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How to Start a Career in Sales Enablement [Misha McPherson Q&A]

Sep 24th, 2019

As more companies invest in sales enablement, there are (naturally) more people with the word “enablement” in their job titles.

In fact, CSO Insights found that the number of companies with a dedicated sales enablement leader or program tripled between 2013 and 2017. So it’s safe to say that sales enablement roles are hot right now.

As with anything new, there are bound to be a lot of questions of interest in sales enablement as a career path. For more insights into this topic, we spoke with HumbleGritSales CEO Misha McPherson, who has more than 10 years of experience in senior or director-level sales enablement roles.

For the latest Q&A in our ongoing blog series, "Sales Enablement Voices," McPherson shares her thoughts on starting a career in sales enablement, what first-timers should know about most roles, and how they can get up to speed quickly.

Previous Editions of Sales Enablement Voices:

Why should someone pursue a career in sales enablement?

Sales enablement is an incredible career path, but it’s not for everyone. I sometimes see people go into sales enablement because they think it will be less stressful than being a quota-carrying sale person, or because they see that it’s a hot job right now. Those tend to be the people who don’t stay in sales enablement for very long.

The people who should pursue a career in sales enablement are the people who love constant change, solving complex challenges, and above all, love sales. They need to be natural collaborators and great negotiators. Sales enablement is a hard job, and it’s downright impossible if you don’t have a passion for it.

What are some common misconceptions about sales enablement roles?

That it’s easier than sales or product marketing. Or that it’s all fun and games. If you are a salesperson who’s interacting with sales enablement, you might notice that we’re usually pretty upbeat – and they assume that’s because our job is fun! It’s important to understand that sales enablement is a really hard job.

There’s a misconception that you don’t have a quota. But you’re moving from a quota to KPIs, which are just as important to hit quarter over quarter. Our goals are similar to those of a CRO or head of sales.

There’s a misconception that you don’t have to have a sales background. I see a lot of people who are coming into sales enablement from sales development, product marketing and L&D roles. I think it’s really important to understand how to close deals in order to be a great sales enablement leader.

That said, just because you are an SDR, for example, that doesn’t mean you can’t go into sales enablement in the future. It’s just important that you spend some time learning about the sales process and what really is needed to close opportunities.

Why is it so important to have closing experience in sales enablement?

If you just approach sales from a scholarly perspective, sales should be super easy. You do this and that, the deal gets closed, right? However, anyone who has been in a closing role knows that there are a million things that can go wrong in a sale – things that aren’t necessarily obvious.

Having closing experience helps sales enablement pros uncover those hurdles and teach reps to dodge them before they happen.

One of the things I always encourage: learn how to be positive but paranoid.

What might go wrong? What might be missing? What are the hurdles that we have not uncovered yet? It’s to make sure they’re always ahead of the curve when they’re prepping for those buyer interactions.

Does moving from quota to KPIs require a shift in mindset?

If you are not being measured on ways that you are increasing revenue or decreasing operational costs, that is a big red flag in my mind. You have to be tied to those numbers if you want to get a seat at the table. If you’re not tied to increasing revenue or decreasing cost, then you’re likely to be seen as a cost center.

Sales enablement leaders should have multiple partnerships throughout the company, and one of the important partnerships to have is with sales ops. I lean on sales ops to get me interesting data, and use it to put different programs in place to try and change the behaviors of the overall sales team.

Related: Sales Operations vs. Sales Enablement: Better Together

Are there common knowledge gaps for new sales enablement leaders?

Anyone who’s coming into sales enablement should know that no matter what their background is, they’re going to come in weak on something. I often meet new sales enablement practitioners who almost feel apologetic about what they don’t know. We’re all weak on something, and the important thing is to focus on learning.

Whether you’re weak on instructional design, sales, marketing, understanding things like recruiting and hiring profiles – everybody’s going to have a strength and a weakness. I see it across the board. Most commonly, I see weaknesses in instructional design, because sales enablement leaders often come from sales and marketing backgrounds.

If they come from sales, they typically are less strong on messaging. They might understand what bad messaging looks like, but unless they have worked with a great marketing team before, they might not understand what ‘great’ looks like.

If they come from marketing, they typically don’t come with a strong enough sense of empathy for the sales team.

For example, you might see new sales enablement people setting up trainings at the end of the quarter, which is one of the big no-nos. Do not ever do that!

It’s understanding what your background is and how much ground sales enablement covers. That really helps you figure out what you should focus on.

Does the type of the sales enablement team you join make a difference?

There’s a huge difference between joining a company as an ‘army of one’ versus a large sales enablement team where you’re working on very specific tasks.

For example, you may not need to learn much about messaging, buyer personas, competitive intelligence and hiring profiles if you’re working as a sales enablement coordinator in a large, balanced team.

It’s all about understanding what your objectives are for your role, what your background is, and – my favorite part of sales enablement – knowing that you have to constantly be learning.

What resources might help a new sales enablement practitioner?

My favorite recommendation is LinkedIn. Look up other sales enablement practitioners in companies that are of similar size, but not in the same competitive space, and send them a note.

Sales enablement tends to attract people who like to help. For the most part, if you reach out to another sales enablement person and say you’re brand new and want to build up your network, most people will say ‘yes’ and meet you for a virtual coffee. You’ll learn more from that than just about any other resource out there.

Figure out which areas you need to get stronger on, and then start studying it the way you would study any other subject. I’ve been in sales for 20-plus years, but I still read sales books and articles on a regular basis.

You will get so busy with your job, and it’s really easy to not give learning the time and attention it deserves. Get nerdy with it, put it on your calendar, and stick to it.

It’s about continuing to learn what’s working for other people and getting a good understanding of what success looks like.

Any other ways someone can ‘get nerdy’ with sales enablement?

I run a workshop: SaaSy Sales Enablement. It’s a two-day workshop focused on director-level topics, and it’s specifically designed around how you tactically run sales enablement internally.

It’s everything from how you build a great onboarding program, how you run sales kickoffs, how you scale out your sales enablement team, and how you prioritize the activities that are going to have the most impact. It also covers how to get buy-in from executive level and across the organization and below, from the reps.

What’s one productivity hack you use to make your life easier?

I put flipchart paper all over my walls and put small Post-it notes all over them. That helps me more than anything else because it’s so easy to get down into the weeds.

A good onboarding program, for instance, might have anywhere from 100 to 150 components – like courses and certifications. These programs are huge. How do you physically get your brain around 150 different moving pieces? It’s got to be visual; nobody’s got a screen that big!

Where do great sales enablement leaders come from? Download this Brainshark special report to learn more!