Hearsay on Training Best Practices and Strategies for Enterprise Deals

On getting into sales and enablement…

I am from a small town in South Carolina, grew up singing in church, and then went to college and graduate school to study performance. For the first decade of my career, I was a professional opera singer. I took a little break in my early thirties and got a sales job, at my mom’s recommendation. She had switched to sales halfway through her own career and said, “Hey, I think this would work well with your personality. It’s a good thing to do while you figure out your next step.” Only it turned out to be my next step.

Since then, I have taken turns all around the table in the revenue department, as a Sales Manager, Sales Operations and Renewals.

I feel like enablement is my forever home inside of the revenue organization. It uses my skills set the best and aligns with my passion more than anything I have done in my career.

On finding the perfect role for himself…

When I was looking for a job, I interviewed with 15 different companies. That gave me a chance to choose a company that aligned not only with my skill set but also with what I wanted out of my life and career.

If you look at our company values at Hearsay, you’ll see that one of them is kaizen, a Japanese word that translates to “continuous improvement.” I am a Lean Six Sigma Black Belt, so kaizen is my full-on philosophy of life and my mantra is “100% Customer-Focused.” I am also a big believer in GRSD, or Get the Right Stuff Done. So I felt really aligned with the values here. I felt like I could come in and hit the ground running, which is what I’ve done.

On driving the right behaviors and measuring success…

My philosophy is that programs without quantitative metrics can’t grow. If you are building a coaching program and people are adapting to it, you need to measure not only manager performance and rep performance but also enablement’s performance. I always ask: Is this the right structure? Are people committing to the right behaviors? And what outcomes are doing the driving?

This matters even for things like onboarding. We talk about ramp time, but onboarding and training should be heavily metrics-driven too. It should not just be “I graduated and checked the box.” It is also: “Here are the things I learned. Here are the behaviors I adapted to. Here are the results of those behaviors over time.” And then you need to revisit those core competencies in sales over time to make sure that people are developing throughout their career. Everything I do is super metrics-driven.

On building a diverse team…

I think people who know me know I am a people person and care a lot about the people I work with, so I am really thoughtful about creating teams. Diversity and inclusion are first and foremost for me, in a lot of different ways. You want a lot of different types of people on the team.

I look to find people from different backgrounds who are experts in their spaces—whether it is sales, marketing, training or analytics—to create a sense of diversity. The fun part is the mad science experiment you create, which is combining their skill sets when you put them together on projects. So, watching what happens when you put the analytics person next to the classical trainer and figuring out what the metrics are going to look like from those trainings. I feel like that’s what helped my team not only gel as a unit but also grow.

On enabling large enterprise deals…

At Hearsay, we often do large enterprise deals that take place over a long sales cycle. My approach for these deals is all about the team. When you’re in a long sales cycle and you’re working with C-level executives at giant companies, it is going to be a multi-threaded deal. There are going to be a ton of people involved and the challenge is really making sure that all the plays are organized across the entire account team. What’s the one playbook that includes them all? What’s the one certification program we can build that gets them all speaking the same language and positioning the products in the same way? Communication strategy is critical.

My approach right now is thinking about all the classical enablement responsibilities through the lens of the account team. And everyone on the deal team needs to create a consistent buyer’s experience throughout the buying journey.

A big thanks to Chad and the Hearsay team for chatting with us and sharing their best practices.