You’ve worked hard, and your startup is growing.
You may have just scored a big round of funding.
EVERYONE around is saying it’s time to hire your first VP of Sales.
Yet this is a hire the majority of Founders I talk to get wrong — sometimes multiple times.
So I’m here to help.
This is the work my company does every. single. day. We help Founders get their VP of Sales hire right the first time around. And these are the conversations I have behind the scenes.
Real talk: no Founder wants to hire the wrong VP of Sales for their startup.
Doing so can set your business back six months or more. And this potentially six-figure mistake could also jeopardize your buyer journey and customer experience.
Even worse? A mis-hire here may disrupt your entire team (in a bad way).
I detailed all these downsides in my guide on What Happens When You F-Up Your VP of Sales Hire and How to Turn Things Around.
But despite all those significant issues, Founders still aren’t getting it.
So the question becomes, why do Founders keep banging their heads against the wall and expecting different outcomes? Are they gluttons for punishment?
Or are they obsessed with failing, hoping to rise from the ashes and organize a triumphant comeback when they’ve learned from their mistakes?
Okay, some of these questions may be a stretch.
But seriously, what gives?
I know five common reasons that the first VP of Sales hire doesn’t usually work out. And you should too!
That’s why I’m shining a light on them in this guide.
I’ll also show you how to avoid a mis-hire to protect your company from the repercussions of having to go back to the drawing board.
Keep reading, and you may be one of the very few who actually gets this first hire right.
Hiring Your First VP of Sales: Why It Doesn’t Usually Work Out (And How to Avoid This)
Here are the top five reasons why the first VP of Sales in a startup doesn’t tend to stick around:
1. Founders Succumb To Shiny Object Syndrome
I shared a story for an OpenView article, How to Hire the Right VP of Sales for Your Startup, that sums up my first point perfectly:
We recently worked with a startup that was unfortunately on their 2nd VP of Sales mis-hire in three years. As we asked them probing questions about what their hiring process looked like, they told us that they went off a gut decision based on behavioral questions and a 30/60/90 presentation.
A gut feeling and a presentation? For real?
A presentation is just one example of a shiny object that can attract your attention and blind you during the interview process.
It’s so easy to slay a presentation and woo Founders — especially for sales gurus.
But this doesn’t give you any insight into how this person will handle the job you need done.
So as I mentioned in that guide, it’s time to ditch the 30/60/90 presentation. And while you’re at it, get rid of these other shiny objects that can distract Founders during the hiring process:
- Long tenures. There’s no guarantee that this person will last as long at your company if the work isn’t the right fit for both parties.
- Insane results. It’s difficult to take what works well in one business and replicate it to a T to earn those same explosive results for your business.
- Huge personalities. The biggest distraction of all is someone with a great personality who knows how to work the room and answers every question “perfectly.”
Don’t worry, I’ll show you how to avoid these shiny objects later. There are still more reasons why hiring a VP of Sales often fails on the first try.
2. Founders Hire for the Future, Not for the Present
In the guide mentioned earlier on How to Turn Things Around if You’ve Hired the Wrong VP of Sales, I also discussed how you shouldn’t be hiring for your 10-year plan.
While it’s smart to look ahead, if you hire someone to tackle your long-term goals, but they can’t handle the problems you have right now, they’ll never make it to your future plans (your business may not either).
That’s why it’s crucial to hire for the work you need accomplished now.
You also need to understand the VP of Sales’ superpowers (more on this later) and how each one can help your business in different ways.
This is essential because you don’t want to hire someone who’s fantastic in an area you don’t actually need help with.
I often see Founders hiring for future superpowers instead of current ones. Then they end up having to quickly churn through their first VP of Sales because their new hire can’t solve the problems at hand.
So you should spend time figuring out what your company needs now and what type of skills/experience that takes before you even begin the hiring process.
We’ll talk more about this later.
3. Unrealistic Expectations on Both Sides
When Founders and job candidates are unrealistic about what they want/need versus what they’re signing up for, you’ll have a rocky road ahead.
This might manifest as a Founder who’s hoping their new VP of Sales will magically transform their dire situation, as mentioned in this guide. Or it could be a job candidate who gets swept up in the salary and employee perks but doesn’t actually realize the work involved in the position.
As a Founder, you need to be crystal clear about:
- Your place in the market
- Your products
- What you’re offering
- What you can deliver
- What you want to achieve
- The real work that needs to get done
Once you get realistic about what you really need, you can find a candidate who checks those boxes (and more!). You can also suss out people who are more focused on their own wants and not your company’s needs.
4. Founders Follow Bad Advice
If you read that guide I mentioned a moment ago, you know sometimes Founders just get the wrong intel.
General startup advice doesn’t take into account your specific needs and problems. It can’t because whoever’s offering that advice doesn’t know your unique business.
For example, let’s say you hear that a process-focused VP of Sales can help catapult your startup. So you decide to follow through on that advice even though that’s not an area in which your business is struggling.
You could mess up a really good thing by bringing this person in. And you probably won’t solve the problems you desperately need help with.
So before you take general advice, especially when it comes to hiring your first VP of Sales, you must consider your situation, what you need now, and how this information could but may not apply to your business.
5. Founders Fall for Referrals Who Don’t Work Out
Along the same lines as following bad advice, I often see Founders getting sucked into using referrals, whether from their Board of Directors or investors, which is another big mistake.
Hey, we get it. You may be under pressure and constantly hearing how great this person is and how they may be able to help turn things around. You want to keep everyone happy, and this person may be capable.
It’s a tempting scenario.
But I’d strongly caution against hiring a referral.
They rarely work out unless you can validate that they really have the skills you need in this stage of your business.
You shouldn’t be afraid to politely decline the offer. As the Founder, you have a voice, and you’re entitled to push back when necessary.
Otherwise, you could be in hot water a few weeks later, despite knowing all along that this wasn’t the right fit.
So now that you know the five most common reasons why many first-time VP of Sales hires don’t work out, let’s talk about how to avoid that from happening and choose the right candidate from the start.
How To Tell If Your First VP of Sales is Right for Your Startup
Here’s a simple, proven three-step formula that’s helped our clients find the right VP of Sales for their startup on the first try:
Step 1: Think Before Getting Caught Up in the Hype
Before you even think about looking for a VP of Sales, it’s imperative to get super clear about what you need, why you need it, and how you plan to reach your goals.
This high-level overview of what the position will actually entail helps you laser-focus on candidates who truly fit the bill.
This is an often overlooked step that costs Founders exponentially in mis-hires, so don’t skip it, as tempting as it may be.
So what’s the superpower your team’s missing the most right now?
There are four VP of Sales superpowers:
- Deal management
- Process management
- Company management
- Culture management
Your goal in this step is to identify where you need help the most and find someone who has experience crushing that specific category.
For example, if your process needs some help, you need a VP who excels at process management. And if you’re having trouble getting your team to close big deals, a VP who specializes in deal management may be better suited for you.
Of course, candidates will probably have skills overlapping in other categories, but don’t let that distract you. You’re looking for someone who excels at fixing one specific, giant problem that’s preventing you from reaching your immediate goals.
Nailing down these specifics beforehand will also ensure that you don’t get distracted by shiny objects like a stellar interview or a solid 30/60/90 presentation.
So whether you have an idea of what’s missing or not, it’s always helpful to journal your thoughts. Get these out of your head and on paper to really see what’s going on. You may be quickly surprised by what you uncover.
Step 2: Take an External Perspective To Address Internal Areas for Improvement (i.e., Ditch the Theory and Embrace the Data)
As the headline of this section suggests, you gotta throw out the one-size-fits-all startup advice. You can’t obsess on theories so much that you miss what’s actually going on in front of you.
So tune out the external noise and truly listen to what your business is trying to tell you.
You should know your business better than anyone else. And that means you’re the most capable person to hear what it’s saying and its (maybe not so) subtle cries for help.
However, sometimes this is easier said than done.
You have to be face-deep in your operations and high-level strategies while also taking an outside perspective.
So let’s put it this way…
Imagine this wasn’t your business, but a good friend’s. If they asked for your advice, what would you tell them?
Before you can give them an intelligent, actionable answer, you’d probably want to take a deep dive into what’s actually going on, getting as close to the work and the data as possible.
Then you’d be able to develop a plan that addresses what’s working and what needs improvement. You’d probably recommend hiring a person with X, Y, and Z skills and expertise to make progress in those struggling areas.
So why can’t Founders do this for their own startups?
Because many get so caught in the weeds during the research phase that they become overwhelmed or decide to just fix things themselves.
But that’s not the goal; the aim is to find someone who would do a better job at the tasks and areas you identified as needing work.
Use this same external lens internally, and you’ll have a much easier time picturing the type of candidate best suited for your VP of Sales role.
Step 3: Always Use a Hiring Scorecard (or Find an Expert Who Does)
Once you know what you need in your ideal VP of Sales candidate, you can add these must-haves to your hiring scorecard. Then you’ll instantly know whether candidates are the right fit for your startup.
Not familiar with a hiring scorecard? Big mistake!
A hiring scorecard is a handy tool that creates an unbiased system for you to evaluate candidates based on a set of standards and qualifications your startup needs.
Imagine you’re a judge at the Olympics. Your role is to evaluate each athlete’s performance in a particular category, ranking them with a numbered system before a final tally reveals the highest score.
That’s basically what a hiring scorecard does.
You’ll create categories based on what you’re looking for, then grade how well each candidate’s skills and experience match up during their interview.
You’ll then compare these scores across the board with other candidates to see who surfaces as the winner.
Hiring scorecards are effective because they prevent shiny object syndrome from blinding you to less-than-perfect candidates. They allow you to really see how candidates rank and compare to what you’re looking for, so you can hire the best fit for the problems at hand.
As a result, hiring scorecards help slash the time it takes to hire and your churn rate. Who wouldn’t want those perks?
But as you probably know, creating an effective tool doesn’t usually happen in an overnight rush job. Sloppily throw together an imperfect hiring scorecard, and you’ll be in the same position as most Founders: heading back to the drawing board for a second VP of Sales hire.
Instead, it’s crucial to take your time here and really get your thoughts out on paper, including what you really need and where you’re struggling.
Since there’s a lot of planning that goes into creating the perfect hiring scorecard, I’ll send you to our hiring scorecard guide next. You’ll find an excellent example of what one looks like to follow before creating your own.
You can also check out my guide on The Top 16 Traits a Successful VP of Sales for a Startup Should Have for more help on potential categories to add to your scorecard.
Now, if this sounds like a daunting, time-consuming task, or you’d rather focus on other areas of your business (we don’t blame you there!), our expert recruiting firm can help.
And, before you say anything, we cringe at the word recruiter too.
Sales recruiting is totally cringe-worthy.
It evokes that eye roll and deep “ugh” feelings in most of us.
But if that’s what you think of when you hear the word recruiter, you’re working with the wrong team.
Other teams are likely to send you dozens of candidates as fast as possible in the hopes that someone pans out. But you’ll probably wind up with a stack of dud candidates who probably shouldn’t have been sent your way in the first place.
So a better approach is to find an executive recruiting firm that’s aligned with you, your startup, and the work that needs to be done at your stage. One that’s focused on building your team and your business while making sure your brand is well represented in the marketplace while leaning into candidate experience.
You also want a team that specializes in what you need instead of being a general recruiter.
Fortunately, you don’t have to go too far since that’s exactly how my team and I approach relationships with our clients. We’re hyper-focused on helping you hire the right sales leaders for your SaaS startup.
And we’ll get your VP of Sales right the first time to save you from the expense, stress, and hassle of making a mis-hire.
Learn more about how we do that by peeking into our processes, or get in touch now to tell us about your business!
Final Thoughts on Hiring Your First VP of Sales for Your Startup
The cold hard truth is that many startups burn through their first VP of Sales for a number of different reasons, as you saw earlier in this guide.
In the event you need more social proof as to why this all matters, I teamed up with Pablo Dominguez from Insight Partners talk about this out loud. The full replay can be found here… just give it a minute to buffer (downside of LinkedIn Live).
But that shouldn’t be a badge of honor or an experience every startup needs to go through. And since you’re reading this, you’re well ahead of the rest of the pack and may be able to avoid making a costly mis-hire mistake.
So go out there and put the tips we shared today to good use! You’ll land the right VP of Sales the first time, and you’ll be grateful you took the time to do it right.
You can also partner with the right firm and let them do the heavy lifting for you. Never fear, we’re here to take this crucial task off your overflowing to-do list. Our hotline is on with an ear to listen and a mind to brainstorm if you need it!