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How to Evaluate a Sales VP Role Before You Accept

16 Min
How to Evaluate a Sales VP Role Before You Accept

You open the email. After reading the pleasantries, you get to the meat and potatoes of the message: “How would you like to be a VP of Sales with us?”

Your heart skips a beat. You’ve worked your entire sales career to reach this point and now it’s right there, at arm’s length.

You feel like the only answer you can give is a resounding “Yes!” But hold your horses for a bit. We hate to be the bearer of bad news, yet someone needs to be the voice of reason.

While outright accepting a Sales VP role is tempting, there’s a lot you need to evaluate before you jump in.

VP of Sales is a tremendously responsible role. Not to mention the long hours, stress, traveling around – it’s not a decision you should be taking lightly.

Don’t get us wrong – we’re not trying to convince you not to take the job. We’re merely here to show you how to evaluate a Sales VP role before you accept it. In this article:

  • Understanding your role
  • Red flags to look out for
    • Health of the pipeline
    • Ask about the sales process
    • Ask about the budget
    • Ask about growth plans
    • Ask about your predecessor
  • Understanding the founder’s vision

Understanding Your Role

Vice president of Sales is one of the most important roles in a company. It’s a top-level executive position which deals with the sales team and directly affects the lifeblood of the company – revenue.

A VP of Sales needs to have excellent interpersonal communication, time management, leadership, and persuasion skills. Since they both lead the team and directly deal with some clients, they need to have a diverse set of skills.

VP of Sales are both responsible for nurturing relationships with current clients, and finding new opportunities to grow.

They’re the ones who set the goals and targets for the sales teams. Hence, they’re also the ones who oversee achieving those goals.

Oftentimes, Sales VPs are the bridge between Sales and Marketing. They work closely with the marketing department on making sure campaigns hit the mark.

They’re also the ones who draw most of the reports, which can be tiring and time-consuming. This is why it’s crucial for them to have a good grasp on the different sales metrics and activities. Sales leaders often have to deal with huge amounts of data.

MoData - Current Pipeline

While being a VP of Sales can be awesome, it also comes with a ton of responsibility, pressure, and expectations. You’re directly responsible for growing the organization and leading your team to victory. Every good and every bad quarter falls on your shoulders.

Now that we have a better understanding of the role, let’s see how you can evaluate it.

Red Flags to Look Out For

If you’re reading this article, then this is likely your first position as a VP of sales. Being a sales leader is a tremendous responsibility so you need to think long and hard before you agree to take on the role.

While you can’t be certain about everything that goes on beneath the surface, there are some definite red flags to look out for.

Before you accept the role, you need to understand details around the organization and pipeline. Dig into things like:

Health of the pipeline

This is one of the most common pitfalls for new sales leaders. When they offer you the role, founders might tell you something like, “We have 10 millions in pipeline”. They would usually focus on the size and potential value of the pipeline, while ignoring other metrics.

They’d skip out the average sales cycle is 30 days and most of the deals in the pipeline have been sitting there for over 90 days. They wouldn’t be doing it out of malice. Founders are rarely that deep into data and metrics. Which is exactly why you should be.

You need to evaluate the pipeline for yourself and you need to do it before you accept the role. Otherwise, you might be walking into a minefield of unrealistic expectations and responsibilities.

Dig into the data. Check out how it’s being recorded and whether you can trust the numbers. Having a pipeline management tool like MoData can definitely help make this process a lot easier.

Ask about the sales process

Is there an established sales process?

Is there a developed playbook or would you be developing it from scratch?

These are important questions to answer before you take on the mantle of Sales VP. Many first-time VPs are used to working with already established processes. Creating something from scratch requires a whole different skill set.

This shouldn’t be a deterrent. Doing things you’ve never done before is how you grow, but you need to know about it beforehand. Preparation is half the battle.

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Ask about the budget

If you’re going to grow the organization, you’re going to need a budget to do it. Growing the org without a proper budget is like climbing a mountain without equipment – it’s technically possible, but most who attempt it don’t make it far.

Budget could be one of your greatest limitations. Hence, it should be one of the first things you ask about. The size of your team, the tools you use, the resources you’ll have – everything will hinge on the budget.

Ask about growth plans

What are the goals you’ll be trying to achieve and are there any growth plans to get there? Are these goals and plans realistic?

These are important questions. You don’t want to work at an organization that expects you to plant magic beans and grow a beanstalk sky high, yet not grow the team in the process.

If you can’t hire people, you can’t scale, and you can’t grow, then why would you take the job in the first place?

Equally as concerning is the complete lack of growth plans. This means the goals and direction aren’t clear at all. You’d be asked to navigate a ship in the mist without a clue where you’re going and how to get there. And the worst part is, you won’t know it even if you’ve arrived.

How are you going to measure your success or failure without clear goals? This is not a good position to be in, so make sure you clear out the growth plans beforehand.

Ask about your predecessors (if there were any)

Odds are if you’re a first-time VP of Sales, you’re going to face a whole set of challenges you’ve never encountered before. This goes double if you’re the org’s first VP of Sales.

If the sales process has been founder-led so far, your approach will be very different than it would be if there’s been another VP of Sales before you.

So you need to know if you’re the first or not. If there has been someone else at this position before you, you need to ask questions like:

  • What happened to your predecessor?
  • Why did they leave their role or why were they removed?
  • What did they do wrong?
  • What did they do right?

Talking about this will give you a wealth of information. It might also point to some other red flags.

Understanding the Founder’s Vision

As a VP of Sales, you would wield tremendous power. But you’d still have a boss – the founder. Even if they don’t micromanage you, you’d still be limited by their vision. You need to make sure you’re not walking into a role where they ask you to work blindfolded and with hands tied behind your back.

When your ideas and the founder’s misalign, there’s going to be lots of pushback all over the place. This will prevent you from hitting your targets and achieving your goals, so make sure you iron these things out before you even step into the role.

Ask them about their ideal play and how they think the org should operate. Generally speaking, founders have a huge pull on the sales process. If you think their philosophy of sales will hinder your work, you should know about it beforehand.

For example, you may want to hire more SDRs and scale the team. They might think a better approach would be to hire high-end solutions people to do the selling and prospecting.

Things could get even more extreme. Some founders have a very clear vision about how they want their organization to run. As a result, they often ignore best practices and would disregard your input.

An example would be a policy of not calling people. This would tie your hands, yet you’d still need to get results. Can you still do it? You need to be very clear with yourself about it. And you can’t do that if you don’t know everything about the founder’s vision.

Another aspect you need to look into is how much freedom would you have to run your sales team? Being micromanaged by the founder is a huge reason why many VPs of Sales fail. If you don’t have the freedom to run your team, track the numbers, and pursue leads as you see fit, then will you be able to do your job? This is not a trivial question.

These aren’t easy conversations to have, but they will help you get a better understanding of the org. Usually, when someone offers to make you a VP of Sales, they’d try to “sell you” into the role (whether they’re the founder or a recruiter). It’s your responsibility to evaluate everything before you accept.


Being a VP of Sales can be very rewarding, but also very challenging. There are some considerations you need to make before you jump into the role.

Most importantly, you need to make sure whether your vision and the founder’s align and to learn what’s expected of you. Once you know that, it’s a lot easier to make a decision. Trust in the numbers. Data never lies.

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