Marketing

Do It! Selling: Strategies For Success In Today's Market With David Newman

Offer value, invite engagement—that’s the key to winning in sales. In this episode, Mark Cox sits down with David Newman, the author of Do It! Selling: 77 Instant-Action Ideas to Land Better Clients, Bigger Deals, and Higher Fees, to dive into the secrets behind his no-fluff, high-impact approach to sales. David’s journey from a theater major struggling in New York to a successful consultant is filled with hard-earned lessons that every entrepreneur can relate to. Together, they explore how to overcome the aversion to sales, the power of asking the right questions, and the importance of consistent, value-driven content. Whether you’re new to the game or looking to refine your strategy, this episode is packed with actionable insights to help you land better clients and close bigger deals.

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Do It! Selling:  Strategies For Success In Today's Market With David Newman

We've got a great conversation here. This episode is with David Newman. He is the author of Do It! Selling: 77 Instant-Action Ideas to Land Better Clients, Bigger Deals, and Higher Fees. He is a professional services sales expert. He works with leading consultants, coaches, and speakers who want to land better clients, bigger deals, and higher fees. He's got a specific target market, but these 77 instant action ideas are universal in terms of smart methodical B2B sales. They're applicable to all sorts of folks, which is why I was excited to get him on the show.

The other thing is that it's an extremely well-written book. With these 77 ideas, David has gone through the effort of making them concise and powerful, leveraging core concepts and B2B sales, and providing tools you can download to apply the idea. I love the way the book is laid out. It's a book that you're going to leave on your bookshelf and go back to repeatedly because it gets specific on things like scripts, ideas, and approaches to conversations.

One of the things I like so much is David's simple clarity in the way he writes and speaks. He's got this simple and clear but powerful definition for something like marketing words that offer value, invite engagement, a simple definition of selling, send invitations, and spark conversations. We talk about a couple of different concepts in the book, not all 77, but we do get to the first conversations. He's got five powerful tips for first-contact calls. We get into all of them. We get into the four ways to create follow-up magic. It’s powerful. A little bit of a spoiler alert. The first one always leads off with the prospect's comments from the previous call.

David started this career after starting in the theater. We're going to read about that journey. He’s an interesting fellow. He’s the host of his own podcast called The Selling Show. It's got over 400 episodes. You're going to enjoy this conversation with David Newman. I know I did. If you do, please like and subscribe because that helps us. Thank you for doing that. That's how we get great guests like David.


David, welcome to the show. I was excited to talk to you.

Mark, it's great to be here. Thanks for having me.

We only interview the folks who've written books in selling that we like, David. I got a call that said, “There are many things I like about Do It! Selling: 77 Instant-Action Ideas to Land Better Clients, Bigger Deals, and Higher Fees that I've already bought Do It! Marketing.” I haven't gotten it yet. I did it this morning, but I've got the Do It! Marketing coming my way because I'm in your target market. A lot of these things are so applicable, and I learned many things from them. I had a chance to listen to a few episodes of The Selling Show. I got asked this question because it seems clear that you were a Theater and Drama major. How does a Theater and Drama major end up being an expert in selling, professional services, and coaching?

From Theater To Sales

I started college pre-med. I failed out of Chemistry, Physics, and Calculus all in the same semester. I decided to change my major to Drama and English. I had so much fun doing that. I went to graduate school and got an MFA in Stage Directing. I did several years of professional theater in New York City. That was a crazy episode, but I wasn't making any money because it's hard to make money in theater in New York City. It's like going to LA to be an actor. You end up waiting tables.

A friend of mine says, “There's this adjunct professor thing opening. This was a guy who had the job. He was moving away. Would you like to interview for my adjunct faculty position?” I started teaching in my graduate school. I did that for a couple of years to make ends meet. Another friend says, “You could do this teaching thing for companies.” That's called corporate training.

In 1992, I launched my corporate training and consulting career. That spanned three different jobs. I did that for several years. I ended up with some HR consulting management, technology, and firms. Dumb as I was, in 2002, I said, “I can do this on my own. I know how to teach, train, and consult. How hard can it be?” Mark, I found out how hard it can be because when you're on your own and leave the corporate nest, it's about selling the work. It's not about doing the work.

I knew nothing about marketing, sales, lead generation, and business development. I was a babe in the woods. I was also a generalist consultant and trainer. I had 30 different workshops and 30 different topics. I realized that if I wanted to eat, I needed to learn how to sell. I read all kinds of books. I connected with mentors. I took courses. I became a student of the game. About several years into this, I'm like, “I have no niche. I have nothing. The sales and marketing thing is pretty cool. Why don't I teach what I'm learning to folks who are several years behind where I am?” That was the whole genesis of how the drama major ended up in a marketing and sales training role.

Do It! Books

Here we are, fast forward 1,800 clients later, you've worked for some of the largest organizations in the world. I’m having finished my first book. David's got three books, Do it! Selling, Do It! Marketing, and Do It! Speaking. I'm amazed at a couple of things, David. I'll call out to those folks who are going to pick up this book, and you should. First of all, the design and clarity of the book, it's a good-looking book. It's easy to read. I love the fact you don't see a lot of color books out there. These things matter. We dream in technicolor. That’s something I'm taking away from myself next time.

Do It! Selling: 77 Instant-Action Ideas to Land Better Clients, Bigger Deals, and Higher Fees

The way you've laid this out, these short snippets and action ideas that are clear. It feels to me like you're the example of that Mark Twain quote, “I wrote you a long letter. If I had taken more time, I would've written you a short letter.” You took the time to write a short letter. It's all gold. There's no fluff. There are no stories that aren't relevant. There's no filler.

In many of these action items, there are tools you can download to apply the concept in the book. It’s a bit of the Bucky Fuller. Those of you who are Mensa candidates remember Bucky Fuller, the Founder of Mensa, who said, “If you want to teach someone, don't bother teaching them. Show them how to use a tool because that's how you teach them for life.” It's a spectacular read.

A lot of times, when we have guests on the show, David, what I'll do is I'll read and highlight the book. I'm going to go back and dictate my highlights. I have a two-page summary. I can go back to it someday because I want to retain it. I'm not saying this for the show. This is the book that would stay on my shelf because I'm going to go back. There are some things I've picked up here that are helpful. There's a clarity of message. It's the way you are. Maybe it comes from the theater background, but was that an intentional focus to make sure it's short, clear, and powerful?

All three of my books are written in this format. I call them microchapters. When folks come to me and say, “David, I want to write a book, but I don't have time to write.” I say, “Don't worry. They don't have time to read. Write short.” If I put my whole publishing philosophy into four words, it would be to write short and market hard.

It was a book publishing blog. This was in the last couple of years. They were saying about short attention spans. Everyone wants to write the 50,000 to 60,000-word mega monster business book. They were saying, “If you're sending this to CEOs, VPs, or busy senior corporate leaders, they don't have time. Don't write a book. Write half a book.” That was the advice.

Two hours and thirteen minutes is the flight time from New York to Chicago. If they can read it, scan it, or skim it and get enough of an idea of your professional expertise in those two hours, because, Mark, folks like you and I don't get hired based on books that clients do not finish. It’s like, “Did you read David's book?” “I only got about a third of the way through it and put it aside because it was too dense and hard to read.”

Microchapters do two things to help experts. Number one, it helps to encapsulate your thinking in a short, sharp, little package. It also makes the book more digestible because, Mark, I'm sure you read a lot. I read a lot. We want to have that completion complex. We want to have that little happiness going off in our brains with dopamine. I finished another chapter. It's like, yeah, you read a page and a half. If you read a page and a half, and you're seeing the next chapter right there, you're like, “I'm making progress.”

The best compliment that I got on all three of my books is a backhanded compliment. They said, “David, I love your writing style. It's perfect bathroom reading.” I was like, “I will take that in the spirit it is intended.” That was the nature of the microchapters and the short, sharp, clear little nuggets that are the writing style.

We're critical of sales books. Because of the show and my nature, I've read hundreds of sales books. We've had over 100 guests on this show. Out of consideration, we read the books they write before they come on the show. There are some fundamental truths that you've got in here. We've heard that people who have lived this life understand. Because you've got a specific target niche that you're trying to support and help coaches, consultants, and trainers looking to get bigger clients, bigger deals, and higher fees, you get practical. When you're talking about a sales process or a first call with someone, you give specific examples of the four things to do. Here are a couple of turns of phrases you can use.

If you're in that category, this is the book you can pull away. You will go back to it, and you'll start to leverage some of the, I won't call them scripts as much as guides, but they're logical. You're also referencing some sales fundamentals that are universal regardless of who's reading. Whether or not you're a trainer, a coach, or a consultant, getting through that first call is critical. There are a couple of ideas that are powerful. People can take away these tips no matter what they do. If you don't mind, we'll jump into a couple to get right into it.

Whenever someone has the book in front of them, there's a little voice in my head going, “I hope I remember what I wrote and what he's about to call out here.”

When we're in front of a group of people, every once in a while, there's somebody who's a zealot and reads every episode. They go, “Mark, you referenced this data point, and this reference point from CSO Insights back in 1987,” I go, “It doesn't even ring a bell. It doesn't even sound like me.” I'll give you some context.

Action item number four, do you love selling? It was the one that jumped out at me. Given the title of our book, Learn to Love Selling, do you love selling? You have to believe in selling. You have to understand that people have some of these challenges. I love that down at the bottom, we might be feeling anxious and depressed. We get paralyzed, overwhelmed, and mystified. The summary point that says no sales, no clients, no money, no bueno. That's simple. You have to do it. Are we going to be the best pizza parlor that's never had somebody come in the front door, or are you Dominoes?

This is where it's not selling expertise that comes from the book. There's this expertise you have as a growth-oriented entrepreneur. There are many of those other entrepreneur books. There wasn't a question on this one so much as we wanted to call it out because of the title of our book. Let's go to the definitions. I love the definitions. You've come up with these four-word definitions. One is for marketing. Let's talk about the top end and sales.

This leads to a mindset. It makes it so much more helpful for those who didn't grow up in sales or those of us who didn't decide we wanted to be in professional sales when we were ten years old. That's 99.999% of anybody who's in professional sales now. On the marketing front, forward definition, offer value, and invite engagement. It doesn't sound so hard.

Marketing

My first book was about marketing. My second book was about speaking as both a marketing tool and a sales tool. This book has a sales focus. People are not afraid of marketing. They might not understand it. They might not do it well. They might think it's pitchy and like, “Buy my stuff.” The sales part, which you're an expert in, that's where the fear comes in. They don't want to be salesy. They don't want to be pushy. There's a whole population of entrepreneurs that are sales averse, which is why your book is important.

Conversation

From a marketing standpoint, when people say, “I'm hesitant to market my stuff. I don't want to be always talking about me, my offers, my services, my programs, and my products because that gets old.” I would agree with you. That does get old, and it doesn't work. Offer value invite engagement is about how to be radically generous and radically helpful. Provide content that people will benefit from even if they never buy from you.

Is your marketing content, and I mean your social posts, newsletters, LinkedIn profile, and LinkedIn posts, can people extract value from them? When you read Mark's book, LinkedIn, and articles, and when you watch the YouTube channel, are you saying to yourself, “This is valuable. Imagine if I became a client?” That's offer value. Out the goods out there in the marketplace.

A lot of folks are afraid of doing that because they’re like, “That's my stuff. If I give this away, they're not going to hire me. If you don't give it away, there's no way they're going to hire you. If you give it away, a small, teeny, tiny percentage are going to be able to run with the ball and get some initial result. No way are they going to get the massive transformational results of the clients who hire you. Part one is offer value.

With invite engagement, I hear this a lot from clients and friends who say, “David, I've been sending a weekly newsletter for several years. It's never given me a shred of business. David, I posted the one-minute video on LinkedIn every single morning for the last several years, and it's never brought me a shred of business..” I look at these newsletters and watch these videos. I say, “There's no invitation. There's no next step. There's no like, comment, subscribe, opt-in, or book a call.

The call to action and the invitation to participate further are not buy my stuff and hire me. The invitation could be simple, like, “Can I get an amen?” Comment and like are the easy ones. A little bit more involvement and engagement is like, “Do you want to download this thing? Are you willing to trade your email address for a free PDF, video training, and mini-course?” That's level two. It’s more of a commitment because you know that you're opting into their world.

Level three is like, “If you think this might be helpful to you, let's book a chat. Let's discuss where you're at. If we can help you, it’s great. If not, we'll point you in the right direction, and there will be no harm or foul.” When I look at these several years of email newsletters, and there's not a single invitation to take the next step, people are lazy, busy, and befuddled.

All the folks that are reading are saying, “They know the next step. They could have replied to that email. They could have called my phone number, which is right there on my website.” They could have, but because they're lazy, busy, and befuddled, you don't tell them exactly what to do. Inertia is going to take them off into something else. They're going to click off, scroll by, delete that email, and say, “This guy, Bob Jones, has an amazing email newsletter.” They might even be hiring someone else because they don't know all the things that you do.

How many times have we gone to a prospect or even a new client, and the client hires you for something, and you found out that last year, they hired someone else that does something that you do, but the client never knew that you did? They’re like, “Mark, I wish I knew that you did sales assessments and sales kickoff meetings. We hired this other person to do our sales kickoff, and it was disappointing. I wish we knew that you were a speaker.”

You're a speaker, but if there's no invitation at the bottom of the email newsletter, for example, hire Mark for your next sales meeting, sales conference, or sales kickoff, here's the info packet. Put that in there so that you're not trusting people to use their own initiative. You're giving them a clear next step in how to engage with you. That's an invitation.

I love the focus on those four words. This is something that you refined over the years, but it's powerful. I couldn't help but smile when you were talking about that, David, because we do many things where we're training big groups of people. It's hard for people to process the fact that they may have explained to the community, a client, or a prospect exactly what their business did. They have a hard time understanding Hermann Ebbinghaus’s Forgetting Curve, which says, “An hour after the meeting, that person forgot between 50% and 75% of everything you said. A month from now, it's 90% to 95%.” People go, “What do you mean? It seems difficult.”

One of the things that has been helpful for me going from the corporate world to becoming an entrepreneur several years ago is that I am befuddled by many things that are on my radar regarding things that I want to do with the business. These things are passing ideas, and the night they come, they go. Every day, I can only get through the three things that are most important for our business.

This idea of staying front of mind, that the number of times somebody engages us and we end up into this conversation. As we get through the conversation, they say, “I've been following you for several years.” You go, “For several years, didn't you think to trigger a conversation several years ago?” We do have those calls to action, but they don't. They want to get familiar with you. They want to make sure there's some value in what you share. It's on their timeframes. It's such a helpful point and a beautiful definition.

Let me do a public service announcement. If you've been following Mark Cox for the last several months, you know he is the real deal. Get on his calendar, pick up the phone, reply to the email, and comment on the show. Several months is all you need for Mark Cox. You don't need several years to wait.

David, remember you said, could you come on more often? You're going to be on every second episode now. There you go. If you're open to doing that in that voice, you're on every second episode. Let's do the episode together.

Clip that out and use it as a commercial.

The four words from marketing are offer value and invite engagement. Double-click value. The four-word definition for selling is to send an invitation and spark a conversation. What do you mean by a conversation?

One of our mantras that shows up somewhere in the book is nothing good happens outside of a conversation. You can send emails until you're blue in the face. You can post on social media. You can even send cookies in the mail. You can send an amazing $50 pen to an executive with whom you want to have a conversation. None of that matters until we are voice-to-voice, screen-to-screen, or face-to-face. This is an area where the sales-averse. This is the part that terrifies them.

Mark, what happens when the dog catches the car? I got a call on Tuesday. The guy replied to me. He wants to have a call with me on Tuesday. Their heads explode. Everything that we do in marketing and the front end of sales, like prospecting and lead generation outreach, is designed to bring you into that first conversation. People have this like, “This is a huge pressure moment. I have to sell, pitch, and blast them with my amazingness. Nothing could be further from the truth.”

No matter what business you're in, you could be selling products, services, or expertise, the framework that I recommend that you hold this initial conversation in, and there are a lot of guides, frameworks, and language that you can use in this first contact meeting. Think of it as if you're already hired. They're already a client. You have nothing to hide and prove. The way that I open these conversations is, “Mark, great to speak with you. Let me ask you. Do you mind if I treat you like a fee-paid client during this call?” People will say, “That would be great. You can even see their body language change.” Sometimes, they go, “What does that mean?” I say, “I'm glad you asked.”

It means a couple of things. Number one, it means that I want to make sure that we maximize the value of our time together for you, which also means that I'm going to ask your permission to interrupt and productively redirect if I feel our conversation is going off track. I would do this with a paying client. Number three, there may be some things that you share with me. I'm going to tell you the honest truth. I'm going to tell you what you need to hear, not necessarily what you want to hear about you, your company, and your team.

Do I have your permission to do that? They say yes. They're already in the house. They're already in the family. All the pressure that's on you as a seller has gone away. You can start doing your initial diagnosis. What's been going on? What prompted you to book this call? What's wrong with your leadership, sales team, technology, and innovation that we're helping them with? How long has that been a problem? What do you think is costing you time, dollars, hours, profit, percentages, rework, wasted time, and wasted effort? We're in a conversation. Look at every prospect as if they're already a client, and they don't know it, or they haven't signed off on the paperwork. The more you treat prospects like clients, the more clients you will get.


This is tip number 29. Five tips for first contact calls. The first one is a great opening question. The second one, do you mind if I treat you like a feed-pay client? It's the same script that David went through, which is powerful. This is the dirty little secret that trainers, consultants, anybody in professional services, lawyers, engineers, and consultants don't know.

The truth is this is the easiest part of the conversation because all you are doing is pulling information from them with amazing questions that get them trying to paint this better future for themselves. They're emotionally connected to either the pain they're in or the better future. You are sitting back and asking questions.

My belief is that most of the folks get a lot of these folks, like lawyers, financial professionals, and consultants. Their concern is they think they need to pitch. We're going to get the PowerPoint. My rule of thumb is never to open PowerPoint again during a conversation. It will kill your conversation. Don't go anywhere near a demo. Don't go anywhere near PowerPoint. Have a conversation.

Get Into Action

The easiest one in the world is thank you so much for setting up time with me. I'm delighted to chat with you. I took a look at your website. It looks like you've been growing. Congrats on the acquisition. I'm excited to hear about that. On LinkedIn, it looks like you've got 125 employees, but you get seven open job postings. Things are moving in the right direction. I’m excited to hear all of it. What prompted you to reach out to me?

It’s something crazy easy, nice, and open-ended. We can sit back and have this conversation. You and I are having this conversation. You've packaged this up for your audience in a new way. We've been doing this for several years, packaging up. The reality of it is that this is what Dale Carnegie suggested we should be doing in 1939.

You'll love this, David. At one point in time, I had this, and I wouldn't call it imposter syndrome, but it was perplexing me that in our company, we hadn't come up with a brand new way of helping another human being that no one's ever thought of before. That would be the magic potion that would completely change B2B selling. It perplexed me so much. I went down to see one of our friends, Frank Cespedes. Through this show, we got to know him from Harvard. He has written nine books on B2B selling. He is fantastic. He's been teaching the sales program at Harvard for many years.

I had this conversation with him. I said, “I feel like an impostor at times because, Frank, I've been doing this for many years. Nothing's changed. This is what I was doing in 1995 to be successful.” He brought up a great point. He said he had had this big group of super high-end entrepreneurs at a Harvard course. He was having a conversation with them. It wasn't resonating. He went back to some principles in search of excellence back in 1992. He said this thing lit them all on fire. He said, “Sometimes, you have to take these universal principles, but they need to come out in the voice of that generation for that particular group.”

There was a theme of this in your book, David. A lot of these are fundamental truths. The second thing I thought was that you should take it a level down because you make it simple for somebody in professional services to understand the concept but immediately apply it. The other thing I love about early in the book is that after about section one, David says, “Let's take a pause. What have you done with the information in the book so far? Are you going to make some behavioral changes here? Are you going to read another book?” What a great move. That screamed right from the page. You want me to do better, not to sell another book or do another workshop, but you want to change someone's behavior. I bet you get a lot of feedback on that.

The whole Do It concept and get into action are all about implementation. Great ideas are a dime a dozen. This is why there are a million weight loss books and how to get rich books. The key to weight loss is to move more and eat less. The key to becoming a zillionaire is to spend less and save more. There are a million personal finance books out there. The ideas are useless. The implementation and the execution of the ideas.

Given the stage and phase of the business that you're running, your market, audience, and prospects that you're marketing and selling to, you'll know how to adapt these ideas to your own personality preferences and strengths. It’s the same thing, Mark. In your book, we can keep reading until we're blue in the face, and no one is going to sell anything anymore. It's about the implementation of the ideas.

Sometimes, we can be relentless. People will say, “Mark, I love your podcast. This podcast is amazing. I read your book three times. I highlighted every other page. You say, “That's beautiful. Thank you for the kind compliments. I'm curious. How has listening to the podcast or reading the book impacted your sales results?” They start looking at their shoes. Their shoes start to get fascinating. They're looking down, and they’re like, “I still love your ideas so much. You're such a rock star. You're amazing.”

You and I leave those conversations a little bit deflated. We're not here to write books and publish podcasts. We're here to help people tap into their inner potential that, for some reason, has been blocked up until now because they're sales averse or they don't have the sales skills, discipline, or conditioning that they need to reach their goals. I love it when people appreciate my ideas, but I love it more when they make money with them.

Follow-Up Magic

David, I couldn't agree more. There are two stories. We end up with some of the clients we work with. We used to help them and teach them how to interview salespeople. It’s a tricky thing to do with one in three churns every year. I want you to hear a lot of interviews with professional salespeople. You'd say, “Is there any methodology you follow? Have you had any training before in your career?” They'll come back and say, “I read The Challenger Sale by Matt Dixon and Brent Adamson.” We're going to go, “We've had both of them on the show. What are you applying from that book?” This is where the shoes get attractive. They've taken nothing from it.

I love the idea of clarity in your book, which is something people should apply almost every day. You talk about that. One of the important things is it has to be a habit. It has to be something we think about and do every day. We had another client who was one of our first clients ever from several years ago. They used to continue to send all their new salespeople to our training, and their leaders who would come to our training.

At one point in time, they brought us into their office to do some work. We could still see these templates that we had given, but they were the ten-year-old templates from the early days. They were still leveraging them. We felt happy that they were trying to operationalize and still get value from what we had done.

We do it differently now when we're doing large group training. We'll do the training, but before we do the training, we define specific desired outcomes, metrics, and outcomes that we want several months after the training. As part of the training, we regroup with the leadership team to track progress with senior management. We keep the sales leadership team accountable to make sure we're executing these things, and they don't go through another sales kickoff where it was fun but didn't change any behavior. We want to make that change critical.

I want to call out one other thing. We're not going to go through 77 of these ideas. Many of the people who are reading this are looking for something they can take away and apply. Item number 58, 4 ways to create follow-up magic. The number one need of most human beings outside of food, water, and sustenance is to feel like they are heard. Always lead off with the prospect's comments from the previous call. Did you even hear what they were saying, “Start there and break the wall completely down?” This is all part of feeling like they're already doing business with you.

One of the top sales minds out there, in our view, is a guy named Andy Paul. He's probably into 1,500 podcasts. He's spoken to everybody. One of the phrases he loves to to use, which we like, is, “The folks who win in a sales situation are the folks that the buyer believes understand them and their situation better than anybody else.” You get comfortable.

It's not about prices you bring up or service features. Those things oftentimes don't even matter. Does this individual understand our world and what's important to us? They didn't hear us. They understood what we were saying. I love the easy one. It’s to ask follow-up questions to every statement they make. Who, what, how, and why. These multipliers keep them talking.

It's the who else, what else, how else, where else, and why else? Who else will notice these improvements? What else would be important to them? How else do you think you might benefit? Where else has this been a problem? All of those who, what, where, and why else questions are sales multipliers. Those are revenue multipliers because, from the prospect, you're inviting them to share with you what the problem multipliers are. When you have problem multipliers from your client, you have sales multipliers for multiple different ways that you can help them solve those multiple problems.

Sometimes, people believe this is self-evident, but you'll ask a question like that of a senior executive. They haven't thought about the answer until they say it out loud because you ask the question. It imprints. They are emotionally tied to it. You ask a question. How big a priority is the firm for this? Somebody comes back and goes, “It's an interesting question. If we don't fix this revenue issue, I won't be in this chair several months from now.”

There have got to be a top three. What are the other two out of interest? What are the implications if we don't address this? I'm not going to have a job. These are the things that crystallize in the mind of the buyer. I love a conversation in a follow-up call where somebody comes back and goes, “That's a good question.” That means we did our job. You talk about that in the first conversation, doing some myth-busting and adding value.

It occurs to me that even if we misread the situation badly and ask a question about something that's not important to them at all, and the executive comes back with, “Mark, that's the least of our problems.” Have the presence of mind to say. “Got it. What are the top three?” We don't care about that at all. That's the least of our problems. What's the top three in the most category? Have some fun with it. The other thing is amateur sellers put so much pressure on themselves. They're serious. Professional sellers like you and me like to have fun. We like to make the prospect smile or maybe even sometimes laugh. We humanize the sales conversation with humor. That makes selling so much more easy and fun.

Amateur sellers put so much pressure on themselves whereas professional sellers like to have fun.

We were talking about dopamine at the beginning. We’re familiar with dopamine. Curiosity also triggers dopamine. When we're asking them those questions, this is why it's so easy if you do it this way and have this conversation. The whole conversation's about them. To be authentically curious about the answers, they're not answers leading to my sales pitch. They're answers where I'm authentically curious about how to help this person get a better future. You or I are clear. If we can help them, it’s wonderful. If we can't help them, but there's somebody else we know who could help them, we'll be the first to do that. We understand good things come when you take this approach. Your intent comes across.

More so than any sales technique you come from. What you're talking about is where you come from, your intention, and your character. No matter what script, template, or framework you use, they can tell if you've got the old sales breath or commission breath. They can also tell when they're talking to someone who is genuinely curious, genuinely there to help them and serve them, and completely detached from the outcome.

That is the other magnificent point for everybody reading. Anybody in professional services, training, and consulting, the idea is you're not trying to find another sales opportunity. You're having another conversation with the right actor for you, the right person. The ballerina and not the truck driver is another theater analogy.

The idea is you're not trying to find another sales opportunity you're having another conversation with the right actor for you the right person.

I'm having this conversation about helping them. He's a guy from Harvard, Dr. Nick Morgan. His book is called Can You Hear Me? He talked about how we can sense another human's intent with nonverbal cues in milliseconds. How do we go into that conversation? When we got ready for this episode, I heard you on your show, but we met for the first time. We got on this Zoom call. I thought to myself, “This is going to be fun. This is going to be a great conversation. I already like David.” These are things that we can connect.

The truth is that it is better for the process. It's also better for the individual because this is what you want to do with your life and career. It's not about pitching and cajoling. I'm not trying to get one more opportunity in the funnel. I'm trying to help another human being. What ends up happening is great things happen for everybody.

David, we are going to chat again. I have to call out the last thing I loved about that number 58, which is four ways to create follow-up magic. It's not a need or a pain until you hear it from them. You think, “I know the reasons people engage in sales training. I know the reasons people buy enterprise software that does financial reporting.” It doesn't exist until they say the need, the paint, or the opportunity. The return on investment doesn't exist unless it's in their model with their metrics and hitting their goals, whether it's MPV or payback. Those things have to come from them. I love it has to come from that.

Reach David

Tim Hughes is a great guy. He wrote a fantastic book called Social Selling. He used to sell large-scale enterprise software to massive retailers in Europe, including Marks and Spencer, which is one of the largest retailers in the UK. Every business case they write had to come back to how many more pairs of undergarments because that's their number one category killer. Do they sell because of this project? It was always that. Would this result in more undergarments being sold or not? That's the only metric we understand. David, a couple of things here. Thank you for joining the show. We are going to, if you're open to it, have you back for Do It! Marketing when I read that book.

That would be amazing.

We'll get that on the radar. A lot of the folks reading are going to want to reach out and engage with you. Who do we want? Who is that ideal client profile for you? How do they best make contact with you or learn more about you and your fantastic offering?

We work with professional services firm owners. If you're in the business of selling your expertise, which usually takes the form of a training company, a consulting firm, or a coaching company, and all B2B. Mark and I are brothers from another mother. As far as some resources, we have our podcast called The Selling Show, which is at TheSellingShow.com, and some free resources on the main website, which is DoItMarketing.com. There's a blog there and a free 37-page sales and marketing manifesto. That's at DoItMarketing.com/manifesto. Our free on-demand web training is at DoItMarketing.com/webinar.

When you buy the book, Do It! Selling, you go onto an online system that's going to provide all the tools to execute some of the core concepts in the book. You're going to get your payback immediately from the book for downloading these tools. You can apply these concepts to you and your business. David, thanks again for joining the show. What a pleasure meeting you.

Thank you, my friends. Same here. As they say at the end of Casablanca, “The beginning of a beautiful friendship.”

Thank you so much for joining. As you know, we run the show because we want to improve the performance and professionalism of the world's most important business discipline. In doing so, we believe we're improving the lives of professional salespeople everywhere. Thanks a lot for reading. We're growth-oriented. We know we can continue to elevate the way we run this show. Please keep your constructive criticism coming to us at MarkCox@InTheFunnel.com. That's my personal email. We respond to every single person who gives us good ideas and keep them coming because that's how we get great people like David. Thanks again. Continue to sell well. We look forward to seeing you in the next episode.

Important Links

About David Newman

David Newman is a Certified Speaking Professional and member of the NSA Million Dollar Speakers Group. David is the author of the business bestsellers, “Do It! Marketing”, “Do It! Speaking and “Do It! Selling”.

David has worked with over 1,800 consultants, coaches, and speakers to help them accelerate their revenue and grow their business by 50%-500% in less than 15 months. Nothing makes David happier than client results.

He has been featured and quoted in the New York Times, Investors Business Daily, Selling Power, Sales & Marketing Management, Forbes.com, and CNBC.

David also hosted the national audio magazine of the National Speakers Association, Voices of Experience, and over 300 episodes of The Speaking Show and The Selling Show.

Kind Folks Finish First: Sales And Career Lessons Toward Success With Sam Jacobs

Salespeople often have a bad rep; they are seen as sleazy, manipulative, and, sometimes, intense in the way they deal with others. It is time to change that misconception. Sam Jacobs, the founder and CEO of Pavilion, imparts the message through the book of the same name: Kind Folks Finish First. You don’t have to be ruthless to get ahead; kindness will get you there faster. In this episode, Sam joins us to tell us more about the book and highlights, along the way, the top sales trends we have seen this 2023. He discusses a value-first approach to sales and business, overcoming the notion of treating relationships transactionally. Sam also gives great food for thought about the way we look at our careers: should you do what you love? Why do you need side hustles? For more sales tips and insights that will lead you to success, tune in to this conversation!

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Watch the episode here

Listen to the podcast here

Kind Folks Finish First: Sales And Career Lessons Toward Success With Sam Jacobs

We all know that those of us who have chosen a life in professional sales chose a business discipline that's a little more tumultuous than many others. According to Gardner and others, as we all know, the tenure of somebody who's a sales leader is now less than two years the average tenure. The average tenure of a professional salesperson is also less than two years. It's a unique profession that we've dedicated our lives to.

This episode is going to be helpful to all of us because we're talking with Sam Jacobs. He is the Founder and CEO of Pavilion, a thriving community with more than 10,000 members around the world. Sam has led revenue teams at a number of different firms, including Behavox, The Muse, Livestream, Axial and Gerson Lehrman Group. He also started a very successful podcast called The Sales Hacker Podcast.

He has written a book called Kind Folks Finish First. I'd like to share a wonderful testimonial from somebody that we respect, Daniel Pink. He has been on our show. His book, To Sell Is Human, one of our favorite sales books of all time. Here's what he writes about Sam's book, Kind Folks Finish First, “This is an excellently crafted book with a badly needed message. You don't have to be an aggressive jerk to succeed in business. In fact, if you lead with generosity and fairness, your professional life will be better off and your whole world will be plain better.”

We had a great conversation with Sam Jacobs. I'm aided in the co-hosting duties by our old friend Dave Hanley, who leads sales for AdvertiseCast. Dave has led a number of startups to very successful exits, but he lived through all of the challenges, the ups and downs of being in a sales career as well. He helps me chat with Sam. We're going to be talking about some of the key elements of Kind Folks Finish First, why Sam founded Pavilion, the value people get from the community of sales professionals, how so you need to lead with a value-first approach, and what your values are as a business professional.

We got some interesting thoughts about people in sales nowadays because of that short tenure, we all need back doors. Side hacks, being critically important, we're not entirely dependent on our employers when these changes take place. I enjoyed meeting Sam. It’s a great book. I wish I read this book or had this book when I started my sales career. You should pick it up. It’s a great conversation. I enjoyed chatting with Sam. I think you're going to enjoy this show. When you do, please like and subscribe because that matters to us. Thank you for doing so. Here's Sam Jacobs.

We've got a couple of fantastic guests that I'm going to introduce in a second. We're going to be talking about Kind Folks Finish First, a spectacular book by Sam Jacobs, who is the Founder of Pavilion. It is important for professional sales. This show exists to try and improve the lives of salespeople with education. When we get mastery of what we do, we feel better. As always, we're trying to share some strategies, processes, and tools that help all of us get better. We're going to have a great conversation because Pavilion exists to do the same thing, to help salespeople achieve their potential.

I own a company called In The Funnel. We are a group of sales coaches and consultants that help companies sell better, but I'm delighted to introduce a couple of my guests here. I'm going to first start with Dave Hanley. Many of you know that Dave is a friend of In The Funnel and a longtime client for full disclosure.

Dave is the Chief Revenue Officer of AdvertiseCast, the podcast advertising division of Libsyn. Before entering the podcast industry, Dave co-founded several successful enterprise SaaS businesses in the insurance and risk management space. He was the Cofounder of AdvertiseCast back in 2017 based on his passion for consuming great podcasts. He had great timing. The company quickly became a leader in the space as the first and largest online podcast advertising marketplace. In 2021, AdvertiseCast was acquired by Libsyn. Now Dave works in with Libsyn. Dave, welcome.

Thanks. I'm happy to be here. It’s great to meet Sam. I’m looking forward to the conversation.

Thanks for joining. I would like to introduce Sam Jacobs. He is the Founder and the CEO of Pavilion. Many of you already know about Pavilion. He launched Pavilion originally as a revenue collective in 2016, then he bootstrapped the company to $10 million ARR or Annual Recurring Revenue. Before working with Elephant Ventures, he took $25 million in funding in growth financing.

Before Pavilion, Sam spent fifteen years as a Senior Revenue Leader in VC-backed companies in New York, including Gerson Lehrman Group, Axial, and there’s an interesting story there, Livestream and Vimeo, The Muse, and Behavox. Sam's story and journey has been well articulated in the book we're going to discuss here Kind Folks Finish First. Sam lives in the West Village of Manhattan with his wife and two dogs, William and Oswald. We're all pet lovers here. Oftentimes, when we've got Dave Hanley, we can see out his window and his horses in the background. Sam, welcome to the show.

Thanks for having me. I'm a happy customer of Libsyn. I’m delighted to be here.

Sam, we're chatting a little bit about the book because I did enjoy this book. I probably read a sales book every couple of weeks for the show as part of the joy of doing it. This one touched and resonated with me on a number of different fronts. Let me throw it over to you and get a little bit of a shorter story of your journey and what led you to write this book.

Thanks for having me. I'm excited to be here.

It’s my pleasure.

I've been in New York for many years, the second time. I came back to New York to begin working and startups in 2003. From 2003 to 2018, fifteen years, I worked as a salesperson effectively and as a revenue leader in high-growth companies. What happened to me was that, as I achieved what I thought would be greater degrees of success in my professional life, I began to realize diminishing levels of happiness, enjoyment, and job security.

I worked at this one place that was super successful, GLG, for seven and a half years, and then I worked at the places that you mentioned in the bio, Axial, for four and a half years, Live Stream for 18 months, The Muse for 9 months, and Behavox for 10 months. What was happening was that my ten years were shrinking in the opposite way that I expected because when I was growing up, I thought that as you become more senior, you'll become more secure and established. You'll achieve wealth and do all that stuff. It wasn't really happening for me.

The book is about the founding of Pavilion and it was about me coming to the epiphany that I could remove myself from the way that I had thought been taught to live my career and try to, which doesn't mean I'm perfect and I don't think I'm better than anybody, embody a different set of principles and see what would happen. The book starts on Friday, the 13th of October 2017, when I was fired from The Muse. That's another part of the journey, which is that I faced a lot of failures, terminations, and a certainly relevant in an economy like the one we're in for technology.

Kind Folks Finish First: The Considerate Path to Success in Business and Life

I was driving down the New Jersey Turnpike with a dog that's now passed away, Walter, in the back seat and with my partner in the front seat. I got a message from the CEO. I was using my phone. This was before Apple CarPlay became ubiquitous in cars. I was always using my phone as a GPS and Waze. I got a little notification. I pulled over and said, “I didn't even realize you'd be out of the office. Can you come back into the office first thing on Monday?”

I remember thinking, “She's not a morning person. She's not into first thing in the morning.” I'd gotten that three-line email before and I knew immediately what was happening, which was that I was being fired. That was a moment at which I decided to embark on a different journey. That journey led me to begin to build the Pavilion in earnest. I hate to sound too cliché or too woo-woo, as my coach would say, but it was a journey of self-actualization. It was a journey that led to where I am now.

That's effectively what the book was about. Fundamentally, to cut to the chase, the book is about a different set of values that I articulate and that I would share with the audience and with people that would read it that says, “You don't have to behave in a way that you've been taught or maybe some people have been taught. It doesn't have to be a dog eat dog, ruthless competition, or zero some.”

You don't have to treat relationships transactionally. Every time you help somebody, you don't have to get an invoice back in return. You can do things for the good of helping. It's not that it'll make you feel better, but that you'll die a popper, penniless, and destitute. This is a formula for professional success. I've used this formula to build the company that I now run and to help other people do the same.

First of all, there is so much to one pack there. This is what hit me so much. You're in your car. You're driving. You think everything's okay. You've seen it many times. The chapter one's title is Fired At The Rest Stop. You've got that weekend where you're going to go through this and you know you're walking into this meeting on Monday, and then you're going to get fired. This has happened multiple times. We may have been of a generation where we thought, “The longer we do this, the more stable our roles are going to be,” and so on and so forth.

As you aptly point out in chapter two, Gardner tells us the chief revenue officer is going to last eighteen months. Now you're going to go through this whole rigmarole again. For everybody who's going to go through some tumultuous times, there is that adage that said, “It's sunny as after it's darkest. Maybe we have to go through some of these things. Any of us who've had a little more to come of success, you've had some of those challenging times as well.”

It tugged at me. I related to that so much. I had a similar type of journey in some ways somewhere. Maybe I tapped out of companies before I was going to get fired. I was pretty happy at one point in time to tell people, “If I didn't like something, I just walked out of it.” In some sense, I was thinking, “I'm not going to be successful here. I'm going to tap out before they tap out.” Going through this journey, at some point in time, you get quite frustrated and go, “There's got to be a better way,” and leading to this abundance mindset.

Start to say, “It's not about me. It's not about what I'm making. Let's figure out how we put a little kindness into the world here. The fact that abundance begets abundance.” Before this journey, I thought there was some great wisdom in here about doing something you love, and we have a little shared interest. I'm back in my bar band again after years and years. We played at a historic club in Toronto on a Friday night. We went on at 10:00 PM and finished at about 12:15.

In the middle of that show, I realized my bedtime is 10:00 PM and there's a reason for that. I'm a drummer. I could feel my coordination leaving me pretty quickly as I was going through this gig. What did you do before you went into the world? What did it teach you about finding that idea about doing something you love?

As you alluded, I've got a background in music as well. I ran a record label out of school in the late ‘90s. We set up on a horse farm in the middle of Virginia. We thought we were going to start a commune. A bunch of people would come through the commune and record. I reference a bunch of like artists' collectives that people might know about from my indie rock days. What I realized in starting that record label was that, first of all, the music industry is like a pretty bad business. Also, when people say, “Do what you love,” it's not always the most useful advice.

There are a couple of reasons for that. The first reason is I believe in the power of experience. I'm not trying to stifle anybody's fulfillment or actualization. If you're whatever age you are, if you want to go out and start your own business or do your own thing, I support you as I did. I will tell you that the first thing is that I didn't know what I loved when I was entering the workforce. It takes some reps and experience. That's thing number one.

Thing number two is I find that people miscategorize what they “love.” Sometimes they identify the mission of the organization with the jobs to be done in that organization. They conflict with those two things. They say, “I love Lululemon. I want to work for Lululemon as a senior controller.” Being a senior controller in Lululemon doesn't mean you're doing yoga all day and hobnobbing with other celebrities who also love Lululemon. It means that you're looking at financial statements.

People miscategorize what they “love” and identify the mission of the organization with the jobs to be done in that organization and conflate those two things.

The final thing and most important thing is that if we're thinking about professional success, there's a Venn diagram. There are three things that are involved in that Venn diagram. There's what people are good, what they're interested in or what they love, and most importantly, there's where the market is moving. People underestimate or undervalue where the market is moving and what they're good at. They overvalue what they're interested in. I was interested in recording music. I love recording music. I've got a bunch of albums on Spotify. That doesn't mean that I should be a professional musician. That might mean that that's a fun hobby for me.

I needed to look at the fact that I was starting a record label at the rise of Mp3.com. Maybe recorded music is coming back a little bit, but fundamentally, there were about two decades there when the entire economy in the music industry fell apart. It was not a good time to start a record label. That doesn't make me less creative or less artistic. That's the reality of the world. The last thing I'll say in my long-winded way is that people don't distill the daily activities of a function. They put a label on the broad definition of the function. They say, “I don't like finance. I don't like sales.” Let's talk about salespeople. “I like sales,” or, “I would never do sales.”

What is sales? Sales is talking to people, being curious about them, figuring out what their problems are, and then figuring out if your product-solution service might be able to help that person solve that problem. That's one part of what sales is. Another part is, “Do you like long project-based work? You shouldn't work as an SMB seller with 30 days of sales cycles. Do you like instant gratification? Do you like to know that I do something, and very soon thereafter, I see the result from it?” Sales might be a good career option for you.

I find that a long-winded way of simply saying to an early career person, “Do what you love,” is not super helpful. I find that giving people a framework for how to think about it does a couple of things. One of them is it manages their expectations a little bit because the other thing that happens that is happening now with quiet quitting and employee disengagement is that everybody's been misled about the nature of work to a certain extent. Everybody's like, “Why do I not feel like I'm at church and the pastor is singing?” Sometimes, it's just work. Sometimes, that's what it is. It's not that every moment is going to be an epiphany when all you say is, “Do what you love.” It's not super helpful, when you're thinking about, “How do I practically build a career over decades as opposed to over months?”

Your friend, Dan Pink, has been on our show. One of my favorite books of all time, in addition to yours, is To Sell Is Human. It came around at the same time that we started this business many years ago. Dan Pink didn't come from a background in sales, but on the show, I asked him, “Why'd you write this book about sales if you had no background in sales?” He said there was such a disconnect with everybody that he knew in professional sales, but the stereotype of someone in sales as a pitcher, used car salesman, and all this. Everybody knew in professional sales were some of the smartest, most intellectually curious problem-solving people he knew out there.

That book is like a masterclass or an MBA for sales because his research is thorough, but he was trying to find ou. Of the 8 and 9 people in the US who aren't in professional sales, 1 in 9 are and 8 in 9 aren't. What percentage of their day do they spend trying to persuade somebody else to their point of view? It turns out it's 39% of the day. All half of every day, they're trying to convince somebody else to their point of view. Everybody's got this default, “I'm not in sales.”

We hear that often when we're training service technicians or something of that age, “I'm not in sales. I could never sell anybody anything.” It’s something's exactly like what you said. It's helping somebody achieve a better future and business outcome. At the end, I asked Dan, “Where do you see sales going?” He netted it out as saying, “Nowadays, professional B2B sales is management consulting. Anything that isn't that will be taken care of by automation or AI, etc., but true sales is management consulting.” Any of this resonate for you, Mr. Hanley?

I'm thinking about my background and how it relates. I went to school and I thought I was going to get into Finance. I decided after my second-year Accounting course that I hated it. I stumbled into more entrepreneurship. What you realize when you want to start a business and work on a new venture is that a large percentage of what you're doing is sales.

The key is being curious. What happened to my career is if you don't know what you're doing, which I didn't, and I got into an industry that I knew nothing about, I was, by nature, asking a lot of questions because I wanted to learn and curious. That came across as, “This is a great person to talk to. They're interested in our business, and they care about how they can help us.” For the most part, I was trying to learn, but what a lot of salespeople who are new to selling don't realize is that you don't show up and pitch. You have to ask questions, solve a problem, and communicate whether or not you can help add value and solve that problem.

There's a big conference called Collision. It is a technology startup conference. There are 36,000 people in Downtown Toronto. The energy and enthusiasm of walking around a conference like that is spectacular. There are a lot of startups. They've said it up. Startups, mid-tie, and growth organizations and lots of VC. Everybody gets a seat at the table. It's an interesting setup. I probably chatted with twenty startups going through and having conversations.

Not a single person in any of those things asks me a question. The best two questions I got I was somebody said, “What brought you to the conference?” Many said, “Tell me about your business.” I'm not joking. This was the guy taking my order in the coffee truck outside of the conference. This is the only person at the conference who asked me anything.

That makes me upset.

It gave us an opportunity when we were walking around. After I'd have these conversations with these startup founders, I'd share that and say, “Here are a couple of things to do next time if you're open to it. You might want to think about this question and get someone talking to you, plus you'll enjoy it more.” I could see when they were doing their pitch for the twentieth time that day, they were tired. I thought, “Ask a question. Get involved in an engaged conversation.”

I'm going to give a shout-out to the guy taking orders from Fleet Coffee when I was getting my cappuccino. Sam, tell us about the rest stop. Now, we've had this epiphany. It leads to 2016 or 2017. You'd always had a dinner club or a networking club for other people in your role. How does that evolve into what is now, the opportunity with First Revenue Collective and Pavilion? Tell us a little bit about that journey.

The first thing I would say is it began without any sense of expectation. There was either one in Toronto that David was putting together on sales or something like that. There was one in the Chicago Sales Assembly. My point is I didn't think that this was a venture-scale business. This was not some world-dominating master plan.

This was me saying, “I'm not solving backward,” from, “I need to have dominated the world by X, Y, Z year.” It is me saying, “I'm going to check out of the Merry-Go-Round or the carousel that I'm on, and I'm going to build something that I care about and that I love. I'm not going to worry too much about anything other than Maslow's hierarchy of needs. Is there going to be a roof over my head? Can I pay rent? Can I do what I love, which is helping people and connecting people so that they can achieve their career outcome?”

I got fired. It was the fall of 2017. I've written about this on LinkedIn. I said, “I can't be dependent for all of my income on one source of revenue anymore If I'm going to work for somebody else. I need ‘side hustles.’ The world is too uncertain for me to put all of my eggs in a basket that somebody else totally controls and can decide at any moment that I'm no longer suitable for the basket. I'm going to build a consulting business. I'm going to take this dinner club, try and monetize it. I'm not trying to monetize it so that I can be on the cover of Time Magazine. I'm not trying to be Elon Musk. I'm just trying to do something that I care and am passionate about that frankly can't be taken from me.”

That was the origin of it. From there, there were 22 people then. I said, “Everybody, we're going to charge dues on January 1, 2018. Who's in?” 20 out of 22 people said, “I'm in. I’m not sure what I'm paying for, but I'm up for it,” and then we grew from there. People started hearing about what we were doing all over the world and people from other cities started reaching out now. Why did they?

One thing I think is sometimes people don't know why they're successful, but if I had to guess, there was a point of view behind the community. It wasn't networking for its own sake. It was, “What do we believe about the world? How should we align and what do we still believe about the world to this day?” We believe a couple of things. First of all, there has been a little bit of undue influence focused on CEOs and investors and not enough care is taken for the people that run and operate those companies.

As a consequence of that, we still teach people how to negotiate and what they're entitled to when it comes to executive compensation. What I want for everybody is that you don't have to be this founder or CEO to lead a meaningful and fulfilling life. There's a role for an executive operator at a company, but that role needs to be renegotiated because the old deal wasn't working very well. That was a big part of what attracted people to the community, which is that there was a latent point of view that was articulated.

You don't have to be this founder or CEO to lead a meaningful and fulfilling life.

When we do worse in our Incarnation, which is 10,000 people, it's because we're not doing enough to articulate that point of view that we're not clear enough in why we exist and what we stand for. That was one of the big reasons why people begin to come to us. We grew over the course of 2018. I worked one more place full-time, and then I got fired. I was having breakfast with a mentor and I said, “I'm going to try and work on Pavilion full-time, but if it doesn't work, I'll go back to being a CRO,” and he smiled and said, “I think we've tried that experiment at this point.” I won't say the rest was history. It's been a lot of stops and starts, mistakes, and great outcomes.

We're in the middle of our next phase of evolution, which is about getting back to our roots and re-embracing the ideas that got us here in the first place, which is a point of view that we exist for the individual operator first and foremost. We want to train that person not just to be a good employee but to be an actualized and self-realized human. That might mean consulting and advisory business like you've done. We want to teach people how to have a career. A career is not you work one place for twenty years anymore. It's a series of gigs, advisory roles, and consulting jobs. It is the combination of all of those things in the accumulation of all those experiences over time, which hopefully lead to wealth, impact, better relationships with your partners, and that whole thing.

The path there is always, “Are you enjoying what you're doing?” You talk a lot about you weren't fulfilled in many of the roles leading up to it. You have this epiphany. I've always felt the same way that, finally, when I did this, it felt like this is what I was meant to do, but I needed that corporate journey for twenty years to teach me something that was valuable. I needed that experience. I needed to do massive and smaller deals. I needed to run big teams and small teams. I needed to learn something that was valuable if I could add my own unique ability there.

We were talking that there a little bit about the side hustle and consulting. Chapter seven is Every Crisis Is An Opportunity. You do talk about this. This is very helpful for folks reading this, which is the rules of compensation. There's some great coaching in this book as to, “If you're negotiating that next deal, what should you think about?” You have five things that you're entitled to when it comes to compensation. 1) Due diligence. Do your investigation number. 2) Aligned compensation, liquidity by the way. I'm getting options, “Am I ever going to get them out?” We'll talk about double triggers a little later on.

Negotiate the severance upfront and think about that, which is one of the ways you got a little breathing space to get into this, and then consult, talking about how you build something on the side for you that no matter what, you're allowed to continue on doing. With In The Funnel, we work with a lot of people who do exactly that. They may have been a client of ours at some point, like Dave, then over time, they start to work with us because they've got their own consulting businesses on the side. It's a great model for them. It's a fantastic model for us.

Here's the other thing I love reading that chapter about negotiation. Understand what you'd like and then what you're willing to agree with. Most people don't understand how to negotiate. You underlined this a few times. Don't bluff. I don't know where we were taught to negotiate and being tough, mean, and banging at the table. At one point in time, we negotiated a $1 billion deal. I've never been scared in my life, but the one thing I knew I wasn't going to do was lie at the table. I've never been over my head ever. When we're negotiating it, the only thing I had was my character and integrity. Don't make a commitment you can't adhere to. Don't bluff. That is not a TV show. That's very good coaching for everybody out there. Comments, Mr. Hanley?

Mark and I were talking about this piece of the book before. It took me back. I've worked with Mark for many years. I don't remember how many years it has been. One of the original big learnings I had from Mark was on negotiation. You're trying to work a big deal and we said, “The price is X,” and the client is looking for Y. Trying to find that win-win and what's important.

It is asking the question saying, “We gave you a price of $100,000. You want it for $80,000. What else is important? Is it the timing? Can you wait? Do you want it now? What other levers can we pull to get something that works for both of us? Can you pay a little bit upfront as opposed to the back end?” It is asking those questions to figure out how we can negotiate and come to an agreement. We're not lying, bluffing, or throwing red herrings. It's more of asking the right questions and trying to find something that works for both parties.

Make the pie bigger. It's not about a bigger piece of the pie. It is trying to think about, “How do we make the pie bigger?” There's got be that trust and authenticity to have that conversation. I don't know if the book answers directly, but we have a conversation and it seems you are the wisest, most balanced person out there. What was happening that you were getting dismissed frequently or why, in your view, are CRO only lasting eighteen months in their job? Pavilion must see a ton of this with the on-the-bench and so on and so forth. What's going on that the tenure of this role as short?

Let's speak about me first. I don't think I'm blameless at all. I can be a difficult person to work with. When you're a C-level executive working for CEO, what you have to understand fundamentally is that it's their company. They can call it a partnership. You can call it the first team. You can read The Five Dysfunctions Of A Team by Pat Lencioni. It is their company. You work in service to them.

I always joke about where if you're in a romantic relationship with somebody else, they yell at you, but they don't get over grievances with you and they don't leave. They seem to want us to stay. That was me. That was being disgruntled and saying, “I could do it better. If I could do better, I should go do it better because it's their company.” This idea of, “If I was being frustrated with the potential of an opportunity without acknowledging the reality of it, that's my fault. That's not anybody else's problem. Those idiots won't listen to me. That's my problem and not their problem.” That's how I was. I've always felt like I was probably a better startup CEO than I was a startup employee, but I never had anything that I was working on of any size or scale. Now, thank God, I do. Lo and behold, I haven't been fired since 2016 when I got this thing off the ground. That's a great thing.

Let's speak more broadly to the tenure of a CRO. There are a lot of factors at play. I don't think that there's an enemy. There's no bad person or good person in this equation. The first thing is we're working in a world that is changing more rapidly by the day. That's true. We're talking about AI. It's not that AI was invented with ChatGPT, but this hype cycle was created in November 2022. It already feels like we've been talking about it forever. The world is changing more quickly than it used to be.

We're working in a world that is changing more rapidly by the day.

Many of us have watched Mad Men, where Don Draper goes to launch, has three martinis, and then goes to take a nap. That's fine because nothing happens that quickly. They had telephones. They didn't have pager or iPhones. The pace of business was slower. That's one thing I think. The second thing I think is if we're going to work at high-growth companies in particular, we do have to acknowledge that $2 million business that grows to $6 million or $8 million over two years, and this is true for us, we went from $4 million to $17 million over two years, the things that I need an executive to do at $4 million company are different things. It's a different company.

The only reason it's become clear to all of us is because we are choosing to work in these high-growth inorganic environments, but in the old days, that was seen as extraordinary growth. It wasn't true. Things don't grow in 200%. It was technology that enabled this. The last thing I'll say, which is part of the work frankly of Pavilion, is community unto itself is not that interesting. Community with a point of view is more interesting because there's something to rally around.

There's a point of view that founders, CEOs and investors don't know how to make money. In fact, most CRO’s don't know how to make money. What do I mean by that? This is related to what you said about the Bill of Rights about those five things. The second thing that you mentioned was the line compensation. There's this world that we've lived in for a long time, which is the senior sales leader, the chief revenue officer, and the VP of sales should be the highest-paid person at the company. That's because the salesperson brings in all the money, but that's not true.

That's not where money comes from. Money comes from the product, marketing sales, customer success, and partnerships all being in alignment. If you want to add more money, you need happy customers. You get happy customers from a good product. You get people aware of your product because you have great marketing.

This whole idea that, “We're going to hire the savior salesperson that used to work at Salesforce, Adobe, or Oracle. They're going to come in, transform our business, and we're going to pay that person $700,000 a year, but we're going to pay him $350,000 base and $350,000 commission. When that doesn't happen because it's not the senior sales leader, we're going to fire that person. We tried to hire the savior. The savior didn't work, back to the drawing board. Let's find the next savior.”

In fact, the process of building long-term sustainable businesses is alignment across the go-to-market organization, which is another perspective that Pavilion shares. That's part of the education that I'm on. Prior to this session, I was teaching the first session of Pavilion's CRO school. We were developing a theory of enterprise value. What is that about? That is about, “Let's set a foundation for how money gets made.” It's not hiring the salesperson with lots and lots of meetings and no process can still make money for the business.

The salesperson with the absolute best medic process and everything is qualified and put into Salesforce, but if there are no meetings at all, that person will get fired. That is the line on how value is created, but to the point of the eighteen months, lots of people aren't aligned on how value is created. Investors, CEOs and founders, particularly those who come from technical and product backgrounds, don't know what's supposed to happen. They think, “I hire a salesperson and money comes out a month later,” and they understand, “Not really.”

That's a great explanation. We've asked that question 50 times on this show. Does that resonate for you, Dave?

I was thinking about how it relates to what you talk about a lot. Parachute in this amazing salesperson and they can make it rain, but there has to be alignment in terms of going back to the core of what you like to talk about, which is the value proposition of the business. What problems do you solve? All that needs to be throughout every aspect of the organization. Marketing needs to talk to that. Customer service needs to know that. That needs to emanate from them as well. A lot of times, somebody, maybe like the person who's running the business, doesn't even know how to articulate their value proposition, but they expect a salesperson to come in, go out there, and make magic. That's not going to happen.

I created this stuff for the CEO and founders that I advise. I said, “You got to invest in marketing before sales. I don't mean you hire all marketing before you hire a single salesperson, but the function needs to be excellent.” They say, “I got it. I've been doing some research on marketing and I had a director of demand gen because I'm doing what you said, and nothing's happening.” I'm like, “Demand gen is FedEx, logistics, and putting a message in front of a certain group of people at a certain time so that they'll take action. What's the message? What are you putting in the container?” He is like, “What do you mean what's the message?” “Our thing is great and that everybody else is for it.”

That's features and functions.

They come out of meetings where it falls down and they go, “She didn't get it.” In front of a client, they can't articulate it. The client doesn't even understand what they're talking about. It's gibberish. They pointed the client going, “She didn't get it. She's not right for us.” The hard work is boiling the old Albert Einstein. If you can't explain it simply, you don't understand it well enough.

If somebody works with your company, “What's unique and different about you?” “Application development shops or 100,000 different application development shops.” How do these people differentiate? It's all the same. The hard work is in capturing this to enable the sales organization to be successful or enable the marketing team. This is hard work. It's not self-evident work.

The last thing I'll say is you give that speech to them and they say, “How long does that take to create the right message?” You're like, “It takes a long time. I don't have a long time. I sold these investors on the promise of proft this year, but I think I'm going to go hire more salespeople.”

That's exactly what everybody's done with the VC money until they're worn anymore, or until you couldn't do it anymore and the prices kept going up, and the model doesn't work. I should point the finger to In The Funnel here. We're in the same boat as everybody else. We came up with value proposition messaging many years ago. It came from me, and we thought it worked, it would go through the organization, and then it became this mantra that everybody was repeating. We were teaching it in our CRO school one day.

Somebody put up their hand and said, “That's not your value proposition because it used to be, ‘We help companies sell better. Companies come to us when revenue growth is stagnated or the sales team is underperforming.’” Our first 50 clients came to us because of that, then we're in this workshop with 60 people in 15 hands go up and go, “I saw why we're here. Our sales team is killing it, but we want to keep them. Your value proposition is wrong.” They were absolutely right. We're coaching people like Dave Hanley, killing it, exiting 2 and 3 times. He's not in trouble at all. He just wants to keep getting better.

Unfortunately, not everybody has clients that'll tell them that. They'll give them that feedback.

There's not a one-time thing and you are refining it after 100 client meetings. It's an ongoing process. It's not complicated. It's not easy. None of this is an easy fix. What would you coach or counsel? We have our pal, Frank Cespedes, from Harvard. You probably know Frank. He hass written 7 or 8 books. The latest one is called Sales Management That Works. In that book, he talks about, “If you graduate college or university today, there's a 50% chance 1 in 2 of those people will have some role in professional sales in their lifetime.” That's what the stats seem to be. He's pulled up the stats.

What would you tell somebody graduating in college or university? Where would they go? When I did it, there were places to get the world's best sales education. I could go to Xerox. I did go to Kodak. That's where I started. I was in a different country at Sales University for 90 days or 4 months before I ever saw a client or IBM. What does somebody do now in your view? Where do they go? Pavilion?

I think so. The truth of the matter is that Pavilion is more an executive community than an entry-level community. You should come to Pavilion if you want to learn how to be an executive. We have this concept of associate and analyst memberships, but those memberships are focused on education. It's a hard question nowadays. If you'd asked me this before, I’d still probably give the same answer that you gave, “Go to work at Oracle, ADP, Paychex, Xerox, or a company that has the resources and infrastructure to train you.” In the same way that before you should go work for a hedge fund, you probably work at Morgan Stanley, Goldman Sachs, Bank of America, or Merrill Lynch so that you can get trained in the core foundations of your craft before you move on to a higher level functions.

I'd still say that, but I'm not sure that those people are hiring. The other thing I would caution is that the role of the sales development rep used to be the perfect entry-level role. There are still people who are hiring SDRs, but I do think that that role is challenged more than it has been in the past because the rote automation of all of these technologies that are creating millions of emails and trillions of text messages is diminishing people's attention span and their ability to engage.

That said, I would invest in your own education outside of a core company providing for it. That might be Pavilion, SV Academy or Sales Assembly, but it's something that gives you some exposure. Fundamentally, now more than ever, your career is your responsibility. Nobody is going to be looking out for you in the way that you might hope or expect.

Now more than ever, your career is your responsibility. Nobody is really going to be looking out for you in the way that you might hope or expect.

It's a very good advice. You've got to take control of your own career now. It’s a different one. There are lots of opportunity, but I think that's sage advice. Dave, any final questions for Sam?

Mark and I were chatting about one of the aspects of the book that we already touched on a little bit with compensation. I am wondering if you had any advice for somebody who is a founder that is leading a business and bringing in a sales function. What advice do you give to them on how they should craft a sales compensation plan for a team that aligns properly with what the organization is trying to do? I've been in that situation a few times. It's hard to find the perfect model. I’m curious about your thoughts on that.

A couple of thoughts, the first is that before you hire someone else to sell, you better have done it yourself. That's a prerequisite. It's not, “I have this great product. Go sell it.” You have to have done it. I don't care what you think about your sales capabilities. If you can't sell it, they definitely can't sell it. You have a founder and CEO on your business card or email signature and they don't. You should get between 5 to 20 clients on your own as a founder before you go out and look to invest in the sales function.

The next thing I would say is if you want to hire your first 1 or 2 salespeople, what should be their comp plan? Quota implies predictability. If you don't have predictability, then I don't think we should be talking about quotas. What we want to do is define a very generous commission structure. First, you show that you can sell it, then you need to show somebody other than you can sell it.

You're not going to be able to pay that person very much in base salary. Maybe we give them 20% of every sale. Maybe we give them a year. If they make too much money and we feel annoyed that they need so much money, let's consider that a great success. That would have been way better if they made too much money than not enough.

From there, once we have a little bit of predictability, then we can start to design some comp structure. At scale, 20% of bookings does not work. There are a lot of companies that were paying 15% or 20%. The math of that in an interest rate environment that is normalized as opposed to where there's free money does not work. The number that tends to work better than others is 10%. You need to be able to show that 10% plus base salary equals an amount of money that can pay that person's bills. The benchmarks, which many people know but are roughly 10 times base, should be the quota or 4 times OTE. If you're an account executive and your OTE or On-Target Earnings is $150,000 and that $75,000 base and $75,000 commission, then your quota should be $750,000.

Those are great metrics take away. Those are very helpful.

The main thing I would say is too many people are like, “We're building a revenue model to get to $2 million in IRR.” I'm like, “Below $2 million IRR, the revenue model is interesting, but we should be thinking about milestones the business needs to hit that work towards predictability as opposed to working backward from the spreadsheet.”

The first thing I get into would be your specific curriculum for the CRO school. I'd be very interested in that, given what we do. There are lots of great stuff to share there. We've had a good taste Of Kind Folks Finish First. One of the things that I didn't get when I started in professional sales was a sense of self-esteem or pleasure for being in professional sales. When I started, it felt like a default because at that point in time, I was done with MBA, my friends were in investment banking, and they were lawyers. It felt like I took the easy route until I realized it was the best job ever. I wish I had this book many years ago. You've got it now, Kind Folks Finish First: The Considerate Path To Success In Business And Life, Sam Jacobs with Kerri Linsenbigler. Sam, how do people learn more about you and Pavilion?

You can email me at Sam@JoinPavilion.com. You can follow me on LinkedIn, where some other people have chosen to do that. You can go to JoinPavilion.com.

Dave, how do people find you?

I'm in the podcast business, both on podcast hosting and technology, as well as advertising. The hosting company is called Libsyn.com and then the advertising side is AdvertiseCast.com. Anybody who is interested can check that out.

First of all, thank you very much for joining and taking time out of your valuable time. There's been huge value to the audience. I want to thank the readers. We run this show to try and help improve the performance and professionalism of the B2B sales team and improve the lives of professional salespeople. That's what we're trying to do here. I know there are things we can do to improve. You're the ones who tell me that. We love constructive criticism.

If you like this show, please like and subscribe. That matters to us. If there are things that we can do to elevate this show and make it more valuable to you, please let me know. My personal email is MarkCox@InTheFunnel.com. We love constructive criticism. Please be direct. Anybody who sends us a note gets a nice note back from us. We'll respond to every piece of advice. Thank you for joining. We'll see you next episode. Sam and Dave, thank you so much for joining. We'll see both of you again soon, I hope.

Thank you so much for having me. Dave, it’s great to meet you. Take care.

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About Sam Jacobs

TSW 80 | Kind Folks Finish First

Sam Jacobs is the Founder & CEO of Pavilion. He launched Pavilion as Revenue Collective in 2016 and bootstrapped the company to $10M in ARR before taking on a $25M growth financing round in early 2021.

His early vision of Pavilion was about more than creating a community to help salespeople excel at work. He wanted to turn centuries of so-called business wisdom on its head. Sam believed in a world where reciprocity, generosity, and kindness could be good for business—a world where self-interest was replaced with community and everyone could get ahead.

Pavilion has proven Sam’s hypothesis many times over, growing into a $200 million professional development company that helps its members get through giving. Prior to Pavilion, Sam spent 15 years as a senior revenue leader at VC-backed companies in the New York area including Gerson Lehrman Group, Axial, Livestream/Vimeo, The Muse, and Behavox.