Are You Struggling to Hire a Sales Enablement Leader?

I know… it’s a sensitive question: Are you experiencing challenges in hiring a sales enablement leader? Do you have the feeling that you get too many candidates who are actually more like sales trainers, program managers or sales coaches – not actual leaders who can effectively build and run a broader and more strategic sales enablement team?

I want to address these questions based on many client experiences that show there is no clarity around the “sales enablement leader” role. Even if there is clarity on sales enablement and the fog around sales enablement has been cleared, it doesn’t necessarily mean that there is an equal amount of clarity on what makes a sales enablement leader, especially in how the role is different from more traditional roles such as a sales trainer.

This blog is for all sales leaders who are having a hard time hiring a sales enablement leader. (Click to tweet)

Let’s first get on the same page by establishing a common understanding of sales enablement. Most of you are likely familiar with our CSO Insights definition of sales enablement:

It’s a strategic, collaborative discipline,
designed to increase predictable sales results
by providing consistent, scalable enablement services
that allow customer-facing professionals and their managers
to add value in every customer interaction.

The holistic, strategic, collaborative nature of sales enablement determines the role of its leader. (Click to tweet)

Even if you prefer another definition, one aspect is crucial to understand: the holistic, strategic, collaborative nature of sales enablement. That means if you include in your sales enablement approach more than just sales training (sales content or sales coaching), you create a discipline that’s highly complex and collaborative –  simply because all of these enablement services have to be consistent with each other to be effective. And that requires being strategically aligned to the business and the sales strategy and all existing strategic initiatives. If that’s not the case and you run sales enablement in a project manner, you set yourself up for failure. Sales enablement run in a project manner or on an ad-hoc basis leads to, for instance, win rates of only 39.2% which is way below average performance (Fifth Annual Sales Enablement Study – Available Soon!).

A sales enablement leader essentially is a business leader. (Click to tweet)

Here are some of the criteria you should look at when hiring a sales enablement leader. This list doesn’t claim to be complete; please chime in, and add your thoughts and experiences.

#1: Get clarity on how they approached sales enablement before. (Click to tweet)

This is about getting clarity on whether a candidate managed a set of tasks they were told to manage or whether they actually built and led a new discipline. Did they implement a program they were told to manage and implement? Or did they develop, design and sell their initiative internally, engage senior executives, built a business case and get buy-in before they implemented their initiative?

You don’t want to hear this: “Our onboarding program was too long, so we redesigned and shortened it;” rather, you want to hear something along these lines: “Our onboarding program didn’t deliver the desired results, so we analyzed the situation, assessed the main challenges of new hires, considered our sales leaders’ expectations, redesigned the whole program and got much shorter ramp-up times.”

Datapoint: Our research shows year after year that one-off project, random approaches lead to results way below average performance, this year to win rates of 39.2%, which is 7.2 points below average (Fifth Annual Sales Enablement Study – Available Soon!).

#2: Get clarity on how they considered the business and sales strategy and the particular challenges. (Click to tweet)

Have them share an initiative as an example of their previous work. Ask questions around how they designed the initiative and whether they got deep into the business strategy and the sales strategy. Did they assess the current state of the sales strategy implementation? Did they assess the particular challenges of the sales force? Did they connect their approach to existing strategic initiatives to ensure consistency? Did they design a tailored approach for that specific situation? Did they create a business case? Did they engage their senior executives to sell their ideas?

You don’t want to hear this: “Prospecting was a big challenge, so we were asked to provide new email templates.” But you do want to hear this: “Prospecting was a big challenge in our new markets… bad conversions and lots of leads were untouched by the sales force. First, we talked to sales managers and learned that they paid zero attention to prospecting other than asking for a certain number of activities. Second, sellers felt uncomfortable, had no confidence and avoided it. We created a pilot, developed a new value messaging approach, provided content and related training services, made the sellers confident, and engaged the sales managers and taught them how to coach along those lines. We got much better conversions in that pilot.”

Datapoint: Only formal, strategic approaches that are connected to the business strategy and strategic initiatives lead to two-digit performance improvements: +18.8% in win rates this year; +19.2% last year (Fifth Annual Sales Enablement Study – Available Soon!).

#3: Get clarity on how they ensured adoption and reinforcement. (Click to tweet)

Providing content alone doesn’t drive adoption, as running a training initiative alone doesn’t drive adoption. The sales managers’ involvement, engagement and regular coaching efforts are the foundation of any successful implementation. Even if sales coaching was not their scope, how did they approach this challenge? Did they engage their sales managers in one way or another? Did they integrate them into their initiative?

You want to ask questions related to the examples above to better understand whether the candidate was aware of the problem, took action to drive adoption and reinforcement in different ways, and ideally engaged senior executives to initiate better involvement, engagement and collaboration with sales managers.

Datapoint: Only sales methodology and process adoption rates above 75% resulted in above-average results for revenue plan attainment, quota attainment and win rates (Fifth Annual Sales Enablement Study – Available Soon!).

#4: Get clarity on how they measured sales enablement success and delivered results. (Click to tweet)

Listen for answers such as, “We know measuring sales training success is hard” or “I always managed my budget and delivered on time and with the desired quality.” Then ask questions to better understand their stakeholders’ expectations and how they were measured themselves. Ask questions to better understand a specific initiative they were running, how they specifically measured its success, how they justified their budget and how they communicated that internally.

You want to listen for answers such as, “We had a hard time figuring things out, but we created a dashboard of leading and lagging indicators per initiative to ensure that we always saw early on if we were doing the right things – and that we also saw the impact on lagging indicators for our stakeholders.”

Datapoint: Only 24.0% of organizations are able to measure the ROI of their sales enablement investments (Fifth Annual Sales Enablement Study – Available Soon!).

#5: Get clarity on their ability to collaborate effectively. (Click to tweet)

Finally, you want to get clarity on their ability to collaborate across functions (e.g., marketing, sales ops, product management, IT, etc.) and how they have set this collaboration up to ensure consistency, efficiency, effectiveness and scalability. Here, it’s important not only to look at personal capability but also to look at the ability to lead various functions – often with less than dotted lines – based on such a collaboration model to successfully deliver the expected enablement services.

Datapoint: 76.5% of SE teams collaborate in an ad-hoc manner or only informally (Fifth Annual Sales Enablement Study – Available Soon!).

Hiring a sales enablement leader as a business leader is not an easy thing to do, as there typically is still too much fog around the discipline itself and the role. Please chime in, and add your thoughts, experiences and additional criteria.

If you haven’t already, take a look at our book Sales Enablement – A Master Framework to Engage, Equip and Empower a World-Class Sales Force. It contains lots of valuable information, frameworks and approaches to make you a better sales enablement leader.


Questions for you:

  • What exactly is the role you want to hire for: a sales enablement leader or a manager of programs?
  • What’s your vision for sales enablement in your organization?
  • What are the specifics you want to see in a sales enablement leader?

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  • Andrew Treharne
    Posted at 21:31h, 16 September

    The blog raises some interesting and important questions. I think it ‘mazing’ at the number of Sales Enablement people who have never been in sales, let alone sales leadership. They have never walked in the shoes of sale people or sales leaders! #salesenablement #salesleadrship #salesenablementleadership Great article – thanks for sharing!!
    Its sort of like a Sommelier who doesn’t drink wine!

  • Tamara Schenk
    Posted at 11:03h, 17 September

    Thanks for your comment, Andrew!
    That’s a great analogy, a sommelier who doesn’t drink wine. Yes, it doesn’t build credibility.
    Best, Tamara

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