Vercel COO Jean Grosser's litmus test for a great salesperson is that engineers shouldn't be able to tell they aren't a PM for at least 10 minutes. This requires deep product knowledge, enabling sales to act as an R&D function by translating customer feedback into valuable product signals.

Assigning expansion quotas to Customer Success (CS) is a critical mistake. CS should focus on implementation, adoption, and value realization, creating the conditions for growth. However, the act of selling the expansion is a core sales responsibility that requires a sales skillset and incentive structure.

A GSB receptionist's casual chats with alumni revealed the program's long-term "fine wine" value—a strategic insight that formal surveys often miss. This shows how empowering frontline employees to listen can uncover profound user truths.

Don't wait for a formal QBR to discuss expansion. The immediate post-sale period is a golden window for additional sales. The customer's excitement and trust are at their peak. With their most urgent need solved, they are highly receptive to addressing other business challenges.

Average reps focus on product features. Top performers are "product agnostic"—they don't care about the specific product they're selling. Instead, they focus entirely on the customer's desired outcome. This allows them to craft bespoke solutions that deliver real value, leading to deeper trust and larger deals.

Instead of asking standard discovery questions, top performers pose strategic questions that require joint exploration. This shifts the dynamic from a sales pitch to a collaborative problem-solving session, creating a deeper partnership and revealing unforeseen opportunities that standard questions would miss.

Customer service isn't just a post-sale function; it shapes the pre-sale environment. A prospect's perception of your company's service, formed by word-of-mouth and online presence, directly impacts a salesperson's ability to succeed before they even make contact.

When sales teams hit quotas but customer churn rises, the root cause is a disconnect between sales promises and operational reality. The fix requires aligning sales, marketing, and customer service around a single, unified strategy for the entire customer journey.

In a marketplace with endless options, product features are table stakes. The deciding factor for buyers is now the total experience. Salespeople have lost control of the buying cycle and must now influence it by delivering exceptional service and building trust from the first interaction.