Why Most Founders Fail at Sales (And How to Fix It)

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When you’re the founder of a startup, selling your vision can feel like an uphill battle. Many founders find themselves in a constant cycle of pitching, but they struggle to close deals. Why? Because selling as a founder is different from traditional sales roles, and it comes with unique challenges. You’re wearing multiple hats—developing the product, managing operations, and trying to sell, all at the same time.

This post will dive deep into how founders can move from endless pitches to closing deals faster. We’ll challenge some common myths and share alternative methods that have worked for others. Whether you're a seasoned entrepreneur or new to founder sales, these insights will help you fine-tune your approach.

Myth 1: Founders Are Always the Best Salespeople for Their Product

Many founders believe they're naturally the best person to sell their product. They’re deeply familiar with every feature and can passionately convey their vision. However, being too close to the product often means you focus on what you think is important, rather than what your buyer actually needs. While your passion is an asset, it can also prevent you from truly understanding your prospect’s perspective.

Alternative Approach: Become More Buyer-Centric

Instead of leading with features and benefits, start by understanding your customer’s pain points. Founders should ask probing questions that reveal the specific challenges their prospects are facing. One effective technique is SPIN Selling (Situation, Problem, Implication, Need-Payoff), which helps uncover deeper problems and frame your solution as the ideal fix. For example, you might start by asking about their current process (Situation), dig into the pain points (Problem), and explain how your product eliminates those (Need-Payoff).

Incorporating Gong.io or Chorus.ai—AI-powered tools that analyze sales calls—can also help founders identify patterns in successful conversations, showing you when to pivot, ask more questions, or dive deeper into specific issues. Additionally, reading “The Challenger Sale” by Matthew Dixon can give you a structured approach to teaching prospects something new, which is crucial when you're introducing innovative products.

Tip: Use Gong.io’s conversation intelligence to identify when in the sales call you’re losing engagement and adjust your approach in real-time or for future calls.

Stat: According to Gong.io, top sales reps ask 11-14 questions in their first call. Use that as a benchmark to guide your buyer-centric conversations.