Stephanie Benavidez
Table of Contents

Our guest for this episode is Stephanie Benavidez, the Head of Sales Enablement at Loadsmart. Stephanie has nearly 17 years of experience in various roles, from launching new verticals from ground zero to overseeing the GTM strategy for new products and services and implementing processes across businesses that redefined how each company operates. As a former Girl Scout, Stephanie’s motto is to be always prepared.

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

Enablement as a strategic function

When appropriately positioned, sales enablement is a strategic function in an organization as it directly impacts the business. Support has a connotation of reactivity. If a support ticket flies out, we must react. 

Clear asks emerge when we position enablement as a strategic function in alignment with the C-Suite. This includes:

  1. What are the KPIs we want to impact this quarter? 
  2. What are the goals? 
  3. Are we trying to roll out a new product? How are we positioning it? 
  4. Are we trying to bring in more stickiness to organizations and cross-sell? Can we track that? 

Enablement can contribute to these efforts by creating better collaborations between multiple teams so that they can cross-sell better. Reporting the key findings that you're discovering is imperative. This could include the gaps in the sales cycle, the impact of training completion, the specific tools/tactics you use to help sell better, and so on. 

Leaders will only know what is happening if these insights are brought to the forefront. They will simply look at, “Did we close X, Y, Z company in X, Y, Z time?” 

Being proactive should consistently be the theme of enablement.

When enablement is reactive, reps may react negatively, often after receiving feedback. For instance, enablement leaders may listen to a sales call and point out the rep’s mistake. But is that a theme for that rep, or is it just during this one call? Reps feel enablement needs to coach them on their weaknesses, not their mistakes.

However, if we look at 15 calls, and the rep is constantly making that one mistake, maybe they aren't framing articulate questions and putting the ball in their buyer’s court. This means your reps aren't leading or guiding the buyers. That's an area for a coaching opportunity.

Defining success for the C-Suite

Improving the value of enablement to C-level executives requires trying new things and seeing what works. When charting strategy or new metrics, something that has worked for me is taking a pilot approach. For instance, if you are trying a new tactic, take different cohorts, A and B, who will try the new pitch or cadence. This provides room to figure out what works and doesn't.

With many companies having a global presence, the sales teams are different, as are their sales cycles and how they sell. When supporting multiple sales teams, enablement must meet everyone’s needs. 

One way to do this is to create more tactical boot camp classes focusing on competencies and skills versus methodologies. “How are you overcoming objections in this market? Let's go through some coaching.

Have periodic round tables where high-performing reps bring their experience and expertise and engage with newer sellers. This is a great way to build good relationships between two cohorts of people. The idea is to create multiple ways to double down on the required skills and competencies.

5 Best Sales Memes of 2020 to Keep You Motivated

Selling in today’s economy is challenging. Before this, reps sold in a high market when people had money to throw around. But, the same strategies and tactics that worked a year ago don't work today.

Considering the current economic landscape, we put on a boot camp on what sellers can do to avoid burnout. This focused on small, tangible ways reps can continue to be positive and what managers or colleagues can do to help. Most reps today are working, wondering where their next meal is coming from because pipelines are challenging to build. However, persevering and selling through these tough times will foster talent who thinks outside the box, go above and beyond, and do things they would not ordinarily do. 

Make coaching fun

Enablement is typically rallying your troops.  Nobody wakes up ready to learn. One of the things I looked for when hiring my team was that we needed to bring the energy to be our cheerleading squad. For instance, if you're organizing a boot camp and the enrollment is low, talk to your reps. “Are you busy right now? Nope, you aren't. Come on; we are meeting for 30 minutes.” Reps can spare 30 minutes to learn more about what they are selling. 

After all, enablers are selling internally. 

Different jobs require certifications or continuing education credits, with a minimum of ‘x’  hours to fulfill credit requirements. We are working on building a gamified training program, ‘Accelerate,’ where reps want to engage. This will have a required component, and reps must engage in two required skill or competency training each quarter. Smaller components that play into psychology and behavioral science include carrots, where they get points that can be redeemed or a leaderboard that allows for conversations.

You can't impose training or education onto somebody, but you can try to pitch the training in a way that appeals to them. Consistently check in with your reps and discuss their goals and motivations. They will eventually start coming to the training of their own volition. 

For instance, we organized this email effectiveness workshop and informed that it would be a collaborative workshop and that there were limited spots. It filled up within 15 minutes. We told them we would dissect their emails to see what works and what doesn't. My team was over the moon because ‘X’ signed up, and he had not wanted to come to any workshop before this. 

We had such great demand; we will be holding this workshop again. Now, when I look at the registrants for our past and future boot camps, it consistently includes reps from high-performing cohorts.

The next step is having your high performers facilitate workshops or training and have them own a training component. This will cause intrigue from other reps. When reps take ownership, it is a contributing factor because when somebody owns something, they are likely to be more involved. “What are you doing? How do we become part of this?” Enablement needs to get scrappy and inventive, and create incentives.

The end goal is to have reps learn a thing or two and be able to apply it to their day-to-day role.

Role of enablement today

The changing consumption in sales has led to companies buying less than they were and hiring fewer sales reps than they had planned. 

Apart from hiring halts, several companies have also made the mistake of not retaining their sales enablement teams or reducing them significantly. This has left enablement with a different responsibility and focus from a year ago. While the focus before was not entirely on onboarding new reps, it was a significant portion. 

Our responsibilities have evolved with the current economic scenario over the last six months. For instance, I adopted two sales trainers when I started at my current job. I was tasked with building the strategic vision for the organization, including the different roles and responsibilities. I used to have sales coaches on my team. Our biggest concern then was what we would be doing beyond onboarding. 

Today, it’s just us Three Musketeers in the trenches together. Now, enablers must step into a sales coach role where they will hit the floor more often and facilitate effective coaching. 

The niche functions can't get by doing just that. While we were onboarding new reps, the capacity was different from what it was earlier. When I first joined, we had 40 to 50-person classrooms every month and needed help to keep up with hiring and onboarding. 

We were hamsters on wheels for a bit!

Most companies aren't doing large-capacity headcount hires in the current economic landscape. For instance, at Loadsmart, we strategically hire enterprise-level reps with X amount of experience. We work with them, showing them how the tools work, the pitches, the products, the final process, etc. As for sales coaching, we've told the reps and the managers that while our sales coaches were doing daily and weekly check-ins, enablement doesn't have the bandwidth to do that any longer. 

The skills boot camps and more extensive training programs still involve product rollouts. This is a big component of our responsibility and what we deal with today. However, that might change with time.

We are willing to roll up our sleeves, grind and do whatever is necessary to make the business successful. My team has had very frank conversations about it. We will do it, whether building the content, getting on the floor, or being silly and hitting a gong to tell people to come to the training room.

During economic downturns, companies should double down on retaining and training talent to be as precise, productive, and efficient as possible. For instance, we did an internal exercise where enablement practitioners met with their high-performing group and built success profiles to understand how and why they are successful. 

Every single person in your high-performing cohort will still have opportunities for improvement. They could be using a system inefficiently. They may need to learn about features or functions that save an hour daily. If this is your high-performing group, imagine the improvements when you do this exercise with your mid-range and low performers. 

Here is something you can do: 

  1. Outline the competencies, skill sets, or matrices for every IC level 
  2. Create scorecards
  3. Have the sales coaches observe, shadow, and identify everyone individually
  4. Create gap analyses from an aggregate level to identify trends 

This will allow you to recheck if something was missed during rep onboarding, negotiation tactics, CRM hygiene, etc. There could be 15 different metrics you are assessing, but ultimately, it all comes together to allow you to create content and training programs that meet people where they are. 

In today’s landscape, live training won't always be possible. An alternative is to provide periodic bite-sized tips that can be dropped into your Slack Channels. You aren't reinventing the wheel but maintaining ongoing training and allowing reps to understand they are doing their job well.

With many enterprise reps and other reps strategically located around the globe, meeting people in different time zones is challenging. There was a need for a system that could provide on-demand learning because, typically, everything was delivered live, in person.

For instance, there have been times when reps were on calls for eight hours, and it was 2:00 AM where they were. 

The likelihood of them focusing was sub-zero. That would have been a terrible experience for that rep, not just from an onboarding perspective. Are they going to retain this information? Is there anywhere for them to go and find it again if needed? An LMS was one of my priorities, as is often the case for most enablers upon joining an organization. 

The sales rep is your customer 

Often, there is not enough communication or collaboration between teams. In the case of enablement and product marketing, the customer is the sales rep. While both functions don't need to be the same job, being in lockstep with each other is essential. RevOps is also integral to enablement because they provide you with the systems, the data, and the analysis of what's happening.

I spend a lot of time with Product and RevOps. But meeting the stakeholders, with the different teams, making sure that there are no silos, all of this was a job in itself. For instance, we launched a new product last July, and Sales Enablement was tapped on the shoulder four weeks before it hit the market. “We heard that you do training for sales. We should probably talk.”

We banded together as a team and worked very hard to try and ensure that we aligned everything in terms of the assets and training. 

Was it the best launch? No, I don't. 

We did a retrospective, and truth be told, product marketers should not be facilitating demos. Everyone on my team didn’t feel as comfortable facilitating a demo. It was an interesting launch, but we had an opportunity many months later to do a relaunch in a much more concise way where we were in control, but everyone was giving us the pieces we needed to be successful. By then, they knew what sales enablement was responsible for influencing and selling the reps how to sell the products.

Enablement is more than getting in front of a room and showing the features and functions or a slide with a detailed list of who else is selling something similar.

The first 90 days

Some people believe enablement is hyper-focused on onboarding. Others think it is another word for training and coaching, while others might say something else. If you're just transitioning into enablement, it’s important to have clarity on what you must prioritize. 

A book I read years ago when I first got into management was called ‘The First 90 Days.’ It was all about how to approach your first 90 days in an organization and where you should spend your time. When I joined the organization, I wanted to immerse myself in the business as much as possible.

I had my fair share of meet-and-greets with stakeholders. It was often met with confusion on what sales enablement meant. I ended up selling enablement in these meetings. “I'm so glad you asked. I can't wait to tell you what I plan to bring to this organization.” Meeting with the different reps from various teams that sell multiple products, Customer Success Managers (CSMs), etc., and understanding their customer journey was integral to this journey. 

Always be prepared!

Why are people buying from you? What are we solving for? Why do they care? Why are we different?

Work with the CSMs first. Understand who the target demographic is and then go back, meet with the reps, and understand from entry point A into the organization until all the way through. Is this working as fast as it can? Are we selling in the right way? Are we saying the right things? How is what we are selling upfront landing in implementation? Is it how you envisioned it?

During the meet and greets with the stakeholders, introduce yourself, and make it known what sales enablement is and what you plan to build. That's a great start. Then, create your charter, the vision, and the strategy of what you plan to influence. What are the goals that C-Suite is looking for? Build your charter off of those goals. And throughout this process, don’t forget to collaborate with your stakeholders. That is the key to success.

Feel free to tune in to this interview on Spotify or Apple Podcasts. If you prefer other platforms, simply click here to explore more options. Happy listening!

About the author


Stephanie Benavidez

Stephanie Benavidez is the Head of Sales Enablement at Loadsmart.

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