The Best of the Brutal Truth about B2B Sales & Selling - The show focuses on the enterprise Sales Process HOW TO WIN THE HARDEST DEALS IN B2B SALES
Feb 23, 2026
Ryan Kurt, a startup sales leader who scaled from rep to sales leadership after nine years selling AI products. He discusses winning deals with no market, finding high-value hooks like automated narrative reporting, scaling knowledge across teams, forecasting by reading buyer signals, and coaching reps with game-tape and tough cross-examination.
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Selling When There Is No Market
- The hardest B2B sales are for products with no market fit where buyers can't picture the value.
- Ryan Kurt compares early-stage products to a Rorschach test: start where buyers are and build the story up.
Finding A Hook By Doing The Math
- Ryan Kurt landed the hook by quantifying wasted analyst hours and pitching 90% time savings for narrative reporting.
- He targeted CMOs at large asset managers, did the math on hours×people×salary, and used that ROI to win early customers.
Use High-Volume Conversations To Find Product Market Fit
- Talk to thousands of prospects to pattern-match who truly has the problem and which messaging resonates.
- Use conferences and side-by-side demos with your scientist to expose many reactions quickly and refine positioning.