A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Sales Pitch)

April Dunford: 40 to 60% of B2B purchase processes end in no decision. If you scratch on that data, the majority of those aren’t saying, “Well, I’m not making a decision to buy something new because the old thing we were doing is better.” That’s not true at all. In fact, the majority of those is they couldn’t figure out how to make a choice confidently. So what they did was they just went to their boss and said, “You know what? Now’s not a good time. Let’s not do it now. Let’s do it next year. Let’s just delay it.” Because that is the safe risk-free thing for that person who’s on the hook to make the decision to do.

Introducing the Guest

Lenny: Today. My guest is April Dunford. April is the world’s foremost authority on product positioning. She’s the author of the bestselling book, Obviously Awesome, which is my favorite book on positioning. And this is her second time on the podcast because she just published a new book called Sales Pitch, which builds on her 25-year career as VP of marketing and advisor to companies like Google and Epic Games and many others. The book guides you through a better way to pitch and sell your product. And in our conversation, April shares the framework that she has seen work most often in getting potential customers to get excited about your product and to decide to buy your product.

Like I say, at the top of this episode, you’ll become better at pitching and selling your product by the end of this episode. And if that’s useful to you, which it should be, this episode is for you. With that, I bring you April Dunford after a short word from our sponsors.

Speaker 1 (00:01:32):

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April, thank you so much for being here. Welcome back to the podcast.

April Dunford: So great to be back. We were talking about this earlier, but it feels like it was so long ago when I did the last one. I was one of the first guests and I feel like, man, you’ve been running this thing forever. And that was like a year ago.

Opening Chitchat and Banter

Lenny: It feels like a lifetime, but it was about a year ago.

April Dunford: But what you’ve done with it is amazing, right? The growth in it, everything else, it’s super inspirational.

Starting With a Real Example

Lenny: Thanks April. I appreciate that.

Positioning and the Sales Pitch

April Dunford: You’re welcome. It’s true though. I think everybody looks at your stuff and goes, “What the heck? How does he do it?”

Lenny: The secret is a lot of work.

Pitching Around Differentiated Value

April Dunford: Yes.

The Pitch Framework Summary

Lenny: That’s the get rich quick scheme there.

April Dunford: Nobody wants to hear that.

Closing Steps for Sales Pitches

Lenny: Yeah. But it’s work that’s extremely fulfilling and we get to chat again and you are a very rare return guest, which makes me very happy. And the reason you’re back is you’ve written an incredible new book, which I have right here if you’re on YouTube called Sales Pitch.

Walking Away from Bad Fits

April Dunford: That’s so cool.

Discovery as the Setup

Lenny: There it is. And it’s in your background, too. It’s like a inception. The book is called Sales Pitch, How to Craft a Story to Stand Out and Win. And we’re going to be spending our time today digging into all of the lessons and frameworks in the book as much as we can in the hour that we have. And my goal for this conversation is for listeners to leave this podcast with better skills at pitching and selling their product. Which I think every product leader and founder will want to do and get better at. How does that sound?

Shifting From Presenter to Educator

April Dunford: That sounds great.

Lenny: Okay, sweet. I was thinking as a way to get into the conversation, we start with maybe a story or an example of a company that you worked with where you applied the frameworks and lessons they teach in the book. And then use that as kind of a jumping off point for digging in further.

Buyer Confusion and Information Overload

April Dunford: Yeah, sure. So my background is, I do positioning work. And so in the work that I do with clients, generally what we’re working on is a shift in the positioning, which is a little bit of a shift in our thinking around, how do we win in the market? So in order to test that positioning, what we want to do is take the positioning and translate it into a sales pitch and then test it live with prospects.

And one of the things I noticed right at the beginning of doing this work is that everybody’s sales pitch kind of looked the same and they weren’t all that great. And for the most part what was happening in the sales pitch is there was no positioning going on in the sales pitch at all. The sales pitch was essentially a product exposition, so essentially a glorified product box room. If there was five dropdown menus, we’re going to click on all five dropdown menus and show everybody everything just feature, feature, feature, feature, feature.

And so, most of the teams weren’t used to doing any kind of pitching in the pitch really. It was just the facts Jack, were just going to show you that. Some would do this really lightweight thing. Here’s the problem, we’re the solution. Now let me walk you through all the dropdown menus, but it is basically the same thing like that.

And so what I wanted to do was build a pitch structure that would reflect the positioning. And so in order to do that, we have to get a little bit into storytelling mode. Not a lot, but at least a little. And when we’re talking about features, we shouldn’t be talking about features. We should be talking about the value that the features deliver.

So let me give you an example and I’ll do before and after what this would look like. So I work with these folks, Help Scout, and so they’re in the customer service space, so think Zendesk or whatever. They’re in that space. And what’s interesting about them is they were built from the ground up to serve digital businesses. So businesses that don’t have a physical store, they don’t have sales reps. And so their approach to customer service was different from the outset. Help Scout said, “Well, you know what? Customer service for that kind of business is really important. It’s the only time you ever get to interact with actual customers.” And so the data shows that if you give them a really great interaction in service, it improves loyalty, it improves repeat purchases, and it’s actually a growth driver. Now, most folks in other industries see customer service as a cost center.

So your telephone company for example, wants to get you off the phone as fast as possible. And they want to push you to the self-serve FAQ channels, and they don’t care about giving you a good service at all. They don’t care about any of that. And so they’re all about driving the cost down. So if we look at Help Scout in their positioning, the alternatives to Help Scout are a handful of things. Most folks start using a shared inbox and it’s really easy to use and the reps love it. It’s easy to use. The problem is, is you start growing and then you want customer service features. You want to be able to do assignments and prioritization and things like that. So then these customers end up upgrading to help desk software and now they’re in this whole different world.

So the first thing is really hard to use. So we’re not in shared inbox territory anymore. And the second thing is that there’s this attitude of we’re trying to push folks to low cost channels. We don’t really care about them. We’re going to assign you a ticket number. You’re not a person anymore. All this stuff. So that’s the situation. So Help Scout, if they did a typical pitch the way I see most SaaS companies pitch, they would just expose the features. Right? So the pitch would look like this. Digital business comes in and they say, “Hi, Help Scout, let me show you how to log in, let me show you all the features. Look, there’s a shared inbox thing there that’s really great. Oh, look, we can do assignments and prioritization and we can do this other thing and we can do this other thing and la, la la.” And I keep going until the time runs out and I don’t have any more features to talk about.

The problem with that pitch is the customer’s sitting there going, “I don’t know, man, that sounds a little bit like my shared inbox, but it also sounds like help desk software. Is it different than help desk software? I’m not so sure. And there’s overlap in the features there.” And so it doesn’t really answer the question, why pick us over the other guys?

And so a different style of pitch would be one, we would do a little bit of setup to give everybody an idea about how we fit amongst all the other solutions and what our point of view is in the market. And then when we get to exploring the features, we would do that within the context of the differentiated value. So here’s how that pitch would look like. Customer comes in and Help Scout says, “Hey, digital business, we work with a lot of companies like you, and I’m going to show you the product. But before we get there, one of the things we think is interesting is that digital businesses look at customer service differently. They look at it as a growth driver rather than a cost center. And so most of the folks we work with see delivering a really amazing experience as a key part of customer service. Would you agree with that?”

Yeah, we would. They have a little conversation and then they say, “Great. We you have choices here. So most of the folks we work with start with a shared inbox, and that’s great because it’s really easy, really easy to use all that stuff. The problem is if you’re growing and you probably are, then you’re going to outgrow that because you’re going to need prioritizations assignments, help desk stuff.

And so then your option is to go to help desk software. And so help desk software is great, does all the things. The problem is that it was not designed for businesses like you. It was designed for businesses that want to take the cost out of customer service. So it’s going to do some things that are weird. It’s going assign your customers a ticket number and it’s going to try to drive them to low cost channels. So can we agree that in a perfect world for digital business like yours, we’d want something as easy to use as a help desk, but had all the bells and whistles so we wouldn’t have to migrate to something else. And on top of that was built from the ground up to deliver amazing customer service. Do we agree we want that?”

Now, at that point, the customer is either with you or you’re not. But if they are, then we switch to the actual demo part. If we do a demo and then we say, “Great, we’ve got those three things. Let me show you how that works. So one as easy to use an inbox. Look, here’s the inbox. It’s easy to use. Looks just like an inbox. It’s amazing. Two, features, so you never have to outgrow it. Look, here’s how we do prioritizations assignments, whatever. We can do all the stuff you need as you grow, and you’re never going to have to switch platforms. And then last one, deliver an amazing experience. Look, the customer gets to choose which channel that they interact with you with. And look, they get to stay Dave and not ticket number 1479.”

That sort of thing. So that’s how the pitch looks in the after. But that’s a really different pitch. That pitch is designed to answer the question, “Why pick us over the other folks?” And so as you might imagine, it is a lot more effective at actually getting clients to get their head around, what is this thing? Why is it different? Why should I pick you? And it just works way better in a sales situation.

Lenny: Awesome. So just to maybe summarize the framework ‘cause you went through each of these pieces, and I think it might be helpful to give people the kind of steps. And I have them here, but maybe it might be better for you to kind work through.

Helping Buyers Understand the Market

April Dunford: So you can think of it is… So first of all, the pitch structure has two big pieces. So the first is the setup. The setup piece is not about us, it’s about the market, our point of view on the market. The second bit is all about our differentiated value. So why pick us over the other guys? So those pieces aren’t equal. In a normal sales pitch situation, we don’t want to spend all day in the setup part. We want to get to the meat, which is our differentiated value, but we can’t skip that bit. So if I’ve got a half hour call or a 45-minute call, maybe I spend a few minutes on this upfront, this upfront stuff is really important though.

And we could break the upfront into three pieces. So it starts with our insight into the market. So you can think of this as our point of view on the market or kind of like the problem inside the problem, in some ways. So in Help Scout’s case, the insight is, ” Hey, customer service is just different for digital businesses, and this is really a growth driver, not a cost center. So we need to think about customer service in a different way.” That’s their insight. So we start with that.

The second piece is pluses and minuses of alternative solutions. What we want to do is paint a picture of the entire market and talk about what’s good and bad of the other ways of approaching the job. And then out of that conversation, we have a conclusion, which is what I call perfect world. But just kind of like can we agree that if we really wanted to solve this problem and knowing what works and doesn’t work in the alternate solutions, can we agree really good solutions should tick these boxes? This is getting the customer aligned with your worldview.

If they’re aligned, then we switch to the follow through. The follow through has a handful of steps, but the main step is this differentiated value step. So usually what we’d start with is an introduction. “Hey, we’re Help Scout. We do customer service stuff specifically for digital businesses.” And then we would move on to, “Here’s the value we deliver. Here’s how we do it. Here’s the value we deliver. Here’s how we do it. Here’s the value we deliver. Here’s how we do it.”

We generally end the sales pitch with a couple of little steps. So one is after we talk about the value, generally there’s a step for proof, which is how can we prove that we do what we say we could do. Which is often a customer case study or it might be independent third party verification on stuff. But usually there’s a proof step. There’s an optional step after that, which is handling objections that haven’t come up during the call. So sometimes we’ll have a silent objection, “Yeah, that sounds really good, but it sounds really hard to adopt.” Or, “Yeah, that sounds really good, but it’s probably pretty expensive.” Or, “Yeah, that’s okay, but it probably doesn’t meet our needs for security or whatever.”

And so we handle that at the end in this special objection step. And then we end the pitch with what I call the ask, which is whatever we want the customer to do next. So it could be just asking for the sale or it could be, “Hey, we want to do a proof of concept. Who do we need to talk to about that?” Or, “Hey, we’re going to do a project. Who needs to be involved in defining the project?” Whatever the next step is in your sales process. That’s how we end is with dask.

Lenny: Cool. I wanted to actually talk about objections. ‘Cause I imagine going through this, companies often don’t agree with what you’re saying, and I wonder how you handle that. So you’re going in this, do you agree? And yeah, the silent objection is really interesting. I don’t even think about that, where they’re just like, “Yeah, yeah, yeah, we agree.” But they don’t really agree. How would you suggest people handle them being like, “No, I don’t actually see the world that way.” Or the silent objection, which I guess is something you save for the end.

No Decision Is the Biggest Competitor

April Dunford: Typically when we’re starting with insight, our insight into the market, if we’re doing this well, the insight is generally not all that controversial. So you could think of it this way. So it’s kind of the reason you built what you built. So most founders, when you talk to them, they didn’t just come up with the idea out of nowhere. They woke up in the morning and said, “You know what sucks about email, this thing sucks about email. And so I’m going to build this different kind of email that solves that problem.” Or in the case of Help Scout, it’s like, do you know what sucks about customer service? It just wasn’t built for these kinds of businesses.

And so if you’ve got a point of view on the world and you’re talking to a customer that just fundamentally doesn’t agree with that… In the case of a Help Scout, they come in and they say, “No, actually it’s a cost center for us. We’re just trying to get the cost down.” They should disqualify that deal because they can’t serve that customer better than Zendesk does. Zendesk is going to win that deal. But if you’ve done this properly, your insight should resonate for the target account that you’re trying to go after. Now, that doesn’t mean there aren’t going to be other objections, and usually there’s all kinds of other objections. But the objections are more on a level of, if I can get you hooked at the beginning in this setup, then we go to the value, which is just proving I can do what we already agreed we wanted to get done. Then the objections tend to be more like operational stuff. “Yeah, this sounds good, but I don’t know if we can forward it.” Or “This sounds good, but boy, we’re going to have to migrate off the old thing or whatever.”

So mentally they’re kind of sold already, but they’re worried about, “Well, what’s IT going to say? And can I actually get budget about this?” And in B2B, we’ve got this network of people that we’ve got to go get agreement from to move forward on this thing. And so often there’s objections around that. The beginning of the sales pitch thing… One more thing on that is that part of what we’re doing in that setup is what salespeople would call discovery. And so that setup part should not be me talking at you. It should be a conversation between me and the client saying, “Do you agree with this? Is this what you’re seeing? Did you start with a shared inbox? What are you doing right now? Did you ever consider using help desk software? Why yes, why no? Do you have any constraints on what you’re looking at? What have you tried before? What are you looking at trying right now?”

This is part of the discovery that we do in a first substantive sales call that your sales reps would know how to do this. Typically, one of the things we don’t have in the pitch decks that I see in SaaS companies is there’s no good place to do this discovery. So it kind of happens outside of the structure of the pitch. In this pitch structure, there’s a definite spot for discovery. So by the time we get to the end of the setup, we should either be aligned like, “Yep, this looks like a good prospect for us. Yep, we can do something. Yep, they got a problem we can solve. This all looks good.” Or we kind of jointly come to the conclusion, “Hey, this just… Our stuff just ain’t for you, man.” And that’s it.

Buying Software Is Harder Than Selling

Lenny: I mentioned a lot of this comes from doing this enough times. You get to understand where people generally agree, this is a problem. We all know this is our problem. And it’s unlikely that you’re going to have to throw everything out because someone just decides, “No, this isn’t for us.”

I think one of the biggest shift maybe from this framework is that you go into a teaching mindset. It’s not just like, “Here’s our product, it’s going to solve your problem.” It’s more, “Here’s what’s happening broadly. Maybe you don’t have the time to do the research we’ve done. Here’s what we found.” And then that builds trust, I think in you as a company and as a leader, a salesperson. And then they’re like, “Okay, see, they see the world the way we do.” Or, “I’ve just realized something new. I never thought of it that way.” And then, “Okay, cool. How do they think about the solution to this?”

April Dunford: Right. One of the key things to think about in all of this stuff that I think we don’t think about enough as software vendors is that customers will come to us and they’ve done their homework. They’ve Googled around and they’ve looked at stuff, but that doesn’t mean they have perfect understanding of the market. In fact, it’s usually far from it. If we think about it, most of the folks in B2B software, most of the time, your buyer has never purchased software like yours before. This is the first time they’ve done it. And their bosses come to them and said, “Hey, figure this out. Go find us a CRM and look at all the CRMs and figure it out.”

And the buyers looking at it going, “Geez, I don’t know, man. There’s a lot of CRMs out there, and I’m looking at all the things. I’m on G2 Crowd and there’s 24 CRMs in the top right corner. And I’m looking at Gardner Group and I’m looking at this thing and I’m actually doing my research, but I’m overwhelmed. What I don’t have is a clear picture of the market. What are the different approaches to this problem? Forget about products. What are the approaches to the problem? Where do the products fit in those approaches? What’s a good solution for me look like? What should be my purchase criteria?” That’s really hard for buyers to figure out.

And in general, in a sales process, we’re not doing anything to help the buyer figure that out, even though we know it. We eat, sleep and breathe this market. We spend all day looking at competitors and thinking about this stuff and whatever. But we’ve got this idea, “Well, we shouldn’t do this because first of all, we can’t talk about the other guys that we’d be seen as bashing our competition, and that’s bad.” The other thing is, even if we did give our opinion, nobody would trust us because we’re biased. But if you look at the research on this stuff, the research doesn’t support that. The research actually says what B2B software buyers want in a sales interaction is perspectives on the market and help weighing their options. And we don’t do that. We’re just like, “Here’s our stuff. You figure it out, it’s up to you. You figure it out.”

And so as a result, what we get are these buyers come in, they’re overwhelmed with all this information. They come in and they sit in our sales process, and we overwhelm them even more with more features and more information. And what they’re really worried about is, “What if I make a bad choice here? I’ve never done this before and I’m going to have to recommend to my boss. And if I make the wrong suggestion to my boss, maybe my boss thinks I’m stupid. Or maybe I buy something and the whole department hates me because awful to use. Or maybe I pick something and it’s just bad software and then bad things happen for the business, maybe I get fired.”

And so the data on this shows that for B2B, 40 to 60% of B2B purchase processes end in no decision. And then when you look at, if you scratch on that data, the majority of those aren’t saying, “Well, I’m not making a decision to buy something new because the old thing we were doing is better.” That’s not true at all. In fact, the majority of the…

April Dunford: The old thing we were doing is better, that’s not true at all. In fact, the majority of those is they couldn’t figure out how to make a choice confidently. So what they did was they just went to their boss and said, “You know what? Now’s not a good time. Let’s not do it now. Let’s do it next year. Let’s just delay it,” because that is the safe risk-free thing for that person who’s on the hook to make the decision to do.

Using Market Maps for Buyer Decisions

Lenny: I think this is one of the most interesting insights that you share in your book and you also share this in the newsletter post about how buying software you could argue is harder than selling it because people will have learned there’s skills and training for selling, but buying is, as you described, extremely stressful. Basically your job’s on the line if you make a mistake. Is there anything more you can share along those lines just to help reinforce that buying software is extremely hard and stressful and people don’t understand that?

Status Quo Bias: Fear of Deciding

April Dunford: Once you get into that mindset, I think then you look at the situation a lot different. I think we’ve seen the statistics on this that says the buyer is 80% of the way through their buying journey by the time they talk to your sales rep. Yeah, maybe, but they might be 80% of the way to saying, “Nope, I’m not buying nothing.” And in fact that’s true 60% of the time. And so how do we combat that? The way we combat that is not just talking about ourselves, it’s actually about trying to be helpful to that person in this very stressful situation that is trying to figure out how do I make a really good decision.

So what we should be doing is giving them a way to think about the whole market and say, in the case of Help Scout, “Look, there’s shared inbox and then there’s help desk software and then there’s us. And I don’t care who the vendor is, I’m going to put them in one of those buckets.” And so you can just think of it that way. So you don’t need to know every single feature, every single thing. I’m giving you a bigger picture of the whole market and helping you feel good. Well, if you choose this or you choose that, now you know why.

Lenny: I think what’s interesting about this is a lot of startups fail because they can’t convince anyone to switch from the status quo. And I think people always think of that as the current product is good enough and that’s why they’re losing, but I think this adds an additional wrinkle of it’s also the person buying it is just like, “I don’t want to add the stress to even decide and make the choice and put my butt on the line to switch.” And I never thought of it that way.

Why FOMO Makes Things Worse

April Dunford: I think that hurdle is a lot more than you think. So we obviously have to compete with status quo, we can’t ignore status quo, because sometimes status quo just is good enough and so we can’t ignore that. We still lose deals to status quo, but we lose an awful lot of deals to just plain customer indecision, customers being more afraid of screwing up than missing out.

Lenny: So to try to overcome that, to drill into the things you find most powerful, one is help the customer understand the bigger picture and why essentially they’re falling behind, why maybe competition is going to have an advantage because they’re thinking in a different way.

The Don’t Get Fired Mandate

April Dunford: Well, I’ll throw something out about that.

Lenny: Please.

Defaulting to the Market Leader

April Dunford: And I’ve heard people talk about this a lot that one of the things we could do in this situation when a customer is feeling this indecision is to lean into this FOMO and say, “Look, you’re missing out. The competitors are all doing it and you’re not doing it.” And so this is an interesting question. And so I was super excited, Matt Dixon wrote this book called The JOLT Effect, and in that they studied two and a half million sales calls, they recorded on Gong and they studied it with AI, and then they looked at what happened after the sales call, so were these successful or not successful, did a deal happen or whatever. It’s pretty rare that we get a chance to dig into some data like this.

And so what his data showed is if a customer is indecisive, throwing FOMO into the mix makes it worse. So they’re less likely to close the deal if you throw that in. And the idea is that they’re already stressed out and you’re just putting more stress on them by pressuring them, by saying, “Oh, this is happening, bad things are going to…” You’re like, “Bad things will happen if I do something, bad things happen if I don’t do something, what do I do?”

B2B Champions and Objection Handling

Lenny: They just put their head in the sand, right? They’re just like, “Ah, forget it.”?

April Dunford: So they’re just like, “Forget it, I’m doing nothing. Now I’m totally paralyzed.” And so there’s an assumption that companies are very motivated by this FOMO thing, but I think that that is not always true, and if the customer is actually indecisive, throwing in this FOMO thing isn’t going to do it. So what does work in that situation is, one, giving them the tools to make the decision. So that includes paint the picture of the market, teaching them how to buy essentially. So teaching them, look, for customers like you, you just have to worry about these three, four things, and all this other stuff, it doesn’t apply to you. That applies to bigger companies, that applies to whatever, so this idea of teaching a customer how to buy is one way to take that stress down.

And then there’s a whole bunch of other techniques you can use. So one is if it’s a really big deal, we can split it into smaller pieces, we can do things like offer you a money back guarantee, we can do things like sometimes we have services and support that are going to help you if things go bad and this is how we’re going to make sure. So this idea of being able to take risk off the table is a really serious one if we’ve got a customer that is actually paralyzed because of this indecision thing.

Does This Work for Early B2B?

Lenny: That makes a lot of sense, basically it’s like how do we help the buyer cover their ass if they made a mistake, because what you’re saying is that’s the main reason they’re not buying your product.

April Dunford: And this FOMO thing is just not going to do it.

What Product Teams Can Learn

Lenny: That’s so interesting. So I really like this framework. I wrote this down, teaching them how to buy, that is a really simple way of just thinking about this whole process.

What Is Differentiated Value?

April Dunford: Well, it’s funny, I was having this conversation with Bob Moesta, he did Jobs To Be Done.

Lenny: Yeah, I watched that episode.

Real Examples of Differentiated Value

April Dunford: So he’s just the best. And so one of the things I think of is normally when we come at this we’re like, “Well, how can we convince the customer that we do the job that they need to have done?” And obviously we need to do that, but there is this secondary job that the champion of the deal is, and that’s how do I make a decision without getting fired? And so we got to help them accomplish that job, otherwise we don’t get what we want, which is the money.

Validating Your Differentiated Value

Lenny: It’s so interesting. And it’s not even necessarily get fired, it’s even the performance sufferers or they don’t get the promotion, it’s did they do a good job. This makes me think of a process at Airbnb we went through to buy community forum software and I just remember these massive teams of salespeople come to the office and pitching everyone on the software and they just keep pushing you to make what’s the next step here, who do we need to roll in, who needs to buy into it? And it’s just like, “Oh my God, it’s so stressful. I have to keep this thing moving.” And then there’s IT coming in like, “Oh, we got to make sure it integrates with Salesforce.” And you start with I just wanted the best community forum software because we were trying to build something really different and unique and you end up with like, “Okay, it’s fine, just go with the thing that works with Salesforce. It’s all good. I’m just going to move on to another process.”

Honesty and Confidence in Sales

April Dunford: Well, this is the thing, it’s so easy to default to the market leader in that situation. The market leader has this big advantage that you can say, “You know what? Who’s going to get me in trouble for picking Salesforce? Nobody.” It’s so easy to just flip back on that. And so if you’re the challenger in this situation, the brand that’s number two or number three, you’ve got to get over all of this inertia and tilting towards the status quo, because it’s just so easy, it’s the lowest risk decision, besides do nothing is to just pick the leader in the market and we’ll just run with that.

The Bowling Pin Strategy

Lenny: I think the classic phrase was no one gets fired for buying Microsoft. I wonder is it Salesforce now that’s the default version of that now?

April Dunford: Yeah, the original one was IBM. [inaudible 00:30:57]

Back to the Framework: Ideal Solutions

Lenny: I think you’re right. Oh, man.

April Dunford: Now you totally get fired for buying IBM. I don’t know what happens. The other thing you bring up is I think an interesting thing to think about too that really messes people up in these situations is that in B2B, typical purchase process, we have five to seven people involved in making the deal happen and so there’s this complexity we don’t have a consumer, but a lot of people I think overcomplicate that. In a typical B2B purchase process, we’ve got someone in that buying team is what we would call the champion. So that person is the person who’s been tasked with, hey, pick us the accounting software or pick us the CRM, you figure it out. And so that person is the person that does the initial research, makes the short list, probably sits on the first calls, and then there’s all these other people.

Now, the other people can’t make a deal happen, but they can kill it a thousand ways. So the way this works is your positioning and your pitch needs to really work for the champion, because if it doesn’t, you don’t even get to talk to anybody else, you don’t even get to go near anybody else if you don’t make it out of the shortlist and you don’t get the deal cooking. But once the deal is cooking it is on you to arm that champion to handle all the objections potentially of all the other groups. So if you’re the line of business buyer, let’s say you’re in the sales department and you’re buying a CRM, IT is going to have to get involved at some point, and IT doesn’t really care about the value of your CRM, but they do care does it meet the security requirements and does it integrate with the stuff we already have and how much of a pain is this thing going to be to manage, and so we’re not actually pitching value to those people, we’re just handling objections.

And so once we realize that, then we can get really tight on our positioning in our sales pitch. What we’re really trying to do is just cook the champion, get the champion, and then once the deal’s going we got to arm the champion for how to handle all these objections of all these other groups so that you can get a consensus to get a deal moving forward.

Proof, Objections, and Next Steps

Lenny: How do you actually do that? Is it ask them what are all the concerns you’re hearing? Is it ask the individual stakeholders what your biggest concern is?

Revisiting Positioning When Pitches Fail

April Dunford: Well, if we’re really smart, we already know because we’ve done lots of deals. So if we’re being a good partner in this, sometimes even in the very first meeting in that spot where we’re talking about objectives, we’re going to say, “Hey, look, IT is going to come in and they’re going to be worried about this, this, and this, and don’t worry, we got you.”

So we’re SOC 2 compliant, we do this, we do that, we know because we’ve done 15 deals and we know what these deals are like and we know what the stuff is going to be. You might have the champion come in and say, “Well, I don’t know, end users might not like it.” And it’s like, “Okay, well, here’s how we’re going to get your end users on board, this is the training we have, this is the stuff we’re going to do.” The neat thing, if you have a product like [inaudible 00:33:54] on the front end of that, it takes that objection off the table. And you might have other things like you’re going to take this to your boss and they’re going to want to know ROI numbers, blah, blah, blah, and we’ve already done that, look, here’s our calculator, if you give us this information, we can put this in, here’s how you sell your boss.

So that’s what we’re doing. We’re trying to arm them because we’ve done a million deals, they’ve never bought software like this before. So half the time you’ll be doing deals and they don’t even know what the purchase process is. And so if we’re being good partners, we’re like, “Okay, does this need to go to purchasing?” And they’ll say, “Yeah, it probably does.” Oh, well, here’s what typically happens at purchasing. They’re going to do this, this, this, and we’re going to give you this stuff and that’s going to help you get it through purchasing.

Lenny: The way you’re describing it now makes it feel like you need to be a big company for this to be useful because smaller companies don’t have all these reps and they may not have the resources to do all these things you’re describing. Who is this framework useful for? Can you use this approach if you’re just, say, an early stage B2B?

Testing and Rolling Out New Pitches

April Dunford: Well, so it’s B2B products. If you don’t have a sales team, I still think you can use this structure to build a story that marketing can use and you can use in different ways, and we can talk about that. But in the companies that I work with, they’re B2B, they’ve got a sales team, and so the immediate thing we’re doing is we’re making a shift in positioning, we’re building a sales pitch that reflects that positioning, we can immediately implement that in sales even though it’s going to take a while for us to forklift the messaging and do other stuff and change our campaigns and everything else to match this new positioning, but we can tighten up the sales pitch and have an immediate impact over in sales on that. Second thing is that I’ve worked with tons of companies where the founder is the only sales rep and this works pretty good for that.

I don’t think we need a ton of resources to do it, but I do think we need to have enough traction in the market that we understand how a deal typically goes. So if we haven’t sold anything yet then we don’t know yet, it’s hard for us to help you buy something if we don’t even know how to sell it. But if I’ve done 10 deals, I know what happens, I got a pretty good guess of what IT is going to say when you try to implement this stuff, I have a good guess of what’s going to happen when we go to roll it out, I have a pretty good guess of what your boss might object to or might get excited by. And so I don’t necessarily need a research team to go figure this out. This is just me trying to be helpful and help the champion do their job of getting this deal to the finish line.

How Long Does Positioning Take?

Lenny: So maybe the MVP of this approach is a deck that you continue iterating and adjust and restructure, and also bullet points of things you want to bring up like, “Okay, cool, IT is going to ask for these things,” a few bullet points that you keep track of.

April Dunford: Exactly.

The Role of the Marketing Team

Lenny: I’m also thinking from the perspective of a product team building a product, they don’t really sell it themselves. They work with sales, they work with marketing. Is there anything that you would recommend or that you think product teams could learn from this approach of selling that would help them build products in a different way or work with sales in a different way?

April Dunford: Yeah. So here’s what I think, the core of a good sales pitch is really deeply understanding your differentiated value, which is what is the value I can deliver that no other solution can. Often what I see at companies is you got a smart product team and they know a lot about the stuff they’re building and why it’s important and what the value is to the customer, and they did all this work on that when they were building it, but that information never made the jump to sales, because sales isn’t even trying to pitch value. They’re just pitching features like here’s the dropdown menus, here’s what they do. And so the first step in fixing this I think is to have a cross-functional team work on positioning.

So if I’ve got product, marketing, and sales together in the room working on defining what our differentiated value is, then I’m going to get all the good juice out of the product team that deeply understands the product, deeply understand what’s differentiated about it, deeply understands value, and then I’m also going to have all the juice from the sales team that understands what the common objections are, what the champion really wants to get done and doesn’t want to get done, what the situation is in a typical account, and then all of this cool information sharing happens, which actually you end up with way better definition of your differentiated value in the first place.

And so once we’ve done that work, it is very natural then for us to work together on the sales pitch that reflects that. What typically happens is not that at all. What typically happens is product’s working on some stuff, sales is working on some stuff, marketing’s working on some stuff. Marketing in their own little bubble comes up with positioning, they might build some stuff for the sales team, heave it over to the sales team. Sales team looks at it and says, “I don’t get what any of this stuff is. I disagree with this. This doesn’t match what I see,” and they just throw it out and they go back to doing the same pitch they’ve been doing since the year of the flood.

The Real Impact of Positioning Work

Lenny: That’s a long time. So first podcast episode was all around positioning, and so folks want to get deep into that, they should listen to that, so we’re not going to spend tons of time there, but differentiated value is a big part of this process also so I think it’s worth spending a bit of time here. Could you maybe share a couple examples of what this is to give people a sense of what does it mean to share differentiated value?

April Dunford: Yeah. So differentiated value is the answer to the question why pick us over the other alternatives? And so the way we get at that in positioning is we start with putting a stake in the ground of who do we actually compete with? And so if we didn’t exist in the market, what would a customer do? And so typically there’s some status quo thing, it might not even look like you, it might just be a spreadsheet, or do it with the intern or manual labor, and then there’s whatever else ends up on a short list against us. And it’s basically the definition of I got to beat all this plus indecision in order to win a deal, so I can stick my stake in the ground. Sales knows the answer to this question. If you have a sales team, they know the answer to this question, what would a customer do if we didn’t exist, they know.

And then we get to the next step is, well, so what do we have that’s different? And that’s capability wise, feature function of the product or capability of the company, so it could be features, it could be your pricing model, it could be we have support in a way that the other folks don’t. So there’s all kinds of things it could be. It could be be the breadth of the portfolio that you have beyond that one product, we can fill whiteboards with this stuff. And then what we do is we go down that list of features and we say, “So what? You got advanced AI, whatever the heck the thing is, so what? Why does anybody care?” And the answer to that so what is your value. And because it came from this differentiated feature, it’s generally value that the other guys can’t deliver because they don’t have the capabilities that underpin it.

So if I give you an example, a company I worked with a few years back, they’ve recently been acquired by Salesforce called LevelJump, and so they’re in the sales enablement space, which is terrible. There’s a million companies in the sales enablement space and they all look the same. And so LevelJump, so if you look at, well, what’s the competitive alternatives, if I look at all the companies in the sales enablement space, you can put them into two buckets in terms of approaches, they’re either a CMS like a jazzy content repository where you could make sure that people are using the right content and whatever, or they’re an LMS, a learning management system, which I can build the course and certify you on the course, and that’s how we’re going to train the sales reps.

If you look at LevelJump, they’re differentiated capability is they’re the only one that’s built on top of Salesforce. That’s the feature, we’re built on Salesforce, the other folks aren’t. And then who cares? So what? And so when we first had a conversation about it, there was five or six different answers to that so what question, but the big answer was, well, because we’re built on top of Salesforce, my sales enablement data is integrated with my sales data. And then you say, “Well, so what about that?” Well, because then that means I can actually tell did the sales enablement improve time to first deal or improve time to make quota? Well, so what about that? Well, if I improve that ramp time, then we get way more revenue faster. So that’s the differentiated value.

When I go to do that in a sales pitch, I can translate that into my insight. My insight is every day your rep’s not making [inaudible 00:42:36] it costs you money. So if we really want to solve sales enablement, don’t we really want to have something where we can measure whether or not the sales enablement is working with sales metrics? Yeah, we do.

Andy Raskin’s Framework Versus Sales Pitches

Lenny: Interesting. So the differentiated value often informs the insight that you start with?

Writing Tests in Job Interviews

April Dunford: It does. It absolutely is. The insight is basically the context that makes your differentiated value important, what is the thing you need to know to understand the importance of my differentiated value? In the case of Help Scout, the insight is, look, digital businesses like customer service is a growth driver, where does that come from? If you look at their differentiated value, it’s there. And so we can just reverse it, flip it around. Even if the product wasn’t necessarily constructed with that insight, maybe we got there sideways or the roundabout way or whatever, we iterated our way into that. We can look at the differentiated value and then basically reverse it out to the insight.

Products I’ve Liked Recently

Lenny: What’s a sign that the differentiated value or insight that you’ve come up with just isn’t clicking?

April Dunford: If the differentiated value doesn’t work in a sales pitch, what you’ll get is the company going, “Why would I pay for that? This is not value for me, buddy.” The companies I work with, the way I look at it is if you’re in market and you’re selling and you have happy, engaged customers, there’s differentiated value there. That’s why they picked you. That’s why they love you. That’s why they don’t turn out on you. It’s there. You might not know what it is, we might have to do a little process to get at it, but it’s there and it exists.

Lessons Learned From My Father

Lenny: Awesome. Another question that’s been in the back of my mind since we started talking about differentiated values is just how honest should you be about the competition? Obviously there’s a spectrum of extremely honest to super biased, what’s your guidance on just how honest to be there?

April Dunford: The posture I think you should assume in a sales situation, I had an old boss used to talk about this, is the posture we should have is calm confidence. So where that calm confidence comes from is we really understand why people should pick us. So this is differentiated value, we really understand it and we really understand who that’s a really good fit for, and we don’t even bother trying to chase anybody else.

So we should be able to come in and say, “Look, we’re sales enablement that delivers results. If you don’t care about those results, you shouldn’t pick us. You should pick someone else.” And so generally what we’re trying to be is extremely honest. We’re trying to come in and actually give credit where credit is due with the other approaches, because typically the other approaches work just fine for other kinds of companies. If you’re really small and you’re not growing e-commerce business, use a shared inbox. It’s free, it’s easy to use, there’s no problems there, just use it. If you’re really worried about bringing the cost down in a customer service center, maybe you should use Zendesk. And so I think the more we can act as a guide in this situation and come in and say, “Look, these guys are good for this, these folks are good for this, and we’re good for this. And you might not care about that, and if you don’t care about that, we’re not the one for you. You shouldn’t pick us.” But I think that…

We’re not the one for you. You shouldn’t pick us. But I think that this calm confidence idea is that where we know the client should pick us, we should be unafraid to fight for that business. But we should totally walk away from business where we’re not the best fit. We shouldn’t be chasing that business at all.

My Absolute Favorite City

Lenny: And this comes back to teaching them how to buy again and again. For these cases where you’re like, “This is not a fit.” Ideally you know that before you fly to their office and pitch them.

April Dunford: Yeah, generally you’ve had some kind of qualification happen upstream, and so that qualification could be done in lots of different ways. If you’ve got some kind of product like growth motion in the beginning, you’re looking for signals in that. And if the signals aren’t there, then you’re not talking to them. And so if you’ve designed your signals right, then you already know there’s intent there. You already know you’re a fit. You already know stuff. The way a lot of companies do this is they’ll have inside sales do a qualification call before they set up a first call with a sales rep. In that qualification call, you’re trying to make sure is this the right person? Do they have a need that we can actually meet? Is this actually a good fit for what we do? And if they’re not, they don’t even make it to the call.

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Another question around this idea of differentiated value and just alternative approaches is there’s a certain previous guest who was very big on creating a category being extremely important, and that potentially being the only way to build a legendary business. I know you have a different perspective on that because in theory if you go that direction, there’s no alternative. It’s like “We’re the one.” What’s your take on that?

April Dunford: Well, so here’s a few things. So one, obviously creating a category is not the only way to create a legendary business because the vast majority of legendary businesses did not create the categories that they’re in. So Google did not create search, Facebook did not create social network. There’s so many of them. It’s actually more of an exception to the rule that the company is creating a category than the other way around. So I think it’s a bit disingenuous to say the only way. It is a way to build a big business, no question about that. But it’s absolutely not the only way. In fact, it is not the most common way, but it is a way and it does work. So that’s one thing. The second thing is that category creation is interesting. Like most companies, if you look at their arc, even the category creators that are successful, they did not start out as category creators.

So they started out as a niche play in an existing category, and that’s because that’s generally the easiest way to get traction for a company early because what is the job of the market category? The job of a market category is to help answer the question, what is this thing all about? If I’m positioning an existing category, I can say, “Well, I’m CRM for very small businesses.” That was Salesforce’s initial positioning. I didn’t have to explain to you what a CRM was, that already existed. There was already billion dollar company in that space. We know what a CRM is, and I could say “We’re CRM for very small businesses. The reason you can use in this very small businesses is we don’t have any software. So you don’t have to have an IT department to babysit it. It’s fantastic.”

So most companies start there. Now what happens is that if you become the dominant player in that space, which again, category creation folks talk about this like no category creator has ever lost the market. In fact, most category creators wins their market. Like what happened to MySpace? What happened to Ask Jeeves? It didn’t work out so good for them. Most category creators actually get overtaken by fast followers. So if we look at the CRM market, Siebel was the big dominant player there and now they’re not. So now we’ve got Salesforce. Once you’re the dominant player in that market, a cool move to do is to actually extend the boundaries of the category so that you can continue to grow. And most of the category creation examples we see are companies that when they were 200, 300, 400 million revenue dominating their space, then decided to move the goalposts and say, “Well actually now we’re expanding into all these other areas and we’re going to call this category something. And that’s what it is.”

And there’s loads of examples of that. Like Qualtrics for example, is a company that a lot of people talk about very successful category creation. Well, they were survey software up until there were 300 million revenue just like everybody else in an existing category. So that got them there and that worked just fine. Oh, well, once we’re dominating it, now we can say it’s whatever, it is, customer experience software, whatever it is. Snowflake. Another good example like data warehousing in the cloud, they were that data warehousing, an existing market, were data warehousing for the cloud. That is not category creation. And that took them all the way up to the point where they were about to go public and now they’re cloud data, which is their attempt to expand and say, “Well, it’s not just data warehousing, it’s actually data lakes and all other data stuff.”

And so that’s a smart move for them because they’re now very well known in that space. I’m not saying category creation is a bad thing. There are examples of company that came right out of the gate and successfully created a category and then survived to own the category longer term. But a more common thing that happens is that the company does the hard work of creating the category and in exactly the moment where the category starts to take hold, fast follower can come in with fresh funding and a lot of it and learn from all your mistakes and come in and knock you off the peak right when you think you’ve made it.

So I think category creation is, again, it’s good, it works, but I think we have to be very careful when we’re thinking about doing that at an early stage business or a business that isn’t already dominating the category that they’re in. It’s much more common to see companies come in, shave off a piece of the market, dominate that, and then successfully branch out. It’s what Jeffrey Moore called bowling pin strategy. Almost all successful companies follow bowling pin strategy.

Lenny: Wait, what is that? Let’s touch on that real quick.

April Dunford: Oh yeah, you remember that thing. It’s funny how many times I’ve talked about bowling pin strategy in the last two months. So this comes from a bunch of work that was done around the way innovation gets adopted, blah, blah. So there’s a bunch of research done on this stuff, and I’m going to misquote it because Jeffrey Moore stuff, I’ve been reading it for decades. But bowling pin strategy goes like this. The easiest way to take over a great big market is to define a segment of the market that is underserved by the market leader.

And so if you think about a bunch of bowling pins, we’re going to circle around the lead pin, which is this little piece of the market that’s easy for us to go get, and the market leader probably doesn’t care about it. And so we knock over that pin and knocking over that pin enables us to get to the three pins right beside it. And so now I’m established here as a beachhead and I can go get the next three pins, I’m going to knock those over, and eventually I get big enough to challenge the market leader and then I overtake them.

So the example for my early career was I worked at this company, we thought we were enterprise software. We narrowed it down to CRM for investment banks, and so we literally drew bowling pins for our investors and said, “Lead pin is CRM for investment banks. Once we knock that over, then we’re going to go to retail banking, then we’re going to be CRM for banking. And then once we knock that over, we’re going to go to insurance, then we’re going to be CRM for financial services. Once we knock that over, then we’re going to be a great big company and we’re going to challenge Siebel to be CRM for enterprise software.” Instead we got acquired by Siebel for like $1 billion, but whatever. So most companies, if you look at the history of them, they actually start that way. And so yeah, if we just fast forwarded to when they were 300 million, we can say “Category creation’s the only thing to do,” but it’s like, well, what happened before then? That was something different.

Lenny: Awesome. Let’s come back to your framework. I’m looking at the list of bullet points. So we’ve covered a lot of this already actually. So there’s the insight where you helped them understand what’s happening in the world and what’s changing and why this is important. Then you talk about what the alternative approaches might be, pros and cons. Then there’s this third step, which we haven’t talked about yet, which is sharing the perfect world characteristics of a perfect solution. Can you talk a bit about that and why that’s important?

April Dunford: So this is the conclusion of the setup phase. So if I’m Help Scout for example, the conclusion is we say, “Look, you really want customer success software that’s as easy to use as an inbox. You’re never going to outgrow it, but it was built from the ground up to be deliver an amazing service.” And so it’s this part of the pitch where we actually get agreement with the customer that we are aligned in terms of our point of view on the universe. So it’s where I say, “Okay, we’ve had our little discussion about the pros and cons of the other alternatives,” and we say, “So look, so are you with me, man? Can we all agree that a really good solution for you would have A, B and C?” And the customer is either like, “Yeah, right,” or they’re not. And so if they’re right with you on this definition of the perfect world, then I’ve got you. I’ve already won the deal and I haven’t even talked about us yet because the way I’ve set it up, I’m the only one that can deliver that.

So if you say, “Right,” all I got to do is prove that I can do that and get you over the hurdle that it’s possible for you to adopt it.

Lenny: Sounds too easy.

April Dunford: Yeah, I mean…

Lenny: It’s like you lure them in.

April Dunford: If all of this was easy, Lenny we would be on a beach drinking out of a coconut.

Lenny: Oh man, let’s make it happen. Okay, so that’s the setup. What do you call the second part again?

April Dunford: It’s the follow through-

Lenny: The follow through.

April Dunford: … which is really focused on differentiated value. So in the second part, the first step is usually we introduce our stuff, which is where the market category is important. So we come in and we say, “Okay, can we agree that a really good solution should tick these boxes? Yes. Okay, good. Now let’s talk about us. Okay, so we believe that. That’s why we build what we build.”

So here I am, I’m Help Scout, we’re customer service software for digital businesses or whatever our market category is. So we introduce it just to get people straight in their mind about what it is, and then we move to here’s the value, here’s how we do it. If we think about a typical sales call, like let’s say a sales call is half an hour, 45 minutes, I would expect to spend more than half of the time in the sales call in this differentiated value phase. So if we’re doing a demo, that’s the demo, and we’re saying, “Okay, step one, let me show you how we do this. So easy to use as an inbox. Here’s the features. Never have to outgrow it, here’s the features. Delivers amazing customer experience, here’s the features.” And so that’s where we’re getting to the meat of what you thought you were getting when you clicked on the button that said, “Give me a demo.”

So that’s what we’re doing there. And then we end with these three little pieces. One is generally I got to show you some proof that I can do what I say I can do. So if I’m claiming this thing delivers an amazing customer experience, how do I prove that? Well, I can prove it by other customers saying it was amazing. That’s one way to prove it. If I had some independent third party data that proved whatever I was claiming, I could show that there too. But a lot of times what we’re doing is we’re like, “Let me show you how this worked in a company that used our stuff. So this is what the before looked like. They did this thing, here’s the after.” And so customer case study is usually good way to do that, but there’s usually a step called proof, which is, I showed you the value, now here’s the proof that I can actually deliver on that value and it’s not just me blowing smoke.

And then the step after that then is this optional objection step where they say, “Oh yeah, sounds good, but IT is never going to go for it,” or “Sounds good, but maybe it’s going to be too expensive,” or something. And so you’re going to handle that objection as best as you can. And then you finish with the ask, which is whatever the next step in your sales process is. So it’s, “Hey, so what we have to do to get a deal cooking here, do we have to get IT involved? Does IT need to see it? Would you like us to come in and present with you with IT or do you want me to just help you work on some stuff for IT?” It’s whatever your next step in the sales process is.

Lenny: Awesome. So let me read through this just to have it also succinctly here in case people are taking notes or trying to remember the stuff. So there’s the setup, there’s the follow through. Within the setup, you have the insight, the alternative approaches, pros and cons, in the perfect world. And then you introduce your product, talk about the differentiated value, share the proof of why it works, potentially handle objections, silent objections, and then the ask of what comes next.

April Dunford: That’s right. That’s it.

Lenny: In terms of knowing if this is working and if your differentiated value works or if your insight works, do you have kind of a heuristic of a success rate that feels right? How often should this work for you to feel like “I think we have it?”

April Dunford: Well, so generally if the sales pitch isn’t working, it’s because the positioning was weak.

And so companies that jumped straight to building the new sales pitch without going back and really making sure that they really nailed the differentiated value, who knows? Maybe it works, maybe it doesn’t. And a lot of times it doesn’t, I think. And so in the work I do with my clients, we go all the way back to the beginning. So we go right back to let’s work on the positioning first. Now, if I’ve got the smartest people from the company in the room and we’ve done enough deals that we are pretty knowledgeable about how customers buy and what they like and what they don’t know. If I’ve got the senior executive team in the room and they’ve got a reasonable amount of customer experience, we can pretty much feel good that the positioning we come up with if we’re following a process will be good.

Then it’s just a matter of taking that positioning, mapping it to the sales pitch and then going to test it. So I think there’s a bunch of things in testing that are really important. So one is we absolutely need sales involved in building the pitch. If we don’t have sales involved in building the pitch, the pitch is never going to stick. The rule with sales reps is even if they don’t like their current pitch, they’re comfortable with the current pitch and they know it and they’ve memorized it and they have a little joke they tell on slide three. So they’re not going to give up the current pitch without a fight. So you got to get sales management involved in building a new pitch, and then I would never just build the new pitch and then heave it over the wall and say, “Good luck, Chuck.” Because what’ll happen is they’ll come up with all kinds of excuses why they can’t use this pitch.

Instead, what you do is you take your best sales rep, your best one, and you bring your best sales rep over and you train them on the new pitch. They got to learn it, they got to pitch it to you, pitch it to the head of sales. We do a bunch of repetition on that, and then we have that rep test the pitch with qualified prospects. So we don’t go to existing customers. They’ve already been polluted with the old positioning and the old pitch, and this needs to work with a qualified prospect, so let’s do it in the way it was intended. We’re going to take qualified prospects and work that new pitch with them. Usually what we’ll do is a test period where after every pitch we’ll huddle and say, “What worked? What didn’t work? Maybe that word is tripping people up. Maybe we need to move this slide from here to here,” and so we’ll tune it.

And then after we’ve done a bunch of pitches, one of two things happens. And so in this test structure, I am very much relying on the expertise of my best rep to know what’s good. So after the best rep is comfortable with the pitch, done a bunch of pitches, re-twizzled it, at some point the rep will say, “Okay, I think we’re done optimizing this pitch, and I’m not going back to the old pitch. I’m sticking with this pitch because I think this one works better.” An experienced sales rep will know that, whether the pitch is better than the old pitch, if you give them the opportunity to feel comfortable with it, work with it a bit and pitch a bunch of new prospects with it.

So if your best sales rep says, “Oh, this is way better than the old pitch. I can just feel it from the way people react to it and the number of times we’ve been able to convert people over into actual opportunities from a first call.” Then what you do is at that point I call that pass. So then we take that rep, we can film them doing the pitch for training, and then we can take that rep, go back to the rest of the sales team and have that rep sell everybody else on it. So that rep goes back and says, “Listen up people, you’re stupid if you’re using that old pitch, which sucks. This new pitch is way better. Trust me, I’m the best rep on this whole team. By the way here’s the list of deals I have cooking in the pipeline that I got using this deck. You should go do it and I’m going to teach you how to do it.”

Now I got sales, teaching sales, teach and sales instead of marketing, sort of throwing something over the wall and crossing their fingers and saying, “Hey, I hope this works.” What we should see is an immediate uplift in what happens after first call. So most of the time what that is we get a higher percentage of deals converting into opportunities after that first substantive calls. Sometimes depending on the quality of the pipeline we had coming in, we’re actually disqualifying more. But sometimes that’s a good thing.

But what we should see is an immediate uptick. It’s stuff coming into the pipeline. It’s a neat trick to pull, especially right now when everybody’s budgets are really tight and you’re just trying to squeeze more juice out of the lemon. It’s a really easy way to get some more juice out of the pipeline. Just go in, tighten up your positioning, tighten up that sales pitch. And we can have instant impact with that because we can roll that out in a couple of weeks and start getting better deals flowing through the pipeline because these customers are understanding your value better, understanding why to pick you better. It’s just easy, low hanging fruit to do when the economy’s bad.

Lenny: To give people a sense of maybe how easy that might be, how long would you suggest people spend on maybe tweaking their positioning and then also on this pilot, how much total time could it take to potentially significantly increase sales?

April Dunford: So in the customers that I work with, when we do the positioning stuff, the positioning stuff takes a week. We’re beginning and we’re done in a week. We’re all about speed on this thing. We’re trying to get the thing happening fast. So we’re in and out on the positioning in a week. It might take you, it depends on the company, the bigger the company, the slower this is, but some big companies are actually quite fast, and if you’re motivated, it shouldn’t take long for us to take that pitch and make it real.

Then we got to find a rep, train the rep, and then how long it takes us to test it really depends on how much deal flow you’ve got. So if you’re working on monster deals and you don’t actually get that many qualified prospects to pitch, that might take a few weeks. But if you’ve got a lot of prospects coming through the door, and you can get through this fairly quickly. So I’ve had companies do it start to finish. We got new pitch out the door and people using it in two weeks. That’s about as fast as you can get it done. Most folks, I would say take about a month.

Lenny: Cool. That is a very short-

April Dunford: Sometimes you’re like IBM and who knows when you get to it, right? But most folks could get through it if everybody’s motivated, we can get it out and have it running a month.

Lenny: You mentioned marketing and earlier you said that marketing is involved in this process in some way. What’s your advice to just how to involve marketing, where they fit in?

April Dunford: Yeah, so usually marketing is going to end up being the stewards of the positioning once the positioning is done. So they’re going to end up being positioning police after this because a lot of the positioning stuff is going to take the form of marketing things. So they’re invested in this. So when I was the VP marketing, I was the person that would instigate the positioning thing, let’s get everybody together and work on the positioning. And then I would usually be the person that is driving, getting the sales pitch figured out, but it’s me and sales and product working together. And then once the sales pitch is done, depending on the size of the organization and whether or not you have sales enablement or somebody inside sales that can babysit the pitch. Usually me and the head of sales would work on, “Okay, this is the pitch and this is locked down and we’re not actually going to change this pitch until something happens that requires us to change the positioning. And then that’s when we’ll re-look at the pitch.”

So we would look at recertifying the reps every quarter on the pitch and all that kind of stuff. And that would be generally, me in partnership with the head of sales. But it depends on how you do it. I don’t think it really matters who owns it. If you have a good product marketing organization, good product marketing organization generally is very concerned with the positioning and the pitch, and those two things sit in their purview, but depends on how you define it. I can’t wait till you get Airbnb. Tell us how this stuff works. They’re different because they’re a consumer, but companies are arranged in all different ways. So if you have product marketing, it looks one way. If you don’t, it looks another way. Somebody’s got to kind of be the owner of this thing though. And so we have to decide who that’s going to be.

Lenny: Just a couple more questions. One is to motivate people to do this. What kind of impact have you seen at companies that invest this time and rethink the way they pitch?

April Dunford: Well, so people don’t like me to talk about revenue stuff. Hugely what we’ve seen though is again, the immediate impact is felted sales, and everybody’s very jazzed about that.

April Dunford: Impact is felt in sales, and everybody’s very jazzed about that. Because sometimes what the worry is, is we’ve got this old positioning and they came in through the pipeline that way. So they were exposed to our marketing somewhere with this old positioning, and then we hit them with the new positioning with this sales pitch. And aren’t they going to be all like, “Oh, you moved my cheese.” And usually it ends up not being a problem at all. So usually what we see immediately is an uptick in what’s happening in sales. And so I’ve had a couple of companies tell me they’ve doubled the number of deals that they’re bringing from first sales call to opportunity just by tightening up the pitch and getting that going. I think that’s not unusual. I worked at a company where we did it in-house where I was the VP marketing, and we, within two quarters, had doubled the revenue just by tightening up the pitch. Just tighten it up.

Lenny: Holy shit. All right.

April Dunford: Tighten it up.

Lenny: No big deal.

April Dunford: Yep.

Lenny: Okay. So-

April Dunford: It was a big shift in positioning, I’ll tell you that. Not small. Most of the time, we’re not doing that. Most of the time, it’s a tightening. We’re not saying, “Oh, we used to be this and now we’re this.” Most of the time, it’s a tightening, but usually the pitches are so bad. I’m telling you they’re so bad that there’s this low hanging fruit there that if we could improve it even a little bit, it actually has this big impact on how much stuff survives down the pipe.

Lenny: And again, if folks want to go deep into the positioning step, your first book Obviously Awesome, is a great guide, and our first podcast episode goes through this. Plus you have a guest post in my newsletter where you give them a quick start guide. So there’s so many tools to help you through this process.

April Dunford: So many tools.

Lenny: The other thought I’ve had in the back of my mind as we’ve been chatting is a previous guest, Andy Raskin, has a different framework, feels similar, but I know they’re different. His framework starts with a shift that’s happened in the world, and then here’s who’s going to win in the shift, here’s who’s going to lose. And then he goes into why this product is the best. What’s your perspective on that approach versus this approach and the big differences?

April Dunford: So the thing with that framework is I do think it works in certain conditions, but again, I think the conditions might be kind of edgy. So there’s a couple of things that I think are lacking in that structure for a sales pitch. So the first one is there’s actually no concept of differentiated value in that pitch, which for me is a giant miss. So in that pitch, it assumes that new is inherently valuable and old is inherently bad, and sometimes that’s true. So sometimes there’s just you versus the status quo and the status quo is some terrible old thing, some legacy thing or it’s manual processes or something, and you’re the only thing out there, then you can get away with that. But most of the time, we don’t have that. Most of the time, there’s multiple new ways of doing something and you just can’t say, “Well, I’m the only new and the rest of you are old and bad.”

So usually I’ve got to thread the needle. And so that’s the first thing. The second thing is that for most companies, if we really understood customer and decision, old is good, it’s safe, it’s not risky. And does anybody ever say, “No, I’m not going to buy Salesforce. That’s the old stuff,”? I just don’t think that happens. So in a lot of cases, I don’t think you can rely, it’s lazy to say, “Buy this because it’s new and new is better.” Most of the time, the customers are going to want to know, well, what’s better about it? Tell me what the value is that I can’t get anywhere else. And you’re going to have to get more specific than just saying, “Trust me, it’s new and new is good.” So that’s the first thing. The second thing is this idea of starting with a trend. On the surface it looks kind of good, but the problem is often the trend is not unique to you. So everybody else sees the trend too. And so you are starting in a way that any of your competitors could start the same way.

I did this for years where I was taught to do problem solution. We would define the problem like a trend. We’d say, “Well, the change in the world.” I was selling databases and I’d say, “Change in the world, data is exponentially growing.” It’s like, no shit. We all know that. All of my competitors could say that, and all of my competitors deal with the trend in the same way. So unless you have a particularly unique take on the trend, well, then it’s not the trend at all really, is it? It’s your insight into the trend. So I don’t think trend is that great because it’s not always unique to you. And ideally what we want is something that we can say that none of our competitors can. And typically a trend is something outside of our control. It’s out in the world and everybody else can see it too.

So I don’t think it’s great. I think that structure looks a lot like the structure we use in a VC pitch or an investor pitch because we’re talking about much longer timelines and we can say, “Look, the world is really changing and 10 years from now there’s going to be chaos and destruction and the only one standing is us and therefore there is no competition.” And because the timeframes are longer and we’re talking about disruption of an entire market, which is pretty theoretical, we can get away with a lot of that stuff in investor pitch. In fact, we want to go there in investor pitch. Sales pitch is all about right now. Sales pitch is like, okay, I’m going to exchange my money for right now. You can’t get too far into the future. Otherwise, all I’m doing is giving everybody a reason to delay, which they’re likely to do anyway because they’re indecisive about what they should do.

Lenny: I feel like I need a debate version of this podcast where people come on and-

April Dunford: I know, but here’s the thing that I think people should think about when they’re looking at all this stuff because it’s terribly confusing if you’re trying to figure this out. The one thing I really dislike about the category creation folks is they say that’s the only way that you can be successful. And in general, that’s just not true about anything. There’s lots of ways to do everything. And so I think people should mess around with stuff. And for any of these frameworks, I think they should look at it and see if it works for them and their situation. And maybe it does, maybe it doesn’t.

And I think they should steal things from wherever they can steal it and figure out what works in their own situation. My stuff, I like to think is a starting point, folks should use it as a starting point, but people shouldn’t be slaves to it. There are lots of things that work at a market, and I think the only thing that we know for certain is that we can’t say, “Well, this is the rule and it always works like this.” If it was that easy, again, this wouldn’t be so hard. We wouldn’t have podcasts and newsletters and all kinds of things trying to figure this stuff out.

Lenny: Extremely true. Well, with that, we’ve reached our very exciting lightning round. Are you ready?

April Dunford: Oh yeah. Lightning round. Oh gosh. It gives me stress. Okay.

Lenny: Okay, question number one. What are two or three books that you’ve recommended most to other people?

April Dunford: Well, that’s an easy question. So right now I’m really into Matt Dixon’s work right now, which we’ve mentioned him a couple of times on the podcast, but Matt Dixon’s new book called The JOLT Effect is really great just because there’s all this data and the things that he discovered with that data, a lot of it go against what we would consider accepted sales wisdom. And so I think that book is full of juicy nuggets and everybody should look at it. His previous book, The Challenger Sale, and there was a companion book to that called The Challenger Customer. Those were also excellent and based on a deep set of research. And those books are older now, but what we see in The JOLT Effect is all the stuff holds true. All the stuff from The Challenger Sale has not changed in 10 years. So I think those books together are really cool.

The other one that I always recommend is the original book on positioning, which is the book by Ries and Trout Positioning: The Battle for Your Mind. I have my copy of it, is dogeared. I probably read that book 100 times and I still see stuff in that book that I didn’t see before. So I think if you really want to go deep on this positioning stuff, my book is the how to book. Their book is what is it in the first place book. And I think everybody that’s interested in positioning should go read that.

Lenny: Amazing. By the way, I have your first book somewhere behind me there. I don’t know where it is, but it’s there.

April Dunford: I got mine right here so I can do this gag. There it is.

Lenny: Nailed it.

April Dunford: There’s the new one, there’s the old one.

Lenny: The YouTube audience can see that trick that you’ve learned. Second question, what is a favorite recent movie or TV show that you’ve really enjoyed?

April Dunford: Oh man, I’m going to get in trouble for this. So you know Bong Joon-ho is the guy that did the movie Parasite?

Lenny: Yeah.

April Dunford: So [inaudible 01:17:48] before Parasite, there was this book called, this movie called Snow Piercer. It’s really old. I think it came out in-

Lenny: I’ve seen that. Is that with the train?

April Dunford: 2013. Have you seen it?

Lenny: Yeah.

April Dunford: So I love this movie so much. So recently I went on a train trip with my dad and before I went to the train trip, we got talking about trains. And then we all had to go watch Snow Piercer again. Like me and my daughter watching Snow Piercer. We’re really into this movie. And it’s funny, when it came out, I was working at a startup and the CEO came and said, “Seen any good movies lately?” And I was like, “Oh man, you got to see this movie Snow Piercer.” And he went on a first date with a woman and he came back the next day and he was so mad. He was not just kind of mad. He was really mad at me. He was like, “That was the worst movie I’ve ever seen.” I was like, “Dude, you should have told me you were going on a date. I didn’t know.”

Lenny: Yeah, that is my experience with that movie. I did not enjoy it, but I think you have to go into it [inaudible 01:18:46]

April Dunford: It’s polarizing. You either think it’s amazing or you’re like, that was terrible. What did I just watch?

Lenny: This explains your taste in movies. We learned a lot about you, April. That movie is something else.

April Dunford: Did you see Parasite? That was amazing.

Lenny: That was amazing. Very different. Not what I imagined. I didn’t realize it was the same person.

April Dunford: Oh yeah.

Lenny: All right. Okay, cool. That’s two movies for people to watch. I’m curious how people think of Snow Piercer.

April Dunford: Be warned don’t go on a date with this.

Lenny: Oh man, I still think about that movie sometimes. Next question, what is a favorite interview question you like to ask people that you’re interviewing? Usually this is for when you’re hiring, so whatever this comes up for you.

April Dunford: So back when I was running teams internally back in my VP marketing days, I felt like a lot of marketing folks came with a certain amount of bad habits, particularly startup marketing folks. It’s a bit of the wild west in marketing. And so sometimes they’d come in and you get into somebody new and they’d be really smart, but they learned something at the previous company that you’re like, please never do that here. It’s not going to work here. And so I developed a thing where I was just looking for attitude. Were you enthusiastic? Are you super into what we’re doing here? And I can teach you pretty much anything. The only thing I can’t teach you is persuasive writing. And I think that’s a learnable skill. I think people can learn how to do persuasive writing.

I just don’t have time to teach it to you myself. And so I used to give people a writing test, so I’d say, “Look, think of something you bought recently and write me two paragraphs and just sell me on it.” And I used to love that test because people could either do it or they can’t. And there’s just so much stuff we end up doing in product marketing and marketing that involves a little bit of writing that it’s kind of a foundational skill. And if you don’t have that, that was the one thing I couldn’t teach you.

Lenny: Wow, that is fascinating. I’ve never heard of that as an interview question. And I love it. I feel like product managers-

April Dunford: I stole it from a company that made me do it before I got hired, and I was like, this is a really smart thing. I’m [inaudible 01:20:53] stealing it. My thing was I got anxiety and I couldn’t decide what product to write about, and I had literally just bought a new pair of running shoes. So I wrote two paragraphs about my new Brooks distance running shoes. But it was good. I got the job.

Lenny: It is an excellent segue to our next question, which is, is there a favorite product you’ve recently discovered that you really like?

April Dunford: Right now I’m kind of into, I don’t even know how to describe this category of things, but things that are kind of low tech but are awesome. And so one of the category of things that I really love right now is I’m really into fountain pens. I don’t know if you’ve ever written with a fountain pen. [inaudible 01:21:35]

Lenny: I haven’t, but I know what they are.

April Dunford: And so there’s this company, Lamy, they’re based in Germany, and they make the world’s greatest fountain pens. They’re beautiful, they’re amazing. Some of them are really expensive. If you want to spend a lot of money on a pen, you can. But they have this one called the AL-Star, which is not an expensive pen. It’s 20, $30. It may be expensive for a pen, but it’s not so much money that you wouldn’t feel bad if you lost it. So Lamy AL-Star. That’s my great product lately. I don’t have one right here. I should, it’d be a great prop to pick it up, but I actually don’t have my bag here and it’s in my bag. But Lamy AL-Star. You Google it. These are beautiful pens. And then if you haven’t written with a fountain pen, it takes a minute to get used to it, but then it’s like, gosh, it just feels great. You’ll never write with a ballpoint pen again.

Lenny: I was going to ask, is it the feel of the writing that you really enjoy about it?

April Dunford: Feel. Totally different. Yeah. Amazing.

Lenny: I use Muji pens. I don’t know if you know these pens.

April Dunford: Oh yeah, these are actually really good. They’re like roller ball pens, roller ball pen, very good, but not as good as the fountain pen.

Lenny: It’s no fountain pen.

April Dunford: The Muji pen is pretty good.

Lenny: Then do you have to dip it in ink and stuff? How does that work?

April Dunford: No. You actually, they either come with a little cartridge that you stick in or if you feel bad about the environment, you don’t want to be throwing out cartridges all the time, there’s a refillable cartridge, so you basically just stick another thing and it sucks it up and yeah, you don’t dip it in ink. That would be crazy. I can’t take that on the airplane, man.

Lenny: Confiscate your ink. All right, questions get a little more challenging potentially or really easy. Do you have a favorite life motto that you like to repeat to yourself, you like to share with people, that you find useful to come back to?

April Dunford: My thing lately is, and maybe this is just an old person thing, but my thing lately is nothing’s a big deal. Nothing’s a big deal, nothing’s a big deal. And so you’ll have stuff that you think is a really big deal, positive or negative, and you’ll be like, wow, if this thing happened, it’d be so great, and then it happens and you’re like, yeah, it’s pretty great, but things are good otherwise, or it’ll be the opposite. Like, oh, if this thing happened, it’d be so bad. Then it happens and you’re like, that wasn’t that bad. And so I don’t know if this is good or bad, but lately I’m in this zone of I’m in this kind of chill zone where I’m like, nothing’s a big deal, man. Everything’s cool.

Lenny: That super resonates. And as much as you say that to yourself, it’s still hard to convince yourself of that sometimes. But that is a really good motto. I’m going to steal that myself. I kind of say that to myself often in different way.

April Dunford: Yeah.

Lenny: What is the most valuable lesson your mom or your dad taught you?

April Dunford: Yeah, it is funny because it’s a little bit related to that. So my dad ran a business, so I grew up in a really small town and my dad and it’s cottage country in Canada. And so my dad ran the local toys for tourists, like boats and motorcycles and ATVs and that sort of thing. And he ran that business for years and years and he sold it a few years back when he retired. But it’s a neat thing to grow up in entrepreneurial family because you kind of see this highs and lows. The business is really good. Then the business was really bad and then we were all broke and then the business was good and we were not broke. So there was this thing, and my dad used to always kind of have this attitude of you just got to grind it out.

You’re just going to grind it out. There’s going to be good stuff, there’s going to be bad stuff, but the key is to just keep going, just keep going. And so he ran that business for whatever, 30, 40 years. I don’t know. His motto is the home of fun since ‘71. So he started it in ‘71. I think he sold it three, four years ago. So a long time.

Lenny: Wow.

April Dunford: It all worked out good in the end. And so I don’t know, I think there’s something cool about growing up in a family where you can see the highs and lows and then again be like everything’s we’re just grinding it out over here. Nothing’s a big deal.

Lenny: It’s clear where all that comes from now.

April Dunford: Yeah.

Lenny: Final question. You do a lot of traveling, you do a lot of speaking, you go to a bunch of cities. I’m curious just what is your favorite either city that you go to that maybe people may not know about or venue that you speak at?

April Dunford: It’s such a cliche, but I love Paris. I just love it. But for me, Paris is like a particular vibe. So when I was in university, I did an exchange when I was in engineering and I did third year engineering at a school just outside of Paris. And so I spent the whole year there, learned a bit of French. My French was pretty good at the end. My French is really bad now. So I kind of get Paris. I like Paris. And so when I go to Paris, I just have the best time. I have my set of restaurants I want to go to. I have my handful of places I want to go shopping. I put my butt down in a cafe, look at the beautiful people, drink my nice coffee. I just really dig the whole vibe of Paris and people are starting to know that now. So French companies will call me and they’ll say, “Do we get a Paris discount? We hear you like coming here.” And I go, “Okay.”

Lenny: Now this is going to [inaudible 01:26:51]

April Dunford: There’s a great product management conference there called La Product Conference run by these folks at Tega, shout out to Tega. So I’ve been there a number of times for their conferences and they do an amazing job and the venue is really great. It changes around. But last year, the last time I went there, which was two years ago, it was at an old theater in [inaudible 01:27:13]. Absolutely beautiful. And that was a pretty great venue in a great city with a great conference. So yeah, shout out to French people.

Lenny: Oh man. That sounds dreamy. Paris. I see how that could be a favorite. April, I think we accomplished everything we were hoping to accomplish. I think everyone that has listened to this podcast is going to be better at pitching and selling. It feels like even if they take one element of this framework, say starting with an insight or focusing on different value will make them better. And so I’m proud of us. Thank you so much for doing this. Two final questions. Where can folks find you online if they want to reach out and how can listeners be useful to you?

April Dunford: So where can people find me? I’m aprildunford.com. The only social media I’m doing these days is LinkedIn. I’m a bit social media-ed out. I’m experimenting a little on threads and Instagram, but LinkedIn is a good place to find me if you just want low lift way to follow my stuff. But I’m doing all the things now, Lenny, I got a podcast, it’s called Positioning with April Dunford. I got a newsletter that’s also called Positioning. You can find that if you go to, it’s on Substacks, you can find it there, otherwise aprildunford.com/books and you can sign up there. But those are the big things. And then there’s the books, obviously, if you want to learn more about this stuff. Everything I know is in the book. There isn’t stuff that I know that isn’t in the book to be honest.

Lenny: Amazing. And then how can listeners be useful to you? Just check out those things.

April Dunford: I guess so. You know what? I’m in this phase. I think, again, I think it’s an old age thing. I am in this kind of philosophical phase where I’m not going to be doing this forever. And what I’m trying to do right now is get everything that’s useful out of my head and out in the world before I’m done. And so right now I’m very focused on delivering useful things for other people. I didn’t think I needed to write a book about sales pitches, but then I got the idea in my head, everybody’s sales pitch is so bad and there isn’t a book on how to build a sales pitch. And I’m not saying mine’s the world’s greatest thing, but it’s better than nothing. So this is what I’m trying to do right now. I’m trying to be useful to other people because pretty soon I’m not going to be doing anything, I think is the idea.

Lenny: Arnold Schwarzenegger’s new book is called Be Useful. And I feel like that’s the perfect description of how to be successful and especially in the work that we do, just helping people. But I keep coming back to that. It’s just be useful.

April Dunford: I think this is a really important thing. When I wrote the first book, people started writing back to me and saying, “Oh, your book was so great.” And my reflex action was to say, “Oh, I’m glad you enjoyed it.” But then I stumped myself and I was like, you know what? I don’t actually care if you enjoyed it. This isn’t entertainment. I’m actually trying to create something that’s useful. So what I really want is for people to read this stuff and come back and say, “That was useful. We were struggling with this thing, and that unlocked something for me and that was useful.” And that’s what I’m trying to do right now.

Lenny: April, thank you so much for being here. This was amazing.

April Dunford: Thanks so much. It’s always good to be here.

Lenny: Always good to have you here. And we might do a V3 when you do a third book if you ever-

April Dunford: No, not happening.

Lenny: Okay. All right. Well, bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Glossary

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