
AI and sales—history repeating itself. Todd argues that more buyer information has never reduced the need for salespeople; it has increased the need for service, trusted advice, and buyer-centric execution. He also critiques how AI is being used to scale/automate “being human,” and how sales forecasting and pipeline incentives often become seller-centric and inaccurate.
Todd Caponi is a sales leader and author (four sales books, including negotiation and transparency). He’s held VP of Sales and CRO roles. He’s also a “sales historian” who built a collection of 300+ old sales books dating to the 1880s and brought early telephone prospecting texts (e.g., 1910s/1911 scripts; “Successful Telephone Selling” from ~1960; Salesmanship Theory and Practice by Thomas Herbert Russell).
AI won’t replace sales; it risks repeating past tech misuse (phone/email scaling “for evil,” leading to regulation). “Personalization at scale” and AI SDRs/AI “personality” are often rejected because they feel inauthentic. Forecasting fails when stages measure seller activity instead of buyer behavior (e.g., next-step calendar willingness).
1910 “buyers no more nowadays” predictions; Sears mail-order catalogs; 1918–1922 turnover “purges” mirroring 2022–2023 downturn patterns; buyer engagement evidenced by willingness to schedule next steps; “4X pipeline” incentives creating fake pipeline; forecasting improved by layering buyer behavior (“why change/why you”) over sales stages.
Written by AI. May contain mistakes.
Engage in light discussion about food and shared experiences before getting into serious topics.
“It would really help us get in front of more sales leaders exactly like yourself.”
Explore the history of cold calling and sales strategies from the early 1900s.
“We were talking about pasta and food and all of this kind of good stuff.”
Discover Todd's unexpected path to becoming a sales historian and his collection of vintage sales books.
“I was actually just joking with my wife about, uh, in high school history class, I was a moron.”
Discuss how historical trends in sales and the economy can inform current practices and strategies.
“And now, you know, here we are six, seven years later, I've got over 300 books in my collection dating as early as the 1880s.”
Delve into the implications of AI in sales and the misconception that it will replace salespeople.
“Anytime we're delivering to a new group, the story I tell is around how the American economy at least experienced an all time, you know, high from a bull market from 2009 to 2020.”
Exploration of how AI is perceived in sales and its impact on salespeople's roles.
“Which I don't know what you're seeing with your clients, but I have seen a lot of companies attempt to replace the inbound function of their organization with AI.”
Reflecting on historical technological advancements in sales and their impact.
“and like all of this other kind of stuff, what are you seeing?”
Discussing how salespeople can thrive despite the abundance of information available to buyers.
“That we get this incredible technology, and hey, let's use it to get more out of salespeople.”
How AI should enhance rather than replace human interactions in sales.
“When we do that, customers not only want to connect with us, but they buy faster, they spend more, and they advocate for you.”
Evaluating AI's potential for coaching sales reps and its current limitations.
“They get 0.0001 % to go, yes, get me some, that it works.”
A discussion about the current state of AI in sales and its applications.
“And he was being kind of a wise-ass in it.”
Exploring the integration of AI in sales training and the challenges faced.
“and then add in layered customer context too, for the client that we're working with.”
Linking historical sales practices with modern AI applications in sales forecasting.
“Like what trends are you seeing and what are your thoughts on centralizing some of that stuff?”
Discussing the importance of understanding buyer behavior in sales forecasting.
“Let's talk about some of the other areas that you like to talk about that are like these age old topics that we got right a very long time ago and like kind of forgot some of these lessons.”
A strategy for improving sales forecasts by incorporating buyer behavior.
“And AIDA sounds so dated, but he actually got that right.”
Analyzing the quality of sales pipelines and the metrics that drive sales success.
“I think we're buyer centric in name only.”
Learn about the drawbacks of the 4X pipeline philosophy and its impact on sales.
“But step two is a mistake that I always made.”
Understand the importance of pipeline quality and celebrating losses to improve sales outcomes.
“Wouldn't it be great if we could get to 2X and get to 150 % of our number?”
Discover how to create a culture that learns from losses and improves forecasting accuracy.
“But we are measuring the wrong things when we are focused on pipeline load instead of pipeline quality.”
Explore the issues with commitment in sales and how it affects forecasting accuracy.
“and what a good deal does not look like.”
Learn about historical approaches to quota setting and their relevance today.
“That when we force reps to commit publicly to a number or commit specifically to deals, we are incentivizing them to lie.”
Learn about the difference between quotas and goals in sales organizations and the impact on performance.
“The last piece on that is in many cases there was quota and there was goal, two different things.”
Understand how to optimize sales training and enablement for better learning and behavior change.
“Uh, I got some surprise rapid fire questions for you.”
Discover the five key responsibilities that revenue leaders should focus on for success.
“Last question is, knowing what you know now, what advice would you give yourself as a first time, let's say, revenue leader?”
Learn how to effectively assess your team's performance and future potential.
“You now have a 30, 60, 90-day plan in your back pocket where you can go through and go, how are we doing on each one?”
Explore Todd's podcast on the fascinating history of sales.
“I don't monetize it, but the sales history podcast is in season six right now and it's just me.”

Get the gist, explore an idea or ask about something said.
On Outbound Squad, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00You know, there's an old Gartner stat that just gets thrown around a lot. And it's something along the lines of, you know, three quarters of buyers preferring a rep free buying experience. And, you know, when you hear a stat like that in the sales profession, it kind of makes you just like cringe a little bit on the inside and just think, you know, what the heck, man, like, people don't want to talk to us. People don't need us with all of this AI stuff. Like, are we going to be replaced? And what we're going to talk about with today's guest is really that, you know, AI is sure, it's a lot different than a lot of the technology that has come our way.
0:39But we went through something very big about 25 years ago with the Internet. Right. And there was this whole thing that, hey, the Internet is going to bring about all of this information. And buyers are going to know more and they're going to need us less. and turns out that our guest today is a true sales historian. I mean, he's got sales books that are literally over a hundred years old in his personal library. And he brought some of them to the interview that we did, which was super cool. But they were literally talking about this over a hundred years ago when people were printing out catalogs and magazines and all of this kind of stuff and talking about how it's going to replace the need for a sales rep.
1:17Well, the sales profession has really just grown astronomically since then. It's a profession that continues to grow and we continue to be needed. In a lot of this episode, what we're going to talk about is really how history is repeating itself. Just because a buyer knows more doesn't mean that they need salespeople less, right? There are still things that when you think about the very bottom layer, if we use sales as an example, the bottom layer of information sits at the rep level. It's if it's outbound, it's the cold email templates, talk tracks, how to create an outbound process at the very top level would be what a CRO does when they are planning next year.
1:59And they're thinking about what the headcount is going to be, what their capacity needs are, what territory planning is going to look like, how to budget for technology, all of that stuff. That's not stuff that you can find on chat GPT perplexity or, you know, whatever AI solution that you're using, all of the stuff at the bottom, those rep tactics, that's, that's completely commoditized. So a lot of like what AI is providing, like, is it useful information? Yes, but the really strategic sales, the stuff that really transforms an organization, like you're bringing insight as a sales rep and really as a team in those team selling situations that the, the prospective buyer cannot get anywhere else.
2:40So I'm really excited to dig into that with you today. If you're coming across the podcast for the first time, my name is Jason. I'm CEO at Outbound Squad. We're all about helping you turn complete strangers into paying customers. The only thing that we do is pipe gym. So if you're leading SDR teams that are doing the cold outreach thing and you're wanting them to be more strategic, maybe you're moving up market to be more enterprise. Maybe you want to improve some of their call skills, their soft skills around how they do outbound. You're definitely in the right place. AE self-sourcing is something we're really big and focused on right now.
3:13So if you're trying to really transform your culture to be more of a hunting culture, you're trying to get AEs to self-source more because their pipeline tends to be stronger. The deal sizes tend to be bigger. The win rates tend to be higher when they do so. We've helped a ton of companies like Shopify, Zoom, Rippling Gong, and startups building out their first sales teams and everywhere in between with that exact challenge. So if that's something that's top of mind for you as a sales leader, sales development leader, or enablement leader, you're definitely in the right place. So today's episode is with my man, Todd Capone.
3:45What I really like about Todd, I mean, there are many things that I like about Todd. One, he's got four sales books out now. So he's got one in negotiation, transparency. I think it might be three actually, transparency sales, transparency sales leader. He's got a lot of great books. One of the things that I have used religiously as his four levers of negotiating. The dude has been in a VP of sales and CRO seat. So he's walked the walk and he's just one of the best facilitators in the game. He also happens to be quite the sales historian. This is something that he does for fun. He's got dozens of old sales bucks and we're going to talk about where the profession went wrong.
4:26We're going to talk about what history got right. So this forecasting quota setting, being more service oriented, this is all stuff they've been talking about for over a hundred years in sales. We're going to talk about the history and evolution of cold calling. We're going to talk about flipping the script on AI and what's old is new and how history is repeating itself and just a bunch of other really great things in this episode. I think you're really going to enjoy it. Before you hit that, if you've been a listener of the show for a while, what would really help the share grow and what I would really appreciate is leaving an honest reading or review on Apple Podcasts, Spotify, iHeartMedia, wherever you're listening to the podcast right now.
5:05It would really help us get in front of more sales leaders exactly like yourself. Would appreciate that. Without further ado, let's get to the interview.
5:21Dude, it's good to see in person, man. We were talking about pasta and food and all of this kind of good stuff. And I've, I'm really glad I ate breakfast right before this. Exactly. Exactly. We were talking a little bit about airports and travel and debating what the good ones are. So, yeah, I think O 'Hare's not as bad as people think. So, yeah, yeah. I'm, I'm super excited to be here in person with you and I'm even more excited. I mean, can we just show the people the bookshelf here that you brought with you? Yeah, I brought some of the nerdy books. So, yeah, we're, we're as old as 1910 here.
5:56Oh, God. So this one, Salesmanship Theory and Practice, Thomas Herbert Russell. And then the oldest I could find, because I know we're going to talk a little bit about telephone prospecting. Yeah. This one's from the, I think this print is 1960, but it's successful telephone selling. Wow. Because telephone selling did not really become super pervasive until the 1950s. So there's some really interesting stuff. People were cold calling in the 1950s, huh? People were cold calling in the 1910s. What? But it was – Wow. We can talk about a couple of those stories. The first B2C cold calling script I've been able to find is 1911, 1912.
6:35Oh, my goodness. But then B2B is more like 1914. Wow. But, yeah. I mean, back when almost nobody had phones, but they were already cold calling. It's like 100 % pickup radio, but, too. It was not bad. It was not bad. And for the most part, people weren't that upset about it. Yeah. So it didn't take long for us to screw that up. Yeah. No kidding. I mean, that's what we always tend to do in the sales profession. Yeah. Marketers are guilty of it too. Um, the history stuff, I'm curious before we dig in, if you could just give a little bit of background on like your experience, the time that you've spent as a sales leader, especially, and where did this curiosity around the history of the profession, where did that come from for you, man.
7:17Yeah. I was actually just joking with my wife about, uh, in high school history class, I was a moron. Like literally my high school teacher, I was so stupid at history. I, I think I answered a question. He came up and he smacked me on the side of the head, both sides at once. Um, and like, I, people still talk about like, Hey, remember when Mr. Zygmunt smacked you for being a history idiot. So I don't know how that came about. I think at its core when COVID hit and nobody wanted to talk to me or maybe you too. And so I was sitting around, I had an old sales book from 1954. It was from a guy named Percy H.
8:00Whiting, who was a disciple of Carnegie. And he had written a book called The Five Great Rules of Selling. And I had it on my shelf for some reason. And I was sitting around reading it and I was like, this is fascinating partially because 85 % of it is exactly what we should be thinking about selling today. So 1954, 15 % of it is so bizarre that it's hilarious. And so I was loving it. But then as I got done, the book kept referencing older sales books. And I was like, all right, I'm going to keep going. And so I ended up on eBay, on abebooks.com. I ended up establishing a relationship with somebody at the Library of Congress, finding virtual, like, digitalized versions of books and started building out my collection.
8:48And now, you know, here we are six, seven years later, I've got over 300 books in my collection dating as early as the 1880s. I've got old restored phones, got a fully restored phone cathedral style from 1908. That would have been something you'd find at like a corner pharmacist type. Is that what you used to meet with your clients now? That would be awesome, wouldn't it? I mean, it's got the original wiring, but there's no dial and there's no switchboard. So I don't think I could, but it would be really cool to knock it into my line. But, you know, old albums, just tons and tons of stuff. And you can see from these books that I've tabbed up.
9:32I've read all of them. Yeah. And right now I've got about 10 that I've got to catch up on. Yeah. But I just find it fascinating. There's things that history got right, we get wrong. There's things that history did that you would be shocked that they thought that this was a good idea. Yeah. Well, the thing that you've always been my go-to person for a couple things. Like one, I was consuming so much of your content around COVID when that happened because you were talking about all of the things that happen to a buyer, the psychology and what changes. And I remember the Costco analogy I think that you made just around how people are going to become very risk averse and like how they think about stuff.
10:16And then the other obvious one is negotiation and like all of that kind of stuff. You know, great book that just came out on that. the pattern recognition piece of this, where does that come from for you? Well, I mean, it came from just reading the books, right? So that ignited even more curiosity, reading the books. Oh, absolutely. So it's funny. So February of 2022, I started ringing the bells that, hey, listen, all this goodness that's going on, there's a train coming. And I remember posting about it. It was all through a historical lens going, hey, I'm no economist. I'm not that smart. But history is repeating itself exactly from the late 1910s, early 1920s.
11:04And so I posted about it, and I was literally getting DMs from people going, no, no, Todd, this is different. You're wrong. Here's why it's different. There's so much dry powder and private equity like this isn't going to happen. And then sure enough, what was 2022 into 2023? A recession, right? And the idea that we repeat history over and over and over again, certainly we don't repeat it exactly. But you can see what happens in these trends. And so that's what I found so fascinating. Now, just a little bow on that. Looking at the 1910s, 1920s, just to give you a quick, 1914 to 1918 was slow and steady growth.
11:46Looked just like 2016 to 2020. Yeah. All right. And then 1918, we had World War I shut down the economy completely. And we also had this thing called the Spanish flu. Yeah. Economy shuts down for a short period of time. And then they turn the switches back on and we go into boom time. Yep. And so, you know, 1918, end of it, 1919 looked exactly like 2021. It was like perfect match. and then all of a sudden you had an inflation spike in 1919 looked just like uh late 2021 in early 2022 and i was like oh yeah because you know what happened next there was something called the forgotten depression of the 1920s yeah and uh literally sales organizations were being purged 77 salesperson turnover in 1921 85 turnover in 1922 and that was all involuntary So companies purging sandstones.
12:45And I was like, could this be happening again? And sure enough, we went into this valley. And then we came out of it. And then for the next few years, it was up, down, up, down, up, down, which we seem to be experiencing now. Yeah. Now, the bow on it is what happened in 1929, the Great Depression. Yeah. Let's hope we don't repeat history again. Like, I don't see it happening, but you never know. Yeah, this is something that I refer to a lot in sort of the opening. Anytime we're delivering to a new group, the story I tell is around how the American economy at least experienced an all time, you know, high from a bull market from 2009 to 2020.
13:26We had the little blip with COVID then through 2022. And now it's people are taking all the stats would show this people take longer to buy, they want to buy less. There are more people involved in the decision making process, like all of these kinds of things that makes our job really hard. And to your point in 2022, I remember two of my biggest clients announced layoffs literally in the same week. Same week, there was another stat, I think 33 or 37 % of teams got rid of their SDR function. So we're in this time right now of efficiency mode. It is no longer grow at all costs. So what are some of the things that, let's just start with the AI thing because I think it's so relevant.
14:05So you use this term flipping the script on AI, which I love because I think the narrative around AI, if you consume LinkedIn content or any kind of sales content is, you know, there's one narrative that this is going to replace salespeople. Which I don't know what you're seeing with your clients, but I have seen a lot of companies attempt to replace the inbound function of their organization with AI. I'm talking a company that sells to enterprise buyers that says salespeople are no longer allowed to touch buyers that come to our website and sign up to get our free content. Or in another client, it's a sort of PLG-led motion.
14:42If they are signed up for our product, we don't want salespeople interacting with them. We want the AI to interact with them when they're on the site, through the chat, through the emails, et cetera. and there's this big promise that you know a lot of these companies i won't mention the specific ones but these vendors have promised that you know this is going to be the new thing this is where pipelines are going to come from etc and then like a year into that a lot of clients are also seeing that this didn't pay off the way that it was supposed to yep and they're bringing sales people back in that's like one narrative that i see the other one is around like i don't know maybe and maybe this is a really good place to start.
15:22My sort of thesis on the full cycle seller, the account executive, if we're talking about software, I think AI has made their job much more complex. I don't think it's made it easier. And I don't think it's made them more effective because if you look at the data, companies are not seeing higher quota attainment and they are not seeing an increase in per rep productivity. Like the account executives are not producing more revenue with the advent of all this. And basically the attitude is, Hey, we're using AI. We're getting you clawed. We're doing a lot of the stuff that's centralized at the company level.
15:56And because we're doing that, you now need to do more. So your quota is higher. I'm seeing account executives that have to do more self-sourcing of their pipelines because they're getting rid of SDRs. And the third troubling thing is now they're, I think it's a quarter Iconic just put out a report. I think it's a quarter of companies are asking account executives to manage the renewals and expansions too. So I'm like, holy shit, how are you supposed to do your job? So what are you seeing with like AI and what, you know, what are we making a mistake of like following again, based on like all of the history and like all of this other kind of stuff, what are you seeing?
16:32I've been talking a lot. No, it's funny. Like I, I often joke the phrase salespeople ruin everything. Yeah. And I, we've talked about this idea that, you know, in my home, I've got a fully restored 1908 phone. And I have it up there as a reminder of salespeople ruin everything. And here's what I mean. You know, we talk about this great technology revolution right now, like, oh, it's changing everything. And it's the greatest change in technology and sales in the history of the world. No, it's not. You know, 1908, or I'm sorry, going back further to the notorious AGB, Alexander Graham Bell. Okay.
17:11You know, 1876 makes the first phone call. That revolutionized sales more than anything in the history of the world, right? And it's this idea, this incredible gift given to the sales profession that no longer, before that, salespeople, you had to travel. You had to go face-to-face. Think about country roads in the fall. You'd have no weather app. You're out in the middle of nowhere visiting farms trying to sell stuff, and a storm blows in and you're like, hey, can I spend the night? And hey, do you have any coffee? You want cream in the coffee? Yeah. And they go to the cow and they pull it right out of the oven, right?
17:48Like that was the way you sold. It revolutionized everything. You could make 50 calls in a day instead of seeing 10 people face to face. We ruined it. And the lesson back then was scale, right? Like the minute we think that that word, that, hey, we're going to use this technology to scale. And as a result, salespeople, your number's going up. We expect more out of you. And that always breaks it, where AGB would be rolling over if you knew that not only did we need technologies to prevent salespeople from destroying this technology, like caller ID, Dr. Shirley Jackson in the 1960s created that.
18:30That didn't work, so we needed the government to get involved. So the do not call registry comes in. AGB would be like, wait, there's 220 million phone numbers on that. 220 million people were like, stop calling me. And we needed all kinds of regulation around it. We did the exact same thing with email. We get this other incredible gift, right? Like, Hey, now I can send you a note, hit send. It shows up instantly in the person's inbox. How cool is that? Let's scale it and let's use that. And I expect more out of you salesperson. And all of a sudden, we use it for evil, not good, and we need technologies, and we need the Can Spam Act to prevent salespeople from using it.
19:11We're repeating that again with AI right now. Yeah. That we get this incredible technology, and hey, let's use it to get more out of salespeople. Let's use it for evil, not good. Our brains make maps. You can recognize when something was written by AI, when you're talking to something by AI. I just had a post on this actually the language it is like um what's a uncanny valley you know that like we see something that looks like it's trying to look human but not quite and just like bugs the shit out of you exactly I see this in the writing now too always I mean if you think theoretically large language models they're all going to sound the same that's the goal because it's just like that's what's going to happen and we're all going to be able to recognize it like Like they got to fix that if they really want AI to feel like I'm having a human connection.
20:02So I start there. Like technology for evil, not good, never works. We've seen it over and over again. We saw it with video, right? Like I remember when I was a CRO and I'd get these videos from people. I don't know if you ever gotten one of these where it's somebody and they've got in the background. So the green screen, the background is my LinkedIn profile. Yeah. And they're like, hey, you, I was looking at your profile. I wanted to talk. And it was like, they're scaling this by just swapping out the background. Dude, they have stuff now where it'll like you record your voice into something and it does the voice in the name for you.
20:37It's insane. Which is so, it's so insincere and gross. Exactly. Exactly. So the other piece, I got to grab this again because I was showing you before we hit record. This is 1910. Yeah. Thomas Herbert Russell, salesmanship theory and practice. And what I specifically pointed out to you is four words, buyers no more nowadays. Yeah. So 1910. All right. So part of the reason I bring this up is back then you had the advent of mail order catalogs. Yep. Sears Roebuck, 1908. I have one in my collection. It's 1 ,400 pages long. You can buy everything. And it's like Amazon in printed form. And the argument back then was, what are we going to need salespeople for?
21:22buyers can do all their own homework, the sales profession is going to be in trouble. What happened? The opposite happened, right? The profession grew and flourished. You fast forward to 2015, so just 11 years ago, Forrester issued a state of sales report where they said by 2020, 1 million B2B sales jobs would go away. And hundreds of thousands of college students wouldn't graduate into the profession. Why? Buyers knew more and they wouldn't need you anymore. What happened? The opposite happened. Yeah, definitely. So wrapping this piece up, the story has been over and over exactly the same is more information available to buyers has never made it easier on them.
22:06It has always made it harder. And the answer has always been service. The answer has always been salespeople flourish and continue to flourish and will continue to be needed when they look at their role as being the homework doers. The people that go through all of this stuff and go, hey, you got all this information here. I've helped customers like you a thousand times. You've probably never bought this stuff before. Let's call through this together. Pros and cons, the risks and the rewards, the bumps that are going to happen in the journey. I'm going to do that homework for you, and then you can go check and make sure I'm not full of crap.
22:47When we do that, customers not only want to connect with us, but they buy faster, they spend more, and they advocate for you. I believe that that's going to be the answer. It's always been the answer. Maybe AI is different. I doubt it. I think we're going to have that same experience again. Service always wins. Yeah, 100%, man. And I think Gartner really kind of nailed this a year or two ago with their analysis of really the problem for the buyer not being around, do I acknowledge I have a problem or not? It's how do I figure out what the right solution is? Because if you look just in software, for example, I mean, like every single category is extremely crowded.
23:29It's even worse than services. We're filling every available gap in the sales process with technology. And I'd argue that's not a good thing. Yeah. So if a CRO, VP of sales is listening to this, what is the lesson and takeaway around AI for their org? How should they be thinking about it? Well, I think I'm certainly not the only one saying this over and over again. But A, if you're using it for scale, I think stop it. Like take a step back. Scaling your salespeople. Now, if scale means helping more customers achieve optimal outcomes or achieve things they never thought possible. Yeah. Cool. That's great.
24:10I mean, the way that I use it, and I don't feel gross doing it, is I do it for my research. I do it for my homework. I ask the questions ahead of time that I plan to ask the customer during any kind of discovery, so we're not having stupid conversations about, hey, what is it you do? Like, stop it, right? Like, you use AI to do that homework and prepare and have more intelligent conversations that get to the meat and the heart of what the customer can possibly achieve. I think that's awesome. That saved me so much time. But to use it to scale and to automate being a human, the term personality, or I'm sorry, personalization at scale is like the biggest line of crap.
24:52If you're going personalization at scale, think about what you just said. Yeah. No, totally. I want to get kind of your hot takes on a couple of things. So what are your thoughts on the AI SDRs? Ah, gosh, I don't know. I just, maybe. Are any of your clients using it? Not that I know of. Now, I know a bunch to your point did. And you'd see people posting about how proud they were on LinkedIn. And they've all gone away from it. I don't understand, again, because what SDRs using AI at scale are doing is trying to do personalization at scale. And again, I just think personalization at scale goes against everything that we've learned throughout history with all of these technologies.
25:40Remember when the phone call robots were becoming a thing? I remember even when I was younger, you'd answer the phone and it'd be like, hello, you. We are going to have a representative in your neighborhood to sell you aluminum siding. Oh, really? Cool. Tell me about it. That's ridiculous. And AI is just a step further on that to me. And people rejected it. And they rejected it over and over again. And it's amazing that we have to go experience that ourselves to learn that we're probably going to reject it again. The only time I've seen this, and I'll use work in quotes, is very high volume transactional SMB type of sales motions.
26:22because you have to have so much volume with a success rate of 0.1%, 0.3 % in order for you to say that this has a positive ROI. Look at your spam email inbox for all the porn messages, right? Like they send out$100 billion and it must work. They get 0.0001 % to go, yes, get me some, that it works. I think we're thinking that same theory. And what happened to that? Clearly that doesn't work. What are your thoughts on the AI coaches? So those tools that, hey, for example, part of your onboarding process with a new rep could be to supplement some of the FaceTime they get with a manager with, hey, you were just taught how to ask these open-ended questions here, practice that with the AI.
27:12What are your thoughts on the AI coaches? Well, first of all, I always felt as a CRO and then longtime salesperson that role-playing in front of my peers, I don't think that that is a good representation of what selling is. It's like we're not focused on the connection that I'm having with my customer. I'm focused more about, am I going to look like an idiot in front of my peers? And we don't learn much. So I love one-off individualized type role-playing. And if you can create a type of environment like that where I can have a comfortable conversation that feels somewhat real and practice, I'm all for it.
27:52I don't think most of them are there yet. I just had a CRO buddy of mine that told me that he was using one of the popular technologies for that. And he was being kind of a wise-ass in it. Yeah. And so he's having a conversation with the guy about his problems. And at one point, he sent me the recording because he was like, this is hilarious. But the recording was like, oh, I have this problem and this problem and oh, I really have this problem. And the CRO to it was like, oh, I'll bet. And then the thing responds, I'm sorry, my name is actually Mark. Yeah. Like what? Like it's doing a lot of, there's some like false things that are going on.
28:33It's not quite there yet. But in theory, I think it's a good concept. I just don't think it's there yet. If you would have asked me this six months ago, I'd have been like, you know, because I, you know, demoed some one of my friends as a VP of sales at one of of these companies and we were demoing it and we were doing like a multi-threading kind of conversation. Like, Hey, how do you, you know, sell the person that you're talking to on the benefits of involving some of their team, just from a buy-in standpoint and aligning that to a better outcome from your solution. And it just totally missed on that.
29:03And then we just started partnering with this company. Um, and like, dude, I was, I'm really fucking impressed right now with it actually. Yeah, it's getting there. This solution in particular, like you can literally on the backend upload all of the context around our methodology, our outbound pipe gen methodology, and then add in layered customer context too, for the client that we're working with. And it just absolutely nailed everything. And was it like still a little awkward and not quite human in your time? Yeah. But for practice purposes, I was absolutely blown away. I think it's a great application.
29:43Yes. I also had a VP of enablement at a client really challenge me on, because one of our programs is to, after we build the outbound playbook, train your team on it, train your managers on it. The second phase of that is how do we then build a certification process and an onboarding process so that every single new SDR and AE gets certified on this? And we capture that. And she really challenged me. And she was like, this all looks great. Like you're going to create better content that we can. We could do 78 % is 70, 80 % of this, but how are you incorporating AI and like role plays and coaching?
30:19And we weren't at that time. And I was like, yeah, we need to do that. I think it's getting there. I think it's where chat GPT was like a year and a half ago where it was like, okay, cool. There's some cool stuff that it's doing, but it's not really that useful. Um, I think it's there. Um, what are your thoughts on AI in terms of, because there's a lot of talks now around centralizing AI at the org level and thinking about what the org can do and leverage AI for on behalf of the rep versus last year, the trend was let's just get everyone a chat GPT account or a cloud account right now and let them go ham and do all this stuff on their own.
30:59Like what trends are you seeing and what are your thoughts on centralizing some of that stuff? And what are you seeing orgs do for the reps versus just getting them a clod count and letting them do account research and stuff. You know, I wish I had more of an opinion on that one. I'm probably not the expert on it. With the clients I've been talking about, I have not heard that conceptualized much yet. Are you hearing that? Oh, yeah. I think that people are talking about it a lot, but very few are doing it. Okay, yeah. So to give you like an example, like let's use your four levers negotiating.
31:34what would be really cool to do at the org levels if you were piping in your salesforce data you would make it like mandatory for the rep to role play that conversation or at least go through the talking points or how maybe it's not a role play like an actual negotiation conversation maybe it's hopping on a call with the ai coach and it's just like checking to see like hey what's the strategy here like how are they talking about the levers like that sort of stuff would be really cool i I think, to centralize where you're not relying on the rep to know what they're going to bring to the table, but you're arming them and like using this to train them on it.
32:08Yeah. That would be like a really cool use case, I think. I've seen a number of organizations that are pulling their gong data and the conversations that the reps are actually having with the customers and then processing it through AI and doing coaching based on that. I think that's a great application for it. Yeah. But yeah, the four levers negotiating has become something that over and over after I teach a company, they're sharing back with me like, this is how we incorporate an AI and this is what we're doing with Gong. And this is fantastic. That's fantastic. Yeah. So cool. And then the other thing would be the grunt work around like, you know, why is it not standard practice for all of the account research that you would do prior to an intro call?
32:46Why are we not just preloading all of that into Salesforce for the rep? And then they can fine tune and like do other stuff. But why are we not preloading all of that?
32:56So anything else around AI that we should be cautious about? Now, I think we've nailed it. I mean, at its core, again, the idea, I think you mentioned Gartner. Gartner comes out with that report every year that's like, you know, buyers are further along in their buying process than ever before. They're 72%. Like, of course they are, first of all. It's always been like that. And it's always been like that. There's a story I was reading in a magazine from 1927, so 99 years ago, where they were talking about these manufacturers, the executives at manufacturers that would go down to the guys on the floor that are working in the shop and go, hey, order me this catalog, this catalog, and this catalog from these different vendors.
33:40And when you get them, just bring them in. And why would they do that? So that the reps didn't start bothering the executives. They would bother these guys and go, oh, that's just the guy that works on the floor. And they're trying to do their homework without having salespeople. That was 1927. It's the exact same thing over and over again. So just remember, AI is not the death knell for sales professionals. More information has never made it easier on them. It has always made it harder. And the answer has always been service. Yep. Service. It's the transparency stuff that you talk about a lot.
34:16And then the trusted advisor thing. Like being an incredible person to talk to. Let's talk about some of the other areas that you like to talk about that are like these age old topics that we got right a very long time ago and like kind of forgot some of these lessons. Forecasting. Let's talk about that. Yeah. So it's funny that when I read all these old books and go through all of this stuff, the challenges and issues that sales organizations face today are exactly the same. but no different. The objections are exactly the same. There's a book from 1910 that lists out every objection and has answers for them.
34:58And they're the exact same. Like they still are. We're either all set. Like we already have a solution. We're not interested for whatever reason. Send me some information as a no, or I'm too busy, right? It's those four categories. They're the exact same 115 years ago. The one thing that I don't find that's a challenge today with most sales organizations that I don't see as an issue back then was forecasting. And so I just started to try to dig into like, why would that be? They didn't have CRMs or Slacks or Gong or anything AI process. How could that be possible? And I think I put my finger on it.
35:37And it starts with the idea of, remember the movie, Glen Gary, Glen Ross, right? And there's a scene that Blake from Mitch and Murray, he's like always be closing with this gross. Like the whole scene is gross. Yeah. It's very entertaining, by the way. But very gross. Go to YouTube and just put like Glen Gary, Glen Ross scene and just be prepared. You might cry yourself to sleep after it. But he on the board has something called AIDA on it. Yeah. And AIDA sounds so dated, but he actually got that right. And here's what I mean. He got one word wrong in it. But AIDA was originally theorized by a guy named Arthur Sheldon in the early 1900s.
36:18It's copywriting, right? Well, no, it was based on the idea of buyer behavior. Okay. And that all buyers go through four stages, right? First thing you do is you're paying attention. Like, are you paying attention to what I'm talking about? And then we generate an interest or we don't. And then we generate a desire or we don't. And then we take action or we don't. That buyer behavior focus was the foundation for every sales process in the early 1900s, meaning recognizing the words and actions of buyers and proceeding according to that. And it was the foundation for every forecasting methodology through at least the 1920s.
37:03meaning forecasts. When is a buyer going to buy is based on who knew what the buyer is doing. Their words and actions. You fast forward to the 1990s, you've got Siebel and Salesforce and HubSpot. They're coming out with the sales processes are all based on what sellers are doing. Yeah. Right. Which is prospecting, qualification, discovery, demonstration, proposal, negotiate, close. Yeah. What we're doing, our forecast became based on that. The endorphins that we get are in the process of proceeding a deal are based on what we're doing, not recognizing the words and actions of buyers. And as a result, who knew that our forecast would be less accurate when we're paying attention to what we're doing instead of what the buyer's doing, right?
37:49Like that's, and as a result, our forecasts have gone off the rails and we go, well, you know, we're a buyer centric organization. Sure you are, but your processes and your structures and your forecasting are seller centric. I think we're buyer centric in name only. So what I did in my last company is I layered. So we had our sales process. We had our stages, right? Discovery, qualification, all that stuff. We were not going to blow that up. But what we did is we layered buyer behavior over the top. And that buyer behavior was not AIDA, but it was the three whys, which is why change? So a buyer first goes, my status quo is maybe not sustainable anymore.
38:31I need to do something about it. And then we go into why you, so solution versus solution versus solution. What is the right path to address this unsustainability of my current state? And then once we decide, we either pull the trigger or we don't. And we layered those over the tops of our stages. And all the leaders were enabled and taught how to recognize buyer behavior. They taught their salespeople. And as a result, our forecast, six quarters in a row, was within 3.5%. Wow. And I believe that's part luck, right? But part buyer-centrism. And we're predicting what buyers are going to do based on what they're doing, not what we're doing.
39:14Yeah. That's what they did. literally there's a book in 1925, Elmer Ellsworth Ferris wrote in his book, he's got AIDA and under it, he's like, I'm not even going to explain what AIDA is because everybody who knows anything about sales knows that all buyers go through these stages. Here they are. Right? And then we somehow lost that. Yeah. It's not that hard to fix either. Layering that over your current stages and then teaching your reps, here's what buyers are doing. Here's what we should be doing to support them, not the opposite, which most companies are doing, which is, hey, here's your milestones that if you haven't done this, don't move the deal forward.
39:55Who gives a shit what you're doing, right? It's what the buyer is doing and it should be buyer milestones, not seller milestones. Yeah. There's so much, even I see in very large organizations where there's not basic entrance or exit criteria at the stage. So there's no like action. And the criteria is got to be buyer-centric, not seller-centric. So an example of this would be like buyer has an existing business priority that they've agreed is aligned to this solution. Like our conversation is tied to something that they would agree with as a problem for them. It could be, yeah. A multi-threading thing could be like they've looped in so-and-so on their team or the economic buyer is aware of the conversation.
40:36There is an existing project in place. Love that. I'm curious, do you think there's a proliferation of this because when i think about sass there's all this vc and pe backed type stuff where dude god i'm not shitting you man i did a pipeline analysis with a client this is like last year this is a company that crossed 100 million in ar last year we were doing a sales stage analysis 80 % of their pipeline was like a deal that was in a stage for more than six months that had not moved, that had not had any previous activity on it in several months, no next steps, et cetera. How much of this is just like, oh, I can't report.
41:22I can't, dude, we can't clear out 80 % of our pipeline. I'm going to get fired if I bring that to the board. Is there any of that Like pressure, I mean. All right, pull the string, brother. I got a lot to say here. I mean, first of all, words and actions of the buyer. The key one is evidence of a buyer's engagement in what we're selling is shown in their willingness to put you in their calendar for another conversation or meeting. Yeah. Right, like that's the single simplest buyer behavior recognition that should be indicated on our forecast all day long. Like if you don't have next steps with a customer and they're not willing to put you in their calendar for another step, are they engaged at all?
42:03Like that's insane to me. Like that's step one. But step two is a mistake that I always made. And I readily admit it. This is the philosophy. And I don't mean to offend any of your sales leaders that are doing this today. And I know you are, because I talk to you guys every day. I used to drive down into my sales organization that at all times you have to have 4X your quota and pipeline. Right? Like you've heard that all the time because we close 25%. We need like that gives us enough pipeline and it's always more pipeline, more pipeline, more pipeline. Now, if you're a salesperson, what does that incentivize you to do?
42:42A, fill your pipeline. Yeah. B, doesn't matter if it's a real pipeline because what you're looking at is the number, not the quality. So it's filled with absolute crap. And as a result, what are we also doing? Your most valuable asset you can convert to revenue as a salesperson. And you got your inventory of your selling is your time. It is never going to be any earlier than it is right now. Yet the Forex philosophy teaches salespeople to lose slowly and to hold on to deals that actually don't exist much longer. and the result is your forecast is completely inaccurate. I think we need to get away from this idea of the 4X pipeline and get to - It's like 5X now.
43:31It's probably 5X, it might be 10X. It's crazy. And as a result, again, we've got an ugly pipeline that's not accurate. We're working deals that we should have lost long ago. Wouldn't it be great if we could get to 2X and get to 150 % of our number? Why not? I believe that that's kind of the core of the transparency sale is this idea of the greatest thing in the world is winning. Second place, lose fast. Yeah. And be honest with our customers. Here's where we're great. Here's where we're not. Every lead has a cost. I could go on and on there. Like I said, pull the string. But I also look at this idea of my board meetings.
44:14I remember going into a board meeting once, and we were doing really, really well. We were Chicago's fastest growing tech company, according to Deloitte, for a couple of years there. And I remember walking in and we were looking at the numbers. And my board was like, Todd, what's going on with marketing? I can see that your pipeline load is lower than it's ever been. And like, is marketing not doing its job? Where do you need help? Should we be worried six months later? And I was like, dudes, I'm excited about low pipeline load. They're like, what are you, you lose your mind? And I was like, no, because I know that every deal in there is real.
44:49And I know that my reps are working on the right opportunities. We're not going to win all of them clearly, but we're working on the right opportunities. And as a result, my organization, my team is becoming incredibly efficient. Lower pipeline load. Each one of those deals is of a larger dollar amount. Each one of those deals, our win rate went way up, way up. And because we were working on the right opportunities, our cycle links went down too. because we were able to make our customers smarter about their business, not ours, because we became experts in the types of deals we should be working on.
45:23And as a result, our growth rate was insane. I think that that goes back to that core concept of forecasting inaccuracy starts by making it seller-centric. But we are measuring the wrong things when we are focused on pipeline load instead of pipeline quality. Yeah. So quickly on that topic, then how do you recommend that these senior leaders think about pipe gen? Because that's like such a big, almost, I mean, naturally, if an organization comes to us, they're, they're needing help with pipe gen, but how do you suggest that they measure and incentivize and do this in a way that's putting quality pipeline in?
46:04Because I've always, the pipeline coverage thing never made sense to me. Right. It's never made sense. Well, I would go back to this. Like one of my core concepts as a revenue leader myself was celebrating the losses. And I know that sounds crazy. I remember I was teaching the leadership, the sales leadership team at SAP once. And I said that, and there was somebody who was just like, we're going to create a culture of losers. Like, no, no, no, take, take it easy for a second. Yeah. Here's what I mean. I've been around sales leaders my whole career where when you lose a deal, it was either A, you lost because you got outsold.
46:39Yeah. And as a result, salespeople, every loss was because the customer's an idiot. Like that was their excuse. Right. So like that's number one. Number two is best case scenario. You lose a deal and it's patchy on the back. All right. Better go get them next time, Jason. Like, yeah, good luck. I had a philosophy that we would celebrate the losses, meaning there was one long story, but the short version is my old CEO was old school. And when we lose a deal, he would want to kick your ass. And so I get there. One of the first big deals we lost, I had the rep come in, we threw him a champagne toast with everybody.
47:17Like I was being a jackass, but I was doing it on purpose. Cause I was like, we have to change our culture of forecasting and learning from our losses. We're going to celebrate it a for the effort, right? He's already getting punished by quote attainment. He's not going to get paid for this deal, right? Like he never gets that inventory back of his time. Probably not feeling great either. Exactly. But number two is let's celebrate for the lessons that can be learned. I know that's an old school philosophy, but we were celebrating him getting up in front of everybody and going, and here's why we really lost.
47:51Here's the circumstances in their organization that probably led to it. Here's what I wish I would have done earlier, seen earlier, said earlier. Here's why there might have been an opportunity to qualify out earlier. My RevOps guy would be sitting there going, hey, we got a deal that looks like that here, here, here, and here. Let's talk about those. Right now, let's get ahead of them. And the next thing you know, we're not losing for the same reason over and over again and having no idea. Yeah. Like that's the point is these lessons learned had to be very specific. We'd celebrate louder when the rep is willing to admit a mistake they made.
48:27We stopped making the same mistakes over and over again, but we got really, really tight in recognizing what a good deal looks like and what a good deal does not look like. And again, instead of just having a ton of pipeline, we had high quality pipeline, maybe a lower amount, but we were closing them more often, bigger and faster. Yeah. It's just such a better life to live as an enterprise rep too. Be celebrated for your loss. Now, if you're making the same mistakes over and over again, that's trouble. But for us to be airing those and sharing those and then tying them to firmographics and demographics of who we're selling to in the accounts and prerequisites, what does the environment look like in those accounts?
49:05We got really, really tight on what to look for. We got really, really tight on what a good deal looks like. We got really, really tight on being able to go into a customer when we see this kind of thing and go, Hey, listen, before we get too much further down the road, there's something that's coming up in accounts that look like yours in circumstances that look like yours. And it's this, is that going to be a problem for you? Cause let's address it now versus six months from now, after I got an RFP team that just replies to your RFP before I fly people all over the place, is this going to be a big deal?
49:36Get the elephant out of the room before it crushes all the furniture. Yeah, absolutely. One last question on this. For an organization that wants to adopt an approach that's more like this, what's a baby step they can take in this direction? Well, I think that there's really two things. Look at your forecast stages and it's not hard to layer in buyer behavior over it, right? Because you've got your seller, what seller should be doing? Why change? Why you? Why now? Put it over the top. And by the way, don't mistake this. I I now does not come before YU. It doesn't. If you look at consumer behavior, the number of people that go online and shop and then put something in their cart and abandon it is like 68%.
50:21So they're like, I need something. I picked what I want, put it in the cart, I don't buy. All right, so that's step number one. Step number two is to just look at your culture. All right, that the pipeline load issue is an easy one to start addressing. Celebrate your losses And then can I go on one last quick rant? Yeah. I think the word commit is a Petri dish of lies in your selling organization. That when we force reps to commit publicly to a number or commit specifically to deals, we are incentivizing them to lie. Yeah. Right? Especially if you're doing it with your peers. If you've got a crappy pipeline, I'm not going to get in front of my peers and go, I'm not going to do anything this quarter, so I'm going to lie.
51:06Yeah. And then if you've got a rep that's got a huge pipeline, they're not going to go, hey, I'm going to do 300 % of my number. They're going to be like, I'm going to do 120 % because I don't want all the eyeballs on me. And so that's lies. Number two is when we do deal-specific commits. A, you're committing to something you possibly can't commit to. That's broken, number one. But number two, more importantly, if I've committed a deal to you and you're my boss and it starts going off the rails, who do you want the first person that rep goes to when there's something wrong with their deal? You as a leader, right?
51:42Come to me when there's something going on. But when we've committed that deal and we've created a culture where you committed that deal, you better find it. Yeah. You're the last person I'm going to as a sales rep. I'm probably going to go directly to the customer and see if I can discount her. I'm going to try to salvage it, save it. because, oh my gosh, I committed this deal. And it goes off the rails either way. Yeah. Replace the word commit with something else. I believe that even a deal where customers said, yes, we've gone through the whole contract. I've delivered it to you via DocuSign.
52:13Nine out of 10 of those deals close. Yeah. That means one out of 10 doesn't. But a acquisition happens, executive leaves, like that kind of stuff happens. You can't even commit a deal I've sent you via DocuSign. I don't believe because you don't have control over what could possibly happen. And as a result, we're sending the wrong signals. But again, we're forcing our reps to go to the wrong people, to lie intentionally. And as a result, I think that's throwing off your pipeline load and your forecast as well. Dude. Love it. Let's talk about quotas. Okay. Quota setting. Yes. I mentioned the stat around attainment being as low as it's ever been, but that doesn't really tell the whole story, right?
52:55I mean, if the expectation is that a company is going to increase quota, sometimes on a quarterly basis, but every single year, and they're putting these impossible numbers in front of reps, yeah, of course, fewer of them are going to hit attainment. But there is another part of it is how much of this is like the skill of the reps, the lack of enablement and training, the system, the infrastructure and how it's set up in a way that really doesn't incentivize the behavior that they want. But this is another thing that you've talked about that just like, hey, we've already figured out this problem, you guys, a long time ago, actually.
53:30So what are your thoughts on quota? Yeah, it's funny. Like we were talking about AI. Let's go back to the 1920s. And by the way, in my collection, I have multiple books from the early 1900s on setting quotas and compensation plans. Yeah. Like it's crazy. So mid-1920s, you had sales quota specialists that were hired in organizations like data scientists back then. because getting quotas right was the most important thing you could do. Not only from a forecasting perspective, but from a seller engagement perspective. So what did they do? Well, 1920s, territory-specific quotas. Each territory had a different quota.
54:11How would they do that? Sales quota specialists would go into the territory and pull all available data, 1920s. So let's say it would be how many companies are there? What are the demographics of the people in the community? What is the total dollar amount of deposits from companies in that community? What's the makeup of the community? How many of these people can read? There's things like that. They would do all this data, collect it. They would come up with a number based on historical perspectives and anticipated growth. And then they would say, all right, Jason, here's what we think you're going to be able to do this year.
54:46What do you think? and then before we'd set the quota, we would sit down and we would collaborate on it. They did so much more with so much less. They set territory-specific quotas, and as a result, their reps hit the quotas. They were proud of it. In some cases, reps are like, I think I can do more than that. The quota you gave me, come on, bring it. And as a result, turnover would be lower. Engagement would be higher. Desperation would go down. I think it's incredible to me that they did that back then. And we fast forward today when we've got so much information. We have all the information.
55:26Exactly. Like, why are we keep going back to this top down? Hey, we did this number last year. Let's just add 30 % to it. Yeah. And split it evenly among everybody where at the beginning of the year, I'm disenfranchised because I'm looking at a number I know I can't attain. So part of me is working while part of me is making sure I've got my eye out for my next job when I'm about to get fired. Yeah. Turnover goes up. Time to recruit goes up. Like it's a big disaster. Bottom line here is they did so much more with so much less territory specific quotas and alignment rep by rep at the beginning of the year so that you were bought into the number.
56:02Yeah. The last piece on that is in many cases there was quota and there was goal, two different things. Quota was here's how much we need you to bring in to essentially pay for yourself. Yeah. Right. You become a profitable piece of the organization and therefore we can keep you. Yeah. And then here's your goal. Here's what we think you can really do. And sure you can stretch, you're going to stretch to it, but you're going to be rewarded when you get to that stretch. Gosh, why is that something we can't do today with data science and AI and all this available information when they could do it a hundred years ago.
56:40Yeah. How does this happen in practice with like your clients and stuff? How do you, how do people normally set the, I'm not, well, I mean, what I see in most organizations and every organizations is a lot of head nodding when I give that rant, like, oh yeah, it's a great point. And then they can't do anything about it. Right. Like I waiting for somebody to go, all right, let's fix this. Let's do this. Let's be the company where most of our reps are hitting quota and yeah, maybe we still have 60, 50 % hitting their goal that we split that out, but we give quotas that are territory specific and it doesn't have to be wild variations, but it should be based on the data and the territory and what that, I mean, John Patterson was doing this in 1895 where he was looking at how many businesses are there, how many people live in the community.
57:33We should have one cash register for every 200 people in the community. and that should be your number. So how many people are, you've got to get that many. Yeah. I have not seen anybody really grasp this yet. I've seen organizations and leaders that have been more forthright during the interview process around, hey, top rep did this, bottom rep did this. Here's how many people didn't make their number. Here's how many did. Here's the difference between those and doing that in the interview process so that they're setting accurate expectations. But again, there's nothing more deflating than being given at the beginning of the year a number that you know you can't hit.
58:10And I would argue that you're doing that to at least 50%, maybe 80 % of your sales reps the beginning of every year. Yeah. I wonder how much of this is pressure from PE and VC firms too. It could be. I think more it's just easy. Yeah. Right? It's easy to go, hey, it's just math. We got to hit this number. We got this many reps. Yeah. So this number divided by this many reps, do some over assignment so that, because we know reps are going to leave. We have some reps are going to come in. We're going to recruit. And there's your number. We're done. I just can't believe that it's. I can't believe that that is.
58:51That's how little effort goes into this and how little expertise is being applied. I've seen the spreadsheets too. It's just like a spreadsheet equation. And it's wild, man. I remember my CFO meetings, man. Like I would go into them like, all right, show me the spreadsheet. And then smoke would start coming out of my ears and I'd be like, all right, whatever. Just what's the number? Like that was what we did. It's crazy. Managing the morale on a team where less than 50 % of people are hitting quota is just insane too. Can I share one other piece of that? I think it's funny to me. Maybe it's not funny, but can everybody just think about what we're about to do here at the end of the year and the beginning of next year that we've done every year for the last hundred years, which is the year ends, and then we start everybody over at zero, right?
59:40So everybody starts over at zero. Two things here. Number one is there's a guy named Dan Ariely. He's a neuroscientist out of Duke University. Yeah. He had done a study. It's shown in it. It's got a book called Payoff, but he shares this story of a study that was done where a bunch of people were brought into a lab and they were asked to build bionicles, which is kind of like a complex Lego model. These people would come in, they would be given the box and go like, put it together, I'm going to pay you for every one you complete. And then I'm going to give you another one. And when you build that, I'm going to pay you a little less, but keep building and tell me when you're done.
1:00:23And so that was both groups, right? Group number one, these people were building the bionicles and then when they would get done, the bionicle would be put on a shelf right behind the practitioner for everybody to see and then given another one. All right? So that's group one. Group two, same exact job, same exact bionicle, same exact pay. But what was happening after they built the first one is they start building the second one. The practitioner is disassembling the first one, putting it back in the box. Then that'll be the third one I give you. Right? And then keep doing that. So instead of it being on the shelf, it's being disassembled.
1:01:03Yeah. Now, what do you think happened? Well, group one built twice as much as group two. Group two quit twice as fast as the first group. And the only difference was could they see what was being built versus it was being disassembled right before them. Yeah. I would argue that in the sales organizations, we're asking them to build as hard as they can all year. And then because the calendar flips, we disassemble the Lego model right in front of them and go, all right, build it again, build it higher, and I'm going to pay less for it this year. We're doing the exact same thing. Now, I'm not saying that we shouldn't reset the score to zero, but we as human beings, we are much more willing to work harder when we can see the fruits of our labor, when we can see what we've built.
1:01:53we can see the contribution that we've made to the organization. I think there's a huge opportunity for organizations to take pride and build pride in the reps that are the ones that are building the organization for all to see. Your reps will work harder. They will stay longer. They will take more pride in helping the organization continue to build. Last point there, just remember when you start everybody at zero, you are rewarding your bottom performers and you are penalizing your top performers. Yeah. Because the bottom performers like, Hey, look at me. I'm at, I'm even with everybody again.
1:02:29And your top performers are like, Hey, look at me. I'm even with that jackass, right? Like we're doing that over and over again. I just think there's such an, like what we used to do, we did lifetime achievement awards. We did awards for reps that were making multiple years in a row. we were giving that in their titles, in their pay, making sure that everybody saw it. Like, there was a rep named Jen that worked in my organization that everybody would look at, like, look at her, man. You know, that target and that customer and that customer we've got, she closed those. Right? And she would walk around like, yep, there we go.
1:03:04I think that's just a huge opportunity missed. Yeah. There's a whole like building like a legacy inside of your org that I think is missed in software, especially right now where the tenure seems to be one or two years. And why is that? Because we start everybody over and you're teaching your top reps to go, I got to start over again. And they're going to, my quote is bigger. So I'm building a bigger bionicle and I'm going to get paid less because my quote is higher. And as a result, my percentage didn't change. It's the same thing as Ariely's study. We're incentivizing our reps to go, do I start over here or do I start over over there?
1:03:39Yeah. Good stuff, man. Dude, this was awesome. Uh, I got some surprise rapid fire questions for you. All right. Okay. So I'll start, start up with a fun seatbelt. I'll start off with a fun one. Um, what's like your fuck you money purchase? Oh man. Um, well, I mean, I, this is going to sound arrogant, but, uh, I was on ExactTarget sales leadership team and Salesforce acquired us in 2013 for a little under$3 billion. I did pretty well with that. And we bought a lake house. So we've got a place up near Lake Geneva. And that's just like, thanks, Benny off. I will say this. We also bought a boat. And we have it.
1:04:28And it sits out there on the dock. and I freaking hate it. It's like, it's just boat stands for bust out another thousand and I'm living it. For anyone that's listening that's in enablement, which we're both doing the workshops, the coaching, the training, like we're in the business of skill transfer and behavior change and all of that kind of stuff. What advice would you have for someone in that position that is looking to be more effective with the behavior change and everything that they're training and enabling around? Yeah, I mean, the long piece is, so when I got to ExactTarget, I was always a sales nerd and I was asked to run one of the four regions of the company.
1:05:15And very quickly, I noticed that our enablement practice was, it was like really bad. And so I would share that with our COO, the guy who was running all of field operations too. And I was like, dude, if we're going to scale this thing, that's ugly. And he was like, well, then you do it. So I want you to take over. And so all of a sudden I was asked to come to a board meeting in Indianapolis. And it wasn't the board. It was our leadership team. And they're like, Todd, we want to pay you to rebuild enablement. And I was like, that's cool. I'd love to. That's awesome. And then I left and I was Googling, what is enablement?
1:05:51I didn't even know what it was back then. And so what I did is I went on a journey to figure out how people learn and how to optimize for learning. And then how do we build this at scale? Because we were hiring 30 reps a month. Yeah. And so the short version of that is, gosh, learn how people learn. If our responsibility is to enable our sales organization, I mean, obviously there's so many. I could list out 10 pieces of advice there, one of which being your role is really buyer enablement. How do we teach sellers to be better stewards and service professionals for our buyers? But man, if we don't know how people learn and we don't optimize for that, we are just kind of wasting everybody's time.
1:06:40There's lots of good books out there. There's lots of good pieces of information. learn how people learn, and then build your strategy around enablement, around optimizing for learning. And there's so much great science. Exactly. We know. Now with AI too, it's at the tip of your fingertips. Oh, exactly. Think about how babies learn or how you even learn. You have a garbage can out on your deck and it's windy out. You crumple up a piece of paper, right? And you're like, I'm going to hit the can. What does your brain do? It comes up with a theory. based on what it knows about how high, how far, how hard, what direction to throw this thing.
1:07:19Throw it, I miss, brain calibrates and goes, all right, now I know. I'm going to go a little further right. I'm probably going to do a line drive. And then after a couple of times, I hit it. That's how we learn is we teach to theory. We experiment. We celebrate what we did wrong. We learn from it and then we try again. And that's all learning is at its simple point. And in sales organizations, a lot of times training is words, words, words, words, words. Best of luck to you. We'll see you next time. And like, that's not how people learn. We have to adhere to that. I've tried to design everything I do around that concept.
1:07:57But I think enablement leaders, when they do that, they're going to see the fruits of their labor come through much more rewardingly. 100%. Last question is, knowing what you know now, what advice would you give yourself as a first time, let's say, revenue leader? First-time VP of sales, first-time CRO. All right. So for me, when I had first gotten promoted into revenue leadership, it was the most exciting thing ever, right? It was what my goal always was. And then two days in, I felt like I was a dog chasing a car down the street every day, right? It was like different issues. Sales, I had a structure and a process.
1:08:33Leadership, no structure, no process. Get a structure. Get a framework. I wrote it. shameless self-promotion, my second book, The Transparent Sales Leader, is a framework. So it's the wrong title for the book. Sorry. It's my publisher's fault. But there's really five core responsibilities you have as a revenue leader, right? They all fall into one of five buckets. And I listed them all with the letter F because I'm a dumbass and I needed to make it alliterative. But you've got a responsibility to make sure your team is focused on the right opportunities, the right firmographics, demographics, prerequisites.
1:09:07You've established the focus, protect your team's time. No science projects. You then build your field to support the focus. So the field is the team. The right people in the right places with the right tools, the right resources. Once you've built that field, you then have to adhere and teach the fundamentals. So that third F is fundamentals, getting the right things right consistently. Prospecting, discovery, qualification, demonstrating, proposing, all that stuff. Your number four responsibility, who knew, is the forecast. You need to teach people and yourself to predict the future through the right KPIs, the right metrics.
1:09:43And then number five is fun, but fun is culture. You've got to build a culture where your team wants to show up, stay, do their best work every day, advocate for you. Now, when you have that structure, so take a minute, internalize the 5S, right? Focus, field, fundamentals, forecast, fun. You now have a 30, 60, 90-day plan in your back pocket where you can go through and go, how are we doing on each one? it. How do I feel about our focus? The team, do we have the right team and the right tools, the right resources? Are they getting the right things right consistently? Can I predict the future?
1:10:15Do I have a culture where people are talking at parties about how great they think it is here? And then put together a plan around it. And now you are 98 % smarter than every other revenue leader that doesn't have a structure. When the heat goes up in the kitchen, in your board meetings, I used it for everything. It was always the five F's. A lot of like, I remember one board meeting. They're like, is it the five F's again? And they're like, yeah, it's the five F's, right? And then I used it for all my communication. It was the structure and agenda for my one-on-ones. Use that, use your own thing.
1:10:46But if you feel like your one-on-one purpose are to just do the forecast, you're doing it wrong. If you think that maximizing the revenue capacity of your team is just based on pounding harder, I think you're doing it wrong too. Optimize each of those five and things are going to slow down. You're going to see the holes before they form. And so again, I know you said rapid fire and I went wordy, but it's the five Fs internalize those and you're going to be a rockstar and you're going to sound really smart too. Love it, dude. Before you take off, where can people go to connect with you? What do you want people to go check out and make sure to tell them where they can grab your books?
1:11:21Yeah, I mean, the books are available everywhere books are sold. So the Transparency Sale, Transparent Sales Leader, and then Four Levers Negotiating is the new one. toddcaponi.com is a great place to start. I do share a lot of my link, my nonsense on LinkedIn. So if you want to follow along there and then lastly, it's a hobby. I don't monetize it, but the sales history podcast is in season six right now and it's just me. So there's no guests. It's just a monologue where I'll research a topic and then spend 14 to 22 minutes in each episode sharing it. I was just like two doors down studying for my next one, which is about 10 men.
1:11:58so aluminum siding salespeople in the 1950s and 60s and how they were helping to destroy the reputation of sales and it's just fascinating i just finished watching the 1987 movie tin men with richard dreyfuss and danny devito again last night and it's it they're all like that love it dude thanks for coming on man all right brother let's go thanks dude that was fun
1:12:32Thank you for listening.
In this episode, Jason and Todd Caponi from Sales Melon, talk about why AI is just the latest chapter in a story sales has seen many times before. They dig into why more buyer information never replaced the seller, mapping buyer behavior onto your current sales stages, celebrating lost deals to sharpen qualification, and the five core jobs of a first-time CRO.
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