People > Processes: An Interview with Courtney Shaffer Lovold, Global Strategic Account Manager at Emarsys

By: Teresa Weirich

April 4, 2018

You may have come across a few of our recent People > Process articles including sales rock stars like Adam Weber, VP of Sales at Emplify, Melissa Gindling, Strategic Account Executive at Levementum, and most recently Russell Van Leuven, Sr. Director of Sales at DiscoverOrg. Each of these sales professionals have one thing in common: they consistently earn the respect and trust from their prospective customers. While each has a different approach to achieving that level of partnership, our goal for this series is to dig beyond the surface and to explore what makes these great sales professionals trusted advisors that their prospects view with integrity.

We continue along in our People > Processes series with our seventh article featuring Courtney Shaffer Lovold, Global Strategic Account Manager at Emarsys, an AI-driven personalization platform that provides actionable intelligence to enterprises targeting their consumers, combining machine learning and data science with true personalization and multichannel delivery. Throughout her career, Courtney has been able to observe the world of technology sales from many vantage points, ranging from small business existing account management to services to global enterprise new business sales in her current role at Emarsys. The company has 800 employees with 15 offices worldwide, so she’s had to learn how to approach sales from a global standpoint.

Through her work with existing and prospective customers, Courtney has been able to adopt a worldview that allows her to respectfully challenge her prospects while simultaneously gaining their trust—a skill that only time and experience have allowed her to develop.

Be Overly Prepared For Every Prospect Meeting

If information about a prospect is publically available, Courtney is a firm believer that it’s a sales professional’s responsibility to read up and understand that information as best as possible prior to the first meeting. From press releases to the company’s website to the last annual report, she advocates for going deep and using the information to frame up the sales conversation from the very beginning in order to set the stage for a successful sales process.

“Even before a first call, I immerse myself in my prospect’s brand. I seek to be aware of what they’re selling or marketing so I can experience the process from their customer’s perspective, which gives me a much better lens to not only guide the conversation, but understand the pain points,” Courtney explained.

Thanks to her dedication to thorough research, Courtney has the confidence to pivot if and when the prospect throws a curveball. She considers if she were in the customer’s seat, what would she want to understand? This customer-first mindset allows her to better guide the conversation rather than be at the prospect’s mercy.

Listen to Engage — Not to Respond

Sales professionals often talk in their own terminology, using company definitions, industry buzzwords, and feature-specific terms to try and sell product features. But Courtney’s experience has led her to realize that buyers don’t care about terms—they care about their specific problem, and they want to be listened to. If sales professionals approach conversations through the lens of a consultant that understands the industry inside and out (and not just their own solution), most prospects will let their guard down.

During the discovery process, Courtney will ask several thought-provoking questions and then she’ll sit back and let the prospect talk. Rather than jump in and add her two cents, she simply listens—for keywords, pain points, emotion, and any key points that she can use to articulate the problem (and solution) back to her prospects in future conversations.

Courtney also continually seeks to understand what her prospect is trying to accomplish by asking more tactical questions. For instance, she might dig into a topic by using this positioning: “I previously read in the annual report that your company has been experiencing this particular pain point, but what does that mean for you and your team?” She also seeks to clarify any confusion by using a soft approach: “In my definition, I see this particular challenge this way, but talk to me about how you see it. What is your agent of change? What will take your business where it needs to go?” By asking open-ended questions that get to the heart of the matter, Courtney is able to navigate potential pitfalls that could derail the deal later on.

Earn Trust Internally By Managing Expectations

Speaking of pitfalls, Courtney constantly tries to find reasons why her deals won’t be successful. She often asks herself: Does a competitor provide a better solution for the prospect’s problem? Is the decision maker unengaged in the sales process? Is the prospect misguided about the company’s challenges? Am I reading or hearing conflicting answers from influencers?

While it may sound counterintuitive, this approach allows her to play defense, and as a result, she has a more accurate view of which prospects will ultimately close—and which have a lesser chance. This also helps her to forecast and gain a better picture of pipeline health (which her managers also appreciate!)

Sales Professionals Don’t Have to Know ALL the Answers

Contrary to popular belief, sales professionals don’t have to know all of the answers. Courtney has found that some prospects will hone in on a certain area of interest—such as security or infrastructure—and will attempt to go deep. While Courtney can certainly scratch the surface on many topics including these, she’s found that she’ll be unsuccessful if she tries to be the expert on topics that are out of her area of expertise. Instead, she might say something to the prospect like: “It seems like you have a lot of questions about security. Can I connect you with our in-house subject matter expert who can answer all of your questions in more depth than I can?” This not only establishes credibility, it ensures that the prospect isn’t told something that won’t hold up later on in the sales process—or after they become a customer.

Courtney’s Advice: Don’t Be Afraid to Respectfully Challenge the Prospect

In 2008, five years into her working career, Courtney started in sales as a small business account manager, which was her introduction into the world of customer selling and renewing. It was this experience that allowed her to develop a transparent mindset with prospects since once a customer signs, the curtain is pulled back and there’s no hiding anything. She continues with that mindset even now in new business sales and always errs on the side of transparency and accountability. It was also her experience in existing business sales that allowed her to gain candor and confidence in conversations. Rather than being a “yes” woman, she has learned that her prospects tend to respect her much more when she tactfully pushes back and challenges their viewpoints.

“As I’ve grown in my sales career, I’ve learned to be more confident in my knowledge. I no longer allow my prospects to run meetings, which is something I had to learn early on. And while challenging a prospect can have a negative connotation, I’m always careful in how I approach those conversations and, rather than directly oppose them, I share real-life experiences or cautions from other customers. This honesty helps me to establish trust, respect, and ultimately set my prospects up for long-term success.”


  • Teresa Weirich's Headshot
    Teresa Weirich

Ready to Learn More?

For more information on best practices of great sales leaders, check out the Costello resources below. If you’d like to see Costello in action, request a personalized demo of our real-time sales playbook software.

Related Posts: