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Ever feel like sales enablement gets the blame for every failure in your organization? Or no matter how convinced you are a new tool would be successful you’re faced with rejection after rejection?

In this article, I want to share some tips, tricks, and tools, using metrics and data, to help you battle these problems and get you more credibility within your company, get in a more strategic role, and propel your career as well as your organization.

  • Who's ever requested headcount or a training tool and they've been denied?
  • Who's ever worked in an organization where every failure is sales enablement's fault, but you never get enough resources to fix it, even though you know how?
  • Who's ever reported to an SVP of sales ops and you've got a big initiative that you bring up with him to get some support right before he goes and meets with your CRO, and you find out when you circle back later that all they did was talk comp and ROE the entire time, and your issues never got discussed?

Okay, that last one's a little personal for me - stings a little bit still.

What I'm going to write about in this article is aimed at hopefully giving you some tools, some tips, and tricks that I've learned along my career to help you battle through these problems, get some more credibility, and find ways in which we can present our ideas and get ourselves more in a strategic role, rather than just a training role.

Pain points

Some of the pain points - when I say I'm going to write about data today, some people say, "That's not my job". Some people might say, "I don't know what to do with it if I had it, I don't know where to begin or what to track. And I don't know what to do once I am tracking it".


To cover that, I'm going to step through a couple of these things in this article about why we should prioritize data and analytics, what we should be looking at, and giving you some actionable metrics that we can start to track now and how we can implement those right off the bat, and what to do with it next.

pain points and agenda

About me

I want to tell you a little bit about me first, I fell ass-backward into sales enablement, and it's been the greatest thing that ever happened to me.

I was working at an accounting firm during tax season, I quickly realized I did not want to do accounting. At the end of tax season, I took my bonus, ran off backpacked, hitchhiked through Central America for four months, and I came back absolutely broke.

I learned something important about myself - I didn't really care about working in accounting, but I did love to travel. Unfortunately, being broke after that trip, I had to go back to work for the accounting firm and go back into school.

But I got an email from my university from a local company that was looking for international training interns. I said, "Oh, someone else will pay me to travel around? Alright, I'll take a shot on that". I started as an intern, and that started my journey in sales enablement and sales training.

about Kyle Doerflein

Now, throughout my time, I've worked in a lot of different roles at a lot of different companies, and one of the ones that I'm going to share a lot of experience from you guys today is about the four years I spent working for a BI and analytics company.

Taking those things that I've learned the hard way, I'm going to hopefully show you some things that you can take as actionable insights to go back, build your credibility, and build your brand into more of a strategic role.


But we need to figure out why this matters. I feel and I think this is a truth - that sales enablement can have a higher impact on a company's revenue and growth than any sales ops role.

The reason being is you can change comp, and that might try to motivate a behavior, but if reps don't know how to execute on it, it's all useless. It's all a waste of time.

Being able to educate your reps, and being able to have a higher impact not only will help you out as you advance your career, but it'll help you be able to prioritize and strategize the initiatives that you're driving and figuring out where to spend your time to benefit the company as a whole, but also to grow your personal career, your compensation.

Back to my front door brag. I want you to focus on some of the different changes in the wording on the image below.

a little more about Kyle Doerflein

The evolution of sales enablement

We start to see the evolution of training to enablement to productivity. There is an evolution right now and the timing is right. Enablement is going from a training function historically of just education, to where the world and business world is realizing how it can have a massive impact on the strategy, the efficiency, the productivity, and the execution of a company.

We're going across and we're working from an education point of view to a strategic point of view and a strategic impact.

From training to strategy

In 2013, according to CSO insights, fewer than 20% of companies had a dedicated resource that was specific to sales enablement. By the end of 2017, almost 60% of organizations focused on this critical business function. That was two years ago.

by 2017 almost 60% of organizations focused on sales enablement

There is a massive shift in the market going on right now in what we do. We're no longer just training, we're starting to make that step up. There are people in the industry who are building out career paths that we can model ourselves after and follow.

We've got people like Scott King, Stacy Justice, and Dixon Wong, who already have strategy in their title. They're not just educating. They're impacting the flow and the function of the entire revenue operations of their company.

This is the thing that we can do - not only impact and influence and grow our company’s success but also selfishly, we can grow our careers along the way.

Who's seen Training Day with Denzel Washington? It's a great film. In this movie, there's a rookie cop, who was with his boss and saw him kill somebody - he knew he was corrupt. He's trying to arrest him, and Denzel Washington teaches a very, very simple principle that I think applies to us.

its not what you know, its what you can prove - denzil washington, training day

It's not what you know, it's what you can prove.

It doesn't matter that we know in our gut what the organization needs to do. It doesn't matter that we've seen this before, we've done this and have this impact. If we know it internally, but we can't prove it, leadership's not going to care.

Those big-ticket items of comp, ROE, the things that might be important in that room on the C suite, we might not get the visibility up to that level. What we need to do is figure out how we can prove this.

At the BI company I worked for we had a saying it was more appropriate for the tech world but it went as follows:

'Opinion versus opinion, title always wins. Opinion versus data, data always wins'.

We knew that if we walked in and we were pitching an idea and I wanted my president of sales to do something and I said, "Hey, we need to focus on this initiative, we need to devote resources to this project that we want to do". He'd say, "Oh, I've seen that happen before it didn't work, not going to do it".

My opinion versus his opinion, he's gonna win every time.

But if I go in with data, and if I go in with a story, and if I can show metrics of where we're at, what we're doing, and where we can go, I can grab his attention a little bit more.

I've talked a little about why we should care, hopefully, everyone's invested enough into that between helping your companies, the impact you can have, your career path, and how that generates more money and compensation in your pocket.

But now, what should we focus on? What metrics should I be watching?

What should I measure?

I want to get granular with some of this stuff and be prescriptive to you about things that I've focused on in the past that have helped me out.

There are two categories that I'm going to look at.

objectives vs. metrics

Baseline metrics

If my objective is to demonstrate value in the enablement program and just build our brand and our reputation throughout the org to get that trust and confidence from my leaders and teams, I'm going to focus on what I call the baseline metrics, the must-have things that I'm tracking from the get-go.

ROI metrics

But if I'm going back and trying to justify tools, headcount, a specific training initiative that I want them to buy into, I might focus on ROI initiatives, and ROI metrics.

They're similar, but I would use them and message them in different ways and I'm going to dive into them one by one.

Baseline metrics

The first thing we're going to look at is those I call baseline metrics.

Some of the five baseline metrics that I'm tracking and the first things I implement at any company I go to are:

  • My time to first deal,
  • My number of opportunities,
  • My average deal size,
  • My average conversion rate, and
  • My average sales cycle.

Each one of these metrics has a purpose. Each one of these things allows me to have visibility into how my organization's performing in different ways, the five different levers that I can play with, that I can pull, and that I can move to drive my overall goal, which in sales enablement, is driving revenue up.

  • Time to first deal - what does that measure for us? Onboarding and ramping.
  • Number of opportunities - prospecting.
  • Average deal size might give us our value selling or multi-threading - are we selling cross-departmental or are we getting multiple departments in on a deal?
  • Average conversion rate - sales cycle and sales skill efficiency - how efficient we are in the conversations, the actions that our sales teams doing.
  • Average sales cycle will give us that but it'll also talk to us about our process efficiency. Are we doing things in the right way? Are we doing these things in the right order? Are we approaching our customer in a way that they like to buy?
baseline metrics

I'm curious about the other metrics you're seeing that you use for your baseline metrics that you need to have at any company you go to. It really depends on what your objectives are as a company.

My objectives, the problem I was brought in to solve was to increase and drive revenue growth, we're in a very quick growth stage of our company. If it's maintaining the company size, and if it's maintaining that tribal knowledge in the company, retention might be one of those.

These ones are some of the fundamentals but depending on what your objectives and your goals are, from a higher level, what your charge is from your C-level leadership, you might change these and you might have different things that you're looking to do. But you should always be tracking something.

These ones are fairly consistent in my experience over every sales enablement program that I've been in. If we start tracking these, and we start looking at them over time, and we want to visualize it, what would that look like if we automate this and visualize it?

I'll show you what mine looked like.

baseline metrics  - examples

We might have these graphs, and we might have them trended out and so we might be able to look for different things.

  • How is my sales cycle doing?
  • Is it getting shorter?
  • How's my average deal size?
  • Is that growing?
  • What does my pipeline look like?
  • How are we flowing through?
  • How are my days to first and second deal?

Once we have this baseline set, and we start looking at these metrics, and we start getting that visual view of how we're doing and how we're performing, we can start to dive into them deeper and look for opportunities for prioritization, opportunities for impact.

Dive into the data

Let's focus on some of these right here.

dive into the data

By diving in and looking at this, we might be able to see that these two teams - my central and my west teams - their average sales cycle is very high. Where are we going wrong?

By digging into that data, we might realize that they're not doing well in their procurement management and their negotiation phase. We might come in and do training.

We might realize that our SMB team was experiencing some great growth, but then we changed our pricing model, and ever since then it dropped off. We've had terrible performance from that team.

By looking at our data trended over time, we could also see, why are we losing so much of our sales funnel right here at demo?

  • Is it that we aren't qualifying well enough and a lot of crap leads are getting through?
  • Is it that we're not building enough value in the discovery process?

By digging into this and getting a visual representation, we can see opportunities for impact, we can see opportunities to influence our ROI.


Diving into these we can also start to compare the projects and say which one of these can have a bigger impact, we have limited bandwidth, we can only focus on so much, so which one is most important?

We can start to model that out and figure out who do we need to bring back to the baseline?

ROI metrics

I want to dive into ROI metrics because this is a tricky piece.

Yeah, you can show correlation, you can so show causation, but how do I justify a new headcount or a new tool? Here's one that I use.

ROI metrics

Build out correlations

I overlaid my learning management system on data from our CRM, and I was able to show a correlation.

Let's say we implemented Saleshood at the beginning of the year - our learning management system, our coaching tool - and we found that with the limited content that's in there, there's a distinct correlation between the videos watched and the activities performed, and the ARR the ACV, the revenue that's generated on a rep by rep basis.

This tells me that it was a good investment. There's a correlation there. By diving into it a little bit deeper, I can build this out, and then I can go to my leadership and have a conversation and say,

"Okay, so it's working but there's not a lot of content in there. If we want, let's devote another headcount to it",


"Hey, let's not cancel that LMS we just bought when it comes up for renewal because it's clearly helping drive good results".

You can start to have those difficult conversations and start to justify that the things we're spending money on are working, or there are things that we're spending money on, that are working that we need to spend more money on, get an additional headcount, build out more learning modules for these different tools.

Days to first and second deals

The next piece, looking at our time to first and second deal - is our boot camp working? If we iterate on it every time to try and improve this process we should see that yeah, it might take a lot of time to get to that first and second deal, but each time we make a change, each time we evolve that, it's getting better.

We're getting our time to productivity, our time to break even on that investment in hiring new reps down lower and lower.

We can come in and we can see we did the training where we stepped in on the team meetings for the East and Central teams. We trained them on procurement negotiations and then we saw those numbers dropped down then went back up.

ROI metrics - examples

So we came back in and we started to bring them down again, we start to be able to see, did we solve the problem? But then we can also start to correlate and say, "Hey, did their close rate go up? Did their close rate from procurement negotiation to close, did that increase?"

Attributable value

Because that percentage that it increased, especially on those teams, that's attributable to us, now we're putting $1 value ROI on the work that we're doing.

Same thing on the discovery and demo training, if we take a snapshot and look at that, and we compare it to after we do that training, and we notice that right here, that funnel, the next time we looked at it was 25% bigger, which still had some loss, but at the bottom line, came out with 5% more deals, that 5% of deals can actually be tied to a dollar value number where you can say 'I did this training and it was worth this many dollars to this organization'.

Building that brand, building that recognition, sharing this out, getting that visibility is going to help you have credibility, to know, are we doing the right things at the right time, and is it working?

And if it's not working, taking the accountability to say, that didn't work, let's dig into it again, figure out what the real problem is and solve that.

What do I do with it now?

I'm tracking this, I've got these different instances, I've got this many stories where I've done this change, I've made this training, I've had this conversation, I've coached this team, it had this impact, and we've got all these little different wins along the way. What do I do with that?

Internal sales and marketing

How do I use that to build my brand, build my credibility, to drive the strategy of my program?

Buyer journey

Think of it like a buyer journey. When you're selling an idea, you should use your buying process. When you're trying to get people in the organization aligned, when you're trying to get buy-in from different stakeholders, you are selling an idea.

Bottom line, we all are in sales enablement, we all should know the buying and selling process. You're selling an idea - rely on that process.

Because these interactions are a sale, you're either selling them on why they should invest in your deal or prioritize your initiative, or they're selling you on why they can't do it, or why they shouldn't do it, or why they don't want to.

linear buyer journey map

If we look at it as a buyer journey, our baseline metrics might give us awareness of an issue where we can identify something we have to work on.

While we're trying to build a solution, we might refer back to a previous issue that we solved with enablement and training that's similar to get them interested in like, "Oh, yeah, if that solution worked then it might work again, let's take a look into that deeper".

As we're working our way through our buyer journey, we're using these like customer success stories. We're getting our audience comfortable and confident that we know what we're doing, we've done it before, this is the right solution. You're selling your idea.

Once you've sold your idea it doesn't end there. After you get that buy-in, you still have to continue to track afterward so you can get those ROI metrics because then the loyalty piece comes in.


This loyalty piece is like customer marketing, when you sign up a customer, and they're paying you and they're happy, you don't end there. You continue to nurture that relationship, you continue to send emails, newsletters, blogs, because you either want them to increase their investment in your product or at least continue to stay happy.

Same thing for us. We've done internal sales, we've sold the idea, now we need to do the internal marketing.

internal sales and marketing

What are some ways in which we can share out these wins and these successes?

It might be sending a summary back to your leadership and the stakeholders after every Bootcamp.

They graduated, these were their scores, this is their performance so far, you're doing check-ins to show how well they're ramping, how quickly they're hitting those targets.

You might include it in your weekly updates, send directly to your leadership, report back to your steering committee if you have one.

You might share it in QBRs - in all of my QBRs I get up there and do an update on these are the trainings we did, these are the impact that they had, this is how our organization is improving because I want all of my directors, managers, and VPS to know that they can trust on me to help solve their problems - when they have issues they can come to me.

If our stakeholders are our clients, we are not only the consultants, we're also our sales and marketing team. Sharing those in the QBRs, in your annual planning when you're asking for headcount and tooling budget for next year,

"Hey, guess what you gave me this much last year. This is the impact we had. These are the changes we made, trainings we've done. revenue generated. Let me show you some correlation between that tool we implemented and the close rates and how we're cutting down our average deal size".

Tying all of these successes back and sharing them, especially in annual planning, is going to give them the confidence that you know what you're asking for and you know that what you're asking for is going to have a positive impact, they're more likely to give it to you.

And then also even ad hoc plans throughout the year, including in business plans for tools.

An example

One we recently went through is we bought Gong, we tracked our average close rates, we tracked our average sales cycle, our average deal size, and our average time to first and second deal.

We got a baseline for what it was before we implemented the tool. We implemented the tool. We watched that track down. And then we identified that we also needed a new LMS (learning management system).

So, in my pitch for the LMS, I said, "Listen, this is what we achieve just by adding in call recording and coaching. If we make it more efficient, if we add in an LMS where we can have on-demand learning, we can automate our process, we can start to make it so we aren't as heavily reliant on headcount. We can be more strategic about how we deliver information to our teams and we can expect these numbers to go down and we can expect our onboarding time to productivity to go down".

Building that case, sharing those success stories, being your own sales and marketing team.

Final thoughts

Get your baseline data, start looking at things.

Start seeing the trends, start seeing where you can have an impact, where it's going to change, start to calculate your ROI and your impact by snapshotting before and after, and watching, whether it's working or whether it's not.

Identify whether you've solved the problem, or you need to revisit it before moving on to the next initiative.

Internally sell your ideas, use your sales process, use your successes like customer success stories.

Internally market to your team's successes, get everyone in the organization visibility on 'we're part of the solution'.

Take accountability for your failures, but build that credibility, learn from them, and show where we can get better, where we're helping, and where we can devote more resources for more opportunities.

Doing this helps you evolve from just being an education and training function that's ignored to being part of the strategy and the solution, to being in that high-level room where they're saying,

  • What should we do next?
  • What do we need to tackle next?
  • What is the next big problem that's going to get us to 75 million?
  • What are we going to change this next year to get to 120 million?

You start to become part of that solution, rather than an ancillary, "Well, they're in charge of them for one week before we really throw them in the deep end".

We have to evolve our visibility to evolve our impact. It all comes back to this.

It's not what you know, it's what you can prove.

Opinion versus opinion, title always wins. Opinion. vs data, data always wins.

If we take this, we live it, and we start to build out some of these analytics, these metrics, and these best practices, you will be able to elevate yourself, elevate your credibility in the org, accelerate your career path.

Whether your end goal is CSO, chief productivity officer, VP of sales strategy, whatever that is, you can grow your impact in your org, you can grow your influence, your career, until you get to the point where internally you just know and you're thinking of one of those other great quotes from Training Day.

its not what you know its

King Kong ain't got shit on me.

Thank you very much.

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