15 min read
There’s a ‘joke’ amongst VCs and Founders that I heard last March:
Q: How do you know you’ve got the right VP of Sales at your company?
A: You’re on the third one.
*Ha Ha*
Why does this joke land? Because the average tenure for a 1st VP Sales at a SaaS startup is… *drumroll please* … 7 months.
And the average Series A startup hires and fires 3 VPs of Sales in the first 18 months. Maybe it’s less of a joke and more of a truism. A very scary and expensive one.
It’s expensive because hiring a VP Sales takes an extraordinary amount of time and effort. On average, 5 months. And when you churn that person out in <1 year, the loss goes beyond missed revenue because sales is such a tight-knit community. Word spreads quickly amongst Tier 1 VPs of Sales that this is a company to avoid. And then you’re left sifting through the rest.
How do you overcome the odds? How do you hire the right VP Sales, the first time? Read on weary traveler, you’ve come to the right place. Because the average tenure of a Bravado-placed VP Sales is 33 months. So we know a thing or two about how to get this right.
Read below to learn:
Background
How did we find the recipe to solve this unsolvable
There’s a ‘joke’ amongst VCs and Founders that I heard last March:
Q: How do you know you’ve got the right VP of Sales at your company?
A: You’re on the third one.
*Ha Ha*
Why does this joke land? Because the average tenure for a 1st VP Sales at a SaaS startup is… *drumroll please* … 7 months.
And the average Series A startup hires and fires 3 VPs of Sales in the first 18 months. Maybe it’s less of a joke and more of a truism. A very scary and expensive one.
It’s expensive because hiring a VP Sales takes an extraordinary amount of time and effort. On average, 5 months. And when you churn that person out in <1 year, the loss goes beyond missed revenue because sales is such a tight-knit community. Word spreads quickly amongst Tier 1 VPs of Sales that this is a company to avoid. And then you’re left sifting through the rest.
How do you overcome the odds? How do you hire the right VP Sales, the first time? Read on weary traveler, you’ve come to the right place. Because the average tenure of a Bravado-placed VP Sales is 33 months. So we know a thing or two about how to get this right.
Read below to learn:
Background
How did we find the recipe to solve this unsolvable problem? It starts with having a CEO who has been a VP of Sales – only a small minority of SaaS founders have sales experience. So when you’re getting advice from a VC on this topic, check their background. See if they actually have been a sales leader. If not, turn elsewhere for sage wisdom. Getting sales advice from someone who hasn’t sold is like getting golf advice from someone who has never played the game.
Big mistake.
Also, generalist exec search firms tend to underperform in VP Sales / CRO hiring, versus many other disciplines. It could also be that we have the world’s largest community of Sales professionals – 500k+ strong. Or, it could be that we live and breathe B2B SaaS Sales Recruiting. It’s our bread and butter. Of course we’re mad scientists about every detail. And like any great scientist, we’re thrilled to share our findings with the world.
What are the 2 wrong profiles for an early-stage VP Sales?
Let’s demystify the opening joke first so you can stop sweating and start absorbing info.
These are the two VPs most Founders hire first and why they’re wrong:
Ex-Big Tech VP
Many early Founders get impressed by big logos on a candidate’s resume and bring in a VP who is an expert at post- Product-Market Fit scaling.
“Oh let’s hire the amazing sales leader from Stripe!”
... are you Stripe? Do you have their marketing budget? The same quality product? The same # of reference customers? No, no, no, no. So what makes you think the success someone had in a post-PMF world is going to translate to success at your tiny startup? Answer: It won’t.
Don’t confuse a mature VP with a VP from a mature company. You have to find someone who knows how to scale a startup. The VP from Big Tech does not come with the energy, hustle, and drive it takes to build nothing into something. They’re experts at building something big into something bigger. You need a startup VP when you’re a startup. It sounds simple when put that way. But, we’ve seen countless examples of the flashy logo blinding all common sense.
Old School VP
The second mistake Founders make is they find a VP who was a standout startup VP of Sales ten years ago. They may have a glamorous acquisition or IPO on their resume. They built something from nothing and had a successful unicorn exit. But, it was a century ago in SaaS years. The experience of building a great SaaS company ten years ago is almost irrelevant now. The strategies that worked ten years ago don’t work today. We didn’t even have sales automation tools ten years ago. Now, we’ve got AI SDRs. You might think that would only make the job easier for them, but the reality is, it has changed the competitive landscape so much that if they’re still sticking to their tried and true playbook, they don’t understand how to hit quota in today’s ecosystem.
So, those are the traps and what-not-to-dos. Let’s get into the good stuff.
How do you know you’re ready for a VP Sales?
Sales VPs are expensive. You wouldn’t pay the note on a Lamborghini for two years before getting your driver's license, and you shouldn’t pay a VP of Sales to sit in the garage, either. Make sure you’re ready to roll before you take on the expense.
If you want to get the most bang for your buck, you have to bring them in after your sales team has already hit stable ground. In our article about hiring your Founding AE: Going from Founder-Led to Sales Led, we said you’ve got to eliminate a few layers of volatility and ambiguity before you make your first sales hire. Guess what. You’ve got to eliminate a few more layers before you can hire a VP.
Signs you’re ready for a VP Sales:
If you’re hitting these numbers, you’re at the level of stability you need for a VP to make an impact. At this point, you’re not going to make radical changes to your product or pricing. Those pivots are where VP talent gets wasted – it’s better to get all of that out of the way with Founder-Led Sales.
Because us SaaS founders are creative, it’s obviously possible to forge a path to these numbers without reaching stability. So, what are these numbers actually supposed to tell us, and do your numbers hold up under a microscope?
On your sales team of 5 or more, how many reps are closing deals without you, as the CEO, getting on the phone and taking them across the finish line? The right answer is: most of them, most of the time. For at least 3 months now.
If you’re still hopping on sales calls every day and quarterbacking the close, you don’t have a sales team, you have an SDR team. If every deal is a unique package custom-fitted with the prospect’s feature requests and special pricing, you are running a services business not a SaaS company. You haven’t transitioned out of Founder-led sales… you’re just doing it with appointment setters. Solidify your value proposition and validate your product and pricing with market willingness to buy out of the box. When you nail down the package your ICP is willing to pay your price for, have your sales team sell it on their own for 3 months solid. Then, start looking for a VP.
If you’ve got the sales team and process stable, how does that ARR hold up to scrutiny?
For your 20 to 40 customers, what do the NPS or CSAT scores look like? If every one of them is in the danger zone, you’re either headed for some big changes in product or you need to beef up support. Either way, a chunk of that ARR is due to churn soon. Nothing a Sales VP can do about any of that. Churning 20 to 40 customers sucks. You know what sucks much worse? Churning 20 to 40 customers repeatedly every quarter for the next year because you thought the answer to filling a leaky bucket was to turn up the water pressure.
Many people hire a VP of Sales before they’re actually ready because they think it’s a VP’s job to get them to this level of stability.
But, that’s not what a VP Sales does. What is the right JD for a VP Sales? Read on…
What is the early-stage VP Sales job description? (And more importantly, what is it not…)
Your VP of Sales will predominantly be responsible for winning new business. They can wireframe the basics of your Go to Market strategy. But, what they’re really great at is attracting and developing great sales talent and scaling efficient processes. Their expertise in training and accountability will give your company the foundation to scale from $Xm – $20m+ in ARR.
Here’s the VP of Sales job description in a nutshell:
- They are, by far, the best salesperson at your company.
Being an early-stage VP Sales means being involved in every important deal. Getting on the phone with clients. Prepping and post-morteming every interaction. Willing your company to hit every sales target you set in front of them. This isn’t a job where you hide behind spreadsheets and dashboards. Great VPs of Sales lead from the front. - Optimize your existing sales team and process.
A great VP dissects every aspect of your sales motion like a data scientist to identify the patterns that convert to revenue. They’ll analyze call recordings, scrutinize deal cycles, and fine-tune every touchpoint until every team member is shrinking their sales cycles and raising their conversion rates. The goal is uniformity and repetition to the point where the entire sales process from prospecting to close becomes muscle memory. When every deal follows a formula, your sales team gets better every time they run through it. - Attract and develop better sales talent.
The best VPs are people magnets with golden rolodexes and an eye for great sales talent. They have a reputation for making good salespeople great and great salespeople legends. Their pipeline reviews double as master classes in deal strategy. Their feedback is effective in countless applications. Their sales advice heals marriages. One year working for them changes the trajectory of a salesperson’s entire life. This is the coach that builds your championship team. - Build a replicable, scalable sales process.
Here’s where science meets art. Once they’ve found the limits of your existing sales process, and found every breaking point, they’ll build something better. They systematize the winning components, fill in the gaps, and replace the weak links. They’ll architect a sales motion that turns random wins into repeatable success. It’s not that they’re fixing what isn’t broken – it’s that they’re building a machine that can handle 10x the volume without losing efficiency. Every tweak, every new playbook, every process improvement comes from real data and battle-tested experience. - Create self-sustaining pipeline generation.
To have any deals to close, you’ve got to fill Top of Funnel with qualified opportunities. VPs know pipeline is the lifeblood of sales, and that quantity ain’t shit without quality. They’ll turn your team into a prospecting engine, teaching them how to prioritize based on probability to close, craft messaging that gets responses, and build enough quality pipeline to keep the wins coming. Sales teams that source their own deals create their own luck. And the right VP won’t let their team sit around and wait for Marketing to do it for them.
That’s the gig.
Did we miss something on your list? Bet you’ve actually got a CRO in mind.
We covered the two wrong VP hires most Founders make, but a third common mistake is not hiring a VP at all – and instead hiring what would have been a great CRO (had they needed a CRO).
You don’t need a CRO yet. You need a VP. So, let’s get crystal clear on the differences.
Here’s what a CRO does. If this list looks more like what you had in mind, you’re putting the cart before the horse.
CRO job description in a nutshell:
- Manage everything across the entire GTM stack.
The CRO’s purview is everything that touches revenue and the entire customer lifecycle. This includes upsells, cross-sells, and renewals. At some companies, it even includes Marketing. - Craft the Big Picture strategy.
The CRO is responsible for maximizing the business’s margins by meticulously balancing all the money details in product pricing, compensation, and quotas. - Build the systems that amplify all success metrics from Top of Funnel to CLV.
Every conversion rate that can be measured will be represented in a spreadsheet and data visualization once you appoint a CRO. And they’ll find a way to dial up every one of them.
A great CRO can take you from $20M – $50M in 2 years. But, you need a VP to get you to $20M first. Don’t make the mistake of thinking these two are interchangeable, with the same strengths and objectives, or that one person can do both. Your company needs the best VP in the VP seat and the best CRO in the CRO seat – and in that order.
Think you might have the right person in front of you? Let’s talk about how you interview a VP Sales.
How to interview a VP Sales to find the right one
Companies often spend $100K+ on exec search firms, invest hundreds of hours interviewing dozens of candidates to find their VP Sales. Yet the average tenure remains <1 year for a first time VP, 17 months across all VP Sales.
What gives?
Unfortunately, most interviews are useless at determining if someone is going to be successful at sales in your company. They’re snapshots of a moment in time that isn’t relevant to your situation. Every company is unique, so relying on past performance to predict future results in a poor recipe.
Also, sales leaders are uniquely difficult to interview. They are well-practiced at presentation, while most Founders are technical and struggle to assess the difference between confidence and BS. So instead, companies make the catastrophic mistake of relying on recommendations from their VC or fancy exec search firm, who will often push a far-too-senior, post-PMF hire onto a young startup that isn’t ready for that person.
The truth is: Being an early-stage VP Sales is brutally hard. Maybe the hardest job in all of tech, except for being a Founder. The best VPs do it once, maybe twice. Maybe. So anyone who has been an early stage VP more than twice is not your outlier performer. They may do post-PMF scaling, they may start their own business, they may become a VC… but they are definitely not joining your pre-PMF startup.
The VP who is going to come to your startup and turn it into a unicorn has not already done it somewhere else. That’s the hard, counterintuitive pill you have to swallow before you start this hunt. To find an outlier performer, you MUST go for someone unproven and take a bet.
So, if you can’t spot them by their credentials or perfectly planted interview questions, how do you figure out who you should hire? Don’t focus so much on the steps of the interview process or the questions to ask. Instead, focus on the outcomes you want. In other words, stop worrying about what to do or say, and think about what you want to learn about this person.
Here’s what you need to learn
To ensure the best possible chances of this person being the VP of Sales who puts your company on the map, make sure:
- They’ve sold at both mediocre companies and great ones.
Only exceptional sales people can sell a terrible product with minimal support, and proving success at a crappy company is the surest way to show that level of skill. Someone who knows how to take nothing and turn it into something… that’s the exact quality you need.But, for this person to take your company where you want it to go, they must have seen greatness too. They should also have sold at a company where things went right, so they have the ability to bring excellence to your organization as well. - They’re not a one-trick pony.
They’ve owned different parts of the sales stack. If they were once an SDR manager or Head of CS, and now they’re over Mid Market Sales, they know how to look at more than one function of GTM. Being able to look at more revenue streams than just New Business is a nice to have. Experience touching Top of Funnel is a necessity. You want a VP of Sales who understands how to build pipeline and create opportunities. - They come from a strong lineage.
You aren’t looking for someone who has already been a successful startup Sales VP, but you might want to look for someone who has worked for one. Sales is an apprenticeship career – you can only learn to be the best by working with the best. You don’t need a household name in your org at this point, but if you find someone who reported directly to a Tier 1 leader, you can bet excellence was instilled in them. - They’ve had the tough conversations.
A good indication that someone is capable of managing managers is they’ve done the dirty work of leadership already. They have experience firing people. Not what you expected to be searching for? It takes a lot of growing up to understand if the company fails, everyone loses their job. So, for everyone’s best interest, true leaders have to lead with accountability. This is imperative in Sales because missed revenue burns runway fast. - You really, really like them.
You have to be extremely close friends with your VP Sales. You have to trust them deeply. You have to really like working with them. If you’re super impressed with someone, but you don’t click, it’s not going to work out. We’ve never seen a successful SaaS startup where the VP of Sales and CEO weren’t thick as thieves. It doesn’t matter how good the VP is at everything else. This is a high-stakes relationship and you really have to love this person for it to work out.
You’re not looking at credentials, you’re looking at the DNA of who this person is. Technical roles require nice, neat checkboxes. Sales roles are about the human.
To find out who this person really is, you have to talk to the people who have worked with them.
Call references with purpose
These are the people who can tell you what this person is made of.
Every sales leader knows their best rep of all time. Call their old boss and ask,
“Your company is on fire and you’ve got one meeting with a prospect that can save it all. Who is the one person on the planet you’d call to close the deal?”
If the answer is your candidate, you’ve got the right one.
You need a magician who can turn nothing into something. The people they’ve worked with can tell you whether or not they’re capable of that. Doesn’t matter if they were an IC or a mid level manager. Magicians don’t fly under anyone’s radar. You should ask their teammates the same thing.
Ask their old boss:
“If you had 5 reps starting tomorrow, and could bring in any 1 person to coach this team up, who would you call?”
Again, you want to see if your candidate is regarded well for their ability to train others.
You’re looking for someone to mold a factory full of rockstars who will love working with them, be loyal to them, and crush quotas. Those skills don’t magically show up overnight. They’ve either been evident to everyone they’ve worked with, or they don’t exist.
The evidence of what they will do in the future is scattered around what they have done in the past. You just have to dig deep enough to find it.
The final thing you need to look for is the candidate’s unshakable faith in themself and their ability to figure it out. Any good Sales person will tell you that you have to have the confidence to win no matter what… because you’re going to fail over and over again in the process. And you can’t afford to let that get you down.
What you really want to know is: Do they really believe they have what it takes to be the VP who takes your startup to unicorn status?
And if you don’t want to take their word for it, we can introduce you to the candidates we know will get it done. Hire a Rockstar VP of Sales!
Brass Tacks
- Must have startup sales leadership experience
- Make sure you’re ready for a VP of Sales
- Don’t hire a CRO to be your VP
- Focus on the outcomes of the interview process
