In complex deals, frame your solution as part of a larger strategic "approach" that aligns with the buyer's existing initiatives. First, gain consensus on this shared approach, then position your offering as the foundational technology that enables it. This avoids commoditization.

In enterprise sales, the user and buyer are different people. While the user needs a problem solved, the buyer needs a business outcome that advances their career. Product managers must identify and build for the metric that makes their buyer look good—like cost savings or productivity gains—to secure the sale and ensure product success.

Executives don't care about tactical benefits like 'five fewer clicks'. A crucial skill for modern sellers is to extrapolate that tactical user-level gain into a strategic business outcome. You must translate efficiency into revenue, connecting the dots from a daily task to the company's bottom line.

Don't overwhelm an enterprise buying committee by pitching all of your product's features. Instead, survey each member to find the 2-3 features that resonate most broadly. Focus all messaging and demos on just those features to create a clear, concentrated value proposition.

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.

Sales professionals frequently encounter their most significant conflicts within their own organizations. Achieving internal buy-in and navigating cross-departmental friction can be more demanding than persuading an external client, underscoring the necessity of strong internal persuasion and relationship-building skills.

Discovery has three levels: Situation (what they do), Operational Problem (a day-to-day annoyance for a champion), and Executive Problem (the business impact). Sales reps fail when they solve operational issues without connecting them to the executive-level "so what" that justifies a purchase.

Don't just sell logical features. Frame your solution as the tool that allows the customer to achieve their own psychological victory. Help them build an internal business case that makes them look brilliant, positioning them as the savvy decision-maker who found the perfect, high-value solution for their company.

A sales pitch fails when it doesn't align with the buyer's subjective worldview. For example, a C-level executive's philosophical framework is vastly different from a frontline manager's. The key is to map your solution onto their current story, not force a new one.