Deal Motivation, Momentum & Risk with Cale Tully, VP Enterprise & Mid-Market Sales, at Sprout Social

Our guest for Episode 22 is Cale Tully, VP Enterprise & Mid-Market Sales, at Sprout Social.
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Welcome to Season 3 of 10/10 GTM: The Podcast for Revenue Leaders!

Our guest for Episode 22 is Cale Tully, VP Enterprise & Mid-Market Sales, at Sprout Social. Prior to joining Sprout Social, Cale spent 11 years at Salesforce working in leadership roles.

In this episode, Ross and Cale discuss three tips for operationalizing deal excellence. These include understanding the three 'whys' behind your prospect’s motivations, maintaining deal momentum through frequent communication, and calibrating deal risk to ensure success.

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

Understanding the three ‘whys’  

The first step to operationalize deal excellence is to understand your prospect’s motivations. Here are three ‘why’ questions that serve as a litmus test to gauge deal viability: 

  • Why does this company need our product? 
  • Why will they buy from us versus a competitor? 
  • Why do they need to buy now versus in the future?

The first question will help you uncover your prospect's pain points, which should align with the solutions offered by your product or service and be directly tied to business outcomes. If the solutions aren’t, this is a red flag signaling lack of urgency. 

Additionally, you need to identify how your organization is uniquely positioned to bring value to the prospect you’re trying to sell to and how your solution is differentiated against competitors. What is it, specifically about your product or service, that allows you to win compared to other offerings on the market? 

Lastly, why is the timing right for the prospect now versus sometime in the future? Evaluate the urgency of the project relative to other priorities the prospect has. This will help you determine the likelihood of the deal moving forward so you know where to focus your time and attention. 

“We talk all the time about the idea of slowing down to speed up. The early parts of the cycle are so important. If you qualify properly, do detailed discovery, and spend time upfront understanding the organization, it makes everything else in the sales process easier,” says Cale. 

Maintaining deal momentum and communication

Frequency of communication is an excellent indicator of where a deal ranks on the list of priorities. The questions you’ll want to ask yourself are: 

  • How quickly are people being responded to? 
  • How fast do deals move from stage one to stage two? 

Your answers will help you determine how much momentum you have behind each deal, which drastically impacts conversion rates. Leveraging tools such as Salesforce or deal boards allows for better understanding of deal status and communication effectiveness, enabling you to develop informed perspectives on deal momentum.

Calibrating deal risk to ensure success 

When it comes to calibrating deal risk to ensure you’re spending your time on the right accounts, you need to ask tough questions such as: 

  • Are you telling a story that resonates with your prospects? For example, if you’re selling to finance, get your CFO involved. This internal stakeholder can provide perspective, and give you an external point of view. 
  • How does what you’re selling connect to the prospect’s priorities and outcomes the company is trying to accomplish? This helps you determine whether there’s urgency for the prospect, and the likelihood of this deal closing. 
  • Did you follow the MEDDIC or similar process to properly qualify your prospect? You don’t want to rush through the discovery phase. Properly qualify the accounts you’re working on so you don’t waste your time and energy on deals that won’t close. 

“Being single-threaded in the cycle is dangerous. If it’s one person’s priority, it’s probably not going to get done. The best deal cycles have a lot of stakeholders involved. Who you’re talking to along the way is also a strong indicator of whether you’ll have a successful outcome,” says Cale. 

Rapid fire: Cale’s fast sales insights

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

What’s the main reason most teams miss their ARR goals? Short term it’s pipeline coverage. Longer term it’s the profile of your talent. 

What’s your favorite resource for revenue leaders? Never Split the Difference by Chris Voss. 

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

Best way to unplug from the demands of leadership? Exercise and being outside. 

About Cale

Cale is a results-driven sales professional with a proven ability to achieve revenue goals and high customer satisfaction levels. He specializes in selling SaaS and has a proven track record of generating pipeline, protecting profit margins, and building relationships with C-level executives. 

Currently serving as the VP of Enterprise & Mid-Market Sales at Sprout Social, Cale has been with the company for over six years. Before joining Sprout Social, he held leadership roles at Salesforce for more than a decade, including serving as VP of SMB Sales and VP of ESB.