20Sales: Outbound Sales is Dead Today, Why Demand Generation Will Move Back Under Marketing, "Wisdom" that Everyone Needs to Unlearn About Sales & Why You Should Never Hire Someone You Do Not Know in Your First Five Hires with Brendon Cassidy

0:00I can tell you no great VP of sales is ever going to take a job with a company that's dependent on an outbound good and work a model. From my first 5 sales hires I would never hire somebody out of network. Ever. Ultimately what AI does is probably get put the SDR function back under marketing. This is 20 sales with me Harry Stabbings now 20 sales is a show that takes you behind the scenes with the best sales leaders in the world to reveal their tips, tactics and strategies when it comes to scaling sales teams. Today, I'm so thrilled to be joined by Brandon Cassidy. Brandon is the former first head of sales at LinkedIn, and former VP of sales at TalkDesk.

0:34Now before, Brandon's also spent time advising some of the best, including Gong, pipe drive and showpad to name a few. But before we dive in, can you think of one video you watch today? Of course you can, because in 2024, video is everywhere, and it's time for you to start making more video content. You can go the traditional way, but it's time consuming and expensive, or you can start creating them from a browser using this AI tool called Synthesia. It was just named the fastest growing software on G2. I tested it out recently and making videos there is easier than making a slide deck. Literally, create fresh content or replace dull text, power points and PDFs with engaging professional looking videos your audience will love.

1:17Craft your script with AI in 120 plus languages. you can choose from 140 lifelike customizable AI avatars to actors presenters, or have your own custom avatar created. I'm getting my AI clone next week and I'm super excited about it. 50 % of the Fortune 100 companies are already on board, reporting up to 90 % time and cost savings, visit synthesia .io slash 20vc and create your first AI video for free. And speak of game changing products like synthesia there. Have you ever wondered why spending company money is so broken. Employees want to follow the process, but they're confused and frustrated.

1:56It takes forever to get anything approved, and folks in procurement, finance, and other stakeholders are just as frustrated too. Duplicate spend, unauthorized contracts, surprise vendors, late invoices, missing receipts and documentation. It just doesn't end. It shouldn't be this hard. It doesn't have to be. ARBASE makes it easy. ARBASE is the only procure the pay software that beautifully combines enterprise with employee friendly ease of use. It orchestrates upstream intake requests all the way through to the downstream processing of invoices, expense reports, credit card transactions and reconcile that seamlessly in your ERP.

2:32Replace a complex maze of tools, forms, emails and spreadsheets with an interconnected collaborative platform. Stop uncontrolled spend. Make it easy for employees to follow the process, put stakeholders in the loop, to learn More Head Over to airbase .com slash 20vc airbase, procure, pay, close. And finally, CFOs and controllers is expense management a painful chore sounds like you use concur. It's time to switch to Brex. Brex automates and accelerates spend management with easy to use corporate cards, travel, expense management and bill pay, all on one AI powered platform. Brex makes it easy to boost efficiency and compliance and price wide and free up your managers, employees and accounting team for higher impact work.

3:17Don't let concur slow you down. Top companies from start -ups to enterprises are using Brex to manage spend with greater efficiency, accuracy and speed. We're talking DoorDash, Robinhood, AirTable and countless other industry leaders. Ready to join them? Switch to AI -Hyphen -powered Span Management at Brex .com. You have now arrived at your destination. Brandon, I am so excited for this. I wanted to make it happen for a while. It's been a while since we last chanted So thank you so much for joining me today. Yeah, also great to be here. Yeah, I think it was Boston, we saw each other was maybe a napalm like some years ago.

3:52I think yeah, it's great to see it Brandon, I was young by them, but I want to start with a little on you just to contest you still you still look Yeah, trust me. I look like frickin' Benjamin Button, but tell me how did you first make your way into the world of sales And when did you realize you loved sales? I was sort of coming into the tech world around like 1999 2000 was the beginning of my career which is hard to believe I've actually been around that long I started my career as a recruiter So this is before the dot com bubble burst which there's not a lot of people that have that as a reference point today I was a recruiter we worked with venture back companies sort of around sort of helping them build their leadership in management teams I was really my first job at a college came in and sort of the height of it and then the entire market collapsed and then and recruiting became literally the first thing that's the first, oh, recruiting fees?

4:41Yeah, that's not it. There's not, that's a five second discussion. That became like an incredible career experience because it was like, survive. Okay, how do we survive doing this? No one needs it. Certainly nobody wants to pay for it. Everyone's firing people, no one's hiring people. What now? And so that forced all of us. We're all really young. A lot of people didn't make it. It's so foundational in my career. I can't imagine not having gone through it. What did you take away from it? That really shit hard time. How did it impact your mindset? We weren't really that experienced, so we had to, I mean, at this might sound bad, we had to basically invent versions of ourselves that weren't real, and we had to convince people that those were real, that we had a level of experience and knowledge and expertise that we didn't really have, but we had to convince everyone that we did have.

5:28That's a pretty good primer to get in the sales, right? where it's like you are constantly having to reinvent yourself, you have to be able to be very adaptable to whoever you're talking to, to whoever the customer is. And that's something that we had no choice but to learn to be that. It was be that or be gone. And so we were these 24, 25 year old kids convincing people with 20, 25 years of experience that we had. We knew things that were uncommon, pretty great experience. And every single one of the people that were there, They've all gone on to like incredible success because nothing will ever be harder than that.

6:03Brendan, how do you analyze where we're at in the sales playing field today? We got on the call and you said, you know, oh, navigating today. How do you analyze where we're at today? The way I would analyze it is anything 24 months or older, that we're in a space of play of putty, and in basically most of what we knew is off the books, has no relevance anymore to how we go to market to how we build sales teams. SDR teams, everything is more very much in a place where it's like the more you can own learn, the more that you can walk away from bad habits and things that we thought were true that are it anymore, the better off we're all gonna be.

6:43I'm not a comfortable place to be for most. What are the biggest things we need to unlearn with sales teams? I think that like let's spend $10 to make a dollar and how we go to market and how we build go -to -market and sales organizations is over. Maybe that will be a thing again someday. It's no way to run a business anymore. You can't do it that way. You talk to startups every day. Every startup is is laser focused on break even and profitability in long -term sustainability. The customer, the cat costs of five years ago are not not even considerable. The entire outbound go -to -market SDR model has collapsed in the last five years, three years, and it doesn't work anymore.

7:22A lot of the ways that we have traditionally done sort of like marketing demand generation have evolved since not worked. A lot of people are in the space of okay, what now? That's my general state of the state. You can so every hire has to be like a TEDx, a TEDx scrapper. So what now is PLG content scaled low -calc the only way forward? That's probably a podcast series. You know what I'm working on is around like you know sort of how do you leverage sort of relationships and influence around people that are close to your customer to accelerate yourself in the market via like relationships referrals, nudges, influence.

7:59You know, my conviction is that the whole like outbound sort of SDR models is over. Do you think the world gets that because there's still many outbound SDR models and teams are still operating in that way? I don't think it's a matter of getting it. It's a matter of it all the better alternatives what what else would you do? I think most people know this probably isn't going to work, it's expensive. Everyone's probably going to fail generally, but what else do we do? The uber difference between now and 10 years ago in SaaS is that there's just, there's so much glut in every sort of vertical, right?

8:33There's a thousand companies competing for attention from one buyer when he and I you have act 15 years ago and that was five for 10 companies. How are you going to like mass produce some sort of out quasi personalized outbound to go to market model that's going to engage people that are going to engage by a thousand other companies the exact same way. That's the as as extension dilemma everyone's facing. Does that not only worsen when you think about AI's impact on outbound? That's an extraordinarily fluid discussion in it. Ultimately what AI does is probably get put the SDR function back under marketing.

9:06Ultimately when you can maybe accomplish the tasks of multiple with one, a lot of the problems we have today, you can loosely trades back to like the total shift from demand gen being in the hands of marketing and into sales from marketing, which has been a 10 plus year shift. I can tell you no great VP of sales is ever going to take a job with a company that's dependent on an outbound good and work a model to grow. That's just nope, bye bye. And they may be more circumspect with a founder and telling them why they're not coming, but behind the scenes with other sales leaders, they're going to be like Not even close.

9:42They know it's probably a Fadey Company at that point. That company's probably not gonna make it You know, I've probably advised 60 SaaS companies the last 10 years you talked to many many founders and the question I ask is like why did you start this company? What was the problem that you wanted to solve and a lot of people can't answer They can't answer the question and to me it's like I can't even fathom anybody actually starting a software company and not knowing what problem they wanted to solve. Why they were the person to solve that problem. So. We always hear the term sales playbook. I'd just love to hear how do you define what a sales playbook is today, Brandon?

10:18Every company I've ever worked at or been a VP of sales for, that playbook was completely different than the one before or the one after. But yeah, I think it's a basic, here's our customer, here are our different customer personas understanding the pain and psychology that exists in their world. So I've always been a big believer and sales playbooks need to be very very rooted in what is the customer thinking not what is the customer thinking on behalf of a company but what are they thinking what is their personal opportunity and fear and upside and I've always focused sales cycles on selling to a person not to a company and that's why you know these companies that are like spend hours and hours doing discovery calls especially in this day and age it's like I care how do you not know what the customer's problems are you should know what their problems are and what their psychology is before you ever get on the fucking call, right?

11:07Like that's 0 .0. If you need to get on a call and spend two and a half hours doing discovery on your own behalf, you're not on my sales team. I didn't understand how are you supposed to know what every customer's so different? It's because you're an expert, right? These are people that you're talking to every day. Their problems and their pain is not infinite. Usually there's like maybe there's three different paths. Like, okay, what the opportunity or problem here is is one of three paths or four paths and you better know exactly what those look like and what every turnoff is on those paths before you ever get on a call with the customer.

11:44And if you don't know them, then your VP of sales probably isn't very good. I love it. We're coming out with hot taste today. I understand what you're saying in terms of the persona. It's not rock and science and like it's not if that's what you do. If you spend all your time talking to if you sell the VP of sales or VP of marketing or CFOs or whatever, you should know as much about them as they know about themselves. And you should know based on how the beginning of the call goes, you know, okay, I know that this is the world he sees. Everything I'm going to talk about from this boy forward, everything I'm going to show this person, everything, you know, everything's going to be about, I know that this is true pain here, like this is a true opportunity.

12:27Every great team have been on, knew that. And they had it mapped out, and there was never, ever scenario where you got on a call and you're like, oh my god, I never thought about that. That that could be a problem, right? Like, what are we fucking doing, man? And that's where, like, discovery I've been talking about this for years and there's trust me. There's a ton of people that vehemently disagree with me. I've advised for companies and that's all they did was discovery. Hours upon hours of discovery. Literally where I listened to the calls and they were like, they would not let that customer get into a sales cycle rate, it was like, you know, it was like some sort of purity test, right?

13:03And like to me, discovery is a means to an end. Discovery is, you know, like if you're expecting to close deals in discovery, never seeing it once in my life, ever, both as an advisor, consultant, running teams, discoveries, five minutes. That's what discovery should be. And if you need more than five minutes to do discovery, then you really, you're not putting the work into understanding who your customers are. Might so my teams have always done discovery and everything else, right? if it's a 30 -minute call or 45 -minute call, we're gonna map it out, lay it out, and play it out, especially now, where you're competing with a thousand other companies for attention, for a buyer, and you're not actually gonna show them anything?

13:41If they're gonna give you their time, like, you're fucking nuts. Trust me, there's plenty of people that completely disagree with my take there, so God bless them, Mirou. You should have found us be the one to do the playbook, to create the first playbook or can you hire it to add it? Yes, the principles of the playbook for sure, like the broad stroke, the outline, whatever you want to call it, right? But don't fill it in with permanent ink. But sure, you should have a sketched out and say, hey, here are the things that's worked, here are the plays that work. This is how we do it. This is how we run it.

14:11If you're going to be in as the first salesperson, you'll probably have seen it. You'll have seen them in action multiple times. Ultimately, the playbook in ink should probably be written by the VP of sales. But yeah, you should have an unaloocely built playbook. I'm a hypothetical founder in this situation and you're advising me. Should I hire a VP of sales first? Or should I hire sales reps first? I would say most founders are pretty involved in it, early sales. I would say if they're not, it's probably not good. So let's just assume that's the scenario. Yeah, you should not hire VP of sales as your first sales hire.

14:46I think if you're a founder that doesn't know what they're doing from a sales standpoint at all and they can't maybe they either don't want to engage or they don't know how, that it's I think some of those assumptions have to be revisited of what you do. Obviously the best sales companies have pretty active founders in the early gun market. Do you agree with Jason and hiring two sales reps at a time? Generally, but again, it's a case by case basis. Certainly, Echo Sign did that back in the day, you know, back in the day, which I would say the climate Echo Sign was in. Much more like today than five years ago.

15:18Like we were, you know, just coming out of the subprime meltdown from an economic standpoint. Things were great. Um, we were definitely like, Aida, we didn't want to raise another dime of funding. You know, we were trying to drive profitability through growth, efficient growth. Ideally, I mean, one of the advantages of hiring two is you can hire two different types of people. Because you don't know exactly like what kind of... And there's all sorts of sub contacts to that that I think change the equation a little bit like are you hiring people you know you know like I believe personally from my first five sales hires I would never hire somebody out of network ever somebody that I know and someone that's worked for me or somebody that's vouched for by somebody I trust because those are foundational hires you really can't afford to get those wrong and you can't afford to compete against any other company that's subscribing to Zipper Cruder or whatever you know wherever else you found this person and the odds of you like being able to you know I mean sales people are notorious liars I've never seen a sales resume that was 100 % honest and so it's really really hard to assess salespeople cult really really hard we could talk about oh like that's practices and processes it's just a shot in the shit there are things to de -risk it but basically if your first sales hires are just off the street it's a bat sign because the odds are it's tough to do it's tough to write and I need a 95 and 100 will die.

16:39If that's the case, then you should assume 95 out of 100 salespeople can't do it. And so to assume that you're just going to find them on the street or in Zip Recruiter or Curr Builder or wherever else they came is, you know, the odds are going down fast there. And so for me, my first five sales tires always going to come through. People vouch for my people I know and people that I trust where there's some skin in the game. So what do you do if you don't have a network? What if you do if you don't know the five? So if you have investors that's one place to start although investors are you notoriously bad hiring Recommenders, I'm sure I know you're different Most investors in BC's they make a recommendation and my advice should be like just like it's great that you are on the board of a company 15 years ago and they were great then and stuff But like so I'd say if you don't have investors that can recommend good people and you don't have your own network I would get advisors or influencers in your space that have in -make -em partners it'll give me equity and maybe paying because their their recommendation probably has more credibility than your own company.

17:40Their voice has more visibility than you. And so go out and create a five -person advisory team that's that's great. How do you do that? Well, it's on some level at some point people have to figure some of it out for themselves for it. So that's it. We enter this hiring process. Even if we do have the network, we still need to go through a process. If you were to stretch of the process for hiring raps. How do you structure that hiring process? The sort of signature moment in a hiring process for a salesperson, we would always have them do a demo. Rather, like close to game condition sales call, it's possible.

18:14What we used to do is we'd say a pitch of psychoside, cellosecoside, as a perspective customer. And then I became, you know what, let's just have them sell what they sell now. You know, whatever their product is today have run this mock pitch based on what they currently sell or have most recently sold. And basically that was the ultimately for any candidates. That was the determining factor. And like so it talked us, we had like a panel as myself and look my first three sales hires and we would listen to them pitch that and we would say it has to be an animus. All of us have to sign off on this person.

18:47And that was sort of how we would go up or down in that process. Obviously that creates a pretty hatched standard. But the logic was, tell me what you sell today. If what you sell today, if you, if that's not a compelling story, then why is it going to be compelling here? And so we would have people that we were like, yeah, we really like this person going through the interview process and they would do their pitch and be like, yeah, that's no way. They can't animate what they sell. Certainly we could probably help them on the margins, but the bottom line is it's not compelling in any way. They've been there for however many years and that's the best they can do.

19:18That's a pretty good litmus test for a higher. I would never hire a salesperson without doing that. For like SDRs, there's obviously there's a whole other set of stuff for an SDR But hiring SDRs is usually about hiring a set of like characteristics Because they're most SDRs are not 10 year SDRs. They're early on in their career And so you're looking for people you know people to have the characteristics that are coachable that you can mold and develop in the way that you do it Do you ever hire people you haven't been raps before where you can coach them and they have the aptitude and skills but they haven't been raps before.

19:50Obviously I would hire a network from my first three to five hires. Ideally, someone at least one that has worked for me before, where I know that whatever the conditions are on the ground, like they've seen it before, they can live in that world. Like once you get beyond that, then I'm mostly focused on like aptitude and talent. You're trying to find talent and coachability and ambition and work ethic. Versus like, oh, this guy was a sales force for 10 years. I won't ever hire that person in a startup generally. No comparable motion, right, versus I'm selling for a fortune 1000 tech company. Everyone knows who we are.

20:23Everybody has budget versus you get on a call and there's no acknowledgement that there's even a problem. The problem that you want to solve, there's no agreement or even understanding that that problem exists. Can you live in that world where you have to convince them it's a legitimate problem. There's no comps there for like sales for sure Oracle or Adobe or whatever, right? You don't ever have to make that kind of case there ever. I'm looking for people that want to sign up for that fight that have the characteristics in the talent. And so like talk desks after like our first three or four hires, we were hiring young up and coming smart, ambitious, coachable and every single one of them are VP's sales now.

21:03How do you incentivize them financially and all sales wraps coin operations? That's a super fluid concept because I think the way that we've compensated sales people, like five years ago is probably like no one void now. I would say the EchoSide model is a great model for times like this. Pave really high percentage after they paid for themselves essentially. And so every sales rep, that's how we did it. Every sales rep had a like full full operational cost. This is their salary and benefits and this is what it costs. And so if you closed a hundred thousand dollar deal and your cost was 15k a month, We just took 15k off, so you paid for yourself.

21:42And then once you paid for yourself, we paid like 15 % after that. I mean, it probably averages out something more normal because we were not bootstrapped, but we really raised like $5 million that they can the lifetime of the company. So we wanted to make sales people profitable as fast as possible. And one of the best ways to make them profitable was to make sure that everyone paid for themselves, right? They're none of them were cost center. I would say that's probably a pretty good model for the time we're in now. What are the biggest mistakes that found as mate when hiring wraps? I would say it's first off in the same way like if you're expecting to hire people off the street Expective super high turnover rate.

22:17There's a 98 % chance that each hire is probably not gonna work out How quickly do you know that it's not working out? You generally know it a quarter You know in a quarter you might give them more time I've had people that came in and just were gangbusters right away And then I've had people that took a little longer but I knew they were good What are the signs that it's not working out? I always felt like if I'm on calls with them and I feel like I have to take the call over, and I'm going to write it for them. That's my first step as like, can they run the call in the way that you would have done without where you can be involved and help on the margins, but you don't have to run the call?

22:51That's pretty important. A lot of the sales tires I've had that didn't work out. I'm like, I have to jump in here because it's going sideways a lot and I have to take over and fix it. they don't seem to be getting better at it. And then, you know, like obviously, like I believe in running like really, like sort of a monthly process. No matter, really quite frankly, no matter what your ASP is, that's just what I believe in the startup is the right thing to do. It makes it really hard for them to push deals out and say, oh yeah, yeah, I got, that's a verbal commit for three months, you know? That's not a verbal commit.

23:21That's a best case deal. And that's the timeframe. It's a best case deal in Bel like, you run a tight sales process without too many stages where deals can hide in. on boarding, you kind of need to give them time and you need training. If I'm a founder, what's the right way to on board new sales wraps to ensure that I'm not jumping? We can't expect them to hit the ground running from day one. How do we on board wraps the right way? If you're a founder in the other founder led sales motion, you know, they need to just be at your head and every turn, every sales call you're on, you know, probably for a couple weeks where there's not a lot of expectation but on them.

23:57But like in a startup osmosis is the best way to learn. Obviously you're using GONG or something like that, right? So you should have a Bank of call recordings and demos and you know very easy way to like analyze and synthesize that data Have your sales person listen to like every sales call like within reason rate or That would be relevant to the type of sales cycles. They'll be running I mean, obviously like right now sales training is not something that people are gonna spend a lot of money on I think generally so yeah, I would say osmosis don't have them, you know, without it, they're almost certain to fail, certainly.

24:31Do you agree with Faya fast when it comes to rap? If that's your philosophy and everyone's getting fired fast or first or whatever, then there's probably something wrong that's maybe not all them. And so if you believe in the higher you made, I don't think there needs to be a like artificial timeline on it, but like a quarter plus some change, you should start to see things going by the end of the second quarter you when fully wrapped salesperson. And if you don't see that, if you finish their first quarter and they fall short and you're in the second quarter and you don't see them tracking towards that, then maybe you let them go, but like you're probably a big part of the reason why you let them go.

25:08When you review your mistakes hiring, what are the biggest mistakes you've made hiring sales reps? Being enticed by the resume, right? By the experience, we hired this person at EchoSign. It was like this could have been there, done that higher. He had been like, he was like, like WebEx, he was a docky sign. He was, you know, he was at Salesforce. Like, wow, this guy's amazing. And like, you know, we hired him and then turned out that he was, you know, the first day he drove his Harley -Dives and right up to the front door, like right to the front door of the office, right? And that was like a red flag.