Episode 30: Sharon Little on Solving Modern Business Problems with Sales Enablement

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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 are here to help professionals stay up to date on the latest trends and best practices so they can be more effective in their jobs.

I would love for you to introduce yourself, your title, and your organization.

Sharon Little: I usually introduce myself by saying that I’m a salesperson at my core. I started, as so many do, setting appointments for salespeople, which is a tough job but a great foundational place for any sales career to begin. I deeply, truly love what I do in sales enablement. I work both for very large tech companies, software companies, as well as very small startups, and I’ve enjoyed every aspect of it. And in sales enablement, I think we’ve just kind of scratched the surface in terms of what we can do and what we can bring to business from a strategic and value-add standpoint. I couldn’t be any more excited to see what the next 10 years bring.

SS: In an excerpt from your book, you wrote that the impetus for sales enablement at most companies is the existence of some failure that occurred pre-enablement, making the case that sales enablement is something that sales cannot live without. In your opinion, why is that the case? What are some urgency drivers for sales enablement, and what problems does it solve?

SL: You know, it’s interesting to reflect back on that comment and just think about where we were with sales enablement at that time. And I think three-four-five years ago, this was absolutely the case. I think it is not so much the case anymore. I think we’re in a situation now where leaders, CEOs, heads of sales organizations really understand the value and the strategic impact that sales enablement can make.

While most of us who work with sales understand that pain is a huge driver for many decisions including buying decisions and org structure decisions and where you invest your money internally within your company, I think that now sales enablement has almost become an aspirational type of investment. Most often when I talk to sales leaders, what their dream is, when it comes to having a world-class sales enablement team, is to have that be the impetus for creating a best-in-class sales organization overall and a selling team that has a reputation in the market of being the very best. So, I think we’ve come a really long way in the last couple of years.

SS: What would you say are the problems that sales enablement, though, is responsible for today?

SL: It’s such a different way of looking at it than how I normally approach it. It is the same set of problems that you will see any sales leader trying to solve. It’s how do I hire and retain the best people, how do I drive productivity, how do I make sure that our culture is maintained and enhanced through everything that we are doing, how do we make sure that our best salespeople continue to choose us as the place to work year after year? All of those things are part of what sales enablement is responsible for, so you really need to look at it from a very human point of view. That is why the sales persona is so important.

I think it’s tougher for folks coming from a marketing or product type of background to lean into a sales enablement role because the persona is not as familiar to them. Now, I will say that there are some folks that just were meant to be in sales and they finally find their home in sales enablement. But really embracing that persona and kind of understanding how a salesperson thinks, behaves, breathes, acts, all of that becomes an incredibly important part for how you approach delivering a successful sales enablement program. Then, if you bring that all back to the bigger picture, there will always be more to do than you have time or resources to tackle.

It’s making sure that you focus on the things that the business is focused on. So, the initiatives that sit at the chief revenue officer level are the ones that you put most of your time and energy into. There are going to be some baseline deliverables and things that you have to have in place for everything else to work, but focus on the broader initiatives, the one that the company is placing their big bets on, and make sure that from an enablement standpoint, you are doing everything to make those successful and it will all work out the way it’s supposed to.

SS: I often hear that sales enablement is the fixer of broken things. I think you’ve heard that terminology before. But what are some of the problems that sales enablement doesn’t solve for and shouldn’t be responsible for?

SL: Yeah, I think this is an important thing to spend some time thinking through a little bit more because we certainly as a business function have had great attention over the last couple of years and you see companies investing more and more in sales enablement, but I think as an understanding grows of what sales enablement is capable of, there needs to also be an understanding of what the boundaries are.

What I have learned overdoing this a number of years is that there are some things that if you try to solve for them through sales enablement, not only will the sales enablement team fail, but you’re potentially just masking problems that exist within the organization that you need to pay attention to in a different kind of way. And most of these things are fairly large. I mean, if there’s not a good vision in place for the business, you can’t solve for that through sales enablement. If messaging and positioning are not in place, that is also something that makes it very difficult to have the same kind of impact with sales enablement programs as you can when sales enablement can connect to broader positioning and messaging within the organization for what it is that they are building for the sales team.

I think the final area that you want to pay attention to closely is whether or not there is a leadership problem. Leadership is certainly very important for the sales team. It is the kind of job that you have to make happen every day, every week, every month, every quarter, and having good, motivational leadership in place is important to create a team that produces at the right level. Those would be the main areas that I would take a look at. Messaging, positioning, leadership – sales enablement can connect to those and be a part of bringing them to life, particularly with the sales persona, but if there is a problem that exists within the company in one of those areas, you can’t address it through sales enablement.

SS: Absolutely. What are some ways in which sales enablement practitioners can set the right boundaries within their organization for what it is that they are responsible for?

SL: Oh boy. Is there a job that has more boundaries than sales enablement? I think that HR is probably the easiest area to set boundaries with. If a particular program applies to all employees, then it belongs to HR. If it applies specifically to rules within the sales organization, then most likely sales enablement should get involved.

The question becomes bigger when you take a look at marketing because there are so many different parts of the marketing organization, and they certainly have a very strong role to play with the sales team. I think that if you take a look at it from an audience perspective again, that is where you can create boundaries that make sense.

So, for example, customer-facing content belongs within the marketing team. A sales tool probably in most cases would sit within sales enablement, because a big part of the expertise that sales enablement brings to the table is that understanding of the sales persona and what it is that they need to be successful. And that doesn’t mean that a sales enablement team wouldn’t be tapping into subject matter experts or other expertise or talent that exists within marketing. Because it is specifically for the sales persona, the sales enablement team has a big role to play there.

I think the one other thing that we forget sometimes is that it is a two-way relationship, so no matter who you are working with across the organization, whether it’s part of marketing or HR, you want to make sure that not only are you receiving inputs from them, but you are giving feedback to them so that you make sure that there is that two-way communication in place and that everyone is benefitting from the relationship.

The one last group that I will mention in terms of boundaries would be first-line sales managers, and they have a very, very important role to play in enablement. Most enablement teams work at a headquarters or large group kind of level, and so that ability on a day-to-day basis to coach a rep a lot of times will come down to that first-line manager. So, how do you work together to make sure that you’re complementing each other? That’s something you need to spend some time working out, everybody needs to agree to, but making sure that there are good boundaries in place there and that you guys are complementing each other will only help the sales team to be more successful.

SS: I’m glad that you mentioned the frontline sales managers. You have written in the past that the relationship between sales and sales enablement really needs to be a partnership, and I think you’re absolutely right. I think frontline sales managers are probably one of the first stops a sales enablement professional should make in building a very strong partnership with sales. What are some strategies that you’ve seen sales enablement practitioners use to build out that partnership?

SL: You know, it’s funny. I don’t even think of sales leadership and sales enablement as being part of separate teams. They really are part of the same team. I think it’s very important that sales enablement leaders have a seat at the table from a sales leadership standpoint and be present and have input while key decisions are made for the business. That is certainly a big part of it.

There is also a mindset that an enablement team needs to have. Ideally you’ve got folks on your team, and it may not be everyone, but certainly, those that work most closely with field leadership, having some experience in their past carrying a quota, having worked in the field, having sales in their background really, really helps out a great deal. I think about some folks that have worked for me in the past and they could have stayed in sales careers, but they just truly love that experience of “how do we operationalize this on a grander level” and being part of something like that. So, they end up being drawn into sales enablement, but they very much have the same kind of thought process and motivation and way of existing and solving problems as folks that carry a quota out in the field. I think that kind of like-mindedness plays a big role.

And then it’s really about helping them be more effective at their jobs and making their jobs easier in a lot of ways. So, we take the skills that they already have, invest in them and make them better at what they do. Most sales leaders are great and receptive to that kind of coaching because that’s how they got where they are today. They worked with other individuals and learned how to fine-tune their craft, and sales truly is a profession and there’s a lot of craft involved in being really good at it. So, if you can approach it with that mindset and really be oriented toward setting them up to be successful, I think you’re most of the way there. And then it’s about good old-fashioned process, content, reinforcement, and metrics, of course.

SS: Absolutely, you must prove the value. Now, you alluded to this a little bit, but I want to highlight it because I think it’s important. You mentioned the importance of a sales enablement practitioner having potentially had past experience carrying quota and you’ve also mentioned sales empathy in the past. Why, from your perspective, is it important for sales enablement practitioners to have sales empathy?

SL: Sure. I think we’ve all been in a place where sales is seen almost as a necessary evil. I have to say I see that less and less and perhaps I’m just so embedded now within sales organizations that it is less common, but it’s a tough job. And I think that if you are not doing it, you don’t really realize what it is like to have that career in sales. The job doesn’t happen to you, you have to keep making it happen. No matter how awesome you were last quarter, you have to start all over again and make it happen this quarter. And very few jobs out there in the world are like this.

We all know if you’re a great salesperson, you are rewarded well for it, and that’s why. I think if you were to ask ten people in a room if they wanted to take on a sales job, you’d find maybe one out of ten that would really lean into something like that. I know when I’ve built teams in the past and hired people into sales enablement, one of the things that I think is critically important is to have real respect for sales as a profession and to approach everything that they do from that standpoint. I think it makes all the difference in the world.

SS: Absolutely. On that same note, what else do you look for when you are hiring people into enablement roles, both from within the organization and externally?

SL: This can be a tough one and if I were to point to maybe one thing that is holding back development of sales enablement and companies really being able to invest heavily in this area is that there is not yet – although I think that there will be – deep bench strength of individuals out there with true, modern sales enablement experience. So many times, when you are looking to fill roles, you have to broaden your horizons. It’s just not as simple as posting, “we’re looking for someone with three to five years of sales enablement experience in this particular space.” You’re not filling a sales enablement role the same way that you would a sales ops role, for example.

A couple of things that I think are really important, and I think a lot of these are soft-skill oriented. So, I look for people who are charming, and I know that sounds like an odd word. But certainly because of the cross-functional nature of the work, that ability to work with all types of people, to work across teams and do it in a very effective way, having a warmth and a charm and a graciousness comes in handy for a lot of these folks that are going to be in front of a room at some point, commanding that room, facilitating the conversation, giving a presentation. That presence is very important.

The demands on sales enablement are significant, and you are driven sometimes to deadlines that are not flexible in any way, so an ability to get things done and get them done excellently according to a deadline, I think, is really, really important. The one other thing that I look for, I look for work ethic, because I don’t think that you can train on. I also like to hire folks who have some background, even if they’re very early in their career, of achievement against a goal. It doesn’t necessarily have to be a sales goal. It could be something else. It could be something in sports or something that they did through their academic career, but just looking for someone with that kind of orientation. They are sort of naturally more inclined to understand what sales enablement needs to bring to the table.

SS: And so given that there’s not a strong, solid bench of sales enablement practitioners with what you refer to as modern experience, which I would love to circle back on in just a minute, how then do you go about ensuring that the sales enablement professionals that you bring into the organization themselves get trained and ramped and have a place to come share best practices with regard to sales enablement?

SL: You know, that is such a great question and I think it’s very much a “cobbler’s children” kind of story. I am trying to think back for the last few teams that I have built-in sales enablement if we truly were able to invest a lot in their personal development and I think the answer is probably no. We do, from a sales enablement standpoint, rehearse a lot and we do prepare, and perhaps that can bleed a little bit over into the personal development side of things.

If you’re preparing to present in front of a large team at a kickoff event or you are putting together a training program within a bootcamp structure, or perhaps a roadshow kind of environment, you’re not going to go out and do that for the first time without having significant preparation, feedback from your coworkers, without checking and crosschecking that it’s excellent.

And then I think through that, there is a development component for sales enablement. You know, the other thing that I would point to if you’re working with outside vendors, a lot of the time there is certification or “train the trainer” opportunities that come along and I’ve had folks on my team really take advantage of those and really be able to bring knowledge, skill-sets, and IP into their organizations and then take that along with them as they progress in their career.

SS: So, from your perspective, how should the success of sales enablement be measured? What are some of the core KPIs that you think sales enablement should be held accountable for within an organization?

SL: You know, I think the simplest answer to that is bookings and revenue. It is just as simple as that. Is the company achieving against its goals or not, are they meeting or exceeding quota? Now you want to break down a little more than that, of course. Looking at ramp I do think is important and what I like to see there are what I refer to as leading indicators, which tie to pipeline. Can this new salesperson that you brought on board, after being through all of the training that they received as a new salesperson at your company, create pipeline? Can they advance pipeline? How long does it take to get them to their first deal? Those are all metrics that you want to track.

Ideally, you want to see that normalized over a series of hires so that you’ve got a sense that if we bring 10 new salespeople into the organization, we know that they’re going to perform at “x” level. And that’s really powerful for an organization. It’s an investment for a company to hire salespeople, SEs, channel folks, and SDRs and all of the different large group teams that you will bring into a tech organization, which is what most of my experience has been around. You want to have some predictability around their success. You want to know that the training that you’re giving them, and the people that you’re bringing into the company, are set up to be successful.

That’s only one piece of it. That’s the onboarding piece. Where I hope that we’ll get to, and I think that we’re not quite there yet as an enablement function, is I would love to see us move into what I almost refer to as personalized enablement. So, you think about what people talk about with personalized medicine. If we were able to, through a series of metrics, really kind of tap into where an individual sales rep or even a first-line manager is at a particular point in their career and marry that to the right enablement, kind of think of it as a just-in-time type of enablement for what they’re specifically needing to learn, and serve that up to them in a way that kind of moves them along that learning curve and see it have an impact. I think that’s potentially a very exciting place for enablement in the future. We’re not quite there yet, but I think it’s coming.

SS: I think you’re right. I would love to hear from you, where do you think the gaps exist between getting us from where we are today to that nirvana state?

SL: Well, I don’t know if we’ll ever get completely to nirvana, but I think we can certainly get closer. Data is one of the pieces that we struggle with and I think all companies struggle with getting complete actionable data. If I’ve learned anything over the last couple of years, it’s that a) it’s hard to get clean, good data but also for a company to be able to tell the story from the data that they have and figure out the action around that. That’s also an area that’s a challenge. I think that AI will help us with that.

Then when you look at how enablement teams are staffed today, most of them are woefully understaffed. You know, they can do sort of the headquarters-level things, maybe the larger events like a kickoff or a roadshow. They can do the onboarding piece and maybe build out a little bit of content, but when you start looking at something like personalized enablement, that takes a greater degree of attention, or a different kind of approach, more of a bottoms approach, if you will, to making sure that you’re looking at these folks as individuals as opposed to just sort of large groups of people that need to go through a set of training.

So, one of the areas is just making that investment and understanding that your organization needs that and that it will have value. But you really just need to test it. You know, salespeople and sales leaders make decisions quickly and so I think if we can get to a place where we prove it through a pilot type of format, you will see it grow from there.

SS: Absolutely. I have to admit this is a little bit of a tangent question, but related. You referenced being understaffed or under-resourced. We get that question a lot. What is, in your perspective, the appropriate ratio for staffing a sales enablement team?

SL: So, I think a ratio model, unfortunately, doesn’t fit enablement. I wish that it did because it would make it so much easier. I look at it more as a relationship model, so you have to have certain functions covered. Look at the roles that you have that have more than 10 people in them in your organization, so you have to have the staffing to cover those personas. You have to have coverage for sales, for technical teams, for partners, for first-line managers, for sales development reps. Those tend to be the fairly large groups within the organization and depending on the number of people in those roles and the depth of the enablement needed, you may need more than one person.

So, for example, technical enablement tends to be very detailed so it’s quite common to have multiple people that need to support that persona. And then you need some back office or operational staff. You have technology and systems, communications, logistics are all a big part of enablement, so you need a team to work on that. Oftentimes as you get bigger, you need a content person or two or three, possibly a designer, to make sure that material that you’re putting together is packaged well and that right there for a headquarters team. And if you get to that bottoms-up model that I was describing a little bit earlier, then I think what you need to do is put enablement folks in place to partner with the leaders you have in the field. So, if you have, say for a larger company, an east coast, a central, and a west coast leader, they probably need an enablement person that aligns to them. Same thing with your head of EMEA, your head of APAC – you kind of see where I’m going with this.

SS: Absolutely, I think that is very helpful for a lot of the folks that are just getting started in their teams and trying to understand the structure.

SL: Or they’re a team of one or two and they’re out there trying to do it all, which is tough.

SS: What would you say is the best way for a lean sales enablement team to really get executive support and buy-in to support their initiatives, not necessarily only from a staffing standpoint but often even from a budget standpoint?

SL: You know if I think back to sort of the early days when I was first starting out in enablement, I had a lot of passion around this. I was working for a fairly large company and in that situation, it was, “look I see a hole or an opportunity that exists within how we are going to work it around this particular product. Here’s an idea I have for solving it. Would you sponsor me in running a pilot?” And I was able to get a yes on what I think was a $20,000 project at that time. We ran the pilot, we had great success with it. It birthed probably 10 other projects just like that and opened up the door for more enablement. If I’m not mistaken, that particular company is still doing these deliverables today, so it has lived on for a long period of time after that. But it is really kind of just getting that first enablement deliverable out the door and then a slightly bigger enablement deliverable. Then, it tends to break free from there.

SS: Thanks so much for joining us, Sharon, we really appreciate you taking the time to talk to Sales Enablement PRO.

SL: Awesome. Thank you, Shawnna.

SS: Thanks for listening! For more insights, tips and expertise from sales enablement leaders, visit salesenablement.pro. If there is something you would like to share or a topic you want to know more about, let us know. We would love to hear from you.

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