A common pitfall for many founders is hiring a Vice President of Sales who possesses numerous strengths—intelligence, polish, and a stellar resume from a reputable company—but lacks genuine prowess in direct selling. These leaders can articulate quota attainment, sales operations, and scaling strategies, often brimming with ideas on process optimization. Yet, when it comes to the fundamental act of selling, they fall short. This oversight can be detrimental, especially for startups aiming for rapid growth.

The Best Sales Leaders Were Once Top Salespeople

Empirical evidence suggests that the most effective VPs of Sales were once strong individual contributors in their early careers. While not always the absolute top salesperson, they consistently ranked in the top 20% or higher. This foundational experience provides an invaluable understanding of the sales process from the ground up.

You might wonder how seasoned VP of Sales candidates could lack strong selling skills. The answer lies in the vastly different sales environments of large, established tech companies versus agile startups.

Startup Sales vs. Big Tech Sales: A Crucial Distinction

In large, well-established companies with strong brands and deep market penetration, "sales" often operates more like a finely tuned machine. When a product is universally recognized and every potential client is already an "opportunity," the sales role shifts. It becomes more about optimizing existing processes, tweaking systems, and managing a pipeline that often comes to you. In such environments, it's possible to rise to a Director or even VP level without personally building a team, winning tough competitive deals, or frequently visiting clients—they might simply come to an Executive Briefing Center.

However, startups, even those in later stages, bear little resemblance to Fortune 500 giants or established tech companies in their sales approach. Most startups seek sales leaders to build and scale teams from 5 to 10, then to 30, 100, and beyond. This requires a hands-on leader who can not only strategize but also demonstrate and execute effective selling.

You simply cannot afford to accidentally hire a polished sales leader who can't sell, regardless of how impressive their LinkedIn profile appears. For more insights on this, consider reading "If Your VP Sales Isn't Going to Work Out, You'll Know in 30 Days."

Why a VP of Sales Lacking Direct Selling Skills Fails Startups

Hiring a VP of Sales who isn't a great salesperson themselves almost invariably leads to failure for several key reasons:

  • Lack of Respect from Top Performers: Top salespeople instinctively recognize a great sales leader. If a VP of Sales lacks genuine selling ability, they won't command the respect of their team, and high-performing reps may even refuse to join or stay with the company. This often results in the VP recruiting a team of equally mediocre salespeople.
  • Poor Product Understanding: VPs of Sales who don't actively sell rarely develop a deep, intuitive understanding of the product. While this might be acceptable in massive, established companies, it's a critical handicap in a startup where product nuances and value proposition are constantly evolving and need to be articulated compellingly.
  • Inability to Recruit Top Talent: Leaders can only recruit what they truly understand and excel at. A mediocre salesperson promoted to a management role will likely hire mediocre sales representatives. They simply can't attract or effectively evaluate top talent because they don't possess those skills themselves. Moreover, they may hire reps who also struggle to grasp the product's core value.
  • Struggling in Competitive Environments: Startups often operate in highly competitive, agile markets. Sales leaders must know how to win tough deals against better-funded or more feature-rich competitors. Big company sales leaders who aren't strong individual salespeople tend to wilt under this pressure, as the competitive dynamics are fundamentally different from those in established markets.
  • Failure to Diagnose and Solve Sales Problems: Great sales leaders, those with strong selling backgrounds, can quickly identify the root causes of sales issues and implement effective solutions. Those without this hands-on experience often struggle to diagnose problems, instead blaming external factors like marketing, the CEO, or the product itself.

To become a successful VP of Sales, one must truly work their way up, starting as a top-quartile individual contributor. Be cautious of candidates whose management experience is solely from very large, stagnant, or non-competitive companies; they may possess many valuable skills, but direct selling prowess might not be among them.

How to Identify a Truly Great VP of Sales Candidate

If you're unsure whether a VP of Sales candidate possesses the necessary selling skills, here are five crucial tips:

  • Ask for Customer References: Request three customer references and call them. Inquire specifically about how the candidate helped their customers. Their ability to sell will become evident through these conversations.
  • Seek References from Hired Sales Reps: Ask for references from three sales representatives they previously hired. Speak with these reps to understand how they collaborated to exceed quotas. Listen for insights into the candidate's hands-on sales leadership.
  • Be Wary of Overly Broad Ambitions: Be cautious if a VP of Sales candidate expresses a desire to oversee "more than just sales"—for example, Sales + Customer Success + Marketing. While cross-functional collaboration is vital, a truly passionate and effective sales leader primarily wants to focus on and excel at sales.
  • Assess Value Proposition Understanding: While you don't expect a candidate to be an immediate expert on day one, a great salesperson will quickly grasp and articulate your product's value proposition. If a candidate struggles with this fundamental understanding, time is unlikely to remedy the issue.
  • Always Talk to Their Old Bosses: Do not skip this step, especially if you have any doubts. Former bosses can offer direct insights into a candidate's selling ability. They'll know for sure if the candidate was a good salesperson and will often be candid when asked directly, even if they're generally protective.

Finally, ask them to sell you the value proposition of your own company. Can they truly articulate it compellingly, or do they resort to recycled buzzwords and generic statements? If their answers don't inspire confidence, you likely don't have a strong VP of Sales candidate.

Remember, if you skip these critical checks and hire someone who doesn't genuinely understand your value proposition, the responsibility for a poor outcome lies with the hiring decision, not solely with the candidate.

Real-World Lessons from Sales Leaders

Consider the stories of two VPs of Sales:

  • One leader, after a successful four-year tenure that saw his startup become a decacorn, immediately immersed himself in direct selling during his first week. He talked to customers, learned the product firsthand, and personally drove sales, eventually leading revenue for a multi-billion dollar company.
  • Another VP of Sales, whom I know personally, recently lost his job. He admitted his mistake was not being hands-on enough, failing to engage with customers or get involved in direct sales during his initial months. Instead, he focused heavily on processes and systems. Sales plummeted, and he ultimately lost his role.

A New VP of Sales Has to Close Deals Themselves to Start. And Not Just Be a Manager. pic.twitter.com/nEAuOWfnu8