Digital-First Leadership
Digital-First Leadership
EP 49- From Risky Bets To Certain Outcomes In Software Buying
Career bets shouldn’t hinge on hopeful demos. We sit down with enterprise sales veteran Leon Treffler to examine why the traditional software deal stacks the deck in favor of the seller, leaving buyers to absorb the delivery risk, the politics, and the career fallout. From RFP theater to pocket vetoes, Leon breaks down the quiet mechanics that turn a straightforward purchase into a political campaign—and why so many projects slip, overrun, or stall completely.
We dig into the missing half of the “win-win”: how the seller gets a commission while the buying committee gets only their regular paycheck, plus the reputational risk of a failed implementation. Leon argues for flipping the script with a blueprint-first model that delivers certainty of outcome and ties the statement of work directly to that blueprint, creating certainty of cost and higher odds of success. We talk about how AI can model processes, validate requirements, and expose risks before contract signature, giving stakeholders real evidence rather than slideware and giving champions the artifacts they need to overcome skepticism.
Along the way, we map the frozen middle and the internal competitor—those quiet forces that slow change to protect territory. Leon shares practical ways to read the political base behind the org chart, build coalitions, and give buyers a visible stage to claim their win through measurable results and public case stories. The payoff is more than a smoother implementation; it’s a fair value exchange where buyers gain career momentum and organizations gain reliable outcomes.
If you care about enterprise software that actually lands value, this conversation offers a clearer path: replace promises with proof and turn risky bets into predictable wins. If the ideas resonate, follow the show, share with a colleague who signs big checks, and leave a quick review to tell us what shifted your thinking.
Welcome to the show. I'm your host, Richard Bliss. You're listening to Digital First Leadership. And my guest today is Leon Treffler. Leon and I have known each other for a couple of years. And I got to tell you, from the moment I met him and the conversations we've had, I've continued to learn on a regular, ongoing basis. And I thought, what a what an opportunity to have him on the show. Leon, thanks for joining me.
SPEAKER_00:My pleasure, Richie. Great to be here.
SPEAKER_01:Now, we're going to jump right into this because you have been selling or decades selling enterprise software. And uh I know that you've started a book. I've had the privilege of seeing some of that. But what's interesting is that you start the book, you basically are taking the side of the buyer, the empathy for the buyer. And I found that an unusual place to begin with a book. Why, why start there? Why with the empathy with the buyer?
SPEAKER_00:You know, so Richard, I'm going to take you right to the beginning. I have uh always been fascinated by money, um, largely because it's man-made. I mean, God didn't make money, man-made money. So I've always figured out, geez, if I could understand like the man-made rules around this man-made thing, then maybe I could figure out how to make more of it. And so I've always been fascinated by money and by commerce. And one of the things about, you know, that I just couldn't help but notice is that the the the way enterprise commerce exists and enterprise software sales is like bizarre. Certainly as compared to the way you think of commerce traditionally in almost everything else we do. So let's let's let's go back to like ancient times, like in the marketplace when we used to like barter with one another. I might, I might give you a few eggs, and in exchange, you might give me some milk. And there was a fair value exchange. There was like a win-win between buyer and seller. And as the marketplace evolved through the years, and maybe you uh in exchange for eggs, you took little pieces of silver or gold, and maybe little pieces of paper or pieces of plastic. And today you wouldn't even take anything physical at all, because that I'd give you, you know, a mobile payment. But there's still this fair value exchange between buyer and seller. Okay, let's let's extrapolate that to enterprise software sales. Well in the traditional marketplace, you know, the the the buyer is actually using their money, and they're actually going to use what it is they're buying. But that's not true in enterprise software sales. Buyers aren't using their money, they're using the company's money. And what's more, they're usually buying on behalf of their users, right? They're not usually going to be the users of the software they're buying. So you got this like buying committee that's got this level of extrapolation, and it's a little bit bizarre. But uh, when you actually look at the transaction, okay, where is the win-win? Remember in the marketplace, even when we were bartering eggs for milk, there was this win-win. Where is the win-win in enterprise software sales? The seller gets their win. I mean, the seller gets a giant commission check. Sure, yep. But the buyer gets their regular paycheck. And when we go live, all right, well, not one nickel of increased revenue or increased savings makes its way into the buying committee's wallets. So where's their win?
SPEAKER_01:And so what you're saying is the the buyer's not getting paid for doing a good job on closing an enterprise level sale. I mean, they're getting paid, but they're not getting is rewarded the right word.
SPEAKER_00:Well, uh it isn't clear how they get rewarded. I mean, so let's let's put ourselves in the buyer's shoes. What if you're on a buying committee, what is it you're looking for? Well, if you're working for a giant corporation, maybe you you have career aspirations. And that and the way you grow your career, honestly, it isn't by proving somebody else's idea right. The way you grow your career is by being associated with some new idea that others in the organization perceive as having added value to the company. You you get your promotion, you get your you know uh you know, bonus by being perceived as a good steward of the company's resources. So you end up getting your win by being associated with a project that's successful, okay, that you then enables you to tell a story to others around how you did a good job.
SPEAKER_01:And and I got to believe then that that also is involved with that win is avoiding mistakes, avoiding looking stupid, right? So there's that avoidance, there's not just that uh draw, that carrot, but there's that risk is like, look, if I make a bad decision here, it might sidetrack my whole career, right?
SPEAKER_00:I mean, I mean, come on, what is an RFP, okay, if not a prop to show to others that you did appropriate diligence, okay, to be able to come to a solution. But at the end of the day, Richard, okay, um, you're making a career-defining decision because if you're associated with a failed project, your career isn't going anywhere. If you're associated with a successful project, well, maybe you'll get a promotion. But let's trust the risks involved in making that career-defining decision. First of all, okay, maybe you did an RFI, maybe you got a POC or a few custom demos from a software vendor, but you're you're placing a career-defining bet, okay, that the features that you saw from that demo actually work as advertised. Yeah, okay. That's that that that's a bit of a so what you're saying.
SPEAKER_01:There is that your career is being based on the whether or not you can believe the sales rep is telling the truth.
SPEAKER_00:Well, one, okay. One, you're you're you're making a career-defining bet, okay, that you could trust the promise of a software rank. Secondly, okay, once you make that career-defining bet, you have to make a career-defining bet around your delivery partner. And Richard, the thing is that 70% of all IT projects go sideways in one way, shape, or form, or another. 20% never go live. Okay. And the other 50% are either late, over budget, or go live with less functionality that's promised. So, what is the win-win between buyer and seller? The seller gets their win, their big commission check. But the buyer, how do they get their win? One, they're taking a career-defining bet that is only a 30% likelihood of being good for them. So that's the observation that I made, Richard, is that yeah, I have incredible empathy for buyers. Okay. It's a little bit one-sided in the selfish favor. I can understand win.
SPEAKER_01:You know, uh early in the career in my career, in the internet days, um, I had an interesting experience. I was approached by uh uh Oster uh uh the Blender company, right? Um and they came to me because Sunbeam Oyster, that's who it was, and they wanted to register their domain name. Now, this is back before Network Solutions, so this is a long time ago. And so I did a quick lookup and I saw that Sunbeam.com was registered to a rental company in Vancouver, British Columbia. So I told the guy, I said, look, you can reach out and talk to him. He came back the next day and said, Hey, I want to register Oyster.com because it's Sunbeam Oyster. Now that's a rather rare name. All of a sudden it pops up rental company out of British Columbia. And uh the Sunbeam Oster guy's like, so what does that mean? I said, Some guys can't put on your domain names. So here's what he did, and this comes back to exactly what's in it for me. He goes to his boss at Sunbeam Oaster and says, Look, I'm gonna go negotiate with this guy to buy the domain names. How much money can I spend? The his manager says, Don't go over 15k. All right. So he goes and negotiates the acquisition, comes back and tells his boss, and this goes straight with your stand, Leon, can I keep the difference between what the guy paid and what you were willing to pay? Why? Because the guy was smart to register the domain names and then was an idiot because he settled for a pie maker and a blender in exchange for the domain names that were they were willing at the time to fork over 15K. But your point is that that rep, that individual, got no benefit from saving the company$15,000 simply because he was able to negotiate. Now, I know that's a weak example, but it just comes to mind about how out of whack you're right that you're describing that.
SPEAKER_00:It really is. I mean, it really you got to take a look at where the win win. And I think that that what that taught me was that it's incumbent upon us to do everything we can to ensure that our buyers have, you know, a certainty of outcome. And if if we can give them a certainty of outcome based upon a certainty of, you know, building a blueprint and knowing that that's what your application is going to be. And then if the SOW is based upon that blueprint, you have a certainty of cost. So if you have a certainty of outcome, you have a certainty of cost, you have a certainty of success. And then I believe it's incumbent upon us to give our our buyers, our uh the people who took that career-defining bet with us and give them a stage to tell their story so that they truly get their win-win. You know, it may not be in real time, like the seller still is going to get their win first before the buyer gets theirs. But I think we've got to make sure that our buyers get their win for us to really change the way that we can engage with them.
SPEAKER_01:Now, something you mentioned in your book, uh, as I was reading it, that I found fascinating, because as we're talking here about the buyer, very seldom is a single individual, right? We you referred to it as the frozen middle when it comes to buying enterprise software.
SPEAKER_00:Well, I think very times in organizations you have people who have an agenda that may not necessarily be to grow their career. I mean, they're trying to preserve their career, they're trying to avoid getting fired or part of the next layoff. It's like, I just want to go in line to get a lot. That's who I refer to as the frozen middle. It's it's the change agents within an organization that are going to be the ones that are going to be willing to embrace, you know, thinking differently about how the organization is going to have to re-engage with itself in terms of, let's face it, the agentic enterprises of the future. So I do believe that there's finally a compelling impetus to change that may compel the frozen mill to uh to eventually act. But they're going to be the detractors and likely the ones that are going to want to be the ones that say, yeah, you know, why do we have to change? Or why isn't this good enough? Um you know, I think the I think the opportunity to engage with thought leaders within our buyers, especially given that we can provide them with a certainty of outcome, has has been unprecedented.
SPEAKER_01:Yeah, and I'm gonna think that that's that's where that starts to come from, is that the ability for them to be more confident in their decision making, if they right? Normally we turn to we turn to advice, right? We we're gonna ask somebody who's used it before. We're gonna look for reviews. And now, as you just kind of alluded to it, we're gonna turn to our AI and say, what do you think, right? Is this is this a a good bet?
SPEAKER_00:You know, those individuals remember that what I'm also talking about is that, you know, uh the the way that the enterprise software sales uh uh became a little bit distorted was on purpose. Remember, the script for how enterprise software sales is done, the the profession of enterprise software sales was invented by IBM. And so they actually wrote this script purposefully such that, you know, one, they could talk about making sure we put the buyer first, but really it put in it put IBM's revenues first in terms of, you know, based upon successfully selling you their hardware, you were going to be predisposed to buy their software, then predisposed to buy their services. So the way that this process was designed to be, you know, a win for the seller and hopefully an eventual win for the buyer, uh, this was a script written purposefully to optimize the revenues of the vendors. Now, I believe that with Blueprint and the ability to deliver a certainty of outcome, we can actually rewrite the script for how enterprise software sales can be bought.
SPEAKER_01:And just as a piece of clarification for the listening audience, uh Pega Systems, who you work for and have worked with for near most of your career, is a uh is an AI company and has developed a tool called Blueprint that helps these enterprise buyers determine a predictable committed outcome rather than a guess or a promise or a uh, as you called it, a POC, a proof of concept. And so this gives you an opportunity for them to prove that. Now, before we go that space, I wanted to come back and address what I refer to as the pocket veto people. And that comes back to your frozen middle. Those individuals who have the ability to pull out of their pocket a veto and say no, no matter, right? It's just I see organizations and I've been in these organizations that it's the democratic way. Everybody has a voice. But sometimes you don't want everybody to have a voice. I I that sounds did that come out wrong? I think that came out wrong.
SPEAKER_00:No, it it's it's an understanding that in every opportunity you have an internal competitor. Um for everyone who wants to do something, there is some contingency within the organization, okay, who won't benefit from that. And as a result, we'll attempt to resist it. So you have the frozen middle out there who either explicitly or um uh uh you know, honestly, through through uh subdivision, okay, sure to try to come up with fear, uncertainty, and doubt as to why what it is you want to do should be done. And if we overlook that internal competitor, we're overlooking something that is really prevalent in every right. Everyone.
SPEAKER_01:You and I have been around long enough to see it happen over and over again, and almost to be able to identify that individual when you walk in the room, you're like, oh, that's the one I'm gonna have problems with right there.
SPEAKER_00:Let me let me give you to it a little conceptually that in the organizations we sell to, you have people who are aspiring to climb the corporate ladder, and it gets very steep at the top. And when one individual sees someone who they think they are competing against for the next run, propose an idea, it isn't uncommon for that individual who thinks they may be left to try to undermine the idea. It's office politics.
SPEAKER_01:Yeah, it's office politics.
SPEAKER_00:Every organization. And so it it's something that um, you know, I I used to uh read a lot of uh the works of Jim Holden and his books Power Base Selling and The Selling Fox. And he really spoke a lot about understanding the the political landscape of an org chart as opposed to the explicit power base. And oftentimes it's the political base that prevails over the explicit power base.
SPEAKER_01:And we might have to have another conversation about that topic. What's been nice about this one is that you've identified from what I'm what I'm hearing and what I've read in the conversations, that the buyer, traditionally in enterprise, has been at a disadvantage because their careers are being based on the promises or the uncertain outcomes of a complex deliverable that's spending high-profile, high-cost execution. And you have really taken this to start focusing part of the Pegasus solution, and we can have another call talk about that later on as we wrap up here, but that is to remove that uncertainty. So removing the uncertainty, it might even have an advantage on that political side that we can't really do much about at this point. But that that that predictable outcome rather than a pro um rather than a promise, you can show it, you can prove it, they can execute it on it, and suddenly that enterprise sale becomes a win-win for both of them. Is that what we're looking at?
SPEAKER_00:It is, it is. If we can go from this paradigm where the buyer is making a career-defining bet where they're only likely to succeed 30% of the time, and change that to where that bet has a certainty of outcome closer to 100% likelihood of success, then I think we can change the way the world buys software.
SPEAKER_01:I like that. Leon, thank you very much for joining me today. And I'm looking forward for the opportunity maybe for us to do this again, talk about some of these other topics we touched on.
SPEAKER_00:Absolutely my pleasure, Richard. I look forward to it as well.
SPEAKER_01:You've been listening to Digital First Leadership. My guest has been my guest has been Leon Treffler. Leon's with Pega Systems, and we've been talking about basically the buyer's opportunity when it comes to buying enterprise software and how Leon has addressed that. Uh fascinating. I'm looking forward to his book coming out. Thanks for listening. Take care.