Contrary to the belief that big B2B decisions are purely rational, they are more susceptible to biases. With infrequent, high-stakes purchases like enterprise software, decision-makers face greater uncertainty and are more likely to rely on mental shortcuts and biases like social proof.

Startup founders often sell visionary upside, but the majority of customers—especially in enterprise—purchase products to avoid pain or reduce risk (e.g., missing revenue targets). GTM messaging should pivot from the "art of the possible" to risk mitigation to resonate more effectively with buyers.

For a new product, don't choose between targeting executives or end-users; do both simultaneously. While mapping the C-suite (top-down), engage lower-level employees to gather intel and build internal champions (bottom-up). This dual approach creates pressure and relevance from both directions.

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.

The key to accelerating from $1M to $10M in revenue was evolving the sales narrative. They moved from discussing technical details with CTOs to explaining business impact, like compliance and audit readiness, to non-technical buyers like Chief Compliance Officers and CFOs.

Don't just solve the problem a customer tells you about. Research their public strategic objectives for the year and identify where they are failing. Frame your solution as the critical tool to close that specific, high-level performance gap, creating urgency and executive buy-in.

StatusGator initially targeted developers but found success only after realizing IT directors were the true buyers. The mistake was focusing on users who loved the tool but lacked the authority and budget to purchase it for their company.

Snyk achieved developer adoption but failed to monetize until they addressed the needs of the actual buyer—the security team. They had to add governance and reporting features, realizing that user love doesn't automatically translate to sales when the user and buyer are different people.