For Sales Leaders

The Sales Playbook for 2022

Jason M. Lemkin (SaaStr) meets with Brendon Cassidy (CoSell) to discuss the "Sales Playbook for 2022". 


 

Jason M. Lemkin (SaaStr)

Brendon Cassidy (CoSell)

 

Transcription below...

Jason Lemkin:

Hey, everybody at SaaStr. I wanted to bring back one of the truly OG members of the SaaStr community, Brendon Cassidy to talk a bit about sales in 2022 and beyond. Brendon and I worked together since the dawn of SaaStr... Not really. But, for quite a long time, he was VP of Sales. He was first Head of Corporate Sales at LinkedIn, then our Head of Sales back in the Adobe Sign, EchoSign. Then, VP of Sales at $10 billion Talkdesk. And he helped build the sales teams at Gong HackerRank, a bunch of other leaders.

Jason Lemkin:

And today, he's also co-CEO of a next generation SaaS referral platform called CoSell, which we'll chat a little bit about. So, I think if you've been part of SaaStr for over the years, if you came to say zero, it's SaaStr annual this year, you've read a lot of Brendan's thoughts, which I think have been many of the iconic ones and building sales teams initially, inside sales now, sales teams. And I just want to use this time to catch up on as we leave the COVID world, where the heck sales is going to be? So, Brendon, thanks for joining us today.

Brendon Cassidy:

Yeah, absolutely. Excited to hear we're leaving the COVID world too. So, that's...

Jason Lemkin:

We're at least in the next 18 months. I think...

Brendon Cassidy:

It's hard to tell from the cottage. It doesn't necessarily give you that macro view. But, I think you're right.

Jason Lemkin:

Yeah, I mean, everything's changed from distributed teams to sales stacks, to growth, right? It's just not a world.

Brendon Cassidy:

Yup.

Jason Lemkin:

We're not in the world, at least in cloud and SaaS, we're not in the world we were before COVID anymore, are we? It's a different world.

Brendon Cassidy:

No, I mean, we're not. I don't know that that's just because of COVID. I think, it's general sort of the SaaS space in general. But, yeah, it COVID. Certainly, has helped accelerate some things, for sure.

Jason Lemkin:

Yeah. So, let's chat a little bit first about hiring because there's so many SaaS companies today doing hiring, right?

Brendon Cassidy:

Mm-hmm (affirmative).

Jason Lemkin:

I'm wanting to chat about a couple of things. Let's start... Let's go with like A's and sales teams, and then talk about our classic VP of Sales like, that we've been chatting about for years. Sales reps... But, first, let's talk about comp, do you see inflation in sales reps comps? And how do we pay for some of the high comp expectations in sales reps? There's only so many dollars that come in for each deal, right? How much of that 50k deal? Can we give more than all of it to the sales reps? How are you seeing inflation expectations going on with sales teams, if at all?

Brendon Cassidy:

Yeah. I mean, I don't think there's any secret. It's not an accident that that usually the best performing sales teams, pay their salespeople really well.

Jason Lemkin:

Right.

Brendon Cassidy:

So, I'm a big believer in one plus one equals two. And so, everybody does it differently. Obviously, we've done it. We had a unique way. We did it at EchoSign that actually worked out really well. But, yes, you have... To me, from the view of a sales leader, having some sales... Usually, not every salesperson is making half a million dollars on startup, but having some salespeople that just absolutely crush it, and are the highest paid people in the company is almost all net good.

Jason Lemkin:

Yes.

Brendon Cassidy:

They're probably, you're paying them a lot. Maybe, they're even overpaid, but there's a cascading effect of that not just within your own team, but like your hiring brand and all the rest, right? I think, to me, I don't know why people... There's a lot of companies that are trying to cut at the margins of that. And I think it's like, I don't understand that mentality because it's hard enough as it is, but when you're saying, how do we pay the least amount for the people that are the most successful? That kind of thing.

Brendon Cassidy:

It just seems contradictory because it's hard enough, right? I mean, like most startups are not super successful. So, it's like, a lot of times it's the ones that don't... That are the most confounding ones are like, they don't have a lot of successful salespeople. So, why are you sitting around thinking about how you can pay your salespeople less? That kind of thing.

Jason Lemkin:

True. Yup.

Brendon Cassidy:

Yeah. That's the way I look at it. I want my top salespeople to make a crap load of money because that's a proof for other people, right? And that becomes part of your hiring brand of like, certainly, at EchoSign that was a big deal. We were talking about this kid Sam Blond, making a ton of money and we're like, "Go talk to him, ask him how much he makes."

Brendon Cassidy:

And for more experienced salespeople, Paul Donati, or Reilly Devine, or others, that was big. That was a big deal. That you said, "Hey, if Sam can make a lot of money here. I think I could make a lot of money here." Not that they view themselves as more talented with Sam, by the way. It's a proof, right?

Jason Lemkin:

Yeah, for sure.

Brendon Cassidy:

Because in any startup... Certainly, startup, I mean, there's a difference between 10 person sales team and a 100 or 200 person team that's scaling, but like, yeah, in any startup, it sounds great. Everything sounds great on the surface. But, if it's validated with proof of success, that a certain person or certain type of person can be successful. It's a benchmark for good salespeople, right? That's what they're looking for.

Brendon Cassidy:

They're going to be really hard to get a really good salesperson to come in with no proof. Like, "Hey, can I talk to a salesperson and ask how much they may you know, how much they've closed, how much they make?" And you're like, "We don't really have any ones. We don't really have anyone that's done that." They're not common. So, yeah, the best people are more risk averse than ever. I would say that's a thing.

Jason Lemkin:

Yeah, maybe that's the metapoint. I was initially teased on inflation and maybe higher OT expectations for the same attainment. But, the meta issues with so many SaaS startups are successful, the best folks are more risk averse in many cases, right? Or they're just, they're delaying, I think 10 million is the new 1 million in terms of risk for many folks, isn't it?

Brendon Cassidy:

Yup, for sure. And, there's a lot of people doing now what I was doing like four years ago. Maybe, five years ago, which was like, you can have a part time or advisory or consulting role with a lot of different companies. And first off, do really well and not have a lot of risks, professional risk in that. A lot of people are doing that, I know.

Brendon Cassidy:

Hopefully, I don't want to be, "Hey, Brendon start..." I don't know that I started that trend, but there's a lot of people doing it. There's a lot less, I'd say a lot more people who are less experienced that you can say, "Hey, huh." Usually, it's somebody that had some big exit or win or multiple wins, or whatever it is. But, brand is currency.

Brendon Cassidy:

And, there's a lot of people that have created really strong brands as like, thought leaders. But, yeah, so those people... There's a lot of opportunity for those people. They're super risk averse. And if they were to ask me, should I be risk averse? I'd say, "Yeah, you should." Generally, right?

Jason Lemkin:

That's interesting, related topic. You're right, there's a much larger pool of interim or consulting VPs of Sales and others. Marketers too, then there were just a few years ago, right?

Brendon Cassidy:

Yup.

Jason Lemkin:

Folks that would like to help two or three startups at a time, probably make 50% more cash than they would with a third of the stress, right? When does that work? And when do you need to graduate beyond that? When should you make that trade off when you don't have that hire?

Brendon Cassidy:

Yeah, it depends on what kind of impact you want. Do you want someone like me to help in certain area? Hey, if you could help us in this area, and you know that getting help in that area would be super creative to the company. But, then if you want true bottomline impact, I think it's like some sort of interim come in for six months or 12 months. But, you're either fully committed or almost fully committed to the cause. So, there's some skin in the game there. I think that could work, personally.

Jason Lemkin:

Yup.

Jason Lemkin:

And whoever it is, that's risk averse, can have two feet in, but it looks like they have one foot in. So, they preserve whatever the optics are that they want. But, that's like a more committed role, "Hey, you're here four days a week or five days a week. And we want everything you can bring to the table for the time that you're here." I think that can work.

Jason Lemkin:

And I would... If you could get a great person and then say, "Can you give us a year? Give us a year of the absolute best you have." I would do it, if that was the terms of that being possible, I would do it versus saying let's not do it, let's pass on this. And let's go out and look for that person, but somebody that's willing to put two feet in, in reality and optically.

Jason Lemkin:

And then, the problem is, I've viewed these sales leadership roles or like listing a house on the market. The longer it's on the market, the more the harder gets to fill it because there's more community within the sales leadership community than ever, right?

Brendon Cassidy:

Yeah.

Jason Lemkin:

I've been a huge proponent of it, for that you have things like, revenue collective/pavilion, that kind of stuff. But like, there's more... We help each other more, and we reference stuff off each other more. And so, it's like, "Huh, why is this job been on the market for a 120 days," right? And then, people talk, and then they're like, "Oh, yeah, I talked to them, for whatever reason, I didn't take the job." And then, even if they say good things, you're still like, "Ah, she passed on it, I don't know." It has that real estate kind of parallel. It's a good market, why it's been on the market, why is this house put on the market for 150 days? What's wrong? And there's that element of it, and I think that's... How do you deal with that? I'm not totally sure. But, I have ideas on how to deal with it. But, maybe...

Brendon Cassidy:

It's a good point that is an issue. And there's a related one of being the third or fourth VP of Sales that were there. But, in today's world, there's much more transparency around this and much more sensitivity, right? And maybe, that is a good point. If it's going to take you six months to hire a VP of Sales, maybe don't have it hanging out there for six months, right?

Jason Lemkin:

Yeah, I would...

Brendon Cassidy:

When you have an interim person can actually help because they can manage it, so that it is not a stale listing. If I were a founder, which I am now, by the way. So, everything I say is advice to founders, really advice to myself, but if I were a founder looking for a VP of Sales right now, I would be... And I didn't have a big network of sales leaders that I knew, or whatever.

Brendon Cassidy:

Whatever the terms of the scenario are, I would be meeting with people in a sort of unofficial way. I would love to learn about your thoughts on what type of person we should hire. And you build this almost like a council of people that you're talking to, and that's what I would do. And you've always been a proponent of that. But, you can't do it and say, "Hey, I'm looking for a VP of Sales, can we talk today?" You can have the conversation, but now, you just started the clock ticking.

Jason Lemkin:

Yeah.

Brendon Cassidy:

Versus when you're doing that in official way and you're building relationships. There's no immediate transaction to the app. And, I think we'd all be better if we did more things that didn't have an immediate transaction from one place to another in everything we did, generally. Oops, sorry.

Jason Lemkin:

I also see... Do you think, maybe, detailed point. But, let's talk for a couple of minutes about VP of Sales, and let's talk about selling. But, I see a lot of folks with a bigger market, I see a lot of responses for candidates are all take that potential position under advisement. What I mean is, folks are looking at more and more positions over more and more time. And I don't think this is bad, whether in reality or in their minds, they have more and more leverage over the startups, right?

Jason Lemkin:

Sometimes, I think this is delusional with some folks I know. Sometimes, I think it's reality. Do you think if a VP of Sales or similar doesn't fall in love with the opportunity, can you convince them over time? Or should you move on from these folks that are meeting with a 100 opportunities?

Brendon Cassidy:

Yeah, I think if you've built a relationship with that person, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

Where it's appropriate that you can continue to still check in and touch base with them. I mean, you... So, when I was like, when we were talking about EchoSign, you were sending the emails, forwarding the emails, this is before I decided to do it, even though I was... I wanted to do it, anyways. But, you would forward these emails about like, "Hey, here's a lead that came in today, or here's a deal we closed today." That kind of stuff, right? Where you weren't like selling it, we're just forwarding an email. And that's proof, right?

Brendon Cassidy:

You want to get a great VP of Sales, you're going to have to somehow take as much as the perceived risk off the table somehow while understanding that there's risk, period, for whoever that person is taking that job, but that kind of stuffs, it's about super validating, and a lot of founders don't do it, right?

Jason Lemkin:

Yup.

Brendon Cassidy:

They don't. So, you're having a sort of an unofficial conversation with somebody, maybe you're not explicitly recruiting them to be your VP of Sales. But, that's an opportunity for you to... Maybe, they're advising you on whatever the capacity is, but where you're giving them more proof points that this is a real thing with real opportunity and success. And then, and that can take a long time. But, I would do it.

Brendon Cassidy:

And that's a general, I think, rule of thumb is you should do more things that are... You can't always play the short game, in everything we do. And I think that's... It's really hard to view the world that way. But, there should be a lot of things you're doing that are strategic that you know will not produce some outcome immediately, and/or even in a week, or maybe even in a month, or whatever.

Brendon Cassidy:

There should be a lot of things you're doing around that stuff as a founder. I'm learning all that stuff, by the way. I'm learning a lot of things. The first time founder, co-founder that... Yeah, it's been an awesome experience. And, yeah, certainly, makes me respect the founder experience even more than I did, quite frankly.

Jason Lemkin:

So, let's get to that, just next is just one of the things I want to... Let's wrap up this part of the convo. But, before we started, you and I had a really interesting conversation about a tough topic, which is being topped. And one of the toughest scenarios, both for an executive and this founders are when you have someone on your team, and it's clear, you need someone above them. You have a VP of Sales, you need a CRO, you need a CMO, we can talk about sales in particular. And you had an interesting insight about how that's changed. And maybe, what's your general advice on handling phase transitions as you scale?

Brendon Cassidy:

I mean, yeah. I mean, there's obviously there's different scenarios of when and why you're talking to somebody. Sometimes, it's because you guys have done incredibly well. It's like, we want to go to the next step. And we want to go public, and we just think having somebody with more experience there, we'll help us in those areas. But, we don't want to really change almost anything, we're doing kind of day-to-day.

Brendon Cassidy:

And I think in those scenarios, it's super important to keep the people there that did it, built it, and happy. So, I'll use an example. So, when the CRO for Gong went there, he came in, he'd been on LinkedIn. And he's like, "What one piece of advice would you give me?" I said, "Just make Jameson happy," right? That's a piece of advice. I mean, he's got this incredible team. They're incredibly loyal to him. And like, just make him feel good, set up for success, and all the rest because there's not... It's working really well, right?

Jason Lemkin:

Yes.

Brendon Cassidy:

And so, you look at Akeem, they're all there. They're all there all the people that built it, the sales over there. And so, I give that Ryan, who is the CRO, I give a lot of credit. I would look at Outreach as another example, right? So, it's all well and good to say, I see trends in the market. But, it's really happening. You look at Mark the VP of Sales for Outreach. He was there from almost day one, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

And so, you keep that account in that culture, as long as they're motivated, and all that kind of stuff. And it's important, and I think if you look at you look at the alternative scenario, it's usually worse, right?

Jason Lemkin:

It's almost always work. If they've done well, and they leave, it's almost always worse, right? Almost always.

Brendon Cassidy:

Yeah, if they've done well, and you bring somebody in and they come in, and they're like, "Yeah, I'm coming in here to basically tell this person that I'm better than he or she is, and that I can get better people in here than he or she did." Yeah, then that's over, right? And by the way, they can't write the amount of like, sweat equity and intellectual capital that's been built there with that team, it is not replaceable, most of the time.

Jason Lemkin:

Yup.

Brendon Cassidy:

And so, yeah, that that would be one learning. I don't know that there's a massive sample size to support it. But, I think it's real.

Jason Lemkin:

And when and how do you have that conversation with your VPs of sales and others? Is it a regular check in? Do you spring it on them? That one, that spring it on them, I think is always is suboptimal than having had a check in, right? But, folks react to it. They have emotional reactions in many cases, too, right?

Brendon Cassidy:

Yeah, I mean, I think if you're a founder or CEO that has some experience, because if you have no experience, it's probably going to be hard to know unless you have some really smart people around you with a lot of experience on how to handle it.

Jason Lemkin:

Yes.

Brendon Cassidy:

But, yeah, the earlier the better. I feel like, you can say, "Hey, I love everything you're doing. And I feel like, we're on this great track to get to 20 million. And I feel like beyond that, here are the things that I think are things we need to..." Right? These are things that I don't think you can do. There are things I want to know that you can do. But, I think these are some of the areas that we want to be prepared for $20 million that indicate that all of us can take the next step.

Jason Lemkin:

Yes.

Brendon Cassidy:

That's how the folks should.

Jason Lemkin:

Got it.

Brendon Cassidy:

And so, they're aware. And then, when you get to this point, it's not like, oh, by the way, I need to hire a 100 person field sales team or I need you to hire somebody to run your up or whatever it is. And they're like, "Oh, I don't really know anyone can do that." So, yeah, preparation for that I think is good.

Brendon Cassidy:

And then, if you get there, and you've been, and then it's like, okay, clearly, I don't think this person can handle all the things that we need to do now for the next whatever, then you do it, and then it doesn't come as a shock. That person I think they're more likely to stay. And it's almost never done that way.

Jason Lemkin:

It isn't. It's almost always mishandled in some level, right?

Brendon Cassidy:

Yeah.

Jason Lemkin:

Yeah, and do you think... One last question on this, and let's talk about sales tools and sales vendors. But, do you think flat bookings is the clear sign you've waited too long to add a more senior person in the position? Is flat bookings for a quarter to the sign or is that not a sign?

Brendon Cassidy:

I think there's things that are ahead of that that would result in that, which is, I mean, obviously, you have to look at like, can we scale demand as a company to support the growth?

Jason Lemkin:

Yup.

Brendon Cassidy:

And, can we get more revenue out of our existing customers? So, there are other factors there. But, you should have... If there's an issue there, any one of those areas, you should have visibility pretty quickly, and at least perceived solutions to those problems, before they... At the board meetings kind of thing.

Jason Lemkin:

Yeah.

Brendon Cassidy:

Yeah. So...

Jason Lemkin:

Cool. Let's talk a little bit about tools, and what you've learned at CoSell in the market, but at a high level. Now, that we're in sort of SaaS sales 3.0, or some evolving new world, what parts of the good old fashioned sales toolkit aren't working as well, anymore? What's the cane in terms of its efficacy with so many vendors, and so many solutions?

Brendon Cassidy:

What's not working?

Jason Lemkin:

Yeah.

Brendon Cassidy:

I mean, I think, I don't think anything's not working enough to say you shouldn't do it anymore. But, definitely, I think there's been this massive shift in the last 10, 11 years from like... And this is important, because it used to be when you talked about how do we grow? How do we drive growth and opportunity that used to be, oh, well talk to the market, talk to the VP of Marketing. That's her problem, right?

Brendon Cassidy:

It's a very much a shared burden between marketing and sales. And so, you've seen this big shift from marketing end with the sales owns it almost entirely around like going outbound through outreach, and sales loft, and all that kind of stuff. In all these tools around optimizing that stuff, whether it's emails, calls, and all the rest that go into it, I think those... Personally, and I've seen this trend for a while, but... And that's part of why I'm doing CoSell, but like, those aren't working as well period.

Brendon Cassidy:

Trying to inundate the market with just this massive amount of quasi personalized communication, right? Everyone's wise to it now. And you just can't mass produce that, and have success. In my opinion, to expect to succeed all the way to the finish line on the backs of that are not... It's not enough. That's my opinion.

Jason Lemkin:

Got it.

Brendon Cassidy:

And that's why I'm doing this. It's just the whole thing. That co-submissive is, we just want to make it easy for people to get referrals and warm introductions from people that can help and are willing to help them, of which we have people like that around us period.

Brendon Cassidy:

And so, it's low hanging fruit that we just choose not to pick. And that's not a good equation for success. And I think that's in our conversations that we've had, by the way, this is not an enough for CoSell, but that's what every VP of Sales I talk to, complete, there's no argument. There's certainly an argument about how do you do it? Or a discussion around how do you do it? Or how do you do it most optimally? But, it's like, what's the problem? There's no argument. It's a 100% consensus, that the brute-force growth model is not going to ring the bell with 12th round.

Jason Lemkin:

Yup. So, let's step back because let's spend our last couple minutes on that. I liked your insight because I tend to be a little binary. But, it's worse. And I think your point is that the efficacy of some of this pseudo personalized playbook is decaying. But, that doesn't mean don't do it. It just means...

Brendon Cassidy:

No, you should do it.

Jason Lemkin:

... you got to do it, it just means you can't count on it the way you could have a couple of years ago, right?

Brendon Cassidy:

Yeah.

Jason Lemkin:

So, I think that's an interesting insight. You should be running... You got to run all these playbooks, you just have to add to the playbooks because their efficacy is decaying, right?

Brendon Cassidy:

Yeah. There's three areas. I look at it look like they're all in parallel, really. But, you have marketing, you have the marketing demand era. You can't just do that. Now, you need to do outbound or brute-force. Our belief is and that will be proven right or wrong over time is that referral selling is the last. Referrals and introductions, is the last untapped channel there.

Brendon Cassidy:

And so, that's our belief. But, yeah, I mean, it's certainly, been the last five or six years. You know what? One thing I was saying to somebody the other day that they completely disagreed with me on, by the way, and actually took personal. Took it personally and got upset at me about it.

Jason Lemkin:

Yeah.

Brendon Cassidy:

Which only validated, I was right more. But, there's less dependence on salesforce, which is not, this is not a slide at salesforce, first of all, but companies in the sales cloud are less dependent on salesforce to than ever, maybe. To create categories and many brands, and customer success and acquisition.

Jason Lemkin:

Yeah.

Brendon Cassidy:

I don't know exactly what the answer. The why of that is, but that's a... You go back 10 years, right? You remember?

Jason Lemkin:

When the world changed, if you look at revenue or market cap, salesforce has grown incredibly, right?

Brendon Cassidy:

Yup.

Jason Lemkin:

To almost $200 billion, but its share of total revenue.

Brendon Cassidy:

Yup.

Jason Lemkin:

And total market cap is half of what it was five years ago, because the rest of cloud got so big, right? So, salesforce has been shrunk.

Brendon Cassidy:

We have never heard it described that way.

Jason Lemkin:

Yeah, it's just the rest got so much bigger that you can make... You can attach to Shopify, you can attach to other ecosystems. And then, back when things were smaller, that was it. That was the only game in town, right?

Brendon Cassidy:

Yup.

Jason Lemkin:

So, salesforce is still great.

Brendon Cassidy:

And salesforce is also focused. They're focused on the marketing cloud and service cloud and other things, right?

Jason Lemkin:

Yeah. I mean, and sales, what are their smaller clouds now?

Brendon Cassidy:

I know.

Jason Lemkin:

Even service cloud is much bigger.

Brendon Cassidy:

And that's probably a pretty good explanation for it. But...

Jason Lemkin:

Yeah.

Brendon Cassidy:

... that's also, that's an opportunity there, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

I think... But, yeah, that's...

Jason Lemkin:

But, let's go back... Before we run out of time, let's go back, you've made some interesting points. And so, we have in terms of the evolution of what sales has to do to hit the number. Then, we go from demand gen to getting better and better at traditional outbound, but it's still cold. Outbound is still cold.

Brendon Cassidy:

Yup.

Jason Lemkin:

So, something that's interesting about CoSell and other solutions, is you're turning cold into warmish? Because a referral is a warm intro, right?

Brendon Cassidy:

Yup.

Jason Lemkin:

And that is profound that... And their ABM is some weird term that has gone out of fashion, but I still think ABM is better outbound, right? To me, ABM is actually writing one email, not writing that goes to one person that you've researched, rather than rinse wash and repeat, and you still need to do that playbook, but ABM has also decaying a bit, right? Because it's not warm.

Brendon Cassidy:

I think it's...

Jason Lemkin:

And warm is interesting, because warm is powerful, right?

Brendon Cassidy:

I think the intention of ABM was all cracked, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

But, I think it's like, on some level there's a required behavioral change, that not everything is about like, how do I load up a crap load of data, and click send and just expect it to do the heavy lifting for me? Which is like, that's the fantasy of a lot of these products, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

That you can just, oh, you don't even need to do it yourself. You just load it up. It'll do it for you. And I've always believed like, even a cold email, if I send a cold email to somebody in my career, that's the amount of research I put into it. The amount of time I spent thinking about what my approach or the angle is, is there's a lot of time spent on that.

Jason Lemkin:

Yeah.

Brendon Cassidy:

And what's the angle so that, if we're going to do this, that it gives us the absolute best chance to result in something. So, we're at an era where you need to start thinking that way. It's like, what is the most strategic way that I can engage with the customer? Not just what is the easiest mass produced way that I can try to interact with customers.

Brendon Cassidy:

And so, we were at that, we're right there. We're on this, on the frontlines of that discussion. And so, it's a needed behavioral change. There's generally pretty good consensus around that. And I think, in my experience, the most meaningful products that I've worked with or sold, there was a pretty... There was a behavioral change component to it, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

It's not just, "Hey, we do X just 3% better than Y." Anyways, yeah.

Jason Lemkin:

And so, just briefly, one more last thing, and then we'll break. But, so how does CoSell help create that warm referral? That outbound plus, plus? How does it work in practice?

Brendon Cassidy:

Yeah, so we're not... We've definitely evolved a bit from day one. I would say, day one we were like, more cross beamish, which, by the way, I think cross beam is cool product. That's not what we do. And so, there's still some people out there that think we do what they do, and we don't. But, we allow companies to basically create private referral networks, where they can essentially invite anybody into their network that they can connect with the sell through.

Brendon Cassidy:

So, that could be an investor, advisor, influencer, anybody that has a network that has some vested interest in your success, or some incentive to participate, you can connect with them and bring them into your CoSell network. And so, we've made it, which doesn't maybe some as easy... It's actually pretty easy to do.

Brendon Cassidy:

So, for instance, Outreach as a customer, Gong as a customer, Highspot as a customer, these are all early customers. And, the vision is, hey, let's imagine Outreach was an A round company today. What would be the most strategic go to market path they could take? Would be who's around us that has... We have our investors, we have our advisors, we have all the people that have some vested interest in our success.

Brendon Cassidy:

We can bring them in and connect with them, and then find out who we want to sell to intersect with... And we've made it and done in the way in which our customers own that network, and it gets bigger and better over time. And, it's our belief that this is going to be table stakes in 12 to 18 months.

Jason Lemkin:

Yup. And who's using it? Is it the VP of Sales? Is it sales op? Is it individual AEs?

Brendon Cassidy:

Strategic. Yeah, so, it's really driven. So far, there's a lot of learning, by the way for us to still a combat. VP of Sales drives it, in some cases, the VP of Sales is driving introductions.

Jason Lemkin:

Yeah.

Brendon Cassidy:

Other cases, it's like our VPS. So, like, Gong is going to have all their RVP equivalence, kind of, sort of driving it. And really, in a way, it's like, how can our sales organization help carry some of the load, right? At least within strategic and subsequent, potential customers for us? Is this just a way for them to do that, right? And that, by the way, is another behavioral change that's probably required.

Brendon Cassidy:

Where you can't just say, "Hey, SDR team, you own a 100% of the demand gen burden." I think that's part of the problem. And so, yeah, but yeah, with us, any company that wants to referral sell, they can just start inviting their... Anyone, investors, advisors, anyone to join their network, and then they can see, "Hey, like, Jason knows the VP of Sales at Adobe, or whatever it is.

Brendon Cassidy:

And we do it in a way in which... So, we have these two profiles, sellers with CoSell, which is not the best, in my opinion, the best verbiage around that. But, sellers, our customer's cosellers are... Whomever sort of refer the gatekeeper is to that relationship. And, yeah, like Darren's going to roll it out with all their investors, all of their advisors. And that's powerful, right?

Jason Lemkin:

Powerful.

Brendon Cassidy:

[inaudible], and there's a lot.

Jason Lemkin:

Yup.

Brendon Cassidy:

And that's it, either take [inaudible]. And that's what we believe, is that there's all this low hanging fruit around us, then no people that are of strategic value for us that we don't even... We just ignore, and we go, and we do more difficult and lower ROI things. And we just... That's the vision that we have, just making it easier to be much more strategic now and go to market, and don't stop.

Jason Lemkin:

That's great. Yeah, I think we have to keep adding smarter and smarter strategies as these classic ones just decline in the FSC.

Brendon Cassidy:

We should, you should.

Jason Lemkin:

We've got to leverage it, right?

Brendon Cassidy:

Our customers are like, "So, we shouldn't lose SalesLoft?" We're like, "No, use absolutely use SalesLoft, don't just use SalesLoft," right? Or Outreach. That's not good enough, right?

Jason Lemkin:

Yeah. We just got to add to it to hit the number.

Brendon Cassidy:

Anybody five years ago, like Outreach was probably saying, "Don't just do marketing," right? You got to do more than that.

Jason Lemkin:

Yup.

Brendon Cassidy:

I think with that point now, where it's like, it has to happen. There's no... Even like SDR leaders, who you think would be like, "Oh, this is potentially, a threat to me." Even SDR leaders are like, the best STR leaders I know, or look at this, like, yeah, there's just no choice. We have to.

Jason Lemkin:

Yeah.

Brendon Cassidy:

And I'm one of the best STR leaders in the world. And I can see that everything's getting harder, and declining response rates, declining engagement. So, there's no... We don't have a choice. We have to go down this path. And so, that's what we believe.

Jason Lemkin:

Yeah, last, I want to wrap this up. That's good. I find it... Everyone, I think that... Everyone learn, we have to have an outbound team, right? That's table stakes for anyone but the tiniest vendors.

Brendon Cassidy:

We have to.

Jason Lemkin:

But, I also observed that the teams have to get better and better because the crappy playbook... And sometimes, it doesn't work at all. The STR leaders have to be really good. And I'm not an expert, to bring in those big deals to break through the noise, they need to be smarter and better than ever to break out in many cases.

Brendon Cassidy:

Yeah, if you... The reality is, in most startups as a VP of Sales, you're going to have to be super involved in SDR stuff, right?

Jason Lemkin:

Yeah, it doesn't work an autopilot.

Brendon Cassidy:

And hiring and training. And like, by the way, the number of VPs of Sales that actually want to be in the weeds on that stuff is like 0.0. It's sucks in the worst way, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

Because you're like, "Oh, great." This 23-year-old kid made a great call today to this person that rejected them, and then, God, I'm really not that close to revenue right now. It's just not where you want to be. And they certainly, there's some that are great at it, but... And so, people are like, "Oh, I'll just hire for a STR leader." No. There's like, it's that's brutal heart. It's a really, really hard hire. I was talking to this guy, Kevin Dorsey the other day, he was at a PatientPop was like...

Jason Lemkin:

Yeah.

Brendon Cassidy:

I would consider him one of the best STR leaders. Maybe, in the world. And he's just like, "Dude, it's so hard now." He's like, "It's really hard. It's never been harder." And so, yeah, but there's a small list of people that I that are on my list that I'd be like, "That's who I know, I can fire that kid. Go figure that thing out, and almost entirely." Because, yeah, nobody wants to spend a ton of their time on setting up Outreach or SalesLoft. And like, writing these like outbound SDR scripts and all this.

Brendon Cassidy:

That's not what... And that's why most... The best VPs of Sales, a lot... The first question they ask is, "how many leads do you have a month?" Right? Inbound leads?

Jason Lemkin:

Yeah.

Brendon Cassidy:

And when the answer is zero, they're like, cool. All right.

Jason Lemkin:

Next.

Brendon Cassidy:

Immediately, they [inaudible].

Jason Lemkin:

Maybe, that's an interesting point. We can wrap on, which is that... It's interesting that because it's harder because the mass campaign, the low, the nuts and bolts approach works, not as well, a VP of Sales has to be more involved, right?

Brendon Cassidy:

Yup.

Jason Lemkin:

And they don't want to, right? And I think it's a good reminder. One of the biggest flags I see when I meet VPs of Sales candidates, one flag is when they don't really have that experience, right? Because it's tough to get on the job. But, the bigger flag is when they say, they're going to go find a director of inside sales, right? A director of outbound, right? That's the answer to the issue, right?

Brendon Cassidy:

Yeah, when you see somebody that doesn't understand what the burden is, right?

Jason Lemkin:

Yeah.

Brendon Cassidy:

That's when it's like, okay, maybe not. Because if you don't understand, I have to go in, and we have to literally create from nothing. All this outbound demand and interest, they don't understand how hard that is, that's not a good sign. It indicates that they've never had that book, versus somebody that does understand how hard it is.

Brendon Cassidy:

And maybe, they're just like, I don't know that I want to put myself through that right now. I would rather talk to that person, because at least they understand how hard it is, just like with any good sales leader, and most of the best sales leaders I know, are pretty humble, quite frankly.

Brendon Cassidy:

They understand that it wasn't just about them, but that there's timing and luck and other elements involved that are real, in some cases. People ask me about LinkedIn all the time. And one of the things I say is, the team we had at EchoSign, was so much better. By the way, there are some great people on our team on LinkedIn, by the way, phenomenal people, they've had a great success.

Brendon Cassidy:

But overall, the team we had an EchoSign was way better. It was a way better team generally almost everywhere. But, we didn't have this self-serve, like opt in network, where people were just like, "Yeah, I'm going to put my profile here." And so, that team was better, and just the reality is LinkedIn was this network that was super viral, let's spend any money to build it, quite frankly.

Brendon Cassidy:

And that was the most enduring thing then and now. It virility of it, all that kind of stuff. But, that's luck, mostly, right? I think I did some good things there, by the way, but the level of difficulty, in other things I've done is much higher, quite frankly, right?

Jason Lemkin:

Yup.

Brendon Cassidy:

They're didn't relatively easy, because you had this data set, but we're just like, yeah, here's more. And you're like, oh, I don't have to convince you to come. No, no, we're just going to come. And we're going to keep that data fresh for about 20 years, is that okay?

Brendon Cassidy:

So, that's like, that's on the scale is easy. I mean, there were definitely some super, super tough, important decisions we made early that were right, I think. But, yeah, that's what I would say.

Jason Lemkin:

Got it.

Brendon Cassidy:

And Talkdesk in the early days. Talkdesk, there were some hard times there. When you were like, "Hey, the phone doesn't work." We're selling this call center solution, right? But the phone doesn't work. What do we do then? So, those were some challenging early days that obviously, got fixed. But, yeah, I think there's an element of luck and everything too, and timing and all the rest, right?

Jason Lemkin:

For sure.

Brendon Cassidy:

I realized that most of the best people don't understand that, that it's not just their greatness that they've got accomplished everything that's happened to them. So, yeah.

Jason Lemkin:

All right. Let's wrap it up with one more fun thing just to tie together some of these themes.

Brendon Cassidy:

Sure.

Jason Lemkin:

Beyond anything we've chatted about now, what are some of the things that the best sales teams do to beat the others in a competitive space? What are just a couple of things that they do that you're like, "Crap they want they won that deal again and again, but their product actually isn't better?" What are a couple quick insights that we can wrap that you see the best folks do that just the good or the mediocre don't do as well?

Brendon Cassidy:

I think the best sales orgs in competitive sign just have this just crystal clear black and white understanding of why should we win? One of the reasons that we should win and beat them in a deal and one of the reasons that they should beat us. And so, you know what their playbook is, you know what your playbook is, and then you understand that it's going to be... It's a battle for mindset, like certainly, that goes on. We said, "Hey, we know if the deals about this, we win. And we know if the deal is about these other 20 things that it could be about. We know that they work."

Brendon Cassidy:

So, we just said, "We're going to make this entirely about this." Everything that happens in the sales cycle will be centered around this narrative. And we will not be pushed off that market any point. And so, the other guys were like, "Hey, we have all this other stuff." And we're like, "None of it matters. The only thing that matter is this."

Brendon Cassidy:

And so, I think that's the... I think realizing what you're... Not just what your strengths are, but what your weaknesses are. And then, weaponizing that before your competitor exposes it as a liability, right? Taking too, why should we lose? Okay, if we know why we should lose and why they should plus, then we know that, okay, then we know that we need to make the narrative about this. And we need to minimize the impact of the other 20 things in everything that we do. And I think that works. Yeah, I mean, I think, yes.

Brendon Cassidy:

I was talking to a friend at Adobe the other day, I said, "I wonder would be like, if we all came back in, obviously DocuSign for like $60 billion now. Can we reframe the narrative?" Because that's really, that's what it is. It's like, if you know how your competition is attacking you, then that's... And so, I thought we did a good job of understanding. We know that this is how they're attacking us. We know that this is where our flank is exposed.

Brendon Cassidy:

And I think a lot most sales organizations don't understand that. They don't want to understand, I think, in some cases, right? But, sometimes, it's easier to sell. And not ignore what your weaknesses are or where your vulnerabilities are. And we call it flying blind, right? I think that's the best competitive sales organizations knew it inherently. They knew everything that their competition was going to do. And that was already baked into their playbook, right?

Jason Lemkin:

So, good, some are hidden.

Brendon Cassidy:

Yeah.

Jason Lemkin:

All right. Brandon, thanks so much for catching up. This was great.

Brendon Cassidy:

Yup.

Jason Lemkin:

Let's sell together with our partners and vendors at cosell.com, right?

Brendon Cassidy:

Yeah.

Jason Lemkin:

Let's add onto our toolkit, which we still need to do the old stuff, but it's just not working as well for you too.

Brendon Cassidy:

We got to do...

Jason Lemkin:

So, we got to add to it. We got to add up.

Brendon Cassidy:

We got to do the marketing too.

Jason Lemkin:

So, we got to do the demand gen. We got to do...

Brendon Cassidy:

We got to do it all.

Jason Lemkin:

Our goal in 2022 is we got to add a few layers. We got to add a few new systems and processes to reach the flooded, the fatigue markets, right? So...

Brendon Cassidy:

Yup.

Jason Lemkin:

Good insight, my friend. All right. We'll chat with you soon.

 

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