Episode 198: Sharif Wilson on How Enablement Can Impact Sales Strategy

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Shawnna Sumaoang: Hi and welcome to the Sales Enablement PRO Podcast, I am Shawnna Sumaoang. Sales enablement is a constantly evolving space and we’re here to help professionals stay up to date on the latest trends and best practices so that they can be more effective in their jobs. Today, I’m excited to have Sharif Wilson from Forter here join us. Sharif, I would love for you to introduce yourself, your role, and your organization to our audience.

Sharif Wilson: Hi, how are you doing? It’s really a pleasure to be here with you, Shawnna, and the audience. As you’ve said, my name is Sharif, I currently work at Forter as a global sales enablement manager. Currently, our company works on creating trust within the e-commerce space, working to fight growing complexities and abuse and fraud within the e-commerce space, and creating a more seamless customer journey on the web. That’s currently what I am doing at Forter, helping the go-to-market team strategize and build out ongoing education, keep our reps sharp, and constantly growing the book of business.

SS: Well, I’m excited to have you here with us today. On Linkedin, you caught my eye because you had shared a quote that said measurement is the first step that leads to control and eventually improvement. In the context of your sales enablement efforts, how does measurement help you optimize your programs?

SW: Well, measurement helps you to see what’s working and what’s not working. I think in the sales world there’s a misconception of going strictly off of gut, strictly off of impromptu notions of, “hey, this worked at this company or this worked in this industry”. There may be some credibility to that for sure, but I think if we really want to systematize and create programs that can scale and that can be repeatable, we need to see what the metrics are bearing forth. Until we’re able to measure something, unless we’re able to analyze, there’s no way for us to control, there’s no way for us to credibly say that we’ve improved anything. It was actually a quote that I had read in one of the sales books that I feel like was really great. My manager actually passed it to me when I first started this role, “The Qualified Sales Leader” and that was just so impactful to me.

SS: Absolutely, now to double click into this, what are some of the core metrics that you use to measure the success of your enablement efforts?

SW: Yes, so it’s a little bit double-fold. At the end of the day, sales is measured by revenue. How much revenue is that team generating? That’s kind of one of the core purposes of that organization within any business is to grow the bottom line. I think from one standpoint, you want to have an eye on how the sales organization is doing in general, how well they’re doing as far as gaining new business opportunities, creating new opportunities, creating new conversations, how long is it taking from initially meeting an opportunity to bringing it within to the business community as a customer.

On one end, there’s looking at the revenue, and then on the other side, you want to see what the adoption is like to your actual training internally. There are a ton of different LMS tools, learning management systems, that teams can use. Also, looking at how the programs you’re actually creating, how are the people within your organization adopting them? Are they doing them at all? You want to see how people are adopting your programs. If there is a correlation between when you rolled out these programs with the bottom line, sometimes sales directors or VPs, people in the field will bring up things in real-time and you’ll have the opportunity to create programs in response to a real-time challenge. Being able to measure if your program has actually had an impact on that specific challenge that was brought up to you is important.

SS: You’ve touched on a lot and with so many potential metrics to measure, how would you say sales enablement practitioners should go about really prioritizing and determining which are the right metrics for their business?

SW: It’s my opinion that the sales enablement organization is a part of the sales strategy arm within a business. The bottom line is we want to sharpen our reps, we want our reps to be more equipped, and more able to scale time from discovery meetings to close. We want to shorten that gap, we want to increase revenue. I think all the metrics that we’re looking at have to be tied to is this having an impact on the bottom line? Is this having a positive impact on the bottom line? Is more revenue being created? Are more opportunities at the end of the day being created? Are reps shortening their time from discovery calls to signed contracts? That’s the end goal. I think the metrics that we look at have to be tied to that.

Different organizations measure metrics based on how different opportunities are progressing. There are multiple stages to awareness and different companies measure that differently. Some have numerical stages, some have alphabetical stages. At the end of the day, it’s the same thing. We’re trying to see how long it’s taking specific opportunities to go from one stage to the next and ultimately hopefully a signed contract. I think that it’s important to make sure that anything that we’re looking at is serving that purpose. I don’t think there’s any metric in the sales enablement field that is, in my opinion, more important than that. We should be positively affecting the bottom line, growing our business, growing logos, causing our reps to be able to shorten the time span on our activities to reach their ultimate goals.

SS: Absolutely. Now, with all that said, enablement often has to work rather cross-functionally, especially across the go-to-market teams. Who are some of the core stakeholders that sales enablement should really partner with to define the right metrics for the organization?

SW: That’s a good one. I know different organizations are made up a bit differently. At my former company, the sales enablement program rolled up under the education department and now we’re under the sales operations department, so that colors things a little bit differently for us. In my current role where we’re heavy metrics-driven, our main stakeholders are VP of sales ops. I think that’s an important place and I think it’s a proper emphasis, but I think that’s maybe one of the main stakeholders that we want to be looking at, sales ops, the people who are in charge of the forecasting in charge of all of the metrics. How long are our deals hanging around within the pipeline? How are the different reps doing? They’re the ones creating a lot of the dashboards that are visualizing how the sales operation is actually progressing.

It’s able to give, in its best state, an accurate depiction of what’s happening in the field and in a very measurable, concrete, and black-and-white way. We’re able to draw nuance from the metrics that they provide. I think sales operations, no matter where the sales enablement department follows, you have to have a close relationship there. There’s got to be a regular cadence. There’s got to be a strong bond there.

From there, I think sales leaders and frontline managers, these are great people to be in contact with because you never want to be in a position where you’re just creating programs in a bubble. You want it to be something that’s actually practical and tangible for the frontline managers, for the sales leaders, the VPs, the directors. It has to be something that is relevant to them and something that they feel like addresses their needs. Within any organization, there’s politics, there is a vine for attention as far as what’s the most important thing to focus on and though everybody wants the business to be successful, everyone has an opinion on exactly what to focus on to get to that end.

Sales enablement managers have to be quite diplomatic, they have to know how to get buy-in from multiple different people. You want to have a good relationship with sales leaders as well. I’m talking about frontline managers, directors, VPs who are looking at their regions from different vantage points. I think also potentially product marketing. Product marketing are typically the people who are creating the language and the collateral that the sellers are bringing to market. It’s really important that they are able to have the feedback and an understanding of what’s actually happening in the field as well. I think sales enablement plays an important role as far as doubly on both sides, translating what’s important and how to solve the different issues that are coming up and create that bridge within the organization.

SS: Absolutely. Now, I think a lot of the times when we really start to talk about key metrics, there’s definitely a difference between how those are leveraged. How do you go about using the data that you’re able to gather to really develop and hone in on insights around what’s working and what’s not? Then to take and tailor that conversation back to the stakeholders that we just chatted about, how do you elevate those insights to really communicate enablement impact back to those key leaders?

SW: Yes, so I think it’s really great to start with understanding where your particular business is. Every sales organization is in a different place. There are some things that they’re extremely excited about and there are some things that there’s room for improvement. Whether that is shortening sales cycles, whether that’s trying to break into this particular vertical where there’s probably a lot of opportunity, whether it’s prospecting. There are all different types of things that sales leaders and sales operations will identify as being room for improvement. I think that’s where you want to start. You want to leverage the success that you are having with things that you are doing well and then use that to be able to discern how to crack the code of what you’re trying to deal with. If you’re an organization and you’re trying to get into a different vertical, you want to see how you fared with that so far.

Let’s say you’re trying to get into the manufacturing vertical, you feel like there’s a lot of opportunity there, you feel like there are a lot of customers there. Senior leadership has identified this as a vertical that they want to break into within the new year. More than likely, we’ve had reps try to break into those in general. We want to see what data we have already on that. Who have we already attempted to talk to? How far in those conversations did we get? Where did things break down in that conversation? Have we even been that successful with getting meetings in the first place?

I think trying to discern from that also doing some market research, that’s where the product marketing team is really helpful as well. A lot of times they’ll do market research and they’ll be able to help us with cultivating successful tactics to break into those markets. We will want to use that information to discern exactly how we can break into those areas of the business. If we’re not even able to get a meeting we look into Salesforce or some type of CRM, and we’re seeing that 80% of these businesses that we’ve attempted to get in contact with, like manufacturing, don’t even progress past stage one or, we’re not even able to get a meeting. Well, that means we probably have to work on building curriculum and collateral around something that’s more catered to that industry, where they feel like they can even have a conversation with us, where they feel like we’re even relevant enough to have a conversation with, getting a better understanding of the buyer personas.

That’s a hypothesis, we spend some time looking at that, we work with the product marketing team too to build some tactics, some sequences, maybe some marketing events to break into these markets and we trial it and then we see how successful it is. We build out programs. First, the enablement team wants to see if the reps are taking advantage of the training that we’ve created based on the research we’ve done and teaming up with the different product marketing teams and then we test that. We see, #1, are the reps taking advantage of the training? Then #2, is it being successful? Are we seeing a difference from let’s say, quarter one and quarter two? Quarter one was how things were operating before in quarter two. Are we able to get more meetings? Are we generating more opportunities? Are we getting further along? Is it not doing anything?

I want to go all the way back to my initial thesis: the bottom line of sales, in general, is to grow, the bottom line, is to generate revenue. Different businesses are at different places. Some are early-stage startups, some are real established organizations and they have different goals, but I think sales enablement is always trying to align itself with the growing of the bottom line but also trying to be where the business is trying to seek new opportunities to do that. We take our cues from the ops team and also stakeholders, the leadership, the CEOs, the CMOs, as far as where they see the company going. Then we try to dig into the metrics, teaming up with a product marketing team, teaming up with the sales operations team to hypothesize and try to build out curriculums and trainings and live sessions to equip sellers to be able to achieve these goals that have been set forth for us.

SS: That’s fantastic. Sharif, one of the things that I like to do as a closing question to a lot of these podcasts is really take a look forward. I know obviously, none of us have a crystal ball into the future, but I know that you’ve shared some content around the future of artificial intelligence and as enablement continues to evolve, how do you envision AI playing a role in tracking metrics and really optimizing enablement impact?

SW: That’s a pretty loaded question. AI is pretty much already heavily integrated into a lot of the businesses we see every day. I mean Instagram, Facebook, Linkedin, Amazon, all of these companies that we use daily are already leveraging AI to curate a lot of the things that we see on the internet. It’s funny, nobody’s internet is the same. On my and your computer right now we can search the exact same term and the exact same subject, but our Google search will show up differently based on our user profiles, our identities based on what we’ve looked up and how we behaved on the internet. I find this extremely fascinating.

I think there are a lot of different ways it can be applied. I think AI could potentially generate curriculums for individual sellers. I think a big challenge that a lot of enablement people run into is trying to create that one-size-fits-all curriculum for everybody. Everyone learns differently. Some people like videos, some people like to read, some people just like to watch other people do things. Some people want a mixture of it all. There are so many different learning styles, so the challenge is always how to strike that balance, where AI potentially could have a software that assesses different people’s activities, some of their different selling activities, their learning styles, and potentially create for them, automated in the same way a lot of these platforms I mentioned before. We can have tools that curate curriculums based on maybe a learning assessment. You take like learning assessment, Myers Briggs and all these different types of things, and build you a bespoke curriculum that kind of helps you specifically get ramped up. That’s potentially something that could be created.

I’ve seen LMSs and content systems starting to leverage AI. Let’s say you have a curriculum where you’re trying to teach your team about a new product that you’re about to roll out. Maybe you’ve got a bunch of information from product marketing, you’ve got a bunch of information from your UX designers and your software engineers, but it’s your job to create it into something digestible for the sales team. I forget the name of the LMS, but what it enables you to do is upload a bunch of information. It didn’t matter if it was videos, random notes, or audio. Essentially what it was able to do was create a beautiful curriculum out of that information, like generate a narrative out of it. I found that to be quite fascinating. I have it written down somewhere, but that’s the type of stuff that we’ll probably be seeing more and more within the enablement world, which can actually probably free up enablement professionals to be a lot more forward-thinking and strategic if they’re able to have more leeway with tools that can take up some of the harder things to think through a lot of the times when it comes to pragmatically rolling something out.

SS: Absolutely. I love the potential though that it is there with technologies, so it’s an exciting future to look forward to. Sharif, thank you so much for your time today.

SW: Thank you.

SS: To our audience, thanks for listening. For more insights, tips, and expertise from sales enablement leaders visit salesenablement.pro. If there’s something you’d like to share, or a topic you’d like to learn more about, please let us know we’d love to hear from you.

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