Consistency and Driving Results in the Sales Process, w/ Jeff Benson

10/10 GTM Episode 14
Transparent sales process - working together
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Welcome to Season 2 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 14 is Jeff Benson, VP of Commercial Sales at enosix. Jeff brings more than two decades of experience leading global business growth in multiple regions and sectors, including Financial Services, Retail, and Regulated Industries.

In this episode, Jeff and Ross discuss why the best sellers and revenue leaders take extreme ownership, maintain an iterative sales playbook, and are always qualifying opportunities. 

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

Take extreme ownership

When you take extreme ownership, you own your successes and failures and continuously learn from them. As such, you’re seen as someone who is honest, reliable, and transparent.

According to Jeff, practicing extreme ownership is especially important for sales leaders because they’re under constant pressure to make decisions quickly: “Making a decision 50% sooner is better than never making one. You need to train yourself to take calculated risks.” 

Of course, not every decision will be the “right one,” but when you take extreme ownership, that’s less of a concern because you have a track record of taking responsibility for the outcome and proactively working toward a solution. This, in turn, builds trust with clients, fosters a culture of accountability, and encourages continuous improvement. 

Maintain an iterative sales playbook

To create consistency and standardize processes and strategies, you need a sales playbook. But it’s not something you put together once and use forever — it should be iterative and adapt with your organization. 

“I see a sales playbook as a repository. It contains the content sellers need to be successful, as well as the processes they need to follow to step through the stages of an opportunity in a very simplistic form. In essence, it guides all matters of how a GTM team can be successful and explains what success looks like,” says Jeff. 

A good playbook will answers questions such as: 

  • Who is the target customer?
  • What are the entry and exit criteria?
  • How do we approach each stage of the sales process?
  • Who should be involved and when? 
  • What are the common objections and how do we address them?

Also, it’s important to keep this playbook simple. The information should be straightforward, easy to understand, and well organized. The purpose of this is two-fold: first, it ensures your reps are effectively able to use the strategies outlined in the playbook. Second, it streamlines the onboarding process for new reps. By equipping your team with clear guidelines and strategies, they’ll spend more time with prospective clients and less time developing individual sales strategies. 

Always be qualifying and recruiting

If you want to squeeze the most juice out of your pipeline, consider taking the “ABQ” approach, also known as, “always be qualifying.” The idea is to countersell and challenge the quality of each opportunity so you aren’t wasting time on deals that ultimately won’t close. 

“Be tenacious and find out why a customer would part with a great deal of money now. What problem will our solution solve, and how much is it worth to the customer? If you can’t answer that, you probably don’t have a deal,” says Jeff. 

The ABQ approach isn’t just about filtering out less promising leads, it’s also about refining your understanding of each deal. It allows you to delve deeper into prospects' needs and clearly outline the value your solution offers. 

In addition to qualifying, Jeff also recommends sales leaders continuously recruit new talent. “I do two interviews a month. I’m always on the lookout for great talent because people change companies and careers, and you need to be ready.” 

These two strategies help Jeff’s team bring in top talent and close deals with a longer shelf life. 

Rapid fire: Jeff’s fast sales insights

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

What’s the main reason most teams miss their ARR goals? Lack of prioritization and pre-work on the deal. 

What’s your favorite resource for revenue leaders? One of my favorite books is, “Let’s Get Real or Let’s Not Play: The Demise of Dysfunctional Selling and the Advent of Helping Clients Succeed. 

What’s the number one challenge for revenue leaders in 2024? Lead generation and converting those leads into opportunities that can be pursued. 

SMB, Mid-market, or enterprise? Enterprise. 

What’s the most important org: Sales, CS, or Marketing? To me, there are three legs to a stool and you can’t sit down at the revenue table without all three legs supporting you. 

How do you unplug? Spending time with my family or on my Harley doing cross-country trips. 

About Jeff Benson  

Jeff is an experienced technology and sales executive with more than 20 years of experience leading global business growth across multiple regions and sectors. Before joining enosix, Jeff held key senior leadership roles at various companies including FIS, Harland Clarke, Fiserv, KPMG, and SunTrust. His strategic leadership and deep understanding of various markets have enabled him to navigate complex business landscapes while fostering sustainable expansion.