How To Create Urgency, Build Pipeline, and Make Outbound Work (with Jen Allen-Knuth, Founder of DemandJen)

#308 Sales Alignment | In this session from Drive 2025 titled “Building Pipeline in the Shiny Object Era”, Jen Allen Knuth unpacks why deals stall even when your product is objectively better, how the explosion of shiny tools and AI noise is making it worse, and why most teams are unintentionally fueling the problem with me-centric messaging. Jen shares the two zero-dollar exercises every team should run to quantify how much pipeline they’re losing today, align sales and marketing around the true blocker, and rebuild outbound messaging that creates curiosity.

PS. Want to join us at Drive 2026? Head over to exitfive.com/drive to join the waitlist for Drive 2026 and be the first to know when tickets go on sale.

Timestamps

• (00:00) - – Dave’s Intro
• (03:44) - – Jen’s Story & Why She’s Here
• (06:34) - – The Real Enemy: Buyer Status Quo
• (10:41) - – The Shiny Object Era
• (14:41) - – How Status Quo Kills Deals
• (22:11) - – The Close-Lost Audit
• (30:54) - – The “We” Problem in Outbound
• (33:39) - – The Raincoat Example & Messaging Shift

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