Mastering Positioning, Strategy & Leadership with Jon Feldman, VP of Sales at

10/10 GTM Episode 35
Transparent sales process - working together
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 35 is Jon Feldman, Vice President of Sales at Jon is an award-winning VP who brings more than two decades of experience to the conversation. 

In this episode, Ross and Jon discuss the importance of positioning, strategy over tactics, and developing effective leaders to drive execution excellence across sales and CS teams. 

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

Mastering positioning

To win more deals, your prospects need to understand what sets your solution apart from competitors. This is where positioning comes into play.

 “I’ve taken the Sandler Sales Selling System many times. One of the most impactful lines from the program is, ‘You’ll never be perceived as better until you’re perceived as different,’” says Jon. “Think about that for a moment. Most buyers perceive solutions to be the same, which means to stand out, you need to clearly illustrate what makes your product or service unique.”

To achieve this, ask yourself two questions before you start any meeting: 

  1. How do I want the prospect to feel at the end of this meeting?
  2. How do I want the prospect to think at the end of this meeting? 

Answer these questions and use your answers to guide your discovery process. This approach will help you determine the best way to position your product or service effectively.

Jon also uses April Dunford’s approach to help tighten and fine-tune his team’s sales strategy. “She’s a genius. She developed a very simple strategy to help people understand how to position their product or service to differentiate it from other offerings.”

Focusing on strategy over tactics 

Sales is a strategic game, a thinking person’s sport. “If you’re going to approach it like it’s a transactional affair in this market, you’re not going to do well,” says Jon. “You have to consider all of the permutations that will result from the moves you make.”

And generally, reps take one of two approaches to sales: tactical or strategic. When reps take a tactical approach, they perform a basic level of discovery. This might include conducting a demo that showcases the product but doesn't customize it to the prospect and their needs. 

The best reps, however, are strategic. Their goal in any meeting is to understand the prospect and make sure they leave the meeting feeling a certain way. They ask pointed questions to uncover the root of the prospect's pain points, allowing them to position their product in a unique and compelling light compared to competitors. This approach helps them stand out and be perceived as different and better.

Strategic reps are also prescriptive. Instead of being passive and asking questions like, “What do you think the next step is?” they guide the process and say, “Typically, the next step is XYZ.” This pulls prospects through the sales cycle, leading to quicker closes and more revenue.

Developing effective leaders

70% of reps say they haven’t received formal training in sales. This means a lot of managers who work their way up don’t have the skills necessary to coach and develop their teams, optimize sales strategies, and drive continuous improvements. 

So, the question becomes: How can revenue orgs address this gap?

“The biggest thing that the industry needs right now is a massive investment in both frontline salespeople and leaders. Formal training is essential for teaching them to think strategically and treat sales as a chess game, rather than a transactional activity,” says Jon. 

Additionally, it’s important to be selective when hiring leaders because these people will mentor your reps and either guide them to success or potentially lead to their stagnation.

Jon prioritizes traits such as coachability, urgency, resiliency, credibility, and curiosity. These qualities are essential because they equip leaders with the ability to adapt to changes, drive team performance under pressure, and continually seek improved strategies and insights. Ultimately, leaders with these characteristics can significantly enhance the adaptability and competitiveness of their teams.

Rapid fire: Jon’s fast sales insights

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

What’s the main reason most teams miss their ARR goals? Lack of commitment. 

What’s your favorite resource for revenue leaders?The 48 Laws of Power,” by Robert Greene. 

What’s the number one challenge for revenue leaders in 2024? Approaching deals strategically and leaving tactics at the door. 

SMB, Mid-market, or enterprise? SMB. 

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

Best way to unplug from the demands of leadership? Taking my dog for a nice, long walk. 

About Jon

Jon is an award-winning VP of Sales with expertise in providing successful customer-specific solutions catering to a wide array of industries on a global scale. Before joining he held leadership positions at Absolute Software, Galvanize, Dell, and Oracle.