds into it a bit.

AI assessment note: “that level of human impredictability is the piece”

Q Would you rather have someone who's sold to the existing customer segment you sell to, so they know the deal size, the deal process, or would you rather someone who sold to the segment you sell to in terms of start, like the specific customer base?

A Like I said, yeah, yeah. I think it's, I think it's a combination of both, and I know that that may seem like a cop-out answer for you, but I do believe that there needs to be, um, the right kinds of individuals that have some industry experience or segment experience, I mean, some industry experience in, in what we do, selling, for instance, to the office of the CFO, or maybe some, something tangential to, uh, total spend management or spend, spend management, um, because there needs to be that, um, experience and expertise that exists within the Salesforce. But, Like Brax, what I can't do is I can't have a full cadre of those people because I also am introducing a very, very new business solution that's out there, and having a clean slate and maybe selling to the segment, whether it be startup or whether it be mid-market or enterprise, but not having the spend management experience is also very, very cool because They don't have any baggage or preconceived notions of what it could be. So when you can balance some experience with the right type of person, with someone who has segment experience, but no, not industry experience, that's when you get your best, most innovative and sort of interesting, uh, sales campaigns and structure and, and distribution models in my opinion.

AI assessment note: “I think it's a combination of both, and I know that that may seem”

Q How have you changed most as a sales leader?

A Me? I think that when I was younger, I used to think being a great sales leader was always being at the top of the leaderboard, um, by hook or crook. Um, and now I find joy in building, um, systems and departments and infrastructure where the Output or the result of the byproduct of that is always crushing your quote. So it's the reorientation of not going for the quota. It's the reorientation of doing all the little things that actually create the byproduct of crushing your quota. So in, in my family, we have a saying, it's not the score. It's not the box score that, uh, the thing that you focus on. It's all the little things that the box score doesn't have, because if you do those little things, the box score takes care of itself. Every single day and twice on Sunday.

AI assessment note: “when I was younger, I used to think... now I find joy in building”

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: “you should be able to get more done in a day to be able to make”

Q You said measurable outcomes there, and it made me think of a, a word that is thrown about so much, and I just don't think it's really very clear, which is sales playbook. When you think about sales playbooks, what does sales playbook mean to you when you hear that?

A So for me, um, like it has a couple, it has a couple of different like layers to it, if you will, Harry. Like for me, like a general sales playbook is the fact that in, in order for whatever segment you're talking about to run an effective campaign that provides a delightful customer experience where we explore whether or not there's potential for a partnership You need to do these particular things in this particular sequence, and each one of these things has these criteria that have to be fulfilled before you go to the next one. And being able to get people to respect the fact that if you skip a step or you skip checklist items, it's going to reveal itself at the end. And it's not that you're trying to, to, um, convince a company or trying to You know, trick a company. This is honestly the fact that if you miss a step down the way, then that partnership isn't going to be that promise that we're going to be able to deliver. So at the very highest level, steps in the process, checklist for each step, adhering to finishing that in order to go into the next one, um, is really how I look at a playbook and how important that is to be able to do that.

AI assessment note: “steps in the process, checklist for each step, adhering to finishing that”

Q How do you think about when is the right time to To transition between playbooks. You know, you've scaled orgs to over 600 people. The playbook changes with stage from, you know, uh, really pre-PMF to finding early PMF. The scaling into, you know, multi-hundred people organizations. How do you know when's the right time to change playbook?

A You know, that's a go. So we get signal back almost on a daily, even a weekly basis that would give us some Insight that our current playbook would need tweaking. So, how I handle it, even with where Brex is, is that one of the departments that we built actually catalogs those things, and then when they build up to a specific level of residue, we figure out when is the right time to be able to augment the playbook and then be able to re-enable the teams and introduce that on a regular basis. So, I don't introduce anything in the middle of a quarter. I'll only introduce something at the beginning of a quarter. There are certain things that are too disruptive to introduce in a quarterly basis, so we'll take those half year or full year. So it's like, ah, really, you have to capture all of this data, and then you have to take a look at it, and then know when to introduce it, so you just don't disrupt the business continuity and the motions that are going on a regular basis.

AI assessment note: “I don't introduce anything in the middle of a quarter. I'll only introduce something at the beginning”

Q And how do you do them in terms of reviews as a team? I'm just fascinated. And do you do coaching on those sales calls?

A Yeah. So one of the departments that we have is an enablement department. And what we try to do is break down the sales methodology into specific steps. And then when we're looking at a sales call, it's very difficult to look at it in Totality. We break it up into bite-sized steps and then be able to critique whether or not we are doing the things to get access to unique information that we can be able to determine whether or not our solution is, is a unique, uh, way of being able to solve the business problem. So when I break sales calls down, I break it down into how much are we listening? What kind of discovery questions are we asking? Are we gaining access to unique information that others wouldn't be able to get to because we are so thoughtful in our preparation and doing that, then what do you do with that information in order to change the buying criteria to lead to our solution? Everything follows that sort of TikTok pattern along the way.

AI assessment note: “We break it up into bite-sized steps and then be able to critique”

Q Can I ask, how do you know if you're speaking to a actual buyer? A lot of people say they have the buying permissions and actually don't. Being focused and having one toss of the thread. How do you make sure that you're actually speaking to the buyer?

A So there's a, well, there's a couple of different ways. Well, first of all, in a very, very pragmatic sense, asking that individual the last time they, for instance, implemented something similar to Brex, and then just listen. And if they don't have a precise or concise answer, or can't point back to something that they did, then you probably are not talking to the buyer. You're probably talking to an influencer, or maybe even someone that's going to have a massive impact on the overall, but If they haven't bought something and can articulate, yes, this is what happened, this is what I did, this is what I bought, this is how it went, and this is what happened, it's difficult. The reality is, is that most often than not, we, because of we're high transaction, high volume, we can study the patterns of what happens with similar organizations, and I can train the salesperson that, hey, if you're going into a 500 person technology organization and you're talking to this persona, this is how Naturally, the buying pattern would be, you're not talking to the buyer here, the buyer will be here, they'll be not revealed until the end, so you're gonna have to do this to get there to do that. So, it's understanding and interpreting the data to be able to help coach the salesperson so they don't get tricked.

AI assessment note: “asking that individual the last time they, for instance, implemented something similar”

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 Doug, when you think about the start of a quarter, I think to Wolf of Wall Street, you know, Leonardo DiCaprio kind of, I'm not fucking leaving style. What do you, what do you do to encourage, inspire a team to go chase a quarter like they've never chased it before?

A Most of the time people have personal goals or aspirations that are going to require some level of funding in order to be able to achieve. So the very first thing that I try to do is try to help people understand that the more they push themselves with personal goals and aspirations, the more it needs to be counterbalanced by professional Um, um, you know, uh, advancement and, and the counterbalancing of that. So the very first thing is, is that most people don't believe that they can achieve such a level of greatness because they haven't had a platform or an environment that actually invites personal aspirations and goal setting to be part of the professional process. That's one. Two, is being able to have people understand what is the The purpose that we're trying to achieve here. Um, and do you have like an awareness of how rare it is to be at a company like Brex during this moment in time to have this incredible resourcing, tooling, and ingenuity around you, and you will only have regrets if you don't take advantage of this moment right here, right now. And it's not because I need you to hit a quota or even hit a number. It's realizing your fullest potential to achieve your personal goals by recognizing how rare it is to be in this environment, and I think that's sort of the experience level that I bring to be able to do that, and what happens is this builds on itself. As m…

AI assessment note: “help people understand that the more they push themselves with personal goals”

Q How do you think about when is the right time to To transition between playbooks. You know, you've scaled orgs to over 600 people. The playbook changes with stage from, you know, uh, really pre-PMF to finding early PMF. The scaling into, you know, multi-hundred people organizations. How do you know when's the right time to change playbook?

A You know, that's a go. So we get signal back almost on a daily, even a weekly basis that would give us some Insight that our current playbook would need tweaking. So, how I handle it, even with where Brex is, is that one of the departments that we built actually catalogs those things, and then when they build up to a specific level of residue, we figure out when is the right time to be able to augment the playbook and then be able to re-enable the teams and introduce that on a regular basis. So, I don't introduce anything in the middle of a quarter. I'll only introduce something at the beginning of a quarter. There are certain things that are too disruptive to introduce in a quarterly basis, so we'll take those half year or full year. So it's like, ah, really, you have to capture all of this data, and then you have to take a look at it, and then know when to introduce it, so you just don't disrupt the business continuity and the motions that are going on a regular basis.

AI assessment note: “we get signal back almost on a daily, even a weekly basis”

Q Can I ask, when you reflect on that time and big company kind of mindset, what are one or two of the biggest takeaways you think that you've taken with you from that experience to Brex in the new role?

A So, um, I think that the biggest one is that Concur at the time was a very disruptive organization for the industry that it was in. We did something that no one else was doing at the time. We combined two business processes, travel and expense, and we jammed them together. And we were met with huge blowback. Uh, the industry thought we were crazy. Um, this never is going to work. Concur lost their mind. Um, and so I really was very, very purposeful and passionate about making this come to life because I truly believed that that was a business process. So it was that disruptive nature that I think I learned and then how to stick with it. Um, how to be able to describe something that's different where maybe customers did not understand the business challenge or business pain that they had was probably the biggest takeaway, like changing the buying criteria to lead to your product. Um, was one of the biggest things. And then I had incredible leaders and incredible coaches, um, throughout my time at Concur and at SAP. Um, and I wouldn't be half the leader I was today if I wasn't exposed to that and experienced that sort of upbringing, um, during those time and being able to do that. At Brex, um, I built eight new business departments that didn't exist in order to support this business motion. Um, and it's that kind of, like, just explaining, uh, describing, making sure that they un…

AI assessment note: “how to be able to describe something that's different... was probably the biggest takeaway”

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: “first thing is, is that you need to be able to have the content”

Q Doug, when you think about the start of a quarter, I think to Wolf of Wall Street, you know, Leonardo DiCaprio kind of, I'm not fucking leaving style. What do you, what do you do to encourage, inspire a team to go chase a quarter like they've never chased it before?

A Most of the time people have personal goals or aspirations that are going to require some level of funding in order to be able to achieve. So the very first thing that I try to do is try to help people understand that the more they push themselves with personal goals and aspirations, the more it needs to be counterbalanced by professional Um, um, you know, uh, advancement and, and the counterbalancing of that. So the very first thing is, is that most people don't believe that they can achieve such a level of greatness because they haven't had a platform or an environment that actually invites personal aspirations and goal setting to be part of the professional process. That's one. Two, is being able to have people understand what is the The purpose that we're trying to achieve here. Um, and do you have like an awareness of how rare it is to be at a company like Brex during this moment in time to have this incredible resourcing, tooling, and ingenuity around you, and you will only have regrets if you don't take advantage of this moment right here, right now. And it's not because I need you to hit a quota or even hit a number. It's realizing your fullest potential to achieve your personal goals by recognizing how rare it is to be in this environment, and I think that's sort of the experience level that I bring to be able to do that, and what happens is this builds on itself. As m…

AI assessment note: “The very first thing that I try to do is try to help people understand”

Q I'm always fascinated by deal reviews when we spoke about kind of expansions there and then also, you know, churn that can happen too. How do you structure deal reviews? How often do you do them? Who's invited? Who does the agenda? Can you just take me inside the world of deal reviews for you?

A So I normally have the frontline managers, um, in each of the segments or each of the divisions be able to aggregate deal reviews for their team. The deal review process is a very, very finite process that, you know, talks about Uh, sort of like, what are the challenges an organization has? What happens if we solve these challenges? Where are we with our coverage model of the constituents that we believe would have insight or visibility into this, or the reverberating effects of it? Uh, what kind of data have we, have we received? What's the topography of their infrastructure? Um, how are we creating, um, a path to be able to, um, You know, help them conclude the process. Hopefully they buy us, but maybe they don't. Um, but nobody just wants to be in these perpetual processes, so it's constantly taking a look at where are we missing information to be able for both parties to arrive at a decision to either let's partner or let's cut bait and move on from there. So the deal review process is constantly in that, in that sort of state, same area.

AI assessment note: “I normally have the frontline managers, um, in each of the segments or each of the divisions”

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: “it would be in the anticipation and the understanding of whether or not that that organization”

Q Do you find that people are receptive to it though? I find that most buyers now in technology companies are just like, we're shut for business, but, and it's almost as closed mindedness to any form of new vendor. Do you find that?

A Yes. Well, first of all, yeah, money is tight, and I'm not necessarily only competing with competitors in my market or in my industry. I'm competing for total share of wallet for anybody that's out there. So, so fighting for a dollar of investment from a company is really, really tough, so that's for sure. But it goes back to the strength of the value proposition and the business challenge that you're a Trying, um, to be able to solve or how you're improving the company or the unique outcomes that people are have total spend management in the way with Rex is approaching. It is one of the last financial frontiers that organizations have yet to tackle in a really comprehensive and strategic way. So those people that manage some portion or all of that business process are looking for ways to be able to contribute to their own organization in their own culture and being able to do that. So it's, Figuring out what and how that happens. Now, the uniqueness about this, Harry, is the fact that, um, the pattern in which a lead, like, transforms into an actual demand and then gets into a campaign is much harder. So, maybe five, seven years ago, you used to touch an individual four times or five times, but, or they would convert into wanting to learn more about your business. Now we're up to like, 16 or 20 times to be able to do that. So, it's just making sure you're putting these process…

AI assessment note: “Yes. Well, first of all, yeah, money is tight”