Cold open
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.
I mean, what an incredible start there. I don’t think there’s ever been a more important time for sales teams to understand what it takes to unlock revenue in tech companies today and unlock the buying of software. This is 20 sales,
Intro
the monthly show where we sit down with the best sales leaders in the world to reveal their tips, tactics and strategies when it comes to starting and scaling sales teams. And today I’m so thrilled to be joined by Doug Adamic, CRO at Brex, where he leads the company’s revenue and growth strategy. Prior to Brex, Doug was Chief Revenue Officer at SAP Concur. And during his sixteen year tenure, he oversaw an organization of 600 employees and was responsible for all aspects of revenue, generating go to market strategies and departments.
But before we dive into the show
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Conversation
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.
No, thank you, Harry. It’s awesome to be here and I’m so psyched to have a chat with you.
I love a little bit of context. Sales is something that often I hear people fall in love with. When did you fall in love with sales first and what was that entry point for you?
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 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 company called Cintas. I don’t sure if you’ve heard of them before, but 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. I think you need to have an entrepreneurial spirit to go into sales. But I think once you understand what sales is all about, improving 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.
Can I ask? 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. How do you reflect on what makes a good listener? And how do you advise sales people, reps, leaders on what makes great listening in sales?
It’s funny because I’ve been asked this before. My feeling is is that I am really interested in how other people perform their work, how businesses operate. 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 they otherwise would not have been able to do. So when I’m listening, I’m actually super interested to see whether or not 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 whatever 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.
Do you record sales calls?
I do. Yes. of course.
And how do you do them in terms of reviews as a team? I’m just fascinated. Do you do coaching on those sales calls?
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 a unique 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.
I could I could keep going on that train, but I’m like, shit, I need to actually But But I had so many great quotes that you say, and I called it the aphorisms of Doug, which I love as a title.
Oh, no.
Okay. And so number one is pipeline is our air. Without it, we die. Can you unpack this for me and what you mean by that?
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 responsible for pipeline. And to a degree, that’s correct. However, everyone’s responsibility is demand creation. I have three major objectives that I tie my entire go to market distribution team to. One is advanced demand creation. Two is the profitable conversion of that pipeline. And then three is the protection and growth of our customer base. So when I say pipeline is our air, I say that everybody has to contribute to building demand.
And if you don’t, then we’re 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 that is why I say that this is our air. 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.
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. you no no dollars. How do you think about creating effective goals that tie to revenue?
If we’re speaking about pipeline, then first I begin with the source by which the pipeline is created. That can be inbound, that can be partner, that can be self generated, 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 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 goal 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 pipeline. So the goal would be not to create everyone talks about like you need to have 5x pipeline, you need to have 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 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 things. So in that is where we’re trying to get to 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.
What do you think drives quality? Is it super tight ICPs with very strong discovery processes? What is it that drives that high quality?
So 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, 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.
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 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.
Doug, what do you do when thinking Can demand creation? And you’re like, whoa, I didn’t sign up for these wayward questions, but I’m going for them anyway.
Okay, go ahead.
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?
Well, first of all, I struggle with that comment inherently because 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 going through that because of the times that they’re in.
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. And And it’s almost as closed mindedness to any sort of form of new vendor. Do you find that?
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 fighting for a dollar of investment from a company is really, really, tough. So that’s for sure. Now the uniqueness about this, Harry, is the fact that 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 before 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 processes in place and understanding the patterns that happen, and don’t get too herky jerky and getting too early because you’ll fling them off the hook. You’ve to let it set a little bit and then get them at the right time and just understanding that.
Can I title the episode, don’t get too herky jerky? I’ve never heard that saying before. That’s fantastic.
Well, see, that’s why I have aphorism.
Brilliant. 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?
Yeah. So when I’m talking with 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 hello. Right? And so you have this thread and in order to get a deal done, 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 to just convince the CFO, or I just have to convince the vice president of finance or control it.
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. 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 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 and the company that you’re actually trying to serve a complete disservice.
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?
Well, first of all, in a very, very, pragmatic sense, asking that individual the last time they 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 converts 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 that most often 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 to 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 in regards to that.
How do you think about creating multiple champions in the sales process? On paper, it sounds wonderful, but to be like, Doug, I love our chats. I’d love to meet the rest of your team. It always feels kind of dehumanizing and people know that you’re trying to do it. How do you create multiple champions without transactionalizing it?
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 continue to invest more discovery in or you to just cut bait and we don’t have an opportunity. The faster we can get to that, the more time we’ll save for one another.
So you have to be okay pushing the customer to be able to do something that they don’t want 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 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.
Do you find constructive tension is more welcomed in younger startup slash technology companies versus when you’re selling to Audi, Deloitte corporates?
No. 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 much more complex layers to it, politics, history, things like that. And when you’re dealing with more startup organizations or newer organizations, it’s not easier, but it’s just a different pattern. But they both exist and you have to fight through it in both both situations.
Take more trips to the bank to make deposits. Okay, again, this is I was reading these when I was doing the research, I was like I’m so for Fuck. They’re not giving me a lot of hints, are they? So does take more trips to the bank to make bigger deposits mean?
When you’re talking with salespeople, one of the things, this is going be a weird thing. One of the things that is incredibly important is for a salesperson to understand effectiveness in their movements are going to give them more capacity to be able to sell more. 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 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 and the playbook that we’re putting into place.
And until that doesn’t happen, you should always be able to lean into that. So this is sort of a philosophy on motivating and and helping articulate that to salespeople.
What do you think is the biggest challenge that salespeople have when they hear that? What’s the hardest next step for them?
I think that what manifests itself is sales reps, 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 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 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 if it’s taking me away, raise your hand. I to come over and understand how to reduce that drag, how to be able to get more frictionless activity in your business so you can be able to do that. So it’s a constant feedback loop in there.
How do you think about increasing urgency in a sales process? Most things are not like hair on fire. 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?
So 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 aphorisms. be the easiest way to be able to do that. 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. 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 for 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.
Doug, we have 70,000 sales leaders that listen to the show now, I think. 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 slash lever. How would you advise them listening on discounting and whether it is a good lever to get that urgency?
Discounting is a difficult thing because 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 that kind of buying pattern for your organization or for your service 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 and being able to command that, provided your organization delivers on that promise over and over again.
So I don’t feel as though I need to overly discount in order to be able to add value to an organization or create that compelling event in general.
Lengthen your stride and quicken your step. We’re to write a book together, actually. I can be your These are great chapters. What does lengthen your stride and quicken your step mean?
So all of these statements that you’ve somehow found have 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. These are things that you constantly have to think about, not just in your professional life, but in your personal life as well. So when I say this, like when quotas go up and territories shrink, have that’s the definition of growth, then the only way for you to be able to make more money is to go faster.
And there’s only two ways in the world, regardless of who you are, what age you are, what shape you are, whatever, to go faster in this world, which is you have to 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.
Why do you think the biggest bottlenecks are to the speed of those sales reps?
That’s a good question. I think depending on the company is how quickly they can understand what it is the purpose of the company is trying to do and what is the outcomes that a company is trying to elicit and how does that translate into improving a company’s business.
So if you don’t understand how to change the buying criteria to lead to your product rather than leading with your product, then I think that’s the biggest challenge, at least that I have in building and training a Salesforce is to refrain from being excited to talk about features and functionality and be more diligent in trying to understand how the company they’re talking to operates and where uniquely we can be able to help achieve their goals by being able to deliver measurable outcomes.
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, is sales playbook. When you think about sales playbooks, what does sales playbook mean to you when you hear that?
For me, 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 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 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 be able to deliver. So at the very highest level, steps in the process, checklists for each step, adhering to finishing that in order to go into the next one is really how I look at a playbook and how important that is to be able to do that.
How do you think about when’s the right time to transition between playbooks? You know, you scaled orgs to over 600 people. The playbook changes with stage from really pre PMF to finding early PMF Yep. to scaling into, you know, multi hundred people organizations. How do you know when’s the right time to change playbook?
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 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 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.
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 do to encourage, inspire a team to go chase a quarter like they’ve never chased it before?
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 advancement and a counterbalancing of that. So the very first thing, 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 are trying to achieve here. 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 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, you know, sustainable organization where my daughter’s kids would want work at. And that’s a different mindset moving forward.
Do you as a sales leader and to the CEOs, do they always need to be involved in the massive sales moving forward, you think? Is that forever a part of business?
Yeah, I think that there are always going to be marquee organizations that are going to require a level of attention or connectivity to 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 to load balance that out across the leadership team.
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. Yeah. How do you do the handoff? well, do you think?
It begins with taking a look at the entire customer life cycle from beginning where we create awareness, 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 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. 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 in the market.
ask, I had Henry from Zoom on the show and he said the hard thing about this time is before you just have people call and they would upsell, let pay and 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?
100%. Yes. You’re only as good as the last promise you made and fulfilled with an organization, making sure that you’re driving business outcomes that are important to the company, not for you. The second a customer thinks you’re 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 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 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, expansions, purchase of other products or categories of products are a byproduct of doing all of this other stuff really, really, well.
I’m always fascinated by deal reviews when we spoke 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 you?
So I normally have the frontline managers 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 talks about 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? What kind of data have we received? What’s the topography of their infrastructure?
How are we creating a path to be able to help them conclude the process? Hopefully, they buy us, but maybe they don’t. 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 state same area. What’s a good reason to lose a deal? I think that if they don’t have a business problem that we uniquely solve, you don’t to jam something down their throat because you’re only going to have a terrible customer success implementation process down the road.
There are non controllable things that happen. People go out of business, people get bought, 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. 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.
What’s a bad reason for not winning a deal? If we had a deal review and you said, how did that deal go? I say, yeah, we didn’t get it.
The only reason 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, 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.
Do you think that’s fair? And I don’t mean that 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 going 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?
I guess it would be in the anticipation and the understanding of whether or not that organization was in a point where they needed more funding or they were doing, like, to not know what the financial aspect or pattern is of the organization you’re selling to is inexcusable. And then two, yeah, 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 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 the value proposition is weak enough where even a shift in that is going throw this 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 the depth of the value proposition and the impact we’re going have on the organization against what the controllable or uncontrollable event is going to be.
I sit on many boards and the common thing that I hear is, ah, Doug, we didn’t hit the numbers because you know what? It just slipped to next quarter. It’s gonna happen, but it just slipped to next quarter. And I never know what to say. What would you say if you were in a board and they say, ah, slipped to next quarter?
The reality is you can’t close everything every quarter and not everything is always to go your way. So this is always going to happen. However, it is materially triaged when the sales rep and the entire team understands the timeline that we’re 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 and how this is going to 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 always going to be able to push up. But having proper close plans, setting that expectation 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.
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?
I think that as prepared as you can be and as organized or as thoughtful that you can be, it’s still people. And we are a human wrapper around a world class product, and we interface with all types of individuals and all different levels within the 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 interfacing with tens of thousands of individuals at companies, I think that that level of human unpredictability is the piece that, you know, sort of like bleeds into it a bit.
How have you changed most as a sales leader?
When I was younger, I used to think being a great sales leader was always being at the top of the leaderboard. And now I find joy in building 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 my family, we have a saying, it’s not the box score that 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.
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? Like I said,
yeah. Yeah. I think it’s the 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 the right kinds of individuals that have some industry experience in what we do. selling, for instance, to the office of the CFO or maybe something tangential to total spend management or spend management, Because there needs to be that experience and expertise that exists within the Salesforce.
But like Brex, 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 sales campaigns and structure and and distribution models, in my opinion.
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?
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 the sales campaign. So I think that founders 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 are to help them understand what to do is is shortsighted, to be honest.
Do you think AI will change sales very
quickly? Oh my gosh, yes. I think that we’re already seeing it in the way in which we talked about it earlier, dissecting sales calls, looking for patterns, speech recognition, keywords, being able to do outreach, the marketing process, how to be able to engage, what to be able to key transform how and what and why we go about doing our business in the very near future for sure. Does that excite you? Totally.
Anything to be able to reduce drag and friction 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 tremendous profession that is ripe for innovation and change, but it’s also a very necessary process for very complicated multiproduct solution based sales. It’s very difficult to remove the human aspect, but if we can be more effective in it, then it’s only going serve both sides of the table perfectly well.
Doug, I want move into a quick fire round. So I say a short statement. You give me your immediate thoughts. We said there about kind of changing nature of the profession. What sales tactics have not changed over the last five years?
Selling value, in my opinion.
What have totally changed?
I think leading with features and functionality. I think that buyers are getting much smarter now. And when you come in and you just start demoing 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. Not the thing that hasn’t changed, selling value. The thing that has leading with your product with feature functionality.
Does the old school enterprise sale go to the Taylor Swift concert, Super Bowl? Does that still work?
Not as much. The only reason being is most organizations now have policies and being able to receive gifts 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 between myself as a salesperson and the company or the individual that I’m doing with. But what we’re seeing is that customers will value you challenging their ideas or their status quo by being able to bring insights 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.
Such a shame I was ready for that
I’m sorry.
I’m so sorry. Tell me, what one piece of advice would you give to a new sales leader starting a new job today?
Making sure that you understand what buying criteria needs to change with your prospects in order for that to lead to your product. If you don’t understand how you need to change the buying criteria to uniquely lead to your product, then you’re not setting yourself and your team up for success.
What would you most like to change about the world of sales, Doug?
Probably just the perspective that salespeople are smarmy or like, something like that. Like, 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.
How do you maintain morale when a quarter’s It’s a tough time. Sometimes a lot of work goes in and the quarter’s missed. How do you maintain morale?
If a quarter is missed, you need to do a deep dive. 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 the right, that would be sort of indicative of successes just around the corner. So let’s not make this a pattern. However, this is the stuff that we did wrong, but here’s a whole bunch of stuff that is going up and to the right. So if we adhere to this, don’t get rattled by getting a little bit of bad news and stay focused on adhering to the system, the process and the playbook, then we know we’re 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 to pay off in the long term.
Final one. What company strategy most recently have you been super impressed by in terms of their sales strategy?
I know that this is maybe a cop out, but 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. I think that that still is like sort of a gold standard for what I think has been very, very, impressive and something that I’ll strive for, to be honest with you, as I construct my my business.
Doug, listen. as I said, I spoke to nine people before this. I had the most wonderful things. This has been a fantastic discussion. So thank you so much for joining me today, and I’ve loved talking.
Thank you so much, Harry. This has been a blast. I love getting to know you. The questions are great. Thank you for your hard work and investment in all of the time and research to be able to do it. The fact that you talk to people and had aphorisms for me was a little shocking, but really, really, good. Great job. Thank you.
I just love that discussion. It was so much fun to have. I wanna say a huge thank you to Doug for being so willing to go off schedule there. If you’d like to see the full episode in video, you can check it out on twenty 20VC by searching for that on YouTube. But before we leave you today,
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