HOW TO MOVE FROM TRANSACTIONAL TO ENTERPRISE DEALS
18 Mar 2026 · 47 min
Dan Jurgens, a B2B payments sales leader at PaymentWorks, explains how to win enterprise deals: deep qualification, stakeholder mapping, and mutual action plans beat speed and confidence. Hubris kills deals. He built a year-long training program called Winning the Complex Sale to teach salespeople how to move from transactional to high-value sales.
Chapters
What if you were all nice and comfy at a company, you worked your way up, you were well respected, you knew how to sell the service, and then you go to a startup where it's all new? It's not a transactional sale. It's a transformational sale. It's an enterprise, business-to-business, large dollar amount, changing the way they do business. Sound familiar? I think a lot of us are in that space. And you have to learn that. You've got great sales experience, but it's kind of doing something different. Much more of the transactional. You get action. You know if they're going to buy or not immediately. Then you move to the enterprise sale where it's a step-by-step process. It's not just what you say. Too many of us think selling is what you say. That's part of it. But in the enterprise space, in the business-to-business space, it's a small part of it. It's keeping direction, momentum, and control over a deal. And that's not just finding the problem and building it up to get them to have urgency to take action. That's a little piece of it. You've got to know where to take them, how to build up that confidence in the product. And it takes time and there's time gaps between the meetings. Now, this is very different than most— what most of us are taught. We're all taught about asking the questions, have a close, and that's all good. And a lot of people make the mistake of thinking the large complex sale is just a simple sequence of small simple sales. Eh, not really. You got to know where you're going. You got to know where you are. You got to understand what is going to happen next. So we're going to get into this interview. I think this is obviously a great rep, uh, came highly recommended to the show, and I think you'll get a lot out of it. I'll sum it up at the end. And if you're in the courses already, we had a great office hours yesterday. I had done a poll on LinkedIn, and 70% of the people say that their deals die after they give a proposal. So you can either not give a proposal or learn how to do the pricing piece, how to do the administration, the economic, and the political piece, because those deals are dying. And what's weird is I always find people are comfortable wasting their time versus investing their money in themselves. If you're wasting weeks, days, months, sometimes years Playing this game that you think you know how it works.
I see a lot of people who think they know how it works.
Hubris is the number one killer. Overconfidence, uh, exaggerated sense of where you are is the killer of all deals. Let's get into the interview. I'll sum it up at the end.
Here we go. Hey, Dan, thanks for joining us today. As we're getting started, give us a little background on yourself.
Yeah, sure, Brian. Thanks for having me. I'm a fan, so appreciate being on here with you today. Dan Jurgens. I am working currently with a startup, Boston-based, outside of Boston called PaymentWorks. Spent about 15 years in business-to-business payments before that, working with small companies that were acquired by bigger companies that were eventually acquired by Western Union. So all the way up to the the big dog. And then I thought, right when the pandemic started, it would be a good time to change careers. So I joined a startup here, which has been great. It's gone really well and excited in the direction that we're, that we're headed in. But yeah, started as a BDR right out of college, making cold calls, leads up to the sales team. And 6 months later, it was an account executive role and then kind of just moving upmarket, SMEs, mid-market, enterprise today.
What attracted you to sales?
You know, I think, um, it was probably by accident at first, um, coming out of school, um, you know, when you don't always know what you want to do. But, uh, I was— I think, you know, one of the things that I do, and I have 3 little kids and we always go to the bus stop every morning, and it's almost like you can see the kids that are capable of talking to an adult. Hey, Mr. Jurgens, how's it going? How you doing? And I think, you know, that's the way I was raised, you know, growing up is like, hey, you look somebody in the eye, you say hello, you talk to them, and it just kind of naturally gave me an ability to chat with people comfortably. It's not awkward, it's having a conversation, and it was very natural. And I kind of looked for those kids at the bus today. I'm like, yeah, that kid, I think he could do sales someday. And then the other kids, you're like, I think he might be blowing smoke, I might have to watch out for him a little bit. But that's sales too, right? You got to be trustworthy, but not, not, not suspicious, I guess.
And how long did it take you before you felt at home in sales?
Um, you know, I think it's always unnatural to start with, okay, I've never had a job, I've never done anything. And now I'm going to make, you know, 70 calls a day. And so, you know, when you start doing that, I think it's when you begin having some success is when you start feeling comfortable. And it's like, okay, is this a repeatable process for me? And If it is, what's the what's the key kind of elements that that makes it repeatable and and how do I do that? And so yeah, I mean once I was kind of elevated to an account executive, I think there was that self confidence that comes with it and be like okay, I think I can do this and I think it's exciting. And I was always an athlete, you know, from third grade to through college, and so being able to have that kind of competitive element and and let's um. Let's have a win at the end of the day. I don't know after doing this for 16, 17 years if I could be a salaried employee that says, okay, here's your to-do list for the week, go. And, you know, where's the kind of financial and emotional kind of payoff at the end of that?
And what about it motivated you? Was it the income? Was it the challenge? Was it nothing else?
Yeah, no, I mean, I think it's at first you kind of want to prove it to yourself. You know, hey, can I do this? I don't necessarily know what I want for a career. or is this for me? And, you know, my kind of competitive nature said, yeah, I want to give it a shot. And when I did start having success, and then when you get that kind of first commission check, you know, the one that really kind of opens your eyes, you're like, okay, um, yes, this is, this is definitely for me. This is fun. And, um, I want to kind of see where I can go. Um, I've hired a lot of BDRs, managed some BDR teams, but, you know, 16th or 17th year of me carrying a quota. I've always had a quota. And I do really kind of enjoy that. I almost run it like my own little business, I guess. And so that's, I think, rewarding in its own right, just having that autonomy.
And can you interview BDRs today and tell how well they're going to do like you can at the bus stop?
I mean, I think there's a little bit of that. You got to be able to, you know, can they engage with me? Are they going to be memorable? I think that's kind of an important part of, of any conversation. You know, do I remember that? Would I like to really kind of speak with them again? Or was it kind of a forgettable experience? And I don't always know kind of what that it is, you know, you kind of, kind of know it when you talk to somebody and you say, you know, I, I kind of believe that was, that was, that was an authentic person. And when somebody, you know, a lot of the times BDRs today are on the younger side, and I don't know if they should be, um, but, um, it's, uh, it is kind of, you know, do I think this person is going to make good judgment? Are they going to, um, kind of work hard and, you know, have that, uh, that it factor, whatever it is?
Well, because like today we socialize differently, you know, we text versus call. Yep. Right. So it's very asynchronous. And kind of our social skills are valued highly, but we don't develop them the same way, I don't think.
Yeah, no, that's true. And I mean, so much of business development is kind of that, let's do it through LinkedIn, let's do email sequences, let's do— and I think that's valid because that's what the marketing machine should be, right? But when you're able to, hey, let's Yeah, I'd like to learn more, and a BDR is going to initially engage. Is it going to be a message that's easily conveyed, easily understood? And also, is it kind of relationship-based? I know I try to kind of build those relationships. I have, okay, 5 I want to give something to today without asking for something in return. And how often can I do that, you know, deposit into the piggy bank without asking for something? Um, I think everybody kind of hates that, uh, you only hear from somebody when they want something sort of thing. So, um, but yeah, no, I mean, all 3 of them, you know, whether it's email, LinkedIn, um, the old-fashioned cold call, I think they're all— they all have a place. And it's just how, how do we use them appropriately to drive value?
And that core thing hasn't changed because when you're giving, it feels like, when am I going to get something?
Oh, totally, totally.
Instead of, no, the time will come.
Yeah, I know, it's true. And you got to have that patience, I guess, right? You know, especially in an enterprise sale, it's, you got to realize, I guess, we're not on our timeline, you know, we got to really kind of first of all, just make sure we're speaking to the right people and kind of navigating that landscape. I think My team was having a really cool call. You know, we always have these weekly, um, what did you learn, what can we do better, industry update, is there anything anybody wants to share. And, you know, there's normal kind of industry updates, but there's also, you know, people sometimes bring back things we all learned, you know, whether it's like a Sandler tactic or whatever the case may be. And, um, I really appreciate those calls because it kind of reminds you, you know, stay away from the, the Ninas, you know, no influence, no authority, you know, who are you talking to. And then when you find somebody that is the decision maker, you know, start providing value. And whether it's success stories you've had with their peers, whether it's, you know, podcasts, whether it's things that would just be relevant. And what I always try to do is reflect, you know, would this interest me? Is somebody giving me like a paragraph that I have to read or is it like 3 bullet points that I can get through in 60 seconds? I kind of like your, you know, 1-minute videos. Because, you know, we don't have a lot of time getting through 1 minute with something that has kind of a punch at the end that, oh, that makes sense to me. I understand that is way more compelling than paragraphs or, you know, just cold calls that say, hey, you know, I'd like to bring you through my 3 points of value. Do you understand? And it's really difficult to build any rapport, any pipeline doing it that way.
How long did it take you to get this mindset? Because I'm sure—
It took a while, you know, it's not, it's not easy. You know, I started selling to, you know, in my first job, it was a small international payments company. So maybe, you know, 300 employees globally. We had offices, little satellite offices in different towns and major cities. And what we were targeting were importers, exporters. So you're calling like the owner of a liquor distributor and you're speaking directly to the owner and he's trying to get, you know, a better rate on converting his dollars to euros so he can buy more Merlot and things like that. That's a very different conversation and sales cycle than calling the CFO and the COO and the director of procurement and things like that. They're gonna have different priorities, different just ways of communicating with them too. Is it cost-based? Is it value-based? Is it— are we talking automation? Is it kind of big picture or more transactional? And I think I started in a very transactional business where we kind of, here's our platform, give us a try, versus today I'm selling a platform that has an upfront premium. You're going to have to make an investment in this. I want to make sure I'm kind of checking all your priority boxes. Am I— if I'm not meeting your goals and I need to understand what your goals are first, then we can disqualify this. That's okay. I almost think of it as like the quarterbacks that just run right into the middle linebacker time and time again. Like, it's okay to step out of bounds every now and then. Like, Tom Brady's 75 years old. He steps out of bounds and he keeps going and he gives himself more opportunities in the future. But it took a while. I think that's a good question.
Yeah, because now that you're in a much more complex sale, if you take that transactional mindset, it's almost a disaster.
It is, it is. I mean, it's not going to, um, you're not going to get anywhere very fast, and you're not— there's just going to be a lot of nos, right? You're not going to have the relationship that you need to have somebody write a check for $100,000. It's not gonna happen.
It's not gonna happen on a one-call sale.
No, no way. Um, one of the things that I really like is a mutual action plan. It's, um, it's kind of— I mean, I'm sure folks do it in a variety of formats and whether it's a, you know, a sales book or kind of whatever you want to call it, but if you are able to kind of document the meetings you've had and what the outcome was And then have them agree with that. Yes, that was the outcome we want, and here's a pretty good next step. You have kind of a game plan or a path to arriving at the result that your prospect hopefully wants and that you want as well. And it's something we call it mutual because I'm going to be doing my end, I'll update this, but mutually I want to understand that you're on board with this plan and this path and I try to position as this is very non-binding, but it is something that will give us a guide to get through this, because a lot of the times folks don't know how to buy a piece of software, and they don't know who necessarily at their organization needs to also sign off on it. And one of my go-to kind of questions is, you know, have you bought something like this in the past, and kind of who was involved? In that process. And if they're— if they've never done it, then you probably got a Nina or somebody that's not going to be able to get you kind of where you need to go. Um, but it, it really does kind of put some accountability on both sides, and it allows you to disqualify pretty quickly too, because I don't know if there's anything more important than disqualifying it, because then you can spend more time on the qualified.
Right, because it could disqualify for a lot of reasons. They're too small, it's too early. And the mutual action plan, or any kind of action plan, gives you an acid test of how interested they are.
Absolutely.
If they don't do anything, they don't show up for the next call, that's no good.
Yeah, I mean, you're getting close to just— and I try to, you know, you got to be able to, um, have a conversation. When I'm training BDRs, I try to say, you know, explain what we're doing like you'd explain it to your buddy. You know, hey, you got a new job? Or your dad or your mom, you know, hey, did you get a new job? You know, what is it? It's like, well, you know, today PaymentWorks is, you know, we make sure folks always pay the right vendor. They never pay a fraudster. We don't need to get into the technical aspects of how it works and features and things like that. But if you say, you know, there's a lot of fraud, certainly during the pandemic, and our goal is to make sure our customers never pay a fraudster. They always know who their vendors are. It's always validated data and validated information. And naturally, in our line of work, folks are gonna say, well, how do you do that? And if somebody asks you how you do it, then I think you've probably created a little bit of interest in what you do.
Yeah.
And if they start asking questions, I always say that on the BDR call, now you've got them because now they wanna learn more and you can either give them what you're comfortable with Or kind of pivot and say, you know what, these are all amazing questions. Let's set up a couple minutes for you to talk with our product expert, and we'll take it from there and see if it's something we can, uh, learn more about together.
Well, that's it, because if you take the transactional view, you'll go nowhere.
No, you can kind of build that interest up like a foundation. Yeah.
And I, I think, you know, transactional places, I, I learned a lot doing it. and understanding, you know, how to, how to just get people listening to you. But I, the number one thing on our initial call is we're not trying to sell anything here.
Right.
You're trying to see if somebody has goals that align with our solution. And if we can do that, then we can kind of say, okay, you know, we, we do check a lot of those boxes. Is there anything you'd like to learn more about? But the transactional, starting with that and kind of grinding, it kind of makes me appreciate the enterprise sale a little bit more because it is truly relationship-based. And is somebody going to remember me when they're ready to look at this 9 months from now, 12 months from now? If, you know, somebody comes and they want me to kind of change my, my cell phone plan and it's for $10 savings, it's just not worth it to me right now. But when we're ready and My kids get old enough to have cell phones. Now I need to kind of get a new plan. Am I going to remember, you know, the guy that was kind of calling me, or is it fairly forgettable? And that's something that's hard to teach, but it's really important in the enterprise sale. And that's why the value drops, the deposits into the piggy bank, I think, go a long way. And just kind of creating that relationship, because giving without asking is important.
And what were some of the milestones in your learning As a sales rep where the lights went on and your game went to the next level?
I mean, I think when you start to ask for feedback from your managers, you know, sometimes you get into a safe place where, okay, I've hit my quota a couple times, I think I know what I'm doing. And you're not putting yourself out there to learn more. And that's what really kind of changed. Okay, well, Dan, you know, it's great, you kind of hit your goal, you hit this, but I think we can do more here. I think we can go up market. I think you can talk to these folks and this is how you do it. And kind of realizing that and having that self-reflection is really important in terms of getting better. And then also, I guess, taking risks. I mean, one of the biggest risks I took was changing careers right as the pandemic was starting. And it was a safe spot. It was— I didn't go on an interview for 15 years because the companies kept on being acquired. And I started in that sales satellite office with, you know, 10, 15 folks. And the first acquisition, it went down to 7. The second acquisition, it went down to 3. Then it was me as kind of the lone sales rep working remotely. And my boss and I were buddies. We had a great relationship and it was very safe, but there was a ceiling there. And that was kind of a milestone in its own. It's like, okay, am I going to move my family to another city, another location to have that additional career path? Or am I going to kind of take a risk and go from Western Union to a 35-person startup company? And I'm really glad I did it. That's been rewarding and very eye-opening and educational on its own. But I wish looking back that I did take some more risks earlier on. You get into those safe spaces and it feels good and it's— it is where it is. But that's— those are the milestones that I remember, you know, asking to get better, taking— starting to be comfortable enough to take a risk here or there. And, um, and it's really— it's going to make you better at what you do.
Because a lot of people are very sensitive to feedback, and very, very few ask for it and want it.
I was, um, one of the— I was, you know, as I mentioned, I always kind of played sports growing up and, you know, thought I was pretty good. And, you know, high school, you're the big fish in the, the little pond and things like that. And then I Went to college and I realized very quickly I'm not very good at all. So what can I do to get better? And you kind of have to ask feedback, talk to your position coach and say, you know, you know, what can I do? Because is it something— is it it that if a salesperson doesn't have it, that's, that's tough? Is it it when you're an athlete and it's God-given ability and you just, you can't get it? Or are there certain things you can work at? Can you find kind of a niche spot on the field that's going to get you playing time? And that's kind of the feedback that, that if you're willing to do that, and you realize you don't have the answers at viewpoint, you just don't want to kind of hear the negative feedback. I think that's what top performers do pretty well is they're open to it.
And what was it like that first 9 months at a startup going from a, you know, very comfortable situation to a very uncomfortable situation?
Well, enterprise sales, you know, coming from a more transactional, okay, we're gonna give you our platform, and that's not easy on its own, right? Because you're calling into a CFO and saying, hey, you're doing your international payments wrong through your bank. We got the right way to do it sort of thing. That's a difficult conversation, but it is a, I'm gonna give you this platform and I just, you got, I'll prove it to you, give us a shot. And so it is transactional from that standpoint. And then going to the startup where it's the large upfront premium to get the value that you want, that's going to really change your organization. I don't know if I was ready for the length of the sales cycle. You know, I don't think I closed my first one for 9 months or so, which is anxiety-inducing when you're used to the safe place. But once, once you really do get your relationships where they need to be, and that's, that's essentially your pipeline, and you're able to leverage past relationships and start getting referrals, um, it became really exciting. But I, I saw— I made this proactive move where I was aware of this company because I was interested in setting up a partnership at Western Union with them. And I just had so many customers that were falling victim to payments fraud, paying a fraudster posing as one of their vendors. And I didn't see anybody else in the market kind of filling that gap. So I was like, I'm going to do this. I see this as kind of a critical gap in the market. I'm going to take the leap. And the first 9 months were nerve-wracking, but I knew I was in a space that I really wanted to be in. And I think that's important too, because at some point in my career, it's okay, I can do what your bank can do for a better price. And that's not going to continue on. And having a real compelling product where kind of in your heart, you know, like this is something that's going to bring value to a lot of folks. I wholeheartedly believe in this product. It makes it a lot easier to sell and a lot easier to be believable and be kind of trustworthy.
But you're selling to kind of people with not the greatest of personalities, right? CFOs aren't known for being gregarious and Chatterboxes, right?
And you don't— I don't get the CFO in the first meeting, right? It is, um, payable, or— Yeah, I mean, I think it's a lot of, um, you know, VPs of finance, um, sometimes risk officers when we're talking about fraud. It is sometimes procurement because they own the relationship with all their vendors. And that's why, like, I talk to some folks, they're like, you got way too many stakeholders, I wouldn't want to sell what you're selling. But I kind of look at it like we can spread this value over several different departments. We can bring value to AP and finance, to the risk office, to procurement and purchasing. And whether that allows you to kind of split up the spend and the budget, or you're just getting— we're dropping a little bit of value in each of these departments, which is going to make it an easier holistic sell. When you're buying a piece of enterprise software and it's focused on one specific department, But it's going to impact other business processes. It's— other folks are like, well, what do I get from this? And so I think it is a tough sell, which makes it a little bit more lengthy. But when you have a compelling solution that does have value to each stakeholder, you can get champions in maybe surprising places.
Yeah.
It's—
and so being able to get a champion for this account and purchasing, and they're going to drive it for you. But over here, it was really the risk officer. They got burned by fraud. He's gonna drive it for me. You can kind of pivot and turn, okay, this is my guy to quarterback this.
And where does the sale either get stuck or stalled?
I think there's 2 main places. It's maybe after your first meeting and you just didn't do a good enough job uncovering the pain or their goals, or they don't wanna admit they have a problem or are at risk. And so that's, that's kind of on me, right? I need to be able to ask the good questions, you know, are you experiencing this? And I try to do it by storytelling what other folks in their area have experienced. You know, we just set up a huge municipality. They came to us because they sent $1 million to a construction company that was actually a fraudster. You know, do you ever experience that? Are you seeing these attacks? Are you, you know, feeling any of that? Or hey, another large university. We just kind of set them up during COVID They couldn't get their checks out. They just couldn't. They're signing, they're meeting in the parking lot, their signatures on each other's backs. It's horrible. And we were able to give them a platform where they could securely convert those all to electronic payments and not have to worry about the fraud element because they didn't want to convert checks because they were worried about fraud and they just wanted to do paper. Are you experiencing any of that? And the more stories you have that you can tell, I think that is better than, hey, our product does A, B, C, D. And it's really about that kind of that storytelling. And that's something that salespeople need to be able to do well is tell a story that someone can relate to. But yeah, it's that after the first meeting. And then of course, the dreaded proposal meeting, or, hey, this is the price. Are we gonna— are we gonna continue it? And again, you have to do your research and your homework to be able to— I guess it's justify that proposal, right?
And why now?
Right. Where's the urgency? Yeah, because they could—
because I could imagine that first call almost always goes well. Yes, because it's educational.
I've heard that. Yeah, we've had that, we've seen that. It'd be nice to have, but yeah, once, once they see the, the investment, um, how do you bring it back to, let's, let's regroup, let's go back to the mutual action plan. On call 1, you said X, Y, and Z were your goals. This is gonna reach all of your goals. Is, is that a lot more palatable now? Do you agree with that? Are we bringing value to the other departments and cross-functional work that needs to be done? But I think to your question, those are the 2 areas. You got to do a good qualifying first meeting, uncover their goals. And when you're going to be delivering that proposal, be ready to justify it, bring it back to their goals. Otherwise, they're just going to see a number.
Yeah.
And what do you think you do better than most salespeople? Um, it's, I guess it's 3 things. It's first of all, decision-making, you know, is, and there's a lot that goes into decision-making. Is this a qualified prospect or is it dequalified? How am I going to spend my time today? Um, you know, what's my, what's my approach with this prospect who's, who's a little salty or whatever the case may be? And then it's always kind of the it element. Are we able to just kind of have a conversation and am I going to be trustworthy and believable? And then the organizational part of it. I've seen and worked with lots of folks and their sales force is a disaster, right? It's just like, we don't, we don't even have a pipeline. I don't have things coded the right way. We don't know if this guy's qualified, if he's in my pipeline. And so I try to keep a pipeline that's as small as possible. Because once you have a small pipeline, you can address and really start to build the relationships. If it's just Salesforce, you know, Stratus, the Matrix, you're gonna be— you're gonna get lost quick. And sometimes folks are just trying to schedule, hey, I have tasks that I'm going to follow up on today. Well, where does that go? You got to bring it back to a controllable and organized pipeline. I think The mutual action plan is part of that pipeline because that's your tool for each prospect in your pipeline to keep yourself and them accountable throughout the sales cycle. So I think those are probably the 3, the 3 things that I try to improve on, I guess, each day.
Yeah, because I heard focus, judgment. Yeah, what to work on in what order.
Yeah.
And do you think you got that just off of osmosis over the years of Spending time on things that didn't close and not enough time on things that should have closed?
Yeah, no, just years of blowing opportunities, I think, just reflecting, you know, what, what went wrong there. Um, and, you know, and then there was a lot that I had to learn going from a transactional sale to an enterprise sale, and, and I was just open to that, you know, how do we do this? What's, what's gonna make me most successful? And Um, just being open to kind of taking the advice from folks who have done it before. Um, you know, in, in just knowing you don't have all the answers because you don't.
And the it part, do you think that's learnable, or is it like sports where you either don't have the speed, the height, the strength?
Um, I, I think— I, I don't think all of it's learnable. I think there's a little bit of like, hey, you got to be able to, to have this rapport and this relationship and this This ability to converse with anyone. You know, my wife kind of tells me, you know, you could just be friends with anybody, or she tells me, you know, we're at a family event, can you tell that story? I'm like, well, I wasn't even there. She's like, we just tell it better, you know. And so being able to kind of have that, I think, is important. There's a lot you can learn, a lot you can teach. But I've also seen the revolving door of sales reps— 5 months and gone, 4 months and gone. 6 months and gone. And it's also, they interviewed so well and, you know, what was it? It was, they just didn't have it. And you're like, well, what was that?
I don't know.
They just didn't get it. Didn't, weren't able to kind of either they didn't have the work ethic and they just interviewed well. They didn't have the organizational skills, but they interviewed well, or they just weren't able to see eye to eye with kind of what is gonna get an enterprise sale from qualification to decision-making, um, stage, I guess.
Yeah.
And how did you learn that, the enterprise steps? Was it through a manager at the company, or— because it was a— that's very different than transactional.
Yeah, no, I've— the, the, the folks that hired me, um, have been just amazing and very experienced and said, you know, this is, this is what's worked a lot of the times, but you do you. Like, we're going to give you some steps that we think are going to help. But be, you know, be yourself, get through this, you know, be relatable, be memorable, but you need to ensure that, that the organizational process of moving someone through the sales process is followed. Because otherwise, you're going to get— you're going to go off the rails, you're not going to be talking to the right people, you're not going to be getting the decision makers, the stakeholders, identifying goals.
And did you get any resistance getting the role?
No, I didn't. I mean, we were— I was in the process of, as I mentioned, kind of setting up a potential partnership, and it was very kind of organic and serendipitous where it's like, I kind of really like what you guys are doing. It's like, yeah, these have been good meetings. Do you want to work for us? Sort of thing. And it was kind of naturally came into— kind of landed there, which was kind of another sign. Like, I think this is time for me to take a chance, take a step, go out of my comfort zone. So. It, um, it was, it was very cool the way it turned out.
Cool.
Hey, Dan, appreciate your time today.
Where can people go to connect and follow you? Yeah, sure.
Uh, Dan Juergens, um, dan.juergens@paymentworks.com, uh, LinkedIn as well. So, uh, yeah, really appreciate your time, Brian.
Now I hope you enjoyed that. And what I find a lot in winning the complex sale is that we are conditioned to fall into these traps of send me a proposal. And then all of a sudden it goes quiet. And if you really look at your deals, of the ones that you're not closing to no decision or delay, and you kind of think that's still a deal, and it may be, but why get to that point? Why not prevent that? Why not have control over that deal? Know where you're going and know how to get there. You're not going to learn that from 4 failed SDRs. You're not going to learn that from marketing. You're probably not even going to learn that from your manager. Has your manager really understood the complex sale? People always say, well, what book is there? There are none. Because most of the books are written by people who have never sold, who have never been on a sales call. That bullshit book, The Challenger Sale, That was written by 2 people who have never sold, never been on a sales call. They did research, which is what? Thinking? Sending out a survey? And they came up with this causation that is not a— it's a correlation, not the causation. Yes, great salespeople debate. They push back. But that's not why they're great. They're great because they know how deals get done. This is the big misconception in selling today, is that the, the people who have been doing it for a long time can't articulate why they're good. They've got the it factor. They've got a sense. They know where to spend their time. They prioritize their deals properly. But they're not articulating to other people why their deals get done. So you need to understand how companies buy. And the feedback that I've gotten from the course is, boy, my customers do not know how to buy. They know how to pick a product. They don't know how to get it done administratively, economically, and politically. And to do that is a skill. It's a talent. And you need the artifacts to get that done. Or you can sit around and say, ah, lost to no decision. Does that feel better? The money in your bank account feels better. You're wasting your time, and your time you cannot get back for any amount of money. So when you think that your time is worth less than your money, you can always make more money. You can become smarter. More effective and make more money. You can't make more time. So this is your little wake-up call. You can sit around for another year and hope that things get better, that you get better, that your company gets better, your territory gets better, or you can make you better. You are the means of production. You are the X factor. In your life. Make it better. Learn the game that you're playing, the whole game, not the subject email, uh, what's the right cadence. That, that's not going to make you better. That's going to give you more opportunities to go to no decision. Learn how to win your deals and win more of them. And if you're not— if you don't have enough on your plate, Start the conversation. Get the meeting. Yesterday in the office hours, a rep said, my manager's asking me how my calendar is so full with conversations. And then you determine if the conversation is a deal or if it's just a conversation. And that's the magic, because until you have that conversation, you don't know what it is. And I got to tell you, people are not buying, not because they don't have any money, because they don't know how to get it done. Learn how to get it done, and then you can teach your clients how to get it done and finish this year and every year strong instead of hoping that you get that territory next year, or you're just building a territory for someone to come in after you. Put that money in your bank account now. Go to b2brevenue.com. Sign up for Winning the Complex Sale. It's a year-long course. You get all the content that's been produced for the last 4 years. It's already in there. Plus you get office hours, an hour meetup every other Friday per course. You get unlimited one-on-ones, all of which are recorded and put into the course. There's hundreds of hours of them in there. How are you going to learn about this? This is heads-down, case-study-based, real-world sales community and training. It's not like 4 failed SDRs hunting and pecking out there, giving webinars twice a week, trying to tell other people how to take orders. If they were good at it, they'd be doing it. I am good at it. And I spent my life doing it. Not, you know, teeny little tiny little deals, million-dollar, 7-figure deals that put money in your bank that change your life. Sign up today, b2brevenue.com. We'll see you next time. Make sure you're checking out the other podcasts, Sales Questions, Brutally Honest Answers, The Sales Leadership Show, and B2B Revenue Leadership. You can also check out all the videos are on YouTube. So just search for me there. We'll see you next time. Here's some excerpts from a one-on-one that I did with one of the students in Start the Conversation, Get the Meeting course. Now, this person really embraced the course after a while. It took a couple of one-on-ones for him to try each step. He kind of fought it, tried to make it work within his current model. And that, that really didn't have this type of success. And then after he started, he started to get meetings. He started to get conversations. He started to get all the things that I was telling him about. And he started to get excited about it. He started to see the results that I tell you about, where his week was full of meetings. Now, I'll let you hear this out. I deleted out kind of the specifics of the steps and the tools and the approach, but they're all in the course. If you're already in it, please listen to the full one-on-ones. When you hear the success that people are having, it's not just the steps. It's the matching of the steps with the appropriate Actions and pacing. And then you get people asking to talk with you, which is the goal, which is the fun. So let's listen to it and I'll sum it up at the end and give you kind of an 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 very generic and people are like, oh, like, like, tell me more about you. Like immediately I have like 3 or 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, it was off, but it's like, okay, there's still like a deal. It can, it can still happen. 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. Like I said, like this week, like 4 or 5 meetings, 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 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 points to something. He 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. 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.
