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. From my first five 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 20Sales with me, Harry Stebbings. Now 20Sales 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 Brendon Cassidy.
The former first had of sales at LinkedIn and former VP of Sales at TalkDesk. Now before, Brendon's also spent time advising some of the best, including Gong, Piped 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.
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Brandon, I am so excited for this. I wanted to make a happen for a while. It's been a while since we last chanted. So thank you so much for joining me today. Also great to be here. Yeah, I think it was Boston, we saw each other as maybe a napah. Like some years ago, I think. Yeah, it's great to see it. Brandon, I was young back then, but I want to start with a little on you just to contest.
You still you still look yet. 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 and 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 recruiting became literally the first thing that's the first, oh, recruiting fees. Yeah, 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 fired 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. That's a pretty good primary 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, who member 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. Brendan, 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 aren't anymore, the better off we're all going to be 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 in profitability in long term sustainability. The customer that cat costs of five years ago or 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. A lot of the ways that we have traditionally done sort of like marketing, demand generation have evolved since not work.
A lot of people are in the space of okay, without that's my general state of the state. 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 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 like relationships for referrals,
nudges, influence. You know my conviction is that the whole like outbound sort of SDR models is over. Do you think the world got stopped 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 better alternative. So 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? There's a thousand companies competing for attention from one buyer when he and a U of Ack 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 work at 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 AIs impact on outbound? That's an extraordinarily fluid discussion and ultimately what AI does 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, and 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 go to work at 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 a company at that point. That company is probably not going to make it. You know, I've probably advised 60 SaaS companies the last 10 years. You talk 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 just love to hear how do you define what a sales playbook is today, Brandon?
Every 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 of here's our customer. Here are different customer personas. Understanding the pain and 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 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? Like 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 is so different 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, this, the, 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 turn off is on those paths before you ever get on a call to the customer. And if you don't know them, then you know, your VP 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's of sales or VP's of marketing or CFO's 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 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 this is this is true pain here. Like, this is a true opportunity. Every great team have been on knew that and they 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? Like, 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 her 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, 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 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. Trust me, there's plenty of people that completely disagree with my take there. So God bless them, Mirou.
Should the founders be the one to do the playbook to create the first playbook? Or can you hire it to add it? Yes, then 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 sketch down. Say, hey, here are the things that's worked here, 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 ink should probably be written by the VPSLs. 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 VPSLs first or should I hire a sales reps first? 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 VPSLs 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 sales companies have pretty active founders in the early-go-to-market.
Do you agree with Jason and Haring to use 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. Like we were just coming out of the subprime meltdown from an economic standpoint. Things were great. We were definitely like, 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 Haring too is you can hire two different types of people. Because you don't know exactly what kind of... And there's all sorts of sub-contacts to that that I think changed 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 fouched 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 Grooter 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 sales people, 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 bad sign because the odds are it's tough to do. It's tough to write a night and you know, 95 and 100 will die. If that's the case, then you should assume 95 out of 100 sales people can't do it.
And so to assume that you're just going to find them on the street or in Zipper Grooter or Kerr Builder or wherever else they came, is, you know, the odds are going down fast there. And so for me, my first five sales hires 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 VCs, 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 making partners, you know, give them equity and maybe paying.
Because they're their recommendation probably has more credibility than your old company. Their 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 I 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 the process for hiring reps, how do you stretch that hiring process? The sort of signature moment in a hiring process for a salesperson, we would always have them do a demo. But rather like close to game condition sales call, it's possible. What we used to do is we'd say a pitchers' echo sign, a sales echo sign, has a like 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 at TalkDesk, 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.
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, tell 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? And so we would have people that 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 a 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 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 that have the characteristics that are coachable that you can mold and develop in the way that you do it. Do you ever hire people who haven't been raps before? Where you can coach them and they have the aptitude and skills, but they haven't been raps before?
Obviously 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 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. 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 sales force or 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 and 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. How do you incentivize them financially and all sales reps 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. And 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. And we really raised like five million dollars that they can the lifetime of the company. So we wanted to make sales people profitable as fast as possible.
And what are 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. There's a 98% chance that each hire is probably not going to 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.
And that's what first step is 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? That'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 obviously I believe in running like really a monthly process.
No matter what your ASP is, that's just what I believe. And the startup is the right thing to do. It makes it really hard for them to push heels out and say, oh yeah, I got that's a verbal commit for three months from now. That's not a verbal commit. That's a best key steal. And that's the time frame. It's a best key steal in Bel like you have you run it at 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 in? We can't expect them to hit the ground running from day one. How do we on board reps the right way? If you're a founder in the other founder led sales motion, you know, they did just be at your hip 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 but on them. But like in a startup osmosis is the best way to learn.
Obviously you're using gong or something like that. So you how 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 going to spend on one 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. Do you agree with fire fast when it comes to reps? 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 hire, you made, I don't think there needs to be a like artificial timeline on it, but like a quarter plus some change that you should start to see things going by the end of the second quarter, you win fully, wrap sales person.
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. When you review your mistakes hiring, what are the biggest mistakes you've made in hiring sales reps 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 a like web ex, 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, 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 saying, 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 sales people 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, etc?
And to suring between what looks good on paper and what actually plays is a 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's, there are a lot of other layers to that, you know, 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 sales people that were great.
We brought this guy in as like, oh, you know, this guy's better than them. And he wasn't. He wasn't even in the ballpark of how good they were. And that it can't just for us reinforce like a, this is an ultra talented team. It lets invest 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 for in your company and your system with your customers and and get let them run and then taking them as far as they can. The odds that you're going to hire someone off the street better than that are almost 0.0. What would you rather someone who sold your contract size or someone who sold to your customer? They have to have some have sold within the ballpark. It doesn't have to be a go.
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 9 to 12 month sales cycles and a pretty transactional high velocity sales or 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 kids just crushing it. And then they're, you know, creates this tension. This happened many, many times. I can walk through the number of companies where it's happened.
They have to be separate because they're going to see the, you're this team over here of like sandblown and all these people, you know, just lighting 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 this strategic team, the failure rate is about 99% just in reality.
Because the reality is 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 sandblown can, right? Can I ask Brendan, as a leader, I think deal reviews are very important. How do you think about doing deal reviews? And what's the right way to structure them, organize them, and operate the team to make sure that most efficient?
I mean, most of my deal reviews would start with, you know, obviously we were any communication with the customer. So email, we were really at a point where like all phone calls were being captured, right? But like basically, I was in a deal review. And again, remember for us, we were running a monthly review. We were running every month, we every salesperson had. And this is how I've run it and 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. 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 have commit, you haven't talked to this customer in two weeks. How's that possible, right?
It's like, it makes it very simple. I always look at like customer communication, the correlation to like, how possible a deal is, are like, it's like a 100% correlation. If you have an email 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 in legal or whatever else, you're not closing that deal. Generally speaking, right?
And so that's, that was one of the things that I would always look at is like, you know, where we at with the customer from a communication state, but one of 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 of a deal.
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 yeah, let's take that out of commit, right? Should we put it to close lost? What about lost deal? Someone loses a deal in your team. What do you say to them? What's the answer as a sales leader to the rap who's lost a deal?
If it was a committed deal, I was trying 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 101 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 has 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. Is there a good reason to lose a deal in your mind?
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 the things that 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 to cigarette at the beginning of the sales cycle, where our competitor had a speed 10 waves Sunday. They were in the deal. They had partner and vendor support. They had everything imaginable, where we could undo it. Out of that, surely that ecosystem 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? If there was so sort of proof of concept or pilot. And we were against DocuSign, 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 DocuSign had to lose deals to us, and they didn't understand why. And we were like, yeah, well, you left your flight completely unchecked, man.
There was a deal we were in at Standard and Ports. Sales Force walked DocuSign into the deal, right? Against us. Said, pick that. We went to New York. This sort of overlaps with one of your questions of the talk about a deal where you went outside the box. Sam Blonde, I went to New York, showed up at Standard and Ports 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. We were this kind of bootstrap startup.
Like, I think I told Jason, yeah, like, good first meeting, we're going to meet them again Monday, right? And that's 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. We had our VP of Product fly out. 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, but we're going to pick DocuSign, but yeah, go ahead, make a case. That's how it started.
And we beat him. 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 the head, we'd kind of had to head against DocuSign, and we said, and they did the same thing. You know, they didn't pick him 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 we, at that point, Facebook, this year, Facebook was a 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 leading heavily into that. And they were like, we're stater than poor. So what do we care about Facebook? And I was like, well, I think their evaluations worth more than you, right? That was a judgment call of making that statement. And so DocuSign had just, that's all DocuSign did was go see suite, Salesforce's endorsement. But there were 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 always the way to 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, you know, when they went to sort of provide their feedback back to the C suite, and DocuSign 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 partner investor card with Salesforce and we got our asses kicked. That was one of the most rewarding deals ever. I've ever done a my career because we had no business winning the deal. We had no business even trying. But we just said, we're just gonna do everything right from here and, you know, if we lose, okay? But like if we win, man, how good is that gonna feel if we do win?
I think that's more patient today, you know, the customer evaluation process is so much more layered and, you know, there's so many more stakeholders. I mean, there's even now like a sort of sub vertical and sass of companies that are sort of creating this like. 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 of the norm. You can't really not do it now.
Brandon, I want to move into a quick fire. I love that as a creative story there. That is fantastic. So I see a short statement, you give me your immediate thoughts because that sound okay. So what sales tactics have not changed over the last five years, not changed? Sales people that are independent on an SDR team to drive their own deal flow is going to be a timeless recipe for success. On the flip side, what sales tactics have died Brandon? The kind of outbound SDR models very much in flex.
I think AIs, I really do think the SDR outbound SDR function is gonna fall back under marketing, which is probably where it should be. There was a quantum shift 10 years ago and it's going back, I think it goes back, especially with AIs, the onset of AIs, I think that is a place AIC 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. Then ultimately, what would you most like to change about the world of sales? The stuff I'm working on is a passion project for me.
I've just seen that the good market model for startups is so daunting and becoming more daunting with, there's just so much noise here competing against that the traditional way is 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 is close to the customers possible, as a way to sort of mitigate a lot of risk and how startups grow.
That's the thing I believe most is that going to market on the backs of like a sort of let's just go crack out the 100,000 emails and make 1,000 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, we'll do that, sure. And we have to do it as well as possible. But I never believe that that was also my going to scale and it has not. That's what's most interesting to me.
Final one for you, what one company sales strategy have you been most impressed by recently?
Certainly rippling, I think, pretty impressive what they've done, the CRO used to work on, was on our team at EchoSign back in the day, Matt Plank has done an amazing job there rippling and there's a lot of talent on that rippling team, which is one of the advantages, like when you're the one company just crushing it in a down market, you can really just build super teams, talent-wise, and I think they have. Everyone else is like companies that have adjusted to the state of the state, right?
So like later stage unicorns that are figuring out like, I've crapped things that are slowed and what do we do now? Like talk desk, 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, after a lot of those unicorns, that's hard, right?
When you hit that, those bumps, maybe casins, like how do you bounce out of that and get on a good course again? There's a lot of great pre-seed seed startups and founders out there right now, which I think is always when the market is down, you tend to see a real like bouncy in that area. That's how tech mitigates these things, you know?
When the risk is mitigated between like a big, safe big company and a startup, then you tend to see a lot of super talented people flow into the early stage world, so. Brandon, listen, I always learn a ton from you. I so appreciate the directness, the honesty, and you've been a fantastic guest, my friends. So thank you so much for joining me. Thank you. Appreciate it. Good to see you. I have to say, I just really love doing those tactical shows.
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