Baseball to Pizza to Sales Enablement Training Software: What I’ve Learned In My Career (So Far) About Selling With Excellence

I never thought I would be in sales. I came out of school with a Marketing degree, and the things I learned playing college baseball. If I’m honest, my career prospects felt bleak, and I wasn’t sure what I wanted to do. 

I ended up working as a server at a pizza restaurant to make money until one Saturday, a couple came in and sat in my section. To this day, I’m not sure if it was my charming personality or the fact that they’d each ordered several drinks, but they really took a liking to me. So much so that the husband offered me a job doing outside sales for his company. I had no experience and no real idea what I was getting into, but I was motivated and ecstatic about the opportunity. From that point years ago, I’ve been on one heck of a sales journey. 

I’ve worked for multiple companies in different sales roles, so I’ve seen the good, the bad, and the ugly of sales enablement strategy. And I’ve used all kinds of sales enablement tools along the way. From my experience I’ve been asked, “Can you give a clear sales enablement definition? What makes a strategy great? How do you measure sales enablement? Well, let’s try to answer that, shall we?

From sports to sales

My time as a college athlete prepared me for more things in post-grad life than I ever could’ve imagined. The leadership, work ethic, character, and coachability traits that sports instilled in me have stuck to this very day. The idea of a baseball team as a whole can even be tied into sales. (Not convinced? You should check out this fun playbook—Major League Sales Coaching.)

You see, baseball requires a group of individuals to work toward the same goals in order for the team to win. If even just one player is out of position on defense or doesn’t swing the bat while hitting, they can drastically affect the overall performance of the team. The same can be said about your sales enablement strategy. Treat your sales team like a baseball team by making sure each and every one of them is doing their part to contribute to the team’s success. 

So, what does this look like?

This means coaching each player individually and ensuring they’re getting repetitions in on what’s needed to excel. Everyone has a different learning style too, so it’s important for your strategy to be flexible enough to accommodate that. I can remember a couple of roles that fell short in the coaching department because they focused on top performers, and let the bottom half of reps churn to find other roles. A lot of really great people left because they felt neglected, when in reality, all that would’ve been needed to succeed was a better enablement strategy.

From the ground up

If I was starting from scratch and building an enablement program from the ground up, I would start by researching the right sales tools to meet my needs. My favorite tool to this day is SalesLoft because it gives an individual or even a small team the ability to do the work of a larger one effectively and efficiently. At the end of the day, efficiency is key, and that should be the same for your sales enablement training software. The sales enablement examples I would most focus on are coaching and practice (which isn’t surprising given my love for baseball and the examples above). Practice and repetition are both at the heart of skills development, so I’d want to make sure the sales enablement software or sales engagement software I chose was exceptional at both those things. 

That being said, it is simply not enough to have all the right tools. It’s crucial to choose the right people. Take myself for example; I had no actual sales experience, but I did have motivation. I think too often in sales hiring, we look for multiple years of sales expertise when what we really should be looking for is someone with a deep sense of “why” that motivates them.

Finding the “why”

All in all, there really isn’t a set-in-stone definition of sales enablement. I mean, the definition of enablement is just “the act of enabling”… but that doesn’t say much. I measure sales enablement by looking at how tactical job skills are being developed and by how satisfied a sales rep is in their role. A great sales enablement strategy involves coaching, practice, and an emphasis on individual development to contribute to team goals. It pairs motivated people with strong “why’s” behind what they do, and great managers who are committed to helping reps reach their full potential. By making reps feel that their development is just as important as team success, sales enablement leaders will keep them satisfied in their roles and at the same time, develop critical job skills that are going to lead to improved results for your company. THIS is how you measure sales enablement.


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