How to Position Products and Problems to Close Deals with Jen Allen-Knuth, Founder of DemandJen

10/10 GTM Episode 20
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 20 is Jen Allen-Knuth, Founder of DemandJen. Jen brings 18 years of sales experience to the conversation, and has worked at companies such as Challenger and Gartner. 

In this episode, Ross and Jen discuss how to position products and problems to close deals.  They explore strategies for territory prioritization and identifying problem fits, alongside techniques to guide prospects in rethinking their assumptions.

Listen to the episode here, and get the key takeaways from our conversation below.

Prioritizing territory and problem fits 

A mistake many reps make when it comes to prioritizing their territory is that they target the most recognizable brands first. However, this approach falls short because it doesn’t reveal whether these organizations are a good fit for your product or service to begin with, or if you can even solve the problems they have. 

To effectively identify the opportunities worth your focus, you’ll want to focus on the problems your organization is uniquely positioned to solve. As you’re researching potential prospects, gather information on the following: 

  • What does this company sell?
  • How do they sell it? 
  • Who do they sell it to?
  • How do they make money?

Once you filter through this lens, it will help you eliminate opportunities that don’t really need your product — even if they fall within the target demographic.

“Use demographics to filter out the bad, but also look at the unique problem you solve, and judge each account based on the likelihood that account is experiencing that problem. This may happen at an individual level if you’re selling into enterprise, or by a needs-based industry segmentation if you’re selling into SMB or Mid-market,” says Jen. 

Reframing beliefs vs. telling someone they’re wrong

A common sales tactic is to approach prospects with a pitch about how your product or service is the best on the market. But the trouble with this approach is twofold: firstly, people don’t always buy the best. Oftentimes, they’re willing to settle for good enough. Secondly, if you try to convince prospects their behaviors are wrong, it creates distance between you and your buyer. 

Beliefs and assumptions, shaped by previous experiences, dictate behavior. That’s why rather than trying to get someone to admit they’re doing something wrong, a more effective approach is to capture their interest by using a relevant example that encourages them to shift their perspective and identify their problem. 

“I would look at a company, use the problem fit prioritization we discussed earlier, and say, ‘40 to 60% of B2B deals are lost to no decision. I’m not sure if this is happening in your organization, but here’s one way to size it — we’ll go into your CRM and pull a full list of all the opportunities that are forecasted to close this quarter.’ Then we’ll see how many of them haven’t had a meeting in the last 30 days. Those are the deals that are at risk for no decision,” says Jen. “I did this, and there was an enterprise account that came back. They were at the end of the year looking at their annual pipeline. And they discovered they had $90M in forecasted opportunities that had not had meetings in the past 30 days that they were at risk of losing.” 

The notion of reframing beliefs is not about convincing people they’re not doing something well enough. Instead, it’s about giving them the tools they need to size the problem and realize it really is an issue. When you accomplish this, people will raise their hands and want to talk to you about your solution.  

Laughing at the problem

In sales, laughter isn’t just a break from the grind — it can help you build a safe, open environment and solve problems faster. Instead of pointing the finger and accusing them of doing something wrong, ask: “What are the problems we can laugh at?” and “What are the alternatives?”

The goal is to collectively come up with solutions and give your team the resources and tools they need to be successful. This approach doesn’t diminish the issue, it makes it more approachable. It’s a shift from a culture of blame to one of curiosity and creativity.  

Rapid fire: Jen’s fast sales insights

In a rapid-fire Q&A session, Jen shares her insights with us on a wide range of topics: 

What’s the main reason most teams miss their ARR goals? Leaders are sitting in closed door rooms looking at ARR reports instead of looking at the conversations their sellers are having. 

What’s your favorite resource for revenue leaders? The Challenger Sales Methodology. 

What’s the number one challenge for revenue leaders in 2024? Arming sellers to be relevant and to have business acumen. 

SMB, Mid-market, or enterprise? Enterprise. 

What’s the most important org: Sales, CS, or Marketing? CS. 

Best way to unplug from the demands of leadership? Adopt rescue dogs. I have four of them!

About Jen Allen-Knuth

Jen is a seasoned sales leader with 18 years of enterprise experience.She sold more than $50M to C-level executives while at Corporate Executive Board, Gartner, and Challenger Inc. 

In September 2023, she launched DemandJen, a keynote speaking venture aimed at empowering sales reps to overcome customer status quo and transform their sales conversations into a competitive advantage.