Why your first VP of Sales hire will fail, and what you can do instead
A candid guide on why early-stage startups shouldn’t rush to hire sales leadership, and how to build a sustainable revenue organization that doesn’t burn through talent
This is a guest post from a friend Eyal Worthalter, who leads security sales at Marvell. Eyal calls himself a “recovering VP of Sales” who’s spent 15+ years scaling cybersecurity teams. As an engineer-turned-sales-exec, he’s seen enough challenges hiring sales leaders to fuel a lifetime of LinkedIn rants about what doesn’t work in cyber sales. In this guest post, Eyal shares the hard-earned lessons from the trenches to help founders avoid some painful mistakes.
Introduction and the ‘why’ of this blog post
I’m an electronics engineer turned into a tech salesperson. I was lucky enough to realize early on in my career that I had more strengths on the business side of technology than behind a screen coding and building it. I’ve had every possible sales job in a tech company you can think of: I’ve been a sales engineer, an account manager, a country manager (for Mexico), led a small team in a region, led a slightly bigger team in multiple regions, you name it. I’ve even done sales enablement reporting to Marketing. I’ve had the experience to look at the function of sales from different angles. Throughout my time, I’ve tried different things, made many mistakes, although some of them had zero impact on my success or failures. I’ve also noticed that the actions of others, mainly the CEO or founder, along with the board, have had a high impact on my ability to succeed in my role.
My career, with all its ups and downs, has been and continues to be very rewarding. The one thing I absolutely love about sales, is that you have to keep learning about your customers, and being in front of customers is my absolutely favorite part about the job. But, there are days when the job is brutal. I’ve come to accept it as part of the ride, but I’ve also felt that there are things under my control that can help improve how I go about crushing or failing at my job. I tend to share these things with others in order to help cyber sales and sales leaders improve their game and hopefully thrive, rather than languish.
If you are reading this and you are building out your company or you are a VC that invests in cyber, please read ahead. Look, I won’t sugarcoat it. Following this advice means saying no to quick fixes and yes to harder work upfront. But it also means you’ll stop wasting money on expensive hiring mistakes, your portfolio companies will build sustainable revenue engines instead of revolving doors, and the talented sellers you eventually hire won’t get chewed up by unrealistic expectations.
If you are an early-stage startup, you don’t need a VP of Sales
If you are a pre-revenue or an early-stage cyber company that is still testing out the waters so to speak, you don’t need a salesperson, and you definitely don’t need a VP of Sales.
Let me explain. In 2025, salespeople do not generate demand for your product. They convert that demand into revenue. The good ones can accelerate that conversion, the great ones can replicate that process over and over and the VP of Sales can put a framework that makes this repeatable.
If salespeople do not generate demand for your solution, who does?
You.
The founder.
If you can’t get your first few customers yourself, if you can’t get your company to somewhere above the first $1M ARR (and more likely around $5M these days), how can you expect me or someone like me to get you here? You shouldn’t.
As my favorite author Dan Pink says in his book ‘To Sell is Human’, Everyone Sells. Well in this case, You Sell.
I know you probably want to spend more time building your product, or shaping the culture of the company you are building. But you have to sell. The first thing you should expect when you hire any salesperson is that they’ll be 50% less efficient at doing any sales job than you, the founder. I don’t have any data that supports this, just years of experience seeing how founders have 50% better close rates and win rates than myself and my best sellers. It’s a credibility thing, and since sales is based on trust, buyers will trust you, the founder, much more than me. My role and title play against me. Years of bad experiences with sales reps and misconceptions about the role have shaped buyers to have their guard up with salespeople. Take this to heart: you need to be the first one knocking on doors. How you go about doing that, it’s up to you, but you don’t really need a ton of tools and you don’t need to become a professional seller.
You need to find the first 5-10 design partners. You need to make sure your product solves a problem that’s big enough to move the needle on a security program and the more conversations that you, on your own, have with potential buyers, the better off you’ll be.
Looking for your first salesperson
Let’s say you did everything right - sold the first $1-5M ARR, and the time comes for you to scale. How exactly shoud you go about finding a salesperson? I think before answering how, we should start with ‘Why’ and ‘When’?
Why hire a salesperson
As Simon Sinek says, let’s start with Why. You should do some soulsearching first and have a clear idea of why you need a sales leader. Here are some good reasons:
You finally are seeing some commercial traction and want to get help scaling your GTM team and operations.
You have more customer interactions (calls, pitches, demos, etc) than you can handle on your own.
You feel that you have finally narrowed down who is an ideal customer for your solution.
At the same time, here are some bad reasons to hire a sales leader. If you resonate with the below or have felt something similar to them, there’s nothing wrong. Just being aware of this can help you articulate your expectations better to whoever you hire:
You feel like you do a better job on the product/engineering side and want to spend more time “building” than “selling”.
You are tired of the follow-ups, rejections, hassle and hustle of sales. You are ready to pass the torch to someone who’s done it before.
Your VC is pressuring you to hire a VP and a bunch of sellers.
Like I said, there’s nothing wrong with any of the above reasons, they are perfectly natural and happen to many founders. The reason I’m saying these are ‘bad’ reasons is the fact that bad reasons can lead to bad decisions which in turn lead to bad hires. Let’s explore each bad decision and the pitfall it can lead to.
Pitfall 1: “You’ll do a better job building than selling”. Even if you are a product person by heart, you’ll always be in sales. You can find ways to spend more time building without fully letting go of your sales hat. The closer you are to customers, the better product you’ll be.
Pitfall 2: “You want to abdicate the boring and challenging parts of the sales job”. Congrats, you are exactly like every B Player sales rep I’ve hired. You know the difference between A and B players? Top reps do all the hard and boring work despite not wanting to do it. So if you hire a seller because you don’t want to do his or her job, don’t expect them to do it better than you.
Pitfall 3: “Your VC is pressuring you”. Why do you think they are telling you to go and spend all the cash they have given you in the last round? The most respected VCs know that you’ll make mistakes hiring and the faster you make those mistakes the faster you can rebound from them.
I’m hoping I can prevent you from making those mistakes because they not only will hurt your company, but they’ll hurt someone who’s eager to do a good job and is being set up to fail. The more sales leaders that are hired for the wrong reasons described above, and the more salespeople that fail because they weren’t set up for success, the more we in the industry perpetrate the misconception of the funcion of sales. I hope we can break the cycle by creating more trust between sales leaders and founders, thus avoiding hurting the function and reputation of all sales leaders out there.
Here’s my ask and my offer: please spend some time thinking about your ‘reasons’ for hiring a seller before embarking on this journey. If you aren’t sure why, reach out to me and I’m happy to bounce ideas, no strings attached.
When to hire the first salesperson
Now, let’s talk about when to hire. Let’s assume you’ve spent months, and more likely a few years at the helm of your company, you landed your first few paying customers. None of them have churned, and then you spent some more time getting a few more customers. Maybe you’ve even gone ahead and had your first serious raise and so your VC’s are telling you it’s time to move away from founder-led sales.
Before you even go about doing that, you need to be absolutely certain that you’ve achieved product-market fit. Now, I’m not an expert on this, you can definitely read more about this from Ross and many many other folks. But you know how I, as a sales leader, evaluate whether or not a company has achieved product-market fit? It’s simple: you’ve achieved PMF when you have customers actively referring your solution to others without you ever asking them. Key words here: ”customer(s)”, as in, more than a single person, and “without you ever asking them”. This also means that if you gave equity to any of your design partners or if any of your early adopters have some form of vested interest in seeing your company succeed, then you can’t consider them as someone that you “haven’t asked for a referral” because the reality is that they are biased.
True product-market fit happens when you find that credit union security analyst on a reddit thread saying that they did a POC with you and absolutely loved it (while naming out the reasons why).
This is the first critical part of hiring your first seller because if you do not know if you’ve achieved product-market fit, then how can you point a salesperson in the direction of the market that wants your product? The tricky part here is that you don’t suddenly wake up one day and realize that product-market fit is just “there”; it’s a discovery process that happens over the span of months. All the while, you still need to be doing your doing.
I’ve put together the following chart that can help you first identify where you are in your journey, and based on this define the type of seller you will need.
Stage 1: You’re not ready yet
Under $1M, fewer than 10 customers
If you’re here, the answer is simple: don’t hire anyone.
Remember what I said earlier? Salespeople convert demand into revenue; they don’t create it. At this stage, you haven’t proven there’s enough demand to convert. You have three critical advantages that no salesperson will ever have:
Credibility - Buyers trust founders more than sales reps
Product knowledge - You know every feature’s origin story
Flexibility - You can adapt your solution on the spot
What you should focus on instead:
Build your LinkedIn authority around the problem you’re solving
Have direct conversations with potential customers
Learn what messaging actually resonates (not what you think should resonate)
Understand the real buying process your customers go through
The exception? If deal flow is overwhelming your schedule AND you’ve identified clear patterns in your sales process, consider a Founding Account Executive, which is the hire you’ll need on the next stage. Let’s be clear on their role. A Founding AE is not there to generate leads or create demand, close deals independently, or build your sales strategy. Instead, a Founding AE is there to handle post-technical-win logistics (contracts, onboarding, stakeholder management), learn your demo and objection-handling approach, and free you up to find the next customer while they manage current deals. You’re still running the show. You’re still the one earning trust and closing deals. The Founding AE just handles the administrative heavy lifting after you’ve done the hard work of winning the customer over.
Taking this approach will do two things: build confidence in both the AE and SE and allow you to be close enough to the field to figure out if you’ve really achieved product-market fit.
Stage 2: Early Validation or The dangerous middle
$1M-$5M, 10-40 customers
I honestly don’t think there’s barely any difference between Stage 1 and Stage 2. Yes, you’ve made progress. You’ve closed more deals, maybe even doubled your revenue. Congratulations! $1M to $5M is extremely hard and many don’t ever make it. But here’s where founders make a critical mistake: they think hitting a few $M means they can hand over the sales motion.
You can’t. Not yet.
Remember those “bad reasons” I mentioned earlier for hiring a VP? This is exactly when they start gnawing at you. When you are tired of rejections, when you lose a deal you thought you had, when that champion starts ghosting you. I feel you. I’ve been there. You think it’s time to bring someone in to “help” but you are confusing help with handing over the reins. On top of that, you want to get back to building, and your investors are asking about your “sales strategy.”
Fight those urges. Stay strong.
What you should do instead: hire sellers, not a sales leader.
What kind of “seller” am I talking about? I mean a full-cycle Account Executive. Not some senior rep from Palo Alto who expects a dedicated SDR to feed them leads. You want a startup seller, someone hungry who doesn’t mind doing the prospecting work themselves.
Look for:
The AE who was recently promoted from SDR (they know both sides)
The mid-market rep ready to move into enterprise (if you are targeting enterprises)
Anyone eager to work directly with founders and willing to grind
These sellers exist, and many are grateful for the opportunity. The best ones can even set up their own sales tech stack if you give them a modest budget for tools. And on the topic of tools…
A word about AI SDRs (spoiler: don’t bother yet)
While we’re talking tools, let me save you some money: AI SDRs in cybersecurity are terrible right now. It’s not the technology that’s the problem, it’s everything feeding into it:
The purchase intent data is garbage
The “personalization” signals are generic
The source content is recycled and bland
Most importantly, you probably can’t articulate your unique value proposition crisply enough for AI to get it right
I used AI SDRs back in 2017 with moderate success, but that was before everyone was doing it. Now? The market is flooded. Whether you’re human or robot, cutting through the noise is nearly impossible.
I’m not anti-AI - use it to enhance your sellers’ performance, but AI SDRs aren’t the silver bullet in 2025. Maybe that changes, but for now, invest in hungry humans instead. How do I know? In 2024 I had side by side outbound motions of 11x (AI SDR) and Glen Coco (outsourced SDR’s). Who won? Neither, my AE’s signing up new channel partners generated more demand than both of them combined. Partners are key to your success. If I had to repeat this in 2026, I would pick the human SDR’s because I create the pool of talent for future development into AE’s that move to the field. Maybe by 2027 things will change and the AI SDR can do everything a human can do much better. Who knows?
So TL:DR, hiring full cycle sellers will be better for you at this stage. More importantly:
You stay close to customers (which makes you a better product builder)
You continue learning what actually drives deals (not what you think should drive deals)
You avoid the expensive mistake of hiring the wrong sales leader
You keep control over the sales process while getting help with execution
The reality of managing multiple sellers:
Yes, onboarding 2-5 sellers is work. Yes, you’ll make mistakes - it’s better to make mistakes with AEs than with a VP who costs 3x more and has 10x more impact when they fail.
How to set proper expectations:
Be brutally honest in your hiring conversations. Don’t sell them on “building their own team” if you don’t see leadership potential. Instead, say:
“You’re joining to help us expand our efforts. You’ll work directly with the founding team. This isn’t about you running your own show - it’s about learning our process and executing it with more customers.”
For many good sellers, this is actually appealing. They get ground-floor equity, direct founder access, and the chance to shape a sales process rather than inherit someone else’s broken one.
When to hire your next seller:
Simple rule: when your current seller’s calendar is full of qualified opportunities.
This same rule applies at every level - from your first AE to your eventual VP of Sales. Full calendar = time for another hire.
The chart isn’t a formula:
Don’t think “$1M = hire 1 seller, $5M = hire another one.” Every company is different. Focus on capacity, not arbitrary revenue milestones.
The main takeaway you should get from everything in this stage is this: you’re not delegating sales, you’re distributing execution while keeping control.
Stage 3: Scaling Systems and hiring your first sales leader
$5M to $20M ARR
This is where a proper VP will start adding value, someone that can now take what you’ve built and help get it to the next level. If you have 2-3 sellers (or maybe more) chances are not all of them are A Players. Your VP is the one that can whoop them into top performers, or replace them with better sellers while also setting up the beginnings of what a true scale-up sales org will look like.
How to hire a VP of Sales
Just like every GTM expert will tell you that you need to find your ICP or define your buyer persona, when starting out your search for your sales leader you ought to look for the “ideal candidate” by first defining it. The challenge is putting into words what an actual “good” sales leader is, because you know that good sales leaders do, which is “they make it rain”.
Criteria 1: Leadership
A good sales VP is, first and foremost, a good leader. During your interview process you need to be able to identify the traits of a good leader. They should have the ability to have tough conversations, they’ve hired and fired, they’ve nurtured and coached people into promotions, they’ve turned B players into A players. I can probably put together a list of a dozen traits that you need to look out for and some interview questions to guide you but that will probably take at least a couple of pages more, so maybe that’s for another time.
A natural leader has the emotional intelligence to speak up to you and tell you when they think you are wrong. They should be able to push back respectfully, and not say “yes” to your face when they are in fact, thinking of the opposite. If you as a founder end up surrounded by “yes people”, you won’t be able to see where the issues are coming from and you’ll take longer to address those issues.
Criteria 2: A trustworthy person you really like
You will have to get very close to the VP of Sales for this to work out. You will have to like them, and have many difficult conversations with them. You’ll spend time in the field, visiting customers together, strategizing about customers and deciding the future of the team. You will have to like working with them. You should find time to meet with them face-to-face during the interview process, grab coffee or lunch, and get a feel for how they are.
If you’ve found someone that displays the traits of a leader and you have chemistry with them, you have 50% of the job already done. What’s the other 50%? Their ability to build and scale your GTM motion.
Criteria 3: Their ability to build and scale the GTM motion
A lot of founders I’ve talked to tend to think that bringing in a VP of Sales requires the individual to build a sales process or improve the current sales process. This is a problem. Anyone can create a sales process, so spending time focusing on the sales process during the interview is a waste of time.
Instead, you need to find out about times in their careers when they turned nothing into something, where they’ve sold a product that was hard to sell and with very little support and infrastructure. This is why tenured leaders at larger cyber companies rarely do a good job at an early stage startup. I’m not suggesting to avoid someone from a larger company, because chances are, they have also seen how great companies work and have seen and learned how a well structured sales machine looks like. But it’s important to have someone with a balanced experience of seeing what success looks like with the startup mindset and experience of someone that has sold with zero support.
Experience matters, but more than experience, lineage is important. Who and where they sold at means less than who they sold from. Ask them who they learned sales leadership from, and then find out more about that person, talk to them if possible. It will give you a sense of who they are trying to become.
At the same time, if you spend time doing some reference calls, a good sales VP will probably do the same on you. If they come prepared and have tapped their network to find out more about you, your company, or your customers, then they are showing you they have an active network they can rely on to get information, source talent, and do their jobs.
So how does all the above turn into an ability to scale a GTM motion? How does experience, mentors, the cumulative mistakes and pitfalls we’ve accumulated turn us into good sales leaders? It’s all about one thing: Frameworks.
As I explained early on, anyone can put together a sales process. Maybe not a good one, but even a recent grad working for a couple of years as an SDR then promoted into an AE can sit down and write the stages of a sales motion from his or her perspective and put it into practice.
A framework is more than a process. It’s the beginning of system thinking. If you are technical, think of the difference between a coder and an architect. A VP can put together frameworks and components of processes that will work together to create more than the sum of its parts.
When interviewing, don’t ask them what frameworks or processes they use. Look for how they think on those terms. For example, if you ask them how do you hire top players, a good VP will tell you about the time they brought in someone, but a great one will share his framework for creating a pool of talent, not just one time. If you ask them how they get B Players to become A Players, look for both the example as well as the philosophy behind it.
A quick word on headhunters
Finding a great VP of Sales is hard. I get it. It might even be harder than finding customers. That’s why founders have to hire for their VP of Sales multiple times.
I think there’s value in bringing in a headhunter. But to be honest, as someone who’s engaged talent partners to recruit for me and have spent countless hours in conversations with them as a candidate and hiring manager, I can tell you that not all talent partners are created equal. My experience is that 80% of them are extremely transactional. You need to work with the 20% who are there to build a long-term partnership with you and your VP of Sales. It’s going to take you a lot of time to find someone that you’ll “match” with on the 2 criterias I’ve just described (leadership and trustworthiness), and a talent partner can help you reduce that time drastically. Just remember that speed shouldn’t be the main reason to hire a talent partner.
While most talent partners are unfortunately transactional, if you’re going to pay tens of thousands of dollars for their services, make sure they go beyond simply searching for talent. They should be your advisors. One way to separate the good ones from the rest is by testing if they can actually give you advice. Say something outlandish, like “I want my VP of Sales to be a player-coach and carry the largest quota on the team” (which makes no sense), and see if they nod and agree or try to correct you. The best talent partners will push back on you as the founder, the transactional ones will agree with everything.
Ask other founders in your network who they’ve worked with. Get references from both successful placements AND candidates who didn’t get hired. The best recruiters maintain strong relationships even when deals don’t close.
Trust your instincts
One last word of advice: trust your gut. Don’t think of “they look good on paper” or come with a preconception of “they worked at X or Y”. Once you start talking to your VP of Sales, think hard: Do you see him or her being the face of your company in that region? Do you see them as being the top person in your company, the one people will come to whenever there’s a tough challenge or a hard customer to land?
The right VP of Sales will not just answer questions during your interview. They’ll own the conversation. Watch how they naturally shift into discovery mode, asking thoughtful questions before diving into answers. That’s exactly how they’ll lead your team from day one, inspiring everyone around them to think bigger and act smarter.
When you find this person, you’ll feel it. They’ll radiate the kind of confidence and curiosity that turns prospects into believers and teammates into champions. Trust your instincts when you meet them. You are the best leader for your startup, and great leaders recognize great leaders.
Stage 4: Growth Expansion and VP of Sales vs. Chief Revenue Officer (CRO)
Before we wrap up, I need to address something that’s been bugging me: inflated titles, especially the “Chief Revenue Officer” trend.
Most “CROs” are just VPs of Sales with fancy business cards. If your revenue leader only manages the sales team, they’re not a CRO. They’re a glorified VP of Sales, and calling them a CRO actually hurts their career progression.
What a real CRO does:
Owns the entire revenue engine: marketing, sales, customer success, renewals
Manages multiple established GTM motions (not just inbound/outbound)
Creates new revenue channels: cloud co-selling, strategic partnerships, channel programs
Optimizes the full customer lifecycle, not just acquisition
When do you actually need a CRO? Your VP of Sales has already established 2-3 proven GTM motions. Say your inbound & outbound engines are working, and your channel motion is taking off the ground. Revenue is predictable. Now you need someone to find the next growth vectors while optimizing what’s already working.
Unfortunately, I’ve come to learn the hard way that the person who takes you from $5M to $20M is rarely the same person who takes you from $20M to $100M. Different skill sets, different challenges, different networks.
Your founding AE probably can’t become your first VP of Sales. Your first VP probably can’t become your CRO. And that’s okay.
This is why promising your founding AE they’ll “build their own team eventually” is usually a mistake. You’re setting expectations you likely can’t meet, which hurts everyone involved.
Bottom line: Don’t inflate titles to attract talent. It creates confusion in the market and sets unrealistic expectations. Hire for the role you actually need, call it what it is, and be honest about growth potential.
The best sales leaders would rather have an accurate title at a successful company than an inflated title at a struggling one.
In conclusion
I started this post talking about the brutal days in sales: the rejection, the pressure, the constant hustle. While this pressure still stresses me out, watching good salespeople fail because founders set them up for it is what really hurts me.
The average VP of Sales tenure is now under a year. VCs joke that “your best VP will be your third one.” That’s not funny, it’s tragic.
Behind each of those statistics is a human being. Someone who left a stable job, took equity instead of cash, moved their family, and believed in your vision. When they fail, it’s not just your company that suffers. It’s their career, their confidence, their family’s financial security.
I hope you can help make this cycle stop.
The decision to hire a VP of Sales might be the most critical hire you make as a founder. Of course I’m biased, and if you have a co-founder, then that’s obviously the most important hiring decision. But a VP of Sales is truly a strategic hire, not because they’ll magically solve your revenue problems (we won’t), but because getting it wrong destroys lives and perpetuates the myth that sales leaders are disposable.
It all comes back to your “why.”
If you’re hiring because you want to abdicate the hard parts of sales, you’re setting them up to fail. You’ll blame them when deals don’t close, when pipeline stalls, when growth flatlines.
But if you’re hiring because you want a partner, someone to help you execute while you stay involved, someone to build systems while you maintain customer relationships, then you’re giving both of you a fighting chance.
The cybersecurity industry desperately needs more trust between vendors and customers. We also need more trust between founders and sales leaders. Every time we hire for the wrong reasons, every time we promise unrealistic outcomes, every time we blame the VP when founder-created problems persist, we make it harder for the next person.
Look, I’ve been on both sides of this mess. I’ve been the sales leader brought in with unrealistic expectations. I’ve watched talented people get chewed up by poor hiring decisions. I’ve also seen the magic that happens when founders and sales leaders are aligned from day one.
If you’re unsure about your reasons for hiring, reach out. Seriously. I’d rather spend 30 minutes on a call helping you think through your decision than watch another good salesperson fail because they were set up wrong. No pitch, no agenda, just someone who’s lived through these mistakes and wants to help you avoid them.
The industry will be better when we stop burning through sales talent and start building real partnerships.
Choose wisely. Someone’s career depends on it.
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