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
• (03:34) - – Jen’s Story & Why She’s Here
• (06:24) - – The Real Enemy: Buyer Status Quo
• (10:31) - – The Shiny Object Era
• (14:31) - – How Status Quo Kills Deals
• (22:01) - – The Close-Lost Audit
• (29:30) - – The “We” Problem in Outbound
• (32:15) - – The Raincoat Example & Messaging Shift

Join 50,0000 people who get our Exit Five Newsletter here: https://www.exitfive.com/newsletter
Learn more about Exit Five's private marketing community: https://www.exitfive.com/

***

Today's episode is brought to you by Knak.

Email (in my humble opinion) is the still the greatest marketing channel of all-time.

It’s the only way you can truly “own” your audience.

But when it comes to building the emails - if you’ve ever tried building an email in an enterprise marketing automation platform, you know how painful it can be. Templates are too rigid, editing code can break things and the whole process just takes forever. 

That’s why we love Knak here at Exit Five. Knak a no-code email platform that makes it easy to create on-brand, high-performing emails - without the bottlenecks.

• Frustrated by clunky email builders? You need Knak.
• Tired of ‘hoping’ the email you sent looks good across all devices? Just test in Knak first.
• Big team making it hard to collaborate and get approvals? Definitely Knak.

And the best part? Everything takes a fraction of the time.

See Knak in action at knak.com/exit-five. Or just let them know you heard about Knak on Exit Five.

***

Thanks to my friends at hatch.fm for producing this episode and handling all of the Exit Five podcast production.

• They give you unlimited podcast editing and strategy for your B2B podcast.
• Get unlimited podcast editing and on-demand strategy for one low monthly cost. Just upload your episode, and they take care of the rest.
• Visit hatch.fm to learn more