YouSaid · the spoken record

Brendon Cassidy

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45
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2024-03-08
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2024-03-08
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  1. “To the state of the state, right? So, like later stage unicorns, right, that are figuring out like, oh, crap, things have slowed. And what do we do now? Like talk desk is certainly like a company that had a really went through a tough period and they've now completely course corrected from everything that I know doing really, really well now. And that's hard to do. I think for a lot of those unicorns, that's hard, right? When you hit that, those bumps maybe chasms like how do you bounce out of that and get on a good course again? There's a lot of great pre-seat seat startups and founders out there right now, which I think is always when the market is down, you tend to see a real bouncy in that area. That's how tech mitigates these things, you know. When the risk is mitigated between like a safe, big company and a startup, then you tend to see a lot of super talented people flow into the early stage world.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  2. “Certainly rippling, I think pretty impressive what they've done. You know, the CRO used to work on was on our team at EchoSign back in the day, Map Plike has done an amazing job there, Rippling. And there's a lot of talent on that Rippling team, which is one of the advantages.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  3. “The stuff I'm working on is a passion project for me. I've just seen the go-to-market model for startups is so daunting and becoming more daunting with there's just so much noise you're competing against that the traditional ways to get in front of customers is changing and maybe change forever. The world I want to see as a world where you're starting out your sales process as close to the customer as possible as a way to sort of mitigate a lot of risk in how startups grow that's the thing I believe most in is that going to market on the backs of you know like a sort of let's just go crank out 100,000 emails and make a thousand calls I never really believed in it it was like one of those things that everyone just kind of had to like okay yeah yeah yeah yeah we'll do that sure and you have to do it as well as possible but i never believe that that was ultimately going to scale and it has not that's what's most interesting to me”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  4. “The kind of outbound SGR model is very much in Flex. I think AIs, I really do think the SDR outbound SDR function is going to fall back under marketing, which is probably where it should be. There is a quantum shift 10 years ago, and it's going back. I think it goes back, especially with AI, the onset of AI. I think that is a place AI can really help solve and fix. But that's a big deal to sort of take demand generation out of sales, which I don't think any VPs of sales really want to own that, quite frankly. At least outbound like in that sort of SDR function, that's going to fall under marketing. I think that's a pretty big quantum shift.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  5. “Salespeople that aren't dependent on an SDR team to drive their own deal flow is going to be a timeless recipe for success”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  6. “Partner in VasterCard with Salesforce and we got our asses kicked. That was one of the most rewarding deals ever I've ever done in my career because we had no business winning the deal. We had no business even trying. But we just said we're just going to do everything right from here. And, you know, if we lose, okay. But like, if we win, man, how good is that going to feel if we do win? I think that's more prescient today. The customer evaluation process is so much more layered and there's so many more stakeholders. I mean, there's even now like a sort of subvertical and SaaS of companies that are sort of creating this salesman, these products to manage all the different stakeholders, right? That was back 13 years ago. That was pretty innovative. I think now it's more the norm. You can't really not do it now.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  7. “Facebook was super high profile, right? Facebook was like the hottest company in the world. So we were really, and we had just beaten DocuSign at Facebook. We were really leaning heavily into that. And they were like, we're standard and poor. What do we care about Facebook? And I was like, well, I think their valuation is worth more than you, right? That was a judgment call and making that statement. And so DocuSign had just, that's all DocuSign did was go C suite, Salesforce's endorsement, but there was two other layers of people, right? Evaluators and users. And then we just basically Sam and I were like, yeah, at this point, it's like, it's just, that's all we just wanted to do is just beat them. And so we were checking in on every evaluator and user every day. Like literally it was like rehearsing a witness statement with them, you know, when they went to sort of provide their feedback back to the C-suite. And DocieSign had never even talked to any of them. They had just sat on their fat asses, right? And said, we played the C-suite and we played the.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  8. “He had to fly back. We show up Monday, everyone's in the room, and they're like, yeah, so, you know, we're going to pick Salesforce, or we're going to pick DocuSign. But yeah, go ahead, make a case. That's how it started. And we beat them. Because usually when a partner tells you to pick someone, it means that there's a level of due diligence you didn't really do. And so we were like, yeah, like what we would say is, you know, do the same thing that Google did and Facebook did. And we just walk through all these companies that had evaluated that we'd gone head to head against Docu. You sign that? And we said, and they did the same thing. You know, they didn't pick them because a partner because Salesforce said it. They just did a head-to-head evaluation. And this is how they evaluated it. And this is how they determined. And so do that. And if we lose that, well, great. We walk away happily, quite frankly. And if we win it, then you pick us and you kick them out of the room because that's the same decision that everyone else made. And so at that point, Facebook, this.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  9. “Sort of proof of concept or pilot. And we were going against DockySign and DocuSign was maybe at one level in the deal. One level and we were at three levels. We were pushing all levels towards each other. And the Dockie signed up loose deals to us and they didn't understand why. And we were like, yeah, well, you left your flank completely unchecked, man. There was a deal we were in at Standard& Poor's Salesforce walked DocuSide into the deal, right? Against us. Said, pick them. We went to New York. This sort of overlaps with one of your questions over the talk about a deal where you went outside the box. Sam Blonde and I went to New York, showed up at Stadard and Poor's on a Friday. No one showed up for the meeting. And we were like, Jesus, we just flew to New York. We're staying in a hotel like where this kind of bootstrap startup. I think I told Jason, yeah, like good first meeting. We're going to meet them again Monday, right? And that was what we told that. We were able to get them to meet us Monday because for whatever reason they all, none of them showed up.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  10. “And usually when you lose deals, it's what you didn't do five steps prior, right? Or what you didn't establish. There's all sorts of stuff when you try to do a post mortem on it where you can look back and you can say, here are the things we really didn't solidify these things. There were stones unturned is usually when you do when you analyze why you lost a deal. Our motto is always like, let's turn over every stone. We were so good that we could walk into deals where we were given a blindfold in the cigarette at the beginning of the sales cycle where our competitor had us beat 10 waves Sunday. They were in the deal. They had partner and vendor support. They had everything imaginable where we could, you know, we could undo it. Out of that, certainly that ECOSAN team, one of the things that we did, which was not the norm at that time. Maybe it is now. We were in every layer of the deal, right? We were at this, we were in the C-suite. We were with evaluators and decision makers, even users, right?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  11. “If it was a committed deal, I always tried to view those like they have to feel that or what's the point of committing deals. And so that was a big deal, right? And that was going to be, you know, sit down one-on-one with a salesperson, which I did every week with every salesperson, right? And that was we were going to spend time and say, hey, like, let's talk about why this deal was committed and why it fell out. And, you know, usually there was, you know, the warning signs were just blinking red. And in some cases, I should have seen it talking about like that, oh like you know, this person hasn't responded to an email or a call in a week. That's not going to close. But yeah, they would, if it was a committed deal that didn't close, I've always felt like that. They have to feel that. It doesn't have to be like, I'm not going to fire anyone for it, but yeah, it's going to be a discussion.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  12. “correlation. If you haven't emailed with a prospective customer and usually more if there's like a three-day gap and it's like a committed deal and like maybe there's a contract and legal or whatever else, you're not closing that deal, generally speaking, right? And so that was one of the things that I would always look at is like, you know, where are we at with the customer from a communication standpoint? When was the last time this customer emailed you or called you or returned your call or picked up your call? And if it hasn't happened in three days, it ain't happening, right? Something's wrong. There has to be constant communication with a customer if it deals, you know, when you talk about all the contracting legal review and all the rest, there's a very fluid processor and when there's big gaps in communication, I'm like, okay, so let's take that out of commit, right? Should we put it to closed lost?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  13. “I mean, most of my dealer reviews would start with, you know, obviously we were any communication with the customer. So email, we weren't really at a point where like all phone calls were being captured, right? But basically I was in a deal review. And again, remember for us, we were running a monthly review. We were running every month, every salesperson had, and this is how I've run it in every company I've ever been in. And it's worked 100% of the time with various types of sales cycles and types of products. But we had a, you know, everyone would have a monthly commit. Here are the deals I commit. And then here are the deals that I have in best case, which are deals that are possible but not committed for this month. And that makes it very simple. You're breaking a deal down. You're like, yeah, so here's a deal you haven't committed. You haven't talked to this customer in two weeks. How's that possible? Right. Like it makes it very simple. I always look at like customer communication, the correlation to like how possible a deal is or like it's like 100%.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  14. “All these people, you know, just lighten up the board, and they're going to be like, God damn, man, I need to do something here, you know. And most of the time it just doesn't work, to be honest. Most of the time you try to like overlay the strategic team. The failure rate is about 99%, just in reality. Because the reality is they probably can't, even though they have all this experience and all this other stuff, they probably can't sell as good as Sam Bon can, right?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  15. “They have to have some have sold within the ballpark. It doesn't have to be like, oh, well, it's $5K off in ACV or something. But yeah, they have to have sold somewhat similar price point and sales cycle like velocity-wise and all that kind of stuff. It doesn't have to be exact. You know, hiring somebody that sold super enterprise nine to 12 month sales cycles in a pretty transactional high-velocity sales org is not going to work out ever unless you're willing to like make an exception for them and say, hey, I realize you're doing bigger, longer, more strategic deals. So you really have to almost partition them out, right? Because a lot of times you'll try to hire those strategic people where you have this young dynamic transactional team. You'll hire this strategic team and they'll see these kits just crushing it. And then creates this tension. This happened many, many times. I could walk through the number of companies where it's happened. They have to be separate because they're going to see this team over here of like Sam Blonde.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  16. “What looks good on paper and what actually plays is super complex. And so most people hire a resume with names and titles and companies on that resume and they think that that stands for something. But there are a lot of other layers to that. This particular hire I'm talking about, we hired him and he was gone in a month. I walked him out the door in a month. And it turned out we had all these incredible young salespeople that were great. We brought this guy in as like, oh, this guy's better than them. And he wasn't. He wasn't even in the ballpark of how good they were. And just for us reinforced like, hey, this is an ultra-talented team. It lets in that team. Let's move those people up. Let's get their DNA across more of this organization. For me, it's all about taking the people that have proven they can do it in your company, in your system, with your customers and letting them run and then taking them as far as they can. The odds that you're”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  17. “Being enticed by the resume, right, by the experience, we hired this person at EchoSign. It was like this, kind of been there, done that hire. He had been like, he was 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 Davidson right up to the front door, like right to the front door of the office, right? And that was like a red flag. Whoa, okay. And the reality was it was he probably was amazing at one point, but he wasn't anymore. It's looking at a resume and seeing like boxes checked. Oh, wow. He was here then. He was there. And then he did this. And I think that's one of the mistakes people make in hiring salespeople as they hire. Is that who you're getting when the resume looks amazing? Are you still getting that person? Or was that person just right time, right place, lucky, et cetera, in discerning between what?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  18. “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 when fully ramp 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  19. “If you're a founder, any other founder led sales motion, they need to just be at your head at every turn. Every sales call you're on, you know, probably for like a couple weeks where there's not a lot of expectation put on them, but 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 a very easy way to like analyze and synthesize that data, have your salesperson listen to like every sales call like within reason, right? 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 going to 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  20. “I always felt like if I'm on calls with them and I feel like I have to take the call over and run it for them, that's a first step of like, can they run the call in the way that you want it done without where you can be involved and help on the margins, but you don't have to run the call? That's pretty important. A lot of the sales fires 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  21. “You generally know in 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  22. “I would say first off in the same way, like if you're expecting to hire people off the street, expect a super high turnover rate. There's a 98% chance that each hire is probably not going to work out”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  23. “That's a super fluid concept because I think the way that we've compensated salespeople like five years ago is probably like null and void now. I would say the ECOSIN model is a great model for times like this. Pay a 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 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. And then once you paid for yourself, we paid like 15% after that. I mean, it probably averages out to something more normal because we were not bootstrapped. I mean, we only raised like $5 million, I think, in the lifetime of the company. So we wanted to make salespeople 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?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  24. “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 and the talent. And so like TalkDesk 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 a VPs of sales now.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  25. “Obviously, I want to hire a network for my first three to five hires. Ideally, someone, at least one that has worked for me before, where I know that whatever the conditions 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 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. Everybody 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 Salesforce or Oracle or Adobe.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  26. “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. That's a pretty good litmus test for hire. 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 characteristics because most SDRs are not 10-year SDRs. They're early on in their career. And so you're looking for people that have the characteristics that are coachable that you can mold and develop in the way that you do it.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  27. “The sort of signature moment in a hiring process for a salesperson, we would always have them do a demo. Are they like close to game condition sales call it's possible? We used to do is we'd say a pitch us echo sign, sell us echo sign as a like prospective customer. And then I became, you know what? Look, let's just have them sell what they sell now. You know, whatever their product is today, 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 a talk desk, we had like a panel as myself and my first three sales hires and we would listen to them pitch that and we would say it has to be unanimous. All of us have to sign off on this person. And that was sort of how we would go up or down in that process. Obviously that creates a pretty high standard, but the logic was sell me what you sell today. What you sell today, if you, if that's not a compelling story, then why is it going to be compelling here?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  28. “So, if you have investors, that's one place to start. Although investors are notoriously bad hiring recommender, I'm sure I know you're different. Most investors in BCs, they make a recommendation, and my advice would 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 would 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-M partners, give them equity and maybe pay them because their recommendation probably has more credibility than your own company. Their voice has more visibility than you. And so go out and create a five person advisory team that's great. How do you do that? Well, on some level, at some point, people have to figure some of it out for themselves, right?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  29. “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. Like we were, you know, just coming out of the subprime meltdown from an economic standpoint. Things weren't great. We were definitely like, we didn't want to raise another dime of funding. We were trying to drive profit.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  30. “I would say most founders are pretty involved in 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. I 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, then it's, I think, some of those assumptions have to be revisited of what you do. Obviously, the best SaaS companies have pretty active founders in early go to market.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  31. “Yes, the principles of the playbook for sure, like the broad stroke, the outline, whatever you want to call it, right, with, but don't fill it in with permanent ink. But sure, you should have a sketch down 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. If 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 Inc. should probably be written by the VPS sales. But yeah, you should have a loosely built playbook.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  32. “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, right? It was like, you know, it was like some sort of purity test, right? And 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 seen it once in my life ever, both as an advisor, consultant, a running teams. Discovery is 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 in to understand who your customers are. So my teams have always done discovery and everything else, right? If it's a 30-minute call or a 45-minute call, we're going to 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 going to show them anything if they're going to give you their time. Like you're fucking nuts.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  33. “It's not rocket science and it's not if that's what you do if you spend all your time talking to, if you sell to VPs of sales or VPs of marketing or CFOs or whatever, you should know as much about them as they know about themselves. And you should know based on like, you know, how the beginning of the call goes, you know, okay, I know that this is the world he sees. Everything I want to talk about from this point forward, everything I'm going to show this person, everything, you know, everything's going to be about I know that this is his true pain here. Like this is his true opportunity. Every great team have been on knew that. And they had it mapped out and there was never, ever a 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 discovery I've been talking about this for years. And there's trust me, there's a ton of people that the vehemently disagree with me.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  34. “You're an expert, 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, the opportunity or problem here 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. And if you don't know them, then, you know, your VPS sales probably isn't very good.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  35. “Every company I've ever worked at or been a VP of Salesforce for the playbook was completely different than the one before or the one after. But yeah, I think it's a basic of here's our customer, here are our different customer personas, understanding the pain in psychology that exists in their world. So I've always been a big believer in 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 can't, how do you not know what the customers' problems are? You should know what their problems are and what their psychology is before you ever get on the fucking call, right? Like that's 0.0. If you need to get on a call and spend two and a half hours doing discovery.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  36. “And the question I ask is, 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 want me to solve, why they were the person to solve that problem.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  37. “That's an extraordinarily fluid discussion. And ultimately what AI does is probably get put the SDR function back under marketing ultimately when you can maybe accomplish the tasks of multiple with one. A lot of the problems we have today, you can loosely trace 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 VPF sales is ever going to take a job with a company that's dependent on an outbound go-to-market 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. They know it's probably a fade accompli at that point. That company is probably not going to make it. You know, I've probably advised 60 Sas companies the last 10 years. You talk to many, many founders.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  38. “I don't think it's a matter of getting it. It's a matter of in lieu of better alternatives. 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 so much glut in every sort of vertical, right? There's a thousand companies competing for attention from one buyer when you go back 15 years ago and that was five for 10 companies. How are you going to mass produce some sort of out quasi-personalized outbuyer 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 existential dilemma everyone's facing.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  39. “Scaled low cak 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 to, how do you leverage sort of relationships and influence around people that are close to your customer to accelerate yourself in the market via relationships, referrals, nudges, influence?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  40. “Do it that way. You talk to startups every day. Every startup is laser focused on break-even in profitability and long-term sustainability. The customer, the CAT costs of five years ago are 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. A lot of the ways that we have traditionally done sort of like marketing demand generation have long since not worked. A lot of people are in the space of, okay, what now? That's my general state of the state. And so every hire has to be like a 10x, a 10x scrapper. So what now is PLG content?”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  41. “We're there, they've all gone on to like incredible success because nothing will ever be harder than that. Brendan, how do you analyze where we're at in the sales playing field today? Got on the call and you said, you know, ah, navigating today, how do you analyze where we're at today? The way I would analyze it is anything 24 months or older, if it were in a space of clay, of putty 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, we're very much in a place where it's like the more you can unlearn, the more that you can walk away from bad habits and things that we thought were true that aren't anymore, the better off we're all going to be. Not a comfortable place to be for most. One of the biggest things we need to unlearn with sales teams, I think the like, let's spend $10 to make a dollar in 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  42. “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, 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. That's a pretty good primer to get in the sales, right, where it's like, you are constantly having to kind of reinvent yourself. You have to be able to be very adaptable to whoever you're talking to, whomever 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, you know, 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.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  43. “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-backed companies sort of around sort of helping them build their leadership and management teams. That was really my first job out of college. Came in at sort of the height of it. And then the entire market collapsed. And then recruiting became literally the first thing. That's the first, oh, recruiting fees? Yeah. That's not even, 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 fired people. No one's hiring people. What now? And so that forced all of us. We were all really young. A lot of people didn't make it. It's so fun.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  44. “Joining me today. Also, great to be here. Yeah, I think it was Blaston we saw each other. It was maybe in Napa some years ago, I think. Yeah, it's great to see you. Brandon.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source

  45. “I can tell you no great VPF sales is ever going to take a job with a company that's dependent on an outbound go-to-market model. For my first five sales hires, I would never hire somebody at a network ever. Ultimately, what AI does is probably get put the SDR function back under marketing.”

    2024-03-08 · The Twenty Minute VC · 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 · IDENTIFIED FROM THE TRANSCRIPT · source