Measuring Enablement: Stephanie Middaugh’s Proven Approach

October 26, 2023
Content Marketing | Marketing Strategy | Taking the Lead

Episode Summary

In this episode of Taking the Lead, host Christina Brady engages in an insightful conversation with Stephanie Middaugh, a seasoned sales enablement professional from Pinecone. Throughout the discussion, Stephanie provides a wealth of expertise on the often-misunderstood world of sales enablement.

Stephanie emphasizes the critical importance of aligning sales enablement initiatives with business objectives. Rather than relying solely on lagging indicators, she encourages a focus on leading indicators to predict outcomes effectively. By doing so, organizations can develop a clearer understanding of whether their enablement efforts are truly making an impact. Stephanie’s approach is a refreshing departure from the conventional method of merely assessing outcomes and provides a valuable perspective on how to drive success proactively.

The conversation dives into the multifaceted role of sales enablement, including its involvement in event planning and program management. Stephanie acknowledges that enablement often finds itself at the base of the organizational hierarchy, where various responsibilities accumulate. Despite this challenge, she underscores the need for enablement professionals to define their roles and impact clearly, ensuring they are recognized for their crucial contributions to a company’s success.

Featured Guest

Name: Stephanie Middaugh

What she does: Head of Global Enablement

Company: Pinecone

Noteworthy: Stephanie Middaugh, Sales Enablement Pro at Pinecone, specializes in driving organizational success.

Key Insights

Measuring Sales Enablement: Leading Indicators Over Trailing Metrics

Stephanie Middaugh highlights the importance of measuring sales enablement success using leading indicators rather than just trailing metrics. Instead of solely focusing on hitting numbers and sales quotas, organizations should assess whether enablement efforts are ingraining the right behaviors and skills in their teams. By looking at leading indicators, such as post-training metrics and behavior changes, companies can proactively ensure that enablement initiatives are effective in driving long-term success.

The Expansive Role of Sales Enablement: From Training to Event Planning

Stephanie discusses the diverse responsibilities of a sales enablement role, which often includes tasks ranging from training and coaching to program management and event planning. She explains how enablement professionals are the heart of an organization, building cross-functional relationships and juggling various roles to support the team’s success. Stephanie emphasizes the need for organizations to adapt enablement roles based on their size, maturity, and specific needs, emphasizing flexibility and constant iteration.

The Significance of Understanding Human Behavior in Sales

Stephanie underscores the importance of understanding human behavior, both in sales and within organizations. She suggests that grasping how people think and interact can greatly enhance sales enablement efforts. By utilizing tools like the CliftonStrengthsFinder evaluation, enablement teams can gain insights into the diverse perspectives and strengths of team members, fostering better collaboration and communication. Stephanie believes that a deeper understanding of human behavior can lead to more effective enablement strategies and improved overall team performance.

Episode Highlights

Measuring Enablement Success: Leading Indicators vs. Trailing Metrics

In this segment, Stephanie Middaugh discusses the challenge of measuring enablement success. She emphasizes the importance of using leading indicators rather than solely relying on trailing metrics. Stephanie points out that while many organizations focus on hitting sales numbers and quotas, it’s essential to assess whether enablement efforts are driving the right behaviors and skills within the sales teams.

“One of my last companies, we were trying to break into a new persona that we were selling into. And I rolled out an entire training initiative around, okay, we’re gonna sell. We’re going to talk about this persona. What do they care about? What are their struggles? What are their pain points? How does our product solve for those? What negotiation techniques do you need to be watching out for? What types of triggers should you be listening for? And success was defined at the beginning of the initiative.”

The Multifaceted Role of Sales Enablement

Stephanie dives into the wide-ranging responsibilities of sales enablement professionals. She highlights how their roles often encompass training, coaching, program management, and event planning. Stephanie explains that enablement teams are integral to an organization, building cross-functional relationships and adapting to various roles to support the team’s success despite the common misconception.

“I see a lot of young enablement professionals, or even inexperienced enablement professionals […] say, I was working with a client, and I was hearing them say, well, we have pretty good engagement. And I was like, what does engagement mean? Define that term for me. And they were like, well, they asked questions. And I was like, that doesn’t mean it’s engaging, though. “

Event Planning’s Place in Sales Enablement

This part explores the role of event planning within sales enablement. Stephanie shares her experiences in handling events like sales kickoffs and President’s Club trips. She discusses how, in some cases, enablement teams end up organizing these events due to their cross-functional nature and the need to ensure alignment and training.

“It’s that constant kind of feeling of like, ‘Oh, I’m not doing enough.’ If you’re a team of one, if you’re a team of anything less than, like, five at an organization, guaranteed, you’re not doing enough.”

Leveraging Psychology in Sales Enablement

In this segment, Stephanie underscores the significance of understanding human behavior, both in sales and within organizations. She highlights the benefits of tools like the CliftonStrengthsFinder evaluation in gaining insights into team members’ perspectives and strengths. Stephanie believes that a deeper understanding of human behavior can lead to more effective enablement strategies and improved overall team performance.

“I think honestly, that is one of those skills that I think people should kind of drill in on is like, it’s not even just like understanding the human brain. It’s like, how do other people think?”

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