Why Enablement Should Be One Third of Your GTM Plan

This post is a transcript of a fireside chat between Databased's Dan Watkins and Fullcast.io's Tyler Simons. To view the video, please click here.

Tyler Simons 00:05

Hello, everybody. Welcome to another Fullcast fireside chat. I'm your host, Tyler Simons I'm the Head of Customer Success here at Fullcast. And we are a go-to-market planning and execution platform. So it's interesting. It's this time of year everybody's planning, right? We're like close to this territory but what I feel like sometimes gets forgotten about is the enablement needed for a go-to-market plan to be successful. And today, we're bringing Dan Watkins with Databased to help us unpack this. Dan, why don't you give us a rundown on what you've been up to lately?

Dan Watkins 00:45

Okay, sounds great. Thanks, Tyler. Yeah, so Dan Watkins, I was I started in the basement with Qualtrics, back in 2007, as employee number 15, lead sales globally for them until we got acquired by SAP at a blast doing that, then I've been helping startups ever since. And so I advise CEOs, and founders on how to run go-to market for their business and operations. And so I've been spending a lot of time with early-stage companies early a Series A, all the way to companies getting ready to go public is how they need to go re-architect their go-to-market strategy, and one of the most common things that I see people pay a lot of attention to quota, what number do we have to go hit that goes all the way to the board. They're paying attention often to pipeline generated and other activities. Sometimes they miss that. Almost always their enablement strategy is an afterthought. I can't tell you how many executive meetings I've been in talking about, hey, we're gonna do this, we're gonna hire this many people, we're gonna go do that. And they, they don't even think about how are we going to develop the people so that they actually succeed? And what is our enablement strategy? And so I was spending a lot of time with executives building out that strategy and CEOs to make sure that it's funded from the beginning.

01:54

So this is interesting. I think we're gonna get into the details here in terms of like, enablement, go to market planning, but why don't we level sat with everybody and talk about in your terms, what enablement is, like, when you talk about enablement? What do you see happening? What are the components of enablement, if you will?

02:18

It's a little different for each company. And enablement to me, if you just look at the definition of it, are you enabled? So as a CRO, you're gonna go and set a revenue target, you're gonna go and say, We have to get this many deals this, whatever it is, how do you go get there? And that's the technology stack that you have like, Okay, are you enabled that way? And are you trained, even use the technology that you have, whether it's your CRM, whether it's your performance management software, I forgot my intro, I'm actually the founder and chairman of the board for a company called database to that for performance management. But so anyway, so enabling the team with the right technology, enabling the team with the right content. And so that content can be just they can be marketing materials and pulling it together in an easy-to-digest form. But it's also training. And often it's called training and enablement. But you take all of the enablement strategies that you have, and then how are you developing your people to go get there? And so that's how I think of training and enablement is that they're combined together, they report into revenue operations. I know we're going to talk about that as we can as we kind of go throughout but that is the business unit responsible for enabling the vision of the CRO that's the enablement team.

03:28

Right. So why you mentioned this why, you know, enablement reporting into revenue operations or revenue operations is responsible for it. What are some of the things that you've seen? Well, I guess the first question is, really why should revenue operations be responsible for enablement? And to maybe what are some of the other examples of like scenarios where they haven't been reporting up to revenue operations, maybe straight to sales or to finance and some of the gotchas there?

04:00

Yes, there's one major caveat is I'm assuming revenue operations reports into sales. If revenue operations is reporting to marketing or reporting to other functions of the business are finance or something like that, then I wouldn't recommend that revenue operations run enablement, but assuming revenue operations is reporting to the CRO or vice president of sales, then my assumption is that director, CEO, or sorry, CEO, or whomever the head of revenue operations is, is the most aligned executive to the VP of sales, the go-to-market leader, let's get it done. And so the enablement team, if they have access to the top executive that knows the strategy so cold, that they can actually go and get it done. And whereas I've seen things get really kind of wonky as enablement starts to be called enablement or in reality, all it is is onboarding training. And then onboarding training all becomes HR training because enablement reports to HR. And so I've seen that be a major Miss. And it doesn't end that the sales team is constantly complaining about another training because it's HR oriented, or it's just the next security training, rather than being trained on things that actually get them really good at their jobs. So I've seen that not go well. I think you look at that as something.

05:24

Well, yeah, yeah. I'm just curious, like, let's say I'm a person listening to this. And that's exactly what's happening, let's say, enablement, reports into HR, or finance. How might I go about trying to change that culture, or starting to like, make enablement, what we think it should be, which is, you know, not just training and onboarding, but just the whole scope, right? The tech stack, the content, and the enablement and ongoing training of like, how do you sell the product, and so on and so forth? Like, where would somebody start in an organization to like, try and change that for the better?

06:09

Yeah, so I've had the unfortunate experience of having to unravel that in so many different groups, either that I've advised or even at my time at Qualtrics, where it gets so encumbered with HR practices, that it loses the identity of sales enablement, or of enablement in general. And so the first thing that I would go in and do is one, talk to your VP of sales, your CRO and ask them what their vision for enablement is. If they don't care, and they're fine, that it's onboarding and training, then you've got really two things you can go into one, talk to them about how it could be different, and see if they actually will care. Or if you're an enablement-minded leader that has a broader vision, maybe go look for a different company. Because if the VP of sales or the head of revenue, CRO doesn't actually care, enablement is not a core part of their strategy. And after talking to you as to what it could become, still doesn't really get excited about it. Go take your time and energy with somebody that does. Because if at the very top of revenue, if they don't care about enablement, even after you've explained what it can become, that the content will be purpose-driven, that it will actually be aligned with what the CRO wants to happen in the organization and your techniques are going to use that the tech stack, they're going to get rid of the garbage that just clutters people's calendars or clutters people's days with data entry that doesn't actually solve any problems, that the training is aligned with sales skills that matter. If they don't care about that, I'd suggest you go and you look somewhere else and go find an executive that does if they do, then ask them if they're willing to sponsor you, across the executive team in that reorganization. Or, if they're not willing to go and talk with HR about pulling training and enablement into revenue operations, then ask if you can create a basically duplicate organization, call them enablement people, not trainers, don't call them onboarding specialists, don't call them anything that's going to create red flags internally. And then you go and you start hiring enablement people that literally go and do everything other than what the HR team was doing.

08:13

That was exactly going to be my question, because I was like, what if you just created a kind of a like, same style organization within the organization that kind of just did that? And I think that would be a good approach if you're just hitting roadblocks there.

08:27

Yeah. And I would recommend from a staffing standpoint, that you can get as high as a one to 25 ratio. So for every 25 People in SDR land and account executive land field sales, customer success, anybody touching the client, one to 25 would be the best one to 50 would be about as light as you'd want to go from a staffing perspective. But why is that? Part of it is so that you can actually go in and work one on one. When enablement organizations have reported to me as the head of revenue. Every enablement person has enablement, targets with teams that they support. So imagine you have 25 people that you're supporting. And you're working, I don't know, it's a region of individuals selling roughly the same product to roughly the same type of buyer. But they each have different problems. Some of them are struggling at Pipeline generation, some are struggling at Discovery, some are struggling at closing deals, some are struggling at renewing and expanding whatever it might be you if you have it at one to 25 you have enough space to partner with the sales manager or the customer success leader and create individualized goals for the team at one to 50 or sorry for the individual at one to 50 You can do it at the team level. So you can say okay, sales manager or customer success manager, what is the number one sales skill that we're going to go work on? Is it converting at the discovery level? Is it pipeline generation? Is it closing? Is it stage progressions? What is it? And then okay, we're here today, by the end of the quarter, we're gonna get here and you align with that frontline leader. If you haven't one to 25, you can do it all the way down to the rep level. And you get real personal with the people you're helping and then they buy into enablement, too, because like, wait a second, I'm better empirically, after working with this team.

10:21

Yeah, that's super interesting. I think we're gonna come back to this goal piece, because I want to start to look at how we might be able to set goals so that, you know, we're going to take this one to 25 thing. And we might set some goals as it relates to the go-to-market plan and the rollout and kind of tie all this stuff together. But let's talk a little bit about how enablement can help you jumpstart the execution of a go-to-market plan. So we do all this planning. And maybe we take a step back, right, let's actually take a step back now and think about this. We all start talking, talking, let's say six months before year-end fiscal year-end, we're all thinking about the strategy, then then I'm going to walk us through a typical planning timeline. We did we're thinking about that we usually get a number from finance, then there's some capacity planning that's done to figure out you know, who, how many people do we need to hire to get to that? Where are we going to put them? Then there's typically some territory planning, Let's carve out all the world of accounts, some quota setting, where do you see enablement fitting into this timeline of events? Should they be involved at the very beginning, when a strategy is being formulated? Do they need to be involved in each of the stages to understand okay, well, this is what going to market is going to look like. And so I gotta develop. Maybe I need to roll out a tool or enable something within Tools. Maybe I need to put content together. Like, where should we have enablement plugged into this process so that we end up getting to a point when we flip the switch on our go-to-market plan, enablement is ready to go? And the reps are excited about what's about to happen.

12:08

So somebody who is aware of enablement, and what they do should be there from the beginning. But a lot of organizations, if they're just starting in enablement, they're not going to hire a director-level individual who is going to add value to those strategic meetings. And so it would be annoying for everybody else in the room. If it's like, okay, you've got the VP of sales, you have the VP of Marketing VP of Customer Success. And then you have somebody who's two years out of college who's responsible for enablement, that's in the room and all the meetings. So what you if it's in that case, where enablement is just starting, you have somebody really early in it, I would bring them in towards the end. But then that VP of sales or the director of Rev ops, or somebody who is strategic needs to be contemplating, okay, what is enablement going to be doing from the beginning? Why is it that we set our targets at this level, they need to be able to answer those questions to whoever's executing on the enablement side. And so if you have a senior leader for enablement, absolutely have them from the beginning. And when I ran my last role, where I had about 500 people at Qualtrics, I had my global head of enablement from the very beginning. And I mean that we had a ratio of I think we were one to 35 there for my organization. And because I want every part of the strategy him to be aware of, and then he was able to go and deploy that across all of his teams through every step that you talked about. But if you're starting over in a startup, and you have one person who does enablement for the 30 reps that you have, and that person's three years out of school, we probably have somebody else that's sharing with them the vision, and they don't need to be in necessarily all

13:45

the meetings. Yeah, it's like the head of Rev ops, or the head of sales is the person that's playing that head of enablement, strategy role that then communicates that to the person and we'll just kind of, you know, build and execute all that stuff. What? So let's say you have, I think, what would be interesting is to understand some of the questions or the perspective that ahead of enablement, let's say you do bring in a head of enablement at that first conversation. What are some of the things that that person should be thinking about at that exact like those strategy conversations, you know, when they wanted to go ahead and contribute to the conversation? Questions, they should be asking things that they should be thinking about,

14:39

I would say the emotional state of the reps and the sales managers that are now going to be impacted by these new targets. What do we do to make sure that they're still fired up and excited that they buy into what we're gonna go do so there's an emotional component to it? How does the tech stack need to change and what ad admins for that tech stack are they going to need to go work with so that this can get done? What content? Do they have a plethora of verses? Are they short on in order to go kind of nail the new messaging? Do they need to go partner with marketing? There's a lot of a personal APIs they need to be thinking about as they're in it then okay, now sales skills wise, if we're really going to go and increase quotas, we're gonna hire fewer people, because we assume our win rate is going to be higher. Where in the sales funnel, are we broken? And what training and enablement? are we investing in to go get there? And then I mean, my advice for any client that's, that's using database or anybody that we talked to you that way? Do you have rep-specific targets for every stage of the funnel? So if we're broken, in the end, we're not winning enough deals? Have you taken the time on the enablement team to break down where is that busted at the rep level then at the team level, then the director level, then at the VP level, so that you're investing the right amount of enablement? At the, for each of the skills that are missing, because a lot of people will just on win rate, and they go spend $500,000 for a half day seminar. And they invite a really cool firm to come and teach them something. And it's exciting for a month, and then nobody remembers it. And the enablement team is the only one that's gonna get that institutionalized.

16:18

Yeah, the and this is, and this goes back to our beginning point of having enablement. Roll up into Reb. Ops, if rev Ops is part of sales, right? Yes, I think what you're what I'm hearing from you is specific reporting. And like, looking at your funnel, right? Like, even if you don't set the goals, at least you're looking at the funnel. And you're breaking that down and seeing Okay, well, where's the choke point in the pipelines? Right? And that's what Rev ops does. So the closer those two worlds can work together, the better because you'll have a better outcome.

16:55

Yeah, cuz you have the dev ops team that knows all the data they're supposed to, you have the enablement team needing to know how to go actually loosen those chokeholds. If those two teams are working closely together, you've actually got a marriage that can happen. Too often, either. enablement is an afterthought. Oh, yeah, go build this, we need a deck that talks about how to do this, go build that for us. And that's, that's not exciting for the enablement person and be rarely going to get the reps fired up, they're probably going to say, Oh, it's just another deck, developed by enablement that we're not going to use. Whereas if enablement is in every one of the strategy meetings with the rev ops most senior leader or with the VP of sales, then it's going to match the vision that was there from the beginning.

17:40

Yeah, I think a good example this, and correct me if I'm wrong, but you know, in those meetings, you might decide that you're going to go all in on financial services this year, you know, you're going to pick an industry, you're going to go deep into an industry. And I think that having enablement in those conversations gives them that lead up for them to start to know, okay, well, we're going to start building content and training. And maybe there are tools that need to be involved there that can support us going deep into a vertical. And that because a rep might like oh, yeah, sort of like sold into this, but maybe it's kind of happenstance. So if you're going to have them go deep into that, then they're going to need to have the expertise, know all the right nomenclature, whatever else there is.

18:33

Yeah. And that's why I mean, like, if you even think about, like, why we call this fireside chat, 1/3 of your go-to-market focus should be enablement, it's that what 1/3 is going to be around what is the quota? And that just has to set finance, aligned 1/3? What is the work you have to go get done in order to hit that? And then 1/3? How are you going to go train every single person with the right materials, tech stack, and training in order to actually go and succeed? If you go and you look at like, if it's the military, like, I haven't even seen it yet. But I can bet that in the newest movie Maverick, there is going to be a huge portion of time just training on the mission, that they're gonna go get done, and then they're gonna do the mission. Well, the end mission is the quota. Yep. But everybody just talks about that. And they have, you know, strategy to go get there. Go watch any successful military venue, they spent an insane amount of time training and enabling the people so that when they actually go out and they're living in the real world, they're capable of handling all those situations. And that's why we have to remember that third that often gets forgotten.

19:41

The fact is, you don't need to think about it. It's just execution at that point. Yes. What about communication of the sales strategy, right? Like, I think that there's this piece. This is just my personal like, what I've seen with customers and just being in the planning world is that There's a lot of the sales strategy changes, maybe you change segment lines, maybe you go into verticals, maybe you go into like, they're gonna go roll out a pack, whatever the strategy is, right? A lot of that starts to change, but I think the communication to the reps gets dropped, like, why are we doing this? Kind of life really? Why are we doing this right? And then also supporting them? So do you feel like that is enablement? Responsibility? And do you have any like, examples of how you might tackle that to make sure that that gets done and reps feel like they've been a part of that conversation, or they understand where that company's headed?

20:46

Yeah, and again, as soon as you possibly can have a senior enablement leader, and having them in those meetings, somebody that will go and make sure that vision is shared, that's the best way of doing it. If you can't hire a senior enablement leader, your rev ops leader has got to go buy into the idea that 1/3 is all around enablement, and part of enablement is that vision of where we're going, why we're going to go get there, and then they build the plan to go do it. Okay, as part of our enablement strategy to go and nail this finance vertical using the analogy we're using earlier, the example I'm using earlier, we're going to go and spend an hour just talking about why this matters. Because if you look it'll force management to use a concept of first teach the principles, and why it matters, then showing them how it gets done in the real world, then observing them doing it in the real world. The same thing with vision, if you don't go spend that, okay, go show them or teach them why this vertical is so important to our company, then show them financial statements of the types of customers that we're going to go after the ideal customer profiles, then let them go on LinkedIn and see if they can pick those ideal customer profiles on their own and come back and share with you why it matters, that they're gonna go do that those types of things, enablement, leaders just come second nature to them.

22:03

Yeah, that's so that's super important that everybody takes that away because I think that that gets forgotten about. And whether you have an enablement leader or not, I don't know a lot. I think a lot of people go build this territory plan out and kind of almost throw it over the fence, and you're going to be working in financial services, here's some content, and we're going to help you but I don't know that the time is, I think there's what's missed is the why we're doing this and look at the opportunity here. And you get to be a part of this, right? Like that's the coaching of the strategy and making, like reps feel like they're bought in and a part of where the company is headed? Yeah. So where do you think people might miss the mark with enablement? What are some of the mistakes people make throughout this process?

22:59

So I think number one is they have it reporting to HR. And so it does. It's never an enablement team. It's an onboarding training team. So that's the most common mistake. Number two, it's not even considered. "Oh, yeah, we have enablement, they work with HR." It's like, "No, I don't even think about enablement, I'm just gonna go and drive accountability without developing teams." And so if there are not at the very seat most senior level, the vice president of sales at the head of revenue operations at the head of enablement, actual skill, target increases that they're measuring. So whether it is okay, we're gonna go from a 2% win rate to a 10% win rate or a 10%, to 15 to 25 to 30, that that becomes a measurable that they hold themselves accountable to on the training side. That's another big miss. They, they only have, okay, we're gonna have this much pipeline, we're gonna have this pipeline multiple, and we're gonna go hit this quota. Okay, well, what skills we're going to get better at to get there? So I think that's a major miss is that the very the most public targets that are shared across the company, they leave out enablement targets, leave those out, then the team's gonna think okay, all I really got to do is hit my quota. If I got there by one deal, that was an inbound lead that had nothing to do with my skills. That's just as good as if I didn't do four deals that I found on my own. And my win rate was above 40%. If it doesn't get that clear to a rep, that those two are not two equal worlds, they're just gonna go through the easiest way possible to hit their quota lucky or not. And then what will eventually happen is your sales team is built on a house of cards and getting to a very, very low percentage of reps hitting quota.

24:45

Are you suggesting that people set targets or get the reps as it relates to getting enablement done or the enablement team has the same targets so they know that okay, I got to try and increase win rates? So I've got to provide Add content that I think is going to do that.

25:02

Yeah. For any organization that I advise, own or lead, the enablement team has a measurable target on each of these metrics. So if there is an outbound motion in the company, answer rate, so what percent of cold calls get answered? Set rate, what percent of those the answer agreed to meet, show rate, what percent of those that agreed to meet show up the opportunity conversion rate of those that show up what percent convert into pipeline stage progression, so through each stage, win rate, and average deal size, so the enablement team has that entire funnel, and every quarter, an increase target, okay, we're going to increase our global answer rate from 8% to eight and a half. And then they go and build individual tactics as to how they're going to get there. And the same thing all the way down to average deal size, and that you have the most important one, that the VP of sales is like, let's say that a win rate. I remember one company I helped out win rate was at 2%. And it's like, Okay, we have to get it to 10% as soon as humanly possible because it is brutal on the reps to have to call this much to only lose almost every deal. They were monster deals. And so they went one deal, and it would cover up a lot. But either way. So anyway, the goal was to get it to 10%, and then eventually to 25%, as soon as possible. So you publicize that target. You talk about how the head of enablement is going to be working on this across the whole company, as well as these other metrics. But that we're going to go get there together as a team. And if that head of Reb, ops, head of enablement, and head of sales all have the same target, it's talked about as often as revenue and pipeline generation, then you see a lot more success and sustained.

26:54

Everybody's aligned. They all hope they're all rooting for the same camp. You've mentioned tech stack a couple of times. And the piece I just wanted to really tease out here is how does that play? So you've got the target, right? Does that exist? Doesn't matter what it is, it could be win rate, or new opportunities, or whatever that might be right? How does a tech stack play into, like an enablement strategy to get that increase? Right, that I feel like there's like tech stack. And then there's also just like training and content that happens, how important is the tech stack part of this

27:34

thing, it's huge, because the tech stack is supposed to make everybody's job easier, you buy technology to make your job easier, otherwise, you just have people do it. And so the enablement team should be looking at, okay, we just bought this software doesn't matter what the software is, our job is to make it to where that software gets adopted, used. And those metrics that we're now talking about are easier to achieve. And so it should be looking as if you just bought AI for forecasting, then you should be looking at, okay, well then our accuracy of the forecast. And maybe the CRO also thought it was going to increase win rate, because we're going to focus on the right deals, okay, so we're gonna go and invest in training this part of the technology, to every rep, we're going to do a certification, because we believe that's going to go work, and we're gonna go help them or it's a CRM, our hygiene is garbage, people are not entering this information in as such, we have no idea and how to go help them. So we're going to take it on ourselves to go and train on that technology. And, in my opinion, there are a few parts of software that you need, we would have to spend another 30 minutes just talking about that. But what I would recommend to the enablement team, is that you should be looking really closely at every piece of software that's been purchased for the revenue team. What have you done to make sure that it achieves the outcome that that head of Rev Ops Head of Sales sought was going to go in and happen and align yourself to that?

29:08

super interesting. It's amazing how fast these 30 minutes go. I'm telling you, part of me wants to extend these out. But part of me doesn't, because they're nice and short. Right? So do you have any final parting thoughts for our audience today?

29:28

And the one bullet point two bullet points? I would say you do one, ask yourself, Are you part of an organization that buys into developing those around them? If you're part of that organization, and you're in enablement, you've got an amazing good, go make something special that if you're not see if you can change it, get there, get the culture and the mindset changed. If not leave, go to an organization that believes in developing its people as part of the enablement strategy. Second, align yourself to measurables. Enablement teams get forgotten about and cut because they're not aligned. In two measures are metrics that the CFO and the CRO care about. Align yourself to those enablement metrics that I was talking about, and present at least once a quarter on the progress that you're making. And you will be the team that gets funded the most. So if you do those couple of things, and enablement 1/3, at least have the go-to-market strategy have a lot of success.

30:20

And that's the biggest one for me too, is the alignment of those goals. I think that's huge. I never really thought about it that way. But that's kind of what I'm gonna walk away from this today. So, Dan, thank you so much for taking the time and joining us. Till next time. Thanks, everybody for coming in. Have a good one.