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Never Be The Victim (Rob Desmond and Jamie Schneiderman) · Unstuck Pod

• Jamie: hi everyone and welcome, to the Unstuck Pod. today, I've got Rob here. want to pass it on to him. I'll let him give you an introduction, let you know what he's done, where he's come from, what he's doing, and then jump in from there. Welcome, Rob. Rob: Thanks, Jamie, appreciate you having me. Jamie: So if you want to just let everybody know about you, what you've done, where you've come from and what you're doing now, that would be amazing. Rob: Sure. So I, currently providing advisory work, to, know, kind of start up and ⁓ scale SAS based companies ⁓ in number of different countries at the moment. I've been in sales most of my was bitten by the startup bug early on ⁓ and, you know, found ⁓ a love ⁓ of solving kind how to bring either discretionarily funded or new market approaches to the market. And was also lucky enough to work for some really amazing leaders early in my career where at the time, in fairness, I didn't realize maybe how good I had it or maybe a bit too immature to realize how good I had it. But there's things I learned early on that I still apply today to what I do. So started my sales career about 25 years ago as an SE, ironically, because that was the only path I could get into. knew eventually I wanted to get into sales, but I studied engineering. liked solving problems, that for a short period of time, and then, you know, earned the right to ask for a sales role, which led to ⁓ having a variety of different go-to-market roles in a number of companies. Up until about two years ago, as I was exiting a business and then through a friend and colleague of mine who does investing said, Hey, you know, while you're looking, can you, can you help me with a few investments that we've made? They could use somebody that's been around the block a couple of times, which you can tell by the grays in my head that, ⁓ you know, Hey, maybe just a sounding board to the CEO and the executive team about, you know, one organization was looking to raise money. And the other was actually just received money. And in either case, you know, the board was looking to understand, are you, are you going to spend my money wisely? I've been doing the advisory work for two years now, expected it to last just a couple of months. And, but here I am with a handful of clients ⁓ I really love, I really love being able to take my experiences, both the good and bad, you know, ⁓ more so ⁓ what did I see that we didn't do right and helping others. prevent from making that same mistake. Jamie: So, no, and speaking of that experience, you you talked, you started off by saying, you know, I probably had it pretty good with some of the folks that I learned from and some of the things I learned early that I'm still applying today. What kinds of things that you got early, earlier on in your career that you were exposed to that were some like aha, this is actually really important. I mean maybe you didn't realize at the time, but I'm still doing it now. Rob: Yeah, think the biggest one for me would be how really is a process. ⁓ And not, you know, it's not me getting to know you Jamie, and then liking me and then you buying something. Really is following a series steps where you know, each side is accountable to an outcome. And then you know, as you more experience doing that you also quickly learn how to understand bringing somebody along that journey at the same token, to get to that desired outcome, but in the same token, realizing that, you know what, Jamie you're not a good fit for what we do and let's just part ways. So neither side really wastes time trying to get something done that we should. ⁓ latter statement there I think is even more prevalent now with the amount of tools that get purchased and churn and how much churn can really impact your business. A lot of what I'm seeing and what I've been lucky enough to experience is you have a pretty good process that really articulates and demonstrates value, and these are all canned terms you hear all the time, but when that's carried through the organization ⁓ your post sale team really knows how to deliver against that. how you get happy customers, which turns into references, which turns into growth and revenue, and you worry less about churn. Jamie: So again, I think you mentioned sales as a process and you have to it work. I that with the companies that you're working with or have worked with, that that process isn't the same every time. Rob: No, no. And it changes a lot too, especially if you're, you know, you're a small company that's just starting out and you've got to figure out product market fit and understand who the best targets are for what you do and the problem that you solve. And then once you figure that out, you've got to go deep and make sure that you're covering a lot of the bases. And then from there, ⁓ that's determined, you know, how do you make that repeatable? So set a different way. You might get one or two wins early. Don't run out and hire a whole sales team and a sales leader because you typically don't have enough data at this point to know how to make this repeatable and get you through those, you know, those early phases of growth. Jamie: So let's talk, cause I do want to talk about the transition from the early days, the early stuff that you do to the repeatability. So what are the signs that you're looking for when you're trying to build a repeatable process, especially around sales the things that you should do first as you start to go do that. Rob: think the first thing when you have a first couple of interested parties, you're always going to have first movers and people who want to try technology. in the organization do they sit? Is it really a business problem or is it a nice to have is ⁓ of one simple example. The things you want to look for ⁓ are same industries or are the same people, persona, Jamie: Yeah. Rob: solving that you're solving a problem for, they consistent. And one of the things I've always recommended to do is you really, you map those out. You map out your early adopters, you map out the industry they're in, the revenue, right? Who the persona, you know, first and second buyers were, who was against you doing something within that organization and develop some early repeatability. So you're not chasing things that You you may close, but it may take way longer than it should. So, you know, you we've all heard the phrase kind of stay in your lane, not not a fan of it, but it's relevant to stay within a confined area to make sure that the product that you have is ready for the market you're trying to sell against. Jamie: Yeah, I always talk in terms of ⁓ the alignment between the problem, the customer and the solution. So exactly like you're saying, and if you're doing that and you're staying in your lane, if you're, if you're staying focused, it's a lot easier to build a form of repeatability makes sense to me as you're describing that from a sales perspective. Rob: Sure. And you know, if you're selling to the CIO of a big financial services company, they're going to have, you know, friends and colleagues and other businesses. And it just, those early conversations become much easier than, than trying to do it into, you know, 10, 12 different vertical sub industries at one time, regardless if that problem is actually transferable across it. don't an early adopter from Jamie: Mm-hmm. Rob: financial services company isn't going to quite care as much if you have a manufacturing company as an early adopter. Getting that transition, getting that comfort level to buy is going to be a little more difficult. Jamie: So let's talk a little bit about, talked about what you should do. Let's talk about you know, what you shouldn't or what you've seen that hasn't worked, that companies have tried. You know, you're in there trying to clean it up or help advise them out of that. Give some examples you can. Rob: Sure. I think there's a couple of easy ones. One is hiring too soon. So you're a really small company and you're trying to get out and sell and let's just say that you're a founder or know, an early stage executive, you need to be in front of customers. You need to hear firsthand that the pain you're solving really matters and it ⁓ really ⁓ moving needle on their business in some capacity. So that's because you need to be close to the customer. And wins don't necessarily translate to hiring a team. I think one of the bigger mistakes that I've made myself and that I've seen in the past is you have a couple of early wins. Maybe you raise little bit of money and then you set, you set unrealistic revenue targets based on something that isn't repeatable. So really, ⁓ nailing that down and being lean in the beginning, documenting why you're winning document more importantly, why you're losing. Right. Double down on one, avoid the other. think those, those are big. then, you know, specifically from a sales marketing, customer facing role, the, the persona of that individual that you're bringing in and the characteristics of that individual is really important because the skillset required at that stage of a business is very different than the skillset required at a later stage. And. I think a common thing that in events like, know, episodes like this or other things you read is bringing somebody in who's got 20 years of complex sales experience into a startup. There are people that can do it. Don't get me wrong, but it's a, it's a very difficult transition because in an early stage, you're, you're doing your lead gen, you're, developing content. You're doing a lot of lifting on your own. Whereas later you have a lot of resources around you. Jamie: Mm-hmm. Rob: So the third piece I'd say that's really important is make sure that you have type of candidate that you want and know that the business needs at a given stage rather just hiring somebody because they will to you. Jamie: No, and I, so let's talk about that. Cause I think, you know, one of the difficulties of early stage and again, early stage it's runs for a while, but is that you don't have a lot of past experience to go, need another, I need another Rob or I need, you know, like that kind of thing. It's, you're hiring often for a role for the first time. You're not sure exactly what you need. How do you think about know you mentioned somebody who's got who's flexible, who can handle ⁓ range of different tasks they're going to have to do from a sales perspective. Certainly. What would be looking for? How might that vary? You know, what's the most what are the most important things? Rob: So think there's a couple of things. I'm a really big fan of like people, like a skill and profile quadrant that you put together for candidates. ⁓ know, if you're selling into financial services, somebody who's sold into that, a like solution ⁓ necessarily matter, but someone who understands the persona you're going after and the industry you're going after, the type of competition or pain that you have. you know, that's kind of one bucket. And then another bucket would be what's the skills, right? Is this a PLG led sales motion, or is this more a true enterprise sales? So the skill sets for those are going to be different. So have they been trained in a formal sales process that's applicable to your business, right? What type of sales methodologies have they? have they been taught and know well? And then another bucket we look at would be kind of, you know, who are they? What are their intrinsic characteristics? You know, what's their drive? What's their curiosity? What's their grit? We've all read the book, but the grit aspect of an early stage is really important because it's not a nine to five job and it's not a nine to five, five day a week job, right? It really does require you to put in a lot of effort to pay off. And then the last... The last piece is the easy one from a sales perspective is the execution, right? How well have they done? Have they done it in a similar type of, of size or scale business that's, you know, breaking in? it a net new market approach or is it a competitive takeout approach? just understanding now, are you ever going to find the perfect candidate? No. But when you break it down and have a formal hiring process, you get to understand what the gaps are of that individual and then help them. overcome those gaps by the second piece would be in some sort of onboarding, like handing them, here's what we do, go figure it out. There is a bit of that, but you do need to spend time educating them on what it is that you do and why people are going to care about. Jamie: So yeah, and so in terms of the, I, cause I was thinking that as you were talking about the onboarding piece, if I'm a CEO, I'm bringing on this person, obviously I know I need it. One of the reasons I may need it is because maybe I'm not good at it. So it a matter of giving them the tools or is it a matter of spending time with them? How you see that playing out in most cases? Rob: The chances of them having the tools is, really minimal. It's spending time. It's educating them. Now, ⁓ it were like your first sales hire, you want that curiosity and that drive, right. And that problem solving component to be really high because they're going to go figure stuff out for you because to your point, they haven't done that before. So ⁓ clear on what it is. And then be prepared that that person is going to come back and say, yeah, know, I know we're trying to sell this, but actually it's a better fit this way. And here's why. Like that's a candidate that they come in that that is a perfect candidate in that example. And in a lot of the smaller companies that I work with, you know, the folks that are out talking to prospects, you have to bring that back and you have to have a culture that's willing to be open to, ⁓ pivot because ⁓ chances of what you brought to market in V1, it's gonna be different in V1.2 as an example, right? So it is gonna pivot and just figuring that out. Jamie: So, this is your first, you if this is a senior level sales lead and it's, you know, the beginning of that, how much you balance their ability to go and figure it out and do it themselves versus their ability to lead or create, build a team in behind them after? Rob: Great question. So ideally you'd have somebody that could do both, but early stage, my recommendation, and thankfully what was kind of ingrained in this is you, you absolutely want that person to go out and do it themselves to be on the front line. If you hire your first salesperson, whose only expectation is to come in and build the team, then that grit and resilience I talked about earlier, probably a misalignment because they need, in order for them at that stage to be really effective and build the first team on the ground, they need to be the go-to resource on problem solving and getting through and being able to close transactions for the business. Jamie: So how hard, I wanted, I'm curious to know like if a company's been doing selling and most of time it's the CEO or it's the leaders that you've been selling a certain way to bring in a person who's gonna start institutionalizing that and even if they're the first person who's gonna do that, how hard is the transition? How much does that impact? How much does the structure, the culture of the organization impact? how that will work and whether that will work, I guess, is the important piece here. Rob: So I, I, was lucky enough to work for somebody early on in my career who had a phrase called everybody sells. And on in, in the stage ⁓ of, the life of a company, everybody does to sell CEO founder, you know, regardless of role to understand exactly how the market is responding to what they do. So your specific question around the transition from, say a founder to, you know, your first head of sales, you can't trust that individual right out of the gate, then you likely made a hiring mistake. So that's first, And, you I would recommend you go to your network and if you don't have, if you've never hired a salesperson before, there has to be someone in your expanded network who has. and bring that individual into the fold and help them help you hire the right person. Right. So that's one. second would be when do hand it over, understand that as a founder, you're way more valuable a little bit later in the sales process than in the very beginning. ⁓ And good sellers know how to uncover pain. They know what a process looks like. And then bringing the appropriate resource at the right time ⁓ is, key. So you're going to sell early and often as an early stage founder. And if you're both the founder and CEO, and you started the company, you started it for a reason. You started it because there's a pain that you strongly believe that your business can solve that, that in infectious, which is great, but make sure that you trust the person that you're, that you're brought onto the team to be able to get you to the point that can help you close that transaction. If that makes sense. Jamie: No, makes total sense. think that's a really important... And what about the person coming in and working with the rest of the organization? I imagine that that is a... You talk about a process and the new person's got to create a process, but it's going to impact and connect everybody else too. Rob: So, and I'm pausing cause I'm recalling a very specific example in my career where I, you know, I came into an organization and just had the wrong personal outlook on what should and shouldn't be done. And it was more mine and I didn't really take the time to, to get to know the rest of the organization, specifically the, like the founders and the executives to get their vision and make sure that what I believe based on my experience, is aligned with what they're trying to do. Because may think that, we're better served here, but there's things that I don't understand about the market perhaps yet that they know that I don't. So that alignment is really important. And other that we've all heard about, but just how do I want to be communicated to and how do they want to be communicated with? Jamie: Mm-hmm. Rob: is an important dynamic of an early stage, like say founder, head of sales or sales leader responsibility what, know, on your way in, if I'm, if I'm that first salesperson, what are my goals? ⁓ How you, how did you calculate them? Are they achievable? Right. Make, ⁓ don't someone to come in with a really elevated quota. As an example, that's not achievable because you set this based on one deal that you did. Jamie: Mm-hmm. Rob: Right. And I have, unfortunately, I have seen that I've seen companies do, you know, two deals early, then they go hire four to six salespeople. And there's no way you can onboard all of those individuals at one time, let alone hire all of the right people you need. If you're hiring four people at that size of a business without having dedicated resources to do that. Jamie: Yeah. And you think that they do that just because it's like, okay, now we just got to grow. Like, let's go take it and duplicate it. Rob: Sure. Yeah, there's always, there's always, know, whether it's investor pressure, personal pressure, whatever it is, you know, I've seen it both sides and, ⁓ and, you sometimes it's really important to slow down, to speed up and slowing at those early stages and really documenting where we're good, where we're not. I lean heavily on the where we're not because time has money in these, in the stages of these businesses. So you wanna really avoid spending time in places that it's more difficult for you to sell. Jamie: That's great. say that to people all the time, go slow to go fast. And so I agree with you completely. I ⁓ it's often overlooked because there's, like you said, pressure to go fast. Everything fast, ⁓ right? Rob: Yeah. Yep. And there's nothing wrong with that. And the other piece of this back to like how important the relationships are at that early stage, that's inclusive of the board. So if the board is presenting a big number, dig in. And as an early stage individual, my view is you should have access to the board. You should have open conversations with them. And, you know, boards typically aren't going to help you sell. can help me maybe make introductions, but, you know, if they've invested in a number of companies, there has to be a network of people that you could tap into as that first seller. That could be helpful, but understanding their expectations and making sure they're aligned with what you're seeing is important, which goes back to the communication piece. Jamie: That's awesome. Any advice that you want to pass on to the audience. Anything that you want to have them leave with? Rob: Uh, Well there's so many. so many, I mean, I love sales. I really do. I like the problem solving aspect of it. Um, you know, The grass isn't always greener though. It's just a different shade of green, leaving one company and going to the next. I'd say if I had a parting, kind of a parting thought, um, and this resonated with me more you know, later in my career is you do really have the ability to, to move the needle as an individual and you carry yourself internally and your outlook and ability work together really important. It's we don't have these things, I can't be successful. ⁓ I worked for a CEO had a phrase that he always said, don't be victim. And it's really easy to play the card. right? I don't have enough leads, therefore I don't have enough pipeline or you know, that guy lied to me and I didn't get my deal done or whatever that is. And and if you go into it with, Hey, I'm not going to have a victim mentality and I'm going to get everybody on board to help me. Cause that's also important. You're a lot of, A lot of sales executives have an ego, which is great, which is they're in sales for a reason. They believe in themselves and the rest but it is a team sport in many aspects. So getting everybody together, win together, lose together, figure it out together, and don't be a victim. Jamie: That was awesome. So Rob, how can people find you, follow you? Rob: I don't have a huge, probably ⁓ on but I don't post a bunch. you know, ⁓ you can, can find me on LinkedIn. ⁓ I, you the consulting work that I do now, I really, I really do love bringing back, again, more of the mistakes that were made rather. ⁓ I was fortunate enough see companies grow and have them get acquired and all the rest, but I really do lean heavily on the things that we missed ⁓ and applying those is that I really. I really enjoy, uh, as you can kind of see by the hockey shirt here, you know, hockey has been a big part of my life. I know you live in Canada. We'll, we'll avoid the gold medal game comment right now. Sorry. I had to throw that in there, but, uh, you know, for me, um, when I, when I talk about, well, we can scratch that out. Like where to, where to find me? Uh, I completely just lost my train of thought. Jamie: That's okay. I don't know. That's okay. But you said on LinkedIn and that's fine. And I think, Rob: what I was going to say is like, you can find me on LinkedIn. you know, I work with a couple of different investors now ⁓ and I my network to align resources companies if particular marketing feedback or you're building a PDR team or you need CS help. so LinkedIn is ⁓ the best way find me at the moment. And, ⁓ you know, look forward to, I look forward to speaking to anybody who has a question. Jamie: Okay, thank you. No, great. And I'll make sure that we add links into the description so people can find you. ⁓ Listen, Rob, thanks so much for joining. Appreciate it. And to everybody who's watching, thanks for watching and listening and we'll see you the next time. Thanks. Rob: Perfect. Appreciate it, Jamie.