In short
Sales and B2B marketing “courageous” differentiation, AI’s real impact on revenue teams, and building psychologically safe teams for experiments.
Guest backgrounds
Udi (Udi is the host/guest). Chief Evangelist and former Chief Marketing Officer at Gong; author of Courageous Marketing. Helps sales teams understand how AI changes revenue work and advises marketers on making B2B less boring.
Key claims
Salespeople who swear/curse on calls win 8% more deals. Marketing that avoids offending anyone risks indifference; the worst outcome is invisibility. “Different is better than better”: being 20% better won’t stand out; you need a radically distinct angle. AI won’t replace teams by itself; it will replace those who don’t use it effectively. Don’t buy “an AI budget”; build a priority list of business problems and choose AI/humans accordingly. Generic LLMs lack your company context; use dedicated revenue AI trained on your materials.
Notable examples
Gong’s rebrand (fuchsia/purple, drooling bulldog; starburst logo evolution). Viral content on swearing in sales calls (heated debate). Event invite experiment: plain-text personal email led to 700 registrants within hours.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOSales Leaders and AI Overwhelm
0:45 to 2:10
Sales leaders feel overwhelmed by the multitude of AI tools.
“Wehaveameeting.com Udi, welcome to the podcast.”
Courageous Marketing Explained
2:10 to 4:26
Udi discusses the importance of breaking through the sea of sameness.
“I just saw a CRO at another company posting today that in the last two weeks, he had like 30 companies reach out and say, well, just do a pilot with us and just see why we're better.”
Examples of Standing Out in Branding
4:26 to 6:50
Udi shares how they stood out with unique branding choices.
“because, and I'll end on this, the biggest risk of all your marketing approach is not that someone might not like it.”
Understanding Your Audience in Marketing
6:50 to 9:26
The importance of knowing your audience to avoid indifference.
“I don't know that I can draw that line firmly.”
The Power of Controversial Marketing
9:26 to 12:16
Udi explains how controversy can drive engagement in marketing.
“boring practice because everyone is doing it and there's no way to stand out by doing what everyone else is doing.”
Finding Strong Opinions in Marketing
13:15 to 14:09
Guidance on identifying strong opinions and standing for something.
Defining Your Brand Identity
14:09 to 15:46
Learn how to effectively establish and communicate your personal brand.
“Jeff Bezos famously said that your brand is what people say about you when you leave the room.”
The Impact of AI on Jobs
15:47 to 16:42
Explore the nuanced conversation around AI's impact on the workforce.
Two Buckets of AI Applications
16:43 to 19:37
Understand how AI can enhance both efficiency and decision-making.
“So I'll put it in two different buckets.”
Automation vs. AI: Key Differences
19:38 to 22:21
Distinguish between automation and AI regarding their applications in sales.
“But there's sometimes a feeling that I have that sneaks in.”
Show all 20 chapters
Strategizing AI Investments
22:22 to 23:47
Learn how to identify problems before investing in AI solutions.
“First, I would argue with the approach of this is my AI budget.”
Navigating AI in Sales
24:56 to 27:52
Enhance your sales strategy by understanding AI's strengths and limitations.
“Well, the first thing is to arm yourself with a healthy dose of skepticism and understanding, really understanding what are the capabilities and limitations of the different AI tools that you're using.”
AI's Role in Sales Conversations
28:01 to 29:19
Explore how AI impacts the nuances of sales calls and critical thinking.
“I just want to round off the AI conversation, right?”
Balancing Skill Loss and Freedom
29:20 to 31:38
Discuss the benefits and drawbacks of losing certain skills due to technology.
“Is that something that you think about at all?”
Building Courageous Teams
31:39 to 33:43
Learn about the importance of psychological safety in team dynamics.
“Yeah, we should absolutely still teach them how to do that.”
Encouraging Risk-Taking in Teams
33:44 to 36:09
Understand how to create a culture that encourages experimentation.
“Half of them were team members at different points in time.”
Balancing Accountability and Innovation
36:10 to 38:12
Discover how to balance creativity with business objectives in teams.
“Because most organizations have a very conservative, restricted culture where everything you do is pretty much expected to work.”
Successful Marketing Experiment Case Study
38:13 to 41:19
Examine a case where a simple marketing experiment led to outstanding results.
“It's very hard to create that bubble of boldness in a very conservative organization.”
Courageous Marketing Tactics
42:04 to 42:55
Learn how to break away from boring marketing practices with creative strategies.
“And it doesn't have to be something as big as designing your category.”
Finding the Author and Book
42:55 to 43:39
Discover where to connect with the author and purchase their bestselling book.
“You've already given me loads of ideas for the next event we're throwing.”
Transcript
Automatic transcript. May contain errors.0:00Salespeople who swear and curse on their sales calls have an 8 % higher win rate than people who don't. I'm Udi. I'm chief evangelist and former chief marketing officer at Gong, also the author of the recent bestselling book Courageous Marketing. Yes, we are about to be replaced, but probably not by what most people think they're going to be replaced. If your messaging avoids pissing off anyone, the biggest risk of all your marketing approach is indifference. The creator of ChatGPT is not using ChatGPT to run the revenue team. Maybe you shouldn't be using it either.
0:42Udi Ledergor:Our books are now open. If you need help getting in front of your dream clients, we might just be able to help. If you're a business who's wondering how to grow in 2026 and beyond, but there's not enough meetings in the diary with either the right person or the person who genuinely wants to solve the problem, we might be able to help. Wehaveameeting.com Udi, welcome to the podcast. Thanks for having me. I'm excited to be here. We're excited to have you. So we kick off the same way every single time. I'm excited to see where you take it. Who are you and what problem do you solve? I'm Udi. I'm Chief Evangelist and former Chief Marketing Officer at Gong, also the author of the recent best-selling book, Courageous Marketing.
1:28And what I do in my day-to-day is I help sales team understand how AI is changing for the better their world, and also sharing my experiences with marketers around the world to help them take the boring out of B2B.
1:45Udi Ledergor:Nice. Okay, so if I'm a sales leader right now, and let's say I'm probably, I've not dipped my toe into the AI world, but I've read a few posts on LinkedIn, I might have watched a YouTube article. What are you finding that most sales leaders are feeling at the moment when it comes to the response to AI? I think the biggest feeling I'm seeing right now, and I meet with chief revenue officers and their teams every week is overwhelmed with all the tools out there. I just saw a CRO at another company posting today that in the last two weeks, he had like 30 companies reach out and say, well, just do a pilot with us and just see why we're better.
2:26And he said, I don't have time to do 30 pilots. And these tools are not doing a great job of differentiating and showing him what he needs to actually use and try. And so my advice would be to look for a platform that's been around and can do a lot of the things that you need, rather than piloting 30 different tools that are probably not going to play nice with each other anyway. So Udi, I want to start off by coming nice and broad. When we think about courageous marketing, what are we talking about? What's a really good example for the audience to get the head around what you mean? So my thesis around courageous marketing is that a problem that most marketers are trying to solve is the sea of sameness that we all see around us that our audience members see.
3:12And most companies and most marketing teams, they don't do a great job of breaking through that sea of sameness because they're playing the game that everyone is playing. The messaging looks the same, the website looks the same, and they never really cut through the noise. The best marketing teams, those who build courageous teams and make courageous moves, they have a very sharp differentiated point of view and they manage to get it out into the market in a way that really cuts through that clutter, whether in their visual identity, whether in their sharp messaging. And here's something that a lot of people don't really use as a test of this, which I think they should.
3:50If your messaging avoids pissing off anyone, pardon my French, it's probably not going to excite anyone either. Your product is not for everyone. Your brand is not for everyone. And if you try to make it so agreeable that nobody could ever fathom being offended by it, you're probably not going to get anyone too enthusiastic about it either. And so we see that the best brands and the best personas who cut through that noise, they do it by sometimes being controversial or even polarizing, not for the sake of being offensive, but not risking, but not being afraid of taking that risk. because, and I'll end on this, the biggest risk of all your marketing approach is not that someone might not like it.
4:37It's not that someone might even hate it. The worst problem is indifference. If nobody cares about what you're doing, then you're invisible. And that is the worst thing that can happen to your market. Nice, okay. There's some psychology to get into there a bit later on. Just to really define this, are you asking b2b marketers to be more inventors i come up with brand new things or are you saying innovate what already works well that that i think is the second order question of the tactics of how to get there but if i take it up one level i would say that my approach uh has been the different is better than better and i'll explain what i mean by that let's say i'll start with an example and then I'll kind of generalize it.
5:25So when we built our first meaningful website a few years ago, we looked at all the other B2B sites in our space and a little bit broader than that. And at that time, everyone was using what one of my team members called Series A Blues. They all had this shady type of blue that pairs beautiful with white and gray. All looked exactly the same. And it almost seemed like every new B2B website was trying to come up with their own shade of blue to stand out and be different. Of course, nobody was doing that. And so we decided to go the opposite direction. Instead of using the blues that everyone was using, we picked fuchsia pink and bright purple.
6:00And we also slapped a drooling bulldog on it as a mascot. And that immediately helped us stand out. And people were talking about this. Oh, this is very, very different. Let's see what these guys do. Let's track their progress and see what they're up to. And so the point that I was making there, and we've done this many, many times with event experiences and category creation and content material, is not to try and be 20 % better than everyone at what they're already doing, because being 20 % better is not going to help you stand out. You have to be 20 times better to really stand out at the game everyone's playing.
6:33Easier approach in my book is just to be different. And by going the opposite direction, you're now by definition leading that new direction or that new category. And it's so much easier to stand out.
6:46Udi Ledergor:So we're going through a rebrand at the moment. We're rebranding everything. and we have had the feedback in the past that our website and logo is disgusting one of my team actually called someone the other day and they said that they ended up saying where are you from we're from we have a meeting and they said honestly that is the worst company name I've ever heard tell your boss to change it okay so you are right you're not for everyone I guess for business owners especially in the b2b space how do you know when not to how do you kind of not cross that line So be different, but maybe not be so disruptive that it goes completely against you.
7:24Udi Ledergor:What is that line? I don't know that I can draw that line firmly. And if it makes you feel any better, I know you have this Starburst shaped logo. Our logo was always based on a Starburst as well. So you're actually in good company. If you look up the Gong logo evolution, we started with a very ugly blue and white Starburst that someone in the company had to put together in an hour because we were going to our first event and we needed something to print on the booth. A few years later, that evolved into a slightly prettier starburst with the pink, purple, and white. And in our most recent brand update, we further kind of tamed that starburst into now a kind of funky open G letter that still retains that starburst shape.
8:10And you know what? my CEO's initial brief for the logo was. He said, I want it to stand out in a sea of logos. So imagine you're sponsoring an event along with 200 other companies and you kind of quickly scan their logos because they're all listed together. So most logos are going to be either square or rectangle and they're going to kind of neatly fit into that shape. But a Starburst does not neatly fit in that shape. So your eyes are automatically drawn to it. So I think you should be proud of the starburst. You can continue refining it and testing it. But the fact that it's different and calls out attention is really a good thing, especially if you're trying to punch above your weight and look bigger than you are and get attention while you're building that brand.
8:53Back to your question of how do you know where that line is? I think a lot of it starts with understanding your audience, right? You need to understand your audience. And you can, of course, to focus groups. If you want to be very thorough, you can do surveys if you want more quantifiable feedback. But the point is to understand what would appeal to them, but on the edge of that perimeter of what would appeal to them. If you land somewhere smack in the middle, you're going to be doing what everyone else is doing, which people love calling best practices. And the reason I'm using air quotes is that by the time anyone, anything becomes a best practice, it is in fact a boring practice because everyone is doing it and there's no way to stand out by doing what everyone else is doing.
9:35You're going to get ordinary results at best. If you want extraordinary results, you have to do something different from what everyone's doing. So you do have to dance around and walk that line at the edge of the envelope of what would be acceptable to your customers. Let me give you maybe a quick example, not from branding, but from, well, Actually, I'll give you one from branding because I was laughing when you mentioned the response you got from someone telling you it's a terrible name. I got a similar response when we launched our brand. I already mentioned we had a drooling bulldog, Bruno, who still exists in a few places on the brand.
10:14And we put him on the login page, too. And my chief product officer forwarded to me a message from an actual enterprise customer who asked, and I'm going to bleep out the F word. why the F is there a bulldog on my login screen? This was a real message from an enterprise customer. And I laughed. I'm like, okay, we know we're not for everyone, but I think most people are going to get a good laugh out of this and they're going to enjoy what they're seeing. By the way, if you open your Amazon app and you search for something that doesn't exist, you'll get a bull, you'll get a dog. They actually rotate several dog images.
10:48I've played around with this. There'll be like a sad dog and they'll say, oh, we couldn't find what you were looking for. So people react to, especially dogs, right? Man's best friend. Lots of people love dogs. And so you don't have to be for everyone. And it's okay to occasionally get a negative response. But the other example I wanted to give is from the world of content marketing. So a few years ago, we famously published a piece about how salespeople who swear and curse on their sales calls have an 8 % higher win rate than people who don't. and you can imagine that people had a field day on social when when this came out because we got about two-thirds of the many many responses were leaning in and endorsing and saying things like yeah that's the shit i've been talking about and look rebecca that's what we were arguing about let me do what i've been doing you can see that this is helping me sell sell more and then the other third were appalled that we would suggest using such language in a professional setting and this is a marketer's dream.
11:49Now, why did it go viral? Because it created a conversation. It created a heated debate, a very colorful one because of the vocabulary and subject matter. But you can see what I mean when I say this is the marketer's dream that some people love it, some people hate it and you let them argue over it. The worst thing that can happen is that it's so agreeable that there's nothing left to say and all you get is indifference because nobody wants to engage in a conversation about it. We are entering a new era of outbound. Four years in, we have a meeting that has levelled up our entire offer. That's why multi-billion pound brands trust us.
12:27Udi Ledergor:And we've put meetings with Netflix, Spotify, Facebook, even Barcelona Football Club. We've helped close deals up to 950 ,000. We're doing it all. Phone, LinkedIn, email, direct mail. And there's a few weird and wonderful possibilities that we're keeping in our back pocket. So if you're struggling to get in front of the right people at the right time, inquire today.
12:53Udi Ledergor:So you spoke about polarizing and being controversial at times. I think that I've definitely seen it from B2B marketing and B2C marketing, people being polarizing and controversial for the sake of it and that they've got it wrong. but then I think people struggle like what I guess the question is like what do I give a fuck about or how what do I actually stand for so if you were asking say I'd say I had no idea on how to be controversial or what to stand for so one of the things that we might say is we're a cold calling agency we say cold email sucks it doesn't work is that true no but it's definitely controversial we'll get a conversation going what what the what the kind of talk tracks or thought processes that you would guide a marketer through to find out what they stand for when it comes to strong opinions that's a great question because you can't stand for everything or you really don't stand for anything and you're just like you can't be for everyone or you're really for no one um i think it's a great exercise to go through what are the two or three core domain areas that you want to be known for, right?
14:11Jeff Bezos famously said that your brand is what people say about you when you leave the room. What do you want people to say about you? What do you want to stand for? You have to pick those two or three things, A, because if you don't pick them, someone else will, and you're not necessarily going to like what they pick. So you should probably pick the two or three things you stand for. And just repetition leads to recall and memorizing things. So the more you write about these one or two topics, the more you'll become known for them, right? Very few people are known for 20 different things. You just, nobody has that attention span.
14:45And even if you post every day on one topic, people are probably going to read one-tenth of that. so uh don't don't be in the in the illusion that you can write about 10 different topics and people are going to identify you with these 10 different things if you want to stand for uh cold calling sucks but it works then write about that every every single day or at least a few times a week um and so yeah i don't feel compelled to respond to everything going on in the world uh it is tempting sometimes because sometimes you see a wave of news and uh as surfers know uh it's way easier to ride a wave than try to create one of your own.
15:23And so it is tempting to ride on a wave of news. I think if you can tie it in convincingly to the topic or topics that you care about, then you should do that. And that's a great way of getting attention and recognition. But if it's too far away from what you're doing, I would just let that wave go and catch the next one if it's closer to what I'm trying to talk about. Nice. Could you speak to where we are with ai at the moment are we about to be replaced and running away from terminator or is it overhyped where do you sit um yes we are about to be replaced but probably not by what most people think they're going to be replaced by um people worried about being replaced by ai i think for most of us that's not really founded in reality i think for most of us the real risk is that we will be replaced by people who learn how to use ai in a really strong beneficial way and so the real danger here is staying behind not because ai is about replaces but because people who are harnessing ai learning how to use experimenting with it and creating a competitive edge they are going to replace the ones who don't And so here's how I can think broadly about AI and its uses.
16:48So I'll put it in two different buckets. One bucket is helping us do the things that we're already doing, but do them faster with maybe higher quality, fewer mistakes, and just take away a lot of the grunt work. We're seeing this in sales. There's no reason for anyone to go into their CRM and type the call notes from their last call with their customer. If anyone's still doing that, they're living in the past, right? there are applications like Gong and also others that can do that for you. There's no reason to spend an hour briefing an executive that you're bringing on a call to sponsor an account by typing out everything that happened in the last 200 emails and calls, because there's an app for that.
17:28You hit a button and you get an executive briefing on everything I need to know about this account. Like literally after this recording, I'm jumping onto a call and I just open Gong and ask, what do I need to know as the executive sponsor of this account? And I got all the main points and how I can help and what pitfalls this account might have. And so that's one category of things that AI can already do beautifully for us. The second category is using AI to make us better at the things that we still need to do because a human needs to do them. So an example might be for a salesperson who maybe has 200 activities to do today, which could be a real number, right?
18:06Salespeople are very busy. They have follow-ups on someone who was out of office for maternity leave, and they need to send step number three out of a sequence for outbounding, and they need to send their manager their weekly forecast roll-up and all these things. And they're kind of swamped and they're underwater. Like, what do I do first? What's going to make the most impact? The good news is AI can analyze the impact of all those activities. It knows everything you need to do. and as long as it has the input of all these calls and systems and tasks inside it. And then it can actually guide you on here's everything you need to do today in order of impact or to meet certain deadlines.
18:48If your manager is expecting your forecast roll up by 10 a.m., then I'll remind you to do this at 8 or 9 a.m. And if you promised a customer to send them that case study by Tuesday at 5 p.m., I'll remind you to do that by Tuesday at 5 p.m. And so those are the two big buckets that I'm seeing AI really, really help people with growth and predictability and outcomes that they're looking for. One bucket is everything that AI can offload of you and automate completely, like summarizing calls and drafting your emails and creating your briefs for, let's say, executive sponsors. And then the second is guiding you on the things that we as humans are still uniquely qualified to do.
19:28And I expect that over the years, some things are going to move from one bucket to another as the AI capabilities enhance. You might tell me I'm an absolute idiot for saying this, right? But there's sometimes a feeling that I have that sneaks in. In my whole career, there was something called automation, which feels like it's disappeared and has now been rebranded as AI. So now everything is AI, but it feels like some things are actually automation. is there anything happening where people are going AI is kind of the buzzword and I feel like we can sort of take this automation tool and call it AI or am I imagining that?
20:06No, I don't think you're imagining it and we're seeing a lot of rebranding sometimes a little bit prematurely of things that yeah, they existed three years ago back when we called them automation I literally wrote a post about that recently and I'm not sure if you saw it or were inspired by it but I literally used those words back when we called it automation still did the same thing. So I agree with you. But here's the difference. And there are, of course, real native AI tools that are doing things that were not possible three years ago. And where the difference is, if you remember, I had to build all the marketing ops at several companies from scratch because I came in as the first marketer and nobody was there to build it for me.
20:45I was pretty bad at it, but I had to do it. So I speak the language. And what automation in the old sense is good for is a predetermined sequence where you want the exact same thing to happen every single time. Like if a new lead comes in, you take this field and you copy it there. Then you send this alert to that SDR, you around Robin. It's exact same sequence every single time. That is automation. And that is still super helpful because sometimes we want the exact same thing to happen. Do you have filters on your email inbox? I do. I want them to do the exact same thing every single time an email that meets the criteria comes in.
21:21So automation is still good. Where AI takes you to the next level is that it starts using logical reasoning and probabilities to determine what the next best action is. So it's not going to do the same thing every time. It's going to give you a different result based on all the circumstances and context that it And that no longer is automation. That is something beyond that. That involves human like reasoning to determine what the next best action is. So you can ask AI, hey, based on the 25 calls and 200 emails in this account, what are the next three things that I should do to increase my likelihood of winning this account?
22:02That is not automation because it's not going to spew out the same answer for every account. It's actually going to read all of that, say, hey, based on all of this, it looks like the CMO has some doubts, especially on enterprise grade security and GDPR. So go talk to her about that. That is not automation. That is AI reasoning.
22:21Udi Ledergor:so if i'm a b2b company and i'm maybe sales director or founder and i've just gone through funding and i've got a chunk of money and i'm running around san francisco and i'm thinking right this is my ai budget i'm going to go and invest this what what should i definitely be avoiding what should i be hesitant towards when it comes to spending money on ai to help with generating leads and making more sales? First, I would argue with the approach of this is my AI budget. What should I go spend it on? You should not have an AI budget. You should have a priority list of problems that you need to solve.
23:00The solution to some of those problems might be in AI. Some of the solutions might actually be in the realm of human intelligence. Maybe you just need a good person with experience in the problem you're trying to solve. I have not seen a solution for demand gen since you mentioned that area that you just plug in an ai and it solves your demand gen problems there are tools that highly equipped people can use to help with their demand gen in the two buckets that i talked about automating some things away and helping guide them and prioritizing the things that they need to do um but i would always start with what is the biggest business impact that i'm trying to create and then looking at what solutions exist and some of them are going to be ai some of them are going to be humans maybe enhanced by ai um but but that's how i would approach it and not hey i've got a million dollars which ai should i go spend it on um because you might need to spend less than that you might need to spend more on that depending on which problems you write right now have in front of you do you know the number
23:57Udi Ledergor:one question that people stop me in the streets and ask me zap thompson are you a fully grown bloke that's only happened three times and all three times it was you asking me no most people are asking me, where do you get your contact data from? And do you know what I tell them? No. I'm going to tell you right now. It's Prospio. P-R-O-S-P-E-O. That's Prospio to you. That's Prospio to me. And do you know why we use Prospio? No, I don't know. Please tell me. I'm going to tell you because they are 98 % better at finding mobile numbers and email addresses than any other data provider. If you want to check it out, there's a link in our bio, and you can use it right now.
24:45Hold on a second. That's P-R-O-S-P-E-O dot I-O forward slash WAM to try it for free.
24:52Udi Ledergor:Forward slash WAM to try it for free. Nice. And then I always think AI is as good as whose hands it falls into, and I think that there's a fear. I definitely feel this of like if I if I use AI and I'm thinking right give me uh cold email subject lines I'm reading them and I'm going that might work but I'd probably tweak that because of psychology or my tweak that because because I've got a gut feel for it but a lot of sales people if they maybe don't have the the gut feel or the knowledge are following it blindly so when we think about this human versus AI thing, what advice would you give, especially to young sales people coming through that might not have the gut or the previous experience?
25:40Udi Ledergor:What can they do? Well, the first thing is to arm yourself with a healthy dose of skepticism and understanding, really understanding what are the capabilities and limitations of the different AI tools that you're using. So here's an example, right? If you're using generic LLM, and we all use them in our day-to-day, ChatGPT, Google Gemini, et cetera, they're trained on a vast amount of human knowledge from Shakespeare plays to Super Bowl commercials. And that's what they're trained on. So if you ask them to come up with, I don't know, a sonnet in the style of William Shakespeare, they'd probably do that pretty well.
26:21Here's what they're not trained on. They're not trained on your team's sales emails, your product information, your competitive landscape. So I would be very wary before I asked ChatGPT to help me figure out a customer strategy in our space because it doesn't have the context to do that. For that, I would choose a dedicated revenue AI system that has been trained on my product and on my competitive landscape and on what a great sales email looks like. and there's a much higher likelihood of that system coming up with an effective subject line that I could actually trust and not have to second guess.
Read the full transcript
26:58And here's a fun anecdote. I can't mention all of them by name, but pretty much 85 or 90 % of the LLM companies that we all know, and I mentioned some of them, ask them what they use for their revenue teams and they will tell you they use Gong. Because even though they're creating the world's foundational LLM models, they know the limitations of those models. They know that they were not trained on sales materials and on their competitive differentiators and they don't tie together all the workflows that their sales team needs. So they use Gong. Some of them who've said this on stage, so I can mention are Anthropic amongst others.
27:33OpenAI is speaking at our upcoming event. Like all these companies are using Gong for their revenue teams. And so that tells you something. If you're saying, well, why can't I just use ChatGPT? well, if the creator of ChatGPT is not using ChatGPT to run the revenue team, maybe you shouldn't be using it either. Wow. What a massive thing to be able to say. Like, there's a weakness here that we help with. That's huge. I just want to round off the AI conversation, right? The bit that I think is interesting, and we could potentially talk for hours about this, is AI seems to do really well at this kind of finite puzzle piece, right?
28:15So I could say one plus one and be confident it's going to give me an answer because the variables are there, right? Actually, I would not use it for math. If you've seen a lot of those hilarious experiments, a lot of them are not good at math. So I'm not sure it would get one plus one right. But the interesting thing, right? Me and Jack are big believers in a good sales call and a good discovery call should always be like a therapy session. That's kind of our belief. When you have a debate with ChatGBT or Claude or whatever it may be, it believes that it's been coded to kind of human values, right?
28:48So it might say a human value I've been coded to is honesty, okay? So then I could pose a question to it and say, okay, I'm an alcoholic. Where's the nearest place I can buy a beer? And it will just panic. It's like, I have no idea how to answer that question. Now, if we then look at that from a sales setting, if I say to you on a sales call, Udi, the price, and you go and just jot something down, it's not going to surely be able to pick up on the nuance there. And I wonder if we're outsourcing elements of critical thinking to our next generation of salespeople, are we potentially going to hit a point where we've actually lost lots of skill sets by automating and outsourcing things to AI?
29:35Is that something that you think about at all? Oh, yes, 100%. And we are losing skills. And I think when done right, that is a good thing. um you know anyone who's been in coding my dad was programming in the 60s 1960s and uh he had to write in like hardware language like COBOL and other very low level languages to tell the hardware switches what to do um most modern programmers have no idea how to approach that and that's a good thing because we've built so many abstraction layers above that that they can deal with much higher order issues and create much more impactful software in a very short amount of time.
30:17And so here's an example from our own life. When I was just beginning to drive some whatever, 35 years ago or so, I kept an Atheza maps in my car to figure out how to get to where I needed to go. And I had to plan each drive. If I were going somewhere new, I'd open up the maps and I would create post-its with like, oh, take a second right on the stoplight and then take a left and go around the roundabout. Nobody has to do that anymore because now we have all of us use GPS with map guidance like Waze or Google Maps. And of course, living here in San Francisco where I do, I often take self-driving cars where I don't even have to put the GPS on because a car is going to take me there.
31:02So I don't even need to follow the instructions. And we're seeing the same thing happen in sales. I don't think anyone's arguing that we're going to miss some of these things that we've lost. Like nobody will have to learn how to drive a manual gear car again because you just don't need that skill anymore. So are we losing a skill? Yes. Is it freeing room in our minds and time in our day to do higher order things? I think so. But it's about making that change in a sequence that makes sense and making sure that you don't drop important skills while you still need them. So you talked about salespeople losing the ability to speak confidently about pricing.
31:43Yeah, we should absolutely still teach them how to do that. And I think AI is very helpful at that because AI can reverse engineer the patterns of, let's say we have 400 salespeople or something like that at Gong. we can see which ones are having the best pricing conversations that lead them to the highest deals with the highest win rates. Reverse engineer that and see, oh, these are the six patterns that are best for you to talk about pricing. So I don't need to teach you 20 approaches to talk about pricing. Let's just focus on the six that actually seem to work. Beautiful. Okay. Let's switch gear.
32:16Let's talk about building teams. Our book is out now. Sales is therapy is available everywhere for people who are looking to get better at communicating, asking better questions, closing more deals and bringing in more clients. Beware it is not for the faint of heart or for closed minded people. You can buy it in all good shops. Links below. I'd be really interested to hear what you think people do wrong when it comes to do wrong, what people get wrong when it comes to building effective teams. Yeah, that's a fascinating topic that I really enjoy diving into in the 18 months that I was writing my book, Courageous Marketing.
33:01It's not something that I talked about a lot before because I didn't have good answers. People used to ask me, well, I love all this creative work that Gong has been doing on their brand and their category and their content, their events. But how do I get my team to think like that? And I never really had a good answer. I thought it was some magical coincidence of me finding these people who have this in them and they just produce their best work on the fly. But when I sat down to read the book, I really wanted a chapter to break down and reverse engineer how to create a courageous team, how to find and train and lead these people.
33:39And so I went really deep on this and I talked to over a dozen people. Half of them were team members at different points in time. My first hire, my 10th hire, my 50th hire on Gong's team. And I also talked to other CMOs who built some teams who've done incredible work. So leaders of companies that appreciate their brand and content work. And I wanted to understand what they did to make it work. And as I was analyzing what I got from all these people, I also happened to be reading Adam Grant's book, Think Again, where he covers what makes successful teams at NASA and other high-performing organizations do their best work.
34:20And suddenly things started clicking together. And I found the professional language to describe what my team was doing and how we had created that. So here's the spoiler, and you can go read all about that in chapter 10 of the book, Courageous Marketing. Turns out that if you want a team that is not afraid to take experiments, to make experiments and be risky and be edgy, you need to create a culture that Adam Grant calls psychological safety. Now, we've heard that term before. What it means in the context of this work is that the team members feel that they can fail safely. It means that they don't feel that everything that they do that they get wrong is risking their job, life, or limb.
35:07That is not the case. They feel that they can take risks because if something works out, they'll be commended for it. If it doesn't work out, they can use that as a learning, and that will be appreciated almost as much as an experiment that actually worked out. So obviously, you've got to put some guardrails because you don't want people going haywire and bringing the company down. and that's pretty easy to do. But if you can create that culture of psychological safety where people are encouraged to take risks and run experiments and you encourage them to do that and you publicly praise them for doing that, even if it didn't work out and say, hey, Bob just ran this experiment.
35:49This is the result he got. It wasn't what we were hoping for, but here's what we learned from it. And I can't wait to see the next iteration that Bob's going to take and the next experiment that he's going to run. That's going to open people's mind up to, oh, they actually encourage that behavior. I can bring a bit more creative juices to work and try stuff. Now, the problem is you ask why don't most organizations make this work? Because most organizations have a very conservative, restricted culture where everything you do is pretty much expected to work. and you don't get encouraged to take risks and run experiments.
36:26And when something goes wrong, you see that person being reprimanded. So guess what happens? Nobody else is going to take another risk. Nobody is going to try anything risky that they think there's a big probability of it not working because they see how the organization responds. So if you do recognize and award and encourage people taking risks, you're going to get more of that. And then the last piece that is important to tack onto that, that Adam Grant also talks about in Think Again, and I've seen this work in practice, it's one really important piece of the puzzle is to encourage that psychological safety, to create that psychological safety so people can take risks.
37:05But the opposite side of it or the complementary side of that is that you don't want people going in all directions that won't necessarily lead to the business results. You don't want them just running experiments for the sake of running experiments and to guide them towards the North Star, whether it's creating pipeline on the marketing team or closing more deals on the sales team or improving your NPS on the product team. You have what Adam calls process accountability. And that's just a fancy way of saying, like, we understand what business goals we are driving to. At least that's my interpretation in the world of business.
37:41And so if everyone understands that they have the liberties and the freedom to fail safely, they can run the experiments. And if they have the process accountability to know which business goals that's meant to be driving to, then you know that in most cases they're going to be rowing in the right direction. And that's how it turns out I created a very courageous team that did their absolute best work during their time on Gong's marketing team. And this is all based on their stories and testimonies, which there are many of in the book. And other CMOs confirmed that when they did the same things, and of course you have to be in an organization that ideally encourages that from the top down.
38:21It's very hard to create that bubble of boldness in a very conservative organization. It's not always possible. But if you are fortunate enough to either have the impact on the broader organization or go into an organization that already has that culture, then your team can do absolute magic by creating that psychological safety.
38:40Udi Ledergor:So when you said experiments the first time, I imagined an SDR at their desk pissing around with a Bunsen burner and a couple of test tubes. I imagine that's not what you actually meant. Could you give us some examples of things that maybe you've seen at your time in Gong of experiments that have worked and maybe some experiments that have been courageous and risk taking, but maybe haven't worked? Sure. So here's a fun one. Most marketers know that we have kind of a playbook for inviting people to an event or a webinar. we send out a well-designed email with some speaker headshots and then there's a button to register or RSVP here and then people go to this long form and they're asked about everything from their name and title to their mother's shoe size and they have to fill out all these fields and why do we do that because it makes job easier for marketing ops and the events team because they can easily collect all this information from anyone who confers right So that's why we do it.
39:40Not because it's the best experience for the invitee, but it's the best experience for marketing ops. So we decided to do an experiment. One of my team members, Danny, at the time, he said, well, what if we made this just a more human experience? I'll send out a plain text email, not from the marketing team, but from Danny. And there will be no graphics and screenshots. So just like a simple text or plain text email, you would send a friend. and I won't send them to any forms to fill out. We won't even build the form. We won't even build the website. We'll just say, hey, Jack, I noticed you attended our event last year.
40:17I wanted you to be the first to know that our new event is coming up. Our next event is coming up in October. Just reply to this email, yes, and I will handle your registration and send you the rest of the details when they're available. And so we sent that email out to a few thousand people that attended the last event. within a couple of hours we had 700 registrants to our next event 700 why because we made it super easy for them the email was short and plain text and personal from a name they probably recognized it could read easily on their mobile because it was plain text with no banners to zoom and scroll around and guess what they didn't have to click through and fill out a form they just had to reply yes, which takes like two clicks of my thumb.
41:02And so 700 of them replied yes. And Danny signed them up for the event. And Danny had to work for hours to go and do all that because we have no fancy automation built for that. We just said, let's do an experiment. It's not going to be scalable. So if we find out this works, we'll tweak our process and build automation on the backend. But we had a really solid hypothesis that by making the whole registration process as easy and more human to our invitees, more of them would sign up and they did. And so for years that became the playbook and that's how we send out invites to events. So that's a fun example of something that worked really well.
41:39Udi Ledergor:Udi, I've absolutely loved this conversation. I feel like I could sit and pick your brains all day. Obviously you're a brilliant leader. We always end our podcast the same way, but people that have listened to this conversation, I guess, what's one question that you would leave them with that they should ask themselves. What's one way you can break away from best practices, in reality, boring practices, and transition to courageous marketing? And it doesn't have to be something as big as designing your category. Like think of something tactical, like the next email invite that you send for your webinar or event.
42:18What can you do that's radically different from what you've tried so far that might surprise you with its results? In the book, I give examples of things like a boring email, like a privacy policy update, which we all need to send out. And most of us never give it a second thought. I share in the book how we made it such an exciting email that people screenshotted and shared it on Twitter and LinkedIn and wrote blog posts about it. What can you do to break away from boring practices and be more courageous and practice courageous marketing? And if you model that and if you ask your team to do that, you'll be surprised with the results.
42:54I guarantee that.
42:55Udi Ledergor:You've already given me loads of ideas for the next event we're throwing. So thank you so, so much. If people want to find you, check you out, buy your book, where can they get you? I am on LinkedIn. I'm afraid I've hit my maximum number of contacts so you can follow me on LinkedIn, but I can't accept any more contacts until LinkedIn opens up that limitation of I think 30 ,000 or whatever that number is. And of course, anywhere books are sold, Amazon, Barnes and Noble, wherever you buy your books, go look for Courageous Marketing. It's been a bestseller in like a dozen categories and lots of people are getting inspired on how to take the boring out of B2B.
43:31And if you do get the book, I'd love to hear your take on it.
43:35Udi Ledergor:Amazing. Thank you so, so much. Thank you. Thank you, guys.
From the publisher
Salespeople who swear on their calls close 8% more deals. Marketing teams using pink and purple instead of "Series A Blues" get more attention. Companies that avoid pissing anyone off end up exciting no one.
In this episode, we sit down with Udi Ledergor, Chief Evangelist and former CMO at Gong, to unpack the psychology behind courageous marketing, the real impact of AI on sales teams, and why being different beats being better every single time.
Udi reveals how Gong built one of the most recognizable brands in B2B by rejecting best practices, embracing controversy, and creating a culture where teams feel safe to fail. From the drooling bulldog mascot that made enterprise customers angry, to the viral research on swearing in sales calls, to the plain-text email that generated 700 event registrations in hours—this is a masterclass in standing out in a sea of sameness.
We also dive deep into AI: what it can actually do right now, what it can't, and why the creators of ChatGPT don't use ChatGPT to run their revenue teams. Spoiler: AI isn't coming for your job. But salespeople who know how to use AI are coming for the jobs of those who don't.
What You'll Learn:
Why swearing on sales calls increases win rates by 8%
The danger of "best practices" and why boring is the biggest risk in B2B marketing
How to build a brand that polarizes—without crossing the line
The two buckets of AI: what it can automate vs. what it can guide you on
Why OpenAI and Anthropic use Gong to run their revenue teams (and what that tells you about generic LLMs)
The plain-text email experiment that got 700 event sign-ups in hours
How to create psychological safety on your team so they take risks and do their best work
Why indifference is worse than hate when it comes to your messaging
From privacy policy emails that went viral, to bulldogs on login screens, to the Starburst logo that refused to fit neatly into a square, this episode will change how you think about marketing, sales, and standing out in 2026.
If your brand feels invisible, your messaging feels safe, or your team feels stuck playing by the rules everyone else is playing by, this conversation will give you permission to break free.
Sponsored by Prospeo, the easiest way to find verified emails and contact data for outbound and lead generation. 98% more effective at finding mobile numbers and email addresses. Try it free at prospeo.io/wham
About the Guest:
Udi Ledergor is Chief Evangelist and former CMO at Gong, and author of the bestselling book Courageous Marketing: How to Take the Boring Out of B2B. He's known for building bold, unconventional marketing teams and helping sales leaders understand how AI is transforming their world.
Find Udi on LinkedIn and grab his book wherever books are sold.
Chapters:
00:00 Salespeople Who Swear Close 8% More Deals: The Research That Went Viral
02:15 Who Is Udi Ledergor: From Gong CMO to Chief Evangelist
04:30 Courageous Marketing: Why Different Beats Better Every Time
08:12 The Series A Blues Problem: How Gong Chose Pink and Purple
11:45 The Drooling Bulldog: When Enterprise Customers Hated the Brand
15:20 How to Be Polarizing Without Crossing the Line
19:03 The Plain-Text Email That Got 700 Event Registrations in Hours
23:47 AI vs Automation: What's Actually New and What's Just Rebranded
28:34 The Two Buckets of AI: Automation and Guidance
32:19 Why OpenAI Uses Gong to Run Their Revenue Team
36:55 Are We Losing Critical Thinking by Outsourcing to AI?
41:28 Building Courageous Teams: Psychological Safety and Process Accountability
47:12 The Privacy Policy Email That Went Viral on Twitter
50:45 One Question to Ask Yourself: How Can You Break Away From Boring Practices?
#CourageousMarketing #UdiLedergor #Gong #SalesPsychology #AIinSales #B2BMarketing #WeHaveAMeeting
