Why Your First VP of Sales Will Fail (And What To Do Instead) – Eyal Worthalter, Multi-Time VP of Sales, Cybersecurity Startups

Are you grappling with when, and who, to hire as your first sales leader in your cybersecurity startup? Wondering why sales leadership churn is so high, or if founders should keep selling longer? If you’ve debated hiring account executives versus a VP of Sales, and wrestled with investor pressure on scaling your sales team, this episode is for you.

In this conversation, we discuss: 

👉 The crucial distinction between sellers and sales leaders at different company stages
👉 Why timing, founder credibility, and expectations can make or break your first sales hire
👉 The importance of trust and alignment at the C-suite level for long-term go-to-market success

About our guest:
Eyal Worthalter, a multi-time cybersecurity sales leader, shares hard-won lessons from the frontline; including insights from his widely-read article on why most first VP of Sales hires fail. He’s contributed to Ross Haliliuk’s Venture In Security blog and works closely with founders and sales teams to help improve their approach to building go-to-market strategy.

Summary:
Listen in as Eyal Worthalter and Andrew Monaghan dig into the messy reality behind hiring the first sales leader, founder-led selling, investor pressure, and practical frameworks for scaling sales teams. If you want to avoid costly mistakes and build your sales org the right way, this episode will challenge your assumptions—don’t miss it!

Connect and Learn More:
Find Eyal Worthalter on LinkedIn. 

Ready to discuss your own sales challenges? Book time with Andrew Monaghan for a strategy session.

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Transcript

Andrew Monaghan:
There's a lot of advice out there about when a startup should hire its first sales leader, which is why I wanted Eyal Werthalter to join us on this episode. Eyal is a multi time sales leader at cyber startups and wrote an article titled why your first VP of sales hire will fail and what you can do instead. You know, in the article he gave really solid recommendations that I agreed with and we had a couple of areas where we didn't have exactly the same viewpoint. Either way, he clearly has the experience to be able to give great advice. So this is an important discussion. I'm Andrew Monaghan and this is the cybersecurity go to market podcast where we tackle the question, how can cybersecurity companies grow sales faster? Hey Al, welcome to the podcast.

Eyal Worthalter:
Thank you, thank you. Glad to be here.

Andrew Monaghan:
Yeah, you know, I've been looking forward to this for the two, three weeks that we've been going back and forward on it and talking about it. Interesting conversation that I think is going to happen from our discussion today. It is all based on an article that you wrote for Ross Haliluk's venture and security blog. I guess it is. And then it was reposted or posted on LinkedIn and it was titled why your first VP of Sales Hire will fail and what you can do instead. Provocative title.

Eyal Worthalter:
I have to. If you don't make it provocative, then people will not read it, especially when it's that long. Ross and I debated over the title and we settled on that one. But at the core, the idea is, you know, there's been a lot of mistakes hiring VPs of sales, both from, you know, founders, even, you know, sales leaders that going to jobs, thinking or having certain expectations and then find, you know, the reality very different. And even, you know, the VC ecosystem also adds pressure to that. And what I've seen in the last maybe two, three years is that the usual tenure of a VP of sales is just shortening and I hate that. And so I want to figure out how to help founders, how to help sales leaders navigate that. And a good way to do that is to create a little bit of drama around the title and maybe people will pay attention to it.

Andrew Monaghan:
Well, the point you make at the start is you talk about drama. I mean, gosh, we're talking about people's lives here though, right? I mean, who talking about people with families to consider their livelihood, to consider their careers, to consider making a bet, a change, a decision to go join a startup and lasting less than a year. That's Kind of crazy that happens.

Eyal Worthalter:
It is crazy. It's not only crazy, I wish it was the exception, but it is the norm right now. When it happened to me, I started thinking, you know, first, you know, you go into this sort of postmortem mode. Like, you know, what did I do wrong? Right? Where did I fail? What could I have done differently? Then I started talking to other people, right? Both, obviously, I was looking for a job, so, so, so I started networking, talking to my network, talking to my friends, my colleagues, former colleagues, a lot of headhunters, a lot of recruitment recruiters, multiple talent agencies. And then I start seeing like, hey, you know, this has happened time and time again. Like, I'm not the only one. Like, I talked to three different CROs in a week and they all told me essentially, hey, this just happened to me in the last two years and now I'm happy, but this happened and this is how I avoid it from happening again. And then I realized, okay, so I started taking some notes from those conversations.

Eyal Worthalter:
And then over time that, that became sort of like an idea of like, hey, how can I help others? And then Ross reached out and say, hey, you know, I like what you've, you've written. I, you know, I would like you to contribute. And then I told him, hey, I have this idea of, you know, sort of figuring out how to help founders choose the right VP of sales. So I'm not saying it's not anyone's particular fault like this happens. It's. It's a series of things that creates the revolving door of sales leaders. One, lack of knowing how to hire a VP of sales. Two, timing.

Eyal Worthalter:
That's one of the things I said in my article. Timing is very, very important. And three, misalignment on expectations. Many, many sales, even salespeople right now, but most especially founders, they expect a sales leader to generate demand for a product. And that's something I want to reiterate. That's the first thing I will say. Salespeople do not generate demand for a product. They convert demand into revenue.

Eyal Worthalter:
And that's what I want to drill into everyone's minds. And if I can do that, then I think I've given my contribution to the world. Small world of cyber.

Andrew Monaghan:
Well, you do talk about timing. And if I'm going to read, read from the article, you say if you are pre revenue or an early stage cyber company that is still testing out the water, so to speak, you don't need a salesperson and you definitely don't need a VP of sales. So Is that happening a lot where funders are going way too early to hire some sort of sales leader?

Eyal Worthalter:
Pre revenue 100%, forget about it. Even a sales leader, a seller, Right. If you've invoiced zero. Right. If you've sold nothing of your product to the market, how can you expect somebody else to do that for you? Realistically? Right. And I've had this conversation multiple times with founders even when I was looking for a role and even the last two or three months I've had founders telling me, hey, can you come help us out in some way? Can you come in as a fractional sales leader? Great. You know, what's your run rate right now? And they tell me zero. How can I do something for you as a founder if you haven't been able to do it yourself? And it's one, you know, and the one thing I tell them, the first thing I tell them is you as a founder will have a much higher win rate than me as a salesperson.

Eyal Worthalter:
Even if I were, you know, the best salesperson in the world. Right. Even if I add an award for the bestseller, your conversion rate as a founder is always going to be at least double, if not more than mine.

Andrew Monaghan:
Why is that then?

Eyal Worthalter:
It's a matter of credibility, right? Like the founder has skin in the game. He's usually, or he or she is usually the builder of the product. Sometimes they're also practitioners or former practitioners. So they have much more credibility in front of the buyer than somebody who has sales in their title. So, and the buyers know that the seller's incentives are aligned with getting you to say yes to buying the product versus the founder might also have those same incentives. But, but there's a credibility thing. And, and, and so if you've never sold, don't, don't, don't bring in a seller. Bring, you know, if you need help, if you need advice, you need consulting for sure.

Eyal Worthalter:
You can, you can get someone like you, like me, you can, you can read stuff. There's books, there's videos, there's, there's so many things you can do but go and sell on your own. Get the company to at least a million ARR, more likely 5, maybe even 10 million before you start really, really considering to bring in a sales leader.

Andrew Monaghan:
I think the other thing that I see on top of that il is the founders rules for selling, right. What they say and do and offer an act in front of a prospect is not something they'll usually let salespeople say and do an act. They don't Create products on the. Not allowing salespeople to create products on the fly. They usually don't allow sales to make up pricing as they, as they do things. They don't allow founders, salespeople to change the roadmap on the fly, things like that. And you know, quite readily when you're in that mode, that's what you should be able to do. But, you know, that's something that the founder has the, I guess, the internal capability to do.

Andrew Monaghan:
But also, again, I think also to your point, you know, a lot of former practitioners, they, they can know how to adapt for the situation that they're the person they're talking to. They know how to change it up quickly on the fly. Whereas if you're a salesperson, you may be a little bit more junior. You probably just don't have the wherewithal to do that.

Eyal Worthalter:
No. And even if you did, right, And I had a lot of room to, to, to negotiate in my list in my last gig, right, I had ownership over, you know, almost every pricing, customer success. You know, I would say everything except the roadmap. So even if I had all that leeway to make decisions in front of, in front of the customer, the founder has that complete perspective on where the company is at, how much resources they need to build to continue building the product. Say if, you know, if there's something that they want to develop down the road or something, the investors or a potential investor has told them, hey, you should go in this direction. And so if, for example, if they're trying to win over an enterprise customer as their first reference, right? My job is to sell in a sort of sustainable and more likely profitable way. Whereas the founder might be able to say, hey, I'll do this one for free just to get the reference right. And those things are something that the founder needs to do at least until, yeah, I want to say 5 million, right? But there's no perfect milestone to that.

Eyal Worthalter:
Right. But there's no threshold where you should say, this is a point where you hire someone. But around that number right now, I.

Andrew Monaghan:
Bet the pushback you would get from founders, you kind of alluded to this in your article. One is, look, I'm just not a salesperson, you know, I can do my best. But my goodness, imagine how good we could be if we had someone who knew what they were doing, running sales or doing sales. That's one thing, right? Second thing that you probably hear is, but my VCs kind of forcing me. My VCs, the one, the board, the whatever, say you Gotta go hire someone, right? You gotta go get it done. And the other thing is that, you know, they just don't have the time. Right. I mean, if you look at the founder's job is so many different hats they have to, have to wear, especially CDA kind of stage right.

Andrew Monaghan:
You know, they just don't have the, they know, they probably know it's super important that sales needs to be done, but they also know they've got 45 other things that are climbing for time and they're thinking, would it be good if I just had someone to just take all this off my plate? Right?

Eyal Worthalter:
Yeah. Look, let's break those three into, into parts, right? Like one, right. If they think they, that they can't do it or they're not good enough as a, as a seller, I disagree with that. Everyone's in sales, right? You know, whether you're trying to convince somebody to buy a product or you're persuading somebody to give you information, you know, to sell is human. That's what one of my favorite authors, Dan Pink says. So the fact that, yeah, maybe they're not the person that can build the sales system, but sell like, you know, talk to customers, try to understand their problem and see if the product that you're building fits their challenge. That's a skill that they need to master. Whether they're pre revenue or about to go ipo, that's a skill every leader needs, not just a founder, whether you're a CEO or head of product.

Eyal Worthalter:
It's a soft skill that's going to be useful all the time. Even if they think I'm not the best one, they need to master that skill. So I do disagree with that. The second component, the VC's pushing them. Obviously I'm biased here because I've seen good VCs chase their portfolio companies down the path of hire as fast as you can scale and keep adding bodies until scaling. Right.

Andrew Monaghan:
Take more money.

Eyal Worthalter:
Exactly. Right. There's, there's, you know, the faster that you spend it, the more that you need to raise. Right. The more that you need to raise the chunk, the, the smaller the chunk that you keep. Right. So, so there's, they need to understand that. I hope, I hope founders have found, you know, by now that, that, that you know, raising money can be a doctor.

Eyal Worthalter:
So, and obviously I, I, I can't, I can't put myself in their shoes. But, but they need to figure out how to push back and manage the expectations of their VCs. I'm not saying the VCs are wrong. Right. Sometimes hiring a sales leader is as important because it allows the CEO to, or the founder to step away and navigate the other things that he or she needs to do. But at the same time, and I heard this from, I think it was Safiyo Suri, the head of Bravado, who's sort of a talent agency for salespeople. He was at a VC conference and one of the VCs was joking plainly on stage saying something like, your best salesperson is going to be your best sales leader is going to be your third one. Because the VCs know that you're going to make mistakes.

Eyal Worthalter:
So he wanted to make that mistake as fast as possible twice so that you get the third one right. Which, you know, for me as a VP of sales, it sucks because it means like, hey, I'm going to be like the bait to get the second or the third one in to make it right. So we could dive on that conversation a little bit more and you know, and expand. And there are a lot of, let's say, emotions around that that I disagree with at least a fundamental idea that, hey, you're going to have to hire somebody to fire them. Like that, you know, just doesn't go in.

Andrew Monaghan:
Right. That seems like a, I don't know, it seems like a very cavalier way to think about it.

Eyal Worthalter:
In my mind, you're playing with people's lives and that I don't like that. And I hope that most founders would disagree with that.

Andrew Monaghan:
Right, Right. Yeah. I mean, founders don't go into thinking, no, this I'm probably going to hire. Wrong, let's just hire someone and get through them quickly. Right. They really are trying to get the best people they can. In your article, you go on, you kind of break it out, you know, stage one, which is the pre revenue stage, getting the first design partners, things like that. And then you get to stage two, which you call early validation or the, the dangerous middle.

Andrew Monaghan:
Right. This is that 1 million to 5 million ARR. 10 to 40 customer range.

Eyal Worthalter:
That's the hardest part. List.

Andrew Monaghan:
Yeah, yeah. And you say, look, you'll be tempted to hire a VP of sales. Your investors will probably push you to fight those urges, stay strong. What you should do instead is hire sellers, not a sales leader. So that, that's interesting take. So why, why do you say that?

Eyal Worthalter:
So let me. One of the last things you said in the previous question was that the third reason a seller might not, or a founder might not hire or might want to hire is they don't have time this is a good segue into that conversation. So it's exactly okay. You found a few customers, you're at that 1 to 5 billion range, but you're still not sure if you have product market fit. Right?

Andrew Monaghan:
Right.

Eyal Worthalter:
And like I said, a VP of sales is going to come in and try to build a repeatable motion to scale that go to market plan and figure out how to attract more of the same customers that you've already sold to. If you aren't sure that those are the right customers and you need to be like absolutely, hands down super convinced that you that those are the right customers, then a VP of sales is an overkill at this time. I'm not saying it's wrong. It's not as wrong as like at the pre revenue stage, you can still do it, but you can wait a little bit longer and you can delay that decision and that's going to be better. And I say fight those purges because it's going to be better. And then at the same time, if you are already at that 1 to 5 million range and so your calendar is all booked, one of the things I said is I use the same rule if I'm, I would use the same rule for the founder. If your calendar is full of discovery meetings and you don't have enough time to follow up with those meetings, great. That's when.

Eyal Worthalter:
If I had an aide right now and I see his or her calendar all booked, great, it's time to hire a new one. Right? So it's the same thing. You're a founder. Hire a founder ae, set the right expectations for them. Don't, don't sell them the job. Like, hey, you're going to come in as a founder AE and you're going to build a team that they might, right? They might grow to be that sales manager. But, and that's a separate conversation. But the same skills that make a great founder AE probably play against him or her to be a great sales manager.

Eyal Worthalter:
It's a completely different mindset and even profile. So my suggestion was bring in one, maybe bring in two sellers, hand them over the accounts that you have right now, hand them over the customers from a relationship management perspective, right, you don't need the founder involved in a negotiation with procurement more than just like the big red lines, right? Like the back and forth. You don't need them documenting how the POC went, right? Like you can have the AE or if you already have a pre salesperson doing that, great. So, and then once you have existing paying customers, you can have this ae, go and meet with them and try to understand what made them sort of buy the product and go and see if they would, you know, be a reference, go and see if they can bring you in, into another customer. And so use that additional pair of sellers hands to go and do some of the day to day stuff that you're currently doing while you focus on, on that higher level sales strategy or higher level figuring out if you have product market fit. Because you don't suddenly wake up and say, great, my product has achieved product market fit. Right? It's not something that you suddenly, it's not a switch, right? It's like a knob that suddenly something clicks. Right? From my view and I don't think there's any consensus, but from my view you can say that you've sort of achieved product market fit when the customers start talking about you without you asking them.

Eyal Worthalter:
Right? When you start to see them posting about you on Reddit. And not asking them also means, hey, they're not designed by partners that you convince them in any way, right? You didn't give them a super special discount, you didn't give away the product, they paid fair and square for the product and now they're raving about it. Great. That means that is your buyer and you need to find people like that that will, that's when you can say, great, I found my, my right icp, I found my right buyer Persona. Let's test that. Right? And so you have that new seller that you brought in to try to find 2, 3, 5 more like that and if they find them, great, then you're ready for that BP of sales because then you have a potential way to scale.

Andrew Monaghan:
Yeah. This is such a messy part of the process, right? Because it's your point. It's not like you're sitting there staring at your Salesforce dashboard and something turns green and go, yay, we got product market fit. Right. It's just not the way it works. And there's this three steps forward, two steps back, five forward, eight back. You know, you're in that kind of weird world and this is kind of one area that I kind of looked at your article and I kind of looked a little bit with an eye by raise just from a sense of what I've seen out there in the marketplace. I think that, because I've heard both sides of this before, right? That get the person in early or don't get the person in early and all this sort of stuff, right? Depending on what angle you're coming from.

Andrew Monaghan:
I think the thing that sometimes people don't think about is the idea that a very aware head of sales at an early stage company understands that their job is not to, you know, build the systems and scale the team quite yet. Right. I remember I talked to Cullen Jones when he was the first CRO at Wiz and he talked about how in the early stage it was all about listening. When he joined, just to put it in perspective, he joined Wiz, they had one BDR on board. Ryan Buchanan had been there selling with the CEO with sf, right? Which you know, is what he's talking about, right. He was lighting up the meetings and then, you know, team them up for Assaf and then they just hired one ae. I don't know, literally like two or three weeks before I think Colin joined. And Colin came in as, I don't know if it's official title was CRO, but it was vp, it was the head of sales, right.

Andrew Monaghan:
It was not a rep trying to be a sales leader. It was like you're going to be the, our head of sales, right. And he said he spent the first months listening. It's all about listening, listen first approach and then feedback to the company. And I think this is an interesting kind of angle to this is when in that messy middle, in that messy process, if you do approach it as a red blooded salesperson, I'm here to get revenue and customers and logos and I've got my comp plan and that's my job. That's not what's needed. Whether you call them the VP of sales, you're hiring an ae, you want someone who has that listen first approach, who understands that. I think that half their job is listening and adapting and feeding things back and half their job is then to get customers.

Andrew Monaghan:
And then the question to my angle is who's the best person to do that, right? Who is the wherewithal, the experience, the gravitas to have those conversations? Is it the up and coming AE or is it the up and coming sales leader who maybe has a couple of stints under his belt somewhere else and then is really good at navigating those conversations. But who understands I'm not there to build Salesforce and medic and all this stuff on day one? I'm here to actually get the motions going. So I know that was one area I was kind of scratching my head a little bit thinking how does that apply?

Eyal Worthalter:
No, no, no. It is definitely not the junior ae, right? The founder. It's not that one. You need that person for tactical purposes. That's it, right. The strategic thinking of understanding how you're going to go to market and what pain your product is actually solving and where in the journey of building that go to market motion you are. That's going to come from a 10 year VP of sales that has done it before. I do kind of hate the Wiz example, man, because.

Andrew Monaghan:
No, no, dude, let me give you some more. No, no, I'm with you on that. I hate the people that say, well Wiz did this, so do this right, so let me give you some more. So Chris Degnan, he was the first, he was actually the first sales hire at Snowflake, right? He wasn't a rep coming in. He before that he was the VP of the west at Identity company. Came in as the, literally the first person in sales as Snowflake, right? And what, 10 years later he eventually retired. And then you look at Eric Apple. Eric Apple was the first sales hire in island and he went in as the head of sales, right? And he built his team up from there.

Andrew Monaghan:
And before that he was a second line manager at Symantec at VP Title Symantec and Cyber Reason as well. Mike Baker, he grew his career at McAfee. He left McAfee as the Global Vice President of Commercial Sales. At McAfee he went to Cylance as the head of the West VP and then he joined Armis as the first person in sales again, not as a rep, as the person to lead the sales team. He was number two person ever hired in North America. So it was him and like some sort of ops person who was in North America. And he grew Armist a lot and then he went to no Name and then to Aim and then you know, go on like Perelskin, Dan Perelskin, he grew his career at McAfee and Tanium and then he was the first go to market hire as the leader at Axis Security and then Access got bought by hpe. So I look at these, I'm very cautious about saying, look, oh, you know, here's a couple examples.

Andrew Monaghan:
Therefore, you know, as possible. I think, you know, each of these companies, they broke out for lots of reasons, not necessarily because they hired a sales vp, right? But I think, I think it just kind of points that you got to be very careful I think as a founder about what you're hiring because you know, you might think, well, I'm going to get an ae. And then you might not have the experience to know is that the right AE or whatever or Everyone tells me not to hire a VP because they tell me they just want to build process, you know, that's not necessarily the case.

Eyal Worthalter:
No, I wrote that like any, any person can write a sales process, man.

Andrew Monaghan:
I mean, yeah, you're, I saw that. You're dead right.

Eyal Worthalter:
It's, it's not a genius that like, come on, it's a process. You sit down and you say this is how I think it should be and that's it, right? And put in a piece of paper and then, you know, define the basic methodology around it and that's it. No, no, no, I, to your point, I think of, I mean, maybe because, you know, I'm a, my background, I'm an engineer, right. So I think of frameworks to do things, right? And so the same article I was trying to come up with, hey, is there a framework for hiring the right person at the right time? Right? And that's how I try to approach it, but it's not perfect. There are exceptions to the rule. The wiz example does set me apart. Sorry man, it just. You have cyber stars behind you and again, but using that as an example, right, you had a savvy CEO with an sdr, so a junior ae.

Eyal Worthalter:
Not ae, but somebody getting meetings and then putting a very good CEO in front of customers so that you could get sales. And then as he was doing that, you brought in a VP of sales to listen into what he was saying and what the customers were doing. But as I've never abdicated, right, I've seen him still in sales meet like the first I saw a presentation he did at a Microsoft event on they closed like a seven figure deal over the Azure marketplace, right? And everyone was like, how can you close a deal over the marketplace? And then he gave a presentation around that. And yeah, maybe like the initial lead, right? The inquiry came through the Azure marketplace, but it was still a soft pitching, right? So to me, that's the best example of a CEO that's still selling. Doesn't matter. This was obviously pre Google, pre the first Google attempt at acquiring them. So they're still, I don't want to say up and coming. They were big enough already.

Eyal Worthalter:
But he was still selling, right? My point to, hey, if you get pressure from above and you don't have time, but you're still not sure about the BP of sales, bring in a junior seller, right One, if you make a mistake without hire, right one, it's not the end of the world. And by a mistake it means it's going to be very hard for you to find out if that person is good or not. Until you have that person working with you. Right. If that person is not the right fit, they might still have room in their organization because they spend time learning from you as a founder how to pitch. Right? So they might still, hey, you bring an AE and that person is not the best one. But then if you bring another one, there might be room for improvement between two of them or maybe you end up replacing that person. It depends on the, on the scenario, right? But you still have that, how do I say that context of, hey, if you're busy and you're getting pressured, don't just go and hey, I'm going to hire a VP of sales.

Andrew Monaghan:
And yeah, yeah, no, it's a great point you said about don't. I think also hiring someone like that doesn't mean advocating the responsibility for it. When I first, early on in my career, I was a company and it was a decent sized company and the head of one of the divisions, I ended up spending a bit of time with him. And I remember he told me one day, I can't remember the context why he told me this, but he told me one day he goes, andrew, the thing to remember about technology is there's two types of people that matter. Those that produce products and those that produce orders. He said, everyone else is overhead. I was like, okay, I think if you could embrace the idea, you as a founder can devolve yourself from both those areas. So you just don't know what's going on.

Andrew Monaghan:
Trust someone, everybody's going to be fine. Because you know, it's not right. No, it's not the way things are. So you have to know, you have to be closely aligned to those things.

Eyal Worthalter:
That was also one of the reasons that the article sort of started coming together with a lot of feedback that I had from Ross was that he found a lot of founders as well, that, hey, they're, they're, they're builders, right? They want to spend their time coding, they want to spend their time getting the product, shipping the product. And so they bring in the VP of sales to hand over the reins of, of the sales motion. That's what I mean by advocating, right? You can't do that. You can't, right? And, and so that's, I would say, like the biggest pitfall of, you know, I told you in the beginning, right? And the one thing I want people to remember is sales, you know, the, doesn't generate demand. The second one is that you can't hand over the reins for whatever reason, whether it's because you want to focus More on building or you don't think you're the right person. Nobody's born learning how to be a CEO. Right? You grow into the role and you learn. It's the same thing with the sales skills.

Eyal Worthalter:
So I think bringing in a VP of sales, if as long as you have the expectation and they have the idea that hey, they're gonna come in and listen and for at least the first six months, their job is to understand before starting to build, then great though. You know how many VCs right now give a VP of sales 6 months just to listen? Right. You know, cybertarks understands they had a great thing that SAP was putting together. So anyway, there's not that many out there that give you that wrong way. Right.

Andrew Monaghan:
I think one of the things that you also said in the article, I think it was implied as opposed to saying it. But don't hire one person if you can hire three or four or five because then you get the understanding. Well, is it the person that isn't working at, Is it the process? Is it a product? Does it work? What is it? Right. If you hire one person, hope it works, then you just don't know what the failing point is.

Eyal Worthalter:
Yeah, that's. I mean that's just a common sort of a hiring practice. Right. Try to figure out where's the breakdown in the issue. Right. And especially if you're a first time founder and you've never sort of hired other leaders. Right. You're going to make mistakes.

Andrew Monaghan:
Yeah, a good way. It's interesting, as I was reading your article, I know a story from my past, so I spent a bit of time at Tanium. I don't know if many people know this real founding part of this. I'm not giving away anything that's not public already, I don't think, but Orion, who was the son, David was the dad. They were the founding kind of family of Tanium. The first person that he actually hired to help with go to market stuff was a guy by the name of Todd Bryden. And Todd's job was to, he talked about, it was the tee up meetings for, for Orion. Right.

Andrew Monaghan:
He was super experienced. He wasn't like a junior SDR on that, but he was one of these guys just rabbit, right. You give him focus on something, he just delivers. Right. And that's what his job was, to do that. But the really interesting thing about the Titanium Progress was they wanted to get more validation of the product. They wanted to get customers. How do we speed this up? They actually did a deal with McAfee and McAfee OEM'd the Tanium product in the super early days.

Andrew Monaghan:
This is probably 2012, 2013, something like that. And Tanium actually didn't take much revenue. They gave most of it to Maxfeed, but they just wanted to. They suddenly had like 300 people selling, selling Tanium. Right. And they would just tee up meetings all day long for Orion. Orion was just like doing it again and again and again. They got a whole bunch of customers and then what they did when they were ready to hire their, their, their first sales proper sales team at Tanium, they hired a top three sales leaders in the Americas out of McAfee.

Andrew Monaghan:
They hired Carpenter, the head of the head of Americas. Brian Gumbel was the VP of the asset the east in Canada and Ty Fag was the VP of the West. They just took them right into tanium and obviously McAfee wasn't happy. They just stole that whole layer of management. But that's what gave them the foundation. Right. And it was really interesting to see, okay, how do we get customers, how do we derisk the process? And then through the process of the Macafee deal, you know, Ryan would have got to know Carpenter and Gumbel and Ty. Right.

Andrew Monaghan:
And nobody wants, okay, that's my team, right. I trust them, I know them, I know what they're doing. Kind of interesting different way to approach it. Right.

Eyal Worthalter:
He worked with them side by side winning and probably losing deals. So he got to see them like thick and thin more importantly. Right. Just as trying to sort of study it as let's say a case study. They didn't go and build an outbound or inbound or PLG motion. Right. Like they did an ecosystem play to get product market fit. I think that's a wonderful.

Eyal Worthalter:
And that's why tiny means like that. Right. So I think there's going to be more opportunities for founders to go and build products in that manner. And I think it's going to be moving forward harder to go and build go to market motions. A traditional way of outbound from my perspective is extremely challenging, if not a dead motion right now for the typical SDR approach. It's just too expensive. So I think that the idea of bringing in someone to do a technology alliance or an ecosystem play first as the starting point I think has a lot, a lot of merit. And I would try to advise founders to go in that direction first before trying anything else.

Eyal Worthalter:
I think it's a great idea and.

Andrew Monaghan:
Especially these days, alright. You know how more difficult now it is to get attention and pipeline and meetings than it was 10, 15 years ago. If you've got a way to tap into that, then that's going to be huge. Let me ask you one more thing that you talked about. So you moved on to stage three, scaling systems and hiring your first sales leader. You gave three criteria for that leader, and it's interesting that only one of them was their ability to build and scale the go to market motion. Right. You said the first thing was leadership.

Andrew Monaghan:
The second thing was a trustworthy person you really like. And the third thing was their ability to build and scale the go to market motion. Tell us more about why you could have come to that conclusion.

Eyal Worthalter:
I had 10 more things, I kid you not. I had an entire three or four additional pages that I thought about because I came up with these things based on the people I've worked for and the people I've seen and people I've admired over the past years that I think, man, this is such a great leader. And so I tried to distill what made them great, and then I put them into paper and then I ended up with really like four or five pages longer. And then, you know, I said, okay, this is already way too long. We can't add, like, we can't add that. Okay, if I can, if I can narrow it down, right? What, what would that be? And, and yeah, obviously the building, the go to market motion, that's like the table stakes. But also, you know, one, one of the things like that that I said is like, you, you, you gotta like this person you're going to become. You know, if things work right, you as a founder are going to become extremely close with your VP of sales.

Eyal Worthalter:
You're going to be talking with him or her all the time. You sort of got to be friends, right? Not just, not just colleagues, not just, oh, he reports to you and your business acquaintances. You got to feel like you can work with this person all the time and call them at any time and they can call you at any time. And if it's a Sunday, you can chat over WhatsApp and they don't feel bad. You don't feel bad about it. So that's what I tried to say when I said you have to trust them and they have to trust you because it's a relationship that has to work. If that relationship doesn't work, that's it. I'm going back to.

Eyal Worthalter:
There's a post from Sam Jacobs, CEO of Pavilion, where he was talking about a friend of his or somebody he knows where he was the sales leader and he had a very good relationship with his own CEO. But something shifted. I think he made a mistake. I don't remember what it was, but the CEO, suddenly the relationship shifted a little bit. The CEO stopped looking at him a second less, right? During meetings or he was a little bit more. He was a little bit colder. And then Sam said to these, his advice was leave, right? You're not going to be able to fix that relationship. And the guy did the opposite, right? He worked his ass off to make sure that he earned that trust.

Eyal Worthalter:
And that didn't happen. Right. I think once trust is broken between the CEO and the leader, it's better for both of you. Exit. Right? And that happened. This happened to me a while back, right? I tried all my best to earn back my CEO's trust and I couldn't. And ultimately I parted ways and it was better for me in the long run. And so I looked back at that and I thought, okay, that's when I had trust.

Eyal Worthalter:
And then I lost it. Right? You, what if you never have that? What if you hire somebody but you don't really trust him or her? That's just not going to work, right? So that's what I said. This is somebody you have to trust. This is somebody. Is he or she is going to be your body for a long time? I think that's, I would say, the most underrated thing that, that I could add.

Andrew Monaghan:
And that to me is one of the biggest differences between being in a medium to large company and being in a small company is that tightly integrated leadership team happens. It's needed at the smaller company. And you all have to know that this is going to be messy as hell, right? I want to forecast things that are much less likely to happen than if I was at a big company with 500 reps and a lot of coverage and padding and things like that. It's a lot more transparent at the smaller company, it's a lot more volatile. Things are going to go wrong and right and inside and outside all day long and we need to trust each other, that, hey, we get it and we support each other, right? It's such an interesting relationship to have.

Eyal Worthalter:
Right? And that's the one thing that I think Roz and I see things the same way. We're building products that are basically used to increase trust in society. Right? You gotta start with, you know, customers trusting you. And from my view, you have to start with you trusting your sales leader and you and the sales leader trusting your founder. You don't have that. It's just not going to work out.

Andrew Monaghan:
Yeah, yeah, it's interesting. One of my clients, they had a good outcome in the end, but I know that the head of sales wouldn't work with those founders again because of how certain things were handled. How, I don't know. I can go a lot of detail, but it's just clearly the process ended up with them and the experience. That said, you know, that's not someone I trust to make the right decisions, handle themselves appropriately, be the adult in the room when things are good or bad. And it's not until sometimes you get into the nitty gritty that you actually learn what each other is like. Well, yeah, listen, that was an interesting conversation for me. I hope this for you too, and hopefully for our audience.

Andrew Monaghan:
This is such an interesting area because I think to your point, it's so messy. You try. You know, what I really liked about your article is you're trying to make sense of something that's actually very messy. And, you know, I gave you a few outliers and things like that, and we kind of recognize that, you know, there's no one way to do it, but there's certainly some much better ways to do it than others. Right.

Eyal Worthalter:
Hopefully, you know, there's a few fewer or there's fewer people in the sort of revolving door of sales leader because of these conversations. Right. That's, that's, that's what I hope happens.

Andrew Monaghan:
Well, I hope so, too. If someone wants to get in touch with you and talk more, what's the best way to do that?

Eyal Worthalter:
LinkedIn, man. Yeah, you can find me on LinkedIn. Happy to chat. I always tell founders my advice is for free. I've made so many mistakes that I want them to avoid those mistakes from repeating. So. So yeah, they can reach me out.

Andrew Monaghan:
Awesome. Well, thanks for joining us.

Eyal Worthalter:
Thank you.