Finding the ideal candidate for your first Head of Sales or VP of Sales can be a daunting task, often taking months of searching. What happens when the "perfect" fit remains elusive? At some point, founders and CEOs must weigh the risks and make a strategic hire. This guide, drawing insights from SaaStr, distills the decision-making process into three critical criteria for evaluating candidates, especially when you need to move forward without Mr. or Ms. Perfect.
Three Essential Criteria for Your First Head of Sales
If you've spent four to five months (or even less) searching for a "true VP" without success, and a promising candidate meets these three factors, it might be time to make that crucial hire.
1. Proven Ability to Hire Quota-Exceeding Sales Representatives
This is arguably the most important criterion. A candidate for your first sales leader role must have a demonstrated track record of successfully hiring at least two sales representatives who consistently met or exceeded their quotas. Many excellent individual contributors excel at selling but have zero experience in recruitment and team building. You don't want your company to be their first learning ground for hiring. This also differs significantly from simply managing an existing small team; it's about actively identifying, attracting, and onboarding top talent.
2. Demonstrated Success Selling at Your Product's Price Point
Sales expertise isn't universally transferable across all deal sizes. Someone who excels at closing $1,000 deals may not possess the same skills, strategies, or experience required for $10,000 or $100,000 transactions. It's crucial not to overlook these fundamental differences. Ensure your candidate has a proven history of success within the specific price point and sales cycle relevant to your product or service.
3. Capacity to Train and Enable Others (Including You)
A strong Head of Sales should be an exceptional trainer. To assess this, challenge them: can they effectively train you—the founder or CEO—to sell your own product? If they can impart their knowledge and sales techniques to you, it's a strong indicator that they possess the pedagogical skills necessary to train an entire sales team. Training is a cornerstone of effective sales management, and a candidate must demonstrate this capability, including a deep understanding of your product, before they even begin building out the team.
Consider Internal Promotion Before Settling
Before expanding your search externally or compromising on key criteria, take a moment to re-evaluate your existing team. Have you thoroughly explored the possibility of promoting from within? If you have two or three high-performing sales representatives, challenge yourself to see if one of them could step up to the leadership role. Consider giving them an opportunity to hire a great sales rep. If they successfully bring in a strong team member who thrives under their guidance, you might already have a promising "stretch" candidate for your first Head of Sales right within your organization.
While these three criteria may seem straightforward, it's surprising how many CEOs overlook them when hiring their initial VP of Sales. Failing to meet these foundational requirements often leads to a quick turnover and the need to search for a second VP of Sales much sooner than anticipated.
For more insights on building a robust sales team, watch this video: