Shara Simms
Table of Contents

Shara Simms is the Director of Global Sales Enablement at Cloudinary, a media experience platform for developers, creators, and marketers looking to manage, transform, and deliver images and videos online.

In this interview, Shara discusses the ROI of enablement, best practices to leverage AI, and how to drive knowledge retention.

(This conversation has been edited for length and clarity.)

Elevating enablement

Sales enablement leaders and professionals often act as the glue that connects all the moving pieces and projects at a company. They translate incomprehensible noise into sales language with the partnership of other departments, such as product and product marketing teams. However, at startups or companies experiencing a lot of growth quickly, there will be many competing projects from different areas around the company.

Unfortunately, a clear line of sight from sales to everything happening is not always there.

You need a good strategy around sales enablement to act as a blocker for the noise and bring clarity to competing priorities and projects. This requires determining the most impactful information that will trickle down to sales and how to deliver that to them.

You can't have people reaching out to sales for every project or priority. You need someone with that big picture and a deep understanding of what's happening across the company. They can leverage this knowledge, translate it for sales, act in a critical role, and be the liaison between sales and everything else happening.

The ROI of enablement

Whether enablement or another role, ROI is always significant. The first thing you need to align are the KPIs (Key Performance Indicators) or the OKRs (Objectives and Key Results) from the top down to the company metrics. For example, is the company looking to increase velocity in closing deals? Are they trying to get everyone in the company or the sales team on point with the same message for their sales play or pitch? Is it product knowledge? If there's a new product launch, what are the quarterly or yearly goals of the company, and how can you align with them?

From there, it’s critical to consider the individual roles you support in the sales teams. For example, the competencies and tasks of an SDR (Sales Development Representative) will be significantly different from those of an AE (Account Executive) or solution consultant. When talking at a high level, you must ensure you have measurements specific to the role.

For instance, we are building AI simulations and testing the sellers to prove ROI internally. You have to start with a baseline. Can they navigate through these different scenarios? How well do they navigate these scenarios on day one versus a quarter down the line? You need to have diverse simulations for different roles; it's essential to show you are moving the needle and that sales enablement helped reps make improvements from the baseline.

Talk to your sales leaders and start with this baseline:

  1. What's their perception of their skill level?
  2. How would they rate themselves?
  3. How do the sales leaders rate their team?

Now, let’s assume they go through your enablement program. Do you see that uptick from your baseline a quarter or a year down the line?

You can't prove the ROI of enablement if you don't start there.

Enablement, engagement, and effort

One tactic is to look at sellers actively engaged in your enablement programs. Are there individuals who completed your curriculum? What do their sales cycles look like compared to those not actively engaged? Do you see a difference between those actively engaged and those not? With ROI, there will always be manual effort. It will take some work to do that measurement.

As for core competencies, the first thing is to get everyone on a baseline. All your reps need to be able to do basic things like discovery. Everyone also needs to be able to do value selling. While basic skills are agreed upon within the teams, there will be individuals who are exceptional in one area and struggling in another. It's vital to align closely with sales leaders to understand the core competencies they are worried about.

The next step is to do a gap analysis. What is the gap that you are seeing currently? You need to direct your efforts there. For instance, you are focusing on discovery internally. How do you show that your time and effort have made an impact?

Put your time and effort into getting your sales reps to do discovery calls competently, effectively, and efficiently. You are now getting a measurable impact and value that you could bring. This will shorten your sales cycle and increase the sales velocity because you will uncover pain points, talk value much sooner in the conversation, and align with the sales leaders on the gap right now.

Are you focusing on discovery? Are you focusing more on technical skills? Do your solution consultants need more specialized training? Suppose where they are lagging is in the demo portion; there are a lot of numbers and metrics behind it. You need to do a gap analysis and determine your focus. Then you can turn around and say, “On average, stage two typically lasts 60 days. Now, stage two lasts, on average, 40 days. Maybe it's not a direct correlation, but we can prove an indirect impact there.

Goal setting and buy-in

While there will be excellent sales leaders who you don't have to work too hard, buy-in can still be an issue. A tactic that works well is remembering that enablement is not just about training.

We must assure our sales leaders and partner with them on enablement being more than just trying to deliver training to them. We are not trying to take time away from sales. We are trying to make the best use of their time. This could be a training or a curriculum. Or it's looking at the available sales tools and partnering with operations to figure out how to go deeper into these tools and identify areas you could utilize more efficiently.

It could also be partnering with your data team and figuring out if there are ways to automate pulling data for the team so they are doing less manual work and can spend more time selling.

Once you get into the mindset of realizing that enablement is not just training, there are so many things you can do to help sales teams manage their time efficiently. That's when you start the partnership with sales leadership because they don't see you as a trainer coming in to take time away from selling and go through an hour-long webinar. They see you as a true partner trying to free up sales time and make the most impactful and efficient use of their time.

Enablement beyond onboarding

In times of less onboarding and hiring, sales enablement increases their value. Under normal circumstances, onboarding is necessary, and a lot of rigor, time, and effort should go into it. But when you do onboarding, you need to make it scalable. This makes it repeatable, and once you get to that point when you are not hiring as much, you can focus your attention elsewhere. For instance, areas that you only had a little time for before.

Some of the things that we are working on now include mentoring programs. Whether you have the most seasoned or newest rep, there will always be opportunities to learn from each other in different skill sets. Some of our SDRs are jumping on AI technology to use their time more efficiently. We want to start setting up some of our more senior or tenured reps to sit and learn how they use these tools to make it more efficient for them.

For instance, your up-and-coming account executives (AEs) are partnering with tenured AEs to learn the ropes. This could look like setting up mentorship programs. Whether your reps have been in the industry for two decades or are brand new, they should always be looking for ways to improve and grow, and those are the skill sets that we can start to hone in on and help out during these times.

In addition, hiring is low in many companies, with stringent budgets for tools and tech stacks. Sales enablement can say, “Let's look at our current tech stack and tools. What are we not using most efficiently?

In the current AI trend, many existing tools are adding AI integrations that don't cost extra. However, most companies are not yet taking advantage of these opportunities.

Suppose you are at a company that says, “We don't have a budget for these new tools, and we are not investing in new enablement.” Look at your tools. Many popular tools are building new AI integrations that could increase sales. You don't have to spend money on a new tool in all cases. That's another area we are focusing on right now while we have the time to look at our tools and build them to be impactful.

There are dozens of sales technology tools on the market today, which can bog down sales reps. This is where enablement needs to focus. Is consolidation possible? Can reps use a single tool to do something that typically takes two tools?

Besides training, IT enablement makes work easier for the sales rep, whether in getting the knowledge or the processes. Eventually, you will save time for the sales rep, and they will be more productive spending that time selling. Enablement can focus on all these things and prioritize them.

Driving knowledge retention

Adults learn in different ways. While some people are visual, others have to read, and another section of people have to write information down to retain it. With the different ways the adult brain learns and retains information, there will never be a one-size-fits-all learning program.

You need to offer information in a variety of ways. For instance, whenever we develop a new training curriculum or course, we always try to provide it through different modes. We will have a live interactive session where people can ask questions and be engaged. We will have a guide that comes out afterward that summarizes everything we did so people can read it. We will also do quizzing a week after the information has sunk in to ensure it's retained.

Ideally, there would be 30, 60, and 90-day follow-ups on specific topics. This ensures that information is retained after 30, 60, and 90 days. It’s crucial to get a cadence going for certain topics. This requires identifying specific skills or knowledge that need to be refreshed every year.

It could be a sales pitch certification or product knowledge because products constantly evolve. Getting a cadence going where it's more than just a one-and-done is essential. Suppose reps have taken the training, read the material, or go through a role-play scenario. You must do it again in 6 months, with a slightly different flavor, to ensure you retain the information. Reinforcement is key.

The road ahead for enablement

There's always going to be a need for enablement. People talk about AI and how it will take our jobs and those of sales reps’. There will always be a need for the human element, at least for the foreseeable future. As for the future of enablement, companies are genuinely seeing and continuing to see the value in enablement, which stems from good strategy.

It was unique when I entered training and enablement without any sales background. Today, you can see that trend rising with instructional designers now getting into the space teachers occupy. As the sales industry continues to evolve, we will begin to see that trend with more teachers and people with learning backgrounds entering this space. Taking a chance on people who are slightly new to sales but possess knowledge in adult learning, teaching, or instructional design is a good bet.

Combining that learning background with sales makes a real difference because they can translate information in a way adults can digest.

About the author


Shara Simms

Shara Simms is the Director of Global Sales Enablement at Cloudinary

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