Enablement Is What You Make It – Sales Enablement Soirée, Summer 2020

SS: Welcome to the Sales Enablement Soirée session entitled Enablement Is What You Make It. By building your sales enablement function to be agile and be able to adapt rapidly in any given situation ensures that enablement is able to pivot as needed. Which we’ve seen be extremely successful during these recent trying times today, I’m excited to have Andrew Quinn, the vice president of sales, productivity, and enablement at HubSpot join us to talk about how HubSpot started to build sales enablement from the ground up as a cultural discipline within the organization. Andrew, with that, I’d love to hand it off to you.

AQ: Hi everyone, my name is Andrew Quinn. I am vice president of sales, productivity, and enablement at HubSpot. I’ve been involved in sales, sales management, sales training, and sales enablement for the better part of 25 years. At HubSpot, I joined at the early stage of that organization in 2009/ And I’ve been there for 11 years taking it all the way up through, you know, our $10 billion market cap we’re sitting on right now. And what I’d like to do today is really share with you how we run sales enablement, HubSpot.

I’m going to talk a lot about how enablement really is what you make it. We’ve made some very specific and deliberate choices on how we run enablement and HubSpot and like take time to introduce you to all of that. So, we have four keys to successful enablement that have really been effective for us, in the way in which we’ve driven our sales organization at HubSpot.

First one is how you define ‘enablement’ matters a lot. Key number two enablement is a business discipline and not a department. Key three effective enablement requires excellent communications. And key four enablement should be purposeful. Over the next 30 minutes, I’m going to walk through these four keys and really help you understand the approach that we’ve taken in how we’ve executed sales enablement at HubSpot.

So how you define enablement. It matters a lot. And I’m going to set up a little bit of a story here. So, I’d like you to imagine if you will, a drop of water. A drop of water on its own, fairly benign, put enough of it together and you can have a nice glass of water, which is certainly refreshing. Put even more of it together and all of a sudden you have a lot of power. And that power can be quite devastating depending on how equipped you are to handle it.

So, I’d like you now to picture of that drop of water and think of it as that critical new thing that someone wants to enable your sellers to do. So, when you think about a company, there’s a lot of different people in that organization that would like sellers to do certain things. Could be the product organization, could be the marketing organization, could be IT, legal, finance, they’re all looking for things for the sellers to do in a certain way.

The thing you have to remember is that there are a lot of drops all coming together, because there are a lot of different people in your company that are all trying to enable that salesperson to do something. I want you to think about this from the salesperson’s perspective. So, we have a salesperson here and she’s staring at all of the things that are coming at her from all these different groups that are trying to quote unquote, ‘enable’ her to do her job more effectively for the company. This is what it looks like for a salesperson. They are literally standing on the shore, looking at a 15-foot swell and they are about to get swamped by that. So, what’s the typical reaction is salesperson has? Well, they just pretty much run out of the way because they’re looking at it going, “I got to hit my quota this month. I can’t deal with that thing that’s coming at me.”

And when I think about it HubSpot, these are all the different kinds of things that are constantly flowing at our salespeople. There are all kinds of different organizations that have an effect on what this person has to do day in, day out. It could be something sales leadership has. It could be a new sales presentation update they have. It could be some new capacity management process they need to follow. There are all kinds of things going on.

The key objective or enablement at HubSpot is to knock this wave down. How do we create a nice, wonderful environment in which the reps can just swim out into all the things that they need to deal with and sequence it in a way that it’s just flowing in, in just a nice low tide, they can just go out and enjoy themselves and get things done.

So that’s how we’ve really thought about enablement. A lot of organizations may think about enablement as sales training. We really think about enablement as how do we deal with all of these different things that are trying to affect the organization and how do we smooth out that sequence, all of that, and remove as much friction as possible from the sales rep’s day.

And that leads us to the mission for the sales productivity and enablement team at HubSpot. And this is our mission. Our mission is to improve sales’ ability to generate as much revenue as quickly as possible, by continuously removing friction in real-time as our company, products, and sales team continues to scale and grow. We do this through tools, content, education, processes, and programming for effective change management that lead to a happier, more productive and efficient sales team.

So, if you look at that mission, one of the things that’s really missing here is sales training. At HubSpot sales training is actually part of our L&D organization. The sales enablement team works with the sales training organization, but our whole objective is to drive behavior change, knowledge acquisition, and essentially friction reduction relative to how sales reps do their jobs. How can we give them more time in each day to focus on selling activities versus all the other things that may come their way?

So that really leads us to four key guiding objectives that we have in the sales productivity and enablement team to drive what we do. When we focus on these four key things, enabling a repeatable HubSpot sales process, transforming our HubSpot sales team into Master Storytellers, enabling friction-free access to resources and information, and creating a universal path to mastery. So, this is our charter with the organization is that mission and these four-guiding objective. So, we’re really shape our enablement practice inside the business and they really allow us to have a very specific set of guardrails in how we operate with the rest of the company; to ensure that all those things they want the sales organization to do, we’re able to account for those, incorporate those into the way a salesperson operates, incorporate that in with sales leadership operates so we can move in a smooth, clear, and concise way forward in our operation.

So, with that, I want to talk about the second key enablement is a business discipline and not a department. One of the things seeing happen in organizations is a team gets labeled as the sales enablement team and then all of a sudden, they’re carrying the weight of the world on their back to do all these enablement functions.

That is a recipe for failure in my opinion. Enablement really is a team sport. It is a business discipline where all the different organizations in the business all work together and they work together to create seamless mechanisms in which the sales team can go deliver what they need to deliver in the marketplace. Selling is hard enough without the rest of the company getting in the sales team’s way. And one of the functions of the sales enablement team is to coordinate and sequence all of these different efforts to try and help the sales organization be more effective.

One of the things that I’ve seen really go wrong in organizations is where all the different teams in the company are pushing things to the sales team. We talked about that wave. The sales organization tends to just ignore those things or pick and choose the things they want to focus on. And therefore, you don’t have a coordinated, focused effort to drive your sales organization forward.

We’ve found that by positioning enablement as a business discipline, with the sales productivity enablement team being the organization that oversees all those efforts. We’ve had a much stronger operation on that front. So that leads us really to the way in which we interact with different organizations.

So, let’s say the legal team has some new things they need the sales organization to do relative to the way contracts are signed. Or the product team has rolled out a new product that they want sales organization to adopt and sell. We have arrangements with all these different groups where they understand what they bring to the party relative to enabling the sales organization. So, as collaborators, they’re bringing into this particular enablement initiative, the goal, the target of the outcome, relative, the thing they’re trying to achieve. They bring that content and expertise: department’s specific skills, the measurements and the metrics associated with how we’re going to measure achievement against this particular initiative.

And they assist in developing that project. We could never be effective if we have to be expert in all the different things that are happening in the business in order to enable the sales team. We need to actually leverage the expertise that exists around the organization, but take that and coordinate it, sequence it, package it in a way that makes it as easy as possible for the sales team to take that change on.

So, what do we bring to the table? Well, we bring that in depth understanding of the sales environment. We have a clear picture of what’s going on in sales organization. Which ways to communicate most effectively with the sales team so, they’re going to react to a particular change as positively as possible.

We understand the sales strategy and education flows that we need to implement in order to get them to drive down a knowledge acquisition path or a behavior change. We have the expert knowledge in the sales persona. We manage those projects, have the sales systems expertise and how to configure the CRM so that it reflects what needs to occur. We own a variety of communication channels that the sales organization trusts. And we have a project framework that we established with all of our collaborators across the company. So that project framework really encompasses a couple of things.

One is being very clear on what is that collaborators action? What do they do when they’re engaging with the SP+E team to execute an enable an initiative that they want the sales organization to adopt? And then we have a set of actions that are very clear on what we are going to do relative to fostering that behavior change in the sales organization. And we have this four-step process of designing the solution, creating the enabling project plan, delivering on the rollout, and then debriefing on the project with all the important stakeholders to make sure that we’ve executed in a way that’s expected.

So that at its core is some real key, I would say, fundamental framework elements of how we’re running sales enablement at HubSpot. And I want to take a quick aside on what’s in a name. As you’ve noticed, I’ve referred to our enablement organization as sales, productivity, and enablement, which shortens to SP+E. This is a really deliberate step that we took, because one of the things that I noticed when I took over the sales enabling organization at HubSpot about two and a half years ago, is that the word enablement was problematic.

Everybody wants to enable the sales team. It is the most popular word right now, relative to helping the sales organization be more effective. We want to enable them to do that, enable them to do this other thing. The problem with that is when it comes time to do certain elements of enablement that are, let’s say less popular, the sales enablement team gets dragged into those things. And the finger gets pointed at them. Oh, well, sales enablement will do that part.

And it gets really cloudy who owns something. Because when we’re talking about enablement, enabling something, does sales enablement own that? Does the organization that’s trying to enable the sales team on that? What does that partnership look like? So, we made a deliberate decision to call this team the sales, productivity, and enablement team, which then shortens to SP+E.

So now what happens is, everybody around the company says we need to enable the sales team to do X, Y, and Z. Let’s work with the SP+E team to figure out how we’re going to enable the team. That’s simple language structure put us in a very different dynamic relative to how we set up that collaboration relationship.

Everybody becomes very clear on what SP+E does versus what’s involved in the discipline of enablement. It’s such a simple thing, but it’s made a huge difference inside our organization, driving clarity on what we need relative to enabling the sales organization versus the team that is going to be charged with driving those enablement initiatives forward inside the organization.

That leads me to my next point and key number three. Effective enablement requires excellent communications. So, we have a variety of communication assets that we have invested in over the past two and a half years at HubSpot to really refine our enablement operation. Going back several years, our enablement operation is very fragmented. It’s one of the things that we wanted to address and make it a lot more efficient. And one of the things we realized, based on HubSpot culture, is we can’t just mandate every organization around the company that you must flow through the SP+E team in order to connect with the sales organization. Rather, what we did is we built a series of communication vehicles that are purpose built for the sales team.

When we did this in a way that we built trust with the sales organization, where they look at these communication vehicles as their source of truth. So, what ended up happening there is by building these vehicles over time, building the sense of trust the sales organization, building that sense of a source of truth, flowing through these different communication vehicles, when an organization decided they were just going to go directly to the sales team. The sales team would then look at that communication and ignore it. And they would quickly turn around and say, this really should have floated through the SP+E team. And then that organization would swing around and go, can you help us move this through?

And then we would build that relationship. it actually was quite a magical thing that is unfolded over the past couple of years, as we evolve these different sources of truth. To the point where now the entire organization knows that if they’re trying to drive a new product change, sales motion change, a new procedural change; they come to SP+E. They take advantage of the communication vehicles and move through. And we have a very deliberate communication sequence to make sure that the sales organization is very aware of what’s going to be coming down the pipe from enablement.

We run a series of monthly sales exec meetings, where I meet with senior leaders and I give them a very clear advanced notice on what enablement initiatives are sequenced to hit their teams, roughly six to eight, 12 weeks down the road. We run a series of a weekly manager meetings, where we bring all the sales managers on a weekly zoom call. Where we make sure they know what’s going to be hitting their sales team four to six weeks down. We will equip managers with comms that they can use specifically to their teams to communicate in sales management meetings. We have a series of monthly recap emails that we send senior leaders and sales managers. So, they know all the changes that are underway from an enablement standpoint. We run a series of assets on our Wiki, ATTN Sales pages, How to Sell pages, that are sources of truth for the changes that we drive. We have a sales digest, weekly newsletter, that has a video component and links to various documents and summaries that the sales team and the sales reps in particular used to stay on top of all the changes that are happening inside our organization.

So those communication flows are incredibly important, because we really are in the communications business. So, what you’re looking at now is our full communications flow. We also have an abridged version that we use for smaller rollouts. Because not everything is a huge major change initiative. Some things are a bit lighter in nature and they’re easier for the sales team to take on, to adopt. So, for those, we run the abridged communication sequence. The important thing is we have the full communication sequence. It makes it easy to run a shorter communication sequence when you need to. So, I really thinking through what is the full suite of communications we need to make. We can then run shorter communication sequences based on the degree of change that we did.

And that brings us to the fourth key, which is enablement really should be purposeful. And up to this point, there’s probably a pretty clear perspective as you’re listening to the talk that you’ve done some very deliberate, purposeful things inside HubSpot. And those purpose-built things really sit on top of a couple of key operational frameworks that I’d like to share now.

So, revisiting our mission, right? Our real goal here is to generate as much revenue through the sales team as quickly as possible, try to remove that friction. And we do that through the tools, content, education processes, in running our business. So, what does that actually mean? Well, we think about enablement like this. And the way the team is organized is essentially on this principle of getting point A to point B. Which in and of itself is very simple. But the way the team is organized, I have a group of individuals who are really focused on point B. And what we mean by that is, “What’s the desired state we need the reps to be in?” what do they need to know? What do they need to be able to do? What do they need to be able to say? How do the systems need to be configured, relative to this new desired state?

Let’s say we have a new product we’ve launched. There is a new sales motion that has happen. Well, what does that desired state look like? What are the value messages to be told? What are the different steps of revenue, to take home, to demonstrate that new product, or execute on that emotion? What types of changes have to happen in the CRM to support that move?

So, we really try to define what does that desire state look like and what are all the different assets that need to be developed to enable the reps to take on that change and operate in that new desired state. Then we have another facet of the team who’s focused on really point A; and getting from point A to point B. This team really looks at well, “Where is everybody now? How are they operating now? What is it going to take to get them from where they are now to where they need to be? And what is the project plan to move them from where they are now to where they need to be?” So that whole thing breaks down into our operating system.

So, our operating system follows this particular flow. So, on the far left, what you see P1, P2, P3, those are projects. So, we might have, let’s say three different enablement projects, and those enablement projects are going to flow through this five-step sequence. And step one in that sequence is scoping that project and assigning it to a project owner. This is always done by the enablement leaders on the SP+E team. They’ll take in any request and project up to this point. I’ll give you an example. For 2019, we’re halfway through the year we’ve done just over 300 enablement projects and driving those types of changes from the sales organization of all different sizes and types.

So, for every one of these projects, we scope out and assign that project. We assign it to a project owner and decision maker, who’s really the DRI or directly responsible individual for executing this project. Then we think about, well, what type of subject matter expertise or knowledge contribution are we going to need in order to execute on this project? Project one, we’ll bring those people in and we’ll start extracting all that knowledge and expertise from them. As we start to think about the assets that need to be created to drive this enablement forward. And then ultimately, we roll that out. Now we think about this five-step flow. (For lighter projects, it could be one individual who does every one of these five things.) I shouldn’t say every one of those four things, because the enablement team leaders are always making the decision on the scope of the assignment and then they assign it to an owner and that owner may actually possess the expertise necessary, have the ability to put hands on keyboards, create those assets, and roll it out.

In other cases, it could be like a project two, where there’s a project owner. There are five or 10 subject matter experts. There could be a variety of asset creators and several people involved in the roll out of that enablement. And we have these three chevrons: C, N, and D. And we’ll talk about those in a minute, which is a very key component of the asset creation execution. And how do we take that knowledge and turn it into assets.

But a couple of things I want to point out. One is in enablement team, everybody on the team has a specific set of role responsibility. Someone might be an instructional designer, or they are a project manager. Or they are a segment enablement support person where they’re focused on a particular segment in our business and they provide specific support to that segment. So, they have their role responsibilities, but then they also have team responsibilities. And what I mean by that is, anybody in the organization can be in service to the project owner based on their subject matter expertise, they’re ability to put hands on keyboards and create an asset or execute projects.

So, our team is very clear on what their role responsibilities are, but then also they can be drawn into a project relative to using their expertise as a team response. I’ll give you a great example. For me, I run the entire department and I have lots of leadership and management experience. We’ve recently developed a bunch of sales manager playbooks and in that project, the project owner is somebody who works for me, but she tapped me as a subject matter expert in writing some of these playbooks because I had deep experience in those things. So, I was in service to her, relative to using my expertise to create these playbooks. So, it’s a key component of our team, is people being able to be very clear on what their role responsibilities are versus their team responsibilities in executing an enablement project.

And then underlying this whole thing, we have a series of sequencing and operational rules that govern how this process runs. We have a series of work outputs and handoffs from each one of these steps into the next, and there is a variety of communication and feedback mechanisms that may flow. So, I want to move on to C, N, D for a second.

That stands for creating the concept, writing the narrative, design in the asset. So, this is our content creation sequence and it’s incredibly important relative to our ability to be effective for our customer, the sales team. So, this model really is a riff on how you make movies.

So the creating a concept. It really is the key themes and plot points in the story. If we’re running an enablement initiative, what are the key things we’re trying to accomplish? What are the key knowledge points we’re trying to get sales reps to adopt? What are the key behavior changes they need to make?

What are those plot points in the story and what are those high-level strategic things we’re trying to get them to do? The next step is then, we have to write the full and complete script. Communication at its core is a function of words and images. The images usually come better if we know what the words are first.

So, we spend a lot of time creating the script. What are all the words we need? What are all the descriptors? What are all the different types of communications that we need in written form in order to make this enablement initiative work? And then we take that stuff and move it into the delivery mode. Like what are the different containers we’re going to put this content into? How we are going to design those assets? Could be any learning course. Could be a train the trainer deck for sales managers. Could be a how to sell page. Could be a demo, like a pro video. Could be a one-pager. Could be a playbook inside our CRM.

There’s a variety of different packages that that script can go into. One of the things that we we’re doing, and I think this happens in a lot of companies, is you come up with the concept, and a bunch of high-level ideas, and then everybody just runs off and starts designing stuff. And what ends up happening is a lot of those assets can crash into each other or there’s duplication of effort. Or somebody who’s designing an asset really didn’t understand exactly how this needs to be communicated, because their expertise isn’t in that area and they design something that actually doesn’t quite hit the mark. We had this dysfunctional sequence for quite a while, and we’ve managed to correct it by adding in that step of writing the narrative. It really is the key to that highly functioning sequence.

And that brings together our full operating system of moving from project scope, to ownership, to subject matter expertise, to creation, to rollout. Using CND as our vehicle for driving asset creation relative to that enablement effort. And that ultimately leads to the next layer underneath, which is the enablement project implementation flow. When you think about one of those projects going through those five stages, how does the work actually execute relative to enabling the sales organization? And here’s the way we think about that.

We have the enablement project that gets defined. The DRI is assigned. All that stuff is set up. Subject matter experts are lined up and all those things are in place. But we have a flow that occurs, and, in that flow, the first step is trying to understand what type of sales manager enablement requirements we have. We’re not actually creating sales manager enablement at this point, but what role is the sales manager going to play in this enablement effort?

We want to define and understand that upfront. And then we hit pause, if you will, on the sales manager enablement. We know what the requirements are, but we haven’t built it yet, because the next step is we go and we then start all the seller enablement project planning and materials development. What do our sales reps need relative to this enablement effort? What are all the assets we’re going to create? The C, N, D; the concept, narrative, and design. All that’s happening here. But about three quarters to four fifths of the way through in that seller enablement work, we get to a point where we pause and then we look at and say, “Alright, let’s start developing the sales manager enablement materials based on the sales rep enablement materials that we built.”

One of the things that used to happen, which was quite ineffective in our organization, is we used to let sales reps and managers know about enablement at the same time. This happens in a lot of organizations that I’ve talk to. You know, typically the sales manager learns about at the same time, the rep does. The rep rolls up on the manager and says, “Hey, how do we do this new thing?” The sales manager goes, “I don’t know. I just learned about it at the same time you did.”

We’ve worked really hard to avoid that sequence. So, what that means is you need to make sure that the sales manager materials for enablement are developed off of the sales rep enablement materials. And the only way you can build sales manager materials is if you know what sales enablement is going to be.

So, there are times where we’re moving forward on a sales rep enablement project, and we will pause on the actual rollout of that as we build enabling materials for managers, and then we roll out those enablement materials to the managers. So, they know in advance what they need to do, why they need to do it, how they need to do it. And then we push play on the enablement, roll out.

When we put this particular flow in place, it made a remarkable difference in the degree to which we had flow in our enablement executions and the adoption rate by managers and reps. Because everybody understood what they were supposed to do, when they were supposed to do it, how they were supposed to do it, and more importantly, why they were doing.

And they got in the right sequence. So, managers were never surprised. Managers always knew in advance what they’d have to do relative to supporting their reps as their reps move down the road of some new behavior change or applying some new knowledge about how they operate. It’s been highly effective for us. So that ultimately leads to the overall way in which our team is organized and how it functions. Basically, this is a map of the SP+E team at HubSpot.

We get ourselves from the current state to desired state; moving from our project assignment through ownership, subject matter expertise and knowledge contribution and asset creation rollout. There’s a global enablement project manager who is assigned to that project to get us from A to B. The B team is the one that has figured out all the desired state stuff, our segment and leadership enablement project execution drafts off of a lot of that material that gets created.

It gets communicated managers; so, they’re never surprised. All that rides on top of our communication channels, which we talked about earlier, as well as our Sales Academy, which is our internal LMS. And then all of that sits on top of our selling strategy systems and productivity tools, that are the underlying bedrock of the way in which our organization operates.

Now, there are some recurring responsibilities that our team has, as one is managing all those different communication channels and recurring responsibilities, we have in operating the SP+E team. But at the same time, we see opportunistic initiatives to remove friction from the sales organization. So, whether it be developing sales enablement tools in house, retool in our operating system, developing different service offerings and things along those lines; we will take advantage of those opportunities as an enablement team to help our sales organization be more effective. And then we also run leadership development operations following the same enablement motion, but it’s specifically targeting that sales managers and senior leaders.

So, all of this stuff, it’s wonderful and great; but if you can’t measure it, then how do you know it’s actually working then? So, we have a variety of measures that we can look at it. We choose, as enablement, to look at the following seven things. On the front end, we look at deal creation rates, win rates, average sales price, sales cycle length or velocity, as our early indicators of behavior change and adoption relative to the initiatives that we have. Let’s say we roll out a new product sku, we’ll start to look for deal creation rates. Are they rising? Win rates. Are they rising? Is our overall ASP rising as a result of that particular initiative? Has it done anything to reduce cycle time?

And then we’ll also look down the road at rep productivity. Is rep productivity rising? Is rep ramp time shortening? What’s the overall happiness level of the sales organization relative to the jobs they are doing? So, in look at these seven measures, we get a really good sense of the impact that we’re having. Because one of the things that’s challenging in sales enablement, it’s very hard to measure the direct impact of a lot of these initiatives. At best, you’re going to correlate results to the initiatives. It would be very hard to say this particular thing yielded that particular output because there’s so many variables that sales out. But by looking at these seven things, we’ve been able to be quite clear on the impact we are having.

So, with that, it really brings us again to those four keys to successful enablement. Again, how you define enablement. It matters a lot and talk a lot about that. Enabling is a business discipline and not a department. It’s really critical that your organization understands the role that they all play in enabling the sales organization. All of those different departments, and how they coordinate to help sales do their jobs. It requires excellent communication in order to do this effectively. And it really does need to be purpose built for your operation. We’ve built this very specifically, based on the dynamics and parameters inside HubSpot. You may choose to build it in a different way, as long as you’re deliberate about it, you can be successful.

Really appreciate your time. Really appreciate the opportunity to share our approach to sales enablement. Hope you found this valuable, and I look forward to answering any questions again. Thanks.

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