Navigating Sales Leadership for Early Stage Startups

Speaker 0    00:00:01    Coming to you from Orlando, Florida, Orlando, Florida, and streaming around the world around the world. You're not tuned in to the sales samurai podcast. The only B2B sales podcast, providing unfiltered unapologetic views and tactics directly from the sales trenches. Here's your host, Sam Capra.  
Speaker 1    00:00:30    Welcome to episode 13 of the sales samurai. I am your host, Sam Capra. Thank you for listening and do us a quick favor. Take a moment to subscribe and download on today's show. We're going to be discussing navigating sales leadership for early stage startups. So this is for those individuals out there that are looking to make the move potentially make the move as a VP of sales, head of sales for early stage startup. This is a podcast you have to listen to. What are the challenges we're going to discuss with those challenges are facing that role as well as how to set yourself up for success. Long-term success from a career path standpoint, and I actually have a fantastic guests really kind of help us tackle this. Uh, Steve is a three time startup sales leader, mostly running revenue teams for high growth startups ranging from seed through series C. So he's seen it all from a leadership standpoint and about a year and a half ago, Steve traded in his employee hat to launch two companies magic desk, and Redditers magic desk is an it solutions provider that works with other small and mid-sized businesses while rennets has, is a sales consultancy who primarily works with early stage startups on all things, sales strategy, tactics and execution. Steve, how are you, man?  
Speaker 2    00:01:45    Good. How's it going? Sam  
Speaker 1    00:01:46    Man. I'm super excited to have you, man. I heard you a little wet up there in New York, the New York  
Speaker 2    00:01:51    Area. I brought my snorkel in with me, so I think I'll, I'll get home just fine. Yeah. It's it's wet. That's awesome,  
Speaker 1    00:01:59    Man. Hey, well, I am super pumped to have you on the show. This is a conversation we've had a couple of conversations offline and this actually this topic I don't like to do it unless it's relevant to me, but this one really hits home because obviously I'm in a position with a startup as the head of sales. And so what we're going to be talking about today is really the challenges facing that VP, whatever that cop line sales position is at an early stage startup. So we're going to talk about the challenges and really tips as an individual going into that role that you should be really making sure you're setting proper expectations as well as on the company side, setting that individual up for success. That's what we're going to be talking about. Super excited. But before we do tell the eyes a little bit about yourself, Steve, cause you have a, a really great background, a very diverse background, kind of give us a little insight into your background, Steve.  
Speaker 2    00:02:56    Yeah. So my name is Steve <inaudible> from New York. I have a nine year old dog named Mickey. Who's a part of every one of these that I do. He goes everywhere with me, but topically, I mean, I I'm a three time startup sales leader, you know, everything from see-through series C stop at the enterprise as well. You know, I've, I've, I've carried a bag, I've been an individual contributor. So I know what it's like to be in the trenches have done it. I've done it well in some respects. And in other cases, you know, it hasn't gone as well today. What I do. So I, I traded in the employee hat I'm now I launched two companies about a year and a half ago. I figure, you know, so much fun doing one might as well do two, right. And what they are they're, they're largely different, right?  
Speaker 2    00:03:34    So one of them is a company called magic desk. I'm co-founder CEO of we're an it solutions provider that works with other small and mid-sized businesses. And then the other, because I love sales for early stage companies is readiness. And what Reddit is is, is that we're a sales consultancy. So much of the current stable of clients that we're working with. And I think this will probably carry on into the future. Are those early stage folks, right? Companies that are shifting from founder led sales into something a bit more predictable, more professional, you know, that helps them get to that series a that's series B. So we do everything from like strategy tactics, roll up your sleeves, execution and diverse set of clients. You know, SAS is something that, I mean, you know, this better than I write has the power to really impact so many different parts of a company as far as what you can bring to market. And it's a, it's a really diverse group and we're having a lot of fun.  
Speaker 1    00:04:26    That's awesome, man. Hey, talk to me a little bit about, I always loved these kind of these origin stories from an entrepreneur standpoint. Like there had to be something that sparked, Hey, I could do this better, which sparked relative to us, like there's something that's not in the market that I think I could do better. What was kind of the epiphany or the spark for relatives?  
Speaker 2    00:04:45    Yeah. So there's a few things, right? I think that if you spend enough time in the early stage game or just the startup ecosystem in general, right, you see yourself in one of two lights consciously or subconsciously, by the way, one of them is I love this stuff and I'm going to be an employee and just attach myself to the right rocket ship and ride that, you know what I mean? Which is a great thing, by the way, I don't want to sit here and say that like, that is not a great path for someone to undertake, but the other side is like, Hey, I actually, I have this entrepreneurial bug that has just been, the fire has been lit by being a part of this ecosystem of, you know, working with this company or several companies. And I recognize that probably like six years ago, you know, while I was still an employee and, and, and for me it was one of those things where I had a lot of friends that were like leaving their corporate jobs, going and getting an MBA.  
Speaker 2    00:05:34    And I kind of laughed at it. I was like, I'm getting a paid MBA right now. Like I'm being paid pretty handsomely the right to solve real business problems. So this was my education, you know, working with startups at those very early stages. And I made a very conscious effort to sort of like filter in the good, but filter out the bad. Right. You see a lot of good stuff happening, but you also see the other side of that. It's like, if I'm going to start my own company, I'll never do that ever again. And I committed myself to like the education of leadership and running a company. And I kind of just like out to this inflection point where it was the right time, right. Partners, right opportunity. And that's where magic desk and Reddit as sort of came to be. That's awesome,  
Speaker 1    00:06:16    Man. And I know you kind of said this a little bit. I think you've touched on it, but what's been the biggest learning that you didn't expect and launching two businesses, but let's just focus on like, like, right. It's just like, what was the biggest thing that was like, we didn't anticipate it. Maybe there's a lack of sophistication on the customer side or just something internally. What was the biggest? Yeah,  
Speaker 2    00:06:39    So it's interesting, right? Because, so my big thing is, is like I know my lane, right? My lane is sales and sales leadership. That's what I'm good at. When you start running your own companies, right. Officially or unofficially, I don't care what it is. Like there are all these other elements that never were things that like, you had to really understand 360 degrees that now all of a sudden you look around the room and you're like, well, it's me, right? Like I'm the only one now who asked to be able to figure these things out. So it's everything from like legal HR, billing, invoicing, there's a million things, right. That, that you just don't really think about in your day to day as a salesperson or a sales leader, you are, once you go and you launch your own company, you're like, whoa, there's like, I got to learn.  
Speaker 2    00:07:24    There's a learning curve here. So it's been, I don't want to say it's been fun entirely. Right. Because I think that would be that that would be fake, but it's been enjoyable from the context of like, I know when the right time to like re wave the flag and be like, I need to ask somebody who really knows this stuff. And I'm quick to do that. You know, I don't want to spend a lot of time trying to figure out employment law. You know what I mean? Like I know people who practice us, so it gets best left to those professionals. That's awesome, man.  
Speaker 1    00:07:55    So kind of another origin side of this story. I know you, I know you've mentioned, Hey, you've been doing sales, you've been in the trenches. You've been a contributor. You've done those. I always like to ask what was the very first sales job? Like what where'd you where'd you cut your teeth at? What was the very first sales gig you had?  
Speaker 2    00:08:10    So this is a good one. So even take a step before that, right? Like I graduated from college in 2010. I studied business management at Bucknell university. And like, when you graduate from school, like it was sorta like the expected path. It's like, what do you do? You can go to law school or are you going to work on wall street? And I took the LSAT. I didn't do as well as I wanted to. And I was like, you know what? I don't even want to go back to school anyway, at this point. So what do I do? I go to wall street. I had a buddy of mine who was also, he was on the buy side. He was in the investment banking program over at Citibank. And he got really involved in the startup scene here in New York, which at 23 years old, I have 22, 23 years old.  
Speaker 2    00:08:48    I had no idea even existed. I thought, well, the only startups in the world were in San Francisco as far as I was concerned. So he started getting like hyper involved and it lifted the veil for me. I was like, man, this is so cool. Right? Like what's going on here? And I made up my mind at that point. I was like, I've been doing this for three years. I want to go to a startup. And I want to go somewhere that will let me sell with no formal sales training whatsoever. So I joined a company and there I was hire number 19 or 18 called mojo motors. And mojo motors was an automotive marketplace that sold to car dealers. And it was all used inventory. So we attached like the follow feature, the way that we think of following people on social media, we gave consumers the ability to like follow cars and they get price alerts, similar inventory being added, but we were selling to car dealers.  
Speaker 2    00:09:41    And what a while? I mean, I opened up like, I think 28 different markets while I was there. Everything from like Texas to DC, to California, every, and you realize like the communication structures with people and like the pace with which people speak, I'm a new Yorker. I speak fast. Right. And I learned real quick down in Houston, that doesn't fly. So it was, it was a lot of fun, but I was, I was good, but I was good. Not because I had any idea what I was doing. Right. If you asked me at that part of my life, like a sales art, or is it science, I would have smiled thrown you one of these. And I would have been like, it is totally art, man. You either have the gift or you, and it wasn't until I went. And, uh, I joined Gardner actually unbelievable place, by the way, for anybody that's like considering sales as a career, I am someone I was there for two years, gardeners and unbelievable organization that will teach you what to do, how to do it. That was the first time in my life that I was like, wait a minute, there's a method to the madness. So that was when I became dangerous at that point. That's awesome,  
Speaker 1    00:10:48    Man. Yeah. It's funny. And I've had this comment. I typically ask that question every podcast, because I hear it across the board. I've hear people that have sold steak knives store to door, rainbow, vacuum cleaners. And I've heard some, some awesome stories that very similar to kind of the story you were sharing. And what I have found is those things really define you. Like you're going to evolve, you're going to change as a sales rep. Hopefully you're going to get better, but the core fundamentals, how you approach hunting, how you approach cold, calling, how you approach urgency, whatever it might mean. Typically that's hardwired into you. Based on some of those positions you had when you were cutting your teeth to figure out how to be better. Like, what is this sales mumbo-jumbo that I'm trying to learn and get better at? And so I always like to hear that, but Gardner was really where you found the training piece of it to your point to be absolutely dangerous. I put the science behind the art. That's fair to say, right.  
Speaker 2    00:11:48    Completely covered. But you raise a really interesting thing because I don't care if you're a professional sales person or not. Right. Everybody, I don't care if you're an engineer or developer or you're an operations or a lawyer. You're an accountant. We're all selling ourselves every single day, right? Like this is something that whether you are paid to do it or not, right. You whether, and whether you want to believe it or not, you are telling yourself every single day in almost every single interaction that we have socially, professionally, what have you. And I attribute, I think a lot of what you talk about that DNA, that those are those things that are hardwired into you completely predating any professional experience. Like I played sports growing up, you know what I mean? Sports teams, sports in particular teaches you how to operate within a team, set a goal goal and achieve it practice, right? Like this notion of showing up every day and trying to get 1% better. Those are all things that I think forget being a professional salesperson or not like it started as a kid, you know, developing those skill sets. That's cool. Man  
Speaker 1    00:12:53    Talks about, I actually asked this question on one of my last podcast. I thought it was, it was a good question. Cause it got some, some, some mojo kind of work in, so you've been selling. How long now, Steve, how long have you had the sales hat on tech? Like  
Speaker 2    00:13:06    10 years. Yeah. Almost 10 years.  
Speaker 1    00:13:09    So 10 years it's been a long, that's a good long stretch. Right? So what have you seen? What's been the biggest change in sales in the 10 years you've been doing it. I want you to answer this in two ways. One for the better where it's like, Hey, I've seen a great improvement here. And one actually for the worst, I I've actually think that went the wrong direction or maybe a version of it went the wrong direction. So I'd like to get your thoughts in the 10 years what's improved. What in your opinion has not gone the wrong way. Knock on the road.  
Speaker 2    00:13:40    I love this question by the way. Right. And I think it, we're going to answer two sides of the same coin, starting with technology, right? Technology has evolved so much in the last 10 years. We all know it, right? Like I'm not telling anybody something that they don't already know. And I think when you talk about CRM, sales, automation, uh, intent data, right? The, all these new ish things that are at a sales person's fingertips are so powerful. Right. And leveraged correctly. This is something that if you, you ask somebody who's been selling for 40 years, by the way, right. Like what they used to do, they used to grab a phone book, rip out a few pages and just go off one by one by one, right? Like that's what people did the ability to be targeted and thoughtful and both effective and efficient in what you do because of what technology affords us nowadays is something that those guys and gals of yesteryear would have died for.  
Speaker 2    00:14:36    You know what I mean? Like they would have loved to have this sort of tooling at their fingertips. But on the other side of that coin is that like, people are now using this technology to be lazy, right? It's like they just press play on a sequence and wait for people to respond. And it's like, that's what we do. You know? So it's de humanized, I think a lot of the day to day for folks that are boots on the ground, like frontline salespeople, because they're being handed these playbooks from sales leaders that are just like, eh, you know what, we're going to have 4% conversion at the very top of the funnel. At least we know we have our meetings and like things work, you know what I mean? They're good enough. And I think that people are just like resting on those laurels of saying, we're not going to bring the human element. Like how do we compliment the technology with the human element of who our people are and why we hired them in the first place. Those are the two entering starts and ends with technology. I think,  
Speaker 1    00:15:32    I think it's a fantastic, you know, and the more and more I've asked that question, I almost get a very similar answer from most people in the space. I've been doing it a long time. Right? The common denominator is the technology and you're right. It's, uh, it's the devil, you know, kind of rock and a hard spot. And where I've thought where I think technology has been fantastic. But the positive is it allows you to scale and drives efficiency. Boom, great stuff. To your point. Instead of making 10 calls, I can make 400 calls through like a connected and cell or an Orum, those types of solutions. Awesome. But the flip side is it's created an exorbitant amount of noise. Like everyone's getting 500 emails now everyone's getting a thousand phone calls. So it's the duplicity of technology to your point, positive on one side, completely net. I don't want to say completely, but there's a challenge on the flip side of the noise that it creates as well.  
Speaker 2    00:16:27    I was just on a clubhouse talk actually yesterday. Right. And I was explaining to, I was on the panel. We were answering questions from people and we were talking about this notion of like multimedia outreach, right. And to grossly over simplify it, you have email, you have phone and you have social and email to your point, right? Like I've always looked at email by the way, because I know, I know what my own inbox looks like. Right. Email is my way to just put my name, put my company on your radar. I expect very little to be honest in terms of positive replies and meetings. If I do, it's like a, it's a gift, right? 85% of the meetings that either my company, my companies, I should say my clients and, or as an in-house employee, when I was running teams, there's discovery meetings, wherever they come from this, the old fashioned, the most old fashioned technology and it was used. Right. And that has been such a powerful thing because people are afraid of the phone nowadays. And that's when we talk about, Hey, how do we use technology? But add that human element, pattern, interruption, get somebody smiling, be yourself, flash. Some of that personality, something that makes you uniquely you is such a powerful thing. Such a powerful thing. That's cool, man.  
Speaker 1    00:17:40    Hey, so let's shift because this is kind of why we're here. Sales leadership for early, and this is getting really micro. So for the, I think this is good because this is actually a topic that's been requested from my circle of people. A either saying, Hey, I want to get into SAS B. I want to get from enterprise in the startup sale. I want to be a leader of a startup. And how do I do that? A and B what should I be on the lookout for? So I want to get your feedback, Stephen, why I think this is so important, just kind of lay the groundwork. And I'm hoping you might be able to piggyback off this. The reason why this is a micro topic, but so important is because if I'm not mistaken, SAS is the leading industry in growth from just an expansion head count revenue. Like it's either number one or number two, don't quote me on that. But it's, it's pretty far up the totem pole of  
Speaker 2    00:18:35    What's the saying software's eating the world.  
Speaker 1    00:18:37    Exactly. Right. So these positions, these startups, and we all seen those marketing landscape technology has grown from 1000 to 9,000 to 24,000 in the marketing tech stack and sales tech stack is a whole other category that these startups are now to your point, they're, they're ready. They think they're ready, or they're at the point where they want to start scaling and bringing on a VP of sales. So I want to get your opinion on is there's some inherent challenges for that early stage startup and that specific position of bringing on a sales leader. What are they in your opinion? Like what are the biggest challenges facing that role? And if you want to take a step back, if there's something else you want to add,  
Speaker 2    00:19:21    Well, there's a bunch of things, right? Like there's no one size fits all answer to any of this, but like you bring up something, I think really relevant here. Someone that wants to go from the enterprise to a startup, guess what? At the enterprise, man, there's a good thing going like, there's a, there's a known method to the way that you operate everything. Is there. They understand the value proposition, the, the ICP, the different use cases. They understand what resources to draw in internally. When something, when a question gets asked, I don't need any of that stuff. And Steve, on top of that, they have money. Yeah. Right. And then there's this like never-ending pool of money, right? Like it's a beautiful thing. You don't have any of that stuff at a startup. Right. Like any of it. And I oftentimes like, I'm a baseball guy, by the way.  
Speaker 2    00:20:05    And you think of the difference between like a major league training facility and like a JV high school. Like that's kind of what you're, you're thinking like think of the, the training facilities between what the New York Yankees get to walk into every single day and some no-name high school and like the Moines Iowa, right. As to walk into every day, they're totally different. So it's, you know, the idea that you are just going to be able to like pack up your bags, walk into, walk into the startup's office and like save the day. No, like that's not where the work starts. And certainly not where it ends writing the playbook for the first time, understanding how to build a culture of collaboration between sales, marketing, operations, finance, et cetera. Like those are all really tough things to do. And the other side of that coin too, is like, I don't know that founders and or their boards are doing a sufficient enough job of being able to understand what the right skill set and who the right people are to be able to bring into that sort of environment.  
Speaker 2    00:21:04    So it's a catch 22, where on the candidate side, you might be looking at it and saying, Hey, this is going to be the next Stripe, the next, you know, name brand company drop it, right. What a juicy opportunity. And I get that VP title. I get the head of sales by all. Like people are doing things I think for all the wrong reasons on the candidates side. But then equally on the other side of that equation is you have founders and boards who are like, we're going to throw these kids, these unattainable KPIs out at this person that they are going to, they're so good at sales that they're going to be able to solve for. And it's just like, it's bad math. At the end of the day, I have a really hard time bringing those two things together and looking at it in a Petri dish and saying like, this is a recipe for success. So I'll pause there for a moment. You almost  
Speaker 1    00:21:52    Frank bring up a no win scenario there. And what I mean by that is I'm an enterprise guy coming from Salesforce. I have all the processes, playbooks money resource, lead engine, everything I should need as a sales individual to thrive. Now I'm not giving them all the kudos. They're a great organ, but they ha it's a well-oiled machine. And the thought process to your point is I want to jump on the startup and be a part of the next big thing. And I want to kind of make my name on the startup scene. And so enterprise to start startup. And it's funny because you don't know, I made that shift and it wasn't an easy shift at all. It's probably the hardest shift I ever made, but there's that misnomer from the candidate. I can do that because I've done Salesforce. And then from the founder, they think, oh, well, he comes from Salesforce. He has all the knowledge process. He'll just bring that to us and both are wrong. It's not just as easy as taking Salesforce and stuff and implementing it. That's a whole different dynamic to your point. And that's a whole lot just in just a top track and being able to develop it. And so both are set up on unrealistic expectations, like what I'm really bringing and what I think you're bringing. They're two different mindsets. I think  
Speaker 2    00:23:09    That's some of the, I don't mean to cut you off, but like those puzzle pieces fit by the way, right? Like, listen, I'll speak from my own experience. When I went, when I came back to New York, after Gardner to join a startup, there were so many things that I took with me from Gardner that I put right to use. Right. I lit the world on fire for the first, like three to five months that I was there before I hopped into to a leadership role. But just doing those things is grossly insufficient, right? Like if you think of a hundred piece puzzle, right, you might be able to take 60 of those pieces and make them fit inside inside of that ecosystem, that, that new startup that you're at. But guess what? There's still 40 pieces that like, you should just throw out and you need to start from scratch on. And it takes a certain degree of humility, vulnerability, the ability to raise your hand, say like, Hey, I don't know what I don't know. And take some of those best practices that you're bringing with you from the enterprise and just molding them in a way to make it really fit the, the startup that you're in and who you're selling to.  
Speaker 1    00:24:16    So let me ask you this, Steve, on that point, because what we're talking about, maybe the little bit of the disconnect too, you said there's some things that are transferrable. Like it'll get you past the first three months, then it's a whole different ball game, but like kind of what is the, self-check you think, as a sales rep, as a sales person looking to make that change, like, what is the self diagnosis you've really got to go through? Hey, do I like building plate? Like what does that analysis you have to say, am I set up for success? Just walking into a position like that? Like, what's your thought process?  
Speaker 2    00:24:46    Yeah. Well, so like, let, let's, let's call out one thing first and foremost, you're the first sales hire. You're the VP of sales. You weren't managing anybody. Right? So this like notion that I'm in sales leadership. So I don't have to do the grunt work associated with like prospecting and discovery calls and like we'll, and we'll circle back to this, by the way, cause this is something that's in sales leadership that like drives me insane. But the reality is, is like, if your expectations are that you made you've quote unquote made it now and like, you don't have to do that frontline sales work that you're entirely wrong. So if you think, if you have this self view of I'm past that in my career, making that sort of jump is not for you like a hundred percent, not what you should be doing. This is square peg round hole.  
Speaker 2    00:25:33    Hard-stop the other piece of this is there's a lot to be said about like work-life balance. And the reality is, I don't know about you, but like there are times I'm on 24 hours a day, you know, and that sales leadership role at the early stage company, founder wants to talk to you at 11:00 PM at night, you're dozing off to sleep. Guess what you're getting on the phone. It comes with the territory. So this isn't the nearly as like glamorous, as I think a lot of like salespeople, we're really good at like talking about the things that are really great about our lives. Like we're so good. We win every deal. We, this, we, that it's not nearly as glamorous as I think a lot of people will lead you on to believe. So when we talk about like the evaluation of that jump, you have to take a really good, hard look in the mirror and say, Hey, am I willing to do the grunt work?  
Speaker 2    00:26:20    The does development of a scalable process in playbook excite me and M I K have I done it before? Cause that's a big thing. Like you ultimately have to do it for the first time at some point, right? But it's hard. Like you're putting your name on conversions and like planting a flag in the ground and saying like, this is what I expect to be able. This is what I'm committing to being to provide to the business. Just a difficult thing to sign yourself up for. Right. And I do think it takes a special kind of crazy, right? To want to build a playbook from day zero, with nothing at your fingertips and put your stamp on it. You know, like this is Steve's, this is Sam's. This is the process that I think is going to the process. And the framework that I think is going to get us from where we are today to where you expect me to be without knowing any underlying data, right. About what we can expect.  
Speaker 1    00:27:13    So with that in mind, so let's say I've made that determination. I'm ready to make that shit like, Hey, I'm willing to grunt it out. I'm still going to carry the bag. I'm really not leaving anyone out. I'm going to build it. I'm going to build the process. I'm going to build the playbook. So I'm going to do those things that I know I have to do. I think I'm either ready or willing to take that challenge, but where's the gap between the candidate jumping in and saying, okay, and what the, what the company's actually bringing to the table to actually support them in that endeavor. Cause that's a big, even that alone. There's a big disconnect. It's in my opinion,  
Speaker 2    00:27:49    Clearly I think there's a few things I think in this vein that really stand out to me, right? And the venture back model is putting new incoming sales leader at a dramatic disadvantage. You don't need to look at the underlying labor data or employment data to know that there are some really incredible salespeople that are turning in and out of leadership roles every single day, turnovers, it's, it's alarming. Right. But what's going on. It's like every day I feel like I get a new alert from somebody that's leaving a job and going somewhere else, whereas leaving a job and is looking for the next thing. And they're all good people too. Like people I know personally that are like really, really talented at what they do. So it's a long-winded way by the way of me saying that the expectations that a lot of these sales leaders are walking into are just on attainable.  
Speaker 2    00:28:43    I don't care how good you are. Right. So it would be who view, I think as a candidate, not to a negotiate the hell out of your offer, number one, right. Get commitments from them commitments in terms of time, a leash that you get to run with. I mean, you're seeing people like 30 days enroll, all of a sudden they're like on pips. It's like, what, what do you like? They just joined. How can they even know what, what like, who they're selling to or what they're selling? So I think it would be whoever the candidate is not to negotiate the hell out of their offer. And when you think of, I mean, let's assume for a second average tenure right now is like nine, 10 months. Right? You haven't invested in any of your equity at all. It's a black eye on your resume, right.  
Speaker 2    00:29:27    A short tenure. So why wouldn't you? Right. And the questions that I would be asking today are, so are, are very rooted around resources that the business is going to invest into your success. And I don't mean from a sales tech angle, I don't necessarily even mean that from a headcount perspective, I'm talking about a, the marriage between sales and marketing. Number one, what is the company going to invest in marketing resources, inbound, SEO, content, things that you know, can pay some immediate term dividends, right? As you're ironing out that process and your go to market strategy on the outbound side, and then things that are going to read benefits in the medium to long-term right, with organic search and showing up on page one and getting people to raise their hand, you know, understanding that. And then B is what about outside resources, right?  
Speaker 2    00:30:16    If you're going to be like, if you're not doing that, you're going to be on an island. And I have a really hard time feeling bad for you when you're on that island, because you didn't ask, right. You are, it's good. As you may be as prepared as you may be. I, again, I think it would be who view not to ask for outside resources for leadership development, for helping you fill some of those skills, gaps, gaps, and knowledge gaps of things that you just haven't been exposed to to this point, irrespective of how well you've done. We need to ask for those things upfront and get commitments from the, from our would be employers so that we can put ourselves and the company in the best place to be successful, right. In achieving those difficult goals. Right. Really at the end of the day, that's what they are.  
Speaker 1    00:31:03    Would those be non-negotiables in your book? Like, Hey, I'm just picking a number. I don't even know if we quantify it this far when we're having that conversation, but is it something you would say, Hey, I need outsource resource. I need leadership development. I want to go to three conferences a year, whatever those, whatever the ask is, is that a non-negotiable for the interview? Like if they're like, Hey, listen, we can't commit to that. We don't know if we have enough runway. We don't have enough resources are running extremely lean. They have to come out of you professionally. You'd have to do that on your own, uh, your own, like, are those things non-negotiable in your books? Or does that just tell you enough that they don't commit to it? Like, Hey, you better run for the Hills. That's not an opportunity you want  
Speaker 2    00:31:44    To be it's so situational, to be honest, right. I'd be pushing for a budget is my thing. Right? Like give me a leadership development budget and I'll find out a way to max it out, right? Like all hon high, low on a Gaucher even to get the right resources in there to help me help you really, at the end of the day, that's what this becomes is a non-negotiable maybe, maybe not. I think it depends on like what you've done prior to, and like your training background and like how well that transitions from where you've been to where you're going. But I don't see enough people doing this at all is I think the big point here. And if it's not an indication, by the way, let's say you do get the response of, you know, no way. It's not like we're bringing you in because you're supposed to have all the answers.  
Speaker 2    00:32:32    That would be a massive indicator to me that like, if I don't do above and beyond what they're asking me to do, which I already know is going to be super challenging. There's no loyalty to me. You know what I mean? I'm supposed to be the genie with, with all the answers. And that should, I think, tell you enough, right? On the evaluation side as a candidate to be like, you know what, maybe this one, this isn't the right one for me, this isn't the right culture for me to, to, to join. So I dunno,  
Speaker 1    00:33:00    I think those are great catches because, you know, I know in doing this and I think I've missed some things through my three or four startups, I've been a part of, you know, you get hung up in the, in the salary, you get hung up in the stock options or equity. You get hung up in the benefits and commission and a lot of those things that you don't even think of, which I'm glad we're having this conversation. Hopefully there's someone listening to this, like, Hey, I'm going through this. And I didn't even think about asking for that. So I'm hoping this helps someone out or multiple people, but those are things that looking back on a couple of that, if I would've just taken the step of, I just transitioned from enterprise to start up, didn't even think about, you know, budget for training and development. I just thought, Hey, I have to learn on my own and figure it out as I go that that's just the nature of the beast. And it probably put me back a lot further than I would have been if I would have just taken that extra step. So I think you call out a good point there, Steve.  
Speaker 2    00:33:59    And it's one of those things like there's somebody I mentor by the way, super smart guy, unbelievably talented salesperson. And he just went to his first startup. Right. And it's one of those things that I told him this I'm like, you'll figure this all out, by the way, like there's nothing that me or someone like me is going to tell you that you won't ultimately figure out and learn on your own. But when you have somebody that's like gone through the challenges that I can bet the bank, you're going to go through helping you through to avoid those pitfalls. Guess what? It becomes a lot easier. Right. And I'm not saying that we should take shortcuts, right? Cause that's not. But at the same time, this isn't about like struggle porn. You know what I mean? Like it doesn't have to be as challenging as social media is going to lead you to believe.  
Speaker 2    00:34:48    So w why put yourself into that hard, difficult position? It's like, Hey, if I can give you the answer to the test and give you some of the answers to the test, why wouldn't you take that? You know what I mean? It's not cheating by the way, right. And your company, isn't gonna hate you for it. They're going to appreciate the fact they should at the end of the day, appreciate the fact that like, Hey, this was somebody who was willing and vulnerable enough to be like, I don't know the answer to that. Let me go to someone who's done this before and get this right. The first time, as opposed to putting us behind the eight ball for a quarter or two quarters, three quarters,  
Speaker 1    00:35:20    You hit the nail on the head because it just comes down to the time. Right? That's the finite thing that we only have a certain amount of, like everyone has the same amount of time, right? So if I can help you get to somewhere within six months versus you doing it on your own and not figuring it out until 18 months, I've just saved your 12 months of heartache pain and lack of hitting certain metrics. I think that's awesome, man. Hey, so here's the other side of that. Okay. I'm negotiating as a, as a candidate. Hey, I need this, I need that. But there should also be, I think this is fundamentally missing and it might rub some people the wrong way. I truly believe the some founders, probably a good majority managing expectations of the board because you know, we all know startups need to double every year and all these metrics that they got to hit, whether it's product market fit or not, who cares, you still got to double every year. Like all these things that go into this perfect storm of, is it realistic or not? Like what role is it of the founder or the leadership to try and set realistic expectations? Hey, your, your, your quarters, 15 million. We have a run rate of a 1 million like, come on, like, come on guys. That's not even realistic. Like there's gotta be something that falls on the founder and that team to set proper expectations with the borders that just not possible, Steve, in your estimation,  
Speaker 2    00:36:41    I think they should. Right. So it's, it's literally, it's a same side of it. If you're a sales leader, right. And you're joining a company that's done 500 K in revenue and you're, you know, you're being hired to get them to 50 million, just to throw a ridiculous number out there, 50 million in the first 12 months. It's like, well guys, like you, I think it would be foolish, right. To sit there and be like, yes, I'm so good. I'm going to get us, you know, I'll, I'll go through the wall under the wall, over the wall. It's the same thing with founders in their board. Right. So there, there needs to be, I think real honest communication and the, you know, the come to Jesus moment, if you will, around what's real, what's attainable and what's not given current state and current resources, you know, and it's funny, you say like doubling every year, like I've been a part of environments where it's like triple, triple, triple, double, double, you know what I mean?  
Speaker 2    00:37:35    If we're not doing that, we're failing. And you know, you get to 2.7 X and you're like, damn, that's a pretty goddamn good year. So far that that we've had. And it's like, Nope, we still have more to go. The short answer to your question, right. Is like, yeah, I think founders need to do a better job with their boards in setting those expectations in a way, because what do you do? If, if not, it's like you just have this revolving door of talented person after talented person, after talented person coming in, trying to do something, not having enough leash to be successful. And all of a sudden, you're two, three quarters down the line. It's like, well, that didn't work onto the next, right. What's the culture as the founder that you're trying to create in bringing people in and out of that sort of environment every single day.  
Speaker 1    00:38:25    So let me ask you this Eva kind of pivoting a little bit, because you brought this up a little bit earlier, so let's say I step into this role. I negotiate some development moving in that direction. If you're stepping into the, to a VP of sales role for the first time you're learning as you go, you're doing some development, like what is the basic blocking attack? Like you're like, listen, if you're going to spend time, like these are the core things that you've got to start on day one to ensure success, to ensure you're moving in the right direction. Is it process development? I'm sure. I know a lot of this stuff runs in parallel. Steve head count. You got to bring on, like, I know there's a lot of parallel, but there's got to be the foundation. Cause you brought up marketing. Hey, can they help minimize the time while I build a process by getting some inbound leads in like, what are the basics that you have to start doing day one as a VP of sales, early stage startup.  
Speaker 2    00:39:19    So let's assume for a second by like most people that are candidates for these sales leadership roles almost across the board, by the way, our top tier sellers, right? They are good. You give them a prospect, right. A qualified meeting. They can, they can do the discovery, qualify them, negotiate and get the deal to the finish line. Right? What is the single biggest bottleneck of almost every single company that I speak to nowadays the very top of the funnel, right? So if you're day one, when you're joining that team, I think the first thing that you need to figure out is how can I scalably and predictably fill the calendar at the very top of the funnel, right? And in my experience, again, there's like differences depending on your deal size, who you're selling to et cetera, et cetera. But for the most part, the full calendar for our sales person is somewhere between four and five discovery calls every single day.  
Speaker 2    00:40:11    Right? I'd be sprinting to that, right. As quickly as I possibly can figuring out okay, for our ideal client profile, the different user and there could be a few of them, right? Cause there's different use cases for your software, for your product, for your solution, et cetera. I would be doing everything I can to figure out how can I fill up the calendar at the very top of the funnel? Because your conversion metrics from that point forward are going to be strong, right? Like you're going to be the frontline salesperson at the end of the day, in spite of the VP of sales title, like you again, know you're going to be able to qualify X percent when Y percent average deal size negotiability, blah, blah, blah, blah. But that is the single biggest thing. Right? And then once you have that, that to me is the point in time where you can come up for air and go back to your founder, your CEO, your head of HR, whomever, and say now is the time where I'm comfortable because I perfected that, that playbook of filling up the top of the funnel, I'm comfortable now to be able to bring on other people and just pour gasoline on this.  
Speaker 2    00:41:13    Right. And I'll continue to do the frontline selling, but if I can have 2, 3, 4, 5 of me filling up the, the very top of the funnel, now we have some, we have some chess pieces to play with. Right. But that to me is the number one thing it's at the very top of the funnel of setting discovery calls, whether that's some of inbound, outbound, I think outbound is the most predictable, easiest path to doing that. You know, nailing messaging, knowing process understanding of who the buyer is that I think is the single biggest thing, right. That that folks should be working on.  
Speaker 1    00:41:49    So you brought this up earlier. So I want to make sure we do dovetail back to it. Cause I think it's kind of tying into what we're talking about. So you're right. Coming in, don't get all high and mighty. You're probably, you're going to be selling you really never be leaving anyone. You're going to be actually carrying the bag, having a cooler, the whole nine yards. Like what's the biggest disconnect there sounds like you've seen those lot disconnects typically in that candidates expectation of that role, just to what I'm going to be doing. Day-to-day I was sitting behind a desk, you know, building out a process and that's it like, what's the thoughts around that stuff.  
Speaker 2    00:42:21    So I'm going to take this a slightly different direction, right? And if you are a rock star, individual contributor, right. And you have your eye on the leadership position and you think, but, but like helping other people get to where you've performed, doesn't excite you. Isn't the reason for getting up every single day, don't go into leadership. There's nothing wrong with that. By the way, I think that like there is far too much weight being put into the fact of like, just capping out as an individual contributor as a bad thing. Not for nothing. You're your highest performer on the sales side. Uh, month in, month out, quarter in quarter out should be the highest earning individual anywhere. That's my opinion. That's you should be making the most money. Right? So if that's what motivates you and that's what, and, and like managing people and helping them develop skills and even dealing with like the personal side of that too, right?  
Speaker 2    00:43:20    The human element of what it means to be a people manager at the end of the day, it doesn't excite you. You just shouldn't go into leadership because that's what the job is. By the way, when you do have a team, your quota, right, that you had as an individual contributor, just ballooned five X, right? You're not carrying a smaller, you're carrying a bigger number that you to some extent can be personally liable for. But at the end of the day, it's your people, right? Who are doing the frontline work more often than not. So if you're not willing to like roll up your sleeves, analyze data, coach, be an active participant on calls, listen to call recordings. Like I can't tell you how many nights, by the way, I just, I would spend every evening from 7:00 PM to 1130 at night at 12 o'clock in the morning, just listening to call recordings of my reps.  
Speaker 2    00:44:09    And then, and then getting up early in the morning, you know, walking into that one-on-one and having really tailored advice, pulling up a specific conversation that they may maybe have had two and a half months ago that they don't remember. Right. And being like, Hey, I hear you do this all the time. Let's listen to both sides of this conversation and start to develop you in a way so that you, this, this is one less thing, right? One less that you, that you have to deal with every single day. So that's the thing. It's not kicking up your feet and having people sell on your behalf and like, knock out your number for you. There's a real human element to this, that isn't for everybody. They think it is right because of the salary, because of the title, because of this, because like status aside, forget that for a minute, the actual work is helping, helping your reps and going to bat for them cross departmentally. Like that's another, if that doesn't excite you, like that's a core part of the role. So I think that's a big thing, by the way.  
Speaker 1    00:45:08    I think that's a good catchy because you're right. And especially as you've been doing a role for so long, it's almost expected why need to go into leadership now? Like, that's just what I need to do and whether I really want to, or not, or whatever the thought process is, maybe it is a status. Maybe it's an ego. Maybe it's a whatever, you know, I'd be willing to bet because I remember the old days of, well, they're a good salesperson. Let's just make them the sales manager or sales leader. And that was the thought process behind moving someone up. Like, and we both know today that that's not the case. Those are two different people that typically operate and are successful in those roles. But you're right. They've got to self-harm you got to take that hard, look at yourself, really figure out is that what I want to do? Like, because you're right. Like that quota is ramped up by five X. If I have five people, it's times five and to some degree, yes. Coaching, but you're ultimately on the hook for it, but you're not in complete control of it. Right. You haven't been to coach and mentor and train your team to go chase it and get it across the goal line. And that's, that's difficult for a lot of good salespeople who are very territorial a players. Right. Is that fair to say?  
Speaker 2    00:46:20    Yeah, it's that self motivation. Right. And the control element is the big thing to me. When you think of the control of outcomes, the biggest difference between being an individual contributor and a leader is control at the end of the day. Right? And the reality, like, again, if you think you're going to be the sales leader that just like comes in and saves the day on a sales cycle or something like, think about all the things that worked really well for you as a sales rep, you have rapport, you had credibility, you had trust you're the sales leader coming in at the 11th hour to quote unquote, save the day. You have none of those things, right? Your rep is the one that has that. And I've always said that this was something I I'm grateful for this self recognition, by the way, I knew I wanted to get into sales leadership, because for me, I recognize the power in not just having me be a lone Wolf, individual contributor, and going at it by myself, but to be able to create for 5, 10, 15, 25 of me, that was when I was like, if I can do this repeatably and scalably and predictably, my teams are going to be absolute killers at the end of the day.  
Speaker 2    00:47:28    And when that light bulb moment went off, when that connection was made, that was when I knew I was like, I want to be a sales leader. Right. And I'm going to do it. And that was the reason that I wanted to be a sales leader. And then you start to learn again, the way that different people are motivated have to connect that, like the way that I coach you is going to be very different than the way I coach something else. Because you get, you get up out of bed every day for totally different reasons.  
Speaker 1    00:47:51    Right. That's awesome, man. Hey, we're bumping up against it. So final thoughts, feedback just for the audience, like in this, as a leader coming into it, maybe as well, Steve, for those that are already in kind of the, in the fire Mo where they're in it, they didn't ask those questions. Like, what do you recommend for both sides? I think we've talked a lot about coming into it. Maybe what are some final thoughts for those that are like, okay, I didn't ask those questions now. I'm kinda in the midst of it. What do you recommend for them? I like, what's the, if anything, like what, what's the thought process for them?  
Speaker 2    00:48:26    So my business partner is famous for saying this, right? Is that like, if you signed up for this, it's not everything you thought it would be. You didn't fail. Number one. Right. You're still good. The reason that you were a candidate in the first place is you're good at what it is that you do, but you you've probably paid for a really hard lesson, right? At the end of the day, all is not lost. I think if you have a good relationship with the leadership team, good relationship with your founder, there is no shame. I don't think, or ego associated with raising your hand and asking for help. Like it's never too late until it really is too late. Right. So if you're not where you're supposed to be, if you're behind plan, if you're realizing that there are just things associated with the day to day in this role that you weren't prepared for, right?  
Speaker 2    00:49:09    Like raise those issues, ask for resources, ask for help and see what happens. Right. You didn't get the chance to negotiate it on the front end, but you know what, like give yourself the best chance to be successful by pooling in additional resources and asking for them. I think that's number one. If you're considering making that jump again, like the good, hard look in the mirror that this isn't, this isn't nearly as glamorous as I think a lot of people would lead you to believe and understanding. Am I prepared to either go back to carrying a bag, doing that frontline work in spite of my, my title, do I enjoy leading people right. Those writing process and coaching are those things that like are reasons for me to get up. Is that a, is that a good enough reason for me to be excited about work every single day?  
Speaker 2    00:49:52    If the answers to any of those questions is no again, that's okay. Right. But don't go after the sales leadership role, if that's the case. And the other side of that is if you are committed to doing this, or you're exploring it, negotiate the hell out of your deal, right? Get resources, marketing, professional development consultants that you can bring in, right. As either folks, you can bounce ideas off of ask questions of best practices. Has this worked for a similar type of company before? Has it not have those sounding boards, right. Internal and external that you can go to and make that a part of your compensation package. It's an investment in you and the company. Right. And getting a founder and CEO to realize that shouldn't be nearly as challenging as I think a lot of people perceive it today. And if the answer saw those things are no in return, again, freedom of choice. Right? Maybe this isn't the right opportunity. There will be another one. I promise you that. Right. So pick wisely is the big thing, because there are implications with respect to your resume and your candidacy for a future role, if you make the wrong choice. Right. So handle that with care. It's it's your life, your career.  
Speaker 1    00:51:06    Yeah. The only thing I'd add to that, and that's a great feedback is I think it's also your mindset into it, right? Because if you have a mindset of abundance versus scarcity, you know, there's another opportunity, right? That if this isn't the right one fine, it's not the right one. I'm not obliged to take everything. You've got to be selective specifically for that. Well, I think you got to be selective in any role, but for this role specifically, it's okay. You get four offers and you, three of them just don't line up. Or just whether it's culture fit. If they don't want to invest, expectations are unrealistic. Whatever the criteria are. I think alongside with what you're saying is you should have a list of just non-negotiables for yourself. Like if I, if this is just not doable, then that is a knockout for me as a candidate with this startup. And I think sometimes we lose sight of that.  
Speaker 2    00:51:55    Steve, we do it with our individual sales cycles, right. There's only so far that we'll go, we know what those guard rails are, why not approach our career in the same vein. Right? One of the elements of what's likely made you so good. Right. And a candidate for this role in the first place is something that again, it would be who view not to apply it to your own professional life and the way that you evaluate job opportunities. So I couldn't agree more  
Speaker 1    00:52:21    Without a doubt. So I see how do people connect with you? How they learn a little bit more about readiness the whole nine yards.  
Speaker 2    00:52:27    Yeah. So you can find me on LinkedIn. Steve Korn. Rajesh is not an easy one to spell. So it's K O R N R E I C H. Also. Welcome to shoot me an email. You can find me it's steve@magicdesk.io or steve@reddit.work. R E D I T U S. Send me your questions. I'm more than happy to help.  
Speaker 1    00:52:48    Yeah. We're going to put links in our show notes so they can find you get the emails. We'll get the LinkedIn, the whole nine yards. Hey Steve, man. It was an absolute pleasure. Hopefully you guys have some better weather up in New York, this weekend  
Speaker 2    00:53:00    Bag zap. Appreciate it. Take care.  
Speaker 0    00:53:03    Thank you for listening to the sales samurai podcast with your host, Sam Capra, be sure you subscribe to our podcast and visit sales <inaudible> dot IO and join the conversation. Access show notes and discover bonus content.