Podcast Summary: "How To Create Urgency, Build Pipeline, and Make Outbound Work"

Podcast: The Dave Gerhardt Show
Host: Dave Gerhardt
Guest: Jen Allen-Knuth (Founder, DemandJen)
Date: December 1, 2025
Setting: Live recording at Drive 2025, Exit Five’s annual event, Burlington, VT

Episode Overview

This episode features Jen Allen-Knuth sharing her hard-earned insights from 18+ years in sales, focusing on the real challenges of sales and marketing alignment, overcoming buyer inertia (status quo), and building pipeline in today’s crowded, “shiny object” era. She delivers practical, tactical advice—including two favorite "$0 exercises"—that can help marketers and sellers collaborate to unlock stalled deals, create more effective outbound messaging, and stop losing to no decision.

Key Discussion Points & Insights

1. Sales vs. Marketing: Rallying Around a Common Enemy

• Jen’s Perspective: Too often, sales and marketing work at odds and blame each other for missed numbers. The real enemy isn’t each other; it’s "buyer status quo"—potential customers that do nothing instead of making a decision.
• “What I hope to do in the 40 minutes that I’ve got for you today is to give us a common enemy to rally around. And that is the enemy of buyer status quo.” (05:32)

2. Understanding the Shiny Object Era

Timestamp: 10:15 – 17:45

• There's explosive growth in martech and sales tech, overwhelming buyers with options.
• Competition isn’t just “who’s in our vendor box”—it’s every company fighting for attention, time, and budget.
• AI and “build your own tool” options add even more noise.
• Standard outbound approaches (mass emails, more dials) are increasingly ineffective.
• Data: 38% of pipeline loss comes from customers simply sticking with the status quo.
• “If we are all screaming about how we have the best solution, everybody tunes out… It’s like going to a concert and all the acts turn up their music louder and louder. By the end you’re just like, ‘get me out of here!’” (13:40)

3. The Real Reason Deals Die

Timestamp: 18:00 – 27:00

• Buyers rarely say, “We choose status quo”—they say, “Let’s revisit in 6 months,” or “We don’t have budget,” or “We’ll socialize and get back to you.”
• “Budget” objections often mask a lack of perceived urgency or importance.
• Sellers are trained to “objection handle,” which pushes prospects further away.
• Fixation on “why we’re better” (vs. the true cost of inaction) is a losing approach.

4. Why Sales & Marketing Lose to the Status Quo

Timestamp: 27:00 – 32:30

• Salespeople and marketers treat initial outreach as an afterthought.

• Most prospect emails and outreach are self-centered (“I/we/our/company”); they fail to address the buyer’s real situation.

• Internal deal loss reasons (“No budget,” “Timing,” “Competitor”) don’t capture that most loss is due to insufficient urgency or importance.

  “We are asking salespeople to grade their own homework and we are never going to throw ourselves under the bus. It’s always, ‘they don’t have the budget’—not, ‘I didn’t make a compelling enough argument.’” (32:00)

5. First $0 Exercise: Closed-Lost Audit

Timestamp: 34:00

• Audit closed-lost opportunities in your CRM (January–September).

• Pull all deals lost for “status quo”-type reasons: unresponsive, no budget, no champion, “went cold.”

• Calculate the pipeline value lost to status quo.

• Use these numbers to have a collaborative, data-driven conversation across sales & marketing.

  “One company found $50 million in status quo losses… the most frustrating thing was marketing was being hammered to ‘build more pipeline’, but there was $50 million on the shelf.” (35:55)

6. Second $0 Exercise: Perceptual Curiosity in Messaging

Timestamp: 39:40 – 41:30

• Stop sending self-centered “wee-wee” (I/we/our) emails.

• Shift messaging to create “perceptual curiosity”—give prospects new information that contradicts what they believe about their own situation.

• Example: Instead of pitching a raincoat against an umbrella outright, reveal a compelling insight ( only 5% remember an umbrella, most take surge-priced Ubers).

  "We are just wee-wee-ing all over our prospects... Meanwhile, our competitor is status quo. Status quo doesn’t care if you’re better—you can win the argument and still lose the deal." (39:48)

Four Foundational Questions for Outbound Messaging:

1. Who is most likely to have this problem?
   • Target by context, not sexiest logo.
2. How do they solve the problem today, and why?
   • Understand and empathize with attractive elements of status quo.
3. What is the unintended negative consequence of their current solution?
   • Reveal hidden costs or pains.
4. Who else took a different approach, and what happened?
   • Social proof should center on peer behavior, not how great your company is.

Example “El Niño” Email Structure:
Short, prospect-centered, uses external triggers and challenges the status quo (surge-priced Uber rides as a result of forgotten umbrellas).

7. Cold Email Read-Aloud Exercise

Timestamp: 43:00

• Gather the team, have each person read their outbound email aloud.

• Group “clocks out” (raises hand or signals) when they lose interest.

• Builds empathy for what works/doesn’t from a real-world listening perspective.

  "I’ve had sellers stop mid-sentence and say, 'You’re clocking out, aren’t you?' Sometimes, when we're writing, we're not thinking what the person on the receiving end is actually feeling." (43:20)

8. Call to Action: Collaborate (Don’t Go It Alone)

• Meaningful pipeline messaging work should be done cross-functionally: sales, marketing, product, and leadership.
• Step one is always building understanding (shared “common enemy”) before launching into new tactics.

Closing Thought:
Sales isn’t hard if we understand human psychology and recognize that buyers default to “good enough.” Our job is to help them see why their status quo isn’t good enough anymore—before we pitch our solution.

Notable Quotes & Memorable Moments

• On Sales and Motivation: “The answer to everything isn’t ‘more dials’ or 'more emails.' Screaming into the void isn’t effective.” (16:45)
• On Pricing Objections: “What if I give you a 15% discount? Like, what is it about 15%? … If you don’t perceive you have a problem, it doesn’t matter how cheap my solution is.” (31:20)
• On Messaging: “We are just wee-wee-ing all over our prospects… we're talking about wee-wee, we're talking about dog feces—this is my talent!” (39:48)
• On Changing Your Approach: “You might have the best damn raincoat in the world, but if it’s $100 and my umbrella is free, that’s a tough thing to overcome—unless you show me the cost of my current way.” (41:25)
• On the Cold Email “Pervert” Exercise: “I read cold emails from sellers all the time. Most look like, ‘At Jen’s Packable Raincoat Company we’re revolutionizing...’ It’s just all features, all about us. And this is what we need to stop.” (41:05)
• On Collaborative Messaging: “I have yet to work with an organization who’s gone through these four questions and hasn’t come out better on the other side.” (43:00)

Segment Timestamps

• [03:19] – Jen’s entrance, personal story (rescue dogs, context for speech)
• [05:33] – Framing the “common enemy” (buyer status quo)
• [10:15] – The “Shiny Object Era” explained
• [18:00] – Why buyers opt out (status quo wins)
• [27:00] – Loss reasons, blaming marketing/sales
• [34:00] – Closed-Lost Audit ($0 Exercise #1)
• [39:40] – “Wee-wee” messaging problem, perceptual curiosity ($0 Exercise #2)
• [43:00] – Collaborative email read-aloud exercise
• [44:30] – Session wraps; Q&A intro

Actionable Takeaways

• Audit your pipeline: Size and frame the true status quo problem together with sales.
• Rethink outreach: Create curiosity; focus on helping prospects see why their current approach is costing more than they realize.
• Cross-team exercises: Run loss audits and cold email workshops with sales, marketing, and product teams together for better alignment.
• Stop “wee-wee” emails: Make messaging about the prospect’s reality, not your own features.

Jen Allen-Knuth’s session reframes pipeline and outbound as a joint marketing and sales challenge: stop blaming each other, align on the status quo as the real enemy, and change your messaging and activities to create genuine urgency—without spending more.

For session slides or further details, Jen offered to share via email after the event.