Sam Jacobs, Founder of Revenue Collective | A Community For Sales & Marketing Executives

Sam Jacobs is one of the leading figures in revenue development at high-growth companies around the world, and is recognized as one of the top go-to-market executives in the country. He is the Founder of Revenue Collective, the leading global community for customer-facing executives, with more than 2,000 members around the world. Sam also hosts the Sales Hacker Podcast, which generates roughly 40,000 downloads per month and has featured guests ranging from Dan Pink to Mark Roberge, and many more.
Prior to Revenue Collective, Sam spent 15 years leading go-to-market teams in the greater New York City area, including serving as Chief Revenue Officer of Behavox and The Muse, Senior Vice President of Sales and Marketing for Livestream (acquired by Vimeo/IAC in 2017), Senior Vice President of Sales and Business Development at Axial, and Managing Director at Gerson Lehrman Group.
He’s helped businesses scale revenue anywhere from $0 to just shy of $300M, and has been instrumental in the raise of more than $1B in institutional capital across various companies. Sam graduated with degrees in Commerce and Economics from the University of Virginia. He lives in the West Village of New York City with his wife and two mostly blind, old dogs.
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Thanks again for joining me. Today I am sitting down with Sam Jacobs, who is the founder of Revenue Collective Now Sam for 15, 16 plus years. He's worked with a variety of companies as senior sales, executive leadership, he's up company scale from $0 in revenue to over $300 million. He has significant operational expertise, sales expertise, emphasis on go-to-market strategy. He's worked in a variety of SaaS and recurring revenue businesses, including being a commercial operator at GLG, live stream slash Vimeo, the Muse and Behavocs. Now what he's working on is the Revenue Collective, which was started as a 100 member group January 2019, fast forward to 2020, there's over 1,400 and growing, it's an invite only global community of sales, marketing, revenue leaders. He's also the host of the sales hacker podcast, which has over 2,500 downloads, so he's going to put me on the spot now and make sure that I'm asking good questions and whatnot, so I appreciate you joining me. I think that what you're doing is incredible. I don't think there's a lot of people doing similar types of invite only for revenue executives, so I'm curious what your background is like, how you came to what you're working on today, why it's important and all of that, so I appreciate you sitting down. Yeah, well, thanks for having me and I'm happy to be here, so yeah, and just a few stats just for the audience, things are bigger than that, and make you indicate it, which is totally, which is great, so Revenue Collective is actually just around 3,000 global members at this point. Oh. We're, oh, it's okay, we're in probably over 100 cities all over the world, we got started in New York in 2016 and I can talk all about that, and then the sales hacker podcast actually gets about 40,000 downloads a month, so I've been doing that for a couple of years, but my background is I've been originally, I grew up overseas, my parents were in the Foreign Service for the US government, for the State Department, and then I came back and went to college at the University of Virginia, came out of college and undergrad in 1999, it was the first.com boom, and I moved up to New York to do investment banking, wasn't really into that very much, felt a little too corporate for me, so I started a record label, that record label was not successful, and I call it exercises and poverty and humility, and then I came back to New York in 2003, and that was really when my career as sort of what I am today began, and that's when I started a company that you mentioned, called GLG, Gerson Lamar Group, and that company was about 25 million in revenue when I joined, and I basically came in at the ground floor, there weren't even job descriptions for most of the things that we were doing, but I ended up running their global customer service organization, customer success, my title was Managing Director of Research Management, but really what that meant was taking care of all of our clients and making sure that they were happy, we went from about 25 million in revenue to 300 million in revenue over the seven and a half years I was there, and that was really a rocket ship, the company was incredibly profitable, paid out, it was very shareholder friendly, and all of the people that had options or equity were able to participate, and it was great, paid out lots of dividends, and really made sure that the people that were investing in the company saw a return, which was incredible, and I came out of GLG in 2010, and for the last 10 years, prior to a revenue collective was leading and chief revenue officer type person for early stage companies, primarily Series A and Series B companies, although it varies based on the company, but a couple of things were happening, particularly the last 10 years, so the first thing was that, as I mentioned, I worked at GLG for seven and a half years, I then worked at Axial, which is a venture backed business in New York, focusing on the private equity industry for four and a half years, I then worked at livestream for two years, I then worked at the muses to revenue officer for nine months, and I worked at Behavocs for 10 months, and so if you're plotting those points on a graph for average tenure, you can see that it went from seven and a half years to 10 months over the course of five jobs, and so that was an issue for me, and that was a problem, both for my career, but what I realized was that it wasn't just me that this was happening to, it was happening to a lot of different people, and when we did the research, we realized that the average tenure for somebody in a sales or marketing leadership position at a high growth company is just 17 months at this point, so on average, and I talked to lots of people that have worked places for 10, 15, 20 years, but on average, people are leaving jobs under a year and a half, while the other thing that's happened over the last 10 years is just that the way that people go to market, the way that companies need to generate revenue, obviously changes all the time, and it, and new technology, new tech stacks, new functions, the SDR function was actually a rather new function 10 years ago, and the sales development rep function, and now it's not clear where that role should sit, whether it should report to marketing or to sales, the definition of success for marketing was very different 10 years ago, two years ago I didn't know what intent data was, and I was trained that every piece of content that a company created need to live behind a landing page where you captured an email address. Now in 2020, the idea is that landing pages and email captures over, or at least in decline, and much more fashionable to put cookies on people's browsers and just follow them all over the internet, and then you know when they're in market, my friend Latinaco and at the chief marketing officer's sixth sense calls that the dark funnel. So the point is that two things have happened, our tenure has shrunk, and we're in the middle of COVID as we record this, so that's even more prominent now, while the job becomes harder, and when I looked across at the communities that existed to, basically, the question of how I was going to navigate and negotiate my career over the next 10 to 20 to 25 years, I didn't have an answer for it, and I was making it up as I went along, and there wasn't a clear answer for how to become a CRO, there wasn't a clear answer for how to negotiate for CRO, there wasn't a clear answer for what a CRO should be paid, or what you should negotiate for, or whether you should just accept every deal as it's presented. So that, and I looked at like, well, how was I going to do that? I didn't have an answer, and so what I started to do was put together a dinner club for that met every quarter in New York, that we called the New York Revenue Coactive, and the point of it was just me and my friends sharing best practices and ideas and getting together to help each other and support each other. And the reason that, you know, and I never thought that it would be a company at all, I just was doing it because I needed it, you know, the classic founder as the customer story, I just needed somebody to talk to, you know, so we started doing that, and then, you know, I hate to say one thing led to another, but one thing led to another, the thing that most surprised me was that I assumed that some kind of sales executive club existed already in every city, in the country or in the world. And the reality is, it didn't, it didn't exist. And so this idea of a platform and a community that really it took, the vision took shape over the course of the last couple of years, but a community where people can specifically go to manage and negotiate and navigate their career, not just be better, you know, I see a lot of communities talk about the profession of sales, you know, and that's fine or the profession of marketing. I'm interested in those professions, obviously, because that's my background, but I'm much more interested in the human beings behind those professions. And revenue coactive exists and I can talk about how why that's significant or because because it does exist in contrast to other communities that are not focused in quite the same way on the individual human being. That's what that's what our focus is. Our focus is we want to take every person that the member of revenue collective and we want to help them achieve their potential. And however they define that potential, however that means to them, we want to put the tools and the answers to the test and the guidebook and the handbook and the playbook and whatever else you want to say. But we want to put the framework in place for people to more confidently navigate their careers so that you can achieve whatever it is that you feel is inside you that needs to be achieved. And that's, you know, so that's my background. That's my origin story. I appreciate it. And it makes a lot of sense and when you speak through why revenue collective has taken hold, it's like common sense is in common. So you have a role that's ever changing. You have a commercial landscape that's ever changing. Ten years are getting shorter environments are more difficult yet you don't have a support group that actually focuses on an individual's career. Now I'm curious in your opinion at least, why was something like this or yeah, why was something like this not created to date? What is out there that revenue collective is in contrast to? Yeah, it's a great question. The reason, I think there's probably a variety of different reasons. The perspective, you know, the persona, my persona, sits in contrast to a couple of things. The first is that most of the time, you know, the celebrities in the startup ecosystem are not you and me, Scott. They're not, they're not the operators. There's two celebrities, two celebrity types, right? They are investors and founders and those are the heroes and I think that most communities grew up either in specific subservience or in indirect field to those to those stewards to those personas, right? So VISTA equity partners, very famous private equity firm, one of the best SaaS investors over the last 20 years. They do a CMO, they have a CMO community. What's the what's the underlying tension there? The underlying tension is that you have to be a CMO of a VISTA company and at the minute that you're not the CMO of VISTA company, you are no longer of meaningful interest to them. Now, they might, they might present as if but but there's a conflict of interest because that is not about your career. That is about your ability to serve VISTA's limited partners to be, to be direct. I remember when I was at Axial and I left Axial and Axial was a portfolio company of first-round capital, which is one of the famous early-stage investors, seed-stage investors, they aspire to be the first-round of capital into a lot of companies all over the country and the world. And they have a very famous, they have first-round review, they put a lot of money into their platform, they would call it a platform and their content. And I remember that I was a member of their community while I was at Axial and when I left Axial, my username and password no longer worked and they were no longer interested in having me be part of their community. So, thing number one is that communities have sprung up but they have sprung up to serve ulterior motives and there haven't and that is so that's kind of one thing which is that it's either that or the business model is conflicted so what does that mean? That means that there are other communities but most people maybe have some, they have some self-consciousness about charging and then maybe they think that all communities should be free. I do not think that revenue collective is a for-profit company that people pay dues to. So, if I was going to do it for free and I wanted to make money, what would I need to do? Well, like they say, if you're not if you're not paying money and you're wondering what the product is, the likelihood is that you're the product. And so, all of these other communities, yes they're free but the way that but they all aspire to generate revenue, all of the people that run these communities obviously are passionate about them and want to make money. So, how do you make money in a free community? Well, you sell, first of all, you sell sponsorships and the way that you sell sponsorships because it's free is that you have to promise the sponsor because they are your master. The people that pay the bills are ultimately your master. And so, you have to promise to them that you're going to build this big audience as possible. That's what they care about. So, you're going to let in as many people as possible. And you don't have the you don't have the luxury of cultivating a career in that community. You can't, I mean, look at LinkedIn, right? LinkedIn, the purpose of LinkedIn is that every person is on it. So, what happens when every person is on it? Well, there's people that you respect that have meaningful insights and relevant insights and they're drowned out by the people that have the time to post on there all the time and really work their personal brand. And so, you go on LinkedIn and, you know, maybe you can learn something and I actually don't have, you know, a problem with LinkedIn. I do learn things from LinkedIn. But I'm the product. I know that I'm the product. And I think that that's another reason that revenue collective exists because we don't let everybody join, right? So, we don't we don't let investors join. We don't let founders join. We don't let executive search firms join. And we do let some consultants join, but most large-scale consulting firms we do not let join. And that means that when you join and when you pay your monthly dues or annual dues, you know that it's a curated community and you know that you're not the product because you're paying. But the product is what you're paying for, which is the value that we that we aspire to deliver to you so that you'll be happy and continue to renew your membership. So, the construction of the business model is also something that sits in contrast to most communities because most communities have a there's a playbook on how to monetize communities, but inevitably inevitably they all turn into you becoming the product in one way or the other. And so, I think that that's we we took a stance at the very beginning, we weren't going to allow certain people to join and we were going to charge money so that we could maintain some degree of independence. Even though we do have sponsor partners, their relationship with the community is very, very different than what I've seen from other places. And I think that that decision at the outset of just building the last point that I'll make is that again, because I just think business model and incentives drive so much behavior as, you know, Warren Buffett and Charlie Munger will tell us, our our decision to not try and monetize every every nook and cranny, you know, of the of the of the platform of the community. It's just you pay a fat fee. We do as many things as we can. We raise that fee over time so that new people pay more, but we pour as much value into that bucket as we possibly can. And that is our only incentive. As opposed to, we sent you a job listing and we're going to have a 10%, you know, fee on the back end with the recruiter or we're going to let you know that Salesforce is a sponsor and every time somebody sells signs up for Salesforce, we're going to take 10%. There's no ulterior motive. There are no hidden incentives when you're a member of revenue collective. And again, I think that that helps over time separate us in addition to the values and vision that we have about your career. I like that model a lot. And I actually wanted to point out one other thing that even though you you did say that you mentioned or you mentioned rather that you have some sponsorship, the sale to the sponsor is is premised on the existing business model that you have a targeted group that doesn't let everybody in that has a that has a hyper specific community and they know what they're getting into. And there's no illusion that will ever change. That's that's the core business principle, right? So even a sponsor going in knows that their audience is targeted and limited. And yeah, and that's important because they're never going to expect more from you in terms of widening your base to every investor's founders, whatever it may be that wasn't part of your core offering. Yeah, that's exactly that's that's that's right. And also because sponsors are 10% of our revenue, not 100%. We can turn people away. Yeah. And we can also say, yeah, you know, we're not going to give you their email addresses and we're particularly not going to give you their email addresses. If you're going to give those emails to an SDR to pound their inbox, you know, for they find out for one webinar and they get 22 emails every day from different people at the company. That's not we work hard to try and make that not the case. So the the the community makes sense the way it's set up makes a lot of sense. Now let's speak about the people that are in it. So the commercial operators, CROs, VP sales, let's first define what it is to be that individual in a company today outside of the limited tenure. What is a job description look like? Well, again, and we called it revenue for intentionally not sales collector or market and collective because we include marketers, salespeople and customer success people and even operations people that support those and that's the point is also speaks to my perspective on how how is revenue generated. It's not just the sales team, right? It's the collective effort. It's really the collective effort of the whole company, but at least if we're going to be more specific, it includes the alignment and the interaction of the sales marketing customer success professionals that are working to generate revenue. So within that world, if you're in charge of sales, you know, you are a person responsible for closing the deals, you're responsible for building the team, managing the sales team, managing different revenue channels potentially, including channel partnerships in addition to, you know, inside sales and outside sales and field sales. If you're the CML or the chief marketing officer, you're the VP of marketing primarily in the modern world, you know, and I think in many ways marketing is more interested, more complicated and more difficult than sales because it covers so many different things. But if you're the CML, your job is every day. Again, the most recent modern parlance would be to your job is to generate pipeline. I think that the actual job of chief marketers is beyond that and is more nuanced because your job is also to elevate and support the brand. Now the other people that have a big role on the brand is, you know, everybody else, including the sales team, the product team and the customer success team because the best way to build a great brand is to build something that people truly love and then they will tell their friends. But it's not just the marketers responsibility, but it is the marketers responsibility to take the feelings that people have about a brand and turn that into direct actionable language. And then the customer success people, you know, ultimately their job is to make sure that once you sign up a customer, they don't leave. And so, you know, across that journey of creating awareness, attention and interest, you know, using the AIDA framework, that's the marketers job and then decision in action. That is the salesperson job and then long-term longevity and, you know, and renewals. That's the customer success job. And those are all hard jobs anyway. But in today's world, so what is it about today's world? Well, there are money is free in today's world. So what does that mean? That means that the venture capital asset class has never had more money and has never had more funds. And I think I saw a chart over the weekend. So there are more investors because money is free, right? And if you are looking for returns, you have lots of equity capital to invest. And that means that you're going to invest it. And that means that there are going to be more companies that are seeking that capital. And that means that it's going to be more competitive. And that means that many, many, many more companies are going to be pursuing similar personas, similar business problems, similar solutions. And that means that your job is harder, while all of the venture capital has gone into these companies and venture capital, the definition of it is it seeks, you know, an extraordinary growth rate. It seeks extraordinary turns. Now, you know, one of the issues in my experience is that the returns are not venture capital, doesn't describe an outcome. Really, it's just capital. But they all seek the same outcome. And they, because, you know, to a hammer, everything looks like an ill, they have money. They assume that the thing that creates great outcomes is money. And when they pay the money, they expect the great outcome. And what that means is that thousands and thousands and thousands of companies have growth targets that are probably elevated and artificial relative to their actual potential. And they feel tremendous pressure to pursue those growth targets. And finally, the end of our story, that puts pressure on the sales and marketing talent. And of course, because there are so many more companies, but the quality of the talent and the relative training of that talent is probably much more diffuse. Many more people inexperienced in these jobs and they need support and they need help to be effective at those jobs. And that's again, where revenue collective comes into play. And I guess the point I was making with the commercial operator or the revenue operator, and you widened it out to sort of help me understand the scope of who's in the actual collective. But I was curious about the point that you made earlier about the CRO VP sales, that tenure keeps decreasing. Explain why that tenure keeps decreasing and how revenue collective seeks to mitigate that. Because you didn't mention customers' success. You didn't mention those leaders are, they're only sitting in a company for what was the 17 months. You didn't mention marketing leaders or perhaps that says, okay, I don't know, I want to put words in your mouth. But I'm curious as to, I guess, sales holds the bag. They're the ones that are getting hit the hardest with not hitting these accelerated revenue targets or whatnot. So how does revenue collective help them? Well, in your point, customer success is slightly longer, but marketers are very much in the bucket of the salespeople with declining average tenure. And I think that you mentioned like what are the reasons for that? So one of the reasons is the proliferation of capital and the number of companies and the quality of talent being spread across a much greater number of companies. That's probably one reason. The other reason is that there is a point of view that people are stage specific, right? And that you are the leader for the zero to 10 million range of the company, but we're going to need somebody different for 10 to 30 million. And we're going to need somebody other than that for 30 to 100. And I think that there's a lot of, there's a negative feedback loop that's in play where sales and marketing people are viewed as interchangeable. We are treated interchangeably, that's we act interchangeably. And I think all of this is perpetuating itself. So revenue collective seeks to address that in in three primary ways. The first is we want to help people get better at their job so that they can stay longer. And I think one of the things we want to do is market that we make better people better at their job so that the companies have more confidence that any given leader, whoever she or he may be, can scale to a specific revenue range. And we do that by providing access to the community itself, which provides real time insights. You know, you can go ask a question and get 15 people that have been there done that to answer it quickly. So we want to help you get better at your job. And we take all of these interactions that people have and we create content from it. So we create workbooks and playbooks and we make them instantly accessible. We create webinars and over time, we really want to create, I don't know if we'll call it this because there's so many people calling things that, but something like a revenue collective university. But basically when you become a revenue collective member, you have the chaos of just meeting all the people and getting to know people and building those intimacy and those relationships. But also that from all of those people in their insights, we've built structured programs so that you can find up for the CRO program or for the VP sales program. So you know, that's part of what we want to do. Now the second thing we want to do is we want to help you find a job. Hey, it's Scott here. I just want to take a second to thank the sponsor of our show Teachable. What is Teachable? Well, let me start with this. If 2020 has taught us anything, it's that nothing is for sure. Nothing is a guarantee. Everything was flipped on its head, including our job security. A lot of people realized that brick and mortar had to move online, had to move digital and those jobs that we've had for 20 plus years weren't so secure. So what do we do? How do you future proof? Well, you start your own thing. You build your own business. It doesn't have to be completely replacing your nine to five. It could just be a side hustle. But you are finding ways to productize yourself, your knowledge, and things that you can sell to people that can benefit them that will allow you to bring in multiple streams of revenue and income. So how do we do that? Well, Teachable is the platform that allows you to productize and monetize your knowledge. It allows independent entrepreneurs and creators to build and sell fully customizable online courses and services. You are taking what you know who are building courses. You're using Teachable and you are monetizing your years of experience. There are over 100,000 instructors and creators who have transformed their knowledge into world class courses and Teachable has paid out over 500 million dollars to help get you started as a special offer for everybody who's listening to the podcast today. 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I have absolutely no interest in starting a recruiting firm. I don't like transactional revenue. I like recurring revenue. And so there's a huge benefit to that. What is the benefit? We can work with every recruiting firm because we have no interest in their economics. We actually want to help them. We think that if we help people connect to great recruiters and great hiring managers and they find jobs, they're just more likely to renew their membership. And if we're leaving a little bit of money on the table, that's great. We're happy to do that because we want to play for a much longer term. So we want to help you get better at your job. We want to help you find a new job if you need to. And the final piece of it is we want to arm you with the right information and insights so that you can negotiate more effectively for that job. Because I personally, you know, I'm impatient and I get bored easily. And maybe the right tenure for me is nine months. Maybe the news had it right. I don't have a point of it. This isn't a bad guy good guy. This isn't a moral argument. This isn't an argument that if we're all going to workplaces a year and a half, then the deal that is presented to us needs to change. Because it has become unfairly skewed to the company. Or again, use the word fair as a little tenuous. But you know, I want to renegotiate. I want to renegotiate. If I'm going to work somewhere a year and a half and I'm going to help them get from point A to point B, which is incredibly valuable, then you're going to have to pay me differently. And that's okay. So let's figure that out. And so there's a number of ways that we coach people so that they can have more information and more confidence going into negotiations to anticipate some of these challenges. That was going to be, I guess, my next question. Because you have, you know, coming from, coming from a sales and marketing background in my career, I align with a lot of the things that you're saying. But when you look at the reality, you see these interchangeable roles where you see these VP sales getting the marketing department added on to their, you know, their list of things and roles and responsibilities. And the commercial environment is not synced up with, I would say, the commercial environment at large, I don't think is synced up with what you're preaching within revenue collective. So when you have these two conflicting forces where you have perhaps founders that are a little bit outdated and they, and they aren't working with perhaps the best venture capital firm is giving them the right advice on who to hire, who to look for. How do, how do you navigate that workforce? How do you navigate which companies to work for? What are the red flags that you should look for when you go take on your next role or your next job to make sure that it aligns with the way that a company should be hiring and managing and onboarding and setting their, their executive is up for success. Well, there's, there's a lot of questions in that in that. I know there's a ton. I was just thinking through, I'm sorry. That's what I do. I think, so there's a couple pieces. The first thing is, you know, and I do part of what we offer our members is coaching calls. You know, so I was on one yesterday, which was a Sunday talking to a member and she was a consultant that was interviewing. She'd been a consultant for a really long time and hadn't taken on a full-time role. So we're kind of going through things. And the first thing is, you know, before we talk about negotiation or red flags, we have to understand the labor market because if there's no jobs and you need to pay your mortgage or pay your rent or put your kids through private school, then some of what I'm about to say is less rough. And because the first things first, you got to take care of yourself. And leverage changes, if it was the employment market nine months ago, we would have probably more leverage. Now, the VC funding environment right now is actually quite hot. But the point is, I can't speak to your personal circumstance. And depending on how many choices you have and how much leverage you have, that'll determine the extent to which you use my advice. Now, the second part of it is that, again, there's, there are, you know, it's less about kind of red flags, although I can give you a couple red flags. I mean, if they won't share information with you and you're an executive, really, if you're an employee, and the company won't share information with you, what kind of information? What was the most recent funding round? What did it value with the company? How many shares are outstanding? What's the price per share? You know, has anybody sold secondary, meaning has anybody taken money off the table in the moment's mean leading up to joining the company? What, let me see your previous board decks. Have you hit the number? What was the number? Are you giving me the plan? Or do I have to, you know, I mean, again, red flag is, we've set a growth target of X. Scott, you're obligated to hit X when you join, and if you don't hit X by nine months from now, you're fired, is obviously red flags since you didn't have any opportunity to weigh in and to build that plan yourself. So there's a number of ways that people might run an interview process. I would also say that frankly, anybody that's pushing speed, you know, speed in an, in an executive interview process, I think is a red flag, right? These, these are supposed to be, you're trying to work there for longer than 18 months, right? This is supposed to be some, if it's not a, it's not a great marriage. It's not going to last 20 years, but you know, we don't want it to be a two-year marriage. We want it to last a while, at least advocate or two. So, and so, so I think if people are rushing the interview process, that's a big problem, and of course, people are obligated to do their own due diligence. But the, the main things that I would say are in terms of like, how are we trying to change this? How are we trying to change the structure? He is really around, the idea is you go to work for a startup and you get paid probably below market relative to a big enterprise company in cash. But that's because you get above market in terms of the equity opportunity. And you know, the reason that many of us work at startups is is because we've all read about the person that worked at Slack or Facebook or Google and even like some of the most famous investors are just, they were just early employees at Facebook and Google. So, we all, that's why we join startups. That's why we joined these early stage companies for the equity opportunity. Okay. Well, the equity framework doesn't make a lot of sense, given a couple of things. How long it takes the company to go public? How long you were expected to work there? All related to the structure of the equity that they issue you, which is a long way of saying that most people get equity, which vests over a four year, these are options. They're granted options over a four year period, let alone the one year cliff, which we can talk about. But so if you're only working somewhere a year and a half and a meaningful part of your compensation is intended to become real over four years, there's an obvious disconnect there. It's just very clear. You're in a half to four years. The other part of it is the reason that options are on a four year vest is because companies typically and, you know, the olden days took four years to go public because they could go public at much smaller sizes because of the regulatory requirements around filing and becoming a public company. We're less. So now they take much longer. So what happens is they take longer for more investors come in, they raise more money, you get diluted more. If you're only going to work there a year and a half, it means that the event, the place where you can turn this equity, which is a meaningful part of why you're working at a startup in the first place, the place where you can turn that equity into cash, which is the point of all finance, turn it into cash, is way down the road when probably you won't be there and you will have much less influence in terms of who gets it, how it gets it, and et cetera, et cetera. So all of this is a long-winded way of saying that let's rethink this. Let's rethink it. Let's say maybe you keep the equity, maybe you don't work for equity, but maybe you work for milestone-based cash bonuses that function very similarly to equity. If I'm going to take a company, this is my favorite, you know, one of my favorite comparisons, and sorry for being long-winded, but if I'm going to take a company from $2 million in annual or current revenue, $2 million in revenue to $10 million in revenue, which could take about a year and a half, right? That's a common journey for an early stage, the VPCL's VP marketing. What are you doing between two and 10? $2 million is not, yes, it's a company, I get it, but it's not really a company, and what do I mean by that? The investors are the reason that you pay more money at later stages is because you've removed risk from the business model. At $2 million, there's still a tremendous amount of risk. A tremendous amount of risk, not just about whether the market is truly there, but about whether the way you've designed your company is the right way to do it to attach that market. So you come in at $2 million, now what is $10 million? $10 million, you have removed a tremendous amount of risk. A tremendous company that have $10 million in revenue can typically, unless they're completely mismanaged, find some path to profitability, especially if they're software companies, right? $10 million, that's a hard company to kill. That's pretty hard, you know, $10 million is a lot of money. Now it may not seem like that if we're all working at, you know, Salesforce and they're doing billions in revenue, but that's the truth of the matter. So you've taken something, you've been part of the team that's taken something from high risk, really uncertain, and two, we've removed, now we're just trying to figure out how much is it going to be worth, but we know it's going to be a company, that two to ten journey. Well, if you were there a year and a half, you know, again, a small portion of your options have vested, you might have raised money at a massive financing round that didn't give you the opportunity to sell anything and put the company so far over its keys in terms of valuation. So instead of, and you might just get fired, by the way, because the two to ten person is likely going to be different than the ten to thirty person. So instead of this structure where you've contributed a massive amount of value and have not really received anything commensurate in return, what if at the moment that you hit $10 million in revenue or $8 million in revenue, you get a $250,000 cash bonus. Instead of the point of equity, which are probably not going to be as meaningful anywhere, maybe you get half the equity, what if you have an opportunity to sell your equity earlier and take money off the table so that at least you can realize some of the gains or what if you have the opportunity to not have to exercise your equity 90 days after leaving the company. All of these are very specific start-up, you know, practices, but again, I just think that they're outdated, and so I think that, you know, what people need to do is arm themselves with information and then confidence, because that's the other part of it. I think a lot of sales and marketing people, you know, we don't deal with investors all the time, and we're not founders, and so we haven't had to set up a cap table and duo of the things, and we're just much more comfortable arguing or negotiating about cash. But I do think that the other part of it is if we can give people the right information and the right confidence to more confidently discuss equity, they can have a confidence to realize that all of this is negotiable, there's nothing that's not negotiable, and that they can change it if they have the confidence to change it, and we're seeing that with revenue collective. The final piece, I would say, is severance. Again, like the last part of compensation and the thing that I just really strongly feel like every executive should be arguing and negotiating very forcefully for severance, pre-negotiated severance, so that, again, I don't, what I want is, I don't mind working somewhere a year and a half, you know, it's okay if you fire me after 10 months, but it's much better if I pre-negotiated 12 months of severance. That makes that decision much more expensive for you, and that makes it, that means that you can't, you've got to be, it's got to be meaningful, you've got to think about it, and that's okay, you should think about it, you should think about it before you hire me. We are not interchangeable, and I'm not coin operated, and if you want to treat me like that, I'm going to make it much more expensive for you to treat me like that, so that maybe you can think about it a little bit, so. I like it a lot, and I think that, you know, I was actually going to bring up a point that you just ended up going and touching on anyways, but a lot of sale, or I keep saying sales, because it's my back. A lot of individuals, executives who perhaps haven't been as tenured, you know, like I don't know, not, not put an age on it, but younger, they wouldn't have had this experience before, they don't know what they can and cannot negotiate, they don't understand all the nuances of all these different arrangements, even negotiating severance is something that they may not feel comfortable doing, let's have been presented in roles before, and if you think if they're coming from working in a company for 10 years, and they moved up, and now they want to pivot into startup land, this will be their first foray into having the ability to negotiate with literally, quite literally the founder at that stage, so I'm assuming now that you're speaking through it, these are all things that they can learn from revenue collected from the community, these are all people that can support them, I don't know if there's like legal or whatnot in the community, but I'm sure there's some people that have tons of experience with this that on your own, this is scary as hell to go in and negotiate. Exactly right, and again, it speaks to the business model again because we don't sell, now people do get their dues expense, but we don't sell to the company, we sell to the individual, the individual goes back to their hiring manager, their CEO, but that's all intentional because we want to be, there is no other place in my experience where you can get these questions answered, there's many, many places to figure out who should SDR report to, or how should we set up the complaint, should it be meeting SDR meetings held, but where do you go to figure out, is this the right amount of money? I'm actually pretty scared, they've offered this to me, does this sound fair to you? And again, my call yesterday, because I do these calls every day with members, the women, does this sound fair? I said, no, it doesn't, it's not fair, it's not right, and that's what you want, that's the thing that's helped, that's the thing that I'll help you sleep at night is knowing that there's a group of people that are not subservient to investors, I'm not trying to please first ground capital, or VISTA equity partners, I don't have anything against them, but I don't exist to please them, I exist to please the people that work for them, they're my members, so yes, those are questions that can be answered, and again, I think that the biggest thing that surprises people is, is how, no matter what they say, I don't care what they say, I don't care what the general council says, or what the founder says, well, this is the equity package that we issue all of our employees, and we would never change it for just one person, okay, well maybe you should change it for all of the employees then, or at least you should have classes and you should have an executive class equity package and a non-executive class equity package, but these things are changeable, and you can change them, you know, I'll give you a specific example, I was working at Axial, and I didn't know, I was in that position that you're talking about, I was an early BP, I didn't know what to ask for, and all of a sudden, the CFO one day comes and he puts together, he puts a piece of paper in front of me, that is a paperwork to sign that as an amendment to the equity stock option plan that gives me as the option holder, a double trigger full acceleration, so double trigger full acceleration is you have options that are unvested, the company is sold, that's the first trigger, and then something happens to you like you're fired, that's the second trigger, so let's say a big company like Salesforce buys your sales engagement company, that happens, and then they say you know we don't need a VP of sales, but you can be senior director of field for the Toronto region, and you say well that's not really the job I had, I used to be SVP of global sales, they say sorry if you don't want that job then you don't work anymore, those would be the two triggers, upon that your unvested equity accelerates, so that you can get the full benefit, the full realization of the value of that acquisition, all right, so that's a term that's fairly common, I hadn't heard of it, somebody put a piece of paper in front of me to sign to give me that risk, how did that happen, that's because we were interviewing a VP of marketing, and she said I'm not going to join the company unless there's double trigger full acceleration, and they said well then we would have to do that for all the executives, and she said then do it for all the executives, and guess what, let's be executives, got the term, so you know I just, I said anybody's out there listening, or I know that it feels scary, and it should, and again remember all of this against my first caveat, which is if you don't have leverage, then you don't have leverage, but if you do have leverage, you should at least know what's possible, and you should know that things can be changed, if they want you bad enough, things can be changed. I like that a lot, it's refreshing because there's a lot of people that come on the show that speak about, like you mentioned, like strategy on how to do this better, how to do that better, but I don't think I've ever spoken to somebody on how to negotiate your professional, it's something that you're right, I've never heard of it before, I've never heard of a group that does it at all, so it's, you know, hats off to you for doing this, and hopefully it continues to grow, I think that you see some, like you see revenue collective all over LinkedIn, so it's obviously, you have 3000 members, obviously doing something, so hopefully, you know, when COVID is maybe a little bit decided, and people do have a little bit more leverage, that's when they can start taking advantage of some of these things, if not just keeping a top of mind right now, right, as they go into potentially new work environments, like hopefully the economy's turning around a bit, a lot of people were laid off, so this is when they have to exercise that, right, if they want to go in and negotiate all these, all these different options you mentioned, now that being said, I want to, I wanted to ask you some questions based on your career, your experience, just like personal insight that I like to dry out from somebody who's done so much over their career, before I pivot, is there anything that I didn't ask about revenue collective that I should have asked? No, no, you know, I think if folks are intrigued or interested, or you want to learn more, you can go to revenue collective.com, there's an application process, you click on a apply now, we've got communities and chapters, it is COVID, so you know, it's a digital first community, but we've got people everywhere, everywhere in the world, we've got, you know, we just signed our chapter heads for Sydney, Australia, and they're going to cover Melbourne and Perth for now in Brisbane, Charlotte, North Carolina, Dallas Fort Worth, and Birmingham, Alabama, and you know, with Manchester, UK, Stockholm, Sweden, so you know, anywhere you are in the world, if you want to become a member, we'd love to talk to you. Very good. Now, in terms of the evolution of these executive roles within organizations, it's something that you're understanding all the time, you're looking for new ways to improve how an executive can transition and negotiate into a new role, as well as just other instillery topics that will help them be successful in the role. What are you curious about, or what are you investigating in the world of leadership, what are people looking to incorporate, or what should they, what should people focus on bringing into their own persona as a leader that can help them accelerate in their role right now? Something that isn't as common. Well, I don't, here's one thought. There's something that I've just been thinking about a lot. I think that people need to be as invested in their career as a professional athlete, would be invested in their career. That is something I would share with people. Professional athlete, reviews, game film, professional athlete, has a nutritionist, they have a weight trainer, they have people that help them get better at each facet. I don't see enough people, and this is speaking my book, so there's an obvious conflict here, but I don't see enough people making investments in their career, besides a community like revenue collective, because I honestly don't, you need to be part of something. You need to have some kind of mentorship or some kind of group where you can go, and it doesn't have to be my group, but you need some group where you can go and ask people that you trust and respect how to do something, what to do, what they think about something that you haven't experienced before. But the other part of it is that I think more people should investigate coaching, hiring coaches. It's just internalizing the concept that there is an advocate that only speaks for you, that doesn't come from your company, that you pay for out of pocket, that helps you get better as an individual, and that helps you address perhaps things that are long-standing challenges or impediments to your personal growth and development. And I specifically would contrast that with a therapist. I don't think that, I don't think, mental health is incredibly important, and so it's not about, this is just for me personally, but for me personally, I've tried both therapy and working with a coach, and I've gotten practical, actionable, like my life has changed, the more I've worked with a really good coach, and I didn't get a lot of benefit from traditional talk therapy. So I think as people are, we're in a volatile world, and we know that, and you need to arm yourself with personal resources. This is like a very, very rare anecdote, but I don't believe that I don't want the company to buy my computer. If I were to ever work for somebody again, which I, you know, I hope not to, but if I ever work for somebody again, they're not buying my computer, and I'm not asking them to, I don't, I don't want you to own my computer. You don't get to, I bring, I'm like a free agent athlete, I bring a coach, I bring a graphic designer, by the way, if you're a leader out there, and you don't have access to your own personal contract freelance graphic designer, so that you can put together your own presentations, and they look good, it's enough with like the, the terrible like your advertising, particularly more experienced people, sometimes you're advertising your age, when you put together decks that just look like absolute dog shit, and you're like going into a final round interview, just look like grandpa or grandma, I don't want to do that. So you need to surround yourself with an arsenal of resources that are dedicated to you evolving as a human being, not about the companies subsidizing all of this for you, because again, if we're all going to workplaces a year and a half, it's just like a hockey player or football player or baseball player. So they all have their own weight trainer, they all have their own coach, they all have their own hitting instructor. We all, as leaders, we need to do that. We need to arm ourselves, and we are, we are fully formed autonomous executives that can parachute into a company if they want to treat us transactually, that's fine. And we will have the ongoing resources necessary to help us navigate this difficult environment. And again, that's sort of the point of revenue clip there. Do you find that, do you find that executives are doing that more often creating this, this almost this machine that supports them when they go into different, because that's outside of what I think most people think of when they apply for a job, they think I don't want to spend my money on this. I don't want to spend them. This is, you know, I'll just expense it. This is part of the company. They should be paying for this. They should be paying for my coaching, my executive training. Do you find that more executives are just taking revenue initiative on their own to take control of their own career? I hope so. I hope so. They, I, I just, you got to understand, I don't care what the person says about confidentiality. The person that's paying the bills is the boss. And you, I do think that executives need to be a little bit more long. You need to invest in yourself. It needs to be an investment. You need to be prepared to spend your own money on getting better. And if, and if you're just like, well, I won't do that unless I can expense it, you're just short-changing yourself. You know, you just have to have a bigger picture view of the world. This is not about every single time you do something sending in the receipt to get an expense. This is about you building a career in a world that is not going to help you unless you help yourself. That's very powerful. That's a, it's a, it's a very different view of career than what I think a lot of people expect. But I think it's, I think it's um, I think it's an effective view of career. I think it's, you know, I see a lot of people that try and build, you know, when you talk about building a brand, I think that building a brand is a lot more than just a couple posts on, on social media. I think that what you're speaking about is your brand extends far deeper. And now you have your own little teamwork working for you. Basically, essentially. We're all gonna, I just, you know, again, some of the 18-month thing isn't, you know, nobody's at fault. There's no enemy. This is the way the world is now. You know, we're all impatient. We all want instant results. And if that's going to be the way the world is, then we need to prepare ourselves for it. Yeah. And to be quite honest, if you are transitioning from jobs every 18 months or even if you are and you're better protecting yourself, the expenses will pay for themselves. Exactly. It's, it's, it's, it's, it's in the gates, the cost. Okay. One, just two more, two more quick questions. This one's a little simple, but I still like to understand your point of view. What would be one lesson across your entire career that you would tell your younger self? All right. The biggest one is, you know, I always say the person that takes their life seriously the soonest is the person that will win. I have, I can probably think of a more pitty way of saying that or articulating it, but like, I, the problem with me as a human being and, you know, to the point of like the vision of revenue collective unlock your potential because for most of my life, I felt like I had potential that was not being exercised. And that is because I had a lot of early success as a very young person in school. And I got used to this idea that success came easily. And I could do with a moderate amount of effort I could achieve exceptional results. And the real world has a way of slapping you in the face when you think about that. And I just think I wish I'd started running sooner. I'd wish that I'd worked harder. I wish that I had spent less than I made sooner. And that I'd learned, but, you know, that's just, there's, I could tell that to my younger self. I don't know if my younger self would have believed it, you know, because the way that you learn things is the hard way, which is through experience. But I fundamentally believe that, I fundamentally believe that if I just worked, if I'd been more diligent, taken things more seriously focused more on hard work as early as possible, you know, I would have achieved great things. But the only way I know that is through what I've experienced. So I don't even know if it makes sense sometimes to say those things. No, but, but it may not make sense to, to your younger self, you know, when you, when you were younger, but if somebody's listening, hopefully, hopefully they take that to heart. That's all you can, that's all you can hope. And then they don't have to experience, experience is the, the ultimate teacher, but if they can shortcut some of that experience with a little bit of self-awareness and aligning with people that have done it before, that's absolutely right. Yeah, that helps too. And then last question before I get some websites and socials from you, what does success mean to you? I wish, you know, the thing about cliches is that they're true. That's why they're cliches. For me, I am, I mean, success is realizing the potential of this opportunity. And it is also correspondingly because I, you know, they talk about like being rich versus being wealthy or, you know, I want to be as free and as independent from the constraints of, of, you know, traditional society as possible. And that would be success. Success is controlling your own time and controlling your own day. And that's why, and having fun doing it. And that's what I'm doing right now, you know, running your own company, especially when there's not investors. Now, there's probably a downside to that, but, but there's a lot of upside. And the upside is, I control my day. I decide what happens. And it is, you know, the, it is besides, you know, the people I love in my life, the most important thing to me. And it's because I have the independence and autonomy to make my own decisions. And so that, for me, is what success truly is. Very well said. And most importantly, where do people connect with you? Where do people go find out more about the revenue collective? Give me some links so we can go check out. Sure. As I mentioned, so first, if you want to email me, you can Sam at revenue collective.com. Maybe mention that you heard me on the podcast that would help. If you want to check out revenue collective, revenue collective.com. If you want to apply, click apply now. We have a program for executives, and we have a program for associates, so people that are on their way up that are not yet at the executive level. You can find us on LinkedIn as well. LinkedIn.com forward slash the word in forward slash at Sam F. Jacobs. Those are the, those are the big ones.



























