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This Is How Founders Fail When Hiring Their First VP of Sales

Massive stakes. Hypercompetitive market. Easy to get wrong.

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“If you build it, they will come” might work for Kevin Costner in Field of Dreams, but it doesn’t work in SaaS. Without a proper go-to-market strategy, even the best products are forgotten as well-funded competitors funnel millions into marketing campaigns.

Chalirmpoj Pimpisarn | EyeEm | Getty Images

For founders of enterprise SaaS startups, it’s easy to screw up hiring a vice-president of sales. Instead of stumbling down a dark path, learn from the common pitfalls we’ve seen hundreds of teams experience as they hire, scale and bring their products to market.

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Bad timing.

Timing your first VP of sales hire is a balancing act. If you’re too late, you’ll drown in a swamp of bad data and rogue processes. If you’re too early, your VP will go on a hiring spree.

You’re ready to hire your first VP of sales when you have:

  • 2-4 sales or business development representatives (SDRs/BDRs) who spend their time looking for prospective clients
  • 2-6 sales representatives in place, who spend their time closing prospects sourced by the SDR/BDRs
  • $1-2M+ in ARR, proving your product-market fit

Wrong type of superpower.

The easiest way to find the wrong VP of sales is to look for them. No matter how great a sales leader has been at another company, he or she may not be the right candidate for you.

This is easier said than done. For practical matters, CEOs of early stage businesses must have a sales VP who speaks the same business language -- or shares the same “superpower” as the CEO. Bigger companies, however, may have a CRO or sales operations leader who can act as a translator between the two, making sure they’re always on the same page.

Generally, sales leaders have at least one of four sales superpowers:

  1. Company management. These sales leaders can clearly demonstrate strategic thinking backed by data.
  2. Process management. Process managers love lists and planning documents. They dream in Quip docs.
  3. Culture management. Vocal with big personalities, these sales leaders can have an outsized impact on any organization as a whole.
  4. Deal management. Deal managers are addicted to sales. They automatically memorize every detail about deals in their pipeline.

Optimize for the sales leader whose sales superpower aligns with your CEO. When a sales head and CEO speak different business languages -- one prefers data-backed strategy, the other focuses on company culture -- the partnership is doomed from the start.

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Ineffective recruiting.

Start by reaching out to your network, asking for references that fit your specific ideal VP of sales’ communication style and background. Avoid asking for “any good salespeople.” The last thing you want to do is waste a qualified candidate’s time if their particular strengths aren’t a good fit.

As part of your interview process, you can and should be digging deeper into a candidate’s background. As you consider people with the right strengths, consider their specific experience, salesmanship style, ability to executive and emotional intelligence.

Making the offer too early.

Once you’ve decided you like a candidate, your immediate impulse might be to email an offer letter and comp package -- and hope they accept. That might work, but there are more effective ways to close a candidate. Just because you’re ready to move forward doesn’t mean they are.

Does the candidate have a significant other? Offer to take them both out to dinner, even if they’ve already accepted your offer. Get to know them. Your candidate’s employment affects their entire family, and convincing their significant other that the opportunity is worthwhile will significantly increase the candidate’s likelihood of staying in the job for years to come.

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And lastly, ask the candidate in person if they’re ready to accept the offer. Interviews are two-way streets, and your candidate might still have lingering questions that you can address.

A great sales VP is worth his or her weight in gold. Click through to read the full Founder’s Guide to Hiring your First VP of Sales from Emergence Capital.

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