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

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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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Scott, Scott D Clary, Sam Jacobs


Scott D Clary  00:05

Thanks again for joining me today I am sitting down with Sam Jacobs, who is the founder of revenue collective. Now, Sam first, you know, 1516 plus years, he’s worked with a variety of companies as senior sales, executive leadership. He’s up companies 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 SAS and recurring revenue businesses, including being a commercial operator at GLG live stream, slash Vimeo, the Muse and behave Hawks. Now, what he’s working on is revenue is the revenue collective, which was started as 100 member group, January 2019. Fast forward to 2020, there’s over 1400 and growing, invite only, 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 2500 downloads. So you know, he’s gonna put me on the spot now makes 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, and all of that. So I appreciate you sitting down.


Sam Jacobs  01:38

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 indicator which is totally, which is, which is great to revenue Collective is actually just around 3000 global members at this point. We’re, Oh, it’s okay. We’re in probably over 100 cities all over the world. We we got started in New York in 2016. And I can talk all about that. And, and then the sales hacker podcast actually gets its gets about 40,000 downloads a month. So, you know, been doing that for a couple years. But my background is I’ve been, you know, 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 boom. And I moved up to New York to do investment banking, I wasn’t really into that very much fell into 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, and 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 Lehrman group, and that company has 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 is 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, you know, a rocket ship, the company was incredibly profitable, paid out. It was very shareholder friendly. And all 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 return, which is incredible. And I came out of Georgia in 2010. And for the last 10 years, you know, prior to revenue collective, was leading and kind of Chief Revenue Officer type person for early stage companies, primarily series A and Series B companies, although, you know, sort of it varies based on the company, but a couple things are happening, particularly the last 10 years. So the first thing was that, you know, as I mentioned, I worked at Gog 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 live stream for two years, I then worked at the Muse as Chief Revenue Officer for nine months. And I worked at behavior X 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 you know, five jobs. And so that was that was an issue for me. And that was, you know, 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 lead position at a high growth company is just 17 months at this point. So on average, and you know, I talked to a lot of people that have worked places for 1015 20 years, but on average, people are leaving jobs, you know, under a year and a half. While they everything that’s happened over the last 10 years, it’s just that the way that people go to market, the way that companies need to generate revenue obviously changes all the time. And you know, new technology, new tech stacks, new functions, the str function was actually a rather new function 10 years ago, and the sales development rep function. And now you know, 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, you know, I was trained that every every piece of content that a company created needs to live behind a landing page, where you captured an email address now and 2020. The idea is that landing pages and email capture is over, or at least in decline, and much more fashionable is 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, Latin Aiko, and the Chief Marketing Officers, 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 15 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 a 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, and 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 collective. 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, and so, 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 with 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 collective 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’s a member of revenue collective, and we want to help them achieve their potential. And however they define their potential, whatever 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 that 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.


Scott D Clary  09:08

I appreciate it. And it makes a lot of sense. And when you speak through why revenue collective has taken taken hold it, it’s like common sense isn’t common. So you have a role that’s ever changing, you have a commercial landscape is ever changing. 10 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 today? What are the what is out there? That revenue Collective is in contrast to?


Sam Jacobs  09:42

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 celeb birdies in the startup ecosystem are not you and me, Scott. They’re not they, they’re not the operators. There’s two celebrities to 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 fealty to those, to those stewards to those personas, right. So Vista Equity Partners, very famous private equity firm, one of the best SAS 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 that 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 just as limited partners to be to be direct. Yeah, I remember when I was at axial, and I left axial and axial as 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, you know, that first round review, they put a lot of money into their platform, that 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 hasn’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, you’re the product. Yeah, yeah. And so all of these other communities, yes, they’re free, but the way that they all aspire to generate revenue, you know, 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, right? The people that pay the bills are ultimately your master. And so you have to promise to them that you’re going to build as big an 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 occurred 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 a problem with it. And I do learn things from LinkedIn. But I’m the product, I know that I’m the product. And I think that that’s, 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 at some consultants joined. But most large scale consulting firms, we do not let giant. And that means that when you join, and when you pay your monthly dues, or your annual dues, you know that it’s a curated community. And you know that you’re not the product, because you’re paying 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 in 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, we took a stance at the very beginning, we weren’t gonna 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 drives so much of behavior as you know, Warren Buffett and Charlie Munger will tell us 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 flat 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, oh, 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 feels signed up for Salesforce, we’re gonna take 10% There’s no ulterior motive, there are no hidden incentives, when you’re a member 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.


Scott D Clary  15:33

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 meant or you mentioned, rather that you have some sponsorship, the say the sell 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 that has a hyper a 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, then that’s important, because they’re never going to expect more from you in terms of widening your base to every investors, founders, whatever it may be, that wasn’t part of your core offering.


Sam Jacobs  16:17

Yeah. 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 signed up for one webinar, and they get 22 emails every day from different people at the company. That’s not, we work hard to try to make that not the case.


Scott D Clary  16:50

So 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 the commercial operators, CROs VP sales, let’s first define what it is to be that individual in a company today, outside of the the limited tenure, what does the job description look like?


Sam Jacobs  17:10

Well, again, and we call that revenue for intentionally not sales collector or marketing 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 is 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 inside sales, and outside sales and field sales. If you’re the CMO or the chief marketing officer, you’re the VP of Marketing, primarily in the modern world, you know, and I think, I think in many ways, marketing is more interesting, more complicated and more difficult than sales, because it covers so many different things. But if you’re the CMO, your job is every day. Again, the most recent modern parlance would be do your job is to generate pipeline, I think that the actual job of Chief marketers is beyond that. And as 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 so that 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. But 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 the journey of creating awareness, attention and interest, you know, using the AI da framework, that’s the marketers job, and then decision and 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 those are all hard jobs anyway. But 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 if I think I saw a chart over the weekend, so there are there are more investors because money is free, right and a few if you’re looking for returns, you will 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 as it seeks, you know, an extraordinary growth rate, it seeks extraordinary returns. 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, it’s just capital, so, but they all seek the same outcome. And they, and they, because, you know, to hammer, everything looks like a nail, they have money, they assume that the thing that creates great outcomes is money. And when they pay the money, they expect a great outcome. And what that means is that 1000s and 1000s, and 1000s of companies have 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’s so many more companies, 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.


Scott D Clary  21:18

And, and I guess I, the point I was I was making with the the commercial operator or the revenue operator, and you widened it out to sort of help me understand like 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 10 year keeps decreasing. Explain why that 10 year keeps decreasing and how revenue collective seeks to mitigate that don’t say, because you didn’t mention, like customer success. You didn’t mention those leaders or, you know, they’re only sitting in a company for what was it 17 months, you didn’t mention marketing leaders, or perhaps that’s is the case, I don’t want to put words in your mouth. But I’m curious as to, you know, 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?


Sam Jacobs  22:07

Well, into your point, you know, customer success is slightly longer, but marketers are very much in the bucket of the salespeople with 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 gonna meet somebody other than that for 30 to 100. And I think that there’s a lot of, there’s a this negative feedback loop that’s in play where sales and marketing people are viewed as interchangeable. We are treated interchangeably, thus, we act interchangeably. And I think all of this is perpetuating itself. So revenue corrective 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 jobs 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 a 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 we have 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 in those relationships. But also that from all of those people in their insights, we’ve built structured programs, so that you can sign up for those 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.


Scott  24:19

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Sam Jacobs  26:15

If we can’t help you get better, or if we’ve gotten as far as we can go, then the other thing we need is we need to be the Nexus we need to be the central clearinghouse for every executive go to market position, or at least we need to aspire to be that. So that you always feel like you can find a job. And that’s where our business models very, very important, as I mentioned, why? Because we don’t need seek want to take referral fees from recruiters, we don’t want to be a recruiter, the number one thing someone will tell you, if you start a community is you should start a recruiting firm, I’m never going to start a recruiting firm, I’ve 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, 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 and I get bored easily. And maybe maybe the right tenure for me is nine months. Maybe the Muse had it right? That’s I don’t have a point of view. This isn’t, you know, there’s no, there’s no like bad guy, good guy. This isn’t this isn’t a moral argument. This is 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. And because because because it has become unfairly skewed to the company. Or you can use the word FERS a little, little 10 tenuous, but you know, I want to renegotiate, right, 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 gonna have to pay me differently. And 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, these challenges.


Scott D Clary  28:31

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 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 in onboarding and setting their their executives up for success?


Sam Jacobs  29:38

Well, there’s there’s a lot of questions in that in that I know there’s a


Scott D Clary  29:41

ton I was just thinking through I’m sorry.


Sam Jacobs  29:47

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 remember and she was actually 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 circumstances. 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, and really, if you’re an employee, and the company won’t share information with you, what kind of information what was the most? What was the most recent funding around? What is the value of the company? And 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 moments 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, 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 a red flag, 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 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, it’s not a, it’s not a great marriage, it’s not gonna last 20 years, but you know, we don’t want it to be a two year marriage, we want to want to last a while at least have a kid 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 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 the 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 joined 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’re expected to work, they’re all related to the structure of the equity that they issue, which is a long way of saying that, most people get equity, which invests 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 year and 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, that means that the 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 etc, etc. 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 and this is my favorite, you know, one of my favorite comparisons and sorry for being long winded. But if I’m going to take your company from $2 million in annual recurring revenue to 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 VP sales you key 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 attack that market. So you come in at $2 million. Now what is $10 million $10 million dollars, you have removed a tremendous amount of risk. A tremendous companies 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 Salesforce, and they’re doing billions and revenue. But that’s the truth of the matter. So you’ve taken something, you’ve been part of the team that’s taking something from high risk really uncertain to, 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 10 journey? Well, if you were there a year and a half, you know, again, a small portion of your options invested, 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 skis in terms of valuation, so instead of, and you might just get fired, by the way, because the two to 10% is likely going to be different than the 10 to 30%. So instead of this structure where you’ve contributed a massive amount of value, and have not really received anything commensurately in return, what if at the moment that you hit 10 million revenue, or 8 million in revenue, you get a $250,000 cash bonus, instead of the points 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 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 startup, 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 do all 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, unlike the last part of compensation, and the thing that I just I 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, I don’t, you know, it’s okay, if you fired me after 10 months, but it’s much better if I’ve 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. You shouldn’t, it’s not we are not interchangeable. And I’m not quite 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


Scott D Clary  38:48

I like it a lot. And I think that you know, I was actually going to bring up a point that you 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 tenure, you know, like me, 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 that has 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 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 the from 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


Sam Jacobs  39:55

the exactly right. And again, it speaks to the business model again. because we have, 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, you know, 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 SDRs report to? Or, you know, how should we set up the comprehension to be meeting set or meetings held? But where do you go to figure out, you know, 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, cuz I do these calls every day with members? The woman will does this sound fair? I said, No, it doesn’t. It’s not fair. It’s not right. And there’s, there hasn’t been, that’s what you want. You know, that’s the thing that’s helped. That’s the thing that will 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 Round Capital, or, 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 counsel 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. And 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 in, he puts together 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 full 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, they that that happens, and then they say, No, 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 here 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. Alright, 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 right. How did that happen? That’s because we were interviewing the 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, all the executives got the term. So you know, I just they said, anybody out there listening, or I know that it feels scary. And it should, again, remember all of this, it gets 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, you should know that things can be changed. If they want you bad enough, things can be changed.


Scott D Clary  43:28

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, it’s something that you’re right, I’ve never heard of it before. I’ve never heard of a group that does this 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 when when COVID is maybe a little bit two sided, 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 it top of mind right now. Right as they go into potentially new new work environments. Like hopefully, the economy is turning around a bit. Now a lot of people were laid off. So this is when they have to exercise that right if they 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 draw 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?


Sam Jacobs  44:45

No, no. You know, I think I’ve if folks are intrigued or interested or you want to learn more, you can go to revenue, collective comm. There’s an application process you click on 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, we’ve got 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.


Scott D Clary  45:28

Very good. Now, in terms of the evolution of these executive roles within organizations, it’s something that you’re understanding all the time, they’re looking for new ways to improve how an executive can transition and negotiate into a new role, as well as just other ancillary topics to help them be successful in their role. What what are you curious about? Or what are you investigating in the 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?


Sam Jacobs  46:09

Well, I don’t here’s, here’s one thought, this 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 weights 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 yeah, 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, I think more people should investigate coaching, hiring coaches, as something is 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, you know, mental health is incredibly important. And so it’s not about it. 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 from traditional talk therapy. So you know, 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 rant very rarely goes. But I don’t believe that I don’t want the company to buy my computer. If I were to ever work for somebody in which I you know, hope not to. But if I ever heard or for somebody, again, they’re not buying my computer, 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 terrible like your advertising, particularly more experienced people, sometimes your advertising your age, when you put together decks that just look like absolute dogshit. And you’re like going into a final round interview, just look like grandpa or grandma don’t want to do that. So you need to surround yourself with an arsenal of resources that are dedicated to you evolving as human being not about the company’s 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 a baseball player. So they all have their own weights 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 transactionally 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 collective.


Scott D Clary  49:48

Do you find that 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 it side 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 on this, you know, I’ll just expense it all this is part of the company, they should be paying for this, because you’re paying for my coaching my executive training, do you find that more executives are just taking that initiative on their own to take control of their own career?


Sam Jacobs  50:17

I hope so. I hope so. They 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 you’re just like, well, I won’t do that, unless I can expense it, you’re just shortchanging yourself, 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.


Scott D Clary  51:03

That’s very powerful. That’s 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 is an effective view of career. I think it’s, you know, I see a lot of people that try and build, you know, we 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 team working for you. Basically, essentially,


Sam Jacobs  51:34

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, and we need to prepare ourselves for it.


Scott D Clary  51:50

Yeah. And to be quite honest, if you if you aren’t transitioning from jobs every 18 months or or even if you are and you’re better protecting yourself, the the expenses will pay for themselves. So exactly. It’s It’s It’s It’s it negates 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


Sam Jacobs  52:21

I biggest one is, you know, I always say the person that takes their life seriously, the soonest is the person that will win my I can probably think of a more pithy way of saying that or articulating it, but like, I, the problem with me, as a human being, and to the point of like division 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 can 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 wished 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 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, taking 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 makes sense sometimes to say those things.


Scott D Clary  54:01

No, but but it may not make sense to to your younger self, you know, when you when when you were younger, but if somebody’s listening, hopefully, hopefully they take that to heart. It’s all you can tell you can help 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, and up to and then last question before I get some websites and socials from you. What does success mean to you?


Sam Jacobs  54:38

I wish you know the thing about cliches is that they’re true. That’s why they’re cliches. For me, 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 my, 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 I’m 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 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.


Scott D Clary  55:53

Very well set. And most importantly, where do people connect with you? Where do people go find out more about the revenue collective? Give me some links that you can go check out.


Sam Jacobs  56:03

Sure, as I mentioned, so first, if you want to email me you can, Sam at revenue collective comm maybe mentioned that you heard me on the podcast that would help if you want to check out revenue, collective revenue 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. forward slash the word in Ford slash Sam F Jacobs. Those are the those are the big

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