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!
---
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.
Important Links
Daniel Pink – Past Episode
LinkedIn – Sam Jacobs
About Sam Jacobs
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.