InsightSquared went through a lot of changes this Fall.

We moved offices from Cambridge to Copley Square (from North of Boston to the center of Boston, if you don’t know the area), we made a bunch of new hires, and we began the process of revamping our entire go-to-market strategy. As part of that revamping, I moved from my role as a content writer into a brand new sales enablement role.

This post is the first in a series to document what that transition looks like. Sales enablement is like the theory of relativity — everyone has heard of it, but no one can really explain it in a way that makes sense.

My goal is to provide other companies with concrete experience from a company that is building a sales enablement role from the ground up. Hopefully, by sharing my experiences as I learn the ropes of sales enablement (I’m currently 1 month into the job), I can shed light on what the actual execution of sales enablement looks like.

The best place to start is to explain why InsightSquared decided we needed a sales enablement function in the first place. This story will touch on a lot of challenges you’ll be familiar with if you work in the B2B SaaS space.

Where we were in August

If you rewind a few months, the state of the world we lived in was one that is familiar to every B2B company. Marketing was generating thousands of leads, but many of them weren’t our target buyers. That left a lot of work for the sales team to sort the good leads from the bad, and then track down relevant contacts at the companies they actually wanted to sell into.

On top of that, the marketing team relied heavily on a mass-email marketing engine that was starting to wear out. A lot of people were signing up for the emails, but we weren’t doing a great job of identifying which of the leads we generated would actually turn into buyers.

I’m painting with very broad strokes here, but essentially we weren’t winning many deals that were driven across the line by a single internal champion — it was always a group decision (not surprising, given the trends in B2B sales). The problem was a misalignment between what we were incentivized to do and what we actually needed to be doing.

The result was a whole lot of leads, but not as many quality opportunities as we needed.

Marketing wasn’t incentivized to deliver a set of key accounts that reps could prospect into, and our reps weren’t incentivized to prospect into accounts once they had them. Instead, marketing was driven by leads, and leads alone, and the sales team was incentivized to spend their time calling the leads marketing produced (side note on terminology – we define leads as individuals within a company, while the company as a whole is referred to as an account). The result, as mentioned above, was a whole lot of leads, but not as many quality opportunities as we needed.

That feeling resulted in a lot of frustration through the whole company, as both marketing and sales saw performance drop.

Starting a Sales Enablement Program

A formal sales enablement role is new territory for InsightSquared — a lot of people have picked up bits and pieces of the full responsibility, but no one has ever done it as a full-time position before that meant the first step to create a sales enablement program was to write a job description to define exactly what sales enablement will entail. Here’s what we came up with.

The goal of sales enablement is to create a framework for reps to follow.

As our product continues to develop and our customer base grows, we needed to make sure our reps were all selling it the same way. The goal of sales enablement is to create a framework for reps to follow as they engage with different types of prospects (all the denizens of Earth, you could say), and to arm reps with the collateral they need to make a persuasive case at each stage of the sales process.

Broadly speaking, that means sales enablement has to fulfill both the strategic role of defining personas, company characteristics, and business cases we should be using within the sales process, while also delivering the nitty-gritty marketing collateral and talk tracks that help build a persuasive sales pitch.

… And that’s about as far as I’ve gotten. Any thoughts on where we should go from here would be welcome in the comments below (I’ve got plenty of ideas, but I’m always open to more)!

I’ve learned a lot in the first month in the new role. Keep an eye out for the next post, where I’ll continue to explain how our sales enablement program is developing, and share a few learns around establishing effective channels of communication and driving the implementation of sales enablement projects.

If your company is facing challenges around sales-marketing alignment and sales efficiency, or if you are considering developing a sales enablement program, I encourage you to keep reading. I’ll be figuring out what works and what doesn’t over the next few months, and you can learn a lot from my mistakes.

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