3 Lessons I Learned Building an Onboarding Program with Sales Enablement Software

Five months of experience as a Sales Development Representative (SDR) is not a lot. Sure, I learned how a sales team functions, how to follow different sales processes, and how to interact with a prospect and customer. But, the experience I gained during my five months as a rep might not stick with me for the long haul. I’ve worked through this transition as a Sales Enablement Specialist for the past eight months.

As Enablement, and specifically Sales Enablement, continues to grow as a relatively new unit within many businesses, new Enablement professionals are adapting in order to be successful. While my five months of SDR experience definitely shapes how I approach Enablement, the lessons I learned building an onboarding program shaped me even more. Here are the three biggest lessons I learned during that process that shaped my role in Sales Enablement:


1. Feedback Fuels Iteration

First, to understand the true importance of feedback please read this very short blog post. My favorite highlight from it: “As companies and teams, we can make more time to ask the hard questions—the ones that help us understand where we currently thrive and where we might have room to improve.”

In much of Sales Enablement, whether it’s ongoing coaching for reps who need development or onboarding a class of new reps who need to quickly get up to speed, success will be fueled by iteration. Each new version of previous onboarding programs, sales activity analysis and training days, e-learning content, etc. will bring better experiences for reps. However, this betterment by iteration doesn’t happen in a vacuum.

Feedback from your reps is crucial to iteration. It allows you to know what’s working well, what isn’t working well, and what’s missing. With feedback, you can form a picture of the current state and begin to discern what to do next to better your Enablement program. But it’s worth mentioning again—relying on your own experience as a rep (or Enablement professional, for that matter) won’t cut it. Get feedback from the most important stakeholders, and you’ll set yourself up well to successfully iterate.


2. Diversification is Key

I’d like to analogize personal finance with Enablement. I’m not a financial planner, nor do I have any formal education in finance, but I do understand the importance of diversifying investment assets. If you don’t, a quick Google search can fix that! The value of diversifying your personal investments and financial assets is similar to the value of diversifying the avenues from which you’re receiving feedback on your Enablement program. 

Blending together a modern sales enablement platform (like Lessonly) + in-person coaching and training + peer/mentor shadowing is great diversification for a Sales Enablement program. It provides your sales force with a holistic learning experience where they’re equipped and enabled in a half a dozen different ways. Similarly, the best-trained reps have in-person check-ins to gather feedback while also receiving feedback through a sales enablement software (again, like Lessonly).

By diversifying the different avenues feedback can come through, we get a clearer picture of what’s working well, what isn’t working well, and what’s missing. And along the same lines, feedback gets to continuously define the true picture of your entire Enablement program.


3. Flexibility is Necessary for Rapid Development of New Sales Reps.

Every rep learns differently. Every rep learns at a different speed. Some reps ask loads of questions, and others don’t seek clarity enough. Some reps begin their onboarding the week their coworkers are on vacation. Others start two days before the 4th of July when half of the office, and key stakeholders in the onboarding, are out of the office. Maybe peer or mentor shadowing is key to your onboarding, but most of your top reps are OOO visiting prospects in their territory when a new hire starts.

All of these scenarios have happened at Lessonly while onboarding pre-sales and post-sales reps. Regardless of the situation, the ability to adapt to what the rep needs has been pivotal.

Flexibility is part of what swings onboarding and rep development from bad to good, or good to great. And listening to what the reps say they need (feedback!) and implementing the changes demands flexibility.


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