Hiring an effective, capable sales team is one of the most important things you can do for your growing company, and choosing the right candidate to lead your sales organization is critical to the success of your startup.

  1. When to hire a VP of Sales
  2. Who to hire
  3. What a VP of Sales does
  4. Responsibilities of a VP of Sales
  5. How to Hire a VP of Sales
  6. Interview questions

When to Hire a VP of Sales

As founder, you are your company’s first salesperson. But as your startup gains traction, you need to focus on strategizing — not prospecting and closing deals.

That doesn’t mean your first hire should be a VP of Sales. If you’re looking for someone to run front-line sales for you, it’s probably best to bring a salesperson or sales manager on board. They’re far less expensive than a VP, and they won’t be reluctant to get their hands dirty and bring in revenue the way a high-level hire might.

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In fact, your VP should not be directly closing any deals but the Big Kahuna ones. I’ll explain why in the next section.

But let's assume it’s been approximately 24 months since you founded the company. You’ve got one or two sellers, product-market fit, and a somewhat repeatable sales process. Now you’re ready for a VP.

Who to Hire for a VP of Sales

A startup VP of Sales should look much, much different than the VP of an established company. In your organization’s first lifestage, every day is a battle. The startup VP of sales need to convince prospects to take a chance on an untested product and unknown vendor. She’s figuring out how everything works. This VP quintuples or even 10Xs your revenue.

Once your company is mature, your VP’s job is to manage managers of managers. She’s much more of a dashboards thinker.

Keep this distinction in mind when you’re reaching out to candidates. Many founders are attracted to big names from well-known companies (especially because these VPs will bring a stacked Rolodex with them). However, if a VP’s strategy, mindset, and contacts are better suited to a big company, you’ll likely end up parting ways quickly — and that can spell major disaster for a young organization.

In fact, your VP doesn’t even need to be a VP at their current company. An ambitious, creative, hardworking manager who’s excited to jump in and build your business with you might be perfect.

Now that we understand what a VP of Sales does, let's review the key responsibilities of the role.

Responsibilities of a VP of Sales

Jason Lemkin, VC and former CEO of EchoSign, explains a startup’s VP of Sales has five primary responsibilities, from most important to least:

  1. Recruiting
  2. Advising reps on their current deals
  3. Optimizing the sales process and tactics
  4. Defining strategy
  5. Closing business

One-fifth of the VP’s time — in other words, an entire day of their work-week — goes to searching for potential hires on LinkedIn, taking recruits to coffee, asking their network for leads, interviewing, and hiring. To scale, you’ll need lots of human-power. Your VP needs to acquire it for you.

Their second function is helping their reps win business. That means reviewing their pipelines, pointing out obstacles, identifying opportunities, etc.

In third place, the VP should be tweaking the sales process: Creating sales scripts, email templates, and reusable demo agendas; perfecting the stages of the sales process; understanding which features speak to which prospects; writing the product roadmap with Engineering, and more.

Next, the VP must focus on the big picture. How can the company upsell and cross-sell its existing customers? Which verticals or industries should it target next? What’s the most effective way to spend the company’s budget?

And in very last place, meaning it should demand the smallest amount of their time, attention, and resources: Closing deals. If you're trying to land a whale, yes, it might be a good idea for your VP to jump in the car with you and meet with the prospect.

Lemkin says the VP can even (sometimes) take on a quota in the beginning. Yet they should never be closing more than a fraction of your deals, because it's simply more important for them to hire and train sellers than sell themselves. You know what they say about teaching a man to fish.

How to Hire a VP of Sales

If you’re ready to hire your first VP of Sales, here’s a sample job description to get you started.

Depending on your budget, you may want to use a recruiter. Yes, finding and reaching out to candidates can be incredibly time-consuming — but that’s not the main reason to use a third party.

Because salespeople are so skilled at selling, it can be tough to figure out who’s the real deal and who’s just good at B.S. In addition, recruiters usually have a much bigger network than founders. You’ll get exposure to candidates you might have never found on your own.

Whether you choose to facilitate the hiring process yourself, or use a recruiter, the same interview process applies.

  1. Reach out to potential fits (via a recruiter or yourself); optionally, let your network know you’re hiring
  2. Review applications
  3. Schedule short phone calls with promising candidates to screen them for interest (recruiter or you)
  4. Meet in-person with candidates who passed phone screen (you)
  5. Meet again with candidates who did well in previous interview; have them talk to several members of the team (you)
  6. Follow up with remaining candidates to determine interest (recruiter or you)
  7. Ask shortlist of candidates for references (recruiter or you)
  8. Extend job offer to top candidate; if they say no, send job offer to second-place candidate, etc. (probably you)

VP of Sales Interview Questions

These questions span from technical and operational to cultural. Adapt them to your company, product, and the candidate.

  • Which tools are in your sales stack?
  • What do you think about them?
  • Did you choose them, or did you inherit some or all of them?
  • If you could build a sales stack from scratch, which tools would you choose?
  • What metrics do you check every day, week, month, and quarter? Why?
  • How do those numbers guide your decisions?
  • Hasa strategic shift ever changed which metrics you pay attention to because? Explain.
  • How do you work with other departments in your current job?
  • What works? What doesn’t?
  • Have you experienced any challenges working with Marketing? If so, how did you tackle them?
  • Have you experienced any challenges working with Support and/or Services? If so, how did you tackle them?
  • What have been your ASPs in each of your previous roles?
  • What motivates our buyers to purchase?
  • How would you approach recruiting and hiring for your initial team?
  • Roughly how many salespeople do you think we need right now?
  • Approximately how much of your time would you devote to recruiting in this role? (Alternatively, “How much of your time did you devote to recruiting as [title] for [employer]?)
  • How have you successfully managed to retain your best salespeople?
  • How did you create a high-performance culture at [company]?
  • How [did you, would you] encourage healthy competition?
  • What are the best non-monetary ways to recognize performance?
  • Have you experimented with sales compensation? Were any of those experiments successful? Failures? What did you learn?
  • What you would accomplish in your first four months? Six? A year?
  • I’ll level with you: This job will be tough. [Insert description here, e.g. We’re a small, lean team, operating with few resources and working long hours.) Are you up for that?

Try to be as patient and methodical as possible to avoid hiring someone just because they look good on paper or you need a warm body. The wrong VP of Sales can cripple your startup’s trajectory and burn valuable cash. The right VP of Sales can double your revenue in half a year.

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Originally published Nov 21, 2019 7:30:00 AM, updated November 21 2019

Topics:

Sales Hiring