Doug Adamic: Why Discounting is BS; How to Reduce Sales Cycles and Create Urgency | E1058

1. 0:00 – 9:22

   Doug Adamic’s Sales Journey

   1. HSHarry Stebbings0:00

      You scaled orgs to over 600 people.

   2. DADoug Adamic0:02

      During the time at Brex, I built eight new business departments that didn't exist.

   3. HSHarry Stebbings0:08

      Doug, I am so excited for this. I spoke to many, many people ahead of this conversation, so thank you so much for joining me today.

   4. DADoug Adamic0:16

      No, thank you, Harry. It's awesome to be here, and I'm so psyched to, uh, have a chat with you.

   5. HSHarry Stebbings0:20

      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?

   6. DADoug Adamic0:35

      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 a 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.

   7. HSHarry Stebbings1:11

      Can I ask you a bit of a weird one? Do you think sales-

   8. DADoug Adamic1:13

      Yeah, sure.

   9. HSHarry Stebbings1:14

      ... is something you fall in love with and it's very obvious, or do you think it's something you learn to love when you see the intricacy and the detail and nuance of it?

   10. DADoug Adamic1:22

       It's probably the latter. I think you need to be, have an entrepreneurial spirit in general to go into sales, um, but I think once you understand what sales is all about, improving a- a customer's business by driving specific outcomes, you recognize how complex it is, how intricate it is, and how rewarding it can be. So, I definitely think it's something that can be learned over time.

   11. HSHarry Stebbings1:48

       Now, 16 years at SAP. I mean, Doug, this is like a feat that not many people do in terms of longevity-

   12. DADoug Adamic1:55

       (laughs)

   13. HSHarry Stebbings1:55

       ... at one company. My question is, what are one to two of your biggest takeaways from 16 years at SAP?

   14. DADoug Adamic2:04

       So, the 16 years was broken up into two, like, distinct chapters. One chapter was growing up in, uh, a company called Concur, um, and, um, I joined when we were about 500 people and about $50 or $60 million in sales, um, and we grew that 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.

   15. HSHarry Stebbings2:59

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

   16. DADoug Adamic3:11

       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 has 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, a- 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 understand what the functional purpose is, how it connects with one another, and what we're trying to do for the customer journey and experience. It's been, uh, re- really a- a tremendous journey, uh, the entire time.

   17. HSHarry Stebbings4:48

       Now, we are gonna move to the schedule, I promise, that we did agree on.

   18. DADoug Adamic4:51

       Yes (laughs) .

   19. HSHarry Stebbings4:52

       But I'm- I'm fascinated, but you just said there about discovery, and o- one of my calls in particular on you said that Doug doesn't realize how brilliant a listener he is. He asks questions and listens. He asks another and listens, and in total, he says about 50 words in an hour-long call. And I just thought, how do you reflect on what makes a good listener, and how do you advise salespeople, reps, leaders on what makes great listening in sales?

   20. DADoug Adamic5:19

       It's funny because I've been asked this before. My feeling is, is that, at least for me, I am really interested in how other people perform their work, how businesses operate, and I am really, really purposeful and passionate about whether or not my involvement in their lives can improve their job or improve their business by being able to drive outcomes that they otherwise would not have been able to do. So, when I'm listening, I'm actually super interested to see whether or not, um, the individual, the group, the department, the company is experiencing something where I believe I can lean in and be able to help. And to do that, you actually have to be really in the moment. You have to be super mindful. You have to get rid of all of your preconceived notions, and you just have to be centered. And when you do that, you actually connect extraordinarily with people from all different walks of life, at all different levels, and all different, you know, whatever, um, to be able to do that. And when you pull it all together, then you really find the fact that you are truly trying to help somebody, and improve their lives, and create these relationships, and then lean in on it, and that's what's the best part of it.

   21. HSHarry Stebbings6:33

       Do you record sales calls?

   22. DADoug Adamic6:36

       ... I, I do. Yes, of course.

   23. HSHarry Stebbings6:38

       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?

   24. DADoug Adamic6:44

       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 in doing that?

   25. HSHarry Stebbings7:37

       Mm-hmm.

   26. DADoug Adamic7:37

       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 tick-tock pattern along the way.

   27. HSHarry Stebbings7:46

       I could... I, I could keep going on that train, but I'm like, "Shit. I need to actually focus."

   28. DADoug Adamic7:51

       (laughs)

   29. HSHarry Stebbings7:51

       (laughs) Uh, ha. But, but I had so many great quotes that you say, uh, and I called it the aphorisms of Doug, uh, which I love as a title for this, by the way.

   30. DADoug Adamic8:00

       Oh, no. Okay.
2. 9:22 – 17:33

   Creating Effective Sales Goals

   1. HSHarry Stebbings9:22

      I ask you, how do you think about effective goal-setting against pipeline that actually ties back to revenue? 'Cause 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-

   2. DADoug Adamic9:37

      (laughs)

   3. HSHarry Stebbings9:37

      ... (laughs) and it creates no dollars.

   4. DADoug Adamic9:40

      (laughs)

   5. HSHarry Stebbings9:40

      How do you think about creating effective goals that tie to revenue?

   6. DADoug Adamic9:45

      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 partner, 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 to be able to have better pipelines. So the, the goal would be not to create... Everyone talks about like, "We need that 5X pipeline, we need that 7X pipeline in order to make your goals." Not necessarily. When I left Concur and where I'm trying to drive Brex is we had less than 1X 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 pr- proper pipeline to be able to do those kinds of things.

   7. HSHarry Stebbings11:09

      Mm-hmm.

   8. DADoug Adamic11:09

      So in, in, in that is where we're trying to get to. It's not... It's not the abundance of pipeline, it's the quality of the pipeline from source, by conversion, by channel, and then you can be able to dial in from there.

   9. HSHarry Stebbings11:22

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

   10. DADoug Adamic11:31

       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 all the leads when they come in and accuracy in the data hygiene of that. So you have to make sure that people are, 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.

   11. HSHarry Stebbings12:31

       Doug, what do you do... I'm thinking about demand creation, uh, and you were like, "Whoa! I didn't sign up for these wayward questions, (laughs) but I'm going for them anyway." Um-

   12. DADoug Adamic12:39

       Okay, go ahead.

   13. HSHarry Stebbings12:40

       Demand creation in 2023 is much harder than in 2021 especially.

   14. DADoug Adamic12:45

       Mm-hmm.

   15. HSHarry Stebbings12:46

       What do you say to teams in tougher years where demand is not as abundant as it was?

   16. DADoug Adamic12:54

       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 a..." I think that those are the best times to create com- duh, 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.

   17. HSHarry Stebbings13:58

       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 there's almost this closed-mindedness to any so- form of new vendor. Do you find that?

   18. DADoug Adamic14:10

       Uh, yes. Well, s- 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 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 and the way in which Brex 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 and their own culture in 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 had, used to touch an individual four times or five times be- before they would convert into wanting to learn more about your bus- 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 processes in place and understanding the patterns that happen, and don't get too, you know, herky-jerky in getting too early because you'll fling them off the hook. You've got to let it set a little bit and then get them at the right time, and just understanding that.

   19. HSHarry Stebbings15:52

       Can I title the episode, "Don't Get Too Herky-Jerky"?

   20. DADoug Adamic15:55

       (laughs)

   21. HSHarry Stebbings15:55

       (laughs) That is excellent. I've never heard that saying before. That's fantastic. Okay.

   22. DADoug Adamic16:00

       All right. Well, see, that's why I have ............................

   23. HSHarry Stebbings16:02

       I mean, that's brilliant. Uh, uh, listen, the next one is threading multiple needles with one toss of the thread.

   24. DADoug Adamic16:10

       Mm-hmm.

   25. HSHarry Stebbings16:10

       What did you mean by this? Can you unpack this one?

   26. DADoug Adamic16:13

       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 leading towards something that you want to get done." So, I always make that thing, like, 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 and the company that you're actually trying to serve a, a complete disservice.

   27. HSHarry Stebbings17:32

       Can I ask,

3. 17:33 – 35:45

   Unlocking the Art of Sales Discovery

   1. HSHarry Stebbings17:33

      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?

   2. DADoug Adamic17:47

      So, there's a cou- 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, for Brex, implemented something similar to Brex, and then just listen. (laughs) 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 who, that's gonna 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 are 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 ............................

   3. HSHarry Stebbings19:00

      Mm-hmm.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, it always feels kind of dehumanizing and, uh, people know that you're trying to do it. How do you create multiple champions without transactionalizing it?

   4. DADoug Adamic19:21

      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 wanna 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 the, that, their thinking or maybe even lead them to something that they didn't know was broken or that they didn't recognize in the first place.

   5. HSHarry Stebbings20:54

      Do you find constructive tension is more welcomed in younger startup/technology companies versus when you're selling to Audi, Deloitte, corporates?

   6. DADoug Adamic21:05

      No, I, I, you know, it's interesting. I would say that both are difficult to be able to pull off. Both have characteristics that are very similar. The larger organizations have m- much more complex layers to it, politics, um, history, (laughs) things like that. And when you're dealing with, you know, more startup organizations or newer organizations, it's not more, it's not easier, (laughs) um, but it's just a different pattern, um, but they both exist and you have to fight through it in both, both situations.

   7. HSHarry Stebbings21:37

      Take more trips to the bank to make bigger deposits. (laughs) Uh, I was like, okay. Again, this was...

   8. DADoug Adamic21:46

      (laughs)

   9. HSHarry Stebbings21:46

      I, I was reading these when I was doing the research.

   10. DADoug Adamic21:47

       That's so funny.

   11. HSHarry Stebbings21:48

       And I was like-

   12. DADoug Adamic21:48

       That's so funny.

   13. HSHarry Stebbings21:49

       "...Fuck, they're not giving me a lot of hints, are they?"

   14. DADoug Adamic21:52

       (laughs)

   15. HSHarry Stebbings21:52

       So what does take more trips to the bank to make bigger deposits mean?

   16. DADoug Adamic21:56

       So when you're talking with salespeople, one of the things, (laughs) uh, this is gonna 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." (laughs) 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 is," 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 and the playbook that we've 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, of motivating and, and helping articulate that to salespeople.

   17. HSHarry Stebbings23:27

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

   18. DADoug Adamic23:35

       I think, I think what ma- 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 wanna come over and understand how to reduce that drag, how to be able to get more frictionless, uh, activity in your business so you can be able to do that." So it's a constant feedback loop in there.

   19. HSHarry Stebbings24:40

       Can I ask, how do you think about increasing urgency in a sales process? Most things are not like hair on fire, but, 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?

   20. DADoug Adamic25:00

       Yeah. So the best way, the, 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 gonna 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 Brex sells, un- 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've 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 there is an issue that requires immediate triaging right now, whether there are precursors or the beginnings of an issue that could come down the way, or maybe there's individuals that have joined the organization that are looking for transformation. So, there's only three reasons why an organization will make a purchase. They're in trouble right now, they see trouble coming, or an individual or group wants to be made a hero and get ahead of something. So, the only thing you're trying to figure out is how to be able to do that. And most of the time, it creates enough compelling event.

   21. HSHarry Stebbings27:00

       Doug, we have 70,000 sales leaders that listen to the show now, I think.

   22. DADoug Adamic27:05

       Yeah.

   23. HSHarry Stebbings27:05

       My question to you is... A lot say to me, "Discounting, should we do it to get that urgency?" It's kind of an easy hack/lever. From your many years of (laughs) incredible experience, how would you advise them listening on discounting and whether it is a good lever to get that urgency?

   24. DADoug Adamic27:23

       So, discounting is a difficult thing because you always want to be... You always want to charge what is fair for the value that you're bringing. And if you did the work upfront to establish that value, then salespeople and their leaders should feel confident in standing up for that. Discounting and creating, um, that kind of buying pattern for your organization or for your service sort of is, is, is going to set a bad precedent. Again, if I go back to what we were talking about before about going to the bank and making bigger deposits, there are a few things that a rep needs to consider in order to do that. How do I increase my average deal size? How do I shrink my cycle time? And how do I make sure that I have more units in my pipeline that are converting at a higher rate? Discounting or playing shenanigans or games is only going to demean that. Because if you did your discovery and established yourself correctly, then this is the fair value for what it is, and you should be able to continue that constructive tension in being able to command that, provided your organization delivers on that promise over and over again. Brex, for instance, has been able to deliver on that over and over again. So, I don't feel as though I need to overly discount in order to be able, um, to add value to an organization or create that compelling event in general.

   25. HSHarry Stebbings28:57

       "Lengthen your stride and quicken your step." We're gonna write a book together, actually. I can be your agent.

   26. DADoug Adamic29:04

       (laughs)

   27. HSHarry Stebbings29:04

       Um, these are great chapters. Um, what does lengthen your stride and quicken your step mean?

   28. DADoug Adamic29:09

       All of these statements...

   29. HSHarry Stebbings29:11

       (laughs)

   30. DADoug Adamic29:11

       So that you've somehow found. Um, have, um, all going back to the fact 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, the- 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, ha- 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, or what- whatever, to go faster in this world, which is you have to lengthen 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 tooling to make that happen over and over again. That reveals itself differently in different teams, but that's the concept of it.
4. 35:45 – 41:42

   The Perfect Sales Playbook

   1. DADoug Adamic35:45

      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, um, are too disruptive to introduce in a quarterly basis, so we'll take those half year or full year. So it's like a really, w- 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 dis- don't disrupt the business continuity and the motions that are going on a regular basis.

   2. HSHarry Stebbings36:14

      Doug, when you think about the start of a quarter, I think to Wolf of Wall Street, you know, Leonardo DiCaprio kind of-

   3. NANarrator36:19

      (laughs)

   4. HSHarry Stebbings36:20

      ... "I'm- I'm not fucking leaving" style.

   5. DADoug Adamic36:22

      (laughs)

   6. HSHarry Stebbings36:22

      What do you, what do you do to encourage, inspire a team to go chase a quarter like they've never chased it before?

   7. DADoug Adamic36:31

      Most of the time, people have personal goals or aspirations that are going to require some level of funding (laughs) 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 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, 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 much as I like Wolf of Wall Street and banging on your chest, it's so much deeper and so much more soulful for that, especially if you're trying to build an infinite, um, you know, sustainable organization where my daughters' kids would want to work at. And that's a different mindset, uh, moving forward.

   8. HSHarry Stebbings38:27

      Do you as a sales leader, and do the CEOs, do they always need to be involved in the massive sales moving forward, do you think? Is that forever a part of business?

   9. DADoug Adamic38:38

      Yeah. I think that there are always going to be marquee organizations that are going to, um, require a level of attention or connectivity to, um, a company at that level, but if I'm holding myself accountable as a CRO, we will want to have executive sponsorship with all of our marquee organizations, but it doesn't necessarily mean that it needs to be the CEO every single time. However, I do believe that the executive leadership team has a responsibility in the go-to-market and sales process to be able to represent the organization for these larger more marquee companies. But you want to load balance that out across the leadership team.

   10. HSHarry Stebbings39:20

       And speaking of, kind of those big contracts, when you get them, I think the hardest thing is actually the handoff to CS.

   11. DADoug Adamic39:27

       Sure.

   12. HSHarry Stebbings39:27

       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.

   13. DADoug Adamic39:36

       Yeah, yeah.

   14. HSHarry Stebbings39:37

       How do you do the handoff well, do you think?

   15. DADoug Adamic39:41

       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, 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 gonna 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 only thing the customer success person is doing is saying, "We made a promise to you, you made a promise to us, it's governed by these rules and it's this outcome. Now let's go get it." And we just go in, and we just make sure that that happens, have business reviews, readouts, and making sure that we're tracking towards the delivery of the promise that we made to them. If I do that, and if I do that consistently, I earn the trust to be able to ask for solving another business problem, making another promise, and when that flywheel starts to happen, that's when the customer relationship, that's when that really starts to make a material difference and becomes a competitive advantage, um, in the market.

5. 41:42 – 50:10

   Today’s Sales Environment

   1. DADoug Adamic41:42

   2. HSHarry Stebbings41:42

      Can I ask, I had Henry from ZoomInfo on 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 add 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 these expanses- expansive needs of, like, proof.

   3. DADoug Adamic42:06

      Yes.

   4. HSHarry Stebbings42:06

      Are you seeing that too?

   5. DADoug Adamic42:08

      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 Brex versus actually serving the customer, then all trust is lost. So what you're cal- currently or 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 in 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.

   6. HSHarry Stebbings43:20

      I'm always fascinated by deal reviews when we speak about, kind of, expansions there, and then also bluntly, 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 me?

   7. DADoug Adamic43:34

      So I normally have the front-line 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 s- same area.

   8. HSHarry Stebbings44:40

      What's a good reason to lose a deal?

   9. DADoug Adamic44:43

      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. (laughs) 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?

   10. HSHarry Stebbings45:33

       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?" And I say, "Ah, we didn't get it." And then-

   11. DADoug Adamic45:43

       Right. So-

   12. HSHarry Stebbings45:44

       ... I told you why, what would you get an-

   13. DADoug Adamic45:44

       There's-

   14. HSHarry Stebbings45:45

       Yeah.

   15. DADoug Adamic45:46

       Yeah. So there's one... This is 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 way. 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 realize 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.

   16. HSHarry Stebbings46:43

       Do you think that's fair? And I don't mean that, uh, like, uh, to push back, but like say everything's going great, you know, the 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 gonna spend anything. We're not gonna 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?

   17. DADoug Adamic47:14

       Yeah. So I guess, I guess it would be in the anticipation and the understanding of whether or not that organization was in a, uh, 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, c- 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 gate, A. B, if, if the value proposition is weak enough where even a shift in that is gonna 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 gonna have on the organization against what the controllable or uncontrollable event is going to be.

   18. HSHarry Stebbings48:28

       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."

   19. DADoug Adamic48:40

       Mm-hmm.

   20. HSHarry Stebbings48:40

       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"?

   21. DADoug Adamic48:47

       Well, so, so the reality is you can't close every deal every quarter, and not everything is always gonna go your way. So th- 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 a 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 gonna clo- are, are, are always gonna be able to pushout. 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.

   22. HSHarry Stebbings50:09

       Can

6. 50:10 – 58:54

   Hardest Part of Being CRO

   1. HSHarry Stebbings50:10

      I ask you, Doug, everything you say is very structured, logical and rational.

   2. DADoug Adamic50:14

      (laughs)

   3. HSHarry Stebbings50:15

      And it just seems so kind of in place. What's the hardest part about being kind of the revenue leader that you are?

   4. DADoug Adamic50:21

      Uh, you know, I think that one of the, one of the joys about this is that, as, 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 in 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 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 intera- interfacing with tens of thousands of individuals at companies, um, I think that that level of human unpredictability is the piece that, um, you know, sort of like bleeds into it a bit.

   5. HSHarry Stebbings51:20

      How have you changed most as a sales leader?

   6. DADoug Adamic51:24

      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, um, joy in building, um, systems and departments and infrastructure where the output or the result of the byproduct of that is always crushing your quota. 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.

   7. HSHarry Stebbings52:23

      Would you rather have someone who 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? Like a c-

   8. DADoug Adamic52:38

      Yeah, yeah. I think it's... (sighs) 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. So in, for instance, to the office of the CFO or maybe some- something tangential to, uh, total spend management or spend, spent management, uh, because there needs to be that, um, experience and expertise that exists within the sales force. 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.

   9. HSHarry Stebbings53:59

      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?

   10. DADoug Adamic54:07

       I think what I've seen is that they rely too heavily on the salesperson 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 s- uh, founders, um, underestimate the supporting cast of characters, and tooling and expertise and enablement that has to accompany a salesperson. A salesperson unto 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 gonna help them understand what to do is, is shortsighted, to be honest.

   11. HSHarry Stebbings55:12

       Do you think AI will change sales very quickly?

   12. DADoug Adamic55:14

       Oh, my gosh, yes. I think that, you know, I think that we're already seeing it in the way in which w- we talked about it earlier, dissecting sales calls, looking for patterns, uh, speech recognition, keywords, being able, um, to, uh, do outreach, the marketing process, how to be able to engage, what to be able to key on. It's going to transform...... how, and what, and why we go about doing our business, um, in the very near future, for sure.

   13. HSHarry Stebbings55:45

       Does that excite you?

   14. DADoug Adamic55:47

       Totally. Anything to be able to reduce drag and friction so people can be more effective in their movements, to go to the bank, to make bigger deposits on a more regular basis, I'm all in for because this is a tr- this is a tremendous profession, um, that is ripe for innovation and change. But it's also a very necessary process for very complicated multi-product solution-based sales. It's very difficult to remove the human aspect but if we can be more effective in it, um, then it's only gonna serve both sides of the, of the table perfectly well.

   15. HSHarry Stebbings56:23

       Doug, I wanna move into a quick fire round. So I say a short statement-

   16. DADoug Adamic56:26

       Okay.

   17. HSHarry Stebbings56:26

       ... you give me your-

   18. DADoug Adamic56:27

       Go ahead. Go ahead.

   19. HSHarry Stebbings56:27

       ... thoughts. We said there-

   20. DADoug Adamic56:28

       Go a-

   21. HSHarry Stebbings56:29

       ... about kind of changing nature of the profession. What sales tactics have not changed over the last five years?

   22. DADoug Adamic56:36

       Uh, selling value, in my opinion, for sure.

   23. HSHarry Stebbings56:40

       What have-

   24. DADoug Adamic56:40

       Like, you-

   25. HSHarry Stebbings56:41

       What have totally-

   26. DADoug Adamic56:42

       Go ahead.

   27. HSHarry Stebbings56:43

       ... changed?

   28. DADoug Adamic56:45

       Um, I think leading with, uh, features and functionality. I think that buyers are getting much smarter now and, um, when you come in and you just start demo-ing or showing features and functionality, that may have worked a while back when new innovation was happening but there's so much innovation right now, I go back to my first answer. Now the thing that hasn't changed, selling value. The thing that has, leading with your product, with feature and functionality.

   29. HSHarry Stebbings57:10

       Does the old school enterprise sale, go to the Taylor Swift concert, the Super Bowl, does that still work?

   30. DADoug Adamic57:17

       Not as much. The only reason being is most organizations now have policies in 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 the company or the individual that I'm dealing with, but what we're seeing is that customers will value them, you challenging their, um, 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.
7. 58:54 – 1:01:36

   Quick-Fire Round

   1. DADoug Adamic58:54

      salespeople are smarmy or like something-

   2. HSHarry Stebbings58:57

      (laughs) .

   3. DADoug Adamic58:57

      ... like that. Like, I, I, I, I view sales and the world of sales as being really, really great consultants that help drive businesses improving and have a huge impact in helping companies become more competitive or achieve goals that they never have before. So if we can change the perspective that a sales guy's a people person or a smarmy kind of thing, then that would be huge.

   4. HSHarry Stebbings59:23

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

   5. DADoug Adamic59:32

      If a quarter is missed, um, you need to do something about it. 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 success is 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 ad- adhering to the system, the process, and the playbook, then we know we're gonna 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 gonna pay off in the long term.

   6. HSHarry Stebbings1:00:17

      Final one.

   7. DADoug Adamic1:00:19

      Yeah.

   8. HSHarry Stebbings1:00:19

      What company strategy most recently have you been super impressed by in terms of their sales strategy?

   9. DADoug Adamic1:00:25

      Well, you know, and this is... I know that this is maybe a cop-out but, um, I still am impressed by salesforce.com and how they go about getting business. How they sell value, the way in which they create an experience, and a customer success motion for the companies that they have. The breadth and depth of how they can add value and serve a customer and the impact that it can make. Um, I think that that still, um, is like sort of a gold standard for what I think has been very, very impressive and something that I, I'll strive for, uh, to be honest with you as I construct my, my business.

   10. HSHarry Stebbings1:01:08

       Doug, listen. As I said, I spoke to nine people before this. I heard the most wonderful things. This has been a fantastic-

   11. DADoug Adamic1:01:13

       (laughs)

   12. HSHarry Stebbings1:01:13

       ... discussion. So thank you so much for joining me today and I've loved talking.

   13. DADoug Adamic1:01:17

       Thank you so much, Harry. This has been a blast. Um, I love getting to know you. The questions were great. Thank you for your hard work and investment and all of the time and research to be able to do it. The fact that you talked to people and had aphorisms for me was, uh, a little shocking but really, really good. Great job. Thank you.

   14. HSHarry Stebbings1:01:34

       Dude, I loved it. Thank you so much for that-

Episode duration: 1:01:36