In the latest episode of Path to Growth, Tracy sat down with Jen Allen-Knuth, founder of DemandJen, to talk about her career in sales, the misconceptions that hold sellers back, and how to create real impact in an industry that is constantly evolving.
With nearly two decades of experience in enterprise sales, Jen has seen firsthand how buyer behavior has changed—and why traditional sales tactics often fail. In this conversation, she shares the key lessons that have shaped her approach and how sellers can adapt to be more effective.
The Biggest Misconception About Sales
For many people, sales still carries the stereotype of aggressive, pushy tactics. Jen was no exception—before entering the profession, she thought sales was about persuasion and pressure. But she quickly learned that the best sellers aren’t the ones who talk the most; they’re the ones who listen the best.
Success in sales isn’t about always closing the deal. Instead, it’s about understanding what drives buyers, helping them make a case for change, and guiding them through complex decision-making processes.
Why Slowing Down Can Speed Up Sales
One of the biggest mistakes sellers make is rushing to a demo or proposal before fully understanding the buyer’s motivations. Jen advocates for slowing down the front end of the sales process—helping the buyer quantify the cost of inaction before ever pitching a solution.
Too often, sellers assume that if they can prove their product is better, the buyer will purchase. But the reality is that buyers are often comfortable with “good enough” and reluctant to change. Jen emphasizes that sellers must first help buyers recognize why the status quo is no longer sustainable.
The Right (and Wrong) Way to Do Cold Outreach
Cold outreach is still an essential part of sales, but the way most sales teams approach it is broken. Jen shared key principles for writing effective cold emails, especially when selling to enterprise buyers:
* Keep it short. Executives don’t have time to read long emails. The most effective messages are clear, concise, and to the point.
* Use a simple subject line. Flashy, clickbait-style subject lines land in spam. Instead, use one or two words that directly relate to the email’s content.
* Adopt an “unsure” tone. Instead of assuming you know everything about the buyer’s problems, ask open-ended questions and let them fill in the gaps. This approach builds credibility and invites conversation.
Sales Leadership and Culture: What Makes a Team Thrive
Beyond sales tactics, Jen also shared her perspective on what makes a great sales culture. Strong sales leadership, she argues, is about tough love—having honest conversations with reps about what’s in their control and focusing on what really moves the needle.
She also pushes back on the idea that “sales is a numbers game.” While activity matters, quality matters more than quantity, especially when selling to enterprise buyers. The best sales teams focus on the right conversations, not just more conversations.
Building a Personal Brand in Sales
Jen also discussed the importance of building credibility beyond the sales call. Engaging on platforms like LinkedIn isn’t just about content—it’s about showing up where your buyers go to learn and establishing yourself as a trusted voice in your industry.
Many sellers hesitate to post on social media because they fear looking inexperienced. But Jen encourages sales professionals to share their real experiences and ask genuine questions—engagement and learning are far more valuable than trying to sound like an expert.
Final Takeaways
Sales is always evolving, but the fundamentals remain the same: be curious, be empathetic, and focus on helping buyers make better decisions.
If you’re a sales professional, team leader, or entrepreneur looking to improve your sales motion, this conversation is full of actionable insights.
Listen to the full episode here.
Stuart Frederich Smith, CMO of TigerEye has built a history of leading great teams and launching impactful campaigns. With more than two decades of experience in marketing, product and operations, Stuart is a cross-disciplinary leader committed to collaborative execution. He holds a BA in Film, Television & Theatre from the University of Notre Dame and lives with his family in Portland, OR.
