I’ve founded a lot of startups, so I’ve had a lot of experience hiring VPs of Sales. I must have looked at well over 50k resumes and interviewed just about as many candidates.
I’ve made some smart decisions along the way – but I’m not going to pretend I’ve got a 100% success rate. I’ve made a ton of mistakes too.
Fortunately, that means I’ve learned a lot of actionable insights from all the things I got right and wrong. Here’s my advice on hiring a Sales VP, plus 13 tried-and-trusted questions to ask during the interview stage.
When Should You Hire a VP of Sales?
Before you get any deeper into this article, let’s pump the brakes and consider whether a VP of Sales is what you actually need.
You might think you need a VP when what you actually need is a Director of Sales or a Sales Manager.
Think about how big your sales team is going to grow in the next 12 to 18 months:
- If you’re a funded startup, absolutely hire a VP of sales. There’s no replacement for that experience; it’ll save you time down the road.
- If you’re a bootstrap startup, adding two salespeople every year, or you’re still trying to figure out product/market fit, maybe a Director of Sales is more applicable.
- If this is your first sales hire, you’ll want to hire more of a “doer,” like an SDR.
It might sound obvious, but the more senior and experienced a person is, the better they’ll be able to help you avoid mistakes, forecast results, and build effective processes – but they’ll also naturally be more hands-off.
If you need someone to make you money right now, that’s probably not a VP of Sales. The last thing you want is a hands-off sales leader, when you really need them to get their hands dirty in the first year when you’re just trying to figure it out.
I can definitely speak from experience here, albeit from a marketing perspective rather than sales.
I was hired as CMO at a pre-product/market fit company. That relationship lasted three months before we both realized: “This is stupid.” They had a bunch of stuff to figure out before I could even begin to add real value.
So my first key learning is: make sure you hire your VP of Sales at the right time for your business.
How to Approach a Potential Candidate
By this point, I’m assuming you’ve decided that a Sales VP is definitely right for you, right now.
In that case, you’ll want to start approaching candidates. They’ll fall into one of two categories:
- People who’ve applied for the role themselves
- People you’ve reached out to (in other words, headhunted)
You’ll need a different approach when speaking to those different types of candidate.
Approaching a Candidate Who Applied for Your Role
You’re automatically in a strong position here.
This candidate has applied for the role, so you know they’re interested in your company and are actively looking to work for you.
That makes this a beautifully simple conversation. Just reach out to them and arrange a time for your first-stage interview.
Approaching a Passive Candidate
Here, things get a little more difficult. You’re effectively doing cold outreach to these candidates. Admittedly, it’s not exactly the same – you’re paying them the compliment of saying you’d love to hire them, not trying to sell them something – but you still need to proceed with caution.
This person doesn’t know you’re going to contact them. You don’t know anything about their current situation, or whether they’re interested in a new role.
Get this wrong and you can piss off a lot of people. It’s easy to come across like they should be flattered by your approach. Whether or not that’s how you really feel, it’s definitely not how you want to come across.
In my experience, your best bet is to keep things super casual.
Send them a short, friendly email or LinkedIn InMail that briefly discusses the role and references what’s great about your company, then ask if they’d be interested in finding out more. Don’t call them – it’s too pushy, and they might be at work, which can make their life pretty awkward.
If they respond in the affirmative, great! Your next step should be to arrange a quick call – make it clear that this isn’t an interview. Instead, it’s a chance for you to sound one another out. Give more detail about the role, talk about your immediate and longer-term goals and how they fit in, and answer their questions.
By the end of that call, if you’re both on the same page, then you can plan a formal interview.
13 Interview Questions for Your VP of Sales Role
As I mentioned, I’ve interviewed a lot of potential VPs of Sales over the years, so I’ve picked up a few questions that I now rely on time and again.
One final point before I get to the questions:
Remember, this person is a potential VP, so you don’t have to make their life easy. Challenge them on their answers – especially if they don’t align with your vision for the future. A bit of friction among the senior team is often a good thing – you don’t just want someone who’ll nod their head at everything you say. Are they prepared to stick to their guns if you disagree?
1. How Big of a Sales Team Do You Think We Need Right Now?
You’re hiring a VP for their experience and strategic thinking, so they should have some idea about how big of a team they’d ideally be working with.
Get them to be specific. What would their ideal team look like? Do they want BDRs, SDRs, or Account Executives? Or a couple strong all-rounders?
2. Tell Me About the Teams You’ve Managed & How You Built Them
Presumably, your candidate has strong experience in managing and building teams. If they can’t talk through the processes they’ve followed in the past, that should set alarm bells ringing.
This question could lead to a ton of follow-ups. You might want to dive into the characteristics they look out for when hiring sales professionals, or push them for specific examples about their approach to recruitment.
3. How Should Our Sales & Marketing Functions Work Together?
Depending on your stage of growth, you might not have a marketing function yet. If you do, it might just be one or two people.
Regardless, you want to know that your candidate has a clear view of how sales and marketing should work together, both now and in future. Dig into their thoughts on lead generation and sales funnels, and the part played by each team.
4. How Should Sales and Client Success/Management Work Together?
From a similar perspective, you want to gauge your candidate’s understanding of the customer lifecycle.
Press them to get specific. You don’t want to talk theory here – ask them to make their answer relevant to your company and your future strategy.
5. How Do You Create a Winning Environment?
Being a VP of Sales isn’t just about hiring the right people at the right time – it’s also about getting the most out of those people. To do that, they need to build a high-performing culture.
They should have a clear vision for how they intend to do that, ideally backed up by real-world examples from their career.
6. What Sales Tools Have You Used in Previous Roles?
While VP of Sales is a largely hands-off role, you still want your candidate to have a strong understanding of the tech stack and the practicalities of doing the job.
As a startup, there’s a good chance you won’t have built your whole tech stack yet. Even if you have, it’s probably not set in stone. You’ll likely want to hear their recommendations on tools to invest in and processes to implement to drive efficiencies and improve performance.
7. What Will Our Sales Function Look Like Six Months After We Hire You?
You want the successful candidate to come in and hit the ground running; you certainly don’t want to spend days or weeks telling them what they should be doing next.
Even though this is just the interview stage, they should have a rough idea of the strategy they’d implement if they got the job, and what medium-term goals they’d be working toward. Dig into these goals, and see how they align with your own.
Bear in mind that this could be a broad answer – in fact, it could arguably form the bulk of the interview. It’s useful to hear which aspects they focus on the most – is it the size of the sales team? The culture? The tech stack? Or a metric like leads or revenue?
8. How Would You Go About Setting Quotas?
Early in your company’s growth journey, you likely don’t have a ton of data, which can make quota-setting a difficult task.
How would they go about establishing team-level goals, and breaking those down across individual salespeople?
9. Who in Your Network Would You Want to Join Our Sales Team?
Any prospective VP of Sales should have built up a little black book of high-quality, high-performing salespeople.
You don’t necessarily need a list of names at this point – it’s unlikely to mean much to you. But some detail about their background and why your candidate would hire them will definitely be helpful.
10. How Do You Overcome Fear, Uncertainty & Doubt in Prospects?
Especially if you’re an early-stage startup with a new, unknown product, you might face a lot of skepticism from prospects. They might be reluctant to put their faith – and budget – in a relatively unproven brand.
Your VP of Sales should have a strategy in place to overcome this doubt. Ideally, they’ll have worked in startups, or with brand new products, in the past – so they’ll be speaking from experience.
11. Talk Through a Typical Working Day for a VP of Sales
You’re a founder. You’re probably not a salesperson, and you may not have worked closely with a VP of Sales in the past, so you’re likely not the best person to give them specific tasks.
You need your candidate to take the lead here. How would they structure a regular day? What would they focus on? And how would their priorities shift over time, as your company grows?
12. Describe the Rep Who You Found Most Difficult to Manage
Anyone who’s managed people in the past will know it’s not always easy. But you often end up learning more from your most challenging direct reports than from those who just come in and get the job done every day.
Find out why that particular candidate was so difficult to work with. Was it a performance-related issue? Or was it more about culture and behaviors?
Importantly, you also want to find out what they learned from managing that particular salesperson, and the actions they took at the time.
13. How Will We Beat Our Competitors?
This question is about more than just reeling off your product’s key features and benefits. It’s about digging into their strategy for overcoming the competition in the long run, and the specific tactics they’re planning to use.
It’s also useful to find out who they think your competitors are. This can tell you a lot about how they see your company and product.