The Playbook to Hiring Your First VP of Sales and Not Screwing it Up…….with Cassidy Ventures Founder Brendon Cassidy (Video + Transcript)

Brendon introduces his playbook to hiring the first VP of Sales from his experiences as VP of Sales at LinkedIn, EchoSign, Talkdesk and more. Learn the dos and don’ts to make the correct hire the first time and not rush into hiring the wrong VP of Sales, which can cost the company months or even years.

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Brendon Cassidy | Founder @ Cassidy Ventures

FULL TRANSCRIPT BELOW

Hey everybody, how you doing? So the title of my presentation is The Playbook To Hiring Your First VP Of Sales And Not Screwing It Up. I do this literally every day with a wide range of clients, sort of helping them in and around hiring a VP of Sales, maybe replacing a VP of Sales. So this is kind of what I do. I’ll toggle sort of between the founder perspective of hiring a VP of Sales, as well as a first time or somebody that wants to become a first time VP of Sales.

A little bit about me. I was the 15th employee for LinkedIn and their first head of sales, joining the company back in late 2005 when everybody thought it was a spam company. Was the 10th employee and VP of Sales for EchoSign. So I worked for Jason Lemkin for about six years, half of which was EchoSign and the other half of which was Adobe post acquisition. So I wanted to get the experience of working for a Fortune 500 tech company. So I’ve got two and a half years of that and that’ll likely be the last of that. Fifth employee and VP of Sales for Talkdesk, which was recently evaluated at $2 billion. So I was their first employee in the United States. And so, I consult and advise for startups about 35 startups over the last three, three and a half years.

So talking about hiring your first VP of Sales is obviously everybody knows the stat about what percentage of startups fail. Anybody want to share that? What percentage of startups ultimately will not make it? Anyone? 90%. Roughly 90%. Roughly about eight out of ten first VP Sales hires for startups will also fail, right? And they will also sort of average 10 years, about 11 months. So if you get it wrong, the consequences are essentially you’re going to lose one year of your startup life. For most startups, that’s the difference between life or death. You don’t get to have a Mulligan on that year. Irregardless of that, the trajectory of your company is forever changed, right? So you look at companies, Top 10 SaaS companies in history, none of those companies got their first VP of Sales wrong. So the consequences are tangible.

If you’re a CEO and you want to pull the trigger. So if you got your first VP of Sales wrong and you want to pull the rip cord after three months, and that’s certainly something that I’ve advised. That’s something that Jason advises. But the reality is there’s political consequences either way. If you hold on to him too long, that’s a year of your life. If you pull the rip cord after three months, that’s a lot of capital with your investors you may not be able to get back. So it’s just not a scenario that you really want to find yourself in. And again, you lose confidence in your investors and your board and that’s a level of loss control early on. That’s not ideal for a founder.

Step 1: Find a Friend

So I wanted to just kind of put some sort of concrete simple steps together then I’m pretty sure are right. Doesn’t mean that it’s going to reduce your risk to zero. But if you can take a 80% chance of failure and reduce it to 20%, it’s about as good as you can hope for. So step one is find a friend. So oftentimes the founder or CEO sort of has two primary influences when they’re running this search. One is on the investor side, two is on the retainer, the executive search side. And the reality is is both of those parties have an agenda, right? Which is to get somebody in place and check that box as fast as possible. For you, there’s really no reason to rush here. Okay? I’m assuming you’re running a VP of Sales search because you’ve had some level of success and you want to double down on that or capitalize on that.

So for you, find somebody. So it could be anybody. You can come up to me after this and I can give you a list of 10 people, but find somebody that’s been a VP of Sales before successfully in a startup, scaled that to some level of success and make that person sort of an independent arbiter of that process. They don’t have an agenda. You’re probably going to maybe give them some shares in an advisor. You may pay them, but the reality is is there going to be somebody that’s going to be your safety net through the course of that search. Okay? So have an objective voice with experience. Without it, you’re likely to make a mistake.

Step 2: Define your ideal candidate.

So I have a process, sort of a checklist. Obviously, at the top of the list is somebody that’s been in a startup, been successful, scaled, maybe had one exit, maybe had more than one. That’s your ideal. That’s your ideal profile. Acceptable profile is someone that’s been a proven success building through your stage and is ready to go beyond. Less acceptable as somebody that’s been a number two. Sorry. Somebody that’s been a number two. So somebody that has been a right hand to a VP of Sales, has taken the company from zero to 50 or zero to 100. And then last resort is somebody out of a big company like Salesforce, Oracle, again for all the reasons that had been stated before, but those are people that, generally speaking, you’re not going to be comfortable walking to a scenario without any brand, without customers, without potentially even a pitch and a message. So I would avoid that at all costs generally.

Okay. One of the mistakes, I think two of the mistakes actually that I see a lot of founders make is they tend to aim high, too high or too low. So they come out and they say “It’s sort of manifest destiny that somebody that my magical dream candidate that scaled company X, Y or Z from zero to 50 or zero to 100 is going to come off the beach and stop whatever they’re doing, which is probably not much except golf and jump back in and take a risk to build your company. It’s not going to happen most of the time. Okay?

I can give you 20 people that I would identify as like here are your perfect first VP of Sales hires and you’re probably going to miss on all 20. And if you want to land one, it’s going to take a long time. You can’t just start today, right? So a lot of times this is a very, very long game. The best recruiters that ended up with getting the best VPs of Sales do it over six months, a year, sometimes more than that. And again, unless you have time, it’s probably not going to work. Okay?

Step 3: Aim high, aim low, aim in the middle. But you should be talking to all those levels in parallel.

So the odds of landing your dream candidate are low. Identify sort of the next level down, but you should shoot high. Right? So when you talk about whether that’s Jim Eberle from Box, Matt Cooley from Quip, a lot of these people are probably unrecruitable, but you should meet them. Right? And you should prepare for a long process potentially to make this hire. I would say don’t make the hire then make the wrong hire. So if you need to wait longer, if you need to prepare your board for a longer process, don’t just check the box because the board told you to. Don’t just check the box because the retained search firm wants to get the second half of their payment. You take as long as you need. And in my opinion, no hire is better than the wrong hire. Okay? So aim high, aim low, aim in the middle. But you should be talking to all those levels in parallel.

Step 4: Who is coming with them?

Step four and this is really for me, this is kind of a mandatory deal. Who’s coming with them? So one of the first VPs of Sales I had in my career had this incredible resume. Well, at that time, thought that was an incredible resume. But Siebel, Oracle, all these companies. Nice guy, loved to drink Maker’s Mark, super social, all that stuff. And I noticed that every time we were looking to build the team or hire people, he was always asking me “Hey, you know anybody we can hire?” And that was at that point, you know, 26. I didn’t really have much of a network at that point. And I kept coming back to the point of like “Why does nobody want to work for you? Right? You’ve been doing this for like 20 years. You worked in all these companies and yet not a single person that ever worked for you in the past wants to come with you.”

And there was a reason why, right? Because he was somebody that managed and led teams sort of with a me first attitude, right? He was looking to raise and shine his own star over his team. So who’s coming with them is a huge factor for me. You’re not just vetting the candidate, but you’re also vetting the people that they would potentially bring with them. If they’re not comfortable sharing that. And again, there’s certain rules and ethics involved here. If somebody’s going to give you the names of four or five people they want to recruit, but then you’re not going to hire them, but then you’re going to go recruit their people even after you’ve turned them down. I don’t really consider that to be a super ethical process.

So if anybody does that, then I would say “Hey, you got burned. Maybe you don’t do it again.” But for me, I’m not going to violate that principle. So who they’re going to bring with them is critical, that them ideally even like interview them sort of in the process in parallel with the candidate because for me, for a first time VP of Sales, so say you’re … I don’t want to say any … I don’t know. What is a good age for a first time VP of Sales these days? 28, 30?

I would hire somebody younger, less experienced, but they had four or five great people they could bring with them. I’d be willing to take that risk over maybe somebody much work experience that had nobody they could bring with them. So that’s how big a factor it is. I’ve sort of been advocating for this for awhile and I see more and more founders and CEOs that are adopting this as a standard part of their process. Okay?

Why does it matter that they’re bringing their own people with them? Well, because it’s an advantage for you. These are foundational hires. These are people that are going to help set the culture and set the values for a VP of Sales. And again, you’re looking to make as many low drama hires as you can as VP of Sales walking into a startup. People that can come in and contribute immediately. People that can, not just from a numbers standpoint, but from a culture and mentoring standpoint. So if you don’t have any of those people, you’re immediately on a level playing field with everybody else. Right? You’re recruiting on the merits of whatever your company does, whatever the pitch or whatever the buzz is. It’s tough to stand out in the recruiting process there. And the quality of the people you hire will probably be reflective of that.

Step 5: Don’t Panic.

Talked about before, don’t panic. I used to be a proponent of make the hire. Make the hire, give it three months. If it doesn’t work, pull the rip cord. We talked a little bit about that earlier, right? And talking about the political capital you lose as a founder. So I’ve become a bigger believer in hey, like assuming you’re doing something well and doing something right, you have somebody that’s managing or leading your team, maybe you stick with that for awhile instead of making the wrong hire. And quite frankly, most of the time when a startup hires a VP of Sales that’s the wrong hire, everybody knows. Right? Everybody knows, all the employees know, all the salespeople know, potentially even the board knows, but hey, check that box.

So do nothing. Maybe you have somebody in there, maybe you can promote from within, right? Maybe you have somebody, a manager that could be a director, a director that could be a head of. Or maybe even a head of that could be a VP of Sales, but make the absolute right hire. And if you don’t have the right person, if you have doubts and there’s doubts within the team on that decision, just don’t do it. Okay?

So I guess that’s the main portion of the slide piece. I’m happy to open the floor to any questions anyone has on the hiring process or anyone that wants to be a VP of Sales. Anybody who wants an introduction of people that can help you or help advise you in your search. Yeah, go ahead.

QUESTION 1: What are some of the most important characteristics that goes beyond experience?

I would say you got to have a fighter on some level. Right? The odds are so stacked against you, it’s not just that you’re a fighter is that you’d like to fight because there are going to be ups and downs, but there’s going to be downs so low. I’ve been through them myself where you go home and you’re like we should just close the company tomorrow. Right? We’re done. It is game over. And then you go home and it’s like … This is something I’ve had in throughout my career. I don’t know why. It’s like this like hey you tend to your wounds for a few hours. And then the next morning you wake up and you’re thinking about solutions. How do I fix this? How did we flip the script? How do we change things in our favor? And that’s what it takes, I think. You know, and I’m not done with that answer.

Got to be a fighter. You have to be just a relentless recruiter. So recruiting all the time, recruiting even when you’re not working, quite frankly, when you don’t have a job. My first job out of college was a recruiter and so, that’s just like the ultimate sort of you’re always thinking about relationship building. And you should be recruiting for your career. Right? So you should be like hey, I haven’t had a full time job in a couple of years. Right? I already know the team. If I were going to take a full time job somewhere, I know exactly who I’m taking with me. And that’s what you need to be doing because it’s just relentless on that front. And that’s not just recruiting, it’s building your brand and establishing your brand and your company’s brand.

I think you have to have no taste for politics. There’s no place for politics and bureaucracy. It’s like a pathological meritocracy, you know? It’s like I don’t care what you did before. I don’t give a shit. Right? You may have been at Salesforce in ’99. You may have been at Box in 2006 or LinkedIn in 2008. I don’t care. Like it’s what can you do here today now for our company. And if you perform and you put the effort in and you show the values, the company values, then you’re moving up or whatever it is that you want to do. And yeah. Does that answer your question? Okay. All right, go ahead.

QUESTION 2: What characteristics of a company are you’re looking for as a VP of Sales?

Yeah. Yeah, I’ve blogged about this one a few times, so. I can’t even remember my own shit that I wrote sometimes. But you know, I want … Sorry. Yep. Question is what characteristics of a company are you’re looking for as a VP of Sales? I think that’s right? To evaluate, yeah. I would say find something interesting. Right? Personally interesting that you’re like hey, that’s interesting to me. If it’s totally uninteresting, I don’t know how you could do it for four years or five years. I can’t. If it’s uninteresting, I’m just, you know? Who gives a shit, you know? Like that’s been done 20 times, you know? So something interesting, something ambitious.

A founder that you truly like and truly respect is critical. I would say that’s number one for me personally, which means I may never work full time again, but finding a founder that you want to go invest four to five years of your life with and for because it really is. Certainly there’s other leaders and executives that come in, but if the VP of Sales and the founder CEO aren’t all on the same page, it’s not a good thing. From a like revenue growth in the early stage series A, like if you have a one to one sort of ARR to funding ratio, that’s great. You know?

When I joined Talkdesk, I think it was like three and a half, 4 million to like 2 million. That’s a really solid ratio early. Obviously the more money you raise, the more of that ratio comes beyond one-to-one. But those are early good factors because the more money you raise and the lower your ARR is, the further behind the eight ball you are as a startup. And you’re constantly trying to make it up. And I’ve seen VP of Sales get swallowed up in like a founder zone lust to raise money on no revenue. It’s not a good position to be in. Right? You want to have some solid fundamentals there.

Can you recruit the team to that company? Right? And that’s all another good indicator of the people you know, the people that you’re connected to that want to work for you or work with you. Can you bring them? Are they interested? If they’re not interested, it’s a little bit of a concern.

QUESTION 3: co-located VP of Sales. So I’m assuming startup in San Francisco with a VP of Sales in Salt Lake?

First question was a co-located VP of Sales. So I’m assuming startup in San Francisco with a VP of Sales in Salt Lake? That type of deal? Depends on what do you want to do in Salt Lake? Do you have plans for Salt Lake City like beyond or at some certain types of scale? Certainly, I think you see most scaling companies doing something outside the Bay Area, right? Utah, Phoenix that Robbie Allen over here has made famous as a hotbed of startup activity. Phoenix, Austin, you know. LA, I guess. I don’t know. Is LA a hub or is LA kind of like a, you know? I’m not sure what LA is yet.

Yeah, I would say you can do it, but I would say more in a scenario in which you’re doing pretty enterprisey up market scenarios where you want your VP of Sales flying to your clients. For an inside sales model, it’s obviously a total non fit. Right? Unless you’re going to do something in that regional market at some point. What was the other question?

QUESTION 4: Comp range in OTE as a function of your current revenue.

I mean, you’re going to pay through the nose regardless for a good candidate. So I’m not sure there is any one rule around that. Let me think about that one. I’ll get back to you. Go ahead.

QUESTION 5: How do you know when to … You know, the challenge of topping an existing early employee that’s in a sales function of sorts versus just promoting that early employee? In your opinion, when is the right time to just promote that early employee into the VP of Sales versus topping them with an outside hire?

Well, obviously it depends on how successful that internal person is. So they have to have you on some sort of trajectory that you want to be on. I don’t think there’s any doubt about that. They have to proven that they can recruit and train and hire and onboard people. I mean, I’m a big believer of promote from within, but typically a VP of Sales promoting sort of next level people. I do think some companies definitely will top people too early. I think that’s an epidemic, quite frankly. If you have a VP of Sales that took you from one to 15 million in 18 months, it’s pretty good, right? Or even 24 months, or even 36 months for that matter. And so, I think they should be given the opportunity to take you from one to 20 and then from 20 to 50 or 20 to 40.

And too often VP of Sales often heavily influenced by the board yet. That’s great. We got our one to 20 guy. Let’s go get our 20 to 50 gal. And I think it’s a mistake. I think a lot of times it does more damage than good. I think most companies overcome it because they’re already at 20 million. You’re probably not going to be able to kill them. So I would say that’s a leadership failure for a lot of CEOs, right? Because CEOs just sort of want to outsource the issue instead of saying “Hey, like here are the things I’m tasking or challenging you to do. This is how you need to grow with the company. This is what I want to see over the next six to nine months.”

But they don’t know how to process it and communicate it. So they just say “Hey, let’s go get somebody bigger.” And the reality is is like unless a lot of the things that you’re still doing from one to 20, you’re still doing a lot of those things from 20 to 40. It’s a reality. You’re doing more of those things and you’re doing the things that the person who hired that’s only done 250 million plus are going to be tasked to do, so. I think I didn’t answer your question. Go ahead.

QUESTION 6: My company is a very technical product and somebody serious software and it’s a new category you were creating like scratch. And we’ve already made a mistake hiring first VP of Sales. Any thoughts given that scenario and what characteristics they’re looking for?

Yes. I don’t know if anybody heard that. He talked about how he’s selling a product in the engineering space or to engineering as a buyer. And already hired a VP of Sales, already fired a VP of Sales. What do I do now?

New category. Doesn’t exist.

Doesn’t exist. Got it. Okay. I would say what’s going well? Here, let’s put the mic up. Let’s have some back and forth.

Engagement with the lower level kind of end user people. We’re getting better at selling up in the market, but really what’s working well is my co-founder CEO leading the sale. And everyone else we’ve brought in as a sales leader has just flopped. And he’s very technical. He doesn’t come from business background, but he’s strategic, you know?

Yeah, I’ve seen this one.

Still in founder-led sales.

Seen him more than once. Yeah. So he’s the CTO?

CEO.

CEO.

Yeah.

And he’s a technical background you said?

Yep.

Okay. And no sales people currently performing in the company?

We have a couple that are okay, but not VP material.

No, no, no. But I mean from a like they’re closing deals, they’re scaling and ramping.

We have one besides CEO who can close deals.

Got it. Well, I mean, obviously I could say open up another VP of Sales search and get your second person. I mean, you’re going to have to do that obviously on some level. It’s not that uncommon for a CEO or a founder to stand in and serve a surrogate VP of Sales for some period of time. I don’t know is he a natural mentor and coach and all that kind of stuff? But I would take the reps you have and shadow him as much as possible, bottle as much of what he does and says and knows as you can. Maybe a product like Gong is a good product for that where you start recording and transcribing and analyzing all your sales calls. I think Gong is one of the best sales enablement products I’ve seen come out over the last five years in this space. But that’s what I would do is try and get those two reps you have on the level as much as possible, if they’re not. And then try and find … Where are you based?

Berkeley, across the bridge.

Maybe try and connect with some VPs of Sales that have maybe sold in like the engineering space that can sort of act as advisors, surrogates, helpers for you. It’s not free usually, but it’s worth it. And see if like maybe I can tap into who they know. Like I’m trying to think of maybe somebody that was like early selling, like GitHub or you know? So try and find a couple of VPs that have sold to the buyer, into the market that you’re trying to and sort of give them some stake in the company and they’ll help. And if they can’t help, I don’t know what the next step is. All right, go ahead.

QUESTION 7: Do you have any tips for CEOs? We’ve hired a VP of Sales recently. She’s performing really well, but with the characteristic of an effective VP of Sales comes a certain swagger, comes a certain hey, I’m closing deals so I can do whatever I want. You know, this sort of impact on the culture. Definitely different management style required there as opposed to the rest of the team.

So you’re saying that she doesn’t have the swagger you want?

She does.

Oh, she does.

That’s great for sales. It’s bad for culture.

Got it. Is she a legitimate like VP of Sales? Has been a VP of Sales before? All that kind of stuff.

Yeah.

Okay. At a successful company, I’m assuming?

Yeah.

Okay. I would tell them that’s not good for the culture. At a minimum, sit her down and say … I’m assuming your company is probably just as many engineers, if not more than salespeople.

Yeah, no. I mean we’ve, we’ve tried the coaching, but the push back we get is I’m closing deals, I’m making revenue happen, so I get a pass.

Generally, at some point you want your VP of Sales to be managing, building, coaching and not closing deals, which should significantly and maybe temper their ego a tiny bit. So I would say hopefully there’s people on the team working for her.

Yeah, that makes sense. So coach toward the leadership piece of it.

Yeah. I mean, it’s great that she can close deals, but obviously you hired her to build and run your sales organization, not be an enterprise AE, right? Yeah. Go ahead.

QUESTION 8: Thanks. So I know it’s a range based on stage of the company and experience of the salesperson, but can you give some ranges on total compensation expectations and kind of what the breakdown is between equity and base and commission or bonus?

Yeah. So what are the total comp ranges to expect to have to pay essentially? Okay. I would say, I mean, it’s loose, right? I mean, sometimes I hear of searches and you’re like oh, my god. Like that can’t be right. Right? But I would say somewhere between three and 500K in total comp. Equity. I mean, I can tell you the things that I would take a job for. But yeah, I would say it’s equity anywhere from 1% to 5% depending on the level of experience for the candidate. If you want to get I’ve been there, done that, multiple exits, reduce the risk as far as you can down the ladder type of hire, you’re going to pay a heavy price on equity. And you’re not going to get those people without it, period. So. Okay. Any other questions anyone has out there? Yep.

QUESTION 9: Comfortable with a new VP of Sales coming in and using an outside coach. So whether it’s Brendan or someone else, but talk to me about that dynamic. What should our expectations be and what should we budget for?

Yeah. Yeah, I mean, I think it’s a good thing. You know what I mean? VP of Sales can be a pretty lonely job, even for working for a great CEO and with other great leaders. The reality is they’ll be judged on performance and their number. And I think bringing somebody in as a coach or consultant or advisor can help eliminate mistakes as a sounding board, right? Because there’s so much creation happening in a startup. It’s constantly like creation, iteration, beta test, back to the lab. You’re doing it all the time.

So having somebody that can sort of help guide them in their decision making process, help tell them when they’re about to drive over a cliff, I think is a worthwhile investment. That could be paid in stock and equity. It could be paid in cash, could be paid in both, depending on how involved you want them with your company and with your VP of Sales. But I would totally recommend it and not just because that’s what I do for a living. I think that’s it, everybody. Thank you very much. Thanks.

Published on March 3, 2020

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