On episode 21 of The Insiders podcast, hosts Richard Lane and Simon Hazeldine have a chat with Jamal Reimer, founder of Enterprise Sellers. 

Jamal is an experienced senior enterprise seller who specialises in finding and closing big deals. He founded Enterprise Sellers in 2022, a networking community that allows sales professionals to thrive amongst executives and mega deal experts from SaaS and tech companies. In 2021, he authored the book Mega Deal Secrets, a pragmatic handbook that teaches readers all the characteristics of a big deal sales cycle in today’s modern selling landscape. 

Highlighting his career highs and lows over 20 years, Jamal discusses how shifting his selling mindset and creating the right environment for grand thinking enabled him to close his first megadeal. 

Create a mega-deal culture 

Jamal defines a mega-deal as “deals that are significantly higher than what is typical in your selling reality, role or industry”. He is a strong believer that high performance selling can be learned through coaching and experience. 

“We don’t have to be born with the mindset. We don’t have to be born with a personality of fearlessness, or some kind of pixie dust that we can just kind of magically throw at our customers to enchant them, we can learn this, I learned this! The seller who was fired twice in a row for underperformance and was just about to get out of the whole gig of B2B sales.” 

Reflecting on his past experiences of seeing salespeople lose their mega deal, grand thinking mindset through a change of environment Jamal said:  

“I’ve seen reps who have done a single megadeal, lose their grand thinking, and either the environment will change, or their territory will change, or their boss will change, or there’ll be some change, and they allow that change to lock them into a lower level of thinking.” 

Sales culture plays a huge role in what teams can achieve. From how much your salespeople sell to how productive they are, this all comes down to sales culture quality. This underlines that not only are salespeople responsible for generating mega-deal culture and mindset– but businesses are too! 

Leverage executive whispering 

According to Jamal, large enterprise deals happen because executives make them happen. It’s all about learning to think like an executive. Therefore, he developed a technique called executive whispering to build better strategic relationships and accelerate mega-deals through the pipeline. Jamal gives his advice on how to execute this approach to selling: 

“The way to get into this is leveraging people around you who are aligned with you in your efforts, who already have or who are closer to that pure business status. And the first port of call is your own executives. So, what we talk about is this executive whispering is the art or science of working with executives on both sides of the table, the customer side and internal to your organisation. 

Executives are nowhere as intimidating as the mid-level guys who were using all this technobabble to credentialize themselves in front of large groups. And the executives tend to be plain talkers, who use normal everyday language to describe problems or opportunities or situations simply because there isn’t a lot of time.” 

Engage in conversational presenting 

Oftentimes sales pitches can be PowerPoint heavy and feel impersonal, whereas engaging in conversational presenting takes an alternative approach. It’s about creating a two-way conversation that has customers at the centre. Calling attention to the importance of selling in conversation mode, Jamal argues that applying this tactic when prospecting into C-Level can help close big deals quicker.  

“Staying in presentation mode, instead of conversation mode. And very closely related to that is simply talking too much. A lot of sellers, particularly when they feel they’re not feeling confident, feel that the way to add value and credibility is to say more. 

The opposite of that is to ask a lot of smart questions, pose some challenging or engaging concepts and that’s what ignites executives they’re like, ah, she’s got a great idea here and this is something that we want to talk about. And she’s letting me do some talking. Now you’re engaged.” 

Reach out to see how durhamlane can help you to overcome your B2B sales challenges. To learn more about implementing a mega-deal mindset, listen to episode 21 of The Insiders podcast.

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