Brendon Cassidy: Why You Should Never Hire Someone You Do Not Know in Your First Five Hires | E1124

1. 0:00 – 0:45

   Intro

   1. BCBrendon Cassidy0:00

      Ultimately, what AI does is probably get- put the SDR function back under marketing. For my first five sales hires, I would never hire somebody out of network. I can tell you, no great VP of sales is ever gonna take a job with a company that's dependent on an outbound go-to-market model. That's just... nope. (upbeat music)

   2. HSHarry Stebbings0:18

      Brandon, I am so excited for this. I've 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.

   3. BCBrendon Cassidy0:25

      Also, uh, great to be here. Yeah, I think it was, uh... Last time we saw each other was maybe in Napa, like, some years ago, I think, um, f- for, like, a SaaStr retreat. So yeah, it's great to see you.

   4. HSHarry Stebbings0:35

      Brandon, I was young back then, but I wanna start with a little on you, just a context check.

   5. BCBrendon Cassidy0:40

      You still, you still look good. Trust me. So... (laughs)

   6. HSHarry Stebbings0:42

      Dude, I, I look like fricking Benjamin Button.

2. 0:45 – 3:27

   Brendon’s Background

   1. HSHarry Stebbings0:45

      But tell me, how did, how did you first make your way into the world of sales, and when did you realize you loved sales?

   2. BCBrendon Cassidy0:52

      I was sort of coming into the tech world, uh, around, like, ni- 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, you know... That's the first... Oh, recruiting fees? Yeah, that's just... Yeah, that's not e- There's not... That's a five-second discussion. And so that became, like, you know, an incredible career experience because it was like, "Survive. Okay, how do we survive doing this?" Because no one needs it. Certainly, nobody wants to pay for it. Everyone's firing people. No one's hiring people. Um, what now? Um, and so that forced all of us... We were all really young, and a lot of people, um, sort of didn't make it. Uh, but the- those of us that did, um, it's, you know... I d- I can't ima- You know, it's so foundational in my career, um, that it's... You know, I can't imagine not having gone through it.

   3. HSHarry Stebbings2:08

      What did you take away from it, that really shit hard time? How did it impact your mindset?

   4. BCBrendon Cassidy2:14

      Yeah, I mean, we, we didn't really... 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 were 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. And that, that's a pretty good primer to get into sales, right, where it's like, you know, like, um, y- you are constantly having to kind of reinvent yourself. You have to be able to be, uh, very adaptable to who, whoever you're talking to, whomever the customer is. And that's something that we had no choice but to, to l- to learn to be that. It was be that or be gone. And so, you know, we were these 24, 25-year-old kids, you know, a lot of them from New York. I was from here, in the Bay Area, but, um, convincing people with, you know, 20, 25 years of experience that we had... We knew things that were, um, uncommon. Um, and, you know, that's... Yeah. It was pretty great experience. And every single one of the people that were there, they've all gone on to, like, incredible success, because nothing

3. 3:27 – 5:36

   Changing Landscape of Sales

   1. BCBrendon Cassidy3:27

      will ever be harder than that.

   2. HSHarry Stebbings3:28

      Brandon, how do you analyze where we're at in the sales playing field today? We got on the call and you said, you know, "Ugh, navigating today." How do you analyze where we're at today?

   3. BCBrendon Cassidy3:37

      I think the way I would analyze it is, you know, anything, anything 24 months or older, right? That we're in a, it's, we're in a, a space of clay, you know, of putty. And, and basically, most of what we knew is off the books, has no relevance anymore, um, to how we go to market, to how we built sales teams, um, SDR teams. Everything is... We're very much in a place where it's like, the more you can unlearn (laughs) , your- 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 gonna be. Um, which is not a s- not a comfortable place to be for most.

   4. HSHarry Stebbings4:23

      What are the biggest things we need to unlearn with sales teams?

   5. BCBrendon Cassidy4:26

      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, maybe that will be a thing again someday, but it's no way to run a business anymore. And so, you can't do it that way, right? And every single... I mean, as you know, right? You talk to startups every day. Every startup is, is laser-focused on breakeven and profitability and long-term sustainability, and you can't... You know? The customer... The CAC costs of five years ago are not, not even considerable. Um, the entire outbound go-to-market SDR model has collapsed in the last five years, three years, um, and it doesn't work anymore. Um, a lot of the ways that we have traditionally done sort of, like, mar- sort of marketing demand generation have long since not worked. And so, yeah, it's, it's... Everyone's sort of in the... Uh, a lot of people are in the space of, "Okay, what now?" That's, that's my general state of the state. You c- And so, you ha- Every hir- Every hire has to be, like, a 10X, you know,

4. 5:36 – 7:17

   The Decline of Outbound SDR Model

   1. BCBrendon Cassidy5:36

      a 10X scrapper.

   2. HSHarry Stebbings5:37

      Well, so what now? Is PLG content, scaled, low-CAC the only way forward?

   3. BCBrendon Cassidy5:44

      Well, I mean, I think that's, that's probably a podcast series. Um (laughs) , uh, I don't know that I can answer it in one soundbite. 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, um, to accelerate yourself in the market via, like, relationships, referrals, nudges, influence. Um, but yeah, um, you know, my conviction is that the, uh, the whole, like, outbound sort of SDR model is, is over.

   4. HSHarry Stebbings6:17

      Do you think the world gets that? Because there's still many outbound SDR models and teams are still operating in that way.

   5. BCBrendon Cassidy6:23

      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, right? So I think it's like, okay, I think most people know this probably isn't gonna work, it's expensive, um, everyone's probably gonna 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, you know, you go back 15 years ago and that was five or 10 companies. Um, and so how are you gonna, like, mass produce some sort of out- quasi-personalized outbound go-to-market model that's gonna engage people that are getting engaged by a thousand other companies the exact same way? Um, yeah. That's, I think that's the as ex- as existential dilemma

5. 7:17 – 9:05

   Impact of AI on Outbound Sales

   1. BCBrendon Cassidy7:17

      everyone's facing.

   2. HSHarry Stebbings7:18

      Does that not only worsen when you think about AI's impact on outbound?

   3. BCBrendon Cassidy7:22

      That's an extraordinarily fluid discussion, Eric. Um, I think ultimately what AI does is probably get, put the SDR function back under marketing ultimately. When you can maybe accomplish the tasks of multiple in one, with one, um, I think 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, um, into sales from marketing, which has been a 10-plus-year shift. And that's, I, I can tell you no great VP of sales is ever gonna take a job with a company that's dependent on an outbound go-to-market model to grow. That's just, nope. Bye-bye. It's, it's ... And they may be more, uh, circumspect with the founder and, and telling them why they're not coming. But behind the scenes with other sales leaders, they're gonna be like, "Not even close." Because they know the, the, they know it's probably a fait accompli at that point. That company's probably not gonna make it. And so more and more companies, right? Like I, I, I talk to, you know, I've probably advised 60 SaaS companies in the last 10 years. You talk to many, many founders, and the question that I a- ask is like, "Well, why'd you start this company," right? "What was the problem that you wanted to solve?" And a lot of people can't answer. Wh- they can't a- 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. Um, or why they wanted to s- why they were the person to solve that problem. So ...

   4. HSHarry Stebbings9:02

      We always hear the term sales playbook. Uh,

6. 9:05 – 10:36

   Defining a Sales Playbook

   1. HSHarry Stebbings9:05

      I'll just love to hear, how do you define what a sales playbook is today, Brandon?

   2. BCBrendon Cassidy9:09

      I mean, it's th- it's not, it's not a canned response. It's, it's every company I've ever worked at or been a VP of sales for, their playbook was completely different than the one before or the one after, right? So it's, um, it dep- it depends on a lot of factors. Depends on, um ... But yeah, I think it's a basic of here's our customer, here's our idea, h- here, here are our different customer personas, uh, 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, 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, um, 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. Uh, and I think tha- that is pretty unique in my career. And that's why, you know, these companies that are, like, spend hours and hours doing, um, discovery calls, especially in this day and age, it's like I can't ... How do you not know (laughs) 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? (laughs) Like, that's just, that's 0.0 lev- ... If you need to get on a call and spend two and a half hours w- doing discovery on your own behalf, then you shouldn't be on ... You're not

7. 10:36 – 12:20

   Importance of Customer Understanding

   1. BCBrendon Cassidy10:36

      on my sales team.

   2. HSHarry Stebbings10:37

      I don't understand. How are you supposed to know what customer ... Like, every customer's so different.

   3. BCBrendon Cassidy10:42

      It's because-

   4. HSHarry Stebbings10:42

      You could be-

   5. BCBrendon Cassidy10:43

      ... like, you're, you're, you're an expert. (laughs) Right? These are people that you're talking to every day. Right? They're, it's, they're, their, their problems and their pain is not infinite. Right? So it's like usually there's like, maybe there's three different paths. What the opportunity or problem here is, is one of three paths or four paths, and you better know exactly what those look like and what every turnoff is on those paths before you ever get on a call with a customer. And if you don't know them, then, you know, your VP of sales probably isn't very good.

   6. HSHarry Stebbings11:15

      I, uh, I, I, I love it. We're coming out with hot takes today. Uh, I, I understand what you're saying though, in terms of the persona, the, the language-

   7. BCBrendon Cassidy11:22

      It's, it's not rocket science, and like, it's not ... If you, 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 more, you should know as much about them as they know about themselves. Um, and you should know, you know, based on like, you know, how the beginning of the call goes, you know, okay, I know this, I know that this is, this is the world he sees. That's what everything I'm gonna talk about from this point forward, everything I'm gonna show this person, everything, you know, everything's gonna be about, you know, I know that this is, you know, this is his true pain here. Like, this is his, uh, true opportunity. Every great team I've been on knew that.... they knew it, and they, they had it mapped out, and there was never ever a scenario where you got on a call and you were like, "Oh my God, I never thought about that, that that could be a problem," right? (laughs) Like, "What are we

8. 12:20 – 14:36

   How Discovery Should be Like

   1. BCBrendon Cassidy12:20

      fucking doing, man?" (laughs) 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- I've advised for companies, and that's all they did was discovery, right? 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? (laughs) It was like, you know, it was like some sort of purity test, right? Um, and like, to me, discovery is a means to an end, right? Discovery is, you know, like if you're expecting to close deals in discovery, never seen it once in my life, ever, um, both as an advisor, consultant, running teams. Like you sh-... Discovery's 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 gonna, you know, we're gonna map it out, lay it out, and play it out, right? The- But like to, especially now, where you're competing with 1,000 other companies for attention for a buyer, and you're not actually gonna show them anything, if they're gonna give you their time, like you're fucking nuts, (laughs) like if you do that, in my opinion. But, you know, trust me, there's plenty of people that completely disagree with my take there, so... And th- and god bless 'em, you know?

   2. HSHarry Stebbings13:45

      Should the founders be the one to do the playbook, like to create the first playbook?

   3. BCBrendon Cassidy13:50

      Yes, the, the principles of the playbook, yeah, for sure, like the broad stroke, the outline, whatever you wanna call it, right? With... But don't fill it in with, uh, 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 gonna be in as the first salesperson, you'll probably have seen it. You'll s- have seen them in action multiple times. Ultimately, the playbook, um, the f- in ink should probably be written by the VP of sales. But yeah, you should have a, you know, sort of a loosely, uh, built playbook as a founder. I mean, I'm a f- co-founder. We d- we close 100%. You know, we just became profitable in my startup. We close all of our deal, own deals, myself and the co-founder. We don't have any salespeople.

9. 14:36 – 15:26

   Hiring VP of Sales First vs. Sales Reps

   1. BCBrendon Cassidy14:36

      Well, other than us.

   2. HSHarry Stebbings14:37

      I'm a hypothetical founder in this situation, and you're advising me. Um, should I hire a VP of sales first or should I hire sales reps first?

   3. BCBrendon Cassidy14:45

      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 a VP of sales as your first sales hire. It j- obviously Jason Lumpkin has, has evangelized that. I gr- agree with it, generally speaking. Um, 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. Um, but obviously, the best SaaS companies have pretty active

10. 15:26 – 19:32

    Hiring Multiple Sales Reps at Once

    1. BCBrendon Cassidy15:26

       founders and early go-to-market.

    2. HSHarry Stebbings15:27

       Do you agree with Jason in hiring two sales reps at a time?

    3. BCBrendon Cassidy15:30

       Generally, but again, it's, it's a case-by-case basis. If you hired, I mean, that, the, the advantage, 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, right? Like we were, you know, just coming out of the subprime meltdown w- from an economic standpoint. Things weren't great. Um, we were definitely like, you know, trying, you know, we didn't want to raise another dime of funding, and so we were trying to grow or get, you know, we were trying to drive profitability through growth, right? Efficient growth. Ideally, I mean, one of the advantages of hiring two is you can hire two different types of people. Um, and, you know, like, 'cause you don't know exactly, like what kind of... And I, I mean, there's all sorts of, uh, sub varyi- uh, sub-context to that, uh, that I think change the equation a little bit, like are you hiring people you know, right? Like, mm, you know, like I believe personally, you know, for my first five sales hires, I would never hire somebody out of network, ever. Um, I either, like, somebody that I know and someone that's worked for me or somebody that's vouched for by somebody I trust, um, those would be, 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 (laughs) or whatever, you know, like wherever else you found this person. And the odds of you, like, being able to, you know... I mean, salespeople are notorious liars. Um, I've never, I've never seen a re- a sales resume that was 100% honest. And so it's really, really hard to assess salespeople colt really, really hard. We could talk about, oh, like best practices and processes, but it's just a shot in the, it's just a, you know, it's just a shot in the shit, you know? (laughs) Um, you know, like there are things to de-risk it, but basically if you, if you, your first sales hires are just off the street, it's a bad sign, um, because the odds are that they're not, you know... It's tough to do. It's tough to do. It's tough to, as you know, right? Nine, you know, 95 in 100 will die, probably is the current r- rate of things. If that's the case, then you should assume 95 out of 100 salespeople can't do it. Um, and so to assume that you're just gonna find them on the street or in ZipRecruiter or CareerBuilder or wherever else they c- they came is, you know, the odds are going down fast there. And so for me, my first five sales hires always gonna come through p- uh, people vouched for by people I know and people that I trust.... where there's some skin in the game.

    4. HSHarry Stebbings18:14

       So what do you do if you don't have a network? What do you do if you don't know the five?

    5. BCBrendon Cassidy18:18

       So if you have investors, quote, "Hypothetically," you have some access to some sort of network. So if you have investors, that's one place to start, although investors are u- notoriously bad hiring recommenders. I'm sure, I know you're different-

    6. HSHarry Stebbings18:32

       (laughs)

    7. BCBrendon Cassidy18:33

       (laughs) But most, most investors and VCs, like, they make a recommendation, and my advice would be, like, just, just, just, "No." Like- (laughs) it's great that they work, you know, that you were on the board of a company 15 years ago, and they were great then and stuff. But like, um, so I would say, yeah, like, i- if, 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, right, um, that have, you know... And make them partners. You know, give them equity, maybe pay them, because their, their recommendation probably has more credibility than your own company, right? Um, their voice has more visibility than you. And so go out and create, have a five-person advisory team that's, you know, that's great. Um, how do you do that? Well, (laughs) it's, on some level, at some point, people have to figure some of

11. 19:32 – 23:44

    Structuring the Hiring Process for Sales Reps

    1. BCBrendon Cassidy19:32

       it out for themself, right? So.

    2. HSHarry Stebbings19:33

       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?

    3. BCBrendon Cassidy19:45

       I've always... For me, the, the sort of signature moment in a hiring process for a salesperson, I would always, we would always have them do a demo, right? We'd always ha- or have them run a s- like a s- run a, like, close-to-gain condition sales call as possible. Um, what we used to do is we'd say, "Okay, sell, you know, 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," right? Like, you know, th- whatever their product is today have... Run this sort of mock sale or mock pitch based on what they currently sell or have, have most recently sold. And so that was sort of the evolution of that. And basically, that was the, ultimately for any candidates, we could talk about how they would get to that stage, but like, that was the determining factor. And like, so at Talkdesk, we had, like, a panel. It was 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." Um, and that was sort of how we would, you know, go up or down in that process. Obviously, that creates a pretty high standard, but, m- the logic was sell me what you sell today. If what you sell today, if you, if that's not a compelling story, then why is it gonna be compelling here, right? (laughs) Like, you know? And so we would have people that we were like, "Yeah, we really like this person," um, you know, i- uh, going through the interview process, and they would, they would do their pitch and be like, "Yeah, that's no way." (laughs) Like, 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.

    4. HSHarry Stebbings21:29

       Mm-hmm.

    5. BCBrendon Cassidy21:29

       Um, that's a pr- I think that's a pretty good litmus test for a hire. I would never do it. I would never hire a salesperson without doing that. I mean, there's, for, like, SDRs, there's obviously, there's a whole other set of stuff for an SDR, but hiring SDRs is, is usually about hiring a set of, like, characteristics, because they're mo- most SDRs are not ten-year SDRs. They're early on in their career, and so you're looking for pe- you know, people that have the characteristics that are coachable, that you can mold and develop in the way that you do it.

    6. HSHarry Stebbings22:00

       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?

    7. BCBrendon Cassidy22:07

       Obviously, I want to hire in-network for my first three to five hires. Um, you know, people that are... 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, and they can, th- 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, um, versus, like, "Oh, this guy was at Salesforce for 10 years." I, I won't ever hire that person at a startup generally, right? Because there's no- no comparable motion, right? Versus I s- I'm selling for a Fortune 1000 tech company. Everyone knows who we are. Everybody has budget, um, you know, versus you get on a call, and there's no acknowledgement that there's even a problem. Like, the problem that you want to solve, there's no agreement or even understanding that that problem exists. Can you live in that world, um, where you have to, you know, you have to convince them it's a, it's a legitimate problem, um, to even examine? Like, (laughs) 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. Um, so yeah, I'm looking for people that, 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, uh, every single

12. 23:44 – 25:24

    Financial Incentives for Sales Reps

    1. BCBrendon Cassidy23:44

       one of them are VPs of sales now.

    2. HSHarry Stebbings23:45

       How do you incentivize them financially, and are sales reps coin-operated?

    3. BCBrendon Cassidy23:49

       I think that's one of those... That's a super fluid concept, (laughs) right? Because I think the way that we've compensated salespeople, like, five years ago is probably, like, null and void now. Um, obviously, I don't s- I'm not paying any salespeople right now, (laughs) like.

    4. HSHarry Stebbings24:05

       (laughs)

    5. BCBrendon Cassidy24:06

       Um, we're, you know, we're founders. We close deals. We're not paying ourselves commission for those. Um, I would say the EchoSign model...... is a great model for times like this, right? Which was pay a really high percentage after they paid for the, after they paid for themself, essentially, right? Um, and so, um, every sales rep... That's how we did it. Every sales rep had a, like, full, full operational cost, you know, of like this is what they made, this is their salary and, uh, benefits, and this is what it costs. And so, if you closed on $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, I mean, it probably averages out to something more normal, but like that was the way we looked at it was. Um, you know, because we were, we were m- not bootstrap, but I mean, we only raised like $5 million, I think, in the lifetime of the company, so... and none after I joined. And so, like every... you know, 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 themself, right? That none of them were a cost center. Um, so I would say that's probably a pretty good model for the current timing, time,

13. 25:24 – 27:19

    Common Mistakes in Hiring Sales Reps

    1. BCBrendon Cassidy25:24

       time we're in now.

    2. HSHarry Stebbings25:25

       What are the biggest mistakes that founders make when hiring reps?

    3. BCBrendon Cassidy25:29

       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. It's just, you know, there's a 98% chance that, that each hire is probably not gonna work out.

    4. HSHarry Stebbings25:42

       How quickly do you know that it's not working out?

    5. BCBrendon Cassidy25:44

       You generally know in a quarter. You know in a quarter if, you know, like you might give them more time, so like 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.

    6. HSHarry Stebbings25:57

       What are the signs that it's not working out?

    7. BCBrendon Cassidy25:59

       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, you know? Like at some point, they sh- y- that's the first step is like can they run the call in the way that you want it done without where you can be involved and help in, in... 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 felt like I'm like I sh- I have to jump in here 'cause it's going sideways a lot, and I have to take over and fix it. And it's just not... eh, it doesn't seem to... You know, they don't seem to be getting better at it. Um, and then, you know, like obviously, like I've ra- you know, I believe in running like really, like sort of a monthly, tight monthly sort of process, no mat- really, uh, quite frankly, no matter what your ASP is, that's just what I believe in a startup is the right thing to do. Because it, it's r- it makes it really hard for them to push deals out and say, "Oh, yeah, yeah, I got... That's a verbal commit for three months from now." Um, well, that's not, that's not a verbal commit, it's just that's a best case deal, and that's the timeframe it's a best case deal, and but like... You know, when you... and I... you know, you have... you run a, a tight sales process without too many

14. 27:19 – 29:05

    Onboarding Sales Reps

    1. BCBrendon Cassidy27:19

       stages where deals can hide in.

    2. HSHarry Stebbings27:20

       Onboarding. You kinda 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?

    3. BCBrendon Cassidy27:35

       If you're a founder and you have a founder-led sales motion, you know, they need to just be at your hip at every turn, right? Every, uh, you know, every sales call you're on, you know, probably for a few, uh, like a couple weeks, right? Where there's not a lot of expectation put on them, but like, you know, I mean, there's n- in a startup, osmosis is, is the best way to learn, right? So, you know, have them on your hip. Obviously, you're using Gong or something like that, right? So you ha- you should have a bank of call recordings and demos and, you know, very easy way to, like, analyze and synthesize that data. You should, uh, you know, have your salesperson listen to, like, every sales call, like within reason, right? Or re- uh, 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 s- people are gonna spend a lot of money on, I think, generally. Um, so yeah, I would say osmosis. (laughs) Um, you know, don't have 'em, you know... uh, without it, you know, it's, they're almost certain to fail, certainly. And that's, you know... Obviously, I was involved in the very, in the early days of Gong. That is, that is something that's out there now I think that's f- critical for onboarding new salespeople, right? The ability to, you know, sort of tap into like historical record of calls and data and learnings and all that kind of stuff. Um, yeah, I would say that's it. Just get them on your hip. Have them listen to every call that

15. 29:05 – 29:57

    Firing Sales Reps

    1. BCBrendon Cassidy29:05

       you have on the books.

    2. HSHarry Stebbings29:06

       Do you agree with fire fast when it comes to reps?

    3. BCBrendon Cassidy29:10

       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. Um, and so if you believe in the hire you made, I don't think you need to... I don't think there needs to be a, like, artificial timeline on it. Um, but like, yeah, I'd say a quarter, you know, a quarter plus some change, that you should start to see things going, you know? And like we would always say, "By the second quarter, you wanna, you wanna f- by the end of the second quarter, you want a fully ramped 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, yeah, maybe you let them go. But like there's probably...

16. 29:57 – 34:27

    Brendon’s Biggest Mistakes in Hiring

    1. BCBrendon Cassidy29:57

       you're probably a big part of the reason why.

    2. HSHarry Stebbings29:58

       When you review your mistakes hiring, what are the biggest mistakes you've made hiring sales reps?

    3. BCBrendon Cassidy30:04

       Being, uh, enticed by the resume, right? By the experience. Like, um, you know, you... We hired this person at EchoSign who was like this kind of been there, done that hire. He was at like WebEx, he was at DocuSign, he was, you know, he was at Salesforce. We're like, "Wow, this guy's amazing," right? 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?

    4. HSHarry Stebbings30:33

       (laughs)

    5. BCBrendon Cassidy30:34

       And, yeah, that was, like, a red flag. Whoa, okay. Um... And so, um... 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 say- seeing, like, um, bo- 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... Are y- i- is that who you're getting? Right? Even when the resume looks amazing, are you still getting that person, or was that person just right time, right place, lucky, et cetera? And discerning between what, what looks good on paper and what actually plays is, uh, uh, super complex. And it's a complicated thing to, to, to under- you know? And so most people hire a resume with, you know, 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, um, layers to that. Like, you know, like did you do your due diligence on that person? Did you talk to people that knew them, had worked with them that, you know, like, that, that could vouch for who they were? And, or not, maybe who they were not. Which that has layers, (laughs) by the way, right? Um, but like, yeah, I would say that's, you know, this particular hire I'm talking about, we hired him, and he was gone in a month for, you know... When he w-... 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 kind 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, right? Like, um, you know? And so that's, 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 g- letting 'em run, and then taking them as far as they can, um, in their career. Because the odds that you're gonna hire someone off the street better than that are almost zero point fucking zero. Like, they have to have some, you know, have sold within the ballpark, right? Of like, it doesn't have to be like, oh, well, you know, it's 5K off in ACV or something. But yeah, they have to have sold somewhat similar type of sort of price point and sale cycle, like velocity-wise and all that kind of stuff. It doesn't have to be exact. You know, hiring somebody that's sold, you know, super enterprise, nine to 12-month sales cycles in a, you know, like pretty transactional, high-velocity sales org is not gonna 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 the 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 can walk through the number of companies where it's happened, even ones that I wasn't at. They have to be separate, because they're gonna see the, your, this team over here of, like, Sam Blonde and all these people, you know, like, just lighting up the board. And they're gonna be like, "Goddamn, man, I need to do something here," you know? (laughs) And most the time, it just doesn't work, to be honest. Most the time, you try to, like, overlay this strategic team, um, and they, uh, the tr- the f- the failure rate is about 99%. Um, just in reality, right? 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 it as good as Sam Blonde can,

17. 34:27 – 36:47

    Deal Reviews

    1. BCBrendon Cassidy34:27

       right? (laughs)

    2. HSHarry Stebbings34:27

       Can I ask, Brandon, 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?

    3. BCBrendon Cassidy34:40

       I mean, most of my deal reviews would start with, you know, obviously we were, any communication with the customer, right? Um, so email. We weren't really at a point where, like, all phone calls were being captured, right? But like, basically, if there- I was in a deal review, and again, remember for us, we were r- running a monthly reviews, right? Like, we were running every month, we, every salesperson had... And this is how I've run it in every s- company I've ever been in, and it's worked 100% of the time with various, varied, varying 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, right? So like, you're breaking a deal down, and you're like, "Yeah, so here's a deal you haven't commit, you haven't talked to this customer in two weeks." So like, how could that poss- how's that possible, right? (laughs) 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, there's a, it's like 100% correlation, right? And so if you haven't emailed with a prospective customer in, you know... Usually more, 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, right? Generally speaking, right? And so that's, 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, generally. (laughs) Right? Something's wrong, right? Something's wrong. Not all the time, but usually that was my sort of instinct around it.... is, like, y- there has to be constant communication with the customer if a deal's, you know, when you talk about all of the contracting, legal review, and all the rest. There's th- a very fluid process there, and when there's big gaps in communication, um, I'm like, "Okay, so yeah, let's take that out of commit, right?

18. 36:47 – 43:32

    Dealing with Lost Deals

    1. BCBrendon Cassidy36:47

       Should we put it to close lost?"

    2. HSHarry Stebbings36:48

       What about a lost deal?

    3. BCBrendon Cassidy36:50

       Mm-hmm.

    4. HSHarry Stebbings36:50

       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?

    5. BCBrendon Cassidy36:56

       If it was a committed deal-

    6. HSHarry Stebbings36:59

       Yeah.

    7. BCBrendon Cassidy36:59

       ... the, the consequences, not consequences, but w- you know, I always tried to view those like they have to feel that, or what's the point of committing deals, (laughs) right? And so, you know, we treated that, you know, that was a big deal, right? That was gonna be, you know, sit down one-on-one with a salesperson, which we- I did every week with every salesperson, right? And that was, we were gonna spend time, and say, "Hey, like, w- 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 obvious. B- blinking red, and in some cases, I should've seen it. You know? Like, talking about, like, that, oh, like, you know, this person hasn't responded to a, an, an email or a call in a week. That's not gonna close. But yeah, uh, they would, if it was a committed deal that didn't close, you know, I was f- I've always felt like that, you know, they have to feel that some, some, you know. It doesn't have to be, like, I'm not gonna fire anyone for it, um, but yeah, it's gonna be a discussion.

    8. HSHarry Stebbings37:59

       Is there a good reason to lose a deal, in your mind?

    9. BCBrendon Cassidy38:02

       It usually, when you lose deals, it's, it's, it's not about, it's what you didn't do, you know, five steps prior, right? Or what you didn't establish, or, you know, 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 that we had, we really didn't solidify these things." There were stones unturned, um, is usually when you do, when you analyze why you lost a deal. And so, we were always, you know, our motto was always like, "Let's turn over every stone." We were so good that we could, uh, walk into deals where we were basically, you know, given a blindfold and a cigarette at the beginning of the sales cycle, right? Where our competitor had us beat ten ways to Sunday. They were in the deal, they had vent- they had partner and vendor support, they had everything imaginable, um, where we could, you know, we could undo it. Out of that, shortly, that EchoSign team, one of the things that we did, I think at a, which was not the norm at that time, maybe it is now, is we were, we're sell- we were in every layer of the deal, right? We were at the s- we were in the C-suite, we were with, uh, 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, and we were, you know, we were pushing all levels towards each other, right? And DocuSign would lose deals to us and they didn't understand why. And we were like, "Yeah, well, you know, you left this, you left your flank completely (laughs) you- you left your flank unchecked, man," right? So... And there was a deal we were in at Standard & Poor's. Salesforce walked DocuSign into the deal, right? Against us. Said, "Pick them," right? (laughs) Um, 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 Blond and I went to New York, um, showed up at Standard & Poor's on a Friday. No one showed up for the meeting. (laughs) That's... And we were like, "Jesus, we just flew to New York, we're staying in a hotel," (laughs) like we're this kind of bootstrap startup. Like, (laughs) and so, 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 that they, for whatever reason, they all, none of them showed up. We had our VP of product fly out (laughs) . 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," right? (laughs) That's how it started, and, uh, and we beat 'em. 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. Um, and so, we were like, "Yeah, like, what we would say is, you know, like, do the same thing that Google did and Facebook did," and we just walked through all these companies that had evaluated, that had co- we'd gone head-to-head against DocuSign at, right? And we said, and, and they did the same thing, right? They didn't, you know, they didn't pick 'em 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. I'll h- you know, we walk away h- happily, quite frankly. Um, and if we win it, then you pick us, and you kick them out of the room, (laughs) um, because, you know, like, that's the same decision that everyone else made. And so, we, at that point, Facebook, this year, Facebook was of super high profile, right? Facebook was like, the hottest company in the world. So we were really, and we had just beaten DocuSign and Facebook, we were really leaning heavily into that, and they were like, "We're Standard & Poor's, what do we care about Facebook?" And I was like, "Well, I think their valuation's worth more than you, right?" (laughs) Um, anyways, that was (laughs) , that was a good judgment call in making that, that statement. But like, yeah, we, we just beat, and so DocuSign had just, that's all DocuSign did was go C-suite, Salesforce's endorsement, but there was al- there were two other layers of people, right? Evaluators and users that were, and then we just, basically Sam and I were like, "Yeah." And at that, at this point, it's like, it's just, that's all we just wanted to do is just beat them, (laughs) right? And so, we were checking in on every evaluator and user every day, right? Like literally, it was like, rehearsing a witness statement with them, (laughs) 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 'em, right? They had just sat on their fat asses, right, and said, um, "Yeah, we, we played the C-suite and we played the partner investor card with Salesforce and we got our asses kicked." Um, and that was w- 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. Um, 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's that gonna feel if we do win?" That was back 13 years ago, a lot, you know, 12 years ago. That was pretty innovative. I think now it's more the norm. You, you can't

19. 43:32 – 48:02

    Quick-Fire Round

    1. BCBrendon Cassidy43:32

       really not do it now, so...

    2. HSHarry Stebbings43:33

       Brandon, I wanna move into a quick fire. 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?

    3. BCBrendon Cassidy43:42

       Sure.

    4. HSHarry Stebbings43:43

       So what sales tactics have not changed over the last five years? Not changed.

    5. BCBrendon Cassidy43:49

       Salespeople that are in- dependent on an SDR team to drive their own deal flow is, uh, gonna be a timeless recipe for success.

    6. HSHarry Stebbings43:57

       Tell me, on the flip side, what sales tactics have died, Brandon?

    7. BCBrendon Cassidy44:02

       Kind of outbound SDR models, very much in flex. I think AIs... I th- 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 ba- 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, right? To sort of take demand generation out of sales, which I don't think any VPs of sales really wanna own that, quite frankly. Um, at least outbound, like in that, uh, that sort of SDR function. Um, I think that's gonna fall under marketing and I think that's a pretty big quantum shift.

    8. HSHarry Stebbings44:41

       Penultimate one. What would you most like to change about the world of sales?

    9. BCBrendon Cassidy44:44

       The stuff I'm working on is a passion project for me, um, because I've just seen that the, that go-to-market model for startups is so daunting. There's just so much noise you're competing against that the traditional ways to get in front of customers is cha- is changing and maybe change forever. And so, yeah, that's, you know, I just... Yeah, the, uh, the world I wanna 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 lotta risk in, in how startups grow. That's the thing I believe most in, right? 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 1,000 calls," I never really believed in it. It was like one of those things that everyone just kinda had to, like, "Okay, yeah. Yeah, yeah, uh, yeah. We'll do that, sure." And what you have to do as well as possible, but I never believed that that was ultimately gonna scale and it has not. That's what's most interesting to me.

    10. HSHarry Stebbings45:47

        Final one for you.

    11. BCBrendon Cassidy45:49

        Yeah.

    12. HSHarry Stebbings45:49

        What one company sales strategy have you been most impressed by recently?

    13. BCBrendon Cassidy45:53

        Certainly Rippling. I think pretty impressive what they've done. Um, you know, the CRO who used to work on, was on our team at EchoSign back in the day, Ma- uh, Matt Plank? Has done an amazing job there at Rippling. Um, so that would be the one, number one. And certainly there's a lot of people on that Rippling team I know and there's a lot of talent on that Rippling team, um, which is one of the advantages, uh, like when you're the one company just crushing it in a down market, is you can get, you can really just build super teams, talent-wise, and I think they have. Everyone else is like companies that have adjusted (laughs) 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 is certainly like a company that w- had a really, went through a tough period and they've now completely course corrected from everything that I know. Like doing really, really well now. And that's hard to do. I think, eh, for the, a lot of those unicorns, that's hard, right? When you hit that, those bumps, big bumps, maybe chasms, like how do you bounce out of that and get back on a chart, get on a good course again? Um, you know, there's a lot of early stage startups. There's a startup called Lantern I love that's like a sort of a Rippling for the sales cloud type of play. And a lot of those just incredible early founders, a lot of early traction. Um, 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, um, bouncy in that area. That's like the, you know, that's sort of the tech. That's how tech mitigates these things, you know? Is e- when the risk, when the, 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 st- into the early stage world, so...

    14. HSHarry Stebbings47:50

        Brandon, Brandon, listen. I always learn a ton from you. I so appreciate the directness-

    15. BCBrendon Cassidy47:54

        (laughs)

    16. HSHarry Stebbings47:54

        ... the honesty, and you've been a fantastic guest, my friend. So thank you so much for joining me.

    17. BCBrendon Cassidy48:00

        Thank you. Appreciate it. Good to see ya.

Episode duration: 48:02