WHAT IS WORKING TODAY IN LARGE ENTERPRISE SALES
16 Feb 2026 · 48 min
Jay Douglas, a sales leader with 27 years in payroll and HR solutions, explains what works in enterprise deals. He argues for a written visual sales process, not checklists, and warns that emotional and political dynamics between procurement and economic approvers often stall deals. Near close, when things get turbulent, leading the deal matters more than process.
Chapters
On LinkedIn, I did a post on the sales leadership page asking, how many of you have a written sales process? And it was less than half said they did, and I think they were lying. I think they consider it what they have in the CRM as far as stages of a sale or a checklist like MedPic. That's not a sales process. That's the ingredients Of a sales process. When I say sales process, I mean, do you have a written visual way of presenting where you are and where you're going and what has to be done?
Okay.
Checklists give you the ingredients of a sales process. Doesn't tell you where you are and what you have to do other than the artifacts. And a lot of people say, well, we got to have a mutual action plan. Well, guess what? The other person is not responsible for buying your product. You're responsible for selling it. They're responsible for solving problems, getting their job done. So assigning them work may ruin your deal. And when I've tried that after I took that training, and it backfired every time. And I pretty much got rid of it and just Guide it, my client. Leading is kind of— you are leading. Somebody's leading the deal. Either you're leading it or the customer's leading it, and the customer doesn't know how to get it done. This is what I mean by a process, and this is what we're going to get into today's interview. And I sum it up with this one question: do you have a treasure map, or are you on a A treasure hunt. Here's the difference. We've all seen the movies. Nicolas Cage goes from clue to clue and hunting the treasure. You know, they open a desk drawer and underneath the— or in the back of the drawer is the clue to the next clue. And that's how a lot of people sell. They have little clues along the way. And they find They may find the gold, or they usually end up in the swamp or lost in the no decision category. Now, there's other people that have a treasure map. It tells you where to go, what to avoid, where the swamps and the traps are, and where the treasure is and the easiest way to get there. Now, I talk about this a little bit in the interview, but The epiphany that I had in the large complex sale is I got away from the treasure hunt. Because I saw a lot of reps sitting down trying to interpret these clues. What do you think they meant by this? What do you think this email means? What do you think this request is going on? What's behind it? Instead, I go, why don't I have a treasure map? Because The deals that do get done look very different than the deals that don't get done. And what are the traps that we always fall into because our customer just pulls them into— us into it? They naturally fall into it and the deal doesn't happen.
And we are basically working for free.
This was one of the more enjoyable interviews I've had. I really connected with the guest, understood What they were saying. And this is one that I should charge for. Sorry, I have to. I have no way of doing that, so you get it for free. And if you want to learn how to build your treasure map, Winning the Complex Sale, it is game-changing for anybody who's in the large complex sale. Meaning that if you have, say, more than 3 influencers in your deal, maybe more than one department, if the dollar amount is, you know, $50K or above where it has to go pretty high in the company, where the default is to do nothing and doing nothing is an option, then you've got to take this course. It is the difference between you winning and losing the deal. So you just got to ask yourself this one question: do I want to win, and how bad do I want to win? Let's get into the interview. I'll sum it up at the end.
Hey, John, thanks for joining us. Sales, where are you getting started? Give us a little background on yourself.
Yeah. Hey, Brian, it's a pleasure. Thank you so much. Uh, let's see. So I'm, uh, I'm gonna date myself right out of the gate and tell you that, uh, I've been in sales for about 27 years. Um, I started with the illustrious career of going door to door in office buildings and selling fax machines and presentation systems. My first boss, who's a great guy and had a really interesting and unique voice, dropped a phone book on the desk and said, JD, here's your leads. And that's how I started. And I survived sales for a year. And after that, after all those lessons in resilience, I actually decided I might make a career out of this thing. And it was a great experience. And I moved from there into really a number of different areas in payroll sales, payroll services sales, into the burgeoning at the time online workforce management space, but right when the internet was developing applications where people could hire on the web. And I've spent the rest of my career now working with large multinational organizations, really focused on the human capital management chain and obviously retaining, maintaining, and attracting all that talent and all the international complications that revolve around that. So it's been a fun run.
So you've always taken the easy route out?
Oh yeah, yeah, it's, it's been a cakewalk.
Just luck and timing.
But as you know, sales is easy, so, you know, it's always easy, right?
Uh, yeah.
I'm being facetious.
Yeah, but what, what about that space do you like? Because you've had a long run.
I mean, for me, I, I don't know. My honest answer is I'm not sure I would know what else to do. Um, I, you know, some people faint thinking about a commission, trying to make a living through commissions. And I faint thinking about having something other than a variable paycheck. So I think I've always been drawn to the fact that I had a large modicum of control over my own destiny. And I don't know that I would be able to wake up and not look at a sales board and figure out whether I'm going to have a better year this year than next and how I can control that. So I just, I think it's an amazing profession. I'm really lucky I kind of fell into it, honestly.
And how have they kept you? Because the challenge, the math on staying in sales at the same company doesn't work out well, right? Because you do well, you get smaller territory, larger quota. You do well, you get smaller territory, larger quota. So after 3 or 4 iterations of that, I guess you've had different roles. Is that what's kept you there? I have.
So, you know, for, for the last, you know, at least 16, 17 years, I've thought every 3 years, I thought, where am I going to go? I'm out of room here to grow. But fortunately, I've been with a company whose culture is hugely focused on making sure that they retain their talent, move them into new roles, and we've just grown like crazy over that time span. So there's always been new challenges. And so it's been a really, especially in this day and age, as you know, a really rare privilege and pleasure to be able to do that and keep learning. And that's the important part. We all have to keep learning and growing. And that's not easy, to your point, at the same company, right?
It's not because you get comfortable or you get used to And you have that success and it's hard to keep the motor going in the same type of game.
Yeah, and I think, I think the key to that is constantly challenging yourself to approach things differently, challenging the organization sometimes to approach things differently. I mean, you've got the value of having these eyes and ears in the space for such a long period of time. To your point, though, the danger is that you get stagnant and you start to accept the status quo. And I think that's just a, that's a constant and that's a life thing too, right? We all have to continue to work to grow. Uh, but you know, again, the company has been so vibrant with so many new products and services for so long that, you know, they've, they've made it much easier than it could be.
And I'm sure you're exposed to a lot of reps over the years, good, bad, indifferent. What separates the very best from the okay?
Oh, you'll probably get a lot of, uh, different answers on this and some will overlap. You know, I think those that— first of all, you got to be genuine. So you have to have a sense of yourself. And I think just like in any profession, you need a strong level of self-awareness. So that allows you to operate with inside your box, but also know how to stretch that box.
Yeah.
Because if people sense or sniff, and people are smart, if they sense that you're not being who you are and you're not who you are, you're done. And I think the best salespeople even though their approaches, as you know, vary wildly, and there's all different kinds of successful salespeople, one of the things a lot of them have in common is they know who they are, and to a great extent, they're genuine. And then depending on the type of sale, as you know, whether it's transactional, long-term relationship, I think there's a foundation of really caring about the outcome for the client, having a good sense of humility when you need it, and really putting a long-term strategy and their goals first. And then I— it sounds cheesy, but I think everything else works out. You know, it does. And again, I'm speaking from the lens of my profession, which is different than some types of sales. These are very long-term complex sales. Sometimes the sales process takes years.
But I had this manager once who said, all you have to do is learn to fake authenticity. And I just laughed at him. I go, you realize that's an oxymoron?
Yeah, it kind of is. There's some good actors out there. I just don't know over the long term that that's really sustainable or a great way to live.
Well, that's it. Because, you know, his authenticness came out eventually. And he was, he was more the traditional talk about sports, relationship, let's go to lunch, dinner, ballgame type of guy. Didn't really get into the nitty-gritty of the deal or the people or the business.
Yeah.
And he did okay. You know, he wasn't the You know, he's my manager. I liked him. He was easy on me because I closed stuff. And but what you said about that authenticness, it's kind of a mix of— and you can correct me— confidence but not cockiness, right? Um, you kind of— you do your homework and you're a straight shooter. You, you don't try and I guess portray yourself as somebody that you're not or to put on that sales voice.
Yeah, I think so. I think you're right.
Yeah.
Um, and I think— and you talked about— I loved one of the things you discussed, you know, trust versus trustworthy and what that means. And to me, time plus experience has always equaled trust. So it's hard to be trustworthy out of the gate, but what you can do when you, when you meet somebody and you're trying to be authentic with you can set an expectation and before you even begin to do business, when you're considering it or at the beginning of a sales process, I think it's important to kind of lay down, hey, here's who I am. Who are you? How do you expect to be treated? Here's the way that I generally operate. I'm a super candid guy. And if you ever see that I'm not or believe I'm not, please call me out because I want to walk hand in hand throughout the entire process with you. I don't want to hold anything back. If there's a weakness or a concern in the model or my value proposition I'm offering, I'm going to point it out to you so you don't have to Go look for it. I want you to be able to understand that I may have a counter view as to why the— in the big picture, that's not a big deal. And in some cases, I may say, you know, we shouldn't pursue this. It's not right for you, even though I might be walking away from the process. Are you okay with that? How does that sound to you? And I think having that kind of dialogue open to start with, like, what do you— what do you want to see out of this process? So it's almost like you talk about interviews and interviewing somebody and helping guide them, as opposed to, you know, being back here on it. Like help instead of getting caught in the buying process later responding. Can you set the stage together with your client or your prospect and learn how to work through the process with them and gain agreement? To me, those types of conversations, when they're real honest and open, the sooner you can have them, the more you're establishing trust. And then after you do that, you better show up every day and do what you said you were gonna do.
That's awesome.
As soon as you don't, it's over. So, you know, that's a rant, but those are some of the things that come to mind when we get into a conversation like this.
Well, that's it, because I think trust is built by showing more interest in your client than your self-interest.
That's absolutely right. Always, always.
In business-to-business and the enterprise sale, there's no trickery, there's no gimmicks, you know, in the long term.
Yeah, and I agree.
Too many people think that selling is just what you say, but it's much more what you do.
It is, it is. And I mean, you can take that and blow it up to, again, like, some of the truisms of sales are so universal with everything. And, and I think, I think that's— those are the kind of things I try to instill in my kids to the extent I have that control as well. But I think it's really important in relationships, period.
And to build trust, it almost forces you to be curious about them, which forces you to put yourself in their position and say, what would they care about? Or is this not a priority? It shouldn't be a priority for them right now.
Absolutely. And if, if you're not doing that, you're doing yourself a disservice, because that's going to show up later after you've spent an awful lot of time working with somebody you shouldn't be working with on, on something that they shouldn't be spending time with you on. So You know, I'm just a huge fan in candid conversations and calling a spade a spade. And if you've, you know, if you've got issues, call them out because your client or your prospect's going to figure them out too, you know. So be honest.
And what's the hardest part of your sale?
Uh, in, in my world, I think a lot of folks would tell you, and I tend to agree, it's, it's the political landscape of navigating a large organization. So as you well know, You can put together the best laid plan for yourself and on behalf of your client, and the whole thing could be tracking, and there's 7 different committees that all line up to the C-level, and there's a new report that came out the next month in the financials. We gotta rejigger some things around. So there's so many things you can't control in these types of processes, and that's why I get back to, you know, I think some of the underrated qualities around salespeople, you know, patience has seemed as not to be a virtue often in sales. I want the impatient guy, the guy who's got to win, the guy who's got to close next month. But I really think that there's a time and place for that behavior and a type of sale where that's important. But in, again, and through the lens with which I view all this, patience is one of those underrated skills that you don't want to be patient in that you're not taking control of every action item that'll help move your sales process along and help your client get to the finish line and help your company get to the finish line. But my God, in my world, if you're not patient, you're done because you'll overstep your bounds. You want to hit your goals and you'll end up doing the wrong thing. We were talking about doing the right thing for the client. If you get too impatient, you'll do the wrong thing for your client or your prospects. So that's important to me too.
Well, that's it because so much of what you sell in the enterprise is they like it, they want it, they need it, they can afford it, but it still takes a lot more than that. And you don't think like that.
It does. There's that little game that I don't remember the name of it. When we say that, I think of the— there's a little BB and it's— this is probably such an old school game, but it's a pegboard and you're trying to land the little BB in a certain— and that's how it feels sometimes, the adult world of trying to manage a process like this. So many uncontrollables and you hit speed bumps constantly and you're readjusting all the time. And I think one of the value components of, you know, we were talking about being in a space for a long time and the challenge of staying crisp. But one of the, one of the great things about that is you tend to see it's almost like Brady on the football field. Terrible analogy because, you know, I don't know about you, but I'm not close to a Tom Brady. But, but you, when you're on the field long enough, you can see really, really well and you see things a mile away. And even when you're mentoring somebody, I think that's important. Like, one of the things that you bring to a mentoring opportunity with another younger salesperson or inexperienced salesperson, one outside the industry, I almost feel like— what's a good analogy? If you've been driving for a long time, let's say you're in the car with a student driver. They're just responding to stimuli. That's the new salesperson, right? In their turf, in their role, in their industry. But you're watching the lanes and you know that somebody's about to do something up ahead that's going to cause a major issue and you can see exactly what's going to happen and how you need to respond to stay out of trouble or to get by those cars. And I think that's some of the value of all this is we start to understand those processes so much better. We can manage that, that little ball coming down the chain better. We can keep people out of trouble sometimes. So I think, you know, there's a lot of value in that over time too, with experience.
Well, that's it, because nobody really teaches us the game board of large enterprise sales.
No. And if you could, if you could develop a sales training that could somehow take every complex sales industry complexity and do an if-and matrix, well, you'd be— it'd be unbelievable. But the variables are so crazy, right?
Well, that's it, because you either have a treasure map where you understand the little thing with the BB, you can see it. But in a lot, you can see it in a large deal because you've been through so many. But the new rep is on a treasure hunt. They're going from clue to clue, action to action, reaction. They said this, what do I do now? If, then, else.
Yep.
And this is what I— when I first would go into an account, I would get on the whiteboard and I go, okay, first meeting, what do you do in the first meeting? Then what happens? And I draw it out, and then we would get into the training. Because I had to understand.
I love that. Yeah, where it was.
But I wanted them to see the map, not, not just because otherwise it's like, okay, Brian, let's say they don't call you back.
What do you do then?
Right, right, right, right.
Or they tell me it's in procurement, but no one's answering the phone.
Yeah, exactly.
Yeah.
And these are real issues when you have 2 accounts or 5 accounts or 10 accounts. That's a real issue. If you've got a zip code with, you know, 10,000 businesses, it's okay if they don't call you back. Yeah, very different worlds.
How long did it take you to get comfortable in these larger deals?
You know, that's a great question. Um, I think, um, I'm— I try to be uncomfortable as much as possible. So I'm, I'm a believer in being practically paranoid. Um, as a sales rep and sometimes probably too much as a business person too. But I think it's important to really continue to realize that the landscape is always shifting and not be comfortable. So I don't know that I'll ever be entirely comfortable in the context of any situation or deal because I'm always looking at what's going to go wrong. I'm a little bit of a catastrophist, I guess, as it relates to that. But I will tell you that there were a few key deals that I had where I overcame a lot of objections to get to the endgame that probably allowed me to build that confidence. I think it's daunting when you first start to go into a boardroom and speak with a multifunctional team of decision-makers, many of which know so much more than you do as it relates to their profession. In a lot of ways, especially as you get more experience, you're bringing insight to them that they don't understand because you've got this world of other clients and prospects that you deal with, but that's daunting. So I think getting through the first few of those successfully. I think getting through real obstacles. I remember like my first— this kind of brings me back and it's also part of kind of thinking about mentorship now that we were talking about that. We'll call him Bork, but one of my first senior managers at my company, when I got my first big deal and I was a young, kind of a young, real young salesperson in that league or that world, saw me freaking out when we were getting into that, you know, 80% of the way there with the deal. This is a $3 million annual deal, probably over 7 years, $20 million, right? So it's— this is not a small deal for a, you know, for a relatively young salesperson. And how he helped me, and going back to your whiteboard thing, he dragged me into a room. Basically, I felt like a puppy, like by the scruff of my neck, and he pulled me into the room, just him and I, and he says, the VP of sales, like, you know, going out of his way to come down to my cubicle at the time and see how I was doing. And he proceeded— he knew everything about the deal. I had him involved. And he proceeded to draw an airplane on the board. And he said, here's your plane, right? You're cruising. Here's your altitude. You're doing fine.
You were here. You were here. You went here.
And now I know where you're at. And he started drawing a plane that's on fire, about to crash on the ground. He said, that's how you feel right now, don't you? And I was like, yeah, that's it. And he said, you're never going to get to the endgame and win any significant opportunity until you have this feeling, because you're going to get to a point where the organization, especially if it's a complex engagement and there's some elements of risk on both sides, you're going to get to a point where either your group freaks out or their group freaks out. And if you're not getting there, you're probably not getting a deal done or close to getting a deal done. Something else is wrong. And that to me was an epiphany. And I think as you talk about this. That was one of those moments that gave me more confidence to understand that discomfort, or that— I guess, you know, turbulence is probably the right word, given what he was, he was putting together. But that was big for me. That was a big moment.
That is— that healthy paranoia is the difference. Because yes, if you're blissfully waiting for the purchase order, you're not anticipating or planning or putting in contingencies for that.
That's right.
That plane fire.
And that's right.
Always happens.
It does at different levels. Some are, some are more severe than others. Sometimes it's 15 minutes turbulence, and sometimes you're pretty sure you hit the ground, but you're gonna go through that. And that was, that was an awakening for me for sure.
Yeah.
Especially like with a new account, you might get a renewal or an automatic type thing or an easy deal that'll go through without any friction. But a big new customer that involves change and dollars.
That's, that's the word. I, I— you took it out of my mouth. Change. When you're— when you, when you are really injecting organizational change, and it's going to change systemically behavior for people in a company, or potentially mean labor reshifts or reallocations, it's— that's a difference. If you're shifting out a piece of software with a few pieces of functionality that work different here, this whistle's blue, this one's green. You don't have to worry about the planes sometimes. But then you're in a commodity game likely too, right?
Well, well, that's it. And it's not logical. It's emotion. People get, get scared with change, they get— that's what they get, apprehension, they get second-guessing everything. And if you're focused on just ROI and the logical reasons, You're not gonna see it.
Oh, I love that because I always have this argument around that. I believe everything comes back to emotion, even, even after all the practicality, because even that ROI— Brian, it's got to be the ROI. We don't have the ROI. But then there's another question. Who's so concerned about that ROI? Well, if that ROI happens or doesn't happen, who's impacted? How does it impact? Oh, they don't get that job. Oh, okay.
Wait a minute.
It's gonna look bad.
It's always about emotion, always to me in the end. It's really hard to see, but I believe you.
Well, that's it, because I work with reps all the time and it's like, it makes sense, they can afford it, they like it, everything is kind of bought on, but it requires a level of comfort, a level— and, and people like try and stay away from proof of concepts. They say, oh, it's a waste of time or something, but you've got to get that comfort That change of ownership where they're like, yeah, this is going to be good.
Yes.
Not, it could be good.
Yeah.
Well, especially with what's at stake with a lot of these decisions, the it could be good doesn't work.
It doesn't, right? There'll always be, well, why don't we wait another quarter? Or let's see what someone else says. And Janie or Joey thinks it's going to be a friction, it won't work with this or that. All these little red herring objections kind of start popping up at the 11th hour.
They do, yes.
And what's always the safest thing to do? Nothing, right?
Yeah, yeah. I, I love, um, and this is where going back to again, like, I, I think you mentioned at one point with, um, some, some content I saw from you talking about the practice introvert and that, that becomes an extrovert. But I'm, I'm such a huge believer that those are some of the best salespeople in the world because they're the curious ones who ask the questions. And a lot of times, the guy that freaks out a lot of the time I've seen is, and you can teach, don't get me wrong, there's a lot of great pitch salespeople. I love when somebody's got their pitch down. But there's some people who have made their living by putting on the show, the razzle-dazzle, they can pitch, they can talk their way out of everything. But if they get to that point, that's their modus operandi, they just want to do that more. That doesn't help. That's where you need to be the investigator and you need to ask a lot of questions. You need to have a broad and wide net or you'll never know why things are getting quiet. And so I think those are some of my favorite sales reps that I've worked with are the ones who are great with that, you know.
That's the difference between large deals and small deals. The small deals, you want the infomercial, um, Shazam guy, right? Very quickly showing how before, during, and after, and look how beautiful it is. The problem is, in bigger deals, it's not just the product. They believe it works. They like it. Life would be good with it. But we've got to— we've got to run the gauntlet from here to procurement and issuing it. That's not fun.
Nope. It's a lot of work.
Right.
Oh yeah, because you know those purchasing people at the party, they're always the ones up on the table with the lampshades on their head. No, they never go to parties. They're like, you know, how can I ruin the party?
I've, I've had, you know, doing this long enough, I've— this is another one where I've learned not to judge a book by its cover. Um, I have— I know there's, for, for each type of functional role, there tends to be sort of a stereotype. Um, and I do believe that, trust me, there are a lot of— in that profession, there's a lot of professional party ruiners. But I have met some of the best folks that I've gotten to know in those organizations too that have really helped shepherd a win-win— I hate to use it— but deal for both companies as a professional procurement advisor. And I have been dancing on a few tables with some of them. There are some out there, Brian, that believe it or not—
Right.
Invite to the party. And you know that, but I mean, some of my best long-term contacts have now become those people that are now those folks that have helped me through those deals sometimes really kind of put me in a vice over a deal. But in the end, they knew that organization would perform, and then I was a trusted advisor later. But man, that can be a painful part of the process, no doubt.
Right.
And especially if you're kind of either blocked or not introduced or not brought in, because— yeah, because guess who's not good with procurement? Everybody else in the company, right? Because you gotta— if you understand what they need for their audit and how they are graded and reviewed. They, they just really want to make sure it's done properly. They don't want to stop it. They just want it done properly. Properly sounds bureaucratic to anybody outside of purchasing.
Yeah.
Yeah. No, but that, that's perfect. And that gets back to— and we've had this discussion before too— when, when I've had a more junior rep say, what do I do with this person? They're just— I can't handle them. I can't control them. They're this, they're that. I'm like, well, what do you— what did you learn about what makes them successful as it relates to this part of the process with you? So I think that's really, really an important one. And it's— I think it's huge for that part of the organization too, to your point. How do I help you run the most efficient process possible? What do I do for you to make sure that we're ticking off everything that needs to be ticked off? Obviously, I need to make sure that I showcase the value of the solution because it's gonna be really important to you and the business team. But, but can you, when we start our discussion, getting back to that whole thing we talked about at the beginning, building that relationship, can you, what are the, I'm taking some notes here, but what are the 5 things that you really want to see out of me in this process? And do you expect that of all the vendors here? Because I want to make sure I do that for you.
Right.
I mean, that's, it may not win something for you, but you're starting off on the right foot. You're doing some basic blocking.
tackle.
Right, because when they start answering, you dig into it, and then you find out what's the personal win for them.
Exactly.
I was brought in to digitally transform this department, and I've been given 9 months, and I haven't had much success yet. Oh, so you'd like a quick success?
Oh, and your focus is digital transformation, which is also a big part of what we're doing. Maybe I should really talk to you about this.
Yeah.
And how we can help there. That's— I love it. That's it.
Instead of what you do and what's the product do and how is it different than the competition?
Exactly.
Yeah.
Because most of your clients probably go with you not because of the product, because of the trust and the confidence that you've built into solving their problems.
Yeah, exactly, exactly. I like it. And as an attorney once told me in the Netherlands, we're in violent agreement, Brian. Violent agreement.
What was another epiphany that you had along the way that really took your game to the next level?
Oh man, uh, that I should be less afraid to fail. to fail as much as I possibly can, not in ridiculous manners where I'm not trying to achieve something, but don't be afraid to fail. And that's another kind of thing I'm trying to pass down as a dad is we have some perfectionism that runs in my family. I'm no stranger to it at times, but really understanding that you're never going to get great unless you fail that 100 times before you do something great. And I'm a big believer in the Malcolm Gladwell perspective on a lot of things around human behavior, including the 10,000 hours of practice mantra. And whether it's 10,000 hours in a profession or 6,000 or 15,000, there is a magic point where it's— and it's not necessarily a math equation for everybody, but where you get over that hurdle, where you unlock some incredible insight as an athlete, as a salesperson, as a husband, as a wife, as a dad. Like To me, it's that constant effort and you can't get there without failing and taking risks. And so I think if I was going to tell my younger self, do more of something sooner, it probably would have been that. And the other part of that would probably be the other epiphany is I was better than I knew I was or thought I was. And I didn't have that self-confidence early, which I think is true of a lot of people and a lot of salespeople. But again, you don't develop that until you Go through adversity and, and get hammered by an obstacle and figure out how to work your way past the obstacle next time. So those are, those are the things that really come to mind for me.
I think those are good because so much of sales is counterintuitive. And if you follow conventional logic, you only lose, right? Yeah, because you go, it's about the client, not about me, right? I should be questioning, not presenting.
It's so funny because you're right. And conventional logic, I also think about external perceptions of salespeople and how funny it is that, you know, when my friends talk to me, what they think I do versus what I really do. And we're problem solvers, we're essentially problem solvers. I mean, that is, that's what we're here to do, that the person that solves the problem builds the best relationship wins. And so I don't think a lot of people really understand that. I certainly didn't understand that until several years into my sales career. I thought I was just somebody who was supposed to go bother somebody, right? And maybe that's the reason I was afraid to fail more, because I wasn't offering value. I was a pest, or I was somebody who was looking after my goals as opposed to somebody else's. So that was a— that was another psychological tweak that I had to make over time as well.
Good one. Great.
Hey, I appreciate your time today. Where can people go to connect and follow you?
You know, I've been— I spend a great much more of my time focusing on my clients and working for my company than promoting myself. I'm on LinkedIn under Jay Douglas. That's, you know, generally from a business perspective where I am. I'll also say that you see the drum in the background. I've had— whoop, there. I've had a lifelong obsession with music and have made several records with a band called 10 Story Relapse. So that's another thing we didn't touch on, but I think it's really important to have another side of who you are and what you do to focus on, to grow that brain on the other side and get away from the daily thing every once in a while. So yeah, no, I've really appreciated our time together, Brian, and a real pleasure and a real humble thing to be able to talk to you. So thank you so much for having me.
Now, what did you learn from that? When he talked about the analogy of that plane landing, But it's on fire. That is a pretty close analogy to what happens in larger complex sales at the very end of the sales process when we think we have the order. It's this gap between the time we give them a legally binding proposal and the time they— it hits procurement with the final approval. Now, we always think it's in procurement. But it's not. Most of the people who tell me their deals are stuck, they say it's stuck in procurement. Well, I don't believe that. Okay, then, because my next question is, well, who in procurement is working on it? Oh, I don't know. Well, what makes you think it's in procurement? Well, they told me. Is it in the procurement process or in procurement where somebody has the responsibility to issue it? And they can take their time. I get that, that they don't do it fast. Believe me, I know that. But I'm questioning the logistics of where it physically is in the approval process. Some people say, oh, it gets stuck in legal and—
or—
but it's really about getting economic and political commitment, meaning that the person who has The economic sign-off. Now, that is typically not the person who's using it, not the person who asked for the proposal, and probably not even the person or people that you're talking to. Getting to the economic approver. Now, people confuse that with decision. Not which product, not if they need it, Or can they afford it, but who physically approves this. And this typically goes much higher than we would think. And it's where deals get stalled. Now, they typically won't tell you that they're not going to approve it or that, uh, it's dead. No one likes delivering bad news. That's why We don't hear bad news that often. We just hear no news. And no news in sales is bad news. Now, after the interview, I noticed that John had a drum behind him. It was clearly his passion. And I could tell that from his profile. Now, if you use the music analogy to sales, it fits very well because they're both performance How well you play the drum is very different than can you play a drum. And too often we look at sales like, I can play a drum. Everyone can play a drum. You tap your hands on the top. Doesn't mean it's music. Doesn't mean it's enjoyable. Doesn't mean anything. Anybody can do that. In sales, it's much like that. Anybody can take the title, but do you understand how companies buy? Do you understand how to guide them through that process? And we stick too much to the logic of the ROI and all the ingredients, but we forget about the emotion, that change. That change seems to be where a lot of deals get stuck. It makes logical sense, financial sense, Political sense, but people are fearful. And if you ever do a poll on LinkedIn, you will realize how bad people are at making a decision. They can't pick between yes and no. They've got to come up with some other thing to avoid making a decision. Now, how that decision is meaningless, it has no meaning. Nobody knows. Or nobody cares how you voted, including you, but you're unable to commit. Now imagine taking that and adding the company's money to it, their political capital to it, their reputation to it, their quality of life to it, and now you understand why decisions are very difficult to get committed. Getting people interested, Curious, and even having some urgency is good. Getting commitment, getting people to take that final step is the scariest one for them. And we think it should be the easiest because we did all the work, but they may not have seen that. You have to have all these ingredients. And if you're out there playing treasure hunt, Which most people are, I'd say 99%. Because in that example where I drew out the sales process, not one client have I ever met who has had that. Not one. Yes, they all have like proposal, negotiate, close type things in their CRM. But those are stages of decision. And it's helpful. It gives you some idea. But it doesn't really tell you what traps are out there and what you're up against and what's really going on and how to keep it moving instead of stalling. The default is to stall. The plane is always going to be on fire before it lands. The key is how do you keep that fire, uh, in the bathroom instead of in the engine so that that plane can land. There's always going to be something. There's not enough prevention to have it never happen. But what you have to do is make sure the plane does land, it doesn't explode, or it doesn't circle around forever. And that's the default. So if you want to close large deals in a predictable manner or know where you are and what you need to do, And how to prevent those traps, Winning the Complex Sale is the game changer for you. It is a year-long musical instruction. Imagine if you wanted to become good at the drums, what would you do? You go and take some lessons. And then you'd have an instructor, a coach. You would hear other people drum. You would get feedback. What is good drumming? Do you know what good drumming is?
No.
Do you know what type of good drumming— what does it sound like? What are the habits they build? How do they break bad habits and get into good habits? How do they get out of the B-player trap? It's all in Winning the Complex Sale. So if you take your game to another level, it's up to you. No one can do it for you. No one can put it in your head. No one can make you do it, and no one can win those deals for you. But if you want to win them, you got to know how. It's not in a book. No one else teaches it. Most of the people out there that try and help salespeople are really focused on entry level. This is not an entry level course. This is— the concepts are advanced, but everyone faces them in the large complex deal. You can ignore them. Fine, ignore it. Ignorance of laws of nature do not make those laws go away. You have to understand the game you're playing, and a treasure hunt is no way to do it. We'll see you next week. Thanks for listening to the show. Tell everybody about it. We'll see you next time.
Idea and recommendation if you want to take advantage of this.
And it's crazy. This week, this week I'm full of meetings. I was like, what's happening? And like, I— what I did was I baked in like, I just— I'm very generic and people are like, oh, like, like, tell me more about you.
Immediately.
I have like 3, 4 meetings. Like I already had 2 of this. And, and based on the, on the, on the parameters that you suggested for me, like, oh, go after these bigger companies, X amount of employees. So then by the time I'm talking to them, I already know that, okay, they, they typically have budget. I mean, assuming LinkedIn is correct with the employee size, some of it was, was off, but it's like, okay, there's still like a deal I can, I can It still happened. And, um, but yeah, I was like, whoa, this is— I like, I limited to like 30 connections a day. So then that way it's not like, it doesn't go crazy.
'Cause I remember one of the reps— So do about 30 a day.
Um, like I said, like this week, like 4 or 5 meetings and, and, and, and they're good meetings, you know, and it's just conversations. Like I say, it's not about like pitching, but it's about working them up to that point where it's like, okay, Yeah, we do need to advertise.
So after teaching this for quite a while, here's the steps that you should take.
Take the course once, quickly through it. Find both one-on-ones and office hours that speak to the persona that you want to talk with, whether it be the CEO, the CMO, CRO, developer, marketer, whoever it is that you want to talk to. Because we break it down in gory detail. We break down the persona and what they care about. And then try each step. Try it with your friends. Try it with your coworkers and start to see the results. Now, most people will fight me on it. They'll spend the first month, 2 months, uh, trying to make the system fit into their pitchy email and cold calls. And it works a little better. But it works a whole lot better when you apply it because each step and each pause in between each step has been designed over time to be very effective. And then when you start to see the results, all of a sudden people are replying, people are asking you, people are wanting to talk with you, want to understand what you do. It's almost turning cold outbound into warm Inbound. Now, are they in market? No, no, they're not.
But they're a little curious.
And it's up to us. And I show you in the course, how do you build off of that? Instead of us telling everybody how great we are and hoping they can understand why they need us. And instead of them arguing about why they don't need us. Because until you have active pain, Everyone's in denial. Think about going to the doctor. Okay, you kind of know you need an operation, but you're like, can I get a prescription? And the doctor's like—
he has to ease you, or she has to ease you into the process.
Well, let's take an x-ray. Let's see what we're working with here.
Oh, can I— how about just a shot? Can I just get a shot till the next time I come in?
Then he flips the x-ray up on the light and he He points to something and goes, that's what we're dealing with. That doesn't heal on its own. You have to have surgery for that. He has to build up to that. Until we build up that latent pain into active pain and properly diagnose it and get people to think about what happens if they don't have that operation, they're going to avoid it at all costs.
cost.
That's why the cold pitch doesn't work. You're just igniting the denial. You're not igniting interest or curiosity. It's just denial.
So check out the course. Start the conversation.
Get the meeting. It's all at b2brevenue.com. There's an overview video in the show notes, on my YouTube channel, and on my LinkedIn profile. Pretty much everywhere I am, as well as the website b2brevenue.com. Check it out if this is what you need. You know, this student, zero sales experience, but really, you know, just gobbled up this. And the people who gobble it up the fastest and the best are people who try it and get success. It has nothing to do with knowledge. It's like learning how to do a sit-up doesn't give you a 6-pack.
You have to do the sit-ups.
They're not fun at first, but then you get used to them and you start to like appreciating them. And then you start to get the connection between how you look and what you do. And so you start doing the things that make you look better.
This is what we have.
It's not just knowledge. It is applying it. Taking feedback, polishing it up, and applying the system to your clients.
