Enterprise buyers are not waking up hoping to hear about your latest feature. They are trying to protect money, reduce risk, and avoid career-ending mistakes. In this season opener of Match B2B Insights - The Pain Advantage, Brenda hosts Benny Fluman and Brian Newman for a deep dive into how pain really drives complex B2B deals.

Together they unpack why feature-first messaging quietly kills pipeline and how reframing around risk, loss avoidance, and outcomes can double conversion rates. They walk through practical ways to operationalize value based selling from building a real pain matrix by persona and department, to using JTBD-style trigger interviews that lift actual buyer language into your messaging.

Benny and Brian break down real examples from companies like SentinelOne and Snowflake, showing how repositioning around ransomware fear or runaway cloud costs created massive GTM leverage, premium pricing, and faster cycles. The conversation goes into multi-stakeholder politics, regional cultural differences in talking about pain, and why websites and decks must pass a “five-second pain test” to be effective.

You will hear how to quantify the cost of inaction, structure stories around before-trigger-after, anchor price to risk avoided, and turn your team into a truly pain-driven organization with the right internal culture, enablement, and metrics.

If you sell to enterprise and you are still leading with “what we built” instead of “what you avoid,” this episode will show you how to change the game.