Cold open
I I can tell you no great VP of sales is ever 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 out of network, ever. Ultimately, what AI does is probably get put the SDR function back under marketing.
This is 20 Sales
Intro
with me, Harry Stebbings. 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 Brendon Cassidy. Brendon is the former first Head 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, Pipedrive, and Showpad to name a few. But before we dive in,
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Conversation
Brandon I am so excited for this. I wanted to make it happen for a while. It’s been a while since we last chatted, so thank you so much for joining me today.
Also, great to be here. Yeah, I think it was last time we saw each other was maybe in Napa, seamlessly some years ago, I think. Yeah. It’s great to see
it. Brendon, I was young back then, but I to start with a little on you, just the context.
You still You still look good.
Trust me. I look like fricking Benjamin Button, but tell me, how follow 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. CFOs 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 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. were all really young. and 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, 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 into sales, right, where it’s like you are constantly having to of reinvent yourself. You have to be able to be very adaptable to whomever you’re talking to, whomever the customer is.
And that’s something that we had no choice but to to learn to be that. It was be that or be gone. And so, you Great we were these 24, 25 year old kids convincing people with 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 incredible success because nothing will ever be harder than that.
Brendon, how do you analyze where we’re at in the sales playing field today? We got on the call and you said, you know, navigating today. How do you analyze where we’re at today?
The way I would analyze it is anything months months or older, that that we’re in a it’s we’re in a space of clay, of putty, and and 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 to be.
Not a comfortable place to be for most.
What are the biggest things we need to unlearn with sales teams?
I think the 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 breakeven and profitability and 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.
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 And so every hire has to be like a TEDx a TEDx scrapper.
So what now? Is PLG content scaled low CAC 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, referrals, nudges, influence. You know, my conviction is that the 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, in lieu of better alternatives, what what else would you do? I think most people know this probably isn’t going work. It’s expensive. Everyone’s probably going fail generally, but what else do we do The Uber difference between now and 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, you know, you go back years ago and that was five for 10 companies.
How are you gonna, like mass produce some sort of quasi personalized outbound go to market model that’s to engage people that are getting engaged by a thousand other companies the exact same way? That’s the as as existential dilemma everyone’s facing.
Does that not only worsen when you think about AI’s impact on outbound?
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 plus year shift. I I can tell you no great VP of sales is ever 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 and telling them why they’re not coming, but behind the scenes with other sales leaders, they’re to be like, not even close. They know it’s probably a fait accompli at that point. That company is probably not to make it. You know, I’ve probably advised 60 SaaS companies in the last years. You talk to many, many, founders. And the question I ask is like, why’d you start this company? What was the problem that you wanted to solve?
And a lot people can’t answer. They can’t 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, Brendon?
Every company I’ve ever worked at or been a VP of sales 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 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 a fucking call. Right? Like that’s If 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 don’t understand. How are you supposed to know every customer is so different?
because 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 turnoff is on those paths before you ever get on a call with a customer. And if you don’t know them, then, you know, your VP of sales probably isn’t very good.
break I love it. We’re coming out with hot takes today. I understand what you’re saying, though, in terms of the persona, the
language. rocket science. And like, 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 this is the world he sees. Everything I’m to talk about from this point forward, everything I’m to show this person everything, you know, everything’s to be about.
I know that this is this is his true pain here. Like, this is his true opportunity. Every great team I’ve 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 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.
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. my So my teams have always done discovery and everything else, right? If it’s a 30-minute minute call or a 45-minute call, we’re 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 to show them anything if they’re 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,
Miro. Should the founders be the one to do the playbook, to create the first playbook, or can you hire it to to ahead? Yes.
Yes. The the principles of the playbook, for sure, like the broad stroke, the outline, whatever you to call it, right, with but don’t fill it in with 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 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 in ink should probably be written by the VP of sales.
But yeah, you should have a a loosely 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 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. Do you agree with
Jason in hiring two sales reps at a time?
Generally, But again, it’s it’s a case by case basis. Certainly EchoSign did that back in the day, you know, back in the day, which I would say the climate EchoSign was in much more like today than five years ago. Like we were, know, just coming out of the subprime meltdown from an economic standpoint. Things weren’t great. We were definitely like, you know, we didn’t 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 there’s there’s all sorts of sub context to that that I think changed the equation a little bit. Like, are you hiring people you know? You know, like, I believe personally 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 ZipRecruiter 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 honest 100% honest. And so it’s really, really, hard to assess salespeople cult. really, really, hard. We could talk about, oh, like best 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 right? write, you you know, 95 and 100 will die. If that’s the case, then you should assume out out of salespeople can’t do it. And so to assume that you’re just to find them on the street or in ZipRecruiter or CareerBuilder or wherever else they they came is, you know, the odds are going down fast there.
And so for me, my first five sales hires always 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 do you do if you don’t know the five?
So if you have investors, that’s one place to start. Although investors are notoriously bad hiring recommenders. I’m sure I know you’re different. Most investors and VCs, they make a recommendation and my advice would be like, just like, it’s great that you were on the board of a company 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 and make them partners.
You know, give them equity and maybe pay them because their 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 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?
So So let’s say we we enter this hiring process. Even if we do have the network, we still need to go through a process. If you were to structure the process for hiring reps, 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, run like close to game condition sales call. It’s possible. We used to do is we’d say pitch us EchoSign, sell us EchoSign 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, 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 like 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. If what you sell today, if if that’s not a compelling story, then why is it 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 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 SDR is usually about hiring a set of like characteristics because they’re most SDRs are not 10-year year SDRs.
They’re early on in their career. and so you’re looking for for, you know, 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 reps before where you can coach them and they have the aptitude and skills, but they haven’t been reps before?
Obviously, want 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 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 Salesforce for years. I I won’t ever hire that person in a startup. generally.
No comparable motion. right? Versus I’m I’m selling for a Fortune 1,000 tech company. Everyone knows who we are. Everybody has budget versus you get on a call and there’s no acknowledgment that there’s even a problem. The problem that you 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 it’s a legitimate problem? There’s no comps there for like Salesforce 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 that was 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 VPs of sales now.
How do you incentivize them financially and are sales reps coin operated?
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 EchoSign model is a great model for times like this. Pay a really high percentage after they’ve 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 $100,000 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. we only raised like 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? None None of them were a 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 founders make when hiring reps?
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 to work out.
How quickly do you know that it’s not working out?
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.
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, you know, 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 hires I’ve had that didn’t work out, I’m like, I 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, I got that’s a verbal commit for three months from now. That’s not a verbal commit. It’s just that’s a best case deal. and that’s the Monday frame.
It’s a best case deal. And, but like, you you run a a tight sales process without too many stages where deals can hide in.
Onboarding, you of need to give them time and you need training. If I’m a founder, what’s the right way to onboard new sales reps to ensure that I’m not jumping in? We can’t expect them to hit the ground running from day one. How do we onboard reps the right way?
If you’re a founder and you have a founder led sales motion, you know, they just be at your head at every turn. Every sales call you’re on, you know, probably for whatever like a couple weeks where there’s not a lot of expectation put on them. But like, in a startup, osmosis is is the best way to learn. Obviously, you’re using Gong or something like that, right? So you 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 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 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.
Do you agree with fire fast when it comes to wraps?
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, you should start to see things going. By the end of the second quarter, to 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.
When 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 kind of been there, done that hire. He had been like, he was like WebEx. He was a DocuSign. 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 yeah, 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 is 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 discerning between what 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 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 salespeople that were great.
We brought this guy in as like, oh, you know, this guy’s better than them. And he wasn’t They he wasn’t even in the ballpark of how good they were. And that it of just for us reinforced like, hey, this is an ultra talented team and let’s 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, in your system, with your customers, and and letting them run and then taking them as far as they can.
The The odds that you’re to hire someone off the street better than that are almost zero point fucking zero.
What would you rather? Someone who sold your contract size or someone who’s sold to your customer?
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’s sold super enterprise nine to 12-month month sales cycles at a pretty transactional high velocity sales org is not 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, you know, 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 to see the, your, this team over here of like Sam Blonde and all these people, you know, just lighten up the board and they’re to be like, 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 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 Sam Bond can. right?
Can I ask Brendon, 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 they’re 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 weren’t 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 monthly reviews. We were running every month. We 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 commit. You haven’t talked to this customer in two weeks. How’s that possible? Right? Like Like it makes it very simple. I I I always look at like customer communication, the correlation to like how possible a deal is are like it’s like like correlation.
If you haven’t emailed with a prospective customer and usually if 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 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 of the contracting, legal review and all the rest, there’s a very fluid process there. 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 rep who’s lost a deal?
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 be, you know, sit down one on with a salesperson, which I I did every week with every salesperson. Right. And that was we were to spend time and say, hey, like, let’s talk about why this deal was committed and why it it fell out. And, you know, usually there was, you know, the warning signs were just blinking red. in some cases, I should have seen it talking about like that.
Oh, like, you know, this person hasn’t responded to an an email or a call in a week. That’s not 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 to fire anyone for it, But yeah, it’s 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 postmortem on it where you can look back and you can say, here are the things we 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 and cigarette at the beginning of the sales cycle, where our competitor had us beat 10 ways to 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 EchoSign 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, Suite. We were with the evaluators and decision makers, even users, right? If there was some sort of proof of concept or pilot.
And we were going against DocuSign, and DocuSign, was maybe at one level in a deal. One level, and we were at three levels. We were pushing all levels towards each other, and DocuSign would lose deals to us, 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 Poor’s. Salesforce walked DocuSign into the deal, right, against us. Said, pick them. 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 and I went to New York, showed up at Standard and Poor’s on a Friday. No one showed up for the meeting. meeting. and we were like, Jesus, we just flew to New York. We’re staying in a hotel. Like we’re this kind of bootstrap startup. Like I I think I told Jason, yeah, like good first meeting. We’re gonna meet them again Monday. right? And that was what we told that we were able to get them to meet meet us Monday because now they 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 gonna pick Salesforce, but or we’re gonna 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. we were like, yeah, what we would say is, do the same thing that Google did and Facebook did.
And we just walked through all these companies that had evaluated we’d gone head to head against DocuSign that, and they did the same thing. 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 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 leaning heavily into that. and they were like, we’re standard and Poor’s. What do we care about Facebook? And I was like, well, I think their valuation’s worth more than you. Right? That was a judgment call in making that that statement. And so DocuSign had just that’s all DocuSign did was go C-suite Salesforce Salesforce’s endorsement, but there was 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 all we just to do is just beat them. And so we were checking in on every evaluator and 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 DocuSign had never even talked to any of them. They had just sat on their fat asses, right, and said, we played the c 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 in 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 to feel if we do win? I think that’s more prescient today. You know, the 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 subvertical and SaaS of companies that are sort of creating this, like, this salesman, 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 You can’t really not do it now.
Brandon, I to move into a quickfire. I love that as a creative story, though. That is fantastic. So I say a short statement. You give me your immediate thoughts. Does that sound okay? So what sales tactics have not changed over the last five years? Not changed.
Salespeople that are independent on an SDR team to drive their own deal flow is going be a timeless recipe for success.
On the flip side, what sales tactics have died,
Brendon? the kind of outbound SDR model is very much in flex. I think AIs. I really do think the SDR outbound SDR function is to fall back under marketing, which is probably where it should be. There was a quantum shift years ago and it’s going back. I think it goes back, especially with AI, the 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 own that, quite frankly.
At least outbound, like in that that sort of SDR function, that’s to fall under marketing. I think that’s a pretty big quantum shift. Penultimate
one. 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 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 is changing and maybe change forever. The world I to see is 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 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 a 100,000 emails and make a thousand calls. I never really believed in it. it. was like one of those things that everyone just of had to like, okay. Yeah. Yeah. Yeah. Yeah. We’ll do that. Sure. And we have to do it as well as possible, but I never believed that that was ultimately going 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. You know, the CRO used to work on was on our team at EchoSign back in the day. Matt Plank has done an amazing job there at Rippling, and there’s a lot of talent on that Rippling team, which is one of the advantages, like 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, you know, 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, Talkdesk has 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 a lot of those unicorns, that’s hard, right? When you hit that, those bumps, maybe chasms, like, do you bounce out of that and get get on a good course again?
There’s a lot of great pre-seed, 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 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 friend. 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. We get so, so, many messages from founders saying how it’s changed the way that they build their companies. If you to see more behind the scenes, you can check out the full video on YouTube by searching for 20VC. That’s two zero VC. But before we leave you today,
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