Episode 77: Sales Enablement – Cory Bray and Hilmon Sorey

Predictable Prospecting
Episode 77: Sales Enablement - Cory Bray and Hilmon Sorey
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There are a lot of definitions of sales enablement. What is it? How do we do it? Why does it matter? Having a process and mindset that extends across an entire organization can help enable salespeople to be successful. Still, it would help to have a clear plan and goal to get the most impact out of the enablement process.

Today, I have two guests Cory Bray and Hilmon Sorey.  Cory and Hilmon just happen to know a little bit about sales enablement. They are the authors of The Sales Enablement Playbook and they run ClozeLoop a sales enablement platform. They are based in San Francisco, and this is a fun and lively episode with two guests diving into the topic of sales enablement.

Episode Highlights:

  • Cory and Hilmon share their definition of sales enablement and focusing on the prospect.
  • How there isn’t a one thing silver bullet type solution to sales enablement.
  • Every department needs to contribute to sales enablement.
  • Having a mindset based on customer engagement where every team contributes.
  • Having the customer conversation at the center of the bullseye. Then as the concentric circles move out there are other team members contributing.
  • Understanding your messaging and how it relates to buyer personas.  
  • Pain points and features and how they relate to customer stories.
  • Issues with a disconnect between marketing and sales. Creating micro content for the salespeople.
  • The three types of sales conversations: lone wolf, scripting, or finding the sweet spot of the entire team’s effort.
  • Creating a playbook that allows a natural feedback loop.
  • Knowledge management is about the conversations.


Episode transcript:

Marylou: Hey, it’s Marylou Tyler. This week, we have a really interesting, I think Hilmon is the one who found me, but we have two authors, Cory Bray and Hilmon Sorey of a book called The Sales Enablement Playbook. I think when Hilmon connected to me, and I saw the title of his book, I knew that we needed to speak today. I don’t know about you guys, but I definitely have heard a plethora of definitions of what sales enablement playbook is. Cory and Hilmon wrote this book, they’re also the co-founders of ClozeLoop which is a sales enablement platform. They’re out at San Francisco. Welcome to the podcast!

Hilmon: Thanks for having us, Marylou.

Cory: Thanks a lot. We’re excited to be here.

Marylou: I just love having two people to talk to. This is really cool. I don’t know why this feels so new and fresh, but it does.

Hilmon: We’ll see if you still like it at the end.

Marylou: Indeed, indeed. Okay, tell us, in your words, what is the definition of sales enablement. What is it?

Cory: We believe that sales enablement is the concept of extending a prospect centric mindset to all departments within an organization. We spend a lot of time thinking about this and there are tons of definitions running around. It’s aligning sales and marketing, or its content, or its training, or on-boarding and all these different things but every definition that we’ve heard is either too narrow or too shallow. We started thinking about it and realized that most companies out there stated they’re customer centric. When you think about sales enablement, it’s taking that existing mindset and tweaking it a little bit to focus on the prospect.

Marylou: Okay. Does this align at all with persona development and the word ‘persona’ or are you using prospect in a different way?

Cory: We look at personas as a subset of prospect. For any organization, they might be selling three to five different personas and you can use the strategies and tactics that we outline in the playbook to be able to engage those folks at the top the funnel, for sure. That’s a component of what we’re talking about.

Hilmon: This is Hilmon, if I could chime in a little bit. A lot of what we heard in working with our customers and clients, I’ve been a management consultant for 10 years here in the Bay Area working with a lot of Silicon Valley firms and having conversation with CEOs who are trying to figure how do we dupe the bottom line, how do we enable our sales reps to have more efficacy in the marketplace which is full of a whole bunch of noise.

What we kept hearing was I’ve got a sales enablement manager, or hey I bought this sales enablement tool, or I’ve implemented an SDR Playbook. All of these things, people in the executive management were believing that each one of these little things could potentially be the silver bullet to increasing the efficacy of the sales team. When we really stop to think about it, we came to realize that where they were failing was in thinking that there was a point solution to sales enablement, that there was one little thing that they could purchase. Because the marketing is really good, Marylou. You see the same stuff that we do, right?

You buy into that and then you don’t realize that this is something that needs to be an ecosystem inside of an organization, that every department needs to be focused on how they can contribute to enabling sales to be more effective. Whether that’s the knowledge management loop in allowing products to tell sales that this is what we’re doing and why we’re doing it, persona development which ties into marketing, HR which is working on professional development and training tools, all of these things come together to “enable” a sales team to be more effective.

We do this with the mindset of looking towards how do we go about engaging with our potential customer and how does each department contribute to our ability to engage with a potential customer in a market place. That’s what we mean by a prospect subject mindset.

Marylou: Okay. I’m a visual person, I’m trying to visualize. I see the prospect in the center of a bull’s eye or the center of the ecosystem. And then shooting out from that, are you saying that all the departments who touch the prospect are contributing their know how, their expertise, their rhythms, their processes, their methods with the sole result of trying to enable the sales executives to have better conversations, to reduce the lag in the pipeline, and also be trained so that they have those conversations which are more meaningful in nature and they’re able to gently guide their prospects through the pipeline. Are all these things part of sales enablement?

Hilmon: You nailed it. I’m a visual person too, so I saw the bull’s eye. At the center of that bull’s eye is a conversation with a prospect, not even a sale. Let’s just say the conversation with the prospect and this is the sales person. Whether it’s an SDR or an AE, whatever it might be inside of your organization. The bull’s eye is that individual moving their mouth to have a conversation with the prospect.

Then if you look at the concentric circles that move out, you potentially got their manager. How is their manager enabling them to be more effective? Through training, through coaching, they’re providing tools. Then outside of that, maybe you do have someone in the organization that’s called the sales enablement professional that’s developing scripts or that’s developing tools or is managing your admin on your CRM or is providing you with some kind of marketing automation or email automation.

Outside of that, maybe there’s a greater scope that correlates to someone who is called VP of people or HR, something like that, who’s providing you with some level of training. Then outside of that, maybe you’ve got the accounting team which works to price the solution in such a way that they can appeal to the specific vertical or a persona. Or maybe even broader than that, you’ve got legal which is exploiting documents to make sure that the stuff is closing. But all of that entire bull’s eye is your organization and those concentric circles become more and more intimate. The closer you get to the customer conversation, but each department in the organization has some contribution that is making to helping a sales team to engage in. It may not be direct to your point Marylou, it may not be that, hey, from products, I’m getting this specific competitive intelligent language and I’m going to go regurgitate that when I have a conversation.

It could be more nuanced, and it could just be performing your function in such a way that you keep in mind that, gosh, this salesperson is trying to close a deal in the middle of August. Here I am at legal and if I foresaw this thing then that means it’s going have a detrimental impact on this person’s ability to close a deal this quarter. Having that kind of consciousness around sales is what we’re talking about. Again, it becomes more micro depending upon the department and its intimacy with the actual sales conversation. But you hit it on the head, I like the bull’s eye. We will put that on the cover next time.

Marylou: I like the bull’s eye for so many things. I think I overuse it but it’s very simplistic for me. It gives a couple of things, one is the focus is in the center and as you move out, depending on what you’re using it for, you’re going to either leverage existing technology, you’re going to leverage people, whatever it is, it’s not you personally who’s going to do the thing. It may be a manual to automated kind of thing. I do like the bull’s eye for that purpose. It does give that sense of as you move in, things are more concentrated, and then as you move out, you’re going to be leveraging and utilizing connections or people or technologies, or processes or whatever it is in order to be able to still have the same result but not humanizing it as much.

Hilmon: You know why else I like it? The other reason I like it is because it’s taking an external element and focusing really specific. You’re taking the arrow, that’s why the bull’s eye exists. Perhaps have a focal point. I like it, you got us from there.

Marylou: Like I said, I totally overuse it in my world, but it does have a lot of applications for what I’m doing. The people who listen to this podcast are typically business developers, people responsible for revenue generation, but also responsible for keeping the pipeline full of qualified opportunities and reducing that peek in value effect. In your book, I want to do sales enablement, I’m focusing on top of funnel, what are the three or so main points in the book that people will be able to start acting on as soon as they read your book? From a top of funnel perspective.

Cory: Yeah, totally. I think probably the first place to start is messaging and understanding not just what your messaging is but how that messaging relates to specific prior personas, and then tying that to specific product features and then finally looping in customer stories.

There’s a matrix in the book, I forgot what the chart number is. It essentially says for each buyer persona, you should know what their pain points are, what features address their specific pain points and then be able to relate those to customer stories around how companies are actually using your product in that way. I think that’s one thing that really separates the great business developers sales development for folks from the ones that aren’t that successful. They really understand what does a day in the life of my customer look like and how does the product fit into that. I think that’s the one that I’m probably most excited about.

Marylou: A lot of people have done this but I just talked to somebody this weekend who still hasn’t figured out what’s my niche, what’s my market, who are my people. Taking it one step up is that you’ve got to also define who these people are. At top of funnel, you mentioned three to five people through the sales cycle, we may only meet three or two at top of funnel before we get to a qualified opportunity, and then more people come in as the sale gets closer to close. If you’re doing all roles, you’ll have to know everything from your book. If you’re doing just prospecting, then you’re going to want to be able to focus on those people with whom you’re going to bubble up interest, get that first meeting perhaps. You may, if you’re a business developer, do some qualification where you’re getting it to the point where you can pass the baton over to your sales executive who takes it the rest of the way.

But to your point, you definitely need to have the personas defined from a sales perspective, that’s another big thing for me is sales personas are not marketing personas, necessarily. You guys talk about that and then also this messaging you talked about is really important because each of these personas that we meet and greet at top of funnel will have a very different look and feel of maybe the same pain point but the way it affects them and the challenges that they have around that pain point may be different. As well as the language they use to describe the challenge or pain may be different.

Hilmon: You hit upon something that we talked about in the book which is the differentiation between marketing and sales from a content perspective and a delivery perspective. It’s great for marketing, I’m a former marketer, so hopefully I can say this. In marketing we like to get in there, we create these great white papers and case studies and we’ve got decks, we’ve got all this stuff that’s fantastic. Often, we don’t realize that the salesperson has three to five minutes. Within those three to five minutes, if they’re not saying the right thing that uncovers the pain that that persona or role or individual you’re talking to is actually dealing with on a regular basis, you’re not going to get to that next meeting.

I don’t know if you’ve experienced this before but I think at the top of the funnel, there’s often a disconnect between marketing and sales where marketing will say, “Hey, I created all this great content, you’re not using it.” Sales will say, “You created a whole bunch of stuff that I can’t use.” This was another [00:13:19] around how do we distill that good stuff that marketing got in [00:13:23] format and make it micro content but the salesperson can actually articulate. Again, going back to this bull’s eye, in conversation, whether that conversation be email or in person or via phone, to their target prospect.

Marylou: Right. The way that we describe it in my world is marketing really is one to many. They are trying to get as many people as possible to bubble up to the top and like I kid with my dogs, if I open my eyelash in the morning, they are on the bed licking my face, it’s time to move. Just like my new activity that happens in marketing, that’s a win for marketing. For us, it’s belly to belly, it’s one to one conversation for salespeople. We have to flip the content that we get from marketing on its side, pull all those relevant pain points that are in that one piece and chunk it down into one pain point per conversation until we hit on which pain point is resonating the most.

We can use the marketing content, we love the marketing content but we really need to flip it sideways and take it and squirrel feed, as Aaron and I used to say in Predictable Revenue. Squirrel feed our prospects with one thing at a time to get their arms around. Wow, this is really more challenging and more difficult and scarier than I thought, as opposed to giving them, you could have this, that, these and those. You’re just giving them one pain point, you’re solving it and maybe you’re giving them a cliffhanger until the next pain point that they’re going to actually come against if they don’t make a decision.

Cory: Absolutely. I totally agree with that, Marylou. I think the challenge for companies is defining the we. Is the we that the individual seller as an independent person or is the we the organization. That’s really where we see the sales enablement ecosystem popping out, is that for each one of the specific conversations or specific pieces of messaging, it needs to exist but who’s going to create it? Do you want everybody doing it their own way from scratch? Do you want it being developed from a top down perspective or one person, you will do this and this is what you will say? Or do you want it to happen organically but in a way that other people can collaborate, work together and learn from what’s worked in the past? I think that’s a big challenge a lot of organizations face is that we need to have these front line people really contributing to the conversation but not starting over from scratch and doing everything their own way.

Marylou: The part about sales enablement that I think is most effective for the audience listening today is that there are three types of ways that you can have conversations. You can be a lone wolf where you’re doing your own conversations, you’re creating your own template, you’re doing your own emails, you’re doing your own scripts, you’re having your own rhythm and it’s working but the rest of the team is not taking advantage of that. Then you have this scripting approach where your management or somebody in the organization says, okay this is what we’re going to do, this is how it’s going to look, this is what you’re going to say.

But there’s a third option here, I think, which is what you guys say in the book which is really about finding that sweet spot of taking the entire team’s effort, managing that effort, taking the results of that effort, and then creating a rhythm, a cadence, a sequence that works based on the results that you’re getting from those conversations.

That is what I think sales enablement and the technology surrounding it and the methodology gives you that ability to do, is take and leverage the data pieces of tracking the conversations and allowing you to mold what those conversations are going to look like because you’re going to know from the results of previous conversations, what’s working, what’s not, how to order the pain points, what order works best for the persona with the goal in mind to reduce the lag in the pipeline and to maximize return on effort. Would you agree that your book is really focused from a sales enablement point of view to take the results of the many and create a process, a path that’s going to be more successful because you’re leveraging the data on this as well?

Cory: Yeah, absolutely. It’s all about that ecosystem that allows you to get the intelligence from all the really smart people that you hired in the organization, capture it, and then distribute it to the rest of your team. The interesting part is that’s what we wrote the book around, and it’s actually what our software product does as well.

Marylou: I know I’ve been taking more of your time. We’re ahead of our 20 minutes that I like to try to keep it to but this is such a great topic and I know there are a lot of questions that are out there. If I was getting started and I’m a manager, it doesn’t even matter the size of company but I know I’ve heard the word sales enablement because I’m listening to this podcast, I’m focusing on top of funnel, where should I begin? What would you recommend that I do when I stop listening here, what should I look at in my organization first and what kind of planning should I go through, very high level, in order to be able to start implementing a sales enablement strategy in my company?

Hilmon: I’m going to say that the first thing you’ve got to do is a buzz word right and I’m going to redefine it a little bit, but you’ve got to create a playbook for your team. By playbook, I mean something that includes your competitive differentiators and maybe identifying how you win, where does your competitors win, and where you babble and what those conversations look like. Any kind of success stories or customer evidence that you may have that the sales team could use to leverage the conversation. Being able to understand what objections you face and how you not overcome them but have conversations around those that help a prospect to evolve their thinking, kind of in a challenger sales methodology. Understanding personas, I may have said that already.

The idea though, there are lots of folks out there that create these playbooks, but here is the problem. I’m not a Game of Thrones fan but playbooks exist in dusty old libraries. Back in the day, when I was in college, we were talking about creating these business plans. The business plans have all of these SWOT analyses and executive and all these other things. They’re 50 pages long. You create this fake investment and then it sits on a shelf. It didn’t actually have any efficacy in the management of the organization, it was something that you did as an event and then it was done, you wiped your brow, you said great, now let’s go do what we’re actually going to do when we get on the floor.

When an organization needs to do now as sales manager, is begin to develop the playbook but develop it in such a way which allows for a natural feedback from your front line troop that allows your feedback loop from product or engineering, from marketing, and allows you as a manager to have dialogue and to archive the type of conversations that might be taking place in Slack right now, they might be taking place at the water cooler, but being able to harness these conversations in such a way that you can distribute them throughout the organization, the sales organization for a couple reasons. One is that there’s so much noise in the marketplace. Once one of your salespeople is keying in on something that works, everybody needs to be leveraging it.

Number two, in Silicon Valley, we’re out here dealing with these organizations that are trying to scale so quickly. They’re bringing out folks who are fresh out of college, have had notes, have had no sales experience from their background, how do you ramp these people quickly? It’s not by having them reinvent the wheel, it’s by having them learn a process that you cultivated and something that you’re working on in a continuous basis, that have a feedback loop that gets better and better and better.

Finally, there’s so much attrition. The average sales manager or executive leaves after 18 months. I’ve seen SDRs or folks around the top end to the funnel, business development reps or sales development reps, or inside sales people, those people can churn at 9-18 months. How do you continue to harness and maintain for the organization this piece of knowledge the things that some of those people who are great have uncovered in the process of doing their job inside of your organization?

If you put together the infrastructure around which you are just beginning to manage these types data inputs from a knowledge management perspective, you’ll watch that thing scale and grow exponentially by opening up the opportunity from everybody, from the sales floor down the executive suite, to be able to input into that knowledge base and everybody to get access to that and filter it. That’s the first piece. To make it [00:22:36], playbook, but not the playbook that you print out and leave on your desk, not the playbook that ends up at some kind of laminated thing that you stick your computer, but something that you’re leveraging inside of your work flow.

Marylou: So funny you bring that up about collecting dust. In my other life, I do market research reports and I remember walking into one of my client’s offices and she had 20 years of reports lined up on top of her desk. Truly, you could just see the dust settling on top of them all. I don’t know if she ever tried that.

Hilmon: That’s crazy!

Marylou: Yeah. But it’s something like ‘have to do.’ I’ve got to do employee loyalty survey every year.

Hilmon: You know what’s funny? We go into organizations all the time, Marylou. One of the first questions will be like when we begin this conversation on knowledge management, we’ll talk about the knowledge you’ve got. Have you got a playbook? One of three things happen. That’s exactly what you said, which basically walks over to the shelf and blows, the dust goes around the room and they grab something, or they start looking through Google Docs. They’re like, yeah, we had that one in here. It’s hilarious watching them as they search “play book” “playbook” “sales team strategy” and then they’ll find distant pieces of it with revisions they saw all over the place. You know the drill, you’ve had this experience before. That’s not doing it much good.

Marylou: I like the term you guys used of knowledge management because it’s really about the conversations and which conversations, with what personas, work the best, reduce the lag in the pipeline and allow us to get to close with a higher percentage. That’s what it’s all about. The old Predictable Revenue formula was really looking at the funnel itself, looking at the average deal size and then the lag time. Knowledge management is a big part of that and you’re right.

I am teaching an MBA class here in Des Moines and I’m the only instructor that’s teaching sales in an executive MBA class. People are coming out of college with really not a lot of idea about sales. I’m anomaly, I’m a novelty teaching a prospecting class. They just aren’t there, which I don’t understand why. It is what it is, so you’re right. having this type of playbook where they can come in and have whatever they need to be effective right away, just nuance seeing their conversation and getting self-esteem a little higher so that they know that they can have these conversations with the level of persona that they’re talking to and meet them where they’re at, but also be able to say, look, these are the most successful conversations that we’ve had for this persona in this order. How great would that be?

Cory: That’s it. It’s simple too. That’s the last piece, it’s just keeping everything very simple. The cool thing is that it can be complex but elegant. I think there’s a difference between complex and complicated. Some of the most advanced calculus formula are very short but it takes years to learn how to actually use them in practice. I think that you take people that have never done it before, sales enablement or developed all these things that we talked about during the show, the first result is going to be overly complicated. I think really focusing on simplicity is critical if this is going to be successful.

Marylou: The book is The Sales Enablement Playbook by Cory and Hilmon. They are out at San Francisco area, they have a company called ClozeLoop. How else can we get a hold of you guys, if we want to learn more?

Cory: We’re all over LinkedIn.

Hilmon: Not hard to find.

Marylou: It’s Cory Bray and Hilmon Sorey. Look them up on LinkedIn. Really, this has been a great conversation. Thank you both for being a part of the podcast today and I look forward to seeing how things move along with your company, moving into 2018. Thanks again.

Hilmon: Our pleasure. Thanks for having us, Marylou.

Cory: Thank you.